CN105585847A - Positive-working PSPI (photosensitive polyimide) composition with low CTE (coefficient of thermal expansion) and high resolution - Google Patents

Positive-working PSPI (photosensitive polyimide) composition with low CTE (coefficient of thermal expansion) and high resolution Download PDF

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Publication number
CN105585847A
CN105585847A CN201510996585.1A CN201510996585A CN105585847A CN 105585847 A CN105585847 A CN 105585847A CN 201510996585 A CN201510996585 A CN 201510996585A CN 105585847 A CN105585847 A CN 105585847A
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composition
photosensitive polyimide
polyimides
coefficient
pspi
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季昌彬
徐亮
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SUZHOU RUIHONG ELECTRONIC CHEMICAL PRODUCT CO Ltd
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SUZHOU RUIHONG ELECTRONIC CHEMICAL PRODUCT CO Ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
    • C08K5/27—Compounds containing a nitrogen atom bound to two other nitrogen atoms, e.g. diazoamino-compounds
    • C08K5/28—Azides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
    • C08G73/105—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the diamino moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1075—Partially aromatic polyimides
    • C08G73/1078—Partially aromatic polyimides wholly aromatic in the diamino moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/08—Stabilised against heat, light or radiation or oxydation

Abstract

The invention discloses positive-working PSPI (photosensitive polyimide) composition with low CTE (coefficient of thermal expansion) and high resolution and belongs to the field of integrated circuit packaging materials. For the composition, a PI solution is formed through copolymerization of 4,4'-(hexafluoroisopropylidene) diphthalic anhydride (6FDA), 2,2'-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane (HFBAPP) and 4,4'-diaminodiphenyl ether (ODA) under the action of a catalyst, then a diazonaphthoquinone esterified photosensitizer, an additive and a solvent are added and uniformly stirred, and the high-performance positive-working PSPI composition with low CTE (lower than or equal to 15*10<-6>/DEG C) and high resolution (3 mu m L/S is equal to 1:1) is obtained.

Description

A kind of low thermal coefficient of expansion high-resolution positive photosensitive polyimide composition
Technical field
The present invention relates to microelectronic packaging material field, be specifically related to a kind of Novel low coefficient of expansion (CTE)Have both the preparation method of high-resolution positive light-sensitive polyimides.
Background technology
Microelectronics industry has now become mainstay of the national economy type industry, is to weigh a national science technology waterThe important symbol of gentle overall national strength. Along with the super ultra-high capacity of electronic device, microminiature, very-high performance, superThe future development of high reliability and cost degradation, sharply increases the packaging density of integrated circuit (IC),Requirement to encapsulating material performance is also more and more higher.
In IC device assembling process, to use metal, semiconductor and polymeric material simultaneously. Different materialsBetween not mating of thermal coefficient of expansion (CTE) tend to cause device inside to produce stronger internal stress. Internal stressExistence can cause on the one hand device inside metal or lead-in wire that deformation occurs and cause the variation of device parameters, moreFor serious be to cause encapsulation cracking, moisture and ionic substance enter device inside and cause deviceThe actual effect of part. For this reason, in IC device equipment process, tend to adopt passivation stress buffer technique (PSB),The polymeric material good by, Heat stability is good lower by CET value, size and chemical stability delaysRush the stress of device inside.
Polyimides (PI) has good combination property, can meet the performance requirement of PSB technique, because ofThis is used as the stress buffer coating of IC device for many years always. Relatively traditional non-photosensitivity PI need be by commonThe technological operations such as photoresist charts, through hole, due to Reusability wet-etching technology, therefore photoresistThe shortcoming that graphics resolution is low, side wall profile is poor, IC system has been simplified in the birth of light sensitivity PI (PSPI) greatlyFabrication technique has improved the precision of litho pattern simultaneously.
Compared with negativity PSPI a little later, because process route is immature, image repeatability in the research of positivity PSPIThe reasons such as difference, make its slower development. But positivity PSPI is owing to can providing higher resolution ratio and at aqueous slkaliLower development, without the advantage such as develop in organic solvent, becomes in light-sensitive polyimide most active one recentlyClass. Along with the continuous progress of science and technology, the positivity PSPI of existing market circulation can meet the need of IC technique substantiallyAsk, but still have many problems and shortcomings, such as being situated between, some constant (ε) is higher, and CTE is higher, and Tg is higher, drawStretch undercapacity, the problem that resolution ratio is on the low side, these deficiencies are all restricting the raising of IC encapsulation performance.
PI precursor/positive quick formulation of the third contact of a total solar or lunar eclipse is the positivity PSPI that current research is the most abundant, commercialization degree is the highest. PIPrecursor has a lot of types, in these PI structures, adds some special constructions, and side chain is with alkali as shown in Figure 1Dissolubility group, hexafluoro isopropyl, sulfonic group etc., Jie that can effectively reduce PI puts constant and CTE. JoinClose high-contrast, diazonium naphthoquinone sulphonate class sensitising agent that esterification degree is lower, be equipped with solvent and additive obtainsTarget low thermal coefficient of expansion high-resolution positivity PSPI.
Summary of the invention
The problems referred to above that exist for prior art, the invention provides a kind of low thermal coefficient of expansion high-resolutionPositive light-sensitive polyimides. In the present composition, polyimide solution is by 4, the adjacent diformazan of 4 '-hexafluoro isopropylAcid anhydrides (6FDA), 2,2 '-bis-[4-(4-amino-benzene oxygen) phenyl] HFC-236fa (HFBAPP), 4,4 '-diaminesYl diphenyl ether (ODA), catalyst copolymerization form, and add diazo naphthoquinone carboxylate sensitising agent, additive, moltenAfter stirring, agent obtains CTE≤15 (× 10-6/ DEG C), resolution ratio 3umL/S=1: 1 positivity PSPI composition.
Technical scheme of the present invention is as follows:
Add 2,2 ' appropriate-bis-[4-(4-amino toward being equipped with in the there-necked flask of reflux condensation mode whipping temp counter devicePhenoxy group) phenyl] HFC-236fa (HFBAPP), then add appropriate 4,4 '-diaminodiphenyl ether (ODA)Stir. Stir and dissolve 4 of rear point of three interpolation equimolar amounts completely, the adjacent dicarboxylic acid anhydride of 4 '-hexafluoro isopropyl(6FDA), mechanical agitation makes transparent thick polyamides Asia for 6 hours under proper catalyst ultrasound environments in additionAmine.
So that necessarily the polyimide solution than part, diazo naphthoquinone type carboxylate, additive, solvent are just being allocatedProperty photosensitive polyimide composition.
Preferably described polyimides, it is characterized in that described with 4, the adjacent dioctyl phthalate of 4 '-hexafluoro isopropylAcid anhydride (6FDA), 2,2 '-bis-[4-(4-amino-benzene oxygen) phenyl] HFC-236fa (HFBAPP), 4,4 '-bis-amidosDiphenyl ether (ODA) and polymerization catalyst form.
(1) described polyimides, is characterized in that dielectric constant (ε) is between 2.0-2.2.
(2) described polyimides, is characterized in that thermal coefficient of expansion (GTE)≤13 (× 10-6/℃)。
(3) described polyimides, is characterized in that hot strength/MPa >=160.
(4) described polyimides, is characterized in that Tg/ DEG C >=320.
Preferably described positive photosensitive polyimide composition, is characterized in that the quality of contained each componentMark is:
(1) described positive photosensitive polyimide composition, is characterized in that diazo naphthoquinone type carboxylateComprise 2,1,5-DNQ and 2, one or more of Isosorbide-5-Nitrae-DNQ.
(2) described positive photosensitive polyimide composition, is characterized in that solvent comprises propane diols firstEther acetate, propylene-glycol diacetate, 3-ethyoxyl-3-imines ethyl propionate, N-crassitudeOne or more in ketone, 2-heptane, 3-heptane, cyclopentanone, cyclohexanone.
(3) described positive photosensitive polyimide composition, is characterized in that dielectric constant (ε) exists2.2-2.5 between.
(4) described positive photosensitive polyimide composition, is characterized in that thermal coefficient of expansion (GTE)≤16(×10-6/℃)。
(5) described positive photosensitive polyimide composition, is characterized in that hot strength/MPa >=140.
(6) described positive photosensitive polyimide composition, is characterized in that Tg/ DEG C >=250.
(7) described positive photosensitive polyimide composition, is characterized in that the limit inferior at thickness 10umResolution ratio reaches 3umL/S=1: 1.
The present invention passes through with 4,4 '-hexafluoro isopropyl adjacent dicarboxylic acid anhydride (6FDA), 2,2 '-bis-[4-(4-aminobenzene oxygenBase) phenyl] HFC-236fa (HFBAPP), 4, the polyamides Asia that 4 '-diaminodiphenyl ether (ODA) is polymerizedAmine aqueous solution, is equipped with diazo naphthoquinone type sensitising agent, additive, solvent and allocates and form by a certain percentage. The present inventionPreparation method is simple, and Miscibility is better, obtains lower dielectric constant and thermal coefficient of expansion, thermally-stabilisedProperty is good, and high-resolution positive light-sensitive polyimides can meet harsh to encapsulating material of integrated circuitRequirement.
Brief description of the drawings
Fig. 1 is the PI structure chart in background technology of the present invention;
Fig. 2 is the resolution ratio SEM figure of positive light-sensitive polyimides in the invention process regulations 1;
Fig. 3 is the resolution ratio SEM figure of positive light-sensitive polyimides in the invention process regulations 2;
Fig. 4 is the resolution ratio SEM figure of positive light-sensitive polyimides in the invention process regulations 3;
Detailed description of the invention
Below in conjunction with drawings and Examples, the present invention is specifically described.
Embodiment 1
With 4,4 '-hexafluoro isopropyl adjacent dicarboxylic acid anhydride (6FDA), 2,2 '-bis-[4-(4-amino-benzene oxygen) phenyl] sixFluoro-propane (HFBAPP), 4, the preparation of the polyimide solution that 4 '-diaminodiphenyl ether (ODA) is raw material:Add 28.6g2,2 '-bis-[4-(4-aminobenzene oxygen toward being equipped with in the there-necked flask of reflux condensation mode whipping temp counter deviceBase) phenyl] HFC-236fa (HFBAPP), then add 4 of 14.4g, 4 '-diaminodiphenyl ether (ODA) stirsMix evenly. Stir and dissolve 4 of rear point of three interpolation equimolar amounts 13.3g completely, the adjacent dioctyl phthalate of 4 '-hexafluoro isopropylAcid anhydride (6FDA), under 0.4g catalyst ultrasound environments, mechanical agitation makes transparent thick polyamides for 6 hours in additionImines.
The preparation of positive photosensitive polyimide composition and resolution ratio section test, the quality hundred of each component proportionProportion by subtraction is as follows: polyimide solution 29.2%, 2,1,5-DNQ carboxylate 21.5%, 0.7% additive,48.6%NMP is stirred to and mixes, and obtains positive photosensitive polyimide composition, records GTE=15(×10-6/℃)。
Positive photosensitive polyimide composition, after 0.25um filter filters, is coated on wafer through spin coating,Soft roasting 2min on 200 DEG C of hot plates, 250mj.cm exposes under i-linestepper-2, after PEB210 DEG CIn 2.38%TMAH alkali lye, develop, after rinsed with deionized water to figure consistent with light shield, under SEM, cut into slicesAs shown in Figure 2, as can be seen from the figure 3um svelteness is steep for figure.
Embodiment 2
With 4,4 '-hexafluoro isopropyl adjacent dicarboxylic acid anhydride (6FDA), 2,2 '-bis-[4-(4-amino-benzene oxygen) phenyl] sixFluoro-propane (HFBAPP), 4, the preparation of the polyimide solution that 4 '-diaminodiphenyl ether (ODA) is raw material:Add 42.9g2,2 '-bis-[4-(4-aminobenzene oxygen toward being equipped with in the there-necked flask of reflux condensation mode whipping temp counter deviceBase) phenyl] HFC-236fa (HFBAPP), then add 4 of 21.6g, 4 '-diaminodiphenyl ether (ODA) stirsMix evenly. Stir and dissolve 4 of rear point of three interpolation equimolar amounts 20.0g completely, the adjacent dioctyl phthalate of 4 '-hexafluoro isopropylAcid anhydride (6FDA), under 0.6g catalyst ultrasound environments, mechanical agitation makes transparent thick polyamides for 6 hours in additionImines.
The preparation of positive photosensitive polyimide composition and resolution ratio section test, the quality hundred of each component proportionProportion by subtraction is as follows: polyimide solution 29.8%, 2,1,5-DNQ carboxylate 21.7%, 0.7% additive,47.8%NMP is stirred to and mixes, and obtains positive photosensitive polyimide composition, records GTE=15(×10-6/℃)。
Positive photosensitive polyimide composition, after 0.25um filter filters, is coated on wafer through spin coating,Soft roasting 2min on 200 DEG C of hot plates, 250mj.cm exposes under i-linestepper-2, after PEB210 DEG CIn 2.38%TMAH alkali lye, develop, after rinsed with deionized water to figure consistent with light shield, under SEM, cut into slicesAs shown in the figure, as can be seen from Figure 3 3um svelteness is steep for figure.
Embodiment 3
With 4,4 '-hexafluoro isopropyl adjacent dicarboxylic acid anhydride (6FDA), 2,2 '-bis-[4-(4-amino-benzene oxygen) phenyl] sixFluoro-propane (HFBAPP), 4, the preparation of the polyimide solution that 4 '-diaminodiphenyl ether (ODA) is raw material:Add 57.2g2,2 '-bis-[4-(4-aminobenzene oxygen toward being equipped with in the there-necked flask of reflux condensation mode whipping temp counter deviceBase) phenyl] HFC-236fa (HFBAPP), then add 4 of 28.8g, 4 '-diaminodiphenyl ether (ODA) stirsMix evenly. Stir and dissolve 4 of rear point of three interpolation equimolar amounts 26.6g completely, the adjacent dioctyl phthalate of 4 '-hexafluoro isopropylAcid anhydride (6FDA), under 0.8g catalyst ultrasound environments, mechanical agitation makes transparent thick polyamides for 6 hours in additionImines.
The preparation of positive photosensitive polyimide composition and resolution ratio section test, the quality hundred of each component proportionProportion by subtraction is as follows: polyimide solution 29.6%, 2,1,5-DNQ carboxylate 21.4%, 0.6% additive,48.4%NMP is stirred to and mixes, and obtains positive photosensitive polyimide composition, records GTE=15(×10-6/℃)。
Positive photosensitive polyimide composition, after 0.25um filter filters, is coated on wafer through spin coating,Soft roasting 2min on 200 DEG C of hot plates, 250mj.cm exposes under i-linestepper-2, after PEB210 DEG CIn 2.38%TMAH alkali lye, develop, after rinsed with deionized water to figure consistent with light shield, under SEM, cut into slicesAs shown in Figure 3, as can be seen from Figure 4 3um svelteness is steep for figure.

Claims (6)

1. a composition for low thermal coefficient of expansion high-resolution positive light-sensitive polyimides, is characterized in that contained eachThe mass fraction of component is:
2. a composition for low thermal coefficient of expansion high-resolution positive light-sensitive polyimides, is characterized in that dielectric is normalNumber (ε) between 2.2-2.5, thermal coefficient of expansion (GTE)≤16 (× 10-6/ DEG C), hot strength/MPa >=140、Tg/℃≥250。
3. a composition for low thermal coefficient of expansion high-resolution positive light-sensitive polyimides, is characterized in that at thickness10um limit inferior resolution ratio reaches 3umL/S=1: 1.
4. positive photosensitive polyimide composition according to claim 1, is characterized in that described polyamides AsiaAmine 4,4 '-hexafluoro isopropyl adjacent dicarboxylic acid anhydride (6FDA), 2,2 '-bis-[4-(4-amino-benzene oxygen) phenyl] hexafluoroPropane (HFBAPP), 4,4 '-diaminodiphenyl ether (ODA) is polymerized, and concrete steps are as follows:
Add 2,2 ' appropriate-bis-[4-(4-toward being equipped with in the there-necked flask of reflux condensation mode whipping temp counter deviceAmino-benzene oxygen) phenyl] HFC-236fa (HFBAPP), then add appropriate 4,4 '-diaminodiphenyl ether(ODA) stir. Stir and dissolve 4 of rear point of three interpolation equimolar amounts, 4 '-hexafluoro isopropyl completelyAdjacent dicarboxylic acid anhydride (6FDA), in addition under appropriate catalyst ultrasound environments, mechanical agitation makes for 6 hoursBright thick polyimides.
5. polyimides according to claim 1, it is characterized in that dielectric constant (ε) between 2.0-2.2, heatThe coefficient of expansion (GTE)≤13 (× 10-6/ DEG C), hot strength/MPa >=160, Tg/ DEG C >=320.
6. positive photosensitive polyimide composition according to claim 1, is characterized in that solvent comprises the third twoAlcohol methyl ether acetate, propylene-glycol diacetate, 3-ethyoxyl-3-imines ethyl propionate, N-crassitudeOne or more in ketone, 2-heptane, 3-heptane, cyclopentanone, cyclohexanone.
CN201510996585.1A 2015-12-23 2015-12-23 Positive-working PSPI (photosensitive polyimide) composition with low CTE (coefficient of thermal expansion) and high resolution Pending CN105585847A (en)

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Publication number Priority date Publication date Assignee Title
CN111624854A (en) * 2020-04-13 2020-09-04 南京鑫达泰科技有限公司 Photosensitive semiconductor device

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