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J. Semicond. > 2013, Volume 34 > Issue 6 > 063003

SEMICONDUCTOR MATERIALS

The effects of cure temperature history on the stability of polyimide films

Wenguo Ning1, 2, Heng Li1, 2, Chunsheng Zhu1, 2, Le Luo1, , Dong Chen3 and Zhenzhen Duan3

+ Author Affiliations

 Corresponding author: Luo Le, Email:leluo@mail.sim.ac.cn

DOI: 10.1088/1674-4926/34/6/063003

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Abstract: The effects of cure temperature history on the stability of hinged structure poly (4, 4-oxydiphenylene pyromellitimide) (PMDA-ODA) polyimide were studied by dynamic mechanical analysis. The polyimide films were cured under different curing conditions and peeled off by substrate etching. It was found that a proper cure time and temperature ramp rate improves the stability in terms of higher glass transition temperature. Ninety minutes at 375℃ or 200℃ is a beneficial high glass transition temperature. The temperature ramp rate should be between 2℃/min and 10℃/min, which is neither too high nor too low.

Key words: curing of polymerspolyimidestabilizationDMA

Polyimides have many applications due to their excellent thermal, electrical and mechanical properties. In electronic packaging with multi-level interconnections, such as wafer-level chip scale packaging, polyimides are widely used as dielectric materials. The related processes include the first polyimide layer curing, copper trace electroplating and the second polyimide layer curing. However, one concern in the application of polyimides is stability, because polyimides have to go through a cure or reflow process several times at relatively high temperatures in the fabrication process of multi-level interconnections.

The curing process is critical for polyimides. Russell studied the effects of curing temperature on crosslinking by measuring the dynamic mechanical analysis (DMA) properties, and indicated that crosslinking occurs above 300 ℃ for the polyimide: AFRIOOB. The samples were heated to isotherms from 275 to 400 ℃ at a rate of 2 ℃/min over a duration from 1 to 16 h. It was found that crosslinking via the reverse Diels-Alder reaction occurs up to 350 ℃[1].

Rich studied the effects of curing on the removal of solvents and the development of chemical crosslinks[2]. Sasaki performed a detailed cure study on oligomers by staged heating to final cure temperatures of 370, 400, 420, and 450 ℃, and DMA showed an increase with temperature and a decrease in the drop of storage modulus (E) with increasing post-cure temperature[3]. Many researchers have focused on the stress measurements of the polyimide during the cure process.

The stability of polyimides can be examined by dynamic mechanical analysis. The stability of electron beam irradiated polyimides has been examined by measuring the glass relaxations of polyimides through dynamical mechanical analysis[4]. The stability of proton beam irradiated polyimides has also been reported[5].

However, very few efforts have been made on the effects of curing temperature history on the stability of polyimides. In general, the polyimide cure process compromises many factors. In electronic packaging with multi-level interconnections, the stability is especially of concern. To our knowledge, there are no published reports on the influence of curing temperature on the above mentioned properties of PMDA-ODA film. These properties will help understand the effects of the curing process, such as the ramp rate of the temperature, curing time etc, on the stability of the polyimides, and thus the results will help fabricate electronic packaging with highly reliable multi-level interconnections.

In this paper, the effects of the curing process on the stability of the polyimide film (PMDA-ODA) were studied using DMA. DMA is the most accurate technique for the study of the glass relaxation and relaxation processes in polyimides. The tests focus on the shift in the glass relaxation peak due to different curing processes. The goal of this research is to determine the effects of the curing process on the stability of polyimide films.

To prepare the polyimide films, polyimidic solution (HD4100, HD MicroSystems) was coated onto 4 inch glass substrates.The spin speed was 2000 rpms and the spin time was 30 s. Then the coated substrate was soft baked on hot plate at 90 ℃ for 100 s and 100 ℃ for 100 s. After that, the coated substrate was cured under 11 different curing conditions in nitrogen atmosphere in a reflow oven (SRO-702/704), as shown in Table 1.

Table  1.  Cure processes.
DownLoad: CSV  | Show Table

These may be divided into three groups, namely A, D, G, H and I, which differ with the heat treatment time at 375 ℃ (30, 60, 90, 120 and 150 min), then A, E, F, J and K, which differ by the time at 200 ℃ (again 30, 60, 90, 120 and 150 min), and finally A, B, and C, which differ in the rate of heating (2, 5-7 and 10 ℃/min). The evaluation of the effect of changing curing times at one temperature was carried out having fixed the time in the other curing step.

After curing, the polyimide and glass substrates were diced into 35 × 10 mm2 rectangular samples, and the polyimide film was then peeled off by HF/HCl mixed acid etching. The volume ratio was 10 : 1. Finally, the films were washed in deionized water to remove the acid. The thickness of the films was about 10.0 μm. The fabrication process is shown in Fig. 1.

Figure  1.  The fabrication process of polyimide film.

The dynamic mechanical analysis of the polyimide film was performed with film: tension modeled by a DMA Q 800 dynamic mechanical analyzer (TA Instruments, Inc., USA). The temperature range was from 40 to 400 ℃, and the polyimide film samples were heated at a ramp rate of 3 ℃/min in air at a frequency of 1 Hz. The glass transition temperature is defined as the high temperature peak in the tan δ curves[6].

The typical DMA results are shown with three curves: storage modulus, loss modulus, and tan δ. As the polyimide specimen goes through its glass transition, the storage modulus reduces and tan δ passes a peak because the sample becomes less stiff and molecular reorganization of the relaxation induces less elastic behavior.

Generally, there are three relaxation processes: the low temperature and medium temperature relaxation processes are defined as the β1 and β2 sub glass relaxation processes, and the high temperature relaxation is an α-relaxation process[7]. The β1 and β2 relaxation processes correspond to sub-glass transition temperatures, while the α relaxation is the glass transition.

As shown in Fig. 2, the tan δ curve exhibits two peaks at about 150 ℃ and 300 ℃, indicating two relaxations. The high temperature peak results from the glass relaxation occurring in the polyimide film. The temperature is in accordance with the properties of pristine polyimide.

Figure  2.  DMA curves of polyimide cured under curing process A.

The low temperature peak may originate either from the contribution of adsorbed water molecules or β2 sub-glass relaxation[8-11], which was induced by the rotation or oscillation of phenyl groups within polyimide's diamine moiety. Typically, this relaxation was reported to be between 125 ℃ and 190 ℃.

The effects of the cure temperature history on the Tg were focused on in this work.

Polyimide is synthesized by a two-step reaction, as shown in Fig. 3. In this work, PMDA-ODA polyamic acid (PAA) solution is coated onto the substrate. The second step reaction occurs during the cure process.

Figure  3.  Polyimide synthesization.

Chemical structure changes occur during the cure process, which affect the Tg of polymers in two ways: chain flexibility and substituent effects[12]. The Tg decreases with the flexibility of the backbone of the polymer chain. The flexibility of the chain segments is determined by the degree of freedom with which different segments along the chain backbone can rotate around the covalent bonds[13]. As shown in Fig. 1, during the cure process the degree of freedom of the segments decreases as new covalent bonds form. Consequently, the chain flexibility decreases and Tg increases. Meanwhile, the cure degree increases as the covalent bonds form. Hence, Tg is related to cure degree: Tg increases with cure degree before cure completion.

The effect of temperature ramp rate on Tg is shown in Fig. 4. It is apparent that neither the high rate nor the low rate can get a higher glass transition temperature, which means a proper rate between 2 and 10 ℃/min is imperative to get a higher glass transition temperature. In this work, a ramp rate of 5 to 7 ℃/min results in the highest glass transition temperature. However, more work needs to be done to find out the best ramp rate.

Figure  4.  Effects of ramp rate on glass relaxation temperature.

The ramp rate related properties may be attributed to an incomplete reaction, or residual solvent or photoproducts, which could act as plasticizers. A higher ramp rate means a shorter curing time, which will lead to an incomplete reaction, which means a lower cure degree and lower glass transition temperature.

Meanwhile, the solvent may not evaporate completely at a low ramp rate for relatively thick films. For relatively thin films, the solvent could evaporate completely at a low ramp rate, as shown in Fig. 5(a), but for relatively thick films, a low ramp rate may form a cured film at the top first, which prevents the evaporation of the solution at the bottom. Thus, the solvent may not evaporate completely at a low ramp rate for relatively thick films, as shown in Fig. 5(b). The incomplete cured films result in a lower cure degree and lower glass transition temperature. Thus, a proper temperature ramp rate is beneficial for high glass transition temperature.

Figure  5.  Evaporation of the solution.

The effects of time at 200 ℃ and 375 ℃ on the glass transition temperature are shown in Fig. 6.

Figure  6.  Effects of time at 200 ℃ and 375 ℃ on glass relaxation temperature.

According to Fig. 6, for different times at 200 ℃, 90 min at 200 ℃ (Process F) results in the highest glass transition temperature. For different times at 375 ℃, 120 min at 375 ℃ (Process H) results in the highest glass transition temperature. 90 min at 375 ℃ (Process G) results in a very close glass transition temperature. Besides, it also reveals that the glass transition temperature is more sensitive to constant temperature time at 375 ℃ than that at 200 ℃.

The results can be explained by the relationship of cure degree and Tg. At the beginning, Tg increases as the cure time at 200 ℃ or 375 ℃ increases until the cure degree reaches 100%. The glass transition temperature shifts to higher temperature as the cure degree increases.

But after complete reaction, the longer time at 200 ℃ or 375 ℃ results in a Tg that is no higher. Even worse, the relatively high temperature breaks the covalent bonds. Two types of bond may be broken: the covalent bonds formed during the curing process, or the covalent bonds along the backbone chain. In the former case, the chain flexibility increases and thus the Tg decreases. In the second case, the phenomenon can be explained by the Fox-Flory equation[14]:

TG(MN)=TGKMN,

(1)

where TG(MN) is the glass transition temperature of a polymer characterized by the average numerical mass, MN, TG is the glass transition temperature of the infinite length of the polymeric chain (with the same repeating unit), and K is a constant. The glass transition temperature shifts to a lower temperature as the average numerical mass decreases.

The effects of cure temperature history on the stability of hinged structure poly (4, 4-oxydiphenylene pyromellitimide) (PMDA-ODA) polyimide were studied by dynamic mechanical analysis. The polyimide films were cured under different curing conditions and peeled off by substrate etching. It was found that a proper cure time and temperature ramp rate improves the stability, in terms of higher glass transition temperature. 90 min at 375 ℃ or 200 ℃ is beneficial for high glass relaxation. The temperature ramp rate should be between 2 ℃/min and 10 ℃/min, which is neither too high nor too low.

Acknowledgements: The authors would like to extend their heartfelt gratitude to Dr. Cheng Yuanrong, Dr. Yang Jun and Dr. Pan Qilin of the Department of Materials Science, Fudan University, Shanghai, China for the DMA analysis and useful discussions. The authors would also like to express sincere gratitude to M. A Kehui Guo for English editing.


[1]
Russell J D, Kardos J L. Crosslinking characterization of a polyimide:AFR700B. Polymer Composites, 1997, 18(5):595 doi: 10.1002/(ISSN)1548-0569
[2]
Rich D C, Sichel E K, Cebe P. Curing study of a preimidized photosensitive polyimide. Polymer Eng Sci, 1996, 36(17):2179 doi: 10.1002/(ISSN)1548-2634
[3]
Sasaki T, Yokota R. Synthesis and properties of an addition-type imide oligomer having pendent phenylethynyl groups:investigation of curing behavior. High Performance Polymers, 2006, 18(2):199 doi: 10.1177/0954008306058269
[4]
Kang P H, Jeon Y K, Jeun J P, et al. Effect of electron beam irradiation on polyimide film. Journal of Industrial and Engineering Chemistry, 2008, 14(5):672 doi: 10.1016/j.jiec.2008.03.004
[5]
Artiaga R, Chipara M, Stephens C P, et al. Dynamical mechanical analysis of proton beam irradiated polyimide. Nuclear Instruments and Methods in Physics Research Section B:Beam Interactions with Materials and Atoms, 2005, 236(1-4):432 doi: 10.1016/j.nimb.2005.04.013
[6]
Chen C, Qin W, Huang X. Synthesis and characterization of novel polyimides derived from 1, 4-bis (4-aminophenoxymethylene) cyclohexane (BAMC) and two aromatic dianhydrides. Journal of Macromolecular Science, Part B, 2008, 47(4):783 doi: 10.1080/00222340802119273
[7]
Li F, Ge J J, Honigfirt P S, et al. Dianhydride architectural effects on the relaxation behaviors and thermal and optical properties of organo-soluble aromatic polyimide films. Polymer, 1999, 40(18):4987 doi: 10.1016/S0032-3861(98)00721-6
[8]
Mircea I C. On an anomalous kinetic in irradiated polymers around the glass transition temperature. Nuclear Instruments and Methods in Physics Research Section B:Beam Interactions with Materials and Atoms, 1997, 131(1-4):180 doi: 10.1016/S0168-583X(97)00340-6
[9]
Chipara M, Benson R, Chipara M, et al. ESR investigations on irradiated polystyrene. Nuclear Instruments and Methods in Physics Research Section B:Beam Interactions with Materials and Atoms, 2003, 208(0):390 http://cat.inist.fr/?aModele=afficheN&cpsidt=14952935
[10]
Pireaux J J, Gregoire C, Caudano R, et al. Electron-induced vibrational spectroscopy——a new and unique tool to unravel the molecular-structure of polymer surfaces. Langmuir, 1991, 7(11):2433 doi: 10.1021/la00059a006
[11]
Chern Y T, H C Shiue. High subglass transition temperatures and low dielectric constants of polyimides derived from 4, 9-bis (4-aminophenyl) diamantane. Chem Mater, 1998, 10(1):210 doi: 10.1021/cm970341k
[12]
American Society of Metals. Characterization and failure analysis of plastics. Ohio:ASM International, 2003:119 http://cityofmaterials.asminternational.org/content/ASM/StoreFiles/06978G_Frontmatter.pdf
[13]
Gowariker V R, Viswanathan N V, Sreedhar J. Polymer science. New York:John Wiley & Sons 1986:164
[14]
Fox T G, Flory P J. The glass temperature and related properties of polystyrene:influence of molecular weight. J Polymer Sci, 1954, 14(75):315 doi: 10.1002/pol.1954.120147514
Fig. 1.  The fabrication process of polyimide film.

Fig. 2.  DMA curves of polyimide cured under curing process A.

Fig. 3.  Polyimide synthesization.

Fig. 4.  Effects of ramp rate on glass relaxation temperature.

Fig. 5.  Evaporation of the solution.

Fig. 6.  Effects of time at 200 ℃ and 375 ℃ on glass relaxation temperature.

Table 1.   Cure processes.

[1]
Russell J D, Kardos J L. Crosslinking characterization of a polyimide:AFR700B. Polymer Composites, 1997, 18(5):595 doi: 10.1002/(ISSN)1548-0569
[2]
Rich D C, Sichel E K, Cebe P. Curing study of a preimidized photosensitive polyimide. Polymer Eng Sci, 1996, 36(17):2179 doi: 10.1002/(ISSN)1548-2634
[3]
Sasaki T, Yokota R. Synthesis and properties of an addition-type imide oligomer having pendent phenylethynyl groups:investigation of curing behavior. High Performance Polymers, 2006, 18(2):199 doi: 10.1177/0954008306058269
[4]
Kang P H, Jeon Y K, Jeun J P, et al. Effect of electron beam irradiation on polyimide film. Journal of Industrial and Engineering Chemistry, 2008, 14(5):672 doi: 10.1016/j.jiec.2008.03.004
[5]
Artiaga R, Chipara M, Stephens C P, et al. Dynamical mechanical analysis of proton beam irradiated polyimide. Nuclear Instruments and Methods in Physics Research Section B:Beam Interactions with Materials and Atoms, 2005, 236(1-4):432 doi: 10.1016/j.nimb.2005.04.013
[6]
Chen C, Qin W, Huang X. Synthesis and characterization of novel polyimides derived from 1, 4-bis (4-aminophenoxymethylene) cyclohexane (BAMC) and two aromatic dianhydrides. Journal of Macromolecular Science, Part B, 2008, 47(4):783 doi: 10.1080/00222340802119273
[7]
Li F, Ge J J, Honigfirt P S, et al. Dianhydride architectural effects on the relaxation behaviors and thermal and optical properties of organo-soluble aromatic polyimide films. Polymer, 1999, 40(18):4987 doi: 10.1016/S0032-3861(98)00721-6
[8]
Mircea I C. On an anomalous kinetic in irradiated polymers around the glass transition temperature. Nuclear Instruments and Methods in Physics Research Section B:Beam Interactions with Materials and Atoms, 1997, 131(1-4):180 doi: 10.1016/S0168-583X(97)00340-6
[9]
Chipara M, Benson R, Chipara M, et al. ESR investigations on irradiated polystyrene. Nuclear Instruments and Methods in Physics Research Section B:Beam Interactions with Materials and Atoms, 2003, 208(0):390 http://cat.inist.fr/?aModele=afficheN&cpsidt=14952935
[10]
Pireaux J J, Gregoire C, Caudano R, et al. Electron-induced vibrational spectroscopy——a new and unique tool to unravel the molecular-structure of polymer surfaces. Langmuir, 1991, 7(11):2433 doi: 10.1021/la00059a006
[11]
Chern Y T, H C Shiue. High subglass transition temperatures and low dielectric constants of polyimides derived from 4, 9-bis (4-aminophenyl) diamantane. Chem Mater, 1998, 10(1):210 doi: 10.1021/cm970341k
[12]
American Society of Metals. Characterization and failure analysis of plastics. Ohio:ASM International, 2003:119 http://cityofmaterials.asminternational.org/content/ASM/StoreFiles/06978G_Frontmatter.pdf
[13]
Gowariker V R, Viswanathan N V, Sreedhar J. Polymer science. New York:John Wiley & Sons 1986:164
[14]
Fox T G, Flory P J. The glass temperature and related properties of polystyrene:influence of molecular weight. J Polymer Sci, 1954, 14(75):315 doi: 10.1002/pol.1954.120147514
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    Wenguo Ning, Heng Li, Chunsheng Zhu, Le Luo, Dong Chen, Zhenzhen Duan. The effects of cure temperature history on the stability of polyimide films[J]. Journal of Semiconductors, 2013, 34(6): 063003. doi: 10.1088/1674-4926/34/6/063003
    W G Ning, H Li, C S Zhu, L Luo, D Chen, Z Z Duan. The effects of cure temperature history on the stability of polyimide films[J]. J. Semicond., 2013, 34(6): 063003. doi: 10.1088/1674-4926/34/6/063003.
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    Received: 09 October 2012 Revised: 27 December 2012 Online: Published: 01 June 2013

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      Wenguo Ning, Heng Li, Chunsheng Zhu, Le Luo, Dong Chen, Zhenzhen Duan. The effects of cure temperature history on the stability of polyimide films[J]. Journal of Semiconductors, 2013, 34(6): 063003. doi: 10.1088/1674-4926/34/6/063003 ****W G Ning, H Li, C S Zhu, L Luo, D Chen, Z Z Duan. The effects of cure temperature history on the stability of polyimide films[J]. J. Semicond., 2013, 34(6): 063003. doi: 10.1088/1674-4926/34/6/063003.
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      Wenguo Ning, Heng Li, Chunsheng Zhu, Le Luo, Dong Chen, Zhenzhen Duan. The effects of cure temperature history on the stability of polyimide films[J]. Journal of Semiconductors, 2013, 34(6): 063003. doi: 10.1088/1674-4926/34/6/063003 ****
      W G Ning, H Li, C S Zhu, L Luo, D Chen, Z Z Duan. The effects of cure temperature history on the stability of polyimide films[J]. J. Semicond., 2013, 34(6): 063003. doi: 10.1088/1674-4926/34/6/063003.

      The effects of cure temperature history on the stability of polyimide films

      DOI: 10.1088/1674-4926/34/6/063003
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      Project supported by the National Science and Technology Major Project (No. 2009ZX02025-1)

      the National Science and Technology Major Project 2009ZX02025-1

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      • Corresponding author: Luo Le, Email:leluo@mail.sim.ac.cn
      • Received Date: 2012-10-09
      • Revised Date: 2012-12-27
      • Published Date: 2013-06-01

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