JP5099527B2 - Method for producing a thin film pattern that absorbs near infrared light - Google Patents
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- 239000010409 thin film Substances 0.000 title claims description 47
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000010438 heat treatment Methods 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 14
- 239000000758 substrate Substances 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 8
- 238000000059 patterning Methods 0.000 claims description 6
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000001771 vacuum deposition Methods 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 28
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 24
- 238000010521 absorption reaction Methods 0.000 description 18
- 229930192474 thiophene Natural products 0.000 description 16
- 238000000862 absorption spectrum Methods 0.000 description 14
- 125000005577 anthracene group Chemical group 0.000 description 7
- 239000000178 monomer Substances 0.000 description 6
- 230000001678 irradiating effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 239000013638 trimer Substances 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- SGBAEQQAROREQJ-UHFFFAOYSA-N 2,5-di(anthracen-1-yl)thiophene Chemical compound c1cc(sc1-c1cccc2cc3ccccc3cc12)-c1cccc2cc3ccccc3cc12 SGBAEQQAROREQJ-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 238000006619 Stille reaction Methods 0.000 description 2
- -1 anthracene-substituted thiophene Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- UWGKQMNCIGZMBH-UHFFFAOYSA-N BrC1=CC=C(S1)C1=CC=CC2=CC3=CC=CC=C3C=C12 Chemical compound BrC1=CC=C(S1)C1=CC=CC2=CC3=CC=CC=C3C=C12 UWGKQMNCIGZMBH-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Description
本発明は、ドライプロセスにより、太陽電池素子等に用いる近赤外光吸収性の薄膜パターンを作製する技術に関する。 The present invention relates to a technique for producing a near-infrared light-absorbing thin film pattern used for a solar cell element or the like by a dry process.
従来から、固体基板上への薄膜のパターン形成の方法としては、フォトリソグラフィー方法や、放射線重合等の方法がその代表的なものとして知られている。このうちのリソグラフィー方法は、光架橋剤や光反応基を持つモノマー・ポリマー溶剤（フォトレジスト）を基板表面（例えばウェハ）に薄く塗布し、マスキングした後に、光（光架橋剤や光反応基が反応できる波長の光）照射することにより、部分的にフォトレジストの溶解度を変化させ（架橋反応による不溶化または結合切断による可溶化）、所定のパターニングを焼き付け転写する方法である。（特許文献１、非特許文献１，２）
一方、このような固体基板上の薄膜パターンを利用する技術分野の一つに太陽電池素子がある。太陽電池において高効率を達成するためには、自然光に含まれる１ｅＶ以下の近赤外領域の低エネルギーを有効利用することが不可欠である。そのため、太陽電池素子においては、このような近赤外光を吸収することのできる材質から成る薄膜をパターニングする製造技術が必要とされる。
しかし、リソグラフィー法による薄膜のパターン形成方法で近赤外光を吸収する薄膜を作成するには、近赤外光を吸収する化合物に光架橋剤を混合したり、光反応基を結合させたりする必要があり、パターンを形成するのに照射波長を選択したりしないといけないという問題があった。（特許文献２，３）
Conventionally, as a method for forming a pattern of a thin film on a solid substrate, a photolithography method, a method such as radiation polymerization, and the like are known as typical ones. Among these lithography methods, a monomer / polymer solvent (photoresist) having a photocrosslinking agent or a photoreactive group is thinly applied to a substrate surface (for example, a wafer), masked, and then light (photocrosslinker or photoreactive group is present). This is a method in which the solubility of the photoresist is partially changed by irradiation (light having a wavelength capable of reaction) (insolubilization by cross-linking reaction or solubilization by bond breaking), and predetermined patterning is baked and transferred. (
On the other hand, there is a solar cell element as one of the technical fields using such a thin film pattern on a solid substrate. In order to achieve high efficiency in a solar cell, it is indispensable to effectively use low energy in the near infrared region of 1 eV or less contained in natural light. Therefore, in the solar cell element, a manufacturing technique for patterning a thin film made of a material capable of absorbing such near infrared light is required.
However, in order to create a thin film that absorbs near-infrared light by a lithography method for forming a thin film pattern, a photo-crosslinking agent is mixed with a compound that absorbs near-infrared light, or a photoreactive group is bonded. There is a problem that it is necessary to select an irradiation wavelength in order to form a pattern. (
本発明は、ドライプロセスで作成した薄膜を紫外光照射して、加熱処理するだけで、近赤外光を吸収する薄膜をパターニングして固定化できる方法を提供することを目的とする。 An object of the present invention is to provide a method capable of patterning and immobilizing a thin film that absorbs near-infrared light simply by irradiating the thin film prepared by a dry process with ultraviolet light and performing a heat treatment.
本発明者は、上記目的を、薄膜の材質として、以下の光反応性基を有するオリゴチオフェンを用いることにより達成した。固体基板上に形成した当該オリゴチオフェン蒸着膜に対し紫外線照射し、その後加熱することで、近赤外光を吸収する薄膜をパターニングすることが可能となる。より詳細には、本発明は、固体基板上に近赤外光を吸収する薄膜のパターニングを形成する、以下の方法を提供するものである。
下記の式で表されるオリゴチオフェンの薄膜を固体基板上に真空蒸着により形成し、当該基板に紫外光を照射後、加熱処理することにより、固体基板上に近赤外光を吸収する薄膜のパターニングを形成する方法。
A thin film of oligothiophene represented by the following formula is formed on a solid substrate by vacuum deposition, and after the substrate is irradiated with ultraviolet light, heat treatment is performed to form a thin film that absorbs near infrared light on the solid substrate. A method of forming patterning.
以上、説明したように、上記光反応性基を有するオリゴチオフェンを用いれば、ドライプロセスで作成した薄膜を紫外光照射して加熱処理するだけで、近赤外光を吸収する薄膜を簡便にパターニング形成できる。 As described above, if the oligothiophene having the photoreactive group is used, a thin film that absorbs near-infrared light can be easily patterned simply by irradiating the thin film prepared by the dry process with ultraviolet light and heat-treating it. Can be formed.
以下、下記の実施例に基づいて、本発明を更に詳細に説明する。 Hereinafter, the present invention will be described in more detail based on the following examples.
１．実験方法
実験に用いたオリゴチオフェンは、以下に示す構造の物質である。両末端、あるいは片末端にアリール基を有するオリゴチオフェンを用いた。
1. Experimental Method Oligothiophene used in the experiment is a substance having the following structure. Oligothiophene having an aryl group at both ends or at one end was used.
両末端にアントラセンを有するチオフェン３量体（ｎ＝３）は、テトラキス（トリフェニルホスフィン）パラジウム（０）を触媒として、２，５−ビス（トリブチル錫）チオフェンと２−ブロモ−５−アンスリルチオフェンのスティルカップリング反応により合成した（以下の式（３−１））。片末端にアントラセンを有するチオフェン３量体（ｎ＝３）は、テトラキス（トリフェニルホスフィン）パラジウム（０）を触媒として、５−メチル−５‘−トリブチル錫−２，２’−ビチオフェンと２−ブロモ−５−アンスリルチオフェンのスティルカップリング反応により合成した（以下の式（３−２））。薄膜は真空蒸着法により石英基板上に作成した。得られた薄膜を大気下で紫外光を一定時間照射した後、真空下、一定温度、一定時間加熱し、室温まで冷却して大気下で紫外−可視−近赤外吸収スペクトルを測定した。 A thiophene trimer (n = 3) having anthracene at both ends is obtained by using tetrakis (triphenylphosphine) palladium (0) as a catalyst and 2,5-bis (tributyltin) thiophene and 2-bromo-5-anthryl. It was synthesized by a thiophene Stille coupling reaction (the following formula (3-1)). A thiophene trimer having an anthracene at one end (n = 3) is obtained by using tetrakis (triphenylphosphine) palladium (0) as a catalyst and 5-methyl-5′-tributyltin-2,2′-bithiophene and 2- It was synthesized by a Stille coupling reaction of bromo-5-anthrylthiophene (the following formula (3-2)). A thin film was formed on a quartz substrate by vacuum evaporation. The obtained thin film was irradiated with ultraviolet light for a certain period of time in the atmosphere, then heated in vacuum at a certain temperature for a certain period of time, cooled to room temperature, and an ultraviolet-visible-near infrared absorption spectrum was measured in the atmosphere.
２．実験結果
最初に、オリゴチオフェン薄膜を大気下で紫外光照射した時の吸収スペクトル変化について調べた。両末端がアントラセンで置換されたチオフェン１量体（ｎ＝１）薄膜の吸収スペクトルを図１に示す。紫外光を５分間照射することにより、３．２ｅＶ付近の吸収が減少する。更に、紫外光照射すると、照射時間の増加とともに、吸収が徐々に減少することが観測された。この結果は、２，５−ジアンスリルチオフェン薄膜を紫外光照射することにより、アントラセン基同士が２量化反応を起こしていることを示唆している。
2. Experimental results First, we investigated the change in absorption spectrum when an oligothiophene thin film was irradiated with ultraviolet light in the atmosphere. FIG. 1 shows an absorption spectrum of a thiophene monomer (n = 1) thin film in which both ends are substituted with anthracene. Irradiation with ultraviolet light for 5 minutes reduces the absorption near 3.2 eV. Furthermore, it was observed that when ultraviolet light was irradiated, the absorption gradually decreased as the irradiation time increased. This result suggests that anthracene groups cause a dimerization reaction by irradiating a 2,5-dianthrylthiophene thin film with ultraviolet light.
次に、紫外光照射した２，５−ジアンスリルチオフェン薄膜を真空下、一定温度で１０分間加熱した後の吸収スペクトル変化を図２に示す。加熱温度の増加とともに、４．８ｅＶの吸収の減少とともに、吸収の幅が広がり、吸収の裾の低エネルギーへの拡がりが観測された。加熱前の黄色の薄膜が、加熱後、褐色に変化していることから、バンドギャップが減少していることを示唆している。２量化したアントラセンが、加熱することにより開環してネットワーク化したためと考えられる。 Next, FIG. 2 shows the change in absorption spectrum after heating the ultraviolet light irradiated 2,5-dianthrylthiophene thin film at a constant temperature for 10 minutes under vacuum. As the heating temperature increased, the absorption range increased with a decrease in absorption of 4.8 eV, and the absorption tail was observed to spread to lower energy. The yellow thin film before heating changes to brown after heating, suggesting that the band gap is reduced. This is probably because dimerized anthracene was opened and networked by heating.
それに対して、紫外光を照射しないで両末端をアントラセン置換したチオフェン１量体薄膜を真空下、一定温度で１０分間加熱した後の吸収スペクトル変化を図３に示す。３００℃で１０分間加熱すると、吸収がほとんどなくなり、更に加熱時間を増やすと吸収が消えてしまい、薄膜が基板から脱離しているものと思われる。 In contrast, FIG. 3 shows a change in absorption spectrum after heating a thiophene monomer thin film in which both ends are anthracene-substituted without irradiation with ultraviolet light at a constant temperature for 10 minutes under vacuum. When heated at 300 ° C. for 10 minutes, the absorption is almost lost, and when the heating time is further increased, the absorption disappears and the thin film seems to be detached from the substrate.
これらの結果は、アントラセンで置換したオリゴチオフェン薄膜を加熱する前に、紫外光照射によりアントラセンの２量化反応を起こさせると、その後、薄膜を加熱することにより、紫外光照射した箇所は赤外光を吸収する薄膜に変化して固定化され、紫外光照射していない箇所は薄膜が脱離することで、簡便に赤外光を吸収する薄膜をパターニング形成できることを示している。 These results show that when an anthracene dimerization reaction is caused by irradiation with ultraviolet light before heating the oligothiophene thin film substituted with anthracene, the thin film is then heated so that the portion irradiated with ultraviolet light becomes infrared light. This indicates that a thin film that absorbs infrared light can be easily formed by patterning by removing the thin film at a portion that is changed to a thin film that absorbs and is fixed and is not irradiated with ultraviolet light.
次に、両末端のアントラセンの間に結合しているチオフェンの数の効果について調べた。両末端がアントラセンで置換されたチオフェン５量体（ｎ＝５）薄膜の紫外光照射、ならびに加熱後の吸収スペクトル変化を図４に示す。薄膜に紫外光を照射することにより、３ｅＶの吸収が減少し、吸収の裾の広がりが観測された。その後、真空下５００℃で１０分間、加熱することにより、４．６ｅＶの吸収の減少とともに、吸収の幅が広がり、裾が近赤外領域まで広がることが観測された。図４の結果は、チオフェンの数の増加とともに、吸収の裾の広がりが大きくなることを示唆している。 Next, the effect of the number of thiophenes bonded between anthracene at both ends was examined. FIG. 4 shows changes in absorption spectrum after irradiation with ultraviolet light and heating of a thiophene pentamer (n = 5) thin film in which both ends are substituted with anthracene. By irradiating the thin film with ultraviolet light, the absorption of 3 eV decreased, and the spread of the bottom of the absorption was observed. After that, by heating at 500 ° C. for 10 minutes under vacuum, it was observed that the absorption width widened and the skirt widened to the near infrared region as the absorption decreased by 4.6 eV. The results in FIG. 4 suggest that the broadening of the absorption tail increases as the number of thiophenes increases.
次に、オリゴチオフェンの両末端の置換基効果について調べた。両末端がナフチル基で置換されたチオフェン４量体（ｎ＝４）薄膜への光照射、ならびに加熱後の吸収スペクトル変化を図５に示す。紫外光を１時間照射しても、吸収強度はほとんど変化しなかった。更に、加熱しても吸収強度が加熱温度の増加とともに減少するだけで、吸収の裾の広がりは観測されなかった。 Next, the effect of substituents at both ends of oligothiophene was examined. FIG. 5 shows changes in absorption spectrum after light irradiation and heating to a thiophene tetramer (n = 4) thin film substituted at both ends with a naphthyl group. Even when irradiated with ultraviolet light for 1 hour, the absorption intensity hardly changed. Furthermore, even when heated, the absorption intensity only decreased as the heating temperature increased, and no broadening of the absorption tail was observed.
それに対して、片方がメチル基、もう一方がアントラセン基で置換したチオフェン３量体（ｎ＝３）薄膜への紫外光照射、ならびに加熱後の吸収スペクトル変化を図６に示す。紫外光照射により、２．８ｅＶの吸収の減少、ならびに、その後、一定温度で１０分間加熱することにより、吸収の幅が広がり、裾の低エネルギー側への広がりが観測された。オリゴチオフェンの両末端にアントラセンが置換されている薄膜より、裾の広がりが少ないことが分かった。 On the other hand, FIG. 6 shows ultraviolet light irradiation to a thiophene trimer (n = 3) thin film substituted with a methyl group on one side and an anthracene group on the other side, and an absorption spectrum change after heating. A decrease in absorption of 2.8 eV due to irradiation with ultraviolet light, and a subsequent heating at a constant temperature for 10 minutes increased the width of absorption and the spread of the tail toward the lower energy side was observed. It was found that the tail spread is less than that of the thin film where anthracene is substituted on both ends of oligothiophene.
これらの結果から、薄膜を紫外光照射後に加熱することにより、近赤外光を吸収する薄膜に変換するには、オリゴチオフェンの片末端、あるいは両末端にアントラセン基が置換されている必要があることが分かった。更に、オリゴチオフェンへのアントラセンの置換数、ならびにチオフェンの結合数によって、薄膜の吸収波長を制御できることも明らかとなった。 From these results, it is necessary to substitute an anthracene group at one or both ends of oligothiophene to convert the thin film into a thin film that absorbs near-infrared light by heating after irradiation with ultraviolet light. I understood that. Furthermore, it has been clarified that the absorption wavelength of the thin film can be controlled by the number of anthracene substitutions to oligothiophene and the number of thiophene bonds.
本発明による近赤外光吸収性の薄膜のパターニングの技術は、薄膜太陽電池、可視光ＥＬや紫外光センサー、光記録材料、薄膜トランジスターなどの素子を作成する用途に用いることができる。 The near-infrared light-absorbing thin film patterning technique according to the present invention can be used for applications such as thin film solar cells, visible light EL, ultraviolet light sensors, optical recording materials, and thin film transistors.
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