JP5920341B2 - 有機光電変換素子、その製造方法及び太陽電池 - Google Patents
有機光電変換素子、その製造方法及び太陽電池 Download PDFInfo
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- JP5920341B2 JP5920341B2 JP2013514074A JP2013514074A JP5920341B2 JP 5920341 B2 JP5920341 B2 JP 5920341B2 JP 2013514074 A JP2013514074 A JP 2013514074A JP 2013514074 A JP2013514074 A JP 2013514074A JP 5920341 B2 JP5920341 B2 JP 5920341B2
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- photoelectric conversion
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000052 poly(p-xylylene) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000447 polyanionic polymer Polymers 0.000 description 1
- 229920000323 polyazulene Polymers 0.000 description 1
- 229920001088 polycarbazole Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920000015 polydiacetylene Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000417 polynaphthalene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229940100890 silver compound Drugs 0.000 description 1
- 150000003379 silver compounds Chemical class 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000002109 single walled nanotube Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- VELSFHQDWXAPNK-UHFFFAOYSA-N tetracontacyclo[25.6.5.516,28.44,32.35,11.321,34.28,10.212,15.222,35.229,31.113,20.124,38.02,6.014,19.017,25.018,23.030,37.033,36.547,54.446,53.448,58.126,51.150,52.03,45.07,42.09,61.039,40.041,43.044,63.049,76.055,78.056,62.057,68.059,64.060,67.065,69.066,71.070,73.072,75.074,77]octaheptaconta-1,3(45),4(48),5(61),6,8,10,12,14,16,18,20,22,24(39),25,27(38),28,30,32,34(42),35(40),36,41(43),44(63),46,49(76),50(77),51,53,55(78),56(62),57,59,64,66,68,70(73),71,74-nonatriacontaene Chemical compound c12c3c4c5c6c1c1c7c8c2c2c3c3c9c4c4c5c5c%10c%11c%12c%13c%14c%15c%12c%12c%16c%17c%18c%19c%20c%21c%17c%17c%22c%21c%21c%23c%20c%20c%19c%19c%24c%18c%16c%15c%15c%24c%16c(c7c%15c%14c1c6c5%13)c8c1c2c2c3c3c(c%21c5c%22c(c%11c%12%17)c%10c4c5c93)c%23c2c%20c1c%19%16 VELSFHQDWXAPNK-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- ZGWZWRHJHVTXEL-UHFFFAOYSA-N trimethyl(thiophen-2-yl)stannane Chemical compound C[Sn](C)(C)C1=CC=CS1 ZGWZWRHJHVTXEL-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000001039 wet etching Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
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Description
2.前記一般式(1)で表される部分構造を有する化合物の数平均分子量が、15000〜50000であることを特徴とする前記1に記載の有機光電変換素子。
6.前記一般式(1)において、nが1であることを特徴とする前記1〜5のいずれかに記載の有機光電変換素子。
図1は、本発明の有機光電変換素子の構成の例を示す概略断面図である。
(一般式(1)で表される部分構造を有する化合物)
光電変換層は、p型有機半導体材料として前記一般式(1)で表される部分構造を有する化合物を含有する。
前記p型有機半導体材料は、より好ましくは、前記一般式(1)で表される構造と、前記一般式(2)で表される構造とを有する共重合体である。
本発明に係る化合物のうち、一般式(1)で表される部分構造を有する化合物は、J.Med.Chem.,1995,p1786、J.Fluorine Chem.,2004,p421、及びPhysical Organic,1967,p.909等を参考として合成することができる。
以下、本発明の一般式(1)で表される部分構造を有する化合物の合成例を示す。
本発明に係る光電変換層に用いられるn型有機半導体材料としては、特に限定されないが、例えば、フラーレン、オクタアザポルフィリン等、p型有機半導体の水素原子をフッ素原子に置換したパーフルオロ体(パーフルオロペンタセンやパーフルオロフタロシアニン等)、ナフタレンテトラカルボン酸無水物、ナフタレンテトラカルボン酸ジイミド、ペリレンテトラカルボン酸無水物、ペリレンテトラカルボン酸ジイミド等の芳香族カルボン酸無水物やそのイミド化物を骨格として含む高分子化合物等を挙げることができる。
p型有機半導体材料とn型有機半導体材料とを含有する光電変換層の形成方法としては、蒸着法、塗布法(キャスト法、スピンコート法を含む)等を例示することができる。
本発明の有機光電変換素子は、光電変換層とカソードとの間に電子輸送層を有することが好ましい。これにより、光電変換層で発生した電荷をより効率的に取り出すことが可能となる。
本発明の有機光電変換素子は、光電変換層とアノードとの間に正孔輸送層を有することが好ましい。これにより、光電変換層で発生した電荷をより効率的に取り出すことが可能となる。
本発明の有機光電変換素子は、光電変換効率の向上や、素子寿命の向上を目的に、各種中間層を素子内に有する構成としてもよい。
本発明の有機光電変換素子は、第1の電極と第2の電極を必須に有し、タンデム構成をとる場合には、さらに中間電極(電荷再結合層)を有する。
本発明の第1の電極に用いられる材料としては、例えば、インジウムチンオキシド(ITO)、AZO、FTO、SnO2、ZnO、酸化チタン等の透明金属酸化物、Ag、Al、Au、Pt等の非常に薄い金属層又は金属ナノワイヤ、カーボンナノチューブ等のナノワイヤやナノ粒子を含有する層、PEDOT:PSS、ポリアニリン等の導電性高分子材料等を用いることができる。
第2の電極は導電性材料からなる単独層であってもよいが、導電性材料に加えて、これらを保持する樹脂を併用してもよい。
また、前記図3のようなタンデム構成の場合に必要となる中間電極の材料としては、透明性と導電性を併せ持つ化合物が好ましく、前記アノードで用いたような材料(ITO、AZO、FTO、SnO2、ZnO、酸化チタン等の透明金属酸化物、Ag、Al、Au、Pt等の非常に薄い金属層又は金属ナノワイヤ、カーボンナノチューブ等のナノワイヤやナノ粒子を含有する層、PEDOT:PSS、ポリアニリン等の導電性高分子材料等)を用いることができる。
本発明において、基板は透明な基板であるが、「透明な」とは前述の電極における定義と同様である。
本発明の有機光電変換素子は、太陽光のより効率的な受光を目的として、各種の光学機能層を有していてよい。光学機能層としては、例えば、反射防止膜、マイクロレンズアレイ等の集光層、カソードで反射した光を散乱させて再度光電変換層に入射させることができるような光拡散層等を設けてもよい。
本発明に係る各々の電極、光電変換層や、正孔輸送層、電子輸送層等をパターニングする方法やプロセスには特に制限はなく、公知の手法を適宜適用することができる。
本発明の太陽電池は、上記の有機光電変換素子を有する。
〔有機光電変換素子の作製〕
(有機光電変換素子1の作製)
国際公開第2008/134492号を参考として、有機光電変換素子を作製した。
有機光電変換素子1の作製において、p型有機半導体材料を表1に記載の材料に変更した以外は同様にして有機光電変換素子2〜11を得た。なお比較化合物2は非特許文献4を参照して合成した。また、有機光電変換素子5と6は、同じポリマー(例示化合物14)であるが、合成ロットが異なり、分子量の異なる材料を有機光電変換素子としたものである。
(光電変換効率の評価)
上記封止後の有機光電変換素子に、ソーラーシミュレーター(AM1.5Gフィルタ)の100mW/cm2の強度の光を照射し、有効面積を1.0cm2にしたマスクを受光部に重ね、短絡電流密度Jsc(mA/cm2)及び開放電圧Voc(V)、曲線因子(フィルファクター)FF(%)を、同素子上に形成した4箇所の受光部についてそれぞれ測定し、平均値を求めた。また、測定されたJsc、Voc、FFから下記式1に従って光電変換効率η(%)を求めた。
光電変換効率の評価を行った有機光電変換素子を、陽極と陰極との間はオープンサーキットの状態で85℃に加熱し、ソーラシミュレーター(AM1.5G)の光を暴露し続け、初期の変換効率を100としたとき、80となるまでの時間をLT80として測定した。この値は、大きいほど有機光電変換素子の耐久性が良好であることを示す。
〔有機光電変換素子の作製〕
(有機光電変換素子2’の作製)
例1で作製した有機光電変換素子2と同様の素材及び組成を用いて、以下のような順層型の有機光電変換素子を作製した。
上記有機光電変換素子2’の作製において、p型有機半導体材料として、比較化合物2の代わりに例示化合物31を用い、他は同様にして順層型の有機光電変換素子11’を作製した。
(光電変換効率の評価)
上記作製した有機光電変換素子2’、11’及び例1で作製した有機光電変換素子2、11について、例1と同様に、光電変換効率及び有機光電変換素子の耐久性評価を評価した。
〔有機光電変換素子の作製〕
(有機光電変換素子1”の作製)
例1で作製した有機光電変換素子1を作製する際に、正孔輸送層の塗布を大気下ではなく、グローブボックス内(GB内)でそのまま行うことで、有機光電変換素子1”を作製した。
例1で作製した有機光電変換素子2を作製する際に、正孔輸送層の塗布を大気下ではなく、グローブボックス内でそのまま行うことで、有機光電変換素子2”を作製した。
例1で作製した有機光電変換素子4,7,9、11を作製する際に、正孔輸送層の塗布を大気下ではなく、グローブボックス内でそのまま行うことで、有機光電変換素子4”、7”、9”、11”を作製した。有機光電変換素子4”、7”、9”、11”ではグローブボックス内のような非常に乾燥した環境下でも用意した5枚の有機光電変換素子中、5枚とも正孔輸送層を弾かずに製膜することができた。
上記作製した有機光電変換素子1”、2”、4”、7”、9”、11”及び例1で作製した有機光電変換素子1、2、4、7、9、11について、例1と同様に、光電変換効率及び有機光電変換素子の耐久性評価を評価した。
11 基板、
12 第1の電極、
13 第2の電極、
14 光電変換層、
14’ 第1の光電変換層、
15 電荷再結合層、
16 第2の光電変換層、
17 正孔輸送層、
18 電子輸送層。
Claims (13)
- 透明な基板上に、透明な第1の電極、p型有機半導体材料とn型有機半導体材料とを含有する光電変換層、及び第2の電極をこの順に有する有機光電変換素子であって、該光電変換層が、該p型有機半導体材料として下記一般式(1)で表される部分構造を有する化合物を含有することを特徴とする有機光電変換素子。
- 前記一般式(1)で表される部分構造を有する化合物の数平均分子量が、15000〜50000であることを特徴とする請求項1に記載の有機光電変換素子。
- 前記一般式(1)において、R1がXと同じ原子を表すことを特徴とする請求項1又は2に記載の有機光電変換素子。
- 前記一般式(1)において、Xがフッ素原子を表すことを特徴とする請求項1〜3のいずれか1項に記載の有機光電変換素子。
- 前記p型有機半導体材料が、前記一般式(1)で表される構造と、さらに下記一般式(2)で表される構造とを有する共重合体であることを特徴とする請求項1〜4のいずれか1項に記載の有機光電変換素子。
- 前記一般式(1)において、nが1であることを特徴とする請求項1〜5のいずれか1項に記載の有機光電変換素子。
- 前記一般式(1)において、R2が炭素数8〜20のアルキル基を表すことを特徴とする請求項1〜6のいずれか1項に記載の有機光電変換素子。
- 前記一般式(1)において、R2が直鎖のアルキル基を表すことを特徴とする請求項1〜7のいずれか1項に記載の有機光電変換素子。
- 前記一般式(1)で表される部分構造が、R2が炭素数8以上のアルキル基を表す部分構造と、R3が炭素数8未満のアルキル基又は水素原子を表す部分構造とをともに含むことを特徴とする請求項1〜8のいずれか1項に記載の有機光電変換素子。
- 透明な基板上に、透明な第1の電極、p型有機半導体材料とn型有機半導体材料とを含有する光電変換層、及び第2の電極をこの順に有する有機光電変換素子であって、該光電変換層が、該p型有機半導体材料として下記一般式(1)で表される部分構造と、下記一般式(2)で表される構造とを有する共重合体を含有することを特徴とする有機光電変換素子。
- 透明な基板上に、透明な第1の電極、p型有機半導体材料とn型有機半導体材料とを含有する光電変換層、及び第2の電極をこの順に有する有機光電変換素子であって、該光電変換層が、該p型有機半導体材料として下記9〜14で表される部分構造を有する化合物のいずれかを含有することを特徴とする有機光電変換素子。
- 請求項1〜11のいずれか1項に記載の有機光電変換素子の光電変換層を、製膜中及び製膜後に酸素及び水分に曝すことなく製造することを特徴とする有機光電変換素子の製造方法。
- 前記第1の電極がカソードであり、前記第2の電極がアノードである請求項1〜11のいずれか1項に記載の有機光電変換素子を具備することを特徴とする太陽電池。
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