JP5845937B2 - 有機光電変換素子 - Google Patents
有機光電変換素子 Download PDFInfo
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- JP5845937B2 JP5845937B2 JP2012020236A JP2012020236A JP5845937B2 JP 5845937 B2 JP5845937 B2 JP 5845937B2 JP 2012020236 A JP2012020236 A JP 2012020236A JP 2012020236 A JP2012020236 A JP 2012020236A JP 5845937 B2 JP5845937 B2 JP 5845937B2
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- 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
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Photovoltaic Devices (AREA)
Description
Y1およびY2は、それぞれ独立して、−O−、−NR2−、−S−、−C(R3)=C(R4)−、または−N=C(R5)−を表し、
Z1およびZ2は、それぞれ独立して、−C(R6)2−、−C(=O)−、−C(=S)−、−C(=C(R7)2)−を表し、
R1〜R7は、それぞれ独立して、水素原子(H)、ハロゲン原子、置換されたもしくは非置換の、炭素原子数1〜24のアルキル基、炭素原子数1〜24のフッ化アルキル基、炭素原子数3〜20のシクロアルキル基、炭素原子数3〜20のフッ化シクロアルキル基、炭素原子数1〜24のアルコキシ基、炭素原子数1〜24のフッ化アルコキシ基、炭素原子数1〜24のアルキルチオ基、炭素原子数1〜24のフッ化アルキルチオ基、炭素原子数6〜30のアリール基、炭素原子数6〜30のフッ化アリール基、炭素原子数1〜20のヘテロアリール基、または炭素原子数1〜20のフッ化ヘテロアリール基を表す。
本発明の一形態は、下記一般式1で表される部分構造(ジインデノピラジン環構造、ジペンタレノピラジン環構造)を有する共役系高分子化合物を光電変換層に含む有機光電変換素子に関する。
一般式2中、D1およびD2は、それぞれ独立して、硫黄原子(S)を含む複素芳香族環からなるドナー性ユニット(群)(より詳しくは、ドナー性複素芳香族環基および/またはドナー性複素縮合芳香族環基)を表す。ここで、ドナー性ユニットD1およびD2は1種のみを単独で使用してもよいし、2種以上を併用してもよく、D1とD2とは同一であってもよいし、異なっていてもよい。また、D1およびD2が一つの部分構造中に複数個存在する(p=2〜4またはr=2〜4)場合には、D1およびD2は、それぞれ、同じであってもあるいは異なるものであってもよい。
本形態の有機光電変換素子は、第一の電極および第二の電極を必須に含む。第一の電極および第二の電極は、各々、陽極または陰極として機能する。本明細書において、「第一の」および「第二の」とは、陽極または陰極としての機能を区別するための用語である。したがって、第一の電極が陽極として機能し、第二の電極が陰極として機能する場合もあるし、逆に、第一の電極が陰極として機能し、第二の電極が陽極として機能する場合もある。上述したように、光電変換層14で生成されるキャリア(正孔・電子)は、電極間を移動し、正孔は陽極11へ、電子は陰極12へと到達する。なお、本発明においては主に正孔が流れる電極を陽極と呼び、主に電子が流れる電極を陰極と呼ぶ。また、タンデム構成をとる場合には電荷再結合層(中間電極)を用いることでタンデム構成を達成することができる。さらに、電極が透光性を有するものであるか否かという機能面から、透光性を有する電極を透明電極と呼び、透光性のない電極を対電極と呼び分ける場合もある。順層構成の場合、通常、陽極は透光性のある透明電極であり、陰極は透光性のない対電極である。
1) 第1電極(陰極)ITO, 第2電極(陽極)銀
2) 第1電極(陰極)PEDOT:PSS, 第2電極(陽極)銀
3) 第1電極(陰極)ITO, 第2電極(陽極)銅
4) 第1電極(陰極)PEDOT:PSS, 第2電極(陽極)金
5) 第1電極(陰極)ITO, 第2電極(陽極)PEDOT:PSS
等を挙げることができる。
光電変換層は、光起電力効果を利用して光エネルギーを電気エネルギーに変換する機能を有する。本形態の有機光電変換素子は、光電変換層に、n型有機半導体および上述の本発明の共役系高分子化合物をp型有機半導体として必須に含む点に特徴を有する。これらの光電変換材料に光が吸収されると、励起子が発生し、これがpn接合界面において、正孔と電子とに電荷分離される。
本発明の有機光電変換素子は、必要に応じて基板を含みうる。基板は、電極を塗布方式で形成する場合における、塗布液の被塗布部材としての役割を有する。
本形態の有機光電変換素子は、必要に応じて正孔輸送層を含みうる。正孔輸送層は、正孔を輸送する機能を有し、かつ電子を輸送する能力が著しく小さい(例えば、正孔の移動度の10分の1以下)という性質を有する。正孔輸送層は、光電変換層と陽極との間に設けられ、正孔を陽極へと輸送しつつ、電子の移動を阻止することで、電子と正孔とが再結合するのを防ぐことができる。
本形態の有機光電変換素子は、必要に応じて電子輸送層を含みうる。電子輸送層は、電子を輸送する機能を有し、かつ正孔を輸送する能力が著しく小さいという性質を有する。電子輸送層は、光電変換層と陰極との間に設けられ、電子を陰極へと輸送しつつ、正孔の移動を阻止することで、電子と正孔とが再結合するのを防ぐことができる。
図3で示すような、2以上の光電変換層を有するタンデム型(多接合型)の有機光電変換素子において、光電変換層間には、電荷再結合層(中間電極)が配置される。
本形態の有機光電変換素子は、上記の各部材(各層)の他に、光電変換効率の向上や、素子の寿命の向上のために、他の部材(他の層)をさらに設けてもよい。その他の部材としては、例えば、正孔注入層、電子注入層、励起子ブロック層、UV吸収層、光反射層、波長変換層などが挙げられる。また、上層に偏在した金属酸化物微粒子をより安定にするため等にシランカップリング剤等の層を設けてもよい。さらに本発明の光電変換層に隣接して金属酸化物の層を積層してもよい。
上述の本形態の有機光電変換素子の製造方法は特に制限はなく、従来公知の手法を適宜参照することにより製造することができる。以下、図2に示すような逆層型の有機光電変換素子の製造方法を例に挙げて、本形態の有機光電変換素子の好ましい製造方法を説明する。ただし、当該製造方法における各工程は、逆層型の有機光電変換素子のみならず、図1に示すような順層型の有機光電変換素子や、図3に示すようなタンデム型の製造に適用可能である。
本発明の他の形態によれば、上述の有機光電変換素子を有する太陽電池が提供される。本形態の有機光電変換素子は、優れた耐久性を有し、十分な光電変換効率を達成することができるため、これを発電素子とする太陽電池に好適に使用されうる。
[例示化合物3の合成]
国際公開2008−134492号パンフットの記載を参考に、以下のようにして逆層型の有機光電変換素子を作製した。
PET基板上に、第一の電極(陰極)としてインジウムスズ酸化物(ITO)透明導電膜150nm堆積したもの(シート抵抗12Ω/square cm2)を、通常のフォトリソグラフィ技術と湿式エッチングとを用いて10mm幅を2枚用意し、次いでパターニングし、第一の電極を形成した。パターン形成した第一の電極を、界面活性剤と超純水による超音波洗浄、超純水による超音波洗浄の順で洗浄後、窒素ブローで乾燥させ、最後に紫外線オゾン洗浄を行った。これ以降は基板をグローブボックス中に持ち込み、窒素雰囲気下で作業した。
なおこの正孔輸送を塗布する際、用意しておいた2枚(2セット)のうち1枚を窒素雰囲気下(GB内)で塗布し、1枚はGB内にて塗布し、もう1枚は大気中に取出して素子化を行った。なお塗布時の大気の温度・湿度は23℃65%であった。
光電変換層の形成において、p型有機半導体として比較化合物2(非特許文献5に基づいて合成)をそれぞれ用いたことを除いては、上記比較例1と同様の方法で、逆層型の有機光電変換素子を作製した。
光電変換層の形成において、p型有機半導体として下記表1に記載の化合物をそれぞれ用いたことを除いては、上記比較例1と同様の方法で、逆層型の有機光電変換素子を作製した。
[化合物P(電子輸送材料)の合成]
下記反応により、化合物Pを合成した。
PET基板上に、第一の電極(陽極)としてインジウムスズ酸化物(ITO)透明導電膜150nm堆積したもの(シート抵抗12Ω/square cm2)を、通常のフォトリソグラフィ技術と湿式エッチングとを用いて10mm幅にパターニングし、第一の電極を形成した。パターン形成した第一の電極を、界面活性剤と超純水による超音波洗浄、超純水による超音波洗浄の順で洗浄後、窒素ブローで乾燥させ、最後に紫外線オゾン洗浄を行った。次いで、正孔輸送層として、導電性高分子及びポリアニオンからなるPEDOT−PSS(CLEVIOS(登録商標) P VP AI 4083、ヘレオス株式会社製、導電率1×10−3S/cm)を2.0質量%で含むイソプロパノール溶液を調製し、乾燥膜厚が約30nmになるように、基板を65℃に調温したブレードコーターを用いて塗布乾燥した。その後、120℃の温風で20秒間加熱処理して、正孔輸送層を上記第一の電極上に製膜した。これ以降は基板をグローブボックス中に持ち込み、窒素雰囲気下で作業した。まず、窒素雰囲気下で上記基板を120℃で3分間加熱処理した。
上記実施例1〜9および比較例1〜2で得た有機光電変換素子のうち、それぞれGB内で塗布した場合と、耐久に取出して塗布した場合の比較を行った。
正孔輸送層を発電層上に形成する際に弾くことなくに塗布することができた回数を記載した。好ましくは3回以上、より好ましくは4回以上弾かずに塗布できる。
(開放電圧、曲線因子、および光電変換効率の評価)
上記実施例1〜9および比較例1〜2で得た有機光電変換素子を、それぞれエポキシ樹脂とガラスキャップとで封止した。これにソーラーシミュレーター(AM1.5Gフィルタ)を用いて100mW/cm2の強度の光を照射し、有効面積を1cm2にしたマスクを受光部に重ね、IV特性を評価することで、短絡電流密度Jsc(mA/cm2)、開放電圧Voc(V)、および曲線因子FF測定した。得られたJsc、Voc、およびFFの値から、下記式1に従って光電変換効率η[%]を算出した。結果を表1に示す。
上記実施例1〜9および比較例1〜2について、逆層型の有機光電変換素子の作製をそれぞれ5回ずつ試みた。そして、光電変換層上に正孔輸送層を塗布する際に、光電変換層上で有機溶剤系PEDOT:PSSの分散液に含まれる親水系溶媒が光電変換層上で弾かれることなく、良好に正孔輸送層が形成された回数により製膜性を評価した。結果を表1に示す。
上記実施例1〜9および比較例1〜2で得た各有機光電変換素子を、温度80℃、湿度80%に保持した容器内に保存し、定期的に取りだしてIV特性を測定し、初期の光電変換効率を100として、初期の効率の80%まで低下した時間をLT80[時間]として評価した。LT80の値が大きいほど、耐久性が良好であることを意味する。結果を表1に示す。
11 陽極、
12 陰極、
14 光電変換層、
14a 第1の光電変換層、
14b 第2の光電変換層、
25 基板、
26 正孔輸送層、
27 電子輸送層、
38 電荷再結合層。
Claims (11)
- 第一の電極と、
第二の電極と、
前記第一の電極および前記第二の電極の間に存在する、n型有機半導体およびp型有機半導体を含む光電変換層と、
を有し、
前記p型有機半導体は、下記一般式1で表される部分構造を有する共役系高分子化合物を含む、有機光電変換素子;
Y1およびY2は、それぞれ独立して、−O−、−NR2−、−S−、−C(R3)=C(R4)−、または−N=C(R5)−を表し、
Z1およびZ2は、それぞれ独立して、−C(R6)2−、−C(=O)−、−C(=S)−、−C(=C(R7)2)−を表し、
R1〜R7は、それぞれ独立して、水素原子(H)、ハロゲン原子、置換されたもしくは非置換の、炭素原子数1〜24のアルキル基、炭素原子数1〜24のフッ化アルキル基、炭素原子数3〜20のシクロアルキル基、炭素原子数3〜20のフッ化シクロアルキル基、炭素原子数1〜24のアルコキシ基、炭素原子数1〜24のフッ化アルコキシ基、炭素原子数1〜24のアルキルチオ基、炭素原子数1〜24のフッ化アルキルチオ基、炭素原子数6〜30のアリール基、炭素原子数6〜30のフッ化アリール基、炭素原子数1〜20のヘテロアリール基、または炭素原子数1〜20のフッ化ヘテロアリール基を表す。 - 前記一般式1において、X1およびX2がそれぞれ独立して−C(R1)=である、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、Y1およびY2がそれぞれ独立して−S−である、請求項1または2に記載の有機光電変換素子。
- 前記一般式1において、Z1およびZ2がそれぞれ独立して−C(R6)2−である、請求項1〜3のいずれか1項に記載の有機光電変換素子。
- 前記一般式1を含む共役系高分子が、下記一般式2で表される部分構造を有する、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2において、Aで表わされるアクセプターユニットが、下記一般式3Aまたは一般式3Bで表わされ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;
R2〜R5およびR8〜R11は、それぞれ独立して、水素原子(H)、ハロゲン原子(F、Cl、Br、もしくはI)、置換されたもしくは非置換の、炭素原子数1〜24のアルキル基、炭素原子数1〜24のフッ化アルキル基、炭素原子数3〜20のシクロアルキル基、炭素原子数3〜20のフッ化シクロアルキル基、炭素原子数1〜24のアルコキシ基、炭素原子数1〜24のフッ化アルコキシ基、炭素原子数1〜24のアルキルチオ基、炭素原子数1〜24のフッ化アルキルチオ基、炭素原子数6〜30のアリール基、炭素原子数6〜30のフッ化アリール基、炭素原子数1〜20のヘテロアリール基、または炭素原子数1〜20のフッ化ヘテロアリール基を表す。 - 前記一般式3A、前記一般式3Bにおいて、Y3〜Y5が−S−であることを特徴とする、請求項6に記載の有機光電変換素子。
- 前記共役系高分子化合物の数平均分子量は、10,000〜100,000である、請求項1〜7のいずれか1項に記載の有機光電変換素子。
- 前記第一の電極は透明電極であり、
前記第二の電極は対電極であり、
前記光電変換層と前記第二の電極との間に、さらに正孔輸送層を有する、請求項1〜8のいずれか1項に記載の有機光電変換素子。 - 請求項1〜9のいずれか1項に記載の有機光電変換素子を有する、太陽電池。
- 下記一般式1で表される部分構造を有する共役系高分子化合物(ただし、X 1 およびX 2 がともに−C(R 1 )=であり、Y 1 およびY 2 がともに−C(R 3 )=C(R 4 )−であり、かつ、Z 1 およびZ 2 がともに−C(=C(R 7 ) 2 )−であるものを除く)。
Y1およびY2は、それぞれ独立して、−O−、−NR2−、−S−、−C(R3)=C(R4)−、または−N=C(R5)−を表し、
Z1およびZ2は、それぞれ独立して、−C(R6)2−、−C(=O)−、−C(=S)−、−C(=C(R7)2)−を表し、
R1〜R7は、それぞれ独立して、水素原子(H)、ハロゲン原子(F、Cl、Br、もしくはI)、置換されたもしくは非置換の、炭素原子数1〜24のアルキル基、炭素原子数1〜24のフッ化アルキル基、炭素原子数3〜20のシクロアルキル基、炭素原子数3〜20のフッ化シクロアルキル基、炭素原子数1〜24のアルコキシ基、炭素原子数1〜24のフッ化アルコキシ基、炭素原子数1〜24のアルキルチオ基、炭素原子数1〜24のフッ化アルキルチオ基、炭素原子数6〜30のアリール基、炭素原子数6〜30のフッ化アリール基、炭素原子数1〜20のヘテロアリール基、または炭素原子数1〜20のフッ化ヘテロアリール基を表す。
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