JP5805438B2 - 新規化合物、光電変換材料及び光電変換素子 - Google Patents
新規化合物、光電変換材料及び光電変換素子 Download PDFInfo
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- JP5805438B2 JP5805438B2 JP2011132271A JP2011132271A JP5805438B2 JP 5805438 B2 JP5805438 B2 JP 5805438B2 JP 2011132271 A JP2011132271 A JP 2011132271A JP 2011132271 A JP2011132271 A JP 2011132271A JP 5805438 B2 JP5805438 B2 JP 5805438B2
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Images
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
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- Photovoltaic Devices (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Description
しかし、有機系太陽電池の光電変換効率は低いものが多いため、高光電変換効率化が課題となっている。
また本発明の別の目的は、上記新規化合物を用いた光電変換材料、光電変換層、光電変換素子及び有機薄膜太陽電池を提供することにある。
R3〜R6は、各々独立に、水素原子、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基、−NRR’、炭素原子数1〜20のアルキル基、炭素原子数6〜20のアリール基、炭素原子数1〜20のアルコキシ基、炭素原子数6〜20のアリールオキシ基、又は隣接する2つのR3〜R6がそれぞれ連結して脂肪族環、芳香環若しくは複素環を形成する基を表し、
R7は、水素原子又は炭素原子数1〜20のアルキル基を表し、
Xは−CRR’−、−S−、−O−又は−NR−を表し、
Arは、1,4−フェニレン基、ナフタレン−2,6−ジイル基、ナフタレン−1,4−ジイル基、ビフェニル−4,4’−ジイル基又はテルフェニル−4,4”−ジイル基を表し、これらの基は更にハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基、−NRR’、炭素原子数1〜20のアルキル基、炭素原子数6〜20のアリール基、炭素原子数1〜20のアルコキシ基又は炭素原子数6〜20のアリールオキシ基で置換されていてもよく、Ar及びR1を構成する炭素原子は互いに連結して環構造を形成してもよく、
R及びR’は、各々独立に、水素原子、炭素原子数1〜20のアルキル基又は炭素原子数6〜20のアリール基を表す。)
本発明の新規化合物は、上記一般式(1)で表わされる。
上記一般式(1)におけるR1及びR2で表される炭素原子数1〜40の一価の置換基としては、置換基を有してもよい炭素原子数1〜40のアルキル基、又は置換基を有してもよい炭素原子数4〜40のπ共役基が挙げられる。
置換基を有してもよい炭素原子数1〜40のアルキル基の中でも、炭素原子数1〜10のアルキル基が好ましい。
置換基を有してもよい炭素原子数4〜40のπ共役基として好ましくは、炭素原子数6〜40の下記一般式(2)で表される基が挙げられる。
また、上記一般式(1)で表わされる化合物の中でも、光電変換素子の変換効率向上の効果が高い点から、Xが、−S−又は−O−である化合物が好ましい。
また、上記一般式(1)で表わされる化合物の中でも、光電変換素子の変換効率向上の効果が高い点から、Arが、1,4−フェニレン基、ナフタレン−2,6−ジイル基又はナフタレン−1,4−ジイル基である化合物が好ましい。
本発明の光電変換材料は、(A)本発明の上記一般式(1)で表わされる化合物を、(B)p型有機半導体材料及び(C)n型有機半導体材料に含有させたものである。
(A)上記一般式(1)で表される化合物:好ましくは0.5〜5重量%、更に好ましくは1〜3重量%
(B)p型有機半導体材料:好ましくは25〜70重量%、更に好ましくは35〜60重量%
(C)n型有機半導体材料::好ましくは25〜70重量%、更に好ましくは35〜60重量%
次に、本発明の光電変換層について説明する。本発明の光電変換層は、本発明の光電変換材料を製膜して得られる。製膜方法に関しては特に限定するものではないが、例えば、蒸着法、物理気相成長法(PVD)、化学気相成長法(CVD)、原子層堆積法(ALD)、原子層エピタキシー法(ALE)、分子線エピタキシー法(MBE)、気相エピタキシー法(VPE)、スパッタ法、プラズマ重合法等のドライプロセス;ディップコート法、キャスト法、エアーナイフコート法、カーテンコート法、ローラーコート法、ワイヤーバーコート法、グラビアコート法、スピンコート法、LB法、オフセット印刷法、スクリーン印刷法、フレキソ印刷法、ディスペンサ印刷法、インクジェット法、エクストルージョンコート法等のウェットプロセスによって支持体上に塗膜形成する方法が挙げられる。
本発明の光電変換素子は、本発明の光電変換層を少なくとも一つ有する以外は、従来公知の光電変換素子と同様に構成される。例えば、図1(a)を例にとって示すと、支持体1、電極2、電荷移動層3、光電変換層4、及び電極5が順次積層された構造を有する。また、図1(b)に示すように電荷移動層3を除いた構造であってもよく、図1(c)に示すように電荷移動層6を更に有する構造であってもよい。
4−(ジフェニルアミノ)ベンズアルデヒド(20mmol)、2−ベンゾチアゾールアセトニトリル(20mmol)、及び無水ピペラジン(4mmol)を溶媒(42g)に溶解させ60℃で6時間加熱攪拌を行った。冷却後、析出した固体をろ別し、再度ジメチルアセトアミド/クロロホルム/エタノールにて再結晶を行い、化合物No.3(14.8mmol)を得た。得られた結晶が目的物(化合物No.3)であることは、各種分析で確認した。結果を[表1]〜[表4]に示す。
対応するアルデヒド化合物及び活性メチレン化合物を用いて、合成例1と同様の手法で[表1]に記載の化合物を合成した。合成結果及び各種分析結果を[表1]〜[表4]に示す。
図1(c)に示す層構成を有する光電変換素子を、以下の手順で作製した。
電極2としてITOが150nm成膜してあるガラス基板(支持体1)をIPA煮沸洗浄及びUV−オゾン洗浄した後、電荷移動層3としてPEDOT:PSS(3,4−エチレンジオキシチオフェン:ポリスチレンスルホン酸)を20nmスピンコート法により成膜し、100℃、10分の条件で減圧乾燥した。1,2−ジクロロベンゼン2mLに(A)上記一般式(1)で表される化合物として化合物No.3を3mg、(B)p型有機半導体としてP3HTを50mg、及び(C)n型有機半導体としてPCBMを50mg溶解させて、実施例1の光電変換材料を調製した。調製した光電変換材料を、スピンコート法により成膜し、100℃、30分の条件で減圧乾燥して光電変換層4とした。こうして得られた有機薄膜層の上に、メタルマスクを用いてLiF0.5nm(電荷移動層6)、及びアルミニウム100nm(電極5)を逐次真空蒸着成膜して、実施例1の光電変換素子を作製した。
こうして得られた光電変換素子に対し、エアマス1.5G、100mW/cm2の擬似太陽光をITO電極側から照射して光電変換特性(効率(%))を測定した。結果を[表5]に示す。
上記実施例1の光電変換素子の作製において、(A)〜(C)成分及び組成比を〔表5〕に示すように変更する以外は、実施例1と同様にして、実施例2〜8の光電変換素子を作製した。また、実施例1と同様の操作で、実施例2〜8の光電変換素子の光電変換特性(効率(%))を測定した。結果を[表5]に示す。
上記実施例1の光電変換素子の作製において、(A)成分として、化合物No.3の代わりに、下記の比較化合物1又は2を用いるか、化合物No.3を用いない以外は実施例1と同様の操作で、比較例1〜5の光電変換素子を作製し、実施例1と同様の操作で、比較例1〜5の光電変換素子の光電変換特性(効率(%))を測定した。結果を[表5]に示す。
従って、上記一般式(1)で表わされる、本発明の新規化合物を添加した光電変換材料は、光電変換素子に有用である。
2 電極
3 電荷移動層
4 光電変換層
5 電極
6 電荷移動層
Claims (6)
- 下記一般式(1)で表される化合物。
R3〜R6は、各々独立に、水素原子、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基、−NRR’、炭素原子数1〜20のアルキル基、炭素原子数6〜20のアリール基、炭素原子数1〜20のアルコキシ基、炭素原子数6〜20のアリールオキシ基、又は隣接する2つのR3〜R6がそれぞれ連結して脂肪族環、芳香環若しくは複素環を形成する基を表し、
R7は、水素原子又は炭素原子数1〜20のアルキル基を表し、
Xは−S−、−O−又は−NR−を表し、
Arは、1,4−フェニレン基を表し、これらの基は更にハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基、−NRR’、炭素原子数1〜20のアルキル基、炭素原子数6〜20のアリール基、炭素原子数1〜20のアルコキシ基又は炭素原子数6〜20のアリールオキシ基で置換されていてもよく、Ar及びR1を構成する炭素原子は互いに連結して環構造を形成してもよく、
R及びR’は、各々独立に、水素原子、炭素原子数1〜20のアルキル基又は炭素原子数6〜20のアリール基を表し、
Ar及びR1を構成する炭素原子が互いに連結して環構造を形成する場合、その環構造は、カルバゾール環又はインドリン環であり、R 2 は、炭素原子数6〜40の下記一般式(2)で表わされる基を表し、
Ar及びR1を構成する炭素原子が互いに連結して環構造を形成しない場合、R1及びR2の少なくとも一方は、炭素原子数6〜40の下記一般式(2)で表される基を表す。)
- (A)下記一般式(1−1)で表される化合物、(B)p型有機半導体材料及び(C)n型有機半導体材料を含んでなる光電変換材料。
R3〜R6は、各々独立に、水素原子、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基、−NRR’、炭素原子数1〜20のアルキル基、炭素原子数6〜20のアリール基、炭素原子数1〜20のアルコキシ基、炭素原子数6〜20のアリールオキシ基、又は隣接する2つのR3〜R6がそれぞれ連結して脂肪族環、芳香環若しくは複素環を形成する基を表し、
R7は、水素原子又は炭素原子数1〜20のアルキル基を表し、
Xは−CRR’−、−S−、−O−又は−NR−を表し、
Arは、1,4−フェニレン基、ナフタレン−2,6−ジイル基、ナフタレン−1,4−ジイル基、ビフェニル−4,4’−ジイル基又はテルフェニル−4,4”−ジイル基を表し、これらの基は更にハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基、−NRR’、炭素原子数1〜20のアルキル基、炭素原子数6〜20のアリール基、炭素原子数1〜20のアルコキシ基又は炭素原子数6〜20のアリールオキシ基で置換されていてもよく、Ar及びR1を構成する炭素原子は互いに連結して環構造を形成してもよく
、 R及びR’は、各々独立に、水素原子、炭素原子数1〜20のアルキル基又は炭素原子数6〜20のアリール基を表す。)
1)〜(B−9)から選ばれる基を1〜4個組み合わせた基である。)
- 上記(B)p型有機半導体材料がポリ(3−ヘキシルチオフェン)であり、上記(C)n型有機半導体材料がフラーレン誘導体である請求項2に記載の光電変換材料。
- 請求項2又は3に記載の光電変換材料を製膜して得られる光電変換層。
- 請求項4に記載の光電変換層を有してなる光電変換素子。
- 請求項5に記載の光電変換素子を有してなる有機薄膜太陽電池。
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