JP6971214B2 - 有機半導体デバイス - Google Patents
有機半導体デバイス Download PDFInfo
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- JP6971214B2 JP6971214B2 JP2018203682A JP2018203682A JP6971214B2 JP 6971214 B2 JP6971214 B2 JP 6971214B2 JP 2018203682 A JP2018203682 A JP 2018203682A JP 2018203682 A JP2018203682 A JP 2018203682A JP 6971214 B2 JP6971214 B2 JP 6971214B2
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- 239000004065 semiconductor Substances 0.000 title description 26
- 150000001875 compounds Chemical class 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 239000002800 charge carrier Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- -1 alkyl cyanide Chemical compound 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 230000031700 light absorption Effects 0.000 claims description 5
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 5
- 150000001350 alkyl halides Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 66
- 239000000758 substrate Substances 0.000 description 23
- 239000000463 material Substances 0.000 description 17
- 239000002019 doping agent Substances 0.000 description 7
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000000370 acceptor Substances 0.000 description 6
- 239000006096 absorbing agent Substances 0.000 description 5
- 230000004927 fusion Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 230000002745 absorbent Effects 0.000 description 4
- 239000002250 absorbent Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000005693 optoelectronics Effects 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- 0 *C(c1c(*)c(*)c(*)[n]1)=C1N=C(*)C(*)=C1* Chemical compound *C(c1c(*)c(*)c(*)[n]1)=C1N=C(*)C(*)=C1* 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- GZEFZLXJPGMRSP-UHFFFAOYSA-N 37,38,39,40-tetrazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1(37),2,4,6,8,10,12(39),13,15,17,19,21,23,25,27,29,31,33,35-nonadecaene Chemical compound c1ccc2c3cc4[nH]c(cc5nc(cc6[nH]c(cc(n3)c2c1)c1ccccc61)c1ccccc51)c1ccccc41 GZEFZLXJPGMRSP-UHFFFAOYSA-N 0.000 description 1
- NBOCQTNZUPTTEI-UHFFFAOYSA-N 4-[4-(hydrazinesulfonyl)phenoxy]benzenesulfonohydrazide Chemical compound C1=CC(S(=O)(=O)NN)=CC=C1OC1=CC=C(S(=O)(=O)NN)C=C1 NBOCQTNZUPTTEI-UHFFFAOYSA-N 0.000 description 1
- 229920003026 Acene Polymers 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 229920004933 Terylene® Polymers 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- JYNZIOFUHBJABQ-UHFFFAOYSA-N allyl-{6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl-}-methyl-amin Chemical compound C=1OC2=CC(OCCCCCCN(C)CC=C)=CC=C2C=1C1=CC=C(Br)C=C1 JYNZIOFUHBJABQ-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000003574 free electron Substances 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 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
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- PMJMHCXAGMRGBZ-UHFFFAOYSA-N subphthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(=N3)N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C3=N1 PMJMHCXAGMRGBZ-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
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Description
I II
ここで、
R1およびR2,および/またはR6およびR7は、それぞれ一緒に、S,O,NまたはPから選択された少なくとも1つのヘテロ原子を有する複素環の5員環または6員環、または単素環の、さらなる融合の無い6員環を形成し、またもしR1とR2またはR6とR7が複素環基または単素環基を全く形成しない場合は、これらは互いに独立した1つのHまたは他の基の1つであり、
R3,R4,およびR5は、互いに独立したH、またはアリール,アルキル,フッ化アルキルまたは部分フッ化アルキル,不飽和アルキルから選択された1つの基であり、
R8とR9は互いに独立して、ハロゲン,アルキル,フッ化あるいは部分フッ化アルキル,アルケニル,アルキニル,アルコキシ,アリール,またはヘテロアリールから選択したものである。
ここでR1およびR2,および/またはR6およびとR7は、それぞれ一緒に、S,O,NまたはPから選択された少なくとも1つのヘテロ原子を有する複素環の5員環または6員環、または単素環の、さらなる融合の無い6員環を形成し、またもしR1とR2またはR6とR7が複素環基または単素環基を全く形成しない場合は、これらは互いに独立した1つの酸素または他の基の1つであり、
R3,R4,およびR5は、互いに独立して、水素または、アリール,アルキル,フッ化アルキル,不飽和アルキルから選択した1つの基であり、
R8とR9は互いに独立した、ハロゲン,アルキル,アルケニル,アルキニル,アルコキシ,アリール,またはヘテロアリールから選択したものである。
上記の式の*で示された部分は、一般式IまたはIIのR1,R2,R6,またはR7への結合部位を表す。X,Y,およびZは、互いに独立して、O,S,Se,または水素またはアルキルから選択されたR18を有するN−R18から選択され、R10〜R17は、互いに独立して、水素、アルキル,アルキニル,アルケニル,O−アルキル,S−アルキル,アリール,ヘテロアリール,ハロゲン化アルキル,シアン化アルキルから選択されている。
0. 担体,基板
1.基板側接続部(Grundkontakt)、通常透明
2. p層(複数でもよい)
3. i層(複数でもよい)
4. n層(複数でもよい)
5.上側接続部(Deckkontakt)
1つの実施例においては、透明な基板側接続部ITO(M),フラーレンC60(I)の層,化合物1のフラーレンC60(I)との1:1混合層,p−ドーピングされたDi−NPBおよびNDP9のホール輸送層,および金の上側コンタクト部を有するガラス基板上の試料からなるMIPデバイスが生成され、ここでこの化合物1とC60との混合物は、110℃の基板温度で堆積されている。
1
実施例1で説明したようなMIPが、異なる基板温度50℃,70℃,90℃,および110℃毎に製造されている。図4のグラフ表示から、上記の充填因子および効率が基板温度の上昇と共に同様に上昇することが分る。
Claims (11)
- 層系の少なくとも1つの層が光吸収層であり、前記光吸収層が以下の一般式IまたはIIの化合物を含む、1つの層系を有する太陽電池であって、
R8とR9は互いに独立した、ハロゲン,アルキル,フッ化あるいは部分フッ化アルキル,アルケニル,アルキニル,アルコキシ,アリール,またはヘテロアリールから選択したものであり、
R1とR2、およびR6とR7は、それぞれ一緒に、SおよびOから選択された少なくとも1つのヘテロ原子を有する複素環の5員環を形成し、またはR1とR2、およびR6とR7は、さらなる融合の無い単素環の6員環を形成する、
ことを特徴とする太陽電池。 - 請求項1に記載の一般式IまたはIIの化合物において、単素環上の残りの4つの結合部位の少なくとも3つは非置換のままであり、前記一般式IまたはIIの化合物は、ドナー-アクセプター-ヘテロ接合のドナーである、請求項1に記載の太陽電池。
- R4はアリール,アルキル,フッ化または部分フッ化アルキル,または不飽和アルキルから選択された1つの基である、請求項1乃至4のいずれか1項に記載の太陽電池。
- R4はフッ化または部分フッ化アルキルから選択された1つの基である、請求項1乃至5のいずれか1項に記載の太陽電池。
- 前記一般式Iの化合物の大きさは、300〜1500g/molのモル質量を有する、請求項1乃至6のいずれか1項に記載の太陽電池。
- 前記一般式IまたはIIの少なくとも1つの化合物に加えて、前記層系には電荷担体輸送層が存在しており、当該電荷担体輸送層は、ドーピングされているか,部分的にドーピングされているか,またはドーピングされていない、請求項1乃至8のいずれか1項に記載の太陽電池。
- 前記光吸収層が混合層として構成され、当該混合層がバルクヘテロ接合である、請求項9に記載の太陽電池。
- 前記太陽電池が、タンデムセル,またはマルチセルとして構成されている、請求項1乃至10のいずれか1項に記載の太陽電池。
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