JP7108870B2 - 光電変換材料および光電変換素子 - Google Patents
光電変換材料および光電変換素子 Download PDFInfo
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- JP7108870B2 JP7108870B2 JP2018149762A JP2018149762A JP7108870B2 JP 7108870 B2 JP7108870 B2 JP 7108870B2 JP 2018149762 A JP2018149762 A JP 2018149762A JP 2018149762 A JP2018149762 A JP 2018149762A JP 7108870 B2 JP7108870 B2 JP 7108870B2
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- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical class [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000001181 organosilyl group Chemical class [SiH3]* 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920000548 poly(silane) polymer Chemical class 0.000 description 1
- 229920000768 polyamine Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000003967 siloles Chemical group 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 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
- 150000003536 tetrazoles Chemical class 0.000 description 1
- QKTRRACPJVYJNU-UHFFFAOYSA-N thiadiazolo[5,4-b]pyridine Chemical compound C1=CN=C2SN=NC2=C1 QKTRRACPJVYJNU-UHFFFAOYSA-N 0.000 description 1
- CRUIOQJBPNKOJG-UHFFFAOYSA-N thieno[3,2-e][1]benzothiole Chemical group C1=C2SC=CC2=C2C=CSC2=C1 CRUIOQJBPNKOJG-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003577 thiophenes Chemical class 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
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- H01L31/02—Details
- H01L31/0232—Optical elements or arrangements associated with the device
- H01L31/02322—Optical elements or arrangements associated with the device comprising luminescent members, e.g. fluorescent sheets upon the device
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Description
有機半導体材料は、シリコンなどの従来の無機半導体材料にはない物性、機能等を備える。このため、例えば非特許文献1に記載のように、新しい半導体デバイスまたは電子機器を実現し得る半導体材料として、近年有機半導体材料が活発に研究されている。
Xは、水素原子、重水素原子、ハロゲン原子、アルキル基、およびシアノ基からなる群より選択され、
Yは、下記式(2)で表される一価の置換体である。
R1、R2、R3、R4、R5、R6、R7、R8、R9およびR10は、それぞれ独立に、水素原子、重水素原子、ハロゲン原子、アルキル基、またはアリール基であるか、または、R1、R2、R3、R4、R5、R6、R7、R8、R9およびR10から選ばれる2つ以上は、互いに結合して環を形成し、残りは、それぞれ独立に、水水素原子、重水素原子、ハロゲン原子、アルキル基、またはアリール基であり、
*は、前記式(1)中のYの結合位置を表し、
Ar1は、下記複数の式(3)で表される複数の構造からなる群より選択される。
*は、前記式(1)中のYの結合位置を表し、
**は、前記式(2)における、Ar1のNとの結合位置を表す。
X1は、水素原子、重水素原子、ハロゲン原子、アルキル基、およびシアノ基からなる群より選択され、
Yは、下記式(5)で表される一価の置換体である。
X2は、水素原子、重水素原子、ハロゲン原子、アルキル基、およびシアノ基からなる群より選択され、
Ar2は、アリール基およびヘテロアリール基のいずれかであり、
*は、上記式(4)中のYの結合位置を表す。
R11、R12、R13、およびR14は、それぞれ独立に、アルキル基およびアリール基のいずれかであり、
Zは、炭素およびケイ素のいずれかであり、
*は、式(4)中のYの結合位置及び式(5)中のAr2の一方の結合位置を表し、
***は、式(5)中のAr2の他方の結合位置を表す。
以下、本開示に係る光電変換材料および光電変換素子の実施の形態について説明する。
まず、本実施の形態に係る光電変換材料について説明する。
まず、D-A構造を有する光電変換材料について説明する。
次に、A-D-A構造を有する光電変換材料について説明する。
以下、本実施の形態に係る光電変換素子について図1Aおよび図1Bを用いて説明する。図1Aは、本実施の形態に係る光電変換素子10Aの一例を示す概略断面図である。
Oxide)を用いてもよい。Auなどの金属薄膜を透明電極として用いることもできるが、近赤外光領域の光の透過率を90%以上得ようとすると、透過率を60%から80%得られるように透明電極を作製した場合に比べ、抵抗値が極端に増大することがある。そのため、Auなどの金属材料よりもTCOの方が近赤外光に対する透明性が高く、かつ、抵抗値が小さい透明電極を得ることができる。TCOは、特に限定されないが、例えば、ITO(Indium Tin Oxide)、IZO(Indium Zinc Oxide)、AZO(Aluminum-doped Zinc Oxide)、FTO(Fluorine-doped Tin Oxide)、SnO2、TiO2、ZnO2等が挙げられる。なお、下部電極2および上部電極4は、所望の透過率に応じて、適宜、TCOおよびAuなどの金属材料を単独または複数組み合わせて作製してもよい。
<化合物1の合成>
以下に説明するステップ(1)から(3)に従い、下記構造式で表される化合物1を合成した。化合物1は、D-A構造を有する。
<化合物10の合成>
以下に説明するステップ(1)から(3)に従い、下記構造式で表される化合物10を合成した。化合物10は、A-D-A構造を有する。
実施例1のステップ(2)と同様に行い、化合物(1-j)を得た。
<化合物17の合成>
以下に説明するステップ(1)から(3)に従い、下記構造式で表される化合物17を合成した。化合物17は、A-D-A構造を有する。
実施例1のステップ(2)と同様にして、化合物(1-j)を得た。
比較例として、下記構造式で表される比較化合物1を合成した。比較化合物1は、D-A-D構造を有する。合成方法はAdvanced Materials誌、21巻、111頁から116頁を参照した。
支持基板として厚さ0.7mmの石英ガラスを用い、その上に、実施例1で得られた化合物1を含む光電変換材料をスピンコート法により成膜し、膜厚40nm、イオン化ポテンシャル5.3eVの光電変換膜を得た。得られた光電変換膜の吸収スペクトルの測定には、分光光度計(日立ハイテクノロジー製、U4100)を用いた。吸収スペクトルの測定波長域は、400nmから1200nmであった。結果を図3に示す。
支持基板として厚さ0.7mmの石英ガラスを用い、その上に、実施例2で得られた化合物10を含む光電変換材料をスピンコート法により成膜し、膜厚40nm、イオン化ポテンシャル6.0eVの光電変換膜を得た。図4に示すように、実施例5の光電変換膜は、吸収ピークが670nm付近に見られ、ピークの吸光度は、0.26であった。
支持基板として厚さ0.7mmの石英ガラスを用い、その上に、実施例3で得られた化合物17を含む光電変換材料をスピンコート法により成膜し、膜厚40nm、イオン化ポテンシャル5.4eVの光電変換膜を得た。図5に示すように、実施例6の光電変換膜は、吸収ピークが840nmと960nm付近に見られ、ピークの吸光度は、それぞれ0.34と0.35であった。
支持基板として厚さ0.7mmの石英ガラスを用い、その上に、比較例1で得られた比較化合物1をスピンコート法により成膜し、膜厚45nm、イオン化ポテンシャル5.1eVの光電変換膜を得た。得られた光電変換膜の吸収スペクトルの測定は、実施例4と同様に行った。結果を図6に示す。
以上のように、実施例4、実施例5、実施例6および比較例2の光電変換膜に関して、近赤外光に対する光吸収特性およびイオン化ポテンシャルを評価した。
近赤外光に対する光吸収特性については、実施例4の光電変換膜は、吸収ピークが820nm付近に見られ、実施例5の光電変換膜は、吸収ピークが670nm付近に見られ、吸収端は775nmに見られた、実施例6の光電変換膜は、吸収ピークが840nmと960nm付近に見られ、吸収端は1200nmに見られた。比較例2の光電変換膜は、吸収ピークが1050nm付近に見られた。このように、実施例4、実施例5、実施例6および比較例2の光電変換膜はそれぞれ、750nm以上の近赤外領域に吸収波長を有する。
実施例4の光電変換膜は、イオン化ポテンシャルが5.3eVであった。実施例5の光電変換膜は、イオン化ポテンシャルが6.0eVであった。実施例6の光電変換膜は、イオン化ポテンシャルが5.4eVであった。この結果から、本実施の形態に係る光電変換材料は、固体状態におけるイオン化ポテンシャルが5.2eVより大きいことが確認できた。
2 下部電極
3 光電変換膜
3A 光電変換層
4 上部電極
5 電子ブロッキング層
6 正孔ブロッキング層
7 p型半導体層
8 n型半導体層
10A、10B 光電変換素子
Claims (9)
- 下記第1の式で表される化合物を含む、
光電変換材料。
Xは、水素原子、重水素原子、ハロゲン原子、アルキル基、およびシアノ基からなる群より選択され、
Yは、下記第2の式で表される一価の置換体である。
R1、R2、R3、R4、R5、R6、R7、R8、R9およびR10は、それぞれ独立に、水素原子、重水素原子、ハロゲン原子、アルキル基、またはアリール基であるか、または、R1、R2、R3、R4、R5、R6、R7、R8、R9およびR10から選ばれる2つ以上は、互いに結合して環を形成し、残りは、それぞれ独立に、水素原子、重水素原子、ハロゲン原子、アルキル基、またはアリール基であり、
*は、前記第1の式中のYの結合位置を表し、
Ar1は、下記複数の第3の式で表される複数の構造からなる群より選択される。
*は、前記第1の式中のYの結合位置を表し、
**は、前記第2の式における、Ar1のNとの結合位置を表す。 - 前記光電変換材料の固体状態におけるイオン化ポテンシャルが5.2eVより大きい、
請求項1に記載の光電変換材料。 - 一対の電極と、
前記一対の電極の間に設けられた光電変換層と、
を備え、
前記光電変換層は、
n型有機半導体材料と光電変換材料とが混合されたバルクへテロ層を含み、
前記光電変換材料は、
下記第4の式で表される化合物を含む、
光電変換素子。
Xは、水素原子、重水素原子、ハロゲン原子、アルキル基、およびシアノ基からなる群より選択され、
Yは、下記第5の式で表される一価の置換体である。
R1、R2、R3、R4、R5、R6、R7、R8、R9およびR10は、それぞれ独立に、水素原子、重水素原子、ハロゲン原子、アルキル基、またはアリール基であるか、または、R1、R2、R3、R4、R5、R6、R7、R8、R9およびR10から選ばれる2つ以上は、互いに結合して環を形成し、残りは、それぞれ独立に、水素原子、重水素原子、ハロゲン原子、アルキル基、またはアリール基であり、
*は、前記第4の式中のYの結合位置を表し、
Ar1は、下記複数の第6の式で表される複数の構造からなる群より選択される。
*は、前記第4の式中のYの結合位置を表し、
**は、前記第5の式における、Ar1のNとの結合位置を表す。 - 前記n型有機半導体材料は、フラーレンおよびフラーレン誘導体からなる群から選択される少なくとも1つを含む、
請求項3に記載の光電変換素子。 - 前記光電変換材料の固体状態におけるイオン化ポテンシャルが5.2eVより大きい、
請求項5または6に記載の光電変換材料。 - 一対の電極と、
前記一対の電極の間に設けられた光電変換層と、
を備え、
前記光電変換層は、
n型有機半導体材料と光電変換材料とが混合されたバルクへテロ層を含み、
前記光電変換材料は、
下記第10の式で表される化合物を含む、
光電変換素子。
X1は、水素原子、重水素原子、ハロゲン原子、アルキル基、およびシアノ基からなる群より選択され、
Yは、下記第11の式で表される一価の置換体である。
X2は、水素原子、重水素原子、ハロゲン原子、アルキル基、およびシアノ基からなる群より選択され、
Ar2は、アリール基およびヘテロアリール基のいずれかであり、
*は、前記第10の式中のYの結合位置を表す。 - 前記n型有機半導体材料は、フラーレンおよびフラーレン誘導体からなる群から選択される少なくとも1つを含む、
請求項8に記載の光電変換素子。
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20090221762A1 (en) | 2006-01-10 | 2009-09-03 | The Trusstees Of The University Of Pennsylvania | Novel conjugated materials featuring proquinoidal units |
WO2010114116A1 (ja) | 2009-04-03 | 2010-10-07 | コニカミノルタホールディングス株式会社 | 有機光電変換素子、それを用いた太陽電池および光センサアレイ |
JP2015207759A (ja) | 2014-04-09 | 2015-11-19 | セイコーエプソン株式会社 | 発光素子、発光装置、認証装置および電子機器 |
JP2018129510A (ja) | 2017-02-06 | 2018-08-16 | 日本化薬株式会社 | 撮像素子用有機光電変換材料、これを用いた有機光電変換素素子及び有機撮像素子 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003234460A (ja) | 2002-02-12 | 2003-08-22 | Nippon Hoso Kyokai <Nhk> | 積層型光導電膜および固体撮像装置 |
US7326955B2 (en) * | 2004-08-05 | 2008-02-05 | The Trustees Of Princeton University | Stacked organic photosensitive devices |
US7375370B2 (en) * | 2004-08-05 | 2008-05-20 | The Trustees Of Princeton University | Stacked organic photosensitive devices |
EP1995787A3 (en) * | 2005-09-29 | 2012-01-18 | Semiconductor Energy Laboratory Co, Ltd. | Semiconductor device having oxide semiconductor layer and manufacturing method therof |
CN105026518B (zh) | 2013-01-04 | 2017-11-28 | 日东电工株式会社 | 用于波长转换的高荧光且光稳定性发色团 |
CN104177383A (zh) * | 2013-05-27 | 2014-12-03 | 海洋王照明科技股份有限公司 | 含萘并二噻吩单元的有机半导体材料及其制备方法和太阳能电池器件 |
TWI637958B (zh) * | 2013-09-20 | 2018-10-11 | 宇部興產股份有限公司 | 苯并雙(噻二唑)衍生物、含此衍生物之印墨、及使用此衍生物之有機電子元件 |
JP2015196659A (ja) * | 2014-04-01 | 2015-11-09 | 東レ株式会社 | 共役系化合物、これを用いた電子供与性有機材料、光起電力素子用材料および光起電力素子 |
JP2016134570A (ja) | 2015-01-21 | 2016-07-25 | パナソニックIpマネジメント株式会社 | 有機光電変換材料、光電変換素子および撮像装置 |
JP2017025039A (ja) * | 2015-07-27 | 2017-02-02 | 宇部興産株式会社 | 膜中で特定の結晶構造を有するベンゾビス(チアジアゾール)誘導体の結晶、その結晶の膜、及びそれを用いた有機エレクトロニクスデバイス |
JP2017025047A (ja) * | 2015-07-28 | 2017-02-02 | 宇部興産株式会社 | ベンゾビス(チアジアゾール)誘導体、それを含むインク、及びそれを用いた有機エレクトロニクスデバイス |
JP2018111674A (ja) * | 2017-01-13 | 2018-07-19 | セイコーエプソン株式会社 | 化合物、発光素子用化合物、発光素子、発光装置、光源、認証装置および電子機器 |
-
2018
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- 2018-08-03 US US16/054,205 patent/US10714646B2/en active Active
- 2018-08-08 JP JP2018149762A patent/JP7108870B2/ja active Active
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20090221762A1 (en) | 2006-01-10 | 2009-09-03 | The Trusstees Of The University Of Pennsylvania | Novel conjugated materials featuring proquinoidal units |
WO2010114116A1 (ja) | 2009-04-03 | 2010-10-07 | コニカミノルタホールディングス株式会社 | 有機光電変換素子、それを用いた太陽電池および光センサアレイ |
JP2015207759A (ja) | 2014-04-09 | 2015-11-19 | セイコーエプソン株式会社 | 発光素子、発光装置、認証装置および電子機器 |
JP2018129510A (ja) | 2017-02-06 | 2018-08-16 | 日本化薬株式会社 | 撮像素子用有機光電変換材料、これを用いた有機光電変換素素子及び有機撮像素子 |
Non-Patent Citations (2)
Title |
---|
Dongmei Wang et al.,Density functional theory design and characterization of D-A-A type electron donors with narrow band gap for small-molecule organic solar cells,Computational and Theoretical Chemistry,2014年,Vol.1029,pp.68-78,DOI 10.1016/j.comptc.2013.12.011 |
Yi Liu et al.,Toward Benzobis(thiadiazole)-based Diradicaloids,CHEMISTRY AN ASIAN JOURNAL,2017年07月25日,Vol.12,pp.2177-2182,DOI 10.1002/asia.201700732 |
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