JP2017005249A - 有機光電変換素子、光エリアセンサ、撮像素子および撮像装置 - Google Patents
有機光電変換素子、光エリアセンサ、撮像素子および撮像装置 Download PDFInfo
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- JP2017005249A JP2017005249A JP2016112161A JP2016112161A JP2017005249A JP 2017005249 A JP2017005249 A JP 2017005249A JP 2016112161 A JP2016112161 A JP 2016112161A JP 2016112161 A JP2016112161 A JP 2016112161A JP 2017005249 A JP2017005249 A JP 2017005249A
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- FQRWAZOLUJHNDT-UHFFFAOYSA-N c12c3c4c5c6c7c8c9c%10c%11c%12c%13c%14c%15c%16c%17c(c1c1c4c7c%10c%13c%161)c1c2c2c4c7c%10c%13c%16c%18c%19c%20c%21c%22c%23c%24c%25c%26c%27c%28c%29c(c7c7c%13c%19c%22c%25c%287)c4c1c1c%17c%15c(c%27c%291)c1c%14c%12c(c%24c%261)c1c%11c9c(c%21c%231)c1c8c6c(c%18c%201)c1c5c3c2c%10c%161 Chemical compound c12c3c4c5c6c7c8c9c%10c%11c%12c%13c%14c%15c%16c%17c(c1c1c4c7c%10c%13c%161)c1c2c2c4c7c%10c%13c%16c%18c%19c%20c%21c%22c%23c%24c%25c%26c%27c%28c%29c(c7c7c%13c%19c%22c%25c%287)c4c1c1c%17c%15c(c%27c%291)c1c%14c%12c(c%24c%261)c1c%11c9c(c%21c%231)c1c8c6c(c%18c%201)c1c5c3c2c%10c%161 FQRWAZOLUJHNDT-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical class 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
- 238000004891 communication Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 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
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002219 fluoranthenes Chemical class 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 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
- 239000003446 ligand Substances 0.000 description 1
- 230000004298 light response Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- IUTZKZLVPUPHDA-UHFFFAOYSA-N n-(4-chlorophenyl)-2h-triazol-4-amine Chemical compound C1=CC(Cl)=CC=C1NC1=NNN=C1 IUTZKZLVPUPHDA-UHFFFAOYSA-N 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
- 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002071 nanotube Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 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
- 229920000548 poly(silane) polymer Chemical class 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 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
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000005546 reactive sputtering Methods 0.000 description 1
- 230000009257 reactivity Effects 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
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 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
- 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
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000005580 triphenylene 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
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
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Abstract
Description
図1は、本実施形態に係る有機光電変換素子の一例を示す断面模式図である。有機光電変換素子には、光を電荷に変換する光電変換部として第一の有機化合物層1が、カソード4とアノード5との間に配置されている。第一の有機化合物層は、光を電荷に変換する層であることから、光電変換層と呼ぶこともできる。
本発明に係る有機光電変換素子が有する第一の有機化合物層は、光を受け、その光量に応じた電荷を発生する層である。その機能から光電変換層と呼ぶこともできる。第一の有機化合物層は、複数種類の有機化合物を有してもよい。
一般式(1)の有機化合物は、David M.Lemal、“Journal of American Chemical Society,1964,86(12),pp2518−2519”に合成方法が記載されている。記載されている合成方法における試薬を適宜変更することで、種々の一般式(1)の有機化合物を合成することができる。
一般式(3)の有機化合物は、例えば、以下の合成方法により合成することができる。
まず200mlの三ツ口フラスコを用意し、このフラスコ内に、下記に示される試薬を入れた。
化合物b−11:1.50g(7.68mmol)
化合物b−12:2.41g(15.36mmol)
ナトリウムターシャリブトキシド:1.47g(15.36mmol)
まず50ml三ツ口フラスコを用意し、このフラスコ内に、アセトン30mlを入れた後、アルゴンで15分、バブリングした。次に、フラスコ内に、以下に示される試薬を入れた。
化合物b−13:271mg(1.0mmol)
亜鉛粉:1.30g(20.0mmol)
一般式(4)の有機化合物は、例えば、以下のスキームより合成することができる。
E1:2.36g(10.0mmol)
E2:2.33g(21.0mmol)
酢酸パラジウム:67mg(0.3mmol)
トリ−tert−ブチルホスフィン:0.17ml(0.7mol)
ナトリウム−tert−ブトキシド:2.31g(24.0mmol)
トルエン:50mL
E3:1.48g(5.00mmol)
オルトギ酸トリエチル:25ml
E4:342mg(1.00mmol)
脱水THF:20mL
実測値:m/z=612.38 計算値:612.19
一般式(5)の有機化合物は、例えば、以下の合成方法により合成することができる。
E11:1.36g(10.0mmol)
E15:4.35g(21.0mmol)
トリス(ジベンジリデンアセトン)ジパラジウム(0):274mg(0.3mmol)
2−ジシクロヘキシルホスフィノ−2’、4’、6’−トリイソプロピルビフェニル:333mg(0.7mol)
ナトリウム−tert−ブトキシド:2.31g(24.0mmol)
トルエン:50mL
E27:1.94g(5.00mmol)
オルトギ酸トリエチル:50ml
E4:435mg(1.00mmol)
脱水DMF:5mL
実測値:m/z=796.33 計算値:796.36
E1:1.36g(10.0mmol)
E2:3.30g(21.0mmol)
トリス(ジベンジリデンアセトン)ジパラジウム(0):274mg(0.3mmol)
2−ジシクロヘキシルホスフィノ−2’,4’,6’−トリイソプロピルビフェニル:333mg(0.7mol)
ナトリウム−tert−ブトキシド:2.31g(24.0mmol)
トルエン:50mL
E27:1.45g(5.00mmol)
オルトギ酸トリエチル:50ml
E4:336mg(1.00mmol)
脱水DMF:5mL
実測値:m/z=600.29 計算値:600.27
本発明に係る有機光電変換素子は、第一の有機化合物層が有する有機化合物を変更することで、異なる色の光に対応する有機光電変換素子とすることができる。異なる色に対応するとは、光電変換部が光電変換する光の波長領域が異なることを意味する。
以下の方法により、一般式(1)の例示化合物A1のイオン化ポテンシャルを測定した。
以下の方法により、一般式(1)の例示化合物A1のバンドギャップを測定した。
例示化合物A3を真空蒸着法により、シリコン基板上に蒸着し、50nmの有機化合物層を作製した。
Claims (21)
- アノードと、カソードと、前記アノードと前記カソードとの間に配置されている光電変換部と、を有する有機光電変換素子であって、
前記光電変換部は第一の有機化合物層を有し、
前記カソードと前記光電変換部との間に配置されている第二の有機化合物層を有し、
前記第二の有機化合物層は、イオン化ポテンシャルが5.1eV以下であり、かつバンドギャップが2.5eV以上である有機化合物を有することを特徴とする有機光電変換素子。 - 前記第二の有機化合物層が有する前記有機化合物は、基板上に蒸着され、水を滴下された場合に、水の滴下時から10分後の層厚の減少率が、0%以上50%以下であることを特徴とする請求項1に記載の光電変換素子。
- 前記第二の有機化合物層が有する有機化合物の電子親和力の値が、前記第一の有機化合物層が有する有機化合物の電子親和力の値よりも0.5eV以上小さいことを特徴とする請求項1または2に記載の有機光電変換素子。
- 前記第二の有機化合物層が有する有機化合物の電子親和力が、前記カソードの仕事関数の値よりも1.0eV以上小さいことを特徴とする請求項1乃至3のいずれか一項に記載の有機光電変換素子。
- 前記第二の有機化合物層が有する有機化合物のイオン化ポテンシャルの値が、前記第一の有機化合物層が有する有機化合物のイオン化ポテンシャルよりも小さいことを特徴とする請求項1乃至4のいずれか一項に記載の有機光電変換素子。
- 前記第二の有機化合物層が有する有機化合物のイオン化ポテンシャルの値が、前記第一の有機化合物層が有する有機化合物のイオン化ポテンシャルよりも0.5eV以上小さい有機化合物を有することを特徴とする請求項5に記載の有機光電変換素子。
- 前記第一の有機化合物層は、複数種類の有機化合物を有することを特徴とする請求項1乃至6のいずれか一項に記載の有機光電変換素子。
- 前記光電変換部は、第三の有機化合物層をさらに有し、前記第三の有機化合物層は前記第一の有機化合物層に接して配置され、
前記第一の有機化合物層と前記第三の有機化合物層は、前記カソードから前記アノードの方向に、積層されていることを特徴とする請求項1乃至7のいずれか一項に記載の有機光電変換素子。 - 前記第二の有機化合物層は、イミダゾリデン誘導体、ベンゾイミダゾリデン誘導体、アクリジニリデン誘導体のいずれかを有することを特徴とする請求項1乃至8のいずれか一項に記載の有機光電変換素子。
- 前記第二の有機化合物層は、前記カソードに接していることを特徴とする請求項1乃至9のいずれか一項に記載の有機光電変換素子。
- 複数の有機光電変換素子を有し、前記有機光電変換素子が請求項1乃至10のいずれか一項に記載の有機光電変換素子であり、前記複数の有機光電変換素子が複数の行および複数の列を含む二次元に配置されていることを特徴とする光エリアセンサ。
- 前記複数の有機光電変換素子のそれぞれは、前記有機光電変換素子とは異なる色の光を光電変換する、別種の有機光電変換素子をさらに有し、
前記複数の有機光電変換素子のそれぞれと、前記別種の有機光電変換素子とが積層されていることを特徴とする請求項11に記載の光エリアセンサ。 - 複数の画素と、前記画素に接続されている信号処理部と、を有する撮像素子であって、
前記複数の画素は、複数の行および複数の列を含む二次元に配置されており、
前記画素は、請求項1乃至10のいずれか一項に記載の有機光電変換素子と、前記有機光電変換素子に接続されている読み出し回路と、を有することを特徴とする撮像素子。 - 前記複数の画素のそれぞれは、前記有機光電変換素子とは異なる色の光を光電変換する、別種の有機光電変換素子をさらに有し、前記有機光電変換素子と、前記別種の光電変換素子とが積層されていることを特徴とする請求項13に記載の撮像素子。
- 前記撮像素子の光入射側に、波長選択部、マイクロレンズ、光フィルタの少なくともいずれかを有することを特徴とする請求項14に記載の撮像素子。
- 前記波長選択部、前記マイクロレンズ、前記光フィルタの少なくともいずれかは、前記複数の画素のそれぞれに設けられていることを特徴とする請求項15に記載の撮像素子。
- 撮像光学系と、前記撮像光学系を通過した光を受光する撮像素子とを有し、前記撮像素子は、請求項12乃至16のいずれか一項に記載の撮像素子であることを特徴とする撮像装置。
- 撮像光学系と接合可能な接合部と、請求項12乃至16のいずれか一項に記載の撮像素子と、を有することを特徴とする撮像装置。
- 前記撮像装置は、デジタルカメラまたはデジタルスチルカメラであることを特徴とする請求項17または18に記載の撮像装置。
- 前記撮像装置は、外部からの信号を受信する受信部をさらに有し、前記信号は、前記撮像装置の撮像範囲、撮像の開始、撮像の終了の少なくともいずれかを制御する信号であることを特徴とする請求項17に記載の撮像装置。
- 前記撮像装置は、取得した画像を外部に送信する送信部をさらに有することを特徴とする請求項17または20に記載の撮像装置。
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