JPWO2015119039A1 - 光電変換素子およびイメージセンサ - Google Patents
光電変換素子およびイメージセンサ Download PDFInfo
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- JPWO2015119039A1 JPWO2015119039A1 JP2015506036A JP2015506036A JPWO2015119039A1 JP WO2015119039 A1 JPWO2015119039 A1 JP WO2015119039A1 JP 2015506036 A JP2015506036 A JP 2015506036A JP 2015506036 A JP2015506036 A JP 2015506036A JP WO2015119039 A1 JPWO2015119039 A1 JP WO2015119039A1
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- photoelectric conversion
- conversion element
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 176
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 125000003118 aryl group Chemical group 0.000 claims abstract description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 23
- 229910052751 metal Inorganic materials 0.000 claims abstract description 19
- 239000002184 metal Substances 0.000 claims abstract description 19
- 239000012044 organic layer Substances 0.000 claims abstract description 18
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052796 boron Inorganic materials 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 8
- 239000011777 magnesium Substances 0.000 claims abstract description 8
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 7
- 239000011651 chromium Substances 0.000 claims abstract description 7
- 229910052802 copper Inorganic materials 0.000 claims abstract description 7
- 239000010949 copper Substances 0.000 claims abstract description 7
- 229910052742 iron Inorganic materials 0.000 claims abstract description 7
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000005013 aryl ether group Chemical group 0.000 claims abstract description 6
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 6
- 239000011701 zinc Substances 0.000 claims abstract description 6
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- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
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- 239000010410 layer Substances 0.000 claims description 75
- 239000000463 material Substances 0.000 claims description 55
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 230000000903 blocking effect Effects 0.000 description 28
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 229910052792 caesium Inorganic materials 0.000 description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 150000004866 oxadiazoles Chemical class 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
- RRPCBMLYCVUGAC-UHFFFAOYSA-N 3,5-bis(4-tert-butylphenyl)benzaldehyde Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1C=C(C=O)C=C(C1)C1=CC=C(C=C1)C(C)(C)C RRPCBMLYCVUGAC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
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- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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Abstract
Description
本発明の光電変換素子は、第一電極と第二電極の間に少なくとも一層の有機層が存在し、光を電気エネルギーに変換する光電変換素子であって、前記有機層に後述の一般式(1)で表される化合物を含有するものである。
光電変換素子において、陽極と陰極は、素子の中で作られた電子および正孔を流し、十分に電流を流せるための役割を有する。陽極と陰極は、光電変換層に光を入射させるために、少なくとも一方は透明または半透明であることが望ましい。通常、基板上に形成される陽極を透明電極とすることが好ましい。
光電変換層は、単独の光電変換素子材料から構成されていても良いが、高い光電変換効率を得るためには2種類以上の光電変換素子材料から構成されることが好ましく、電子供与性の光電変換素子材料と電子受容性の光電変換素子材料から構成されることがより好ましい。光電変換層が2種以上の光電変換素子材料から構成される場合、該光電変換層は、2種以上の光電変換素子材料が混合された1層でもよいし、それぞれ1種以上の光電変換素子材料からなる層が積層された複数層でもよい。さらには、混合層と各々の単独層が混合された構成でも良い。
電荷阻止層とは、光電変換層で光電変換された電子および正孔を効率良くかつ安定に電極から取り出すために用いられる層であり、電子を阻止する電子阻止層と正孔を阻止する正孔阻止層とが挙げられる。これらは無機物から構成されても良いし、有機化合物から構成されても良い。さらに、無機物と有機化合物の混合層からなってもよい。
本発明の光電変換素子は、有機層に一般式(1)で表される化合物を含有する。
イメージセンサは、光学的な映像を電気的な信号に変換する半導体素子である。一般的にイメージセンサは、光を電気エネルギーに変換する前述の光電変換素子と電気エネルギーを電気信号に読み出す回路で構成される。イメージセンサの用途によって、複数の光電変換素子を一次元直線または二次元平面に配列することができる。また、モノカラーのイメージセンサの場合は、1種の光電変換素子のみを有していてもよいが、カラーイメージセンサの場合は、2種以上の光電変換素子を有する。例えば赤色光を検出する光電変換素子、緑色光を検出する光電変換素子、および青色光を検出する光電変換素子を有する。各色の光電変換素子は、積層構造、すなわち一つの画素に複数の光電変換素子が積層された構造で構成されていてもよいし、複数の光電変換素子が横に並んだマトリクス構造で構成されてもよい。
化合物[1]の合成方法
3,5−ジブロモベンズアルデヒド(3.0g)、4−t−ブチルフェニルボロン酸(5.3g)、テトラキス(トリフェニルホスフィン)パラジウム(0)(0.4g)、炭酸カリウム(2.0g)をフラスコに入れ、窒素置換した。ここに脱気したトルエン(30mL)および脱気した水(10mL)を加え、4時間還流した。反応溶液を室温まで冷却し、有機層を、分液した後に飽和食塩水で洗浄した。この有機層を硫酸マグネシウムで乾燥し、ろ過後、溶媒を留去した。得られた反応生成物をシリカゲルクロマトグラフィーにより精製し、3,5−ビス(4−t−ブチルフェニル)ベンズアルデヒド(3.5g)を白色固体として得た。
1H−NMR(CDCl3,ppm):7.95(s,1H)、7.63−7.48(m,10H)、6.00(s,2H)、2.58(s,6H)、1.50(s,6H)、1.37(s,18H)。
吸収スペクトル:λmax514nm(薄膜:50nm)
半値幅:39nm
吸収係数:1.21×105/cm
石英基板上に下記に示す化合物D−1と上記化合物[1]を蒸着速度比1:1で50nm蒸着した。蒸着膜の吸収スペクトルを測定した結果、図5に示すように緑色領域のみに吸収を持つシャープな吸収スペクトルとなった。また、光吸収特性は以下の通りであった。
吸収スペクトル:λmax514nm
半値幅:39nm
吸収係数:7.42×104/cm
化合物[1]の代わりにA−1を用いたこと以外は、合成例1と同様の方法で化合物D−1と化合物A−1を石英基板上に蒸着し、吸収スペクトルを測定した。図6に示すように緑領域だけでなく、赤領域および青領域にも吸収を持つブロードな吸収スペクトルとなった。また、光吸収特性は以下の通りであった。
吸収スペクトル:λmax529nm
半値幅:142nm
吸収係数:9.06×104/cm。
化合物[1]を用いた光電変換素子を次のように作製した。ITO透明導電膜を150nm堆積させたガラス基板(旭硝子(株)製、15Ω/□、電子ビーム蒸着品)を30×40mmに切断し、エッチングを行い、陽極基板を得た。得られた陽極基板をアセトンおよび”セミコクリーン(登録商標)56”(フルウチ化学(株)製)を用いて、各々15分間超音波洗浄してから、超純水で洗浄した。続いて、イソプロピルアルコールを用いて15分間超音波洗浄し、さらに熱メタノールに15分間浸漬させた後、乾燥した。この陽極基板を、素子を作製する直前に1時間UV−オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が5×10−5Pa以下になるまで排気した。この陽極基板のITO層上に、抵抗加熱法によって、電子阻止層として酸化モリブデンを30nm蒸着した。次に、光電変換層として化合物D−1と化合物[1]を蒸着速度比1:1で共蒸着した。次に、アルミニウムを100nm蒸着して陰極とし、5×5mm角の素子を得た。ここで言う膜厚は、水晶発振式膜厚モニター表示値である。
光電変換層を蒸着する時、化合物[1]の代わりにA−1を用いた以外は実施例1と同様にして光電変換素子を作製した。
化合物D−1と化合物[1]の蒸着速度比を、それぞれ2:1、3:1に変更したこと以外は、実施例1と同様にして光電変換素子を作製した。各光電変換素子にバイアス電圧(−5V)を印加したときの光電変換特性を表1に示す。いずれの素子においても、色選択性が良好な光電変換特性を示した。
化合物[1]の代わりにn型半導体材料として下記に示す化合物を用いた以外は、実施例1と同様にして光電変換素子を作製した。各光電変換素子にバイアス電圧(−5V)を印加したときの光電変換特性を表1に示す。実施例4〜10においては、吸収スペクトルの半値幅が小さく色選択性が良好であったが、比較例2においては吸収スペクトルの半値幅が大きく、色選択性が悪化した。
13 電子阻止層
15 光電変換層
17 正孔阻止層
20 第二電極
30 光
31 赤色光を検出する光電変換素子
32 緑色光を検出する光電変換素子
33 青色光を検出する光電変換素子
Claims (13)
- 第一電極と第二電極の間に少なくとも一層の有機層が存在し、光を電気エネルギーに変換する光電変換素子であって、前記有機層に一般式(1)で表される化合物を含有する光電変換素子;
- 一般式(1)のR1〜R4がメチル基であり、R5およびR6が水素である請求項1記載の光電変換素子。
- 一般式(1)のMがホウ素、Lがフッ素または含フッ素アリール基、m−1が2である請求項1または2記載の光電変換素子。
- 一般式(1)のR7がアリール基またはヘテロアリール基である請求項1〜3いずれか記載の光電変換素子。
- 前記有機層が光電変換層を含み、該光電変換層に前記一般式(1)で表される化合物を含有する請求項1〜5いずれか記載の光電変換素子。
- 前記光電変換層が2種類の光電変換素子材料で構成されており、そのうちの1種類が前記一般式(1)で表される化合物である請求項6記載の光電変換素子。
- 前記2種類の光電変換素子材料がそれぞれ電子供与性および電子受容性の光電変換素子材料であり、前記一般式(1)で表される化合物が電子受容性の光電変換素子材料である請求項7記載の光電変換素子。
- 請求項1〜8いずれか記載の光電変換素子を含むイメージセンサ。
- 2種類以上の光電変換素子を有し、そのうちの1種類の光電変換素子が請求項1〜8いずれか記載の光電変換素子である請求項9記載のイメージセンサ。
- 前記2種類以上の光電変換素子が積層構造を有する請求項10記載のイメージセンサ。
- 赤色光、緑色光および青色光を検出する光電変換素子を有し、該緑色光を検出する光電変換素子が請求項1〜8いずれか記載の光電変換素子である請求項11記載のイメージセンサ。
- 前記緑色光を検出する光電変換素子が入射光に対して最も近い層に配置されている請求項12記載のイメージセンサ。
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TAHSIN KILICOGLU ET AL.: ""Electrical and photovoltaic properties of an organic-inorganic heterojunction based on a BODIPY dye", MICROELECTRONIC ENGINEERING, vol. 88, JPN6018036500, 2011, pages 150 - 154, XP027507573, ISSN: 0003993455, DOI: 10.1016/j.mee.2010.10.001 * |
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KR102480671B1 (ko) | 2022-12-23 |
TWI646673B (zh) | 2019-01-01 |
KR20210062098A (ko) | 2021-05-28 |
CN105960714A (zh) | 2016-09-21 |
US9842884B2 (en) | 2017-12-12 |
CN105960714B (zh) | 2018-02-09 |
KR20160119052A (ko) | 2016-10-12 |
KR20220054465A (ko) | 2022-05-02 |
WO2015119039A1 (ja) | 2015-08-13 |
TW201532255A (zh) | 2015-08-16 |
JP6558243B2 (ja) | 2019-08-14 |
US20160351810A1 (en) | 2016-12-01 |
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