JP7397621B2 - 有機化合物とそれを含む有機光電素子、イメージセンサ、及び電子素子 - Google Patents
有機化合物とそれを含む有機光電素子、イメージセンサ、及び電子素子 Download PDFInfo
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- JP7397621B2 JP7397621B2 JP2019196379A JP2019196379A JP7397621B2 JP 7397621 B2 JP7397621 B2 JP 7397621B2 JP 2019196379 A JP2019196379 A JP 2019196379A JP 2019196379 A JP2019196379 A JP 2019196379A JP 7397621 B2 JP7397621 B2 JP 7397621B2
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- GQVWHWAWLPCBHB-UHFFFAOYSA-L beryllium;benzo[h]quinolin-10-olate Chemical compound [Be+2].C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21.C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21 GQVWHWAWLPCBHB-UHFFFAOYSA-L 0.000 description 1
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- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
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- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
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- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
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- 229920000128 polypyrrole Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
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- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 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
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- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- CRUIOQJBPNKOJG-UHFFFAOYSA-N thieno[3,2-e][1]benzothiole Chemical compound C1=C2SC=CC2=C2C=CSC2=C1 CRUIOQJBPNKOJG-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 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
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- 238000005019 vapor deposition process 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
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Description
化学式(1a)の化合物を(反応式1)によって合成した。
化学式(1b)の合成
化学式(1b)の化合物を(反応式2)によって合成した。
化学式(1c)の合成
化学式(1c)の化合物を(反応式3)によって合成した。
1H-NMR(CDCl3,ppm):δ=1.02(t,J=7.6Hz,6H),1.40(s,6H),2.33(q,J=7.6 Hz,4H),2.56(s,6H),7.41-7.43(m,2H),7.50-7.53(m,2H),7.80(d,J=5Hz, 1H),7.85-7.91(m,3H),7.96(d,J=4.2Hz,1H),8.27(dd,J=4.4Hz,1H),8.45(s, 1H).
化学式(1d)の合成
化学式(1d)の化合物を(反応式4)によって合成した。
化学式(1e)の合成
化学式(1e)の化合物を(反応式5)によって合成した。
化学式(1f)の合成
化学式(1f)の化合物を(反応式6)によって合成した。
化学式(1g)の合成
化学式(1g)の化合物を(反応式7)によって合成した。
化学式(1h)の合成
化学式(1h)の化合物を(反応式8)によって合成した。
化学式(1i)の合成
化学式(1i)の化合物を(反応式9)によって合成した。
化学式(1j)の合成
化学式(1j)の化合物を(反応式10)によって合成した。
化学式(1k)の合成
化学式(1k)の化合物を(反応式11)によって合成した。
化学式(1l)の合成
化学式(1l)は、アルドリッチ社製品の試薬を使用した。昇華精製を行って化学式(1l)を回収した。
化学式(1m)の合成
化学式(1m)の化合物は、化学式(1a)の化合物の合成時に使用された5-(4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン-2-イル)-2,2’-ビチオフェンを、2-(4-ビフェニリル)-4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン(2-(4-biphenylyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)に代替し、化学式(1a)の化合物の合成時と同様のモル配合比で同一作業を行い、化学式(1m)1.60gを回収した。
以下、本発明の技術的思想による実施例による有機化合物の物理的特性について説明する。
図11は、本発明の技術的思想による実施例による有機光電素子の製造例を説明するための断面図である。図11を参照すれば、ガラス基板502上にITOからなる第1電極層510を形成し、第1電極層510上に30nm厚さのモリブデン酸化物薄膜からなる電子遮断層520を形成した。その後、電子遮断層520上に化学式(1a)の化合物とC60(Frontier Carbon Company Ltd.)を3:2の体積比で共蒸着(co-depositing)して80nmの厚さを有する活性層530を形成した。その後、活性層530上にAlを真空蒸着して100nm厚さの第2電極540を形成して有機光電素子500を製造した。
化学式(1a)の化合物の代わりに、化学式(1b)、化学式(1d)、化学式(1f)、化学式(1g)、及び化学式(1h)の化合物を使用したことを除いて、素子製造例1と同じ方法で有機光電素子を製造した。
化学式(1a)の化合物の代わりに、化学式(1m)を使用したことを除いて、素子製造例1と同じ方法で有機光電素子を製造した。
化学式(1a)、化学式(1b)、化学式(1d)、化学式(1f)、化学式(1g)、及び化学式(1h)の化合物を含む活性層を有する有機光電素子は、n2ガス雰囲気下で130℃でアニーリングした後にも、有機光電素子の特性が劣化しないことを確認した。かような結果から、化学式(1a)、化学式(1b)、化学式(1d)、化学式(1f)、化学式(1g)、及び化学式(1h)の化合物は、熱的安定性が非常に優秀であるということが分かる。
120 活性層
130 第2電極
240 第1電荷補助層
250 第2電荷補助層
Claims (3)
- 互いに対面する第1電極及び第2電極と、
前記第1電極と前記第2電極との間に介在された活性層と、
を含む有機光電素子であって、前記活性層は、化学式1:
Aは、少なくとも1つの硫黄原子を含むヘテロアリール基を有する作用基である。)
で表される有機化合物を含む、有機光電素子であって、
化学式1で表される有機化合物において、Aは、次の置換基:
のうちから選択されるいずれか1つの置換基を有することを特徴とする、有機光電素子。 - 半導体基板と、
前記半導体基板上に配置された有機光電素子と、
を含むイメージセンサであって、
前記有機光電素子は、
互いに対面する第1電極及び第2電極と、
前記第1電極と前記第2電極との間に介在され、化学式1:
Aは、少なくとも1つの硫黄原子を含むヘテロアリール基を有する作用基である。)
で表される有機化合物を含む活性層と、
を含み、
化学式1で表される有機化合物において、Aは、次の置換基:
のうちから選択されるいずれか1つの置換基を含むことを特徴とする、イメージセンサ。
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KR20180132569 | 2018-10-31 | ||
KR10-2018-0132569 | 2018-10-31 | ||
KR1020190082231A KR102683412B1 (ko) | 2018-10-31 | 2019-07-08 | 유기 화합물과 이를 포함하는 유기 광전 소자, 이미지 센서, 및 전자 소자 |
KR10-2019-0082231 | 2019-07-08 |
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