JP2005063960A - ドープされた有機半導体材料およびその製造方法 - Google Patents
ドープされた有機半導体材料およびその製造方法 Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 68
- 239000004065 semiconductor Substances 0.000 title claims abstract description 56
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 20
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 40
- 239000002019 doping agent Substances 0.000 claims abstract description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 25
- 239000002800 charge carrier Substances 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910002090 carbon oxide Inorganic materials 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000975 dye Substances 0.000 claims description 28
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 19
- 125000002091 cationic group Chemical group 0.000 claims description 17
- 150000001768 cations Chemical class 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- CHVJITGCYZJHLR-UHFFFAOYSA-N cyclohepta-1,3,5-triene Chemical compound C1C=CC=CC=C1 CHVJITGCYZJHLR-UHFFFAOYSA-N 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000011159 matrix material Substances 0.000 claims description 6
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 5
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 5
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 5
- -1 azine- Chemical compound 0.000 claims description 5
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims description 5
- 238000009834 vaporization Methods 0.000 claims description 5
- 230000008016 vaporization Effects 0.000 claims description 5
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 4
- 238000010894 electron beam technology Methods 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 230000008030 elimination Effects 0.000 claims description 3
- 238000003379 elimination reaction Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims description 2
- 238000001228 spectrum Methods 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims 1
- 238000002156 mixing Methods 0.000 abstract description 4
- 150000002500 ions Chemical class 0.000 abstract 2
- 239000010410 layer Substances 0.000 description 14
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- OAZWDJGLIYNYMU-UHFFFAOYSA-N Leucocrystal Violet Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 OAZWDJGLIYNYMU-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- CXZRDVVUVDYSCQ-UHFFFAOYSA-M pyronin B Chemical compound [Cl-].C1=CC(=[N+](CC)CC)C=C2OC3=CC(N(CC)CC)=CC=C3C=C21 CXZRDVVUVDYSCQ-UHFFFAOYSA-M 0.000 description 6
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 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 4
- LGLFFNDHMLKUMI-UHFFFAOYSA-N crystal violet cation Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C1C=CC(=[N+](C)C)C=C1 LGLFFNDHMLKUMI-UHFFFAOYSA-N 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000005839 radical cations Chemical class 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K99/00—Subject matter not provided for in other groups of this subclass
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/30—Doping active layers, e.g. electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
- H10K50/165—Electron transporting layers comprising dopants
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H—ELECTRICITY
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
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Abstract
【解決手段】 ドーパント(1)を有機半導体材料に混合した後、水素、酸化炭素、窒素またはヒドロキシラジカルを脱離させ、少なくとも1つの電子を、半導体材料へ移し、または、半導体材料から移す。この方法は、ドーパント(1)として電荷を持たない有機化合物を使用することを特徴とする。本発明の半導体材料は、ドープされた層が、少なくとも1つの有機化合物の陽イオン(2)を含むことを特徴とする。ここで、電荷を持たない形の有機化合物(1)は、空気中で不安定である。
【選択図】 図1
Description
2 有機化合物のカチオン
Claims (18)
- 高い電化担体密度と効果的な電荷担体移動性とを有するドープされた有機半導体材料を、ドーパントをドーピングすることによって製造する方法であって、ドーパントを有機半導体材料に混合した後、水素、酸化炭素、窒素またはヒドロキシラジカルを脱離し、少なくとも1つの電子を、半導体材料へ移し、または、半導体材料から移すとともに、
ドーパントとして、電荷を持たない有機化合物を使用することを特徴とする方法。 - 上記ドーパントを、有機化合物の塩を昇華させることによって製造することを特徴とする、請求項1に記載の方法。
- 上記電荷を持たない有機化合物を、水素、酸化炭素、窒素またはヒドロキシラジカルの脱離によって有機化合物のカチオンまたはラジカルに変換することを特徴とする、請求項1または2に記載の方法。
- 水素、酸化炭素、窒素またはヒドロキシラジカルを、シクロペンタジエン、シクロヘプタトリエンまたは6員ヘテロ環から6π芳香族系を形成しながら脱離させることを特徴とする、請求項1〜3のいずれか1項に記載の方法。
- シクロペンタジエン、シクロヘプタトリエンまたは6員ヘテロ環が、縮合環の構成要素であることを特徴とする、請求項4に記載の方法。
- 上記電荷を持たない有機化合物が、陽イオン色素のカルビノール塩基またはロイコ塩基であることを特徴とする、請求項1〜5のいずれか1項に記載の方法。
- キサンテン−、アクリジン−、ジフェニルアミン−、トリフェニルアミン−、アジン−、オキサジン−、チアジン−またはチオキサンテン−色素誘導体を、色素として使用することを特徴とする、請求項1〜6のいずれか1項に記載の方法。
- 上記電荷を持たない有機化合物が、有機半導体材料に混合する前または後に、光照射されるか、または、電子線によって励起されることを特徴とする、請求項1〜7のいずれか1項に記載の方法。
- 上記光照射のために使用する照射のスペクトルが、電荷を持たない有機化合物および/またはドープする有機半導体材料の吸収領域を少なくとも部分的に覆うことを特徴とする、請求項8に記載の方法。
- 上記ドーパントと有機半導体材料との間で、化学結合を形成せずに、少なくとも1つの電荷を移動させることを特徴とする、請求項1〜9のいずれか1項に記載の方法。
- 上記有機半導体材料に、混合気化または連続する気化によって、陽イオン色素またはそのロイコ塩基またはカルビノール塩基をドープし、上記陽イオン色素から生じる化合物を、上記有機半導体材料および/または生じた化合物の吸収領域に電子線または光を照射することにより、陽イオンに再変換することを特徴とする、請求項1〜10のいずれか1項に記載の方法。
- 上記有機半導体材料およびドーパントが、暗所ではマトリックスにある化合物が不活性であるように互いに調節された酸化還元電位を有している、不均一にドープされた層が形成されることを特徴とする、請求項1〜11のいずれか1項に記載の方法。
- 高い電荷担体密度と効果的な電荷担体移動性とを有する、ドープされた有機半導体材料であって、
上記ドープされた層に、電荷を持たない形が空気中で不安定な少なくとも1つの有機化合物の陽イオンが含まれることを特徴とする半導体材料。 - 上記有機化合物が色素であることを特徴とする、請求項13に記載の半導体材料。
- 上記色素が、キサンテン−、アクリジン−、ジフェニルアミン−、トリフェニルアミン−、アジン−、オキサジン−、チアジン−またはチオキサンテン−色素誘導体であることを特徴とする、請求項14に記載の半導体材料。
- 上記電荷を持たない有機化合物が、陽イオン色素のカルビノール塩基またはロイコ塩基であることを特徴とする、請求項13に記載の半導体材料。
- 水素、酸化炭素、窒素またはヒドロキシラジカルが、シクロペンタジエン、シクロヘプタトリエンまたは6員ヘテロ環から脱離していることを特徴とする、請求項13に記載の半導体材料。
- シクロペンタジエン、シクロヘプタトリエンまたは6員ヘテロ環が、縮合環系の構成要素であることを特徴とする、請求項17に記載の半導体材料。
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DE10338406A DE10338406A1 (de) | 2003-08-18 | 2003-08-18 | Dotierte organische Halbleitermaterialien sowie Verfahren zu deren Herstellung |
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US (1) | US7151007B2 (ja) |
EP (1) | EP1508903A3 (ja) |
JP (1) | JP4108654B2 (ja) |
KR (1) | KR100746798B1 (ja) |
CN (1) | CN100418246C (ja) |
CA (1) | CA2476168A1 (ja) |
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IN (1) | IN2004MU00746A (ja) |
TW (1) | TWI265648B (ja) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007273978A (ja) * | 2006-03-21 | 2007-10-18 | Novaled Ag | マトリックス材料とドーピング材料とからなる混合物、及び、ドーピングされた有機材料からなる層の製造方法 |
JP2009500861A (ja) * | 2005-07-15 | 2009-01-08 | エルジー・ケム・リミテッド | 有機発光素子およびその製造方法 |
JP2009530835A (ja) * | 2006-03-22 | 2009-08-27 | ノヴァレッド・アクチエンゲゼルシャフト | 有機半導体のドーピングを目的とした複素環式ラジカルの使用 |
WO2017122538A1 (ja) * | 2016-01-13 | 2017-07-20 | ソニー株式会社 | 光電変換素子および撮像素子ならびに電子機器 |
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Publication number | Priority date | Publication date | Assignee | Title |
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US8907323B2 (en) * | 2002-04-23 | 2014-12-09 | Philip D. Freedman | Microprocessor assembly |
US7540978B2 (en) * | 2004-08-05 | 2009-06-02 | Novaled Ag | Use of an organic matrix material for producing an organic semiconductor material, organic semiconductor material and electronic component |
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WO2017122538A1 (ja) * | 2016-01-13 | 2017-07-20 | ソニー株式会社 | 光電変換素子および撮像素子ならびに電子機器 |
JPWO2017122538A1 (ja) * | 2016-01-13 | 2018-11-22 | ソニー株式会社 | 光電変換素子および撮像素子ならびに電子機器 |
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Also Published As
Publication number | Publication date |
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CN100418246C (zh) | 2008-09-10 |
EP1508903A2 (de) | 2005-02-23 |
US20050061232A1 (en) | 2005-03-24 |
EP1508903A3 (de) | 2006-02-15 |
CA2476168A1 (en) | 2005-02-18 |
JP4108654B2 (ja) | 2008-06-25 |
KR100746798B1 (ko) | 2007-08-06 |
DE10338406A1 (de) | 2005-03-24 |
CN1591926A (zh) | 2005-03-09 |
TW200509428A (en) | 2005-03-01 |
IN2004MU00746A (ja) | 2006-06-16 |
KR20050020663A (ko) | 2005-03-04 |
US7151007B2 (en) | 2006-12-19 |
TWI265648B (en) | 2006-11-01 |
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