JP2017529688A - 有機エレクトロルミネッセンストランジスタ - Google Patents
有機エレクトロルミネッセンストランジスタ Download PDFInfo
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- JP2017529688A JP2017529688A JP2017503880A JP2017503880A JP2017529688A JP 2017529688 A JP2017529688 A JP 2017529688A JP 2017503880 A JP2017503880 A JP 2017503880A JP 2017503880 A JP2017503880 A JP 2017503880A JP 2017529688 A JP2017529688 A JP 2017529688A
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- 229910052741 iridium Inorganic materials 0.000 claims abstract description 14
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims abstract 3
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- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000007649 pad printing Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical class C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 150000003342 selenium Chemical class 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
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Abstract
Description
誘電体層は、制御電極及びアセンブリの間に配置されており、
両極性チャネルは、n型半導体材料の少なくとも1つの層、p型半導体材料の少なくとも1つの層、並びにp型及びn型半導体材料の層の間に配置されている放出性材料の少なくとも1つの層を含み、
p型半導体材料は、トランジスタの両極性チャネルを横切って正孔を輸送するのに適しており、一般式(P-I)
誘電体層は、制御電極及びアセンブリの間に配置されており、
両極性チャネルは、n型半導体材料の少なくとも1つの層、p型半導体材料の少なくとも1つの層、並びにp型及びn型半導体材料の層の間に配置されている少なくとも1つの放出性材料の放出性層を含み、
放出性層は、ホストマトリックス化合物としてカルバゾール誘導体、及びゲストエミッタとしてイリジウム錯体を含むブレンド材料を含む。
Xは、S、O、及びSeからなる群から選択され、
Ar及びAr'は、出現する毎に独立に、同一若しくは異なる単環式アリール基又はヘテロアリール基であり、
R1及びR2は、独立に、-CN、R3、-C(O)R4、及び-C(O)OR4からなる群から選択される同一若しくは異なる電子吸引基であり、R3は、1個又は複数のF又はCN基で置換されているアルキル基、アルケニル基、又はアルキニル基であり、R4は、1個又は複数のF又はCN基で任意選択で置換されているアルキル基、アルケニル基、又はアルキニル基であり、
m及びm'は、独立に、1又は2である。
誘電体層は、制御電極及びアセンブリの間に配置されており、
両極性チャネルは、n型半導体材料の少なくとも1つの層、p型半導体材料の少なくとも1つの層、並びにp型及びn型半導体材料の層の間に配置されている少なくとも1つの放出性材料の放出性層を含み、
放出性層は、ホストマトリックス化合物として有機カルバゾール誘導体、及びゲストエミッタとしてイリジウム錯体を含むブレンド材料から構成される。
of electrode work function with self-assembled layer:Interplay of energy barrier and tunneling distance on charge injection in organic light-emitting diodes」、Organic Electronics、12(4):602〜608頁(2011);Sungら、「AC Field-Induced Polymer Electroluminescence with Single Wall Carbon Nanotubes」、Nano Letters、11(3):966〜972頁(2011);Qiaoら、「Controlling charge balance and exciton recombination by bipolar host in single-layer organic light-emitting diodes」、Journal of Applied Physics、108(3):034508/1〜034508/8頁(2011);Khizar-ul-Haqら、「Blue organic light-emitting diodes with low driving voltage and enhanced power efficiency based on MoO3 as hole injection layer and optimized charge balance」、Journal of Non-Crystalline Solids、356(20〜22):1012〜1015頁(2010);Qiら、「Analysis of metal-oxide -based charge generation layers used in stacked organic light-emitting diodes」、Journal of Applied Physics、107(1):014514/1-014514/8頁(201);Huangら、「Materials and interface engineering in organic light-emitting diodes」、Organic Electronics、243〜261頁(2010);Helanderら、「Comparison of Alq3/alkali-metal fluoride/ Al cathodes for organic electroluminescent devices」、Journal of Applied Physics、104(9):094510/1〜094510/6頁(2008);Roy Choudhuryら、「LiF as an n-dopant in tris(8-hydroxyquinoline) aluminum thin films」、Advanced Materials、20(8):1456〜1461頁(2008);Vaccaら、「Poly(3,4-ethylenedioxythiophene):poly(4-styrenesulfonate) ratio:Structural, physical and hole injection properties in organic light emitting diodes」、Thin Solid Films、516(12):4232〜4237頁(2008);Yangら、「Improved fabrication process for enhancing light emission in single-layer organic light-emitting devices doped with organic salt」、Japanese Journal of Applied Physics、47(2, Pt. 1):1101〜1103頁(2008);Kimら、「UV-ozone surface treatment of indium-tin-oxide in organic light emitting diodes」、Journal of the Korean Physical Society、50(6):1858〜1861頁(2007);Pratら、「Stable, highly efficient and temperature resistant organic light-emitting devices」、Japanese Journal of Applied Physics, Part 1:Regular Papers, Brief Communications & Review Papers、46(4A):1727〜1730頁(2007);Luoら、「Improving the stability of organic light-emitting devices by using a hole-injection-tunable-anode-buffer-layer」、Journal of Applied Physics、101(5):054512/1〜054512/4頁(2007);Matsushimaら、「Charge-carrier injection characteristics at organic/organic heterojunction interfaces in organic light-emitting diodes」、Chemical Physics Letters、435(4〜6):327〜330頁(2007);Kimら、「Controllable work function of Li-Al alloy nanolayers for organic light-emitting devices」、Advanced Engineering Materials、7(11):1023〜1027頁(2005);Kato、「Designing Interfaces That Function to Facilitate Charge Injection in Organic Light-Emitting Diodes」、Journal of the American Chemical Society、127(33):11538〜11539頁(2005);Veinotら、「Toward the Ideal Organic Light-Emitting Diode. The Versatility and Utility of Interfacial Tailoring by Cross-Linked Siloxane Interlayers」、Accounts of Chemical Research、38(8):632〜643頁(2005);Oyamadaら、「Extremely low- voltage driving of organic light-emitting diodes with a Cs-doped phenyldipyrenylphosphine oxide layer as an electron-injection layer」、Applied Physics Letters、86(3):033503/1〜033503/3頁(2005);Hughesら、「Electron-transporting materials for organic electroluminescent and electrophosphorescent devices」、Journal of Materials Chemistry、15(1):94〜107頁(2005);D'Andradeら、「Efficient organic electrophosphorescent white-light-emitting device with a triple doped emissive layer」、Advanced Materials、16(7):624〜628頁(2004);Kannoら、「Development of OLED with high stability and luminance efficiency by co-doping methods for full color displays」、IEEE Journal of Selected Topics in Quantum Electronics、10(1):30〜36頁(2004);Hanら、「Transparent-cathode for top-emission organic light-emitting diodes」、Applied Physics Letters、82(16):2715〜2717頁(2003);Tutisら、「Internal electric field and charge distribution in multilayer organic light-emitting diodes」、Journal of Applied Physics、93(8):4594〜4602頁(2003);Mathaiら、「Controlled injection of holes into AlQ3 based OLEDs by means of an oxidized transport layer」、Materials Research Society Symposium Proceedings、708(Organic Optoelectronic Materials, Processing and Devices):101〜106頁(2002);Croneら、「Charge injection and transport in single-layer organic light-emitting diodes」、Applied Physics Letters、73(21):3162〜3164頁(1998);及びParkら、「Charge injection and photooxidation of single conjugated polymer molecules」、Journal of the American Chemical Society、126(13):4116〜7頁(2004)を参照されたい。
図1に関連して、本教示による有機両極性発光トランジスタ(OLET)をガラス基板(第1の層1)上に製作し、この上にITO(酸化インジウムスズ)でできた透明制御電極2を施した。450nm厚さのポリ(メタクリル酸メチル)(PMMA)から構成される誘電体層3を、スピンコーティングによってITO電極上に製作し、真空中で90℃にて硬化させた。有機放出性両極性チャネルを、昇華によって真空中(10ー7mbar)で誘電体層上に形成させたが、下記の層を含む。
- 誘電体層3の上に蒸着させたp型半導体材料から構成される正孔輸送層4、具体的には、基板を室温にて維持している間に0.1Å/sの速度で昇華させたC8-BTBTでできた15nm厚さの膜;
- 正孔輸送層4と接触している放出性層5、具体的には、ホスト-ゲスト系から構成される60nm厚さの再結合層(20%のゲストエミッタ濃度を有する)。TCTAをホストマトリックスとして使用し、これを、基板を室温にて維持している間に1Å/sの速度で昇華させた。Ir(piq)3をゲストエミッタとして使用し、これを、基板を室温にて維持している間に0.25Å/sの速度で昇華させた;及び
- 放出性層5と接触している電子輸送層6、具体的には、基板を室温にて維持している間に0.1Å/sの速度で昇華させた45nm厚さのN-F2-6の膜。
p型しきい電圧=-40.1V;
p型移動度=5.2×10ー1cm2/Vs;
n型しきい電圧=38.4V;
n型移動度=3.6×10ー3cm2/Vs。
異なるBTBT化合物を正孔輸送層4において使用したことを除いては、例1に記載したOLETと同じ様式で、及び同じ材料を使用して第2のOLETを製作した。具体的には、正孔輸送層4は、C8-BTBTの代わりにC5-BTBTでできた15nm厚さの膜から構成された。
p型しきい電圧=-54.5V;
p型-移動度=1.2×10-1cm2/Vs;
n型しきい電圧=25.9V;
n型移動度=4.2×10ー3cm2/Vs。
本例において試験した比較上のデバイスは、正孔輸送層4中にp型半導体材料としてDNTT化合物を組み込んだ。従前の報告は、DNTT化合物(チエノチオフェン中心のそれぞれの側に縮合させたナフタレン、すなわち、2個のベンゼン環を有する)が、これらの構造的な類似性にも関わらず、BTBT化合物(チエノチオフェン中心のそれぞれの側に縮合させた1個のみのベンゼン環を有する)より高い移動度を達成することができることを示唆してきた。例えば、M.J. Kangら、「Two Isomeric Didecyl-dinaphtho[2,3-b:2',3'-f]thieno[3,2-b]thiophenes:Impact of Alkylation Positions on Packing Structures and Organic Field Effect Transistor Characteristics」、Jpn. J. Appl. Phvs.、第51巻、11PD04頁(2012);及びH. Ebataら、「Highly Soluble [l]Benzothieno[3,2-b]benzothiophene(BTBT) Derivatives for High-Performance, Solution-Processed Organic Field-Effect Transistors」、J. Am. Chem. Soc、第129巻、15732〜15733頁(2007)を参照されたい。
p型しきい電圧=-40V;
p型-移動度=5×10ー5cm2/Vs;
n型しきい電圧=34V;
n型移動度=0.5cm2/Vs。
本例において試験した比較上のOLETデバイスは、R. Capelliら、「Organic light-emitting transistors with an efficiency that outperforms the equivalent light-emitting diodes」、Nature Materials、第9巻、496〜503頁(2010)において報告されている有機発光トランジスタにおいて使用されている、p型半導体材料(DH4T)、n型半導体材料(DFH4T、ビス(フルオロアルキル-置換)オリゴチオフェン)、及び放出性材料(Alq3:DCM)を組み込んだ。
- 誘電体層3上に蒸着させたn型半導体材料の電子輸送層4、具体的には、基板を室温にて維持している間に0.1Å/sの速度で昇華させたDFH4Tでできた、15nm厚さの膜の層;
- 正孔輸送層4と接触している放出性層5、具体的には、ホスト-ゲスト系から構成される60nm厚さの再結合層(20%のゲストエミッタ濃度を有する)。Alq3をホストマトリックスとして使用し、これを、基板を室温にて維持している間に1Å/sの速度で昇華させた。DCMをゲストエミッタとして使用し、これを、基板を室温にて維持している間に0.25Å/sの速度で昇華させた;及び
- 放出性層5と接触している正孔輸送層6、この場合、基板は室温にて維持する一方で0.1Å/sの速度で昇華させたDH4Tの45nm厚さの膜。
p型しきい電圧=-60V;
p型移動度=5.3×10ー1cm2/Vs;
n型しきい電圧=23.7V;
n型移動度=3.6×10ー3cm2/Vs。
本教示の別の態様は、3層OLETデバイスにおける放出性材料の使用を対象とし、放出性材料は、有機アリールアミンマトリックス化合物(H-1)又は(H-2)、並びに(G-1)、(G-2)、及び(G-3)から選択されるイリジウムをベースとするエミッタを含むブレンドである。
- 誘電体層3上に蒸着させたp型半導体材料から構成される正孔輸送層4、具体的には、基板を室温にて維持している間に0.1Å/sの速度で昇華させたDH4Tでできた45nm厚さの膜;
- 正孔輸送層4と接触している放出性層5、具体的には、ホスト-ゲスト系から構成される60nm厚さの再結合層(20%のゲストエミッタ濃度を有する)。TCTAをホストマトリックスとして使用し、これを、基板を室温にて維持している間に1Å/sの速度で昇華させた。Ir(piq)3をゲストエミッタとして使用し、これを、基板を室温にて維持している間に0.25Å/sの速度で昇華させた;及び
- 放出性層5と接触している電子輸送層6、具体的には、基板を室温にて維持している間に0.1Å/sの速度で昇華させたN-F4-1の45nm厚さの膜。
p型しきい電圧=-49V;
p型移動度=1.3×10ー1cm2/Vs;
n型しきい電圧=ゼロ;
n型移動度=ゼロ。
本例において、異なるブレンド材料を放出性層5において使用したことを除いては、例5に記載したOLETと同じ様式で、及び同じ材料を使用して比較上のOLETデバイスを製作した。具体的には、放出性層5は、Alq3:PtOEPから構成されるブレンド材料であった。すなわち、ホストマトリックス及びゲストエミッタの両方は、金属錯体であり、ゲストエミッタは、イリジウムをベースとする錯体の代わりに白金をベースとする錯体である。
p型しきい電圧=-55.2V;
p型-移動度=3.8×10-2cm2/Vs;
n型しきい電圧=ゼロ;
n型移動度=ゼロ。
2 制御電極
3 誘電体層
4 第1のタイプの半導体材料の層
5 放出性材料の層
6 第2のタイプの半導体材料の層
7 電子電極及び正孔電極
Claims (35)
- 少なくとも1つの誘電体層;少なくとも1つの制御電極;少なくとも1つの正孔電極;少なくとも1つの電子電極;及び放出性両極性チャネルを含むアセンブリを含む、有機エレクトロルミネッセンストランジスタであって、
前記誘電体層は、前記制御電極及び前記アセンブリの間に配置され、
前記放出性両極性チャネルは、n型半導体材料の少なくとも1つの層、p型半導体材料の少なくとも1つの層、並びにp型及びn型半導体材料の前記層の間に配置されている放出性材料の少なくとも1つの層を含み、
前記p型半導体材料は、一般式(P-I)
- Ra及びRbが、同一のC1〜18アルキル基である、請求項1から3のいずれか一項に記載の有機エレクトロルミネッセンストランジスタ。
- Ra及びRbが、同一のC3〜12アルキル基である、請求項1から3のいずれか一項に記載の有機エレクトロルミネッセンストランジスタ。
- Ra及びRbが、同一の直鎖状C3〜12アルキル基である、請求項5に記載の有機エレクトロルミネッセンストランジスタ。
- 前記n型半導体材料が、ビス(p-フルオロアルキル)フェニル-置換オリゴマーチオフェン化合物を含み、前記オリゴマーチオフェン化合物が、2、3、4、5又は6つのチオフェン部分を有し、任意選択でチオフェン部分の2つ以上が縮合されている、請求項1から7のいずれか一項に記載の有機エレクトロルミネッセンストランジスタ。
- 前記ビス(p-フルオロアルキル)フェニル-置換オリゴマーチオフェン化合物が、ジチオフェン、クアテルチオフェン、及びチエノチオフェンからなる群から選択される、請求項8に記載の有機エレクトロルミネッセンストランジスタ。
- p型半導体材料の前記層の厚さが、5〜50nmである、請求項1に記載の有機エレクトロルミネッセンストランジスタ。
- p型半導体材料の前記層の厚さが、15〜45nmである、請求項10に記載の有機エレクトロルミネッセンストランジスタ。
- n型半導体材料の前記層の厚さが、30nm〜60nmであることを特徴とする、請求項1に記載の有機エレクトロルミネッセンストランジスタ。
- 放出性材料の前記層が、30nm〜60nmの厚さを有することを特徴とする、請求項1に記載の有機エレクトロルミネッセンストランジスタ。
- 前記放出性材料が、ホストマトリックス化合物として有機カルバゾール誘導体、及びゲストエミッタとしてイリジウム錯体を含むブレンド材料を含む、請求項1から13のいずれか一項に記載の有機エレクトロルミネッセンストランジスタ。
- ソース電極が、p型半導体材料の前記層と接触しており、ドレイン電極が、n型半導体材料の前記層と接触している、請求項1に記載の有機エレクトロルミネッセンストランジスタ。
- ソース電極及びドレイン電極が、少なくとも1種の異なる材料から構成される、請求項1に記載の有機エレクトロルミネッセンストランジスタ。
- 注入副層が、ソース電極及びp型若しくはn型半導体材料の層の間に介在しており、かつ/又は注入副層が、ドレイン電極及びp型若しくはn型半導体材料の層の間に介在している、請求項1に記載の有機エレクトロルミネッセンストランジスタ。
- 制御電極、ドレイン電極、及びソース電極のそれぞれが、独立に、金、銀、モリブデン、銅、チタン、クロム、スズをドープした酸化インジウム及びこれらの組合せからなる群から選択される金属又は透明導電酸化物を含む、請求項1に記載の有機エレクトロルミネッセンストランジスタ。
- 前記誘電体層が、無機酸化物又は窒化物、分子誘電体、ポリマー誘電体、及びこれらの組合せからなる群から選択される電気絶縁材料を含む、請求項1に記載の有機エレクトロルミネッセンストランジスタ。
- 無機酸化物又は窒化物が、SiO2、Si3N4、Al2O3、ZrOx、AlをドープしたZrOx、及びHfOxからなる群から選択される、請求項1に記載の有機エレクトロルミネッセンストランジスタ。
- 前記放出性両極性チャネルの上面を覆うパシベーション層を更に含む、請求項1に記載の有機エレクトロルミネッセンストランジスタ。
- 互いに相互接続しており、基板上に蒸着されている、複数の同一若しくは異なる請求項1から21のいずれか一項に記載の有機エレクトロルミネッセンストランジスタを含む、画像を生成するためのオプトエレクトロニックデバイス。
- 少なくとも1つの誘電体層;少なくとも1つの制御電極;少なくとも1つの正孔電極;少なくとも1つの電子電極;及び放出性両極性チャネルを含むアセンブリを含む、有機エレクトロルミネッセンストランジスタであって、
前記誘電体層は、前記制御電極及び前記アセンブリの間に配置され、
前記放出性両極性チャネルは、n型半導体材料の少なくとも1つの層、p型半導体材料の少なくとも1つの層、並びにp型及びn型半導体材料の前記層の間に配置されている放出性材料の少なくとも1つの層を含み、
前記放出性材料は、ホストマトリックス化合物として有機カルバゾール誘導体、及びゲストエミッタとしてイリジウム錯体を含むブレンド材料を含む、有機エレクトロルミネッセンストランジスタ。 - 前記放出性材料が、青色発光性である、請求項23に記載の有機エレクトロルミネッセンストランジスタ。
- 前記放出性材料が、緑色発光性である、請求項23に記載の有機エレクトロルミネッセンストランジスタ。
- 前記放出性材料が、赤色発光性である、請求項23に記載の有機エレクトロルミネッセンストランジスタ。
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