JP2022513608A - 有機エレクトロルミネッセンス材料及びその調製方法並びに有機エレクトロルミネッセンスデバイス - Google Patents
有機エレクトロルミネッセンス材料及びその調製方法並びに有機エレクトロルミネッセンスデバイス Download PDFInfo
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- JP2022513608A JP2022513608A JP2021527097A JP2021527097A JP2022513608A JP 2022513608 A JP2022513608 A JP 2022513608A JP 2021527097 A JP2021527097 A JP 2021527097A JP 2021527097 A JP2021527097 A JP 2021527097A JP 2022513608 A JP2022513608 A JP 2022513608A
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- organic electroluminescence
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- electroluminescence material
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- 238000005401 electroluminescence Methods 0.000 title claims abstract description 44
- 239000000463 material Substances 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 12
- 239000010410 layer Substances 0.000 claims description 61
- -1 dehydrogen Chemical class 0.000 claims description 27
- 238000002347 injection Methods 0.000 claims description 16
- 239000007924 injection Substances 0.000 claims description 16
- 239000012044 organic layer Substances 0.000 claims description 15
- 230000005525 hole transport Effects 0.000 claims description 11
- 229940126062 Compound A Drugs 0.000 claims description 8
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 6
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- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
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- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical group COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 4
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- BCMGOTDNNMLUBS-UHFFFAOYSA-N 2-bromo-1,8-naphthyridine Chemical compound C1=CC=NC2=NC(Br)=CC=C21 BCMGOTDNNMLUBS-UHFFFAOYSA-N 0.000 claims description 3
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- 238000004020 luminiscence type Methods 0.000 claims 1
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- 238000010586 diagram Methods 0.000 abstract description 4
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- 230000008901 benefit Effects 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
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- SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 description 2
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- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 2
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- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 1
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- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
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- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
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- 238000002474 experimental method Methods 0.000 description 1
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- 229940095102 methyl benzoate Drugs 0.000 description 1
- OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
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- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
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- 150000003384 small molecules Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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- 238000004544 sputter deposition Methods 0.000 description 1
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/14—Carrier transporting layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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Abstract
Description
Arは、C6-C30の置換又は非置換のアリール、1つ又は複数のヘテロ原子を含むC5-C30の置換又は非置換のアリール、N-アリール置換のカルバゾリル、N-アリール置換のインデノカルバゾール誘導体置換基、ジアリールアミノ基、R1-R8置換のジアリールアミノ基及びその環状誘導体Cyから選択され、Cy中のZは、C(R9)2、Si(R9)2、O、S、NR9及びSO2から選択され、R1-R9はそれぞれ独立して水素、重水素、ハロゲン、非置換のアルキル、ハロゲン化アルキル、重水素化アルキル、シクロアルキル、非置換のアリール、アルキル置換のアリール、アルコキシ、シアノ、カルバゾリル及びジフェニルアミノのうちのいずれか、あるいは、R1-R9は独立して、隣接する基と5-8員環を形成し、
Lは、フェニレン、ビフェニレン及びナフチレンのうちから選択され、
Rは、水素、重水素、置換又は非置換のC6-C10のアリール並びにC6-C10のヘテロアリールのうちから選択される。
Arは、フェニル、ナフチル、ビフェニル、フェナントリル、アントリル、アリールアントリル、ピレニル、ジベンゾフラニル、ジベンゾチオフェニル、ベンズイミダゾリル、ピリミジニル、トリアジニル、キナゾリニル、1,2,4-トリアゾリル、N-フェニル-カルバゾリル、ジフェニルアミノ、アクリジニル及びアクリジン誘導体置換基のうちから選択されることが好ましい。
(1)化合物Aを提供するステップと、
(2)アルカリ性条件下で、テトラキストリフェニルホスフィンパラジウムを触媒として使用して、Ar含有ボロン酸化物又はAr含有ボロン酸ピナコールエステルを化合物Aと反応させて、式(I)の化合物を取得するステップとを含む。
A) n-ブチルリチウムの作用下で、2-ブロモ-1,8-ジナフチリジンとRのギ酸エステルを反応させて、化合物Bを取得する工程と、
B)化合物Bと臭化Lのホルムアルデヒド化合物CHO-L-Brを反応させて、化合物Aを取得する工程を含む。
Ar、L、Rの定義は上記のとおりである。
又は、有機層は、発光層、正孔注入層、正孔輸送層及び電子輸送層である。
又は、有機層は、発光層、正孔注入層、正孔輸送層、電子輸送層及び電子注入層である。
又は、有機層は、発光層、正孔輸送層、電子輸送層、電子注入層である。
又は、有機層は発光層、正孔輸送層、電子注入層である。
式(I)のイミダゾール[1,5-a][1,8]ナフチリジンに基づいた化合物が存在する層は発光層であることが好ましい。
式(I)のイミダゾール[1,5-a][1,8]ナフチリジンを含む化合物を発光デバイスの製造に使用する場合、単独で使用してもよく、他の化合物と混合して使用してもよく、式(I)の2つ以上の化合物を同時に使用してもよい。
中間体1の合成
三つ口フラスコに、2-ブロモ-1,8-ジナフチリジン(10g、47.84mmol)、無水THF(100ml)を入れ、窒素雰囲気下で、-50℃で20分間撹拌した。その後、定圧力滴下漏斗によってn-ブチルリチウムのn-ヘキサン溶液(2.2M、26ml、57mmol)を滴下添加した。添加が完了したら、温度を維持しながら30分間撹拌を続け、次に安息香酸メチルのTHF溶液(6.84g、50.2mmol)を滴下添加した。その後、ゆっくりと室温まで加熱し、一晩撹拌した。反応後、飽和塩化アンモニウム溶液で反応を停止させ、有機相を分離し、無機相を酢酸エチルで抽出し、有機相を合わせた。生成物をカラムクロマトグラフィーで精製して、7.7gを取得した。収率は71%であった。
フラスコに、中間体1(3g、12.8mmol)、p-ブロモベンズアルデヒド(2.37g、12.8mmol)、酢酸アンモニウム(29.6g、0.38mol)及び酢酸60mlを入れた。窒素雰囲気下で、130℃に加熱し、15時間反応させた。反応後、冷却し、減圧下で酢酸を除去し、水を加え、ジクロロメタンで抽出し、有機相を集め、乾燥及び濃縮して粗生成物を取得した。粗生成物をシリカゲルカラムクロマトグラフィーで精製して、3.5gを取得した。収率は70%であった。
フラスコに、中間体2(6g、25.5mmol)、m-ブロモベンズアルデヒド(4.7g、25.5mmol)、酢酸アンモニウム(49g、0.64mol)及び酢酸100mlを入れた。窒素雰囲気下で、130℃に加熱し、16時間反応させた。反応後、冷却し、減圧下で酢酸を除去し、水を加え、ジクロロメタンで抽出し、有機相を集め、乾燥及び濃縮して粗生成物を取得した。粗生成物をシリカゲルカラムクロマトグラフィーで精製して、6gを取得した。収率は59%であった。
丸底フラスコに中間体4(1g、2.5mmol)、2,4-二フェニル-6-((3-ボロン酸ピナコールエステル)フェニル)-1,3,5-トリアジン(1.2g、2.75mmol)、テトラキス(トリフェニルホスフィン)パラジウム(0.29g、0.25mmol)、炭酸カリウム(0.86g、6.2mmol)及びジオキサン/水(10ml/2ml)を入れた。反応混合物を窒素雰囲気で110℃に加熱し、10時間撹拌した。反応後、水で洗浄し、ジクロロメタンで抽出し、濃縮して粗生成物を取得し、シリカゲルカラムクロマトグラフィーで精製して、1.27gを取得した。收率は81%であった。Ms(ESI):629.2(M+1)。
丸底フラスコに中間体3(1g、2.5mmol)、N-フェニル-3-カルバゾールボロン酸(0.79g、2.75mmol)、テトラキス(トリフェニルホスフィン)パラジウム(0.29g、0.25mmol)、炭酸カリウム(0.86g、6.2mmol)及びトルエン/水(10ml/2ml)を入れた。反応混合物を窒素雰囲気で110℃に加熱し、8時間撹拌した。反応後、水で洗浄し、ジクロロメタンで抽出し、濃縮して粗生成物を取得し、シリカゲルカラムクロマトグラフィーで精製して、1.04gを取得した。收率は74%であった。Ms(ESI):563.2(M+1)。
丸底フラスコに中間体5(2g,5mmol)、(3-(10H-スピロ[アクリジン-9,9’-フルオレン]-10-イル)フェニル)ボロン酸(2.47g、6mmol)、テトラキス(トリフェニルホスフィン)パラジウム(0.58g、0.5mmol)、炭酸カリウム(1.7g、12.5mmol)及びジオキサン/水(20ml/4ml)を入れた。反応混合物を窒素雰囲気で110℃に加熱し、10時間撹拌した。
有機エレクトロルミネッセンスデバイスの製造
まず、透明な導電性膜(ITO膜)ガラス基板110(その上に陽極120がある)を脱イオン水、エタノール、アセトン、及び脱イオン水で順次洗浄し、次に、酸素プラズマで30秒間処理した。
本発明の化合物に代えて、CBPを発光層として使用した他すべて実施例4と同様とした。
Claims (13)
- 有機エレクトロルミネッセンス材料であって、式(I)の構造を有し、
Arは、C6-C30の置換又は非置換のアリール、1つ又は複数のヘテロ原子を含むC5-C30の置換又は非置換のアリール、N-アリール置換のカルバゾリル、N-アリール置換のインデノカルバゾール誘導体置換基、ジアリールアミノ基、R1-R8置換のジアリールアミノ基及びその環状誘導体Cyから選択され、Cy中のZは、C(R9)2、Si(R9)2、O、S、NR9及びSO2のうちから選択され、R1-R9はそれぞれ独立して水素、重水素、ハロゲン、非置換のアルキル、ハロゲン化アルキル、重水素化アルキル、シクロアルキル、非置換のアリール、アルキル置換のアリール、アルコキシ、シアノ、カルバゾリル及びジフェニルアミノのいずれか、あるいは、R1-R9はそれぞれ独立して、隣接する基と5-8員環を形成し、
Lは、フェニレン、ビフェニレン及びナフチレンのうちから選択され、
Rは、水素、重水素、置換又は非置換のC6-C10のアリール及びC6-C10のヘテロアリールのうちから選択される、ことを特徴とする有機エレクトロルミネッセンス材料。 - Arは、フェニル、ナフチル、ビフェニル、フェナントリル、アントリル、アリールアントリル、ピレニル、ジベンゾフラニル、ジベンゾチオフェニル、ベンズイミダゾリル、ピリジル、ピリミジニル、キノリル、イソキノリル、トリアジニル、ピロリル、フリル、チアゾリル、キナゾリニル、トリアゾリル、ベンゾチアゾリル、ベンゾチアジアゾリル、1,2,4-トリアゾリル、ジフェニルアミノ、アリールカルバゾリル、N-アリール置換のカルバゾリル、ジフェニルアミノ、アクリジニル及アクリジン誘導体置換基、フェノキサジニイル及びその誘導体置換基並びにフェノチアジニル及びその誘導体置換基のうちから選択され、Rは、水素、フェニル、ナフチル及びピリジルのうちから選択される、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材料。
- Arは、フェニル、ナフチル、ビフェニル、フェナントリル、アントリル、アリールアントリル、ピレニル、ジベンゾフラニル、ジベンゾチオフェニル、ベンズイミダゾリル、ピリミジニル、トリアジニル、キナゾリニル、1,2,4-トリアゾリル、N-フェニル-カルバゾリル、ジフェニルアミノ並びにアクリジニル及びアクリジン誘導体置換基から選択される、ことを特徴とする請求項2に記載の有機エレクトロルミネッセンス材料。
- 前記化合物Aの調製方法は、
A) n-ブチルリチウムの作用下で、2-ブロモ-1,8-ジナフチリジンとRのギ酸エステルを反応させて、化合物Bを取得する工程と、
B)化合物Bと臭化Lのホルムアルデヒド化合物CHO-L-Brを反応させて、化合物Aを取得する工程を含む、ことを特徴とする請求項6に記載の調製方法 - 前記Rのギ酸エステルは、Rのギ酸メチルである、ことを特徴とする請求項7に記載の調製方法。
- 請求項1~5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材料の有機エレクトロルミネッセンスデバイスにおける使用。
- 陽極、陰極及び有機層を含み、有機層は、発光層、正孔注入層、正孔輸送層、電子注入層及び電子輸送層のうちの少なくとも1つの層を含み、前記有機層の少なくとも1つの層は、請求項1~5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材料を含む、ことを特徴とする有機エレクトロルミネッセンスデバイス。
- 請求項1~5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材料を含む層は発光層である、ことを特徴とする請求項10に記載の有機エレクトロルミネッセンスデバイス。
- 請求項1~5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材料は発光層において、単独で、又は他の化合物と混合して使用される、ことを特徴とする請求項11に記載の有機エレクトロルミネッセンスデバイス。
- 前記有機層は、1~1000nmの総厚を有し、真空蒸着法、分子線蒸着法、溶媒に溶解されるディップコーティング法、バーコーティング法又はインクジェット印刷法によって調製される、ことを特徴とする請求項10に記載の有機エレクトロルミネッセンスデバイス。
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