JP7275042B2 - 有機金属錯体、発光素子、発光装置、電子機器および照明装置 - Google Patents
有機金属錯体、発光素子、発光装置、電子機器および照明装置 Download PDFInfo
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- JP7275042B2 JP7275042B2 JP2019554055A JP2019554055A JP7275042B2 JP 7275042 B2 JP7275042 B2 JP 7275042B2 JP 2019554055 A JP2019554055 A JP 2019554055A JP 2019554055 A JP2019554055 A JP 2019554055A JP 7275042 B2 JP7275042 B2 JP 7275042B2
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- 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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- 239000000057 synthetic resin Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- DKWSBNMUWZBREO-UHFFFAOYSA-N terbium Chemical compound [Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb] DKWSBNMUWZBREO-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JIIYLLUYRFRKMG-UHFFFAOYSA-N tetrathianaphthacene Chemical compound C1=CC=CC2=C3SSC(C4=CC=CC=C44)=C3C3=C4SSC3=C21 JIIYLLUYRFRKMG-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
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- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 239000012780 transparent material Substances 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
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- HSSMNYDDDSNUKH-UHFFFAOYSA-K trichlororhodium;hydrate Chemical compound O.Cl[Rh](Cl)Cl HSSMNYDDDSNUKH-UHFFFAOYSA-K 0.000 description 1
- QGJSAGBHFTXOTM-UHFFFAOYSA-K trifluoroerbium Chemical compound F[Er](F)F QGJSAGBHFTXOTM-UHFFFAOYSA-K 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
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- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Images
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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/80—Constructional details
- H10K59/875—Arrangements for extracting light from the devices
- H10K59/876—Arrangements for extracting light from the devices comprising a resonant cavity structure, e.g. Bragg reflector pair
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Description
本実施の形態では、本発明の一態様である有機金属錯体について説明する。
まず、上記一般式(G1)に含まれるピリミジン誘導体(一般式(G0))の合成方法について説明する。
上記一般式(G0)で表されるピリミジン誘導体は、下記合成スキーム(A-1)に示すように、ハロゲン化ベンゼン誘導体(A1)をアルキルリチウム等でリチオ化し、ピリミジンのハロゲン化物(A2)と反応させることにより得ることができる。
上記一般式(G0)で表されるピリミジン誘導体は、下記合成スキーム(A-1’)に示すように、ベンゼン誘導体のボロン酸(A1’)とピリミジンのハロゲン化物(A2’)とをカップリングすることにより得ることができる。
上記一般式(G0)で表されるピリミジン誘導体は、下記合成スキーム(A-1’’)に示すように、ベンゼン誘導体置換のジケトン(A1’’)とホルムアミド(A2’’)とをマイクロ波を用いて反応させることにより得ることができる。
上記一般式(G1-1)で表される有機金属錯体の合成方法について説明する。
上記一般式(G1-2)で表される有機金属錯体の合成方法について説明する。
本実施の形態では、本発明の一態様である発光素子について説明する。なお、本実施の形態で説明する発光素子には、本発明の一態様である有機金属錯体を用いることができる。
図1(A)には、一対の電極間にEL層を挟んでなる発光素子を示す。具体的には、第1の電極101と第2の電極102との間に発光層を含むEL層103が挟まれた構造を有する。
次に、本発明の一態様である発光素子の具体的な構造および作製方法について説明する。なお、図1(A)~図1(E)において、符号が共通である場合は説明も共通とする。
第1の電極101および第2の電極102を形成する材料としては、上述した素子構造における両電極の機能が満たせるのであれば、以下に示す材料を適宜組み合わせて用いることができる。例えば、金属、合金、電気伝導性化合物、およびこれらの混合物などを適宜用いることができる。具体的には、In-Sn酸化物(ITOともいう)、In-Si-Sn酸化物(ITSOともいう)、In-Zn酸化物、In-W-Zn酸化物が挙げられる。その他、アルミニウム(Al)、チタン(Ti)、クロム(Cr)、マンガン(Mn)、鉄(Fe)、コバルト(Co)、ニッケル(Ni)、銅(Cu)、ガリウム(Ga)、亜鉛(Zn)、インジウム(In)、スズ(Sn)、モリブデン(Mo)、タンタル(Ta)、タングステン(W)、パラジウム(Pd)、金(Au)、白金(Pt)、銀(Ag)、イットリウム(Y)、ネオジム(Nd)などの金属、およびこれらを適宜組み合わせて含む合金を用いることもできる。その他、上記例示のない元素周期表の第1族または第2族に属する元素(例えば、リチウム(Li)、セシウム(Cs)、カルシウム(Ca)、ストロンチウム(Sr))、ユウロピウム(Eu)、イッテルビウム(Yb)などの希土類金属およびこれらを適宜組み合わせて含む合金、その他グラフェン等を用いることができる。
正孔注入層(111、111a、111b)は、陽極である第1の電極101や電荷発生層(104)からEL層(103、103a、103b)に正孔(ホール)を注入する層であり、正孔注入性の高い材料を含む層である。
発光層(113、113a、113b、113c)は、発光物質を含む層である。なお、発光物質としては、青色、紫色、青紫色、緑色、黄緑色、黄色、橙色、赤色などの発光色を呈する物質を適宜用いる。また、複数の発光層(113a、113b、113c)に異なる発光物質を用いることにより異なる発光色を呈する構成(例えば、補色の関係にある発光色を組み合わせて得られる白色発光)とすることができる。さらに、一つの発光層が異なる発光物質を有する積層構造であっても良い。
電子輸送層(114、114a、114b)は、電子注入層(115、115a、115b)によって、第2の電極102や電荷発生層(104)から注入された電子を発光層(113、113a、113b)に輸送する層である。なお、電子輸送層(114、114a、114b)は、電子輸送性材料を含む層である。電子輸送層(114、114a、114b)に用いる電子輸送性材料は、1×10-6cm2/Vs以上の電子移動度を有する物質が好ましい。なお、正孔よりも電子の輸送性の高い物質であれば、これら以外のものを用いることができる。
電子注入層(115、115a、115b)は、電子注入性の高い物質を含む層である。電子注入層(115、115a、115b)には、フッ化リチウム(LiF)、フッ化セシウム(CsF)、フッ化カルシウム(CaF2)、リチウム酸化物(LiOx)等のようなアルカリ金属、アルカリ土類金属、またはそれらの化合物を用いることができる。また、フッ化エルビウム(ErF3)のような希土類金属化合物を用いることができる。また、電子注入層(115、115a、115b)にエレクトライドを用いてもよい。エレクトライドとしては、例えば、カルシウムとアルミニウムの混合酸化物に電子を高濃度添加した物質等が挙げられる。なお、上述した電子輸送層(114、114a、114b)を構成する物質を用いることもできる。
図1(D)に示す発光素子において、電荷発生層104は、第1の電極(陽極)101と第2の電極(陰極)102との間に電圧を印加したときに、EL層103aに電子を注入し、EL層103bに正孔を注入する機能を有する。なお、電荷発生層104は、正孔輸送性材料に電子受容体(アクセプター)が添加された構成であっても、電子輸送性材料に電子供与体(ドナー)が添加された構成であってもよい。また、これらの両方の構成が積層されていても良い。なお、上述した材料を用いて電荷発生層104を形成することにより、EL層が積層された場合における駆動電圧の上昇を抑制することができる。
本実施の形態で示した発光素子は、様々な基板上に形成することができる。なお、基板の種類は、特定のものに限定されることはない。基板の一例としては、半導体基板(例えば単結晶基板又はシリコン基板)、SOI基板、ガラス基板、石英基板、プラスチック基板、金属基板、ステンレス・スチル基板、ステンレス・スチル・ホイルを有する基板、タングステン基板、タングステン・ホイルを有する基板、可撓性基板、貼り合わせフィルム、繊維状の材料を含む紙、又は基材フィルムなどが挙げられる。
本実施の形態では、本発明の一態様である発光装置について説明する。なお、図2(A)に示す発光装置は、第1の基板201上のトランジスタ(FET)202と発光素子(203R、203G、203B、203W)が電気的に接続されてなるアクティブマトリクス型の発光装置であり、複数の発光素子(203R、203G、203B、203W)は、共通のEL層204を有し、また、各発光素子の発光色に応じて、各発光素子の電極間の光学距離が調整されたマイクロキャビティ構造を有する。また、EL層204から得られた発光が第2の基板205に形成されたカラーフィルタ(206R、206G、206B)を介して射出されるトップエミッション型の発光装置である。
本実施の形態では、本発明の一態様である発光装置について説明する。
本実施の形態では、本発明の一態様である発光素子、本発明の一態様である発光素子を有する発光装置を適用して完成させた様々な電子機器や自動車の一例について、説明する。なお、発光装置は、本実施の形態で説明する電子機器において、主に表示部に適用することができる。
本実施の形態では、本発明の一態様である発光装置、またはその一部である発光素子を適用して作製される照明装置の構成について図7を用いて説明する。
本実施例では、実施の形態1の構造式(100)で表される本発明の一態様である有機金属錯体、ビス{2-[6-(4-シアノ-2,6-ジメチルフェニル)-4-ピリミジニル-κN3]フェニル-κC}(2,4-ペンタンジオナト-κO,O’)イリジウム(III)(略称:[Ir(ppm-dmCP)2(acac)])の合成方法について説明する。なお、[Ir(ppm-dmCP)2(acac)]の構造を以下に示す。
4-ブロモ-3,5-ジメチルベンゾニトリル10.06g、ビス(ピナコラート)ジボロン18.35g、酢酸カリウム21.73g、ジメチルスルホキシド240mLを、還流管を付けた三口フラスコに入れ、内部を窒素置換した。フラスコ内を減圧下で撹拌することで脱気した後、[1,1’-ビス(ジフェニルホスフィノ)フェロセン]パラジウム(II)ジクロリドジクロロメタン付加物(略称:Pd(dppf)Cl2・CH2Cl2)0.59g、2-ジシクロヘキシルホスフィノ-2’,6’-ジメトキシビフェニル(略称:S-Phos)0.59gを加え、100℃で32時間半撹拌した。所定時間経過後、トルエンによる抽出を行った。その後、ヘキサン:酢酸エチル=10:1を展開溶媒とするシリカゲルカラムクロマトグラフィーで精製し、目的物を得た(白色固体、収量5.89g、収率48%)。ステップ1の合成スキームを下記式(a-1)に示す。
次に、4-クロロ-6-フェニルピリミジン0.74g、上記ステップ1で得られた、3,5-ジメチル-4-(4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン-2-イル)ベンゾニトリル1.28g、リン酸三カリウム3.23g、トルエン43mL、水4.3mLを、還流管を付けた三口フラスコに入れ、内部を窒素置換した。
次に、2-エトキシエタノール15mLと水5mL、上記ステップ2で得たHppm-dmCP1.60g、塩化イリジウム水和物(IrCl3・H2O)(フルヤ金属社製)0.81gを、還流管を付けたナスフラスコに入れ、フラスコ内をアルゴン置換した。その後、マイクロ波(2.45GHz 100W)を3時間照射し、反応させた。所定時間経過後、得られた残渣をメタノールで吸引ろ過、洗浄し、複核錯体[Ir(ppm-dmCP)2Cl]2を得た(橙色固体、収量1.45g、収率67%)。ステップ3の合成スキームを下記式(a-3)に示す。
2-エトキシエタノール20mL、上記ステップ3で得た複核錯体、[Ir(ppm-dmCP)2Cl]2 1.44g、アセチルアセトン(略称:Hacac)0.41g、炭酸ナトリウム0.93gを、還流管を付けたナスフラスコに入れ、フラスコ内をアルゴン置換した。その後、マイクロ波(2.45GHz 100W)を4時間照射した。得られた残渣を、ジクロロメタンで吸引ろ過した後、濾液を濃縮した。得られた固体を、ヘキサン:酢酸エチル=2:1を展開溶媒とするシリカゲルカラムクロマトグラフィーにより精製した後、ジクロロメタンとメタノールの混合溶媒にて再結晶することにより、有機金属錯体、[Ir(ppm-dmCP)2(acac)]を黄橙色粉末として得た(収量0.19g、収率7%)。得られた黄橙色粉末0.19gを、トレインサブリメーション法により昇華精製した。昇華精製条件は、圧力2.7Pa、アルゴンガスを流量11mL/minで流しながら、355℃で固体を加熱した。昇華精製後、目的物の黄橙色固体を収量0.092g、収率48%で得た。ステップ4の合成スキームを下記式(a-4)に示す。
本実施例で示す発光素子は、図10に示すように基板900上に形成された第1の電極901上に正孔注入層911、正孔輸送層912、発光層913、電子輸送層914、電子注入層915が順次積層され、電子注入層915上に第2の電極903が積層された構造を有する。
作製した各発光素子の動作特性について測定した。なお、測定は室温(25℃に保たれた雰囲気)で行った。また、結果を図11~図14に示す。
本実施例では、実施の形態1の構造式(112)で表される本発明の一態様である有機金属錯体、ビス{4,6-ジメチル-2-[6-(5-シアノ-2-メチルフェニル)-4-ピリミジニル-κN3]フェニル-κC}(2,2,6,6-テトラメチル-3,5-ヘプタンジオナト-κ2O,O’)イリジウム(III)(略称:[Ir(dmppm-m5CP)2(dpm)])の合成方法について説明する。なお、[Ir(dmppm-m5CP)2(dpm)]の構造を以下に示す。
4,6-ジクロロピリミジン8.97g、3,5-ジメチルフェニルボロン酸9.01g、2M炭酸ナトリウム水溶液95mL、エチレングリコールジメチルエーテル(略称:DME)360mLを、還流管を付けた三口フラスコに入れ、内部を窒素置換した。フラスコ内を減圧下で撹拌することで脱気した後、酢酸パラジウム(II)(略称:Pd(OAc)2)0.67g、トリフェニルホスフィン(略称:PPh3)1.61gを加え、110℃で11時間撹拌した。所定時間経過後、酢酸エチルによる抽出を行った。その後、ジクロロメタンを展開溶媒とするシリカゲルカラムクロマトグラフィーで精製し、目的物を得た(黄白色固体、収量7.60g、収率58%)。ステップ1の合成スキームを下記式(b-1)に示す。
次に、上記ステップ1で得られた4-クロロ-6-(3,5-ジメチルフェニル)ピリミジン5.21g、5-シアノ-2-メチルフェニルボロン酸5.00g、リン酸三カリウム15.32g、トルエン240mL、水24mLを、還流管を付けた三口フラスコに入れ、内部を窒素置換した。
次に、2-エトキシエタノール30mLと水10mL、上記ステップ2で得たHdmppm-m5CP(略称)3.92g、塩化イリジウム水和物(IrCl3・H2O)(フルヤ金属社製)1.81gを、還流管を付けたナスフラスコに入れ、フラスコ内をアルゴン置換した。その後、マイクロ波(2.45GHz 100W)を3時間半照射し、反応させた。所定時間経過後、得られた残渣をメタノールで吸引ろ過、洗浄し、複核錯体[Ir(dmppm-m5CP)2Cl]2を得た(橙色固体、収量4.49g、収率91%)。また、ステップ3の合成スキームを下記式(b-3)に示す。
次に、2-エトキシエタノール20mL、上記ステップ3で得た複核錯体、[Ir(dmppm-m5CP)2Cl]2 4.48g、ジピバロイルメタン(略称:Hdpm)1.51g、炭酸ナトリウム2.90gを、還流管を付けたナスフラスコに入れ、フラスコ内をアルゴン置換した。
本実施例では、実施の形態1の構造式(114)で表される本発明の一態様である有機金属錯体、ビス{4,6-ジメチル-2-[6-(2-シアノ-6-メチルフェニル)-4-ピリミジニル-κN3]フェニル-κC}(2,2,6,6-テトラメチル-3,5-ヘプタンジオナト-κ2O,O’)イリジウム(III)(略称:[Ir(dmppm-m2CP)2(dpm)])の合成方法について説明する。なお、[Ir(dmppm-m2CP)2(dpm)]の構造を以下に示す。
4-クロロ-6-(3,5-ジメチルフェニル)ピリミジン2.18g、3-メチル-2-(テトラメチル-1,3,2-ジオキサボロラン-2-イル)ベンゾニトリル2.90g、リン酸三カリウム6.36g、トルエン100mL、水10mLを、還流管を付けた三口フラスコに入れ、内部を窒素置換した。
次に、2-エトキシエタノール30mLと水10mL、上記ステップ1で得たHdmppm-m2CP(略称)2.08g、塩化イリジウム水和物(IrCl3・H2O)(フルヤ金属社製)1.01gを、還流管を付けたナスフラスコに入れ、フラスコ内をアルゴン置換した。その後、マイクロ波(2.45GHz 100W)を2時間照射し、反応させた。所定時間経過後、得られた残渣をメタノールで吸引ろ過、洗浄し、複核錯体[Ir(dmppm-m2CP)2Cl]2を得た(赤茶色固体、収量1.88g、収率69%)。また、ステップ2の合成スキームを下記式(c-2)に示す。
次に、2-エトキシエタノール30mL、上記ステップ2で得た複核錯体、[Ir(dmppm-m2CP)2Cl]2 1.86g、ジピバロイルメタン(略称:Hdpm)0.61g、炭酸ナトリウム1.18gを、還流管を付けたナスフラスコに入れ、フラスコ内をアルゴン置換した。その後、マイクロ波(2.45GHz 100W)を5時間照射した。得られた残渣を、ジクロロメタンで吸引ろ過した後、濾液を濃縮した。得られた固体を、ジクロロメタンを展開溶媒とするシリカゲルカラムクロマトグラフィーにより精製することにより、有機金属錯体、[Ir(dmppm-m2CP)2(dpm)]を赤色固体として得た(収量0.050g、収率2%)。ステップ3の合成スキームを下記式(c-3)に示す。
本実施例では、実施の形態1の構造式(117)で表される本発明の一態様である有機金属錯体、ビス{4,6-ジメチル-2-[6-(2,6-ジシアノフェニル)-4-ピリミジニル-κN3]フェニル-κC}(2,2,6,6-テトラメチル-3,5-ヘプタンジオナト-κO,O’)イリジウム(III)(略称:[Ir(dmppm-dCP)2(dpm)])の合成方法について説明する。なお、[Ir(dmppm-dCP)2(dpm)]の構造を以下に示す。
Claims (13)
- 一般式(G1)で表される有機金属錯体。
(一般式(G1)中、R1~R4は、それぞれ独立に、水素、炭素数1~6のアルキル基、環を形成する炭素数が5~7の置換もしくは無置換のシクロアルキル基、環を形成する炭素数が6~13の置換もしくは無置換のアリール基、または環を形成する炭素数が3~12の置換もしくは無置換のヘテロアリール基のいずれかを表す。また、R5~R9は、それぞれ独立に、水素、炭素数1~6のアルキル基、環を形成する炭素数が6~13の置換もしくは無置換のアリール基、環を形成する炭素数が3~12の置換もしくは無置換のヘテロアリール基、またはシアノ基のいずれかを表し、少なくとも一は、シアノ基を表す。また、Lは、モノアニオン性の配位子を表す。また、nは、1乃至3の整数を表す。) - 一般式(G1)で表される有機金属錯体。
(一般式(G1)中、R1~R4は、それぞれ独立に、水素、炭素数1~6のアルキル基、環を形成する炭素数が5~7の置換もしくは無置換のシクロアルキル基、環を形成する炭素数が6~13の置換もしくは無置換のアリール基、または環を形成する炭素数が3~12の置換もしくは無置換のヘテロアリール基のいずれかを表す。また、R5~R9は、それぞれ独立に、水素、炭素数1~6のアルキル基、環を形成する炭素数が6~13の置換もしくは無置換のアリール基、環を形成する炭素数が3~12の置換もしくは無置換のヘテロアリール基、またはシアノ基のいずれかを表す。また、R6~R8のいずれか一は、シアノ基を表す。また、Lは、モノアニオン性の配位子を表す。また、nは、1乃至3の整数を表す。) - 請求項1または請求項2において、
前記モノアニオン性の配位子は、β-ジケトン構造を有するモノアニオン性の二座キレート配位子、カルボキシル基を有するモノアニオン性の二座キレート配位子、フェノール性水酸基を有するモノアニオン性の二座キレート配位子、二つの配位元素がいずれも窒素であるモノアニオン性の二座キレート配位子、またはシクロメタル化によりイリジウムと金属-炭素結合を形成する芳香族複素環二座配位子のいずれか一である有機金属錯体。 - 請求項1または請求項2において、
前記モノアニオン性の配位子は、下記一般式(L1)~(L8)のいずれか一である有機金属錯体。
(式中、R71~R77およびR87~R131は、それぞれ独立に水素、炭素数1~6のアルキル基、環を形成する炭素数が5~7の置換もしくは無置換のシクロアルキル基、ハロゲン基、ビニル基、置換もしくは無置換の炭素数1~6のハロアルキル基、置換もしくは無置換の炭素数1~6のアルコキシ基、置換もしくは無置換の炭素数1~6のアルキルチオ基、または環を形成する炭素数が6~13の置換もしくは無置換のアリール基を表す。また、A1~A3は、それぞれ独立に窒素もしくは水素と結合するsp2混成炭素、または置換基を有するsp2混成炭素を表し、前記置換基は炭素数1~6のアルキル基、ハロゲン基、炭素数1~6のハロアルキル基、または置換もしくは無置換のフェニル基のいずれかを表す。) - 一般式(G2)で表される有機金属錯体。
(一般式(G2)中、R1~R4は、それぞれ独立に、水素、炭素数1~6のアルキル基、環を形成する炭素数が5~7の置換もしくは無置換のシクロアルキル基、環を形成する炭素数が6~13の置換もしくは無置換のアリール基、環を形成する炭素数が3~12の置換もしくは無置換のヘテロアリール基のいずれかを表す。また、R5~R9は、それぞれ独立に、水素、炭素数1~6のアルキル基、環を形成する炭素数が6~13の置換もしくは無置換のアリール基、環を形成する炭素数が3~12の置換もしくは無置換のヘテロアリール基、シアノ基のいずれかを表し、少なくとも一は、シアノ基を表す。また、R71およびR73は、それぞれ独立に水素、炭素数1~6のアルキル基、環を形成する炭素数が5~7の置換もしくは無置換のシクロアルキル基、ハロゲン基、ビニル基、置換もしくは無置換の炭素数1~6のハロアルキル基、置換もしくは無置換の炭素数1~6のアルコキシ基、置換もしくは無置換の炭素数1~6のアルキルチオ基、または環を形成する炭素数が6~13の置換もしくは無置換のアリール基を表す。) - 一般式(G2)で表される有機金属錯体。
(一般式(G2)中、R1~R4は、それぞれ独立に、水素、炭素数1~6のアルキル基、環を形成する炭素数が5~7の置換もしくは無置換のシクロアルキル基、環を形成する炭素数が6~13の置換もしくは無置換のアリール基、または環を形成する炭素数が3~12の置換もしくは無置換のヘテロアリール基のいずれかを表す。また、R5~R9は、それぞれ独立に、水素、炭素数1~6のアルキル基、環を形成する炭素数が6~13の置換もしくは無置換のアリール基、環を形成する炭素数が3~12の置換もしくは無置換のヘテロアリール基、またはシアノ基のいずれかを表す。また、R6~R8のいずれか一は、シアノ基を表す。また、R71およびR73は、それぞれ独立に水素、炭素数1~6のアルキル基、環を形成する炭素数が5~7の置換もしくは無置換のシクロアルキル基、ハロゲン基、ビニル基、置換もしくは無置換の炭素数1~6のハロアルキル基、置換もしくは無置換の炭素数1~6のアルコキシ基、置換もしくは無置換の炭素数1~6のアルキルチオ基、または環を形成する炭素数が6~13の置換もしくは無置換のアリール基を表す。) - 請求項1乃至請求項7のいずれか一に記載の有機金属錯体を用いた発光素子。
- 一対の電極間に発光層を有し、
前記発光層は、請求項1乃至請求項7のいずれか一に記載の有機金属錯体を有する発光素子。 - 一対の電極間に発光層を有し、
前記発光層は、複数の有機化合物を有し、
前記複数の有機化合物のうち一は、請求項1乃至請求項7のいずれか一に記載の有機金属錯体である発光素子。 - 請求項8乃至請求項10のいずれか一に記載の発光素子と、トランジスタまたは基板と、を有する発光装置。
- 請求項11に記載の発光装置と、
マイク、カメラ、操作用ボタン、外部接続部、または、スピーカと、を有する電子機器。 - 請求項11に記載の発光装置と、
筐体、カバー、または、支持台と、を有する照明装置。
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