JP2011509247A - リン光発光ダイオード中の、カルバゾールを含む物質 - Google Patents
リン光発光ダイオード中の、カルバゾールを含む物質 Download PDFInfo
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- JP2011509247A JP2011509247A JP2010540808A JP2010540808A JP2011509247A JP 2011509247 A JP2011509247 A JP 2011509247A JP 2010540808 A JP2010540808 A JP 2010540808A JP 2010540808 A JP2010540808 A JP 2010540808A JP 2011509247 A JP2011509247 A JP 2011509247A
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- pyridine
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- dibenzothiophene
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- 0 CCCC(C)(*1c2ccccc2-c2ccccc12)c1cc(-c2c(*3C(C)=C)cccc2)c3cc1 Chemical compound CCCC(C)(*1c2ccccc2-c2ccccc12)c1cc(-c2c(*3C(C)=C)cccc2)c3cc1 0.000 description 4
- QAXFTXJQBYYMPM-UHFFFAOYSA-N CCC(C)(c(cc1)cc2c1[n](C(C)(CC)c(cc1)cc(c3c4cccc3)c1[n]4-c(cc1)cc3c1[o]c1c3cccc1)c1c2cccc1)[n]1c2ccccc2c2c1cccc2 Chemical compound CCC(C)(c(cc1)cc2c1[n](C(C)(CC)c(cc1)cc(c3c4cccc3)c1[n]4-c(cc1)cc3c1[o]c1c3cccc1)c1c2cccc1)[n]1c2ccccc2c2c1cccc2 QAXFTXJQBYYMPM-UHFFFAOYSA-N 0.000 description 2
- ZTVNTEFNZDVANN-UHFFFAOYSA-N CCC(C)(c1ccc2[n](C(C)(CC)c(cc3c4c5cccc4)ccc3[n]5-c3c4[o]c5ccccc5c4ccc3)c(cccc3)c3c2c1)[n]1c2ccccc2c2c1cccc2 Chemical compound CCC(C)(c1ccc2[n](C(C)(CC)c(cc3c4c5cccc4)ccc3[n]5-c3c4[o]c5ccccc5c4ccc3)c(cccc3)c3c2c1)[n]1c2ccccc2c2c1cccc2 ZTVNTEFNZDVANN-UHFFFAOYSA-N 0.000 description 1
- VQUUHMHOLAOJTK-UHFFFAOYSA-N c(cc1)cc(c2ccccc22)c1[n]2-c(cc1)cc(c2c3cccc2)c1[n]3-c(cc12)ccc1[o]c1c2nccc1 Chemical compound c(cc1)cc(c2ccccc22)c1[n]2-c(cc1)cc(c2c3cccc2)c1[n]3-c(cc12)ccc1[o]c1c2nccc1 VQUUHMHOLAOJTK-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
新しい群の、カルバゾールを含む化合物を提供する。特に、単分散の線状の3,9−連結オリゴカルバゾリルを有する化合物(本明細書では「オリゴカルバゾール」という)を提供する。
一般に、OLEDは、アノードとカソードの間に配置され且つ電気的にそれらに接続された少なくとも1つの有機層を含む。電流が流された場合、その有機層(1又は複数)にアノードは正孔を注入し、カソードは電子を注入する。注入された正孔と電子は、それぞれ、反対に帯電した電極に向かって移動する。電子と正孔が同じ分子上に局在すると、励起エネルギー状態を有する局在化した電子-正孔対である「励起子」が形成される。この励起子が発光機構によって緩和するときに光が発せられる。いくつかの場合には、励起子はエキシマー又はエキシプレックス上に局在しうる。非発光機構、例えば熱的緩和も起こりうるが、一般には望ましくないと考えられる。
及び、Baldoら,“Very high-efficiency green organic light-emitting devices based on electrophosphorescence”, Appl. Phys. Lett., vol. 75, No. 3, 4-6 (1999)(“Baldo-II”)、これらを参照により全体を援用する。リン光は、米国特許第7,279, 704号明細書の第5〜6欄により詳細に記載されており、これを参照により援用する。
いくつかのカルバゾール含有化合物を以下のように合成した。
固体のKI(22.1 g, 133 mmol)を550mLの酢酸中、カルバゾール(33.4 g, 200 mmol)に添加した。この混合物は、120℃に30分間加熱した後、透明になった。それを100℃に冷やして戻し、KIO3(21.4 g, 100 mmol)を少しずつ添加した。この混合物を室温でさらに2時間この温度で撹拌した。混合物を冷やした後、500mLの水を添加して全ての生成物を沈殿させた。固体を濾過し、熱水で洗った。粗生成物をCH2Cl2から一度再結晶し、次にEtOAc/ヘキサンから再結晶して、24gの純粋な3-ヨードカルバゾールを得た。
トシルクロライド(8.4 g, 44 mmol)を、200mLのアセトン中の3-ヨードカルバゾール(11.7 g, 40 mmol)と粉砕したKOH(2.7 g, 48 mmol)の溶液に添加した。この混合物を3時間還流させ、次に冷やした。それを、撹拌下、1Lの冷水中に注いだ。30分の撹拌後、液体をデカンテーションした。こうして粗生成物を、ビーカー壁上に粘着性の固体として得た。約11gの純粋な3-ヨード-9-トシルカルバゾールをCH2Cl2/EtOHからの再結晶後に得た。
3-ヨード-9-トシルカルバゾール(10.6 g, 24 mmol)、カルバゾール(4.8 g, 29 mmol)、CuI(0.4 g, 2.0 mmol)、トランス-1,2-ジアミノシクロヘキサン(0.3 g, 2.4 mmol)、三塩基性リン酸カリウム(10.6 g, 50 mmol)、及び150mLのトルエンを、500mLの丸底フラスコに入れた。反応物を加熱還流させ、且つ窒素雰囲気下で24時間撹拌した。冷却後、混合物をシリカゲルカラムで精製した。3-(9-カルバゾリル)-9-トシルカルバゾールの収量は10gだった。
3-(9-カルバゾリル)-9-トシルカルバゾール(10.0 g, 21 mmol)、NaOH(8.0g, 200 mmol)、80mLのTHF、40mLのMeOH、及び40mLの水を、500mLの丸底フラスコに入れた。反応物を12時間加熱還流させた。冷却後、混合物をシリカゲルカラムで精製した。3-(9-カルバゾリル)-カルバゾールの収量は8gだった。
3-(9-カルバゾリル)-カルバゾール(3.0 g, 9 mmol)、2-ブロモピリジン(1.9 g, 12 mmol)、CuI(0.2 g, 1.0 mmol)、トランス-1,2-ジアミノシクロヘキサン(0.2 g, 1.5 mmol)、三塩基性リン酸カリウム(5.3 g, 25 mmol)、及び150mLのトルエンを、500mL丸底フラスコに入れた。反応物を加熱還流させ、窒素雰囲気下で24時間撹拌した。冷却後、混合物をシリカゲルカラムで精製した。収量は2.2gだった。この生成物を真空昇華によってさらに精製した。1H NMRの結果によって、所望の化合物であることを確かめた。EOX=0.86V(擬可逆)、Ered=−2.91V(可逆)(vs. Fc+/Fc, 0.10M Bun 4NPF6溶液(DMF)、Pt作用電極及び補助電極、非水Ag/Ag+参照電極、並びに50〜5000 mVs-1で変動させたスキャン速度)。
3-(9-カルバゾリル)カルバゾール(9.8 g, 30 mmol)、3-ヨード-9-トシルカルバゾール(16.1 g, 36 mmol)、CuI(1.7 g, 9 mmol)、トランス-1,2-ジアミノシクロヘキサン(2.1 g, 18 mmol)、三塩基性リン酸カリウム(12.7 g, 60 mmol)、及び250mLのトルエンを、500mLの丸底フラスコに入れた。反応物を加熱還流させ、且つ窒素雰囲気下で24時間撹拌した。冷却後、混合物をシリカゲルカラムで精製した。3-(9-(3-(9-カルバゾリル)カルバゾリル)-9-トシルカルバゾールの収量は20gだった。それを上述したようにして脱トシル化して、12gの3-(9-(3-(9-カルバゾリル)カルバゾリル)カルバゾールを得た。
3-(9-(3-(9-カルバゾリル)カルバゾリル)カルバゾール(3.0 g, 6 mmol)、2-ブロモベンゾチオフェン(2.1 g, 7.8 mmol)、CuI(0.4 g, 1.8 mmol)、トランス-1,2-ジアミノシクロヘキサン(0.4 g, 3.6 mmol)、三塩基性リン酸カリウム(3.2 g, 15 mmol)、及び150mLのトルエンを、500mLの丸底フラスコに入れた。反応物を加熱還流させ、且つ窒素雰囲気下で24時間撹拌した。冷却後、混合物をシリカゲルカラムで精製した。収量は2.9gだった。生成物を真空昇華によってさらに精製した。1H NMRの結果によって、所望の化合物であることを確かめた。EOX=0.81V(擬可逆)、Ered=−2.78V(可逆)(vs. Fc+/Fc, 0.10M Bun 4NPF6溶液(DMF)、Pt作用電極及び補助電極、非水Ag/Ag+参照電極、並びに50〜5000 mVs-1で変動させたスキャン速度)。
磁気攪拌機及び還流コンデンサーを備えた300mLの丸底フラスコに、5-クロロ-メトキシフェニルボロン酸(5.00 g, 33 mmol)、2-アミノ-3-ブロモピリジン(5.70 g, 33 mmol)、Pd2(dba)3(604 mg, 2 mol%)、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(542 mg, 4 mol%)、三塩基性リン酸カリウム・一水和物(22.8 mg, 3 eq)、及び100mLのトルエンを仕込んだ。フラスコを窒素で満たし、反応混合物を加熱還流させ、且つ窒素雰囲気下で24時間撹拌した。次に、反応物を室温に冷やし、シリカ栓を通して濾過し、蒸発させた。残留物をシリカゲル上でのカラムクロマトグラフィー(溶離液はヘキサン/酢酸エチル混合物1:1)にかけて、5.0gの3-(5-クロロ-2-メトキシフェニル)ピリジン-2-アミンを黄色固体として得た。その構造はNMR及びMSスペクトルによって確認した。
3-(5-クロロ-2-メトキシフェニル)ピリジン-2-アミン(5.00 g, 21 mmol)を、THF(409 mL)、HBF4(50%水溶液、36 mL)、及び15mLの水の混合物中に溶かした。この溶液を−5℃に冷やし、亜硝酸ナトリウム(1.70 g、20 mLの水中)を滴下して添加した。反応を−5℃で1時間保ち、次に室温まで温め、室温で夜通し撹拌した。この反応混合物のpHを10に調節し、酢酸エチル(4x25 mL)で抽出した。有機画分を一緒にし、硫酸ナトリウム上で乾燥させ、蒸発させた。残留物をシリカゲル上のカラムクロマトグラフィー(溶離液はヘキサン/酢酸エチル9:1混合物)にかけた。クロマトグラフィーの生成物は3-(5-クロロ-2-メトキシフェニル)-2-フルオロピリジンを含んでおり、純粋な6-クロロベンゾフロ[2,3-b]ピリジン(1.52 g、無色の長い針状晶)を、ヘキサン/酢酸エチルからの再結晶によって得た。
磁気攪拌機及び還流コンデンサーを備えた300mLの丸底フラスコに、6-クロロベンゾフロ[2,3-b]ピリジン(2.04 g, 10 mmol)、3-(9-カルバゾリル)カルバゾール(3.32 g, 10 mmol)、Pd(OAc)2(450 mg, 20 mol%)、P(t-Bu)3(10 mL, トルエン中の1M溶液, 10 mmol)、カリウムtert-ブトキシド(1.92 g, 20 mmol)、及び150 mLのキシレンを仕込んだ。フラスコを窒素で満たし、反応混合物を加熱還流させ、且つ窒素雰囲気下で36時間撹拌した。次に、反応物を室温に冷やし、水で洗い、シリカ栓を通して濾過し、蒸発させた。残留物をシリカゲル上でのカラムクロマトグラフィー(溶離液はヘキサン/酢酸エチル混合物4:1)にかけて、3.01gの6-(9H-3,9’-ビカルバゾール-9-イル)ベンゾフロ[2,3-b]ピリジンを白色固体として得て、その構造はNMR及びMSスペクトルによって確認した。
磁気攪拌機及び還流コンデンサーを備えた500mLの丸底フラスコに、5-クロロ-2-メトキシフェニルボロン酸(9.78 g, 52 mmol)、3-アミノ-2-クロロピリジン(7.00 g, 55 mmol)、2-ジシクロへキシルホスフィノ-2’,6’-ジメトキシビフェニル(S-Phos, 0.43 g, 2 mol%)、酢酸パラジウム(II)(112 mg, 1 mol%)、炭酸カリウム(21.7 g, 157 mmol)、180mLのアセトニトリル、及び20mLの水を仕込んだ。フラスコを窒素で満たし、窒素雰囲気下で24時間加熱還流させた。次に、反応物を室温に冷やし、500mLの水で希釈し、酢酸エチル(5x40 mL)で抽出した。有機画分を一緒にし、硫酸ナトリウム上で乾燥させ、濾過し、蒸発させた。残留物をシリカゲル上でのカラムクロマトグラフィー(溶離液はヘキサン/酢酸エチルの濃度勾配混合物)にかけて、2-(5-クロロ-2-メトキシフェニル)ピリジン-3-アミンを白色結晶として得た(9.5 g、その構造はNMRによって確認した)。
磁気攪拌機及び還流コンデンサーを備えた500mLの丸底フラスコに、2-(5-クロロ-2-メトキシフェニル)ピリジン-3-アミン(9.00 g, 39 mmol)、70mLのTHF、70mLのHBF4(水中50%)、及び40mLの水を仕込んだ。反応混合物を−10℃に冷やし、亜硝酸ナトリウム(5.6g)の溶液(20 mLの水中)を滴下により添加した。反応混合物を徐々に室温まで温め、夜通し撹拌した。反応混合物を500mLの水で希釈し、酢酸エチル(4x50 mL)で抽出した。有機画分を一緒にし、硫酸ナトリウム上で乾燥させ、蒸発させ、残留物をシリカゲル上でのカラムクロマトグラフィー(溶離液はヘキサン/酢酸エチル 9/1混合物)にかけて、8-クロロベンゾフロ[3,2-b]ピリジン(6.00 g, ヘキサン/酢酸エチルからの無色の針状晶)を得た。
磁気攪拌機及び還流コンデンサーを備えた100mLの丸底フラスコに、8-クロロベンゾフロ[3,2-b]ピリジン(2.04 g, 10 mmol)、3-(9-カルバゾリル)カルバゾール(3.32 g, 10 mmol)、Pd(OAc)2(450 mg, 20 mol%)、P(t-Bu)3(10 mL, トルエン中の1M溶液, 10 mmol)、カリウムtert-ブトキシド(1.92 g, 1.5当量)、及び150 mLのキシレンを仕込んだ。フラスコを窒素で満たし、反応混合物を加熱還流させ、且つ窒素雰囲気下で24時間撹拌した。次に、反応物を室温に冷やし、シリカ栓を通して濾過し、蒸発させた。残留物をシリカゲル上でのカラムクロマトグラフィー(溶離液はヘキサン/酢酸エチル混合物9:1)にかけて、2.5gの8-(9H-3,9’-ビカルバゾール-9-イル)ベンゾフロ[2,3-b]ピリジンを白色固体として得た。その構造はNMR及びMSスペクトルによって確認した。
磁気攪拌機及び還流コンデンサーを備えた500mLの丸底フラスコに、2-(メチルチオ)フェニルボロン酸(9.48 g, 56 mmol)、3-アミノ-2-ブロモピリジン(7.15 g, 57 mmol)、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(S-Phos, 0.92 g, 4 mol%)、Pd2(dba)3(1.02 g, 2 mol%)、リン酸カリウム水和物(39 g, 3当量)、及び100mLのトルエンを仕込んだ。フラスコを窒素で満たし、窒素雰囲気下で24時間加熱還流させた。次に、反応物を室温に冷やし、500mLの水で希釈し、酢酸エチルで抽出した(5x40 mL)。有機画分を一緒にし、硫酸ナトリウム上で乾燥させ、濾過し、蒸発させた。残留物をシリカゲル上でヘキサン/酢酸エチル傾斜混合物を用いてカラムクロマトグラフィーにかけて、2-(2-(メチルチオ)フェニル)ピリジン-3-アミンを黄色結晶として得た(9.5 g)。その構造はNMRによって確認した。
磁気攪拌機及び還流コンデンサーを備えた500mLの丸底フラスコに、2-(2-(メチルチオ)フェニル)ピリジン-3-アミン(8.42 g, 39 mmol)、70mLのTHF、70mLのHBF4(水中50%)、及び40mLの水を仕込んだ。反応混合物を−10℃に冷やし、亜硝酸ナトリウム(5.6 g)の溶液(20 mLの水中)を滴下により添加した。反応混合物を室温まで徐々に温め、夜通し撹拌した。この反応混合物を500mLの水で希釈し、酢酸エチル(4x50 mL)で抽出した。有機画分を一緒にし、硫酸ナトリウム上で乾燥させ、蒸発させ、残留物をシリカゲル上で、ヘキサン/酢酸エチルの9/1混合物を用いてカラムクロマトグラフィーにかけて、アザ-ジベンゾチオフェン(3.5 g、ヘキサン/酢酸エチルから無色針状晶)を得た。
アザ-ジベンゾチオフェン(1.78 g, 6.7 mmol)を75mLの無水THFに溶かし、その溶液をCO2/アセトン浴で冷やした。n-ブチルリチウム(ヘキサン中の1.6 M溶液、7 mL)を滴下により添加し、その反応混合物の色が橙色に変化し、50mLの無水THF中の2.6gのヨウ素の溶液を直ちに添加した。反応混合物を室温まで温め、NaHSO3の水溶液で処理し、酢酸エチル(4x40 mL)で抽出した。有機画分を一緒にし、硫酸ナトリウム上で乾燥させ、濾過し、蒸発させた。残留物をシリカゲル上のカラムクロマトグラフィー(溶離液としてヘキサン/酢酸エチルの9/1混合物)にかけた。精製した物質を次に同じ溶媒から再結晶して、目的とするヨード誘導体1.55gを得て、構造はNMR及びGC/MSによって確かめた。
磁気攪拌機及び還流コンデンサーを備えた100mLの丸底フラスコに、ヨード誘導体(1.55 g, 5 mmol)、3-(9-カルバゾリル)カルバゾール(1.66 g, 5 mmol)、Pd(OAc)2(225 mg, 20 mol%)、P(t-Bu)3(トルエン中の1M溶液5 mL, 5 mmol)、カリウムtert-ブトキシド(0.96 g, 1.5当量)、及び75 mLのキシレンを仕込んだ。フラスコを窒素で満たし、反応混合物を加熱還流させ、且つ窒素雰囲気下で24時間撹拌した。次に、反応物を室温に冷やし、シリカ栓を通して濾過し、蒸発させた。残留物をシリカゲル上でのカラムクロマトグラフィー(溶離液はヘキサン/酢酸エチル混合物9:1)にかけて、2.0gのカップリング生成物を白色固体として得た。その構造はNMR及びMSスペクトルによって確認した。
上記の白色生成物を100mLのTHFに溶かし、ドライアイス/アセトン浴で冷やし、ヘキサン中のn-BuLi溶液(1当量)を一度に添加した。1時間後、5mLの水を一度に添加し、反応混合物を室温まで温め、水で希釈し、酢酸エチルで抽出した。蒸発と、それに続くシリカゲル上でのカラムクロマトグラフィー(溶離液としてヘキサン/酢酸エチル 9/1混合物)により、1.5gの目的化合物を白色固体として得た。構造はNMR及びMSデータによって確かめた。
Claims (37)
- 以下の化合物を含んでなるカルバゾール含有化合物。
aは1〜20であり;
bは0〜20であり;
mは0〜2であり;
nは0〜2であり;
m+nは少なくとも1であり;
Xは、ビフェニル、ターフェニル、ナフタレン、トリフェニレン、フェナントレン、フルオレン、クリセン、ジベンゾチオフェン、ジベンゾフラン、ベンゾフラン、ベンゾチオフェン、ピラゾール、イミダゾール、トリアゾール、オキサゾール、チアゾール、オキサジアゾール、オキサトリアゾール、ジオキサゾール、チアジアゾール、ピリジン、ピリダジン、ピリミジン、ピラジン、トリアジン、インドール、ベンゾイミダゾール、インダゾール、ベンゾオキサゾール、ベンゾイソオキサゾール、ベンゾチアゾール、キノリン、イソキノリン、シンノリン、キナゾリン、キノキサリン、ナフチリジン、フタラジン、プテリジン、キサンテン、フェノチアジン、フェノキサジン、ベンゾフロピリジン、フロジピリジン、ベンゾチエノピリジン、及びチエノジピリジンからなる群から選択され;
XはRで置換されており、Rは、水素、アルキル、ヘテロアルキル、ベンゼン、ビフェニル、ターフェニル、ナフタレン、フェナレン、フェナントレン、フルオレン、クリセン、ジベンゾチオフェン、ジベンゾフラン、ベンゾフラン、ベンゾチオフェン、ピラゾール、イミダゾール、トリアゾール、オキサゾール、チアゾール、オキサジアゾール、オキサトリアゾール、ジオキサゾール、チアジアゾール、ピリジン、ピリダジン、ピリミジン、ピラジン、トリアジン、インドール、ベンゾイミダゾール、インダゾール、ベンゾオキサゾール、ベンゾイソオキサゾール、ベンゾチアゾール、キノリン、イソキノリン、シンノリン、キナゾリン、キノキサリン、ナフチリジン、フタラジン、プテリジン、キサンテン、フェノチアジン、フェノキサジン、ベンゾフロピリジン、フロジピリジン、ベンゾチエノピリジン、及びチエノジピリジンからなる群から選択される。 - aが1〜20であり、且つnが0である、請求項1に記載の化合物。
- aが1又は2であり、且つnが0である、請求項1に記載の化合物。
- aが1であり、bが1であり、且つnが1である、請求項1に記載の化合物。
- Xが、ビフェニル、ターフェニル、トリフェニレン、フェナントレン、フルオレン、ジベンゾチオフェン、ジベンゾフラン、ピリジン、ピリダジン、ピリミジン、ピラジン、トリアジン、ベンゾイミダゾール、ベンゾチアゾール、キノリン、イソキノリン、ベンゾフロピリジン、フロジピリジン、ベンゾチエノピリジン、及びチエノジピリジンから選択される、請求項1に記載の化合物。
- Xが、ジベンゾチオフェン、ジベンゾフラン、ベンゾフロピリジン、フロジピリジン、ベンゾチエノピリジン、チエノジピリジン、及びトリフェニレンからなる群から選択される、請求項1に記載の化合物。
- Rが、水素、アルキル、ベンゼン、ビフェニル、ターフェニル、トリフェニレン、フェナントレン、フルオレン、ジベンゾチオフェン、ジベンゾフラン、ピリジン、ピリダジン、ピリミジン、ピラジン、トリアジン、ベンゾイミダゾール、ベンゾチアゾール、キノリン、イソキノリン、ベンゾフロピリジン、フロジピリジン、ベンゾチエノピリジン、及びチエノジピリジンからなる群から選択される、請求項1に記載の化合物。
- Rが、水素、アルキル、ベンゼン、ビフェニル、ターフェニル、ジベンゾチオフェン、及びジベンゾフランからなる群から選択される、請求項1に記載の化合物。
- Rが、水素、アルキル、ベンゼン、ビフェニル、ターフェニル、トリフェニレン、フェナントレン、フルオレン、ジベンゾチオフェン、ジベンゾフラン、ピリジン、ピリダジン、ピリミジン、ピラジン、トリアジン、ベンゾイミダゾール、ベンゾチアゾール、キノリン、イソキノリン、ベンゾフロピリジン、フロジピリジン、ベンゾチエノピリジン、及びチエノジピリジンからなる群から選択される、請求項5に記載の化合物。
- Rが、水素、アルキル、ベンゼン、ビフェニル、ターフェニル、ジベンゾチオフェン、及びジベンゾフランからなる群から選択される、請求項6に記載の化合物。
- アノード;
カソード;及び、
前記アノードと前記カソードとの間に配置された第一の有機層、を含む有機発光デバイスであって、
前記有機層が以下のものを含んでなるカルバゾール含有化合物を含む、有機発光デバイス。
aは1〜20であり;
bは0〜20であり;
mは0〜2であり;
nは0〜2であり;
m+nは少なくとも1であり;
Xは、ビフェニル、ターフェニル、ナフタレン、トリフェニレン、フェナントレン、フルオレン、クリセン、ジベンゾチオフェン、ジベンゾフラン、ベンゾフラン、ベンゾチオフェン、ピラゾール、イミダゾール、トリアゾール、オキサゾール、チアゾール、オキサジアゾール、オキサトリアゾール、ジオキサゾール、チアジアゾール、ピリジン、ピリダジン、ピリミジン、ピラジン、トリアジン、インドール、ベンゾイミダゾール、インダゾール、ベンゾオキサゾール、ベンゾイソオキサゾール、ベンゾチアゾール、キノリン、イソキノリン、シンノリン、キナゾリン、キノキサリン、ナフチリジン、フタラジン、プテリジン、キサンテン、フェノチアジン、フェノキサジン、ベンゾフロピリジン、フロジピリジン、ベンゾチエノピリジン、及びチエノジピリジンからなる群から選択され;
XはRで置換されており、Rは、水素、アルキル、ヘテロアルキル、ベンゼン、ビフェニル、ターフェニル、ナフタレン、フェナレン、フェナントレン、フルオレン、クリセン、ジベンゾチオフェン、ジベンゾフラン、ベンゾフラン、ベンゾチオフェン、ピラゾール、イミダゾール、トリアゾール、オキサゾール、チアゾール、オキサジアゾール、オキサトリアゾール、ジオキサゾール、チアジアゾール、ピリジン、ピリダジン、ピリミジン、ピラジン、トリアジン、インドール、ベンゾイミダゾール、インダゾール、ベンゾオキサゾール、ベンゾイソオキサゾール、ベンゾチアゾール、キノリン、イソキノリン、シンノリン、キナゾリン、キノキサリン、ナフチリジン、フタラジン、プテリジン、キサンテン、フェノチアジン、フェノキサジン、ベンゾフロピリジン、フロジピリジン、ベンゾチエノピリジン、及びチエノジピリジンからなる群から選択される。 - 前記第一の有機層が発光層であり、且つ前記カルバゾール含有化合物が前記第一の有機層中のホストである、請求項19に記載のデバイス。
- 前記発光層がリン光発光体をさらに含む、請求項20に記載のデバイス。
- 前記リン光発光体が、下記式を有するモノアニオン性の二座配位子を含むリン光性金属錯体を含む化合物である、請求項21に記載のデバイス。
R1a〜iはそれぞれ独立に、H、ヒドロカルビル、ヘテロ原子置換ヒドロカルビル、シアノ、フルオロ、OR2a、SR2a、NR2aR2b、BR2aR2b、又はSiR2aR2bR2cであり、R2a〜cはそれぞれ独立に、ヒドロカルビル又はヘテロ原子置換ヒドロカルビルであり、R1a〜i及びR2a〜cの任意の2つが連結して飽和もしくは不飽和の、芳香族もしくは非芳香族の環を形成してもよく;但し、R1a〜iはNに結合している場合はH以外であり;
前記金属は、40より大きな原子番号をもつ非放射性金属からなる群から選択され;
前記二座配位子は別の配位子と連結して三座、四座、五座、又は六座配位子を構成してもよい。 - 非発光層である第二の有機層をさらに含む、請求項20に記載のデバイス。
- 前記第一の有機層が前記第二の有機層に隣接している、請求項24に記載のデバイス。
- 前記リン光発光体が425nm〜495nmの三重項エネルギーを有し、Xが、ジベンゾチオフェン、ジベンゾフラン、ベンゾフロピリジン、フロジピリジン、ベンゾチエノピリジン、チエノジピリジン、及びトリフェニレンから選択され、且つ、Rが、水素、アルキル、ベンゼン、ビフェニル、ターフェニル、ジベンゾチオフェン、及びジベンゾフランから選択される、請求項21に記載のデバイス。
- 前記三重項エネルギーが440nm〜480nmである、請求項26に記載のデバイス。
- 前記リン光発光体が、495nm〜570nmの三重項エネルギーを有し、Xが、ビフェニル、ターフェニル、トリフェニレン、フェナントレン、フルオレン、ジベンゾチオフェン、ジベンゾフラン、ピリジン、ピリダジン、ピリミジン、ピラジン、トリアジン、ベンゾイミダゾール、ベンゾチアゾール、キノリン、イソキノリン、ベンゾフロピリジン、フロジピリジン、ベンゾチエノピリジン、及びチエノジピリジンから選択され、且つ、Rが、水素、アルキル、ベンゼン、ビフェニル、ターフェニル、トリフェニレン、フェナントレン、フルオレン、ジベンゾチオフェン、ジベンゾフラン、ピリジン、ピリダジン、ピリミジン、ピラジン、トリアジン、ベンゾイミダゾール、ベンゾチアゾール、キノリン、イソキノリン、ベンゾフロピリジン、フロジピリジン、ベンゾチエノピリジン、及びチエノジピリジンから選択される、請求項21に記載のデバイス。
- 前記三重項エネルギーが510nm〜530nmである、請求項28に記載のデバイス。
- 前記オリゴカルバゾール含有化合物が10〜100質量%の濃度を有する、請求項18に記載のデバイス。
- 前記オリゴカルバゾール含有化合物が40〜99.9質量%の濃度を有する、請求項30に記載のデバイス。
- 0.1〜30質量%の濃度を有するリン光発光体をさらに含む、請求項31に記載のデバイス。
- デバイスを含む消費者製品であって、前記デバイスがさらに、
アノード;
カソード;及び、
前記アノードと前記カソードとの間に配置された有機層、を含み、
前記有機層が以下のものを含んでなるカルバゾール含有化合物をさらに含む、消費者製品。
aは1〜20であり;
bは0〜20であり;
mは0〜2であり;
nは0〜2であり;
m+nは少なくとも1であり;
Xは、ビフェニル、ターフェニル、ナフタレン、トリフェニレン、フェナントレン、フルオレン、クリセン、ジベンゾチオフェン、ジベンゾフラン、ベンゾフラン、ベンゾチオフェン、ピラゾール、イミダゾール、トリアゾール、オキサゾール、チアゾール、オキサジアゾール、オキサトリアゾール、ジオキサゾール、チアジアゾール、ピリジン、ピリダジン、ピリミジン、ピラジン、トリアジン、インドール、ベンゾイミダゾール、インダゾール、ベンゾオキサゾール、ベンゾイソオキサゾール、ベンゾチアゾール、キノリン、イソキノリン、シンノリン、キナゾリン、キノキサリン、ナフチリジン、フタラジン、プテリジン、キサンテン、フェノチアジン、フェノキサジン、ベンゾフロピリジン、フロジピリジン、ベンゾチエノピリジン、及びチエノジピリジンからなる群から選択され;
XはRで置換されており、Rは、水素、アルキル、ヘテロアルキル、ベンゼン、ビフェニル、ターフェニル、ナフタレン、フェナレン、フェナントレン、フルオレン、クリセン、ジベンゾチオフェン、ジベンゾフラン、ベンゾフラン、ベンゾチオフェン、ピラゾール、イミダゾール、トリアゾール、オキサゾール、チアゾール、オキサジアゾール、オキサトリアゾール、ジオキサゾール、チアジアゾール、ピリジン、ピリダジン、ピリミジン、ピラジン、トリアジン、インドール、ベンゾイミダゾール、インダゾール、ベンゾオキサゾール、ベンゾイソオキサゾール、ベンゾチアゾール、キノリン、イソキノリン、シンノリン、キナゾリン、キノキサリン、ナフチリジン、フタラジン、プテリジン、キサンテン、フェノチアジン、フェノキサジン、ベンゾフロピリジン、フロジピリジン、ベンゾチエノピリジン、及びチエノジピリジンからなる群から選択される。 - 第一の電極を準備する工程;
ホストとリン光発光体とを共堆積させて発光層を形成させる工程であって、前記発光層が下記式Iを含む、カルバゾール含有化合物を含む工程;及び
第二の電極を堆積させる工程、を含む、有機発光デバイスの製造方法:
aは1〜20であり;
bは0〜20であり;
mは0〜2であり;
nは0〜2であり;
m+nは少なくとも1であり;
Xは、ビフェニル、ターフェニル、ナフタレン、トリフェニレン、フェナントレン、フルオレン、クリセン、ジベンゾチオフェン、ジベンゾフラン、ベンゾフラン、ベンゾチオフェン、ピラゾール、イミダゾール、トリアゾール、オキサゾール、チアゾール、オキサジアゾール、オキサトリアゾール、ジオキサゾール、チアジアゾール、ピリジン、ピリダジン、ピリミジン、ピラジン、トリアジン、インドール、ベンゾイミダゾール、インダゾール、ベンゾオキサゾール、ベンゾイソオキサゾール、ベンゾチアゾール、キノリン、イソキノリン、シンノリン、キナゾリン、キノキサリン、ナフチリジン、フタラジン、プテリジン、キサンテン、フェノチアジン、フェノキサジン、ベンゾフロピリジン、フロジピリジン、ベンゾチエノピリジン、及びチエノジピリジンからなる群から選択され;
XはRで置換されており、Rは、水素、アルキル、ヘテロアルキル、ベンゼン、ビフェニル、ターフェニル、ナフタレン、フェナレン、フェナントレン、フルオレン、クリセン、ジベンゾチオフェン、ジベンゾフラン、ベンゾフラン、ベンゾチオフェン、ピラゾール、イミダゾール、トリアゾール、オキサゾール、チアゾール、オキサジアゾール、オキサトリアゾール、ジオキサゾール、チアジアゾール、ピリジン、ピリダジン、ピリミジン、ピラジン、トリアジン、インドール、ベンゾイミダゾール、インダゾール、ベンゾオキサゾール、ベンゾイソオキサゾール、ベンゾチアゾール、キノリン、イソキノリン、シンノリン、キナゾリン、キノキサリン、ナフチリジン、フタラジン、プテリジン、キサンテン、フェノチアジン、フェノキサジン、ベンゾフロピリジン、フロジピリジン、ベンゾチエノピリジン、及びチエノジピリジンからなる群から選択される。 - 前記第一の電極がアノードであり、前記第二の電極がカソードである、請求項32に記載の製造方法。
- 前記第一の電極の後で且つ前記発光層の前に有機層を堆積させる、請求項32に記載の製造方法。
- 前記有機層が正孔輸送層である、請求項34に記載の製造方法。
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CN101939296B (zh) | 2014-08-13 |
JP2014196342A (ja) | 2014-10-16 |
WO2009086028A3 (en) | 2009-08-27 |
JP5575661B2 (ja) | 2014-08-20 |
EP2240446A2 (en) | 2010-10-20 |
JP5944440B2 (ja) | 2016-07-05 |
KR20150087423A (ko) | 2015-07-29 |
TW200940504A (en) | 2009-10-01 |
CN101939296A (zh) | 2011-01-05 |
EP2240446B2 (en) | 2018-09-19 |
US20090134784A1 (en) | 2009-05-28 |
KR20100099327A (ko) | 2010-09-10 |
TWI468392B (zh) | 2015-01-11 |
KR101684205B1 (ko) | 2016-12-07 |
WO2009086028A2 (en) | 2009-07-09 |
EP2240446B1 (en) | 2015-11-11 |
US8221905B2 (en) | 2012-07-17 |
KR101645737B1 (ko) | 2016-08-04 |
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