JP6674542B2 - 供与体と受容体との間に2つの非共役ブリッジを有する光電変換デバイス用の熱活性化遅延蛍光有機分子 - Google Patents
供与体と受容体との間に2つの非共役ブリッジを有する光電変換デバイス用の熱活性化遅延蛍光有機分子 Download PDFInfo
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/36—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atoms of the amino groups bound to hydrogen atoms or to carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/46—Phenazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/38—[b, e]-condensed with two six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
- C07D321/12—Eight-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Description
式Iの受容体A及び供与体Dの説明
#標記位置、供与体部分Dまたは受容体部分Aが前記位置でB1及びB2と結合する。化学基X1〜X7及びY1〜Y4は以下のとおりである。
Y1、Y2、Y3及びY4は、それぞれ独立にCまたはNである。X1〜X7は、それぞれ独立にN、O、S、Se、CH、NH、C―R1またはN―R2である。
EDG実例:
選択されたEDG置換に対し、供与体強度(EDG強度)を確定して排列することもでき、
強電子供与:―O―、―N(CH3)2、―N(C6H5)2、フェノキサジン 基、フェノチアジニル基、カルバゾイル基、―NHCH3、
中程度強度電子供与:―OC6H5、―OCH3、―NH(CO)CH3;
弱電子供与:アリ―ル基、―C(CH3)3、―CH3。
EWG実例:
選択されたEWG置換に対し、受容体強度(EWG強度)に基づく排列してもよく、
強電子吸引:―NO2、―CF3、―CH(CN)2、―CN;
中程度強度電子吸引:―SO3CH3、―COCH3、―CHO;―F
弱電子吸引:―Cl、―Br、―I。 (必要であれば、SBKの増加も適用する)
化学基R8〜R22の定義はR1及びR2と同様である。
具体的な実施手段において、本発明に基づく有機分子は式XVIIIに基づく構造を有する。
式XVIIIには置換化学基が説明される。
実施例分子 1
反応物及び反応条件:
以下の反応式に基づいて合成を行うこともできる。
反応物及び反応条件:
(1) CH3CO2Na:230°C, 3時間
(2) HPO2, I2, 赤リン, CH3COOH:80°C, 24 時間
(3) (H3PO4)n:175°C, 5時間
(4) Al[OCH(CH3)2]3,:275°C, 3時間
(5) (t―C4H9―C6H5)2NH, Pd(CH3COO)2, P[(C(CH3)3]3, (CH3)3CONa:90°C, 19時間
Rf(シクロヘキサン/酢酸エステル 10:1): 0.52. 1H NMR (CDCI3, 300 MHz, Δ ppm): 1.31 (s, 18 H), 3.13 (m, 4H), 4.05 (s, 2H), 6.84 (dd, J=3.6 Hz, J=12.0 Hz, 1H), 6.90 (s, 1H), 6.95 (s, 1H), 6.95 (d, J=9 Hz, 5H), 7.22 (d, J=9 Hz, 4H), 7.55 (s, 2H). 13C―NMR (300 MHz CDCI3, Δ ppm): 30.72 (CH2), 31.46 (CH3), 32.80 (CH2), 34.31(CH2), 40.56 (Cquat), 1 13.16 (Cquat), 1 13.73 (Cquat), 1 15.59 (Cquat), 122.35 (Cquat), 123.48 (CH), 123.78 (CqUat), 126.03 (CH), 130.57 (CqUat), 130.94 (CH), 133.86 (CH), 134.48 (CH), 136.63 (Cquat), 144.91 (CqUat), 145.40 (Cquat), 145.69(Cquat), 146.31 (Cquat).
実施例分子2
反応物及び反応条件:
(1) CH3CO2Na,:230°C, 3 時間
(2) HPO2, I2, 赤リン: CH3COOH, 80°C, 24時間
(3) (H3PO4)n:175°C, 5時間
(4) Al[OCH(CH3)2]3:275°C, 3時間
(5) (t―C4H9―C6H5)2NH, Pd(CH3COO)2, P[(C(CH3)3]3, (CH3)3CONa:90°C, 19時間
実施例分子 3
反応物及び反応条件
(1) CH3CO2Na: 230 °C, 3時間
(2) HPO2, I2, 赤リン, CH3COOH: 80°C, 24時間
(3) (H3PO4)n:175°C, 5 時間
(4) (C2H5)2O, 30°C:24時間 NH4Cl, H2O; F3CCO2H:3 時間, 50°C
(6) K4[Fe(CN)6], Pd(CH3COO)2, P[(C(CH3)3]3, Na2CO3, (CH3)2NCHO:140°C, 12 時間
実施例分子 4
以下、本発明にかかる実施例4の分子について詳細に説明する。図12のフロンティア軌道は、HOMO及びLUMOが分子の顕著に異なっている空間エリア内に位置していることを示す。最低三重項とその上方の 一重項との間の隙間が十分に小さいため、分子は顕著なTADF効果を示すことが予測される。TD―DFT計算(関数B3LYP、ベ―スクラスタ6―31G(d、p))により、実施例4の分子を計算したところ、最適化された三重項幾何構造のエネルギ―準位差は、ΔE(S1―T1)=88cm―1であった。この結果から、実施例4の分子が良好なTADF放射体であることが確認された。
以下の反応説明図は実施例分子4の化学合成を説明する。
反応物及び反応条件
(1) CH3CO2Na:230°C, 3 時間
(2) HPO2, I2, 赤リン, CH3COOH:80°C, 24時間
(3) (H3PO4)n:175°C, 5時間
(4) Al[OCH(CH3)2]3:275°C, 3時間
(5) (t―C4H9―C6H5)2NH, Pd(CH3COO)2, P[(C(CH3)3]3, (CH3)3CONa:90°C, 19時間
実施例分子5
反応物及び反応条件:
(1) CH3CO2Na:230°C, 3 時間
(2) HPO2, I2, 赤リン, CH3COOH: 80°C, 24時間
(3) (H3PO4)n:175°C, 5時間
(4) Al[OCH(CH3)2]3:275°C, 3時間
(5) (t―C4H9―C6H5)2NH, Pd(CH3COO)2, P[(C(CH3)3]3, (CH3)3CONa:90°C, 19時間
実施例分子 6
以下、本発明にかかる実施例6の分子について詳細に説明する。図14のフロンティア軌道は、HOMO及びLUMOが分子の顕著に異なっている空間エリア内に位置していることを示す。最低三重項とその上方の 一重項との間の隙間が十分に小さいため、分子は顕著なTADF効果を示すと予想される。TD―DFT計算(関数B3LYP、ベ―スクラスタ6―31G(d、p))により、実施例6の分子を計算したところ、最適化された三重項幾何構造のエネルギ―準位差は、ΔE(S1―T1)=30cm―1であった。この結果、実施例6の分子が良好なTADF放射体であることが確認された。
実施例分子 7
図15には実施例7の分子のフロンティア軌道HOMO及びLUMOが示される。前記軌道が分子の顕著に異なっている空間エリア内に位置しているため、最低三重項とその上方の 一重項との間の隙間が十分に小さいため、分子は顕著なTADF効果を示すと予想される。TD―DFT計算(関数B3LYP、ベ―スクラスタ6―31G(d、p))により、実施例7の分子を計算したところ、最適化された三重項幾何構造のエネルギ―準位差は、ΔE(S1―T1)=550cm―1であった。この結果、実施例7の分子が良好なTADF放射体であることが確認された。 以下の反応式を参照して、実施例7の分子の化学合成について説明する。
反応物及び反応条件:
(1) CH3CO2Na: 230°C, 3 時間
(2) HI (57 %水溶液), 赤リン:80 °C, 24 時間
(3) (H3PO4)n,:175°C, 5時間
(4) Al[OCH(CH3)2]3: 275°C, 3時間
(5) (CH3)2NH, Pd(CH3COO)2, P[(C(CH3)3]3, (CH3)3CONa:90 °C, 19 時間
実施例分子8
図16のフロンティア軌道はHOMO及びLUMOが分子の顕著に異なっている空間エリア内に位置していることを示す。このため、最低三重項とその上方の 一重項との間の隙間が十分に小さいため、分子は顕著なTADF効果を示すことが予想される。TD―DFT計算(関数B3LYP、ベ―スクラスタ6―31G(d、p))により、実施例8の分子を計算したところ、最適化された三重項幾何構造のエネルギ―準位差は、ΔE(S1―T1)=540cm―1であった。この結果、実施例8の分子は良好なTADF放射体であることが確認された。
反応物及び反応条件:
(1) CH3CO2Na:230°C, 3 時間
(2) HI (57%水溶液), 赤リン:80°C, 24 時間
(3) CH2N2, SO2C12, 80°C, 2 時間; (CH3)3COH, C6H5COOAg, Et3N: 90°C, 2時間.
(4) (H3PO4)n:175°C, 5時間
(5) Al[OCH(CH3)2]3:275°C, 3時間
(6) (CH3)2NH, Pd(CH3COO)2, P[(C(CH3)3]3, (CH3)3CONa:90°C, 19時間
(7) K4[Fe(CN)6], Pd(CH3COO)2, P[(C(CH3)3]3, Na2CO3, (CH3)2NCHO:140°C, 12時間
実施例分子9
図17には実施例9の分子のフロンティア軌道HOMO及びLUMOを示す。前記軌道が分子の顕著に異なっている空間エリア内に位置しているため、最低三重項とその上方の 一重項との間の隙間が十分に小さいため、分子は顕著なTADF効果を示すと予想される。TD―DFT計算(関数B3LYP、ベ―スクラスタ6―31G(d、p))により、実施例9の分子を計算したところ、最適化された三重項幾何構造のエネルギ―準位差は、ΔE(S1―T1)=550cm―1であった。この結果、実施例9の分子が良好なTADF放射体であることが確認された。
実施例分子10
図18には実施例10の分子のフロンティア軌道HOMO及びLUMOを示す。前記軌道が分子の顕著に異なっている空間エリア内に位置しているため、最低三重項とその上方の 一重項との間の隙間が十分に小さいため、分子は顕著なTADF効果を示すと予想される。TD―DFT計算(関数B3LYP、ベ―スクラスタ6―31G(d、p))により、実施例10の分子を計算したところ、最適化された三重項幾何構造のエネルギ―準位差は、ΔE(S1―T1)=140cm―1であった。この結果、実施例10の分子が良好なTADF放射体であることが確認された。
実施例分子 11
図19には実施例11の分子のフロンティア軌道HOMO及びLUMOを示す。前記軌道が分子の顕著に異なっている空間エリア内に位置しているため、最低三重項とその上方の 一重項との間の隙間が十分に小さいため、分子は顕著なTADF効果を表すと予想される。TD―DFT計算(関数B3LYP、ベ―スクラスタ6―31G(d、p))により、実施例11の分子を計算したところ、最適化された三重項幾何構造のエネルギ―準位差は、ΔE(S1―T1)=420cm―1であった。この結果、実施例11の分子が良好なTADF放射体であることが確認された。
実施例分子 12
図20には実施例12の分子のフロンティア軌道HOMO及びLUMOを示す。前記軌道が分子の顕著に異なっている空間エリア内に位置しているため、最低三重項とその上方の 一重項との間の隙間が十分に小さいため、分子は顕著なTADF効果を示すと予想される。TD―DFT計算(関数B3LYP、ベ―スクラスタ6―31G(d、p))により、実施例12の分子を計算したところ、最適化された三重項幾何構造のエネルギ―準位差は、ΔE(S1―T1)=1250cm―1であった。この結果、実施例12の分子が良好なTADF放射体であることが確認された。 図21にはその他の実施例の分子を示す。
Claims (5)
- 式Iで表される構造を含む有機化合物であって、
(A)芳香族環であり、置換基としてジアリールアミノ基(アリール環同士が結合して縮合複素芳香環を形成してもよい)またはジアルキルアミノ基(アルキル基が芳香族環に結合してもよい)を有する供与体Dと、
(B)芳香族環またはヘテロ芳香族環であり、シアノ基またはアルキルスルホニル基を有する受容体Aと、
(C)非共役手段で前記供与体D及び前記受容体Aを連結するブリッジB1及びブリッジB2であり、−CR3R4−、−CR3R4−CR3R4−、−O−CO−、−CR3R4−NR7−から選択される(R3,R4はアルキル、アリール、結合している炭素原子と共に縮合アリール環を形成し、R7はアルキル、2個のR7が結合してアルキレンを形成する)ブリッジB1及びブリッジB2を有する、有機化合物。 - 有機発光ダイオード(OLED)における、光電変換デバイスの放射体層としての、請求項1に記載の有機化合物の使用。
- 請求項1に記載の有機化合物を使用する、光電変換デバイスの製造方法。
- 請求項1に記載の有機化合物を有する光電変換デバイス。
- 前記光電変換デバイスが、有機発光ダイオード(OLED)、発光電気化学電池(LEECまたはLEC)、OLEDセンサ、特に外表に密封されていなかったスクリーンガス及び蒸汽センサ、光学温度センサ、有機太陽電池(OSC)、有機電界効果トランジスタ、有機レーザ器、有機ダイオード、有機光電ダイオード及び「ダウンコンバート」システムからなる群から選ばれる、請求項4に記載の光電変換デバイス。
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DE102015112501.3A DE102015112501B4 (de) | 2015-07-30 | 2015-07-30 | Organische Moleküle mit zwei nicht-konjugierten Brücken zwischen Donator und Akzeptor, Verwendung der Moleküle zur Emission von Licht, sowie opto-elektronische Vorrichtungen und deren Herstellung |
DE102015112501.3 | 2015-07-30 | ||
DE102016106103.4A DE102016106103B4 (de) | 2016-04-04 | 2016-04-04 | Organische Moleküle mit zwei nicht-konjugierten Brücken zwischen Donator und Akzeptor, deren Verwendung zur Emission von Licht, sowie opto-elektronische Vorrichtungen und deren Herstellung |
DE102016106103.4 | 2016-04-04 | ||
PCT/EP2016/068037 WO2017017205A1 (de) | 2015-07-30 | 2016-07-28 | Organische moleküle mit zwei nicht-konjugierten brücken zwischen donator und akzeptor für eine effektive thermisch aktivierte verzögerte fluoreszenz zur anwendung in opto-elektronischen vorrichtungen |
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