Rita Butkute, Ausrine Masiulyte, Ehsan Ullah Rashid, Svetlana Sargsyan, Neelalohith Satish Moudgalya, Karolis Leitonas, Dmytro Volyniuk and Juozas V. Grazulevicius*,
{"title":"具有高热稳定性的 2,7- 二叔丁基-9,9-二甲基-9,10-二氢吖啶和菲罗咪唑衍生物赋予有机光电探测器和有机发光二极管超低暗电流密度,显示平衡的双极电荷传输","authors":"Rita Butkute, Ausrine Masiulyte, Ehsan Ullah Rashid, Svetlana Sargsyan, Neelalohith Satish Moudgalya, Karolis Leitonas, Dmytro Volyniuk and Juozas V. Grazulevicius*, ","doi":"10.1021/acsaelm.4c00746","DOIUrl":null,"url":null,"abstract":"<p >Seeking to develop more advanced organic photodetectors (OPDs) and organic light-emitting diodes (OLEDs), we designed three derivatives of 2,7-di-<i>tert</i>-butyl-9,9-dimethyl-9,10-dihydroacridine and phenanthroimidazole with either −CF<sub>3</sub> or −C(CH<sub>3</sub>)<sub>3</sub> groups. These compounds were synthesized by Buchwald–Hartwig amination reaction with yields of up to 77%. They show high glass transition temperatures above 200 °C and balanced electron and hole transport with mobilities of up to 10<sup>–3</sup> cm<sup>2</sup>/V·s under strong electric fields. One compound with −C(CH<sub>3</sub>)<sub>3</sub> groups outperformed the standard host material in the OLED, which showed 17% higher external quantum efficiency. The low dark current density resulted in enhanced efficiency of OLEDs due to minimal charge leakage. Compared to the commercial material 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), this compound allowed achieving superior photosensitivity in OPDs. The photocurrent to dark current density ratio at a reverse voltage of −10 V was found to be 6000. For TAPC-based OPDs, this ratio was only 43.3. The dark current density was significantly reduced to 4.5 × 10<sup>–7</sup> mA·cm<sup>–2</sup>, compared to 3 × 10<sup>–4</sup> mA·cm<sup>–2</sup> for TAPC-based OPDs at the same reverse voltage, thus enhancing the photosensitivity of the OPDs.</p>","PeriodicalId":3,"journal":{"name":"ACS Applied Electronic Materials","volume":null,"pages":null},"PeriodicalIF":4.3000,"publicationDate":"2024-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsaelm.4c00746","citationCount":"0","resultStr":"{\"title\":\"Ultralow Dark Current Density of Organic Photodetectors and Organic Light-Emitting Diodes Endowed by Highly Thermally Stable Derivatives of 2,7-Di-tert-butyl-9,9-dimethyl-9,10-dihydroacridine and Phenanthroimidazole Exhibiting Balanced Bipolar Charge Transport\",\"authors\":\"Rita Butkute, Ausrine Masiulyte, Ehsan Ullah Rashid, Svetlana Sargsyan, Neelalohith Satish Moudgalya, Karolis Leitonas, Dmytro Volyniuk and Juozas V. Grazulevicius*, \",\"doi\":\"10.1021/acsaelm.4c00746\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Seeking to develop more advanced organic photodetectors (OPDs) and organic light-emitting diodes (OLEDs), we designed three derivatives of 2,7-di-<i>tert</i>-butyl-9,9-dimethyl-9,10-dihydroacridine and phenanthroimidazole with either −CF<sub>3</sub> or −C(CH<sub>3</sub>)<sub>3</sub> groups. These compounds were synthesized by Buchwald–Hartwig amination reaction with yields of up to 77%. They show high glass transition temperatures above 200 °C and balanced electron and hole transport with mobilities of up to 10<sup>–3</sup> cm<sup>2</sup>/V·s under strong electric fields. One compound with −C(CH<sub>3</sub>)<sub>3</sub> groups outperformed the standard host material in the OLED, which showed 17% higher external quantum efficiency. The low dark current density resulted in enhanced efficiency of OLEDs due to minimal charge leakage. Compared to the commercial material 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), this compound allowed achieving superior photosensitivity in OPDs. The photocurrent to dark current density ratio at a reverse voltage of −10 V was found to be 6000. For TAPC-based OPDs, this ratio was only 43.3. The dark current density was significantly reduced to 4.5 × 10<sup>–7</sup> mA·cm<sup>–2</sup>, compared to 3 × 10<sup>–4</sup> mA·cm<sup>–2</sup> for TAPC-based OPDs at the same reverse voltage, thus enhancing the photosensitivity of the OPDs.</p>\",\"PeriodicalId\":3,\"journal\":{\"name\":\"ACS Applied Electronic Materials\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.3000,\"publicationDate\":\"2024-06-13\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://pubs.acs.org/doi/epdf/10.1021/acsaelm.4c00746\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ACS Applied Electronic Materials\",\"FirstCategoryId\":\"88\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acsaelm.4c00746\",\"RegionNum\":3,\"RegionCategory\":\"材料科学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"ENGINEERING, ELECTRICAL & ELECTRONIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Applied Electronic Materials","FirstCategoryId":"88","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acsaelm.4c00746","RegionNum":3,"RegionCategory":"材料科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"ENGINEERING, ELECTRICAL & ELECTRONIC","Score":null,"Total":0}
Ultralow Dark Current Density of Organic Photodetectors and Organic Light-Emitting Diodes Endowed by Highly Thermally Stable Derivatives of 2,7-Di-tert-butyl-9,9-dimethyl-9,10-dihydroacridine and Phenanthroimidazole Exhibiting Balanced Bipolar Charge Transport
Seeking to develop more advanced organic photodetectors (OPDs) and organic light-emitting diodes (OLEDs), we designed three derivatives of 2,7-di-tert-butyl-9,9-dimethyl-9,10-dihydroacridine and phenanthroimidazole with either −CF3 or −C(CH3)3 groups. These compounds were synthesized by Buchwald–Hartwig amination reaction with yields of up to 77%. They show high glass transition temperatures above 200 °C and balanced electron and hole transport with mobilities of up to 10–3 cm2/V·s under strong electric fields. One compound with −C(CH3)3 groups outperformed the standard host material in the OLED, which showed 17% higher external quantum efficiency. The low dark current density resulted in enhanced efficiency of OLEDs due to minimal charge leakage. Compared to the commercial material 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), this compound allowed achieving superior photosensitivity in OPDs. The photocurrent to dark current density ratio at a reverse voltage of −10 V was found to be 6000. For TAPC-based OPDs, this ratio was only 43.3. The dark current density was significantly reduced to 4.5 × 10–7 mA·cm–2, compared to 3 × 10–4 mA·cm–2 for TAPC-based OPDs at the same reverse voltage, thus enhancing the photosensitivity of the OPDs.