Modular Synthesis of Aromatic Hydrocarbon Macrocycles for Simplified, Single-Layer Organic Light-Emitting Devices

Koki Ikemoto; Asami Yoshii; Tomoo Izumi; Hideo Taka; Hiroshi Kita; Jing Yang Xue; Ryo Kobayashi; Sota Sato; Hiroyuki Isobe

doi:10.1021/acs.joc.5b02620

Modular Synthesis of Aromatic Hydrocarbon Macrocycles for Simplified, Single-Layer Organic Light-Emitting Devices

Koki Ikemoto, Asami Yoshii, Tomoo Izumi, Hideo Taka, Hiroshi Kita, Jing Yang Xue, Ryo Kobayashi, Sota Sato, Hiroyuki Isobe

Research output: Contribution to journal › Article › peer-review

27 Citations (Scopus)

Abstract

A method for the modular synthesis of aromatic hydrocarbon macrocycles has been developed for base materials in single-layer organic light-emitting devices. The method with Ir-catalyzed direct C-H borylation and Suzuki-Miyaura coupling was concise and scalable, which allowed for a gram-scale preparation of aromatic hydrocarbon macrocycles that have bulky substituents at the periphery. The new arylated hydrocarbon macrocycles enabled a quantitative electro-optical conversion in organic light-emitting devices with a phosphorescent emitter, which is, notably, in a single-layer architecture consisting of two regions of doped and undoped materials. The highest external quantum efficiencies reached 24.8%, surpassing those of previous hydrocarbon base materials.

Original language	English
Pages (from-to)	662-666
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	81
Issue number	2
DOIs	https://doi.org/10.1021/acs.joc.5b02620
Publication status	Published - 2016 Jan 15

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/acs.joc.5b02620

Fingerprint Dive into the research topics of 'Modular Synthesis of Aromatic Hydrocarbon Macrocycles for Simplified, Single-Layer Organic Light-Emitting Devices'. Together they form a unique fingerprint.

Cite this

Modular Synthesis of Aromatic Hydrocarbon Macrocycles for Simplified, Single-Layer Organic Light-Emitting Devices. / Ikemoto, Koki; Yoshii, Asami; Izumi, Tomoo; Taka, Hideo; Kita, Hiroshi; Xue, Jing Yang; Kobayashi, Ryo; Sato, Sota; Isobe, Hiroyuki.

In: Journal of Organic Chemistry, Vol. 81, No. 2, 15.01.2016, p. 662-666.

Research output: Contribution to journal › Article › peer-review

@article{d73da0af0af84e4db6c278a331049756,

title = "Modular Synthesis of Aromatic Hydrocarbon Macrocycles for Simplified, Single-Layer Organic Light-Emitting Devices",

abstract = "A method for the modular synthesis of aromatic hydrocarbon macrocycles has been developed for base materials in single-layer organic light-emitting devices. The method with Ir-catalyzed direct C-H borylation and Suzuki-Miyaura coupling was concise and scalable, which allowed for a gram-scale preparation of aromatic hydrocarbon macrocycles that have bulky substituents at the periphery. The new arylated hydrocarbon macrocycles enabled a quantitative electro-optical conversion in organic light-emitting devices with a phosphorescent emitter, which is, notably, in a single-layer architecture consisting of two regions of doped and undoped materials. The highest external quantum efficiencies reached 24.8%, surpassing those of previous hydrocarbon base materials.",

author = "Koki Ikemoto and Asami Yoshii and Tomoo Izumi and Hideo Taka and Hiroshi Kita and Xue, {Jing Yang} and Ryo Kobayashi and Sota Sato and Hiroyuki Isobe",

year = "2016",

month = jan,

day = "15",

doi = "10.1021/acs.joc.5b02620",

language = "English",

volume = "81",

pages = "662--666",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "2",

}

TY - JOUR

T1 - Modular Synthesis of Aromatic Hydrocarbon Macrocycles for Simplified, Single-Layer Organic Light-Emitting Devices

AU - Ikemoto, Koki

AU - Yoshii, Asami

AU - Izumi, Tomoo

AU - Taka, Hideo

AU - Kita, Hiroshi

AU - Xue, Jing Yang

AU - Kobayashi, Ryo

AU - Sato, Sota

AU - Isobe, Hiroyuki

PY - 2016/1/15

Y1 - 2016/1/15

N2 - A method for the modular synthesis of aromatic hydrocarbon macrocycles has been developed for base materials in single-layer organic light-emitting devices. The method with Ir-catalyzed direct C-H borylation and Suzuki-Miyaura coupling was concise and scalable, which allowed for a gram-scale preparation of aromatic hydrocarbon macrocycles that have bulky substituents at the periphery. The new arylated hydrocarbon macrocycles enabled a quantitative electro-optical conversion in organic light-emitting devices with a phosphorescent emitter, which is, notably, in a single-layer architecture consisting of two regions of doped and undoped materials. The highest external quantum efficiencies reached 24.8%, surpassing those of previous hydrocarbon base materials.

AB - A method for the modular synthesis of aromatic hydrocarbon macrocycles has been developed for base materials in single-layer organic light-emitting devices. The method with Ir-catalyzed direct C-H borylation and Suzuki-Miyaura coupling was concise and scalable, which allowed for a gram-scale preparation of aromatic hydrocarbon macrocycles that have bulky substituents at the periphery. The new arylated hydrocarbon macrocycles enabled a quantitative electro-optical conversion in organic light-emitting devices with a phosphorescent emitter, which is, notably, in a single-layer architecture consisting of two regions of doped and undoped materials. The highest external quantum efficiencies reached 24.8%, surpassing those of previous hydrocarbon base materials.

UR - http://www.scopus.com/inward/record.url?scp=84954416391&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84954416391&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.5b02620

DO - 10.1021/acs.joc.5b02620

M3 - Article

AN - SCOPUS:84954416391

VL - 81

SP - 662

EP - 666

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 2

ER -

Modular Synthesis of Aromatic Hydrocarbon Macrocycles for Simplified, Single-Layer Organic Light-Emitting Devices

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Cite this