Changjun Lee, Sangwook Park, Hyukmin Kwon, Hayoon Lee, Jongwook Park
{"title":"利用含螺芴基团的新型电子传输材料制备高效、长寿命的有机发光二极管","authors":"Changjun Lee, Sangwook Park, Hyukmin Kwon, Hayoon Lee, Jongwook Park","doi":"10.1016/j.dyepig.2025.112849","DOIUrl":null,"url":null,"abstract":"<div><div>In this study, novel electron transport layer (ETL) materials, 2-([1,1′-biphenyl]-2-yl)-4-(dibenzo [<em>b</em>,<em>d</em>]furan-4-yl)-6-(9,9-diphenyl-9H-fluoren-4-yl)-1,3,5-triazine (DFDDT) and 2-(9,9′- spirobi [fluoren]-4-yl)-4-([1,1′-biphenyl]-2-yl)-6-(dibenzo [<em>b</em>,<em>d</em>]furan-4-yl)-1,3,5-triazine (SFDDT), were synthesized and their electrical and optical properties were investigated for application in blue organic light emitting diodes devices. The triazine core, known for its strong electron-withdrawing properties, was utilized as the central framework. To enhance both thermal stability and electron-withdrawing capability, dibenzofuran (DBF) was incorporated, while an o-biphenyl group was introduced to regulate molecular morphology. By incorporating a spirobifluorene structure, SFDDT significantly enhanced thermal stability while preserving the optical properties of DFDDT, achieving a high glass transition temperature (T<sub>g</sub>, 141 °C) and thermal decomposition temperature (T<sub>d</sub>, 436 °C). The electron mobility of n-doped ETL (N-ETL) measurements showed that SFDDT exhibited a value of 6.329 × 10<sup>−5</sup> cm<sup>2</sup>V<sup>−1</sup>s<sup>−1</sup>, approximately 1.9 times higher than that of the commercial ETL material 3,3'-(5'-(3-(pyridin-3-yl)phenyl)-[1,1':3′,1''-terphenyl]-3,3''-diyl)dipyridine (TmPyPB). When applied as an ETL, the device demonstrated a current efficiency (CE) of 5.47 cd/A and an external quantum efficiency (EQE) of 6.73 % at 10 mA/cm<sup>2</sup>, along with a significantly extended lifetime (LT<sub>95</sub>) of 135 h—more than 20 times longer than that of TmPyPB. The molecular design strategy incorporating spirobifluorene in ETL materials not only presents a new approach for ETL material development but also confirms its applicability in long-lifetime applications such as large-screen televisions (TVs), information technology (IT) devices, and automotive display systems.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"240 ","pages":"Article 112849"},"PeriodicalIF":4.1000,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"High efficiency and long device lifetime of organic light-emitting diodes using new electron-transporting materials with spirobifluorene groups\",\"authors\":\"Changjun Lee, Sangwook Park, Hyukmin Kwon, Hayoon Lee, Jongwook Park\",\"doi\":\"10.1016/j.dyepig.2025.112849\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>In this study, novel electron transport layer (ETL) materials, 2-([1,1′-biphenyl]-2-yl)-4-(dibenzo [<em>b</em>,<em>d</em>]furan-4-yl)-6-(9,9-diphenyl-9H-fluoren-4-yl)-1,3,5-triazine (DFDDT) and 2-(9,9′- spirobi [fluoren]-4-yl)-4-([1,1′-biphenyl]-2-yl)-6-(dibenzo [<em>b</em>,<em>d</em>]furan-4-yl)-1,3,5-triazine (SFDDT), were synthesized and their electrical and optical properties were investigated for application in blue organic light emitting diodes devices. The triazine core, known for its strong electron-withdrawing properties, was utilized as the central framework. To enhance both thermal stability and electron-withdrawing capability, dibenzofuran (DBF) was incorporated, while an o-biphenyl group was introduced to regulate molecular morphology. By incorporating a spirobifluorene structure, SFDDT significantly enhanced thermal stability while preserving the optical properties of DFDDT, achieving a high glass transition temperature (T<sub>g</sub>, 141 °C) and thermal decomposition temperature (T<sub>d</sub>, 436 °C). The electron mobility of n-doped ETL (N-ETL) measurements showed that SFDDT exhibited a value of 6.329 × 10<sup>−5</sup> cm<sup>2</sup>V<sup>−1</sup>s<sup>−1</sup>, approximately 1.9 times higher than that of the commercial ETL material 3,3'-(5'-(3-(pyridin-3-yl)phenyl)-[1,1':3′,1''-terphenyl]-3,3''-diyl)dipyridine (TmPyPB). When applied as an ETL, the device demonstrated a current efficiency (CE) of 5.47 cd/A and an external quantum efficiency (EQE) of 6.73 % at 10 mA/cm<sup>2</sup>, along with a significantly extended lifetime (LT<sub>95</sub>) of 135 h—more than 20 times longer than that of TmPyPB. The molecular design strategy incorporating spirobifluorene in ETL materials not only presents a new approach for ETL material development but also confirms its applicability in long-lifetime applications such as large-screen televisions (TVs), information technology (IT) devices, and automotive display systems.</div></div>\",\"PeriodicalId\":302,\"journal\":{\"name\":\"Dyes and Pigments\",\"volume\":\"240 \",\"pages\":\"Article 112849\"},\"PeriodicalIF\":4.1000,\"publicationDate\":\"2025-04-21\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Dyes and Pigments\",\"FirstCategoryId\":\"88\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0143720825002190\",\"RegionNum\":3,\"RegionCategory\":\"工程技术\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, APPLIED\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Dyes and Pigments","FirstCategoryId":"88","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0143720825002190","RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
High efficiency and long device lifetime of organic light-emitting diodes using new electron-transporting materials with spirobifluorene groups
In this study, novel electron transport layer (ETL) materials, 2-([1,1′-biphenyl]-2-yl)-4-(dibenzo [b,d]furan-4-yl)-6-(9,9-diphenyl-9H-fluoren-4-yl)-1,3,5-triazine (DFDDT) and 2-(9,9′- spirobi [fluoren]-4-yl)-4-([1,1′-biphenyl]-2-yl)-6-(dibenzo [b,d]furan-4-yl)-1,3,5-triazine (SFDDT), were synthesized and their electrical and optical properties were investigated for application in blue organic light emitting diodes devices. The triazine core, known for its strong electron-withdrawing properties, was utilized as the central framework. To enhance both thermal stability and electron-withdrawing capability, dibenzofuran (DBF) was incorporated, while an o-biphenyl group was introduced to regulate molecular morphology. By incorporating a spirobifluorene structure, SFDDT significantly enhanced thermal stability while preserving the optical properties of DFDDT, achieving a high glass transition temperature (Tg, 141 °C) and thermal decomposition temperature (Td, 436 °C). The electron mobility of n-doped ETL (N-ETL) measurements showed that SFDDT exhibited a value of 6.329 × 10−5 cm2V−1s−1, approximately 1.9 times higher than that of the commercial ETL material 3,3'-(5'-(3-(pyridin-3-yl)phenyl)-[1,1':3′,1''-terphenyl]-3,3''-diyl)dipyridine (TmPyPB). When applied as an ETL, the device demonstrated a current efficiency (CE) of 5.47 cd/A and an external quantum efficiency (EQE) of 6.73 % at 10 mA/cm2, along with a significantly extended lifetime (LT95) of 135 h—more than 20 times longer than that of TmPyPB. The molecular design strategy incorporating spirobifluorene in ETL materials not only presents a new approach for ETL material development but also confirms its applicability in long-lifetime applications such as large-screen televisions (TVs), information technology (IT) devices, and automotive display systems.
期刊介绍:
Dyes and Pigments covers the scientific and technical aspects of the chemistry and physics of dyes, pigments and their intermediates. Emphasis is placed on the properties of the colouring matters themselves rather than on their applications or the system in which they may be applied.
Thus the journal accepts research and review papers on the synthesis of dyes, pigments and intermediates, their physical or chemical properties, e.g. spectroscopic, surface, solution or solid state characteristics, the physical aspects of their preparation, e.g. precipitation, nucleation and growth, crystal formation, liquid crystalline characteristics, their photochemical, ecological or biological properties and the relationship between colour and chemical constitution. However, papers are considered which deal with the more fundamental aspects of colourant application and of the interactions of colourants with substrates or media.
The journal will interest a wide variety of workers in a range of disciplines whose work involves dyes, pigments and their intermediates, and provides a platform for investigators with common interests but diverse fields of activity such as cosmetics, reprographics, dye and pigment synthesis, medical research, polymers, etc.