Modulation of Physical Properties of Ter(9,9-ditolylfluorene) by Backbone-Embedded Heteroarenes

Wong, Ken‐Tsung; Hwu, Tsyr-Yuan; Balaiah, A.; Chao, Teng‐Chih; Fang, Fu-Chuan; Lee, and Ching-Tien; Peng, Ying-Chu

doi:10.1021/ol060183f

Cited by 52 publications

(27 citation statements)

References 15 publications

(8 reference statements)

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“…[10] Various terfluorenyl derivatives have hence been investigated over the last ten years not only for blue OLEDs [11][12][13][14] but also for lightemitting OFETs (LE-OFETs). [15] As the molecular structure of the active layer is of key importance in LE-OFET and OLED devices, different molecular designs of the terfluorenyl backbone have thus been developed, including the incorporation of heterocycles, [16][17][18] hydroxyaminophenyl side chains, [19] cyclopropane, [20] and spiro bridges. [10-12, 15, 16, 21, 22] The introduction of a spiro bridge into small molecules is indeed an efficient strategy to reduce the crystallization tendency of the materials, enhancing their solubility, thermal stability, and quantum yield.…”

Section: Introductionmentioning

confidence: 99%

Blue Emitting 3 π–2 Spiro Terfluorene–Indenofluorene Isomers: A Structure–Properties Relationship Study

Poriel

Rault‐Berthelot

Thirion

et al. 2011

Chemistry A European J

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Two novel terfluorenyl derivatives, 2,2'',7,7''-tetrakis(9,9-dioctyl-9H-fluoren-2-yl)dispiro[fluorene-9,11'-indeno-(2,1-a)-fluorene-12',9''-fluorene] ((2,1-a)-DST-IF) and 2,2'',7,7''-tetrakis(9,9-dioctyl-9H-fluoren-2-yl)dispiro- [fluorene-9,6'-indeno-(1,2-b)-fluorene-12',9''-fluorene] ((1,2-b)-DST-IF) have been synthesized by two different synthetic approaches. These terfluorenyl derivatives possess a different central indenofluorene core, namely (2,1-a)-indenofluorene or (1,2-b)-indenofluorene, which imposes two distinct geometry profiles, and different structural environments for the terfluorenyl fluorophores that translates into drastically different optical and electrochemical properties for (2,1-a)-DST-IF and (1,2-b)-DST-IF. These properties have been carefully studied through a combined experimental and theoretical approach. The (2,1-a)-DST-IF isomer has been successfully used as emitting layer in a blue single-layer small-molecule organic light-emitting diode (SMOLED) and appears as the first example of a blue emission arising from intramolecular terfluorenyl excimers. Regarding the importance of terfluorenyl derivatives in organic electronics, the present structure-properties relationship study, may open new avenues in the design of efficient blue fluorophores.

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Section: Introductionmentioning

confidence: 99%

Blue Emitting 3 π–2 Spiro Terfluorene–Indenofluorene Isomers: A Structure–Properties Relationship Study

Poriel

Rault‐Berthelot

Thirion

et al. 2011

Chemistry A European J

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“…The higher-lying HOMO energy levels of these fluorene-incorporated benzo[c]heterocycles ($5.2 eV) greatly reduce the energy barrier for hole injection from ITO (u = 4.8 eV) to emissive Alq 3 (u = 4.8 eV), hence, these heterocycles should be explored as hole-transporting materials for double-layer OLEDs. n-C 6 H 13 n-C 6 H 13 Se 8a R 1 = H, R 2 = H (59%) 8b R 1 = n-C 6 H 13, R 2 = H (62%) 8c R 1 = H, R 2 = n-C 6 …”

Section: Contents Lists Available At Sciencedirectmentioning

confidence: 99%

“…5 Wong and co-workers reported the synthesis and photophysical studies of 9,9-ditolylfluorene analogs containing thiophene rings. 6 Numerous examples of benzo[c]thiophene 1 (Fig. 1) …”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of 9,9-dialkylfluorene capped benzo[c]thiophene/benzo[c]selenophene analogs as potential OLEDs

Mohanakrishnan

Kumar

Amaladass

2008

Tetrahedron Letters

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“…Both the non‐doped and doped OLEDs employing TBPSF exhibited good device performance at that time. Some other terfluorene analogues TF1∼3 (Scheme ) embedded with heteroarene in the conjugated backbone were also synthesized to modulate the optical properties of T3 . The absorption and emission of TF‐1 and TF‐3 were found to be bathochromically shifted as compared to those of parent T3 due to the quinoidal character of thiophene introduced as the conjugated constituent.…”

Section: Fluorescent Blue Materials: Fluorene Derivatives With Introdmentioning

confidence: 99%

Development of Materials for Blue Organic Light Emitting Devices

Sarma

Wong

2019

The Chemical Record

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The success of organic light emitting diodes (OLED) has been witnessed by the commercialization of this technology for manufacturing the vivid and colorful displays used in our daily life now. The prospective growth of OLED technology on display industry will be optimistic. Over the last three decades, many different approaches on material and device designs have been implemented for improving the efficiency and stability of OLED devices. These efforts install main cornerstones to support the great achievement of OLED technology. However, until now, the performance and stability of blue OLEDs still have some concerns. This troublesome issue should be totally conquered before the large-scale manufactures dominated over other display technologies, particularly liquid crystal-based displays, takes place. Though significant progress has already been made to achieve high performance and long lifetime blue OLEDs, this topic still remains as one of the hot researches in OLEDs. We have been working on this area for about two decades and made some notable contributions. Consequently, in this personal account we have outlined our efforts to obtain better performing blue OLEDs by utilizing a range of emitters based on fluorescence, phosphorescence, delayed fluorescence and exciplex systems. We have also developed some novel host materials for blue OLEDs, which are worth mentioning in this account.Keywords: blue fluorescent emitter, phosphorescent complex, delayed fluorescence, exciplex, bipolar host materials [a] M.

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Modulation of Physical Properties of Ter(9,9-ditolylfluorene) by Backbone-Embedded Heteroarenes

Cited by 52 publications

References 15 publications

Blue Emitting 3 π–2 Spiro Terfluorene–Indenofluorene Isomers: A Structure–Properties Relationship Study

Blue Emitting 3 π–2 Spiro Terfluorene–Indenofluorene Isomers: A Structure–Properties Relationship Study

Synthesis and characterization of 9,9-dialkylfluorene capped benzo[c]thiophene/benzo[c]selenophene analogs as potential OLEDs

Development of Materials for Blue Organic Light Emitting Devices

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