Strongly Fluorescent and Thermally Stable Functional Polybenzoxazole Film:  Excited-State Intramolecular Proton Transfer and Chemically Amplified Photopatterning

Park, Sanghyuk; Kim, Sehoon; Seo, Jangwon; Park, Soo Young

doi:10.1021/ma050009r

Cited by 57 publications

(45 citation statements)

References 24 publications

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“…This deep-blue electroluminescence can be understood as electrically generated ESIPT in the central emitting part: the exciton is first produced in the predominantly existing E form by the recombination of a hole and an electron within the EML, which quickly decays to the excited-state K form by effective proton transfer in the film state, followed by radiative relaxation of the excited K form. [33][34][35][36] The current-voltage-luminance characteristics of two device structures with HPI-Cbz and HPI-Oxd are shown in Figure 3. The turn-on voltages of device (a) using HPI-Cbz and (b) HPI-Oxd (see Figure 2) were 4.8 and 3.6 V, respectively.…”

Section: Resultsmentioning

confidence: 99%

Tetraphenylimidazole‐Based Excited‐State Intramolecular Proton‐Transfer Molecules for Highly Efficient Blue Electroluminescence

Park

Seo

Kim

et al. 2008

Adv Funct Materials

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105

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Aiming for highly efficient blue electroluminescence, we have designed and synthesized a novel class of tetraphenylimidazole‐ based excited‐state intramolecular proton‐transfer (ESIPT) molecules with covalently linked charge‐transporting functional groups (carbazole‐ and oxadiazole‐functionalized hydroxyl‐substituted tetraphenylimidazole (HPI), i.e., HPI‐Cbz and HPI‐Oxd, respectively). High Tg (ca. 130 °C) amorphous films of HPI‐Cbz and HPI‐Oxd showed intense and ideal blue‐light emission (λmax = 462 and 468 nm, ΦPL = 0.44 and 0.38) with a large Stokes shift of over 160 nm and a narrow full width at half‐maximum of less than 65 nm. Organic light‐emitting devices using HPI‐Cbz and HPI‐Oxd as the emitting layer generated an efficient blue electroluminescence (EL) emission peaking at around 460 nm with excellent CIE coordinates of (x, y) = (0.15, 0.11). A maximum external quantum efficiency of 2.94%, and a maximum brightness of 1 229 cd m−2 at 100 mA cm−2, as well as a low turn‐on voltage of 4.8 V were achieved in this work.

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Section: Resultsmentioning

confidence: 99%

Tetraphenylimidazole‐Based Excited‐State Intramolecular Proton‐Transfer Molecules for Highly Efficient Blue Electroluminescence

Park

Seo

Kim

et al. 2008

Adv Funct Materials

Self Cite

105

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“…[ 78 ] Recently, novel strategies for achieving high-performance fl uorescence imaging and optical recording have been developed which make use of the unique and beneficial characteristics of ESIPT process. [79][80][81] In principle, ESIPT reaction and its unique properties are associated with a "proton" transfer from proton donor to proton acceptor. The ESIPT process, therefore, can be inhibited by simply removing the proton of the donor, which brings about a great fl uorescence emission change of ESIPT molecules in terms of different Stokes' shift and fl uorescence effi ciency.…”

Section: Fluorescence Imaging Toward Optical Recording and Memorymentioning

confidence: 99%

“…Park and his colleagues successfully demonstrated the fl uorescence photopatterning of PBHBO-BOC fi lm by t-BOC cleavage induced ESIPT modulation based on the chemical amplifi cation resist method ( Figure 16 a). [ 79 ] PBHBO absorbed UV light at 364 nm and emitted dual fl uorescence, composed of weaker E * emission at 470 nm and stronger K * emission at 597 nm. In contrast, the t-BOC blocked PBHBO-BOC showed dominant green emission at 524 nm with trace of blue emission due to energy transfer from 93% of diblocked moiety to 7% of monoblocked moiety.…”

Section: Fluorescence Imaging Toward Optical Recording and Memorymentioning

confidence: 99%

Advanced Organic Optoelectronic Materials: Harnessing Excited‐State Intramolecular Proton Transfer (ESIPT) Process

2011

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Recently, organic fluorescent molecules harnessing the excited-state intramolecular proton transfer (ESIPT) process are drawing great attention due to their unique photophysical properties which facilitate novel optoelectronic applications. After a brief introduction to the ESIPT process and related photo-physical properties, molecular design strategies towards tailored emission are discussed in relation to their theoretical aspects. Subsequently, recent studies on advanced ESIPT molecules and their optoelectronic applications are surveyed, particularly focusing on chemical sensors, fluorescence imaging, proton transfer lasers, and organic light-emitting diodes (OLEDs).

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“…47,48 To produce poly-(hydroxybenzoxazole) (PHBO), PAGs were exploited to deprotect the tBoc group in tBoc-blocked PHBO ESIPT is based on a fast enol to keto prototropy in the excited state between intramolecular hydrogenbonding interactions. 49 Thus, dual color fluorescence photo-patterning was achieved in a chemical amplification resist with the PAG, where the PHBO area emitted orange fluorescence while the PHBO-BOC region showed green emission.…”

Section: Other Applications Based On Pspbosmentioning

confidence: 99%

Recent Development of Photosensitive Polybenzoxazoles

Fukukawa

Ueda

2006

Polym J

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ABSTRACT:Photosensitive polybenzoxazoles (PSPBOs) have been attracting great attention as insulating materials in microelectronic industry, and can be directly patterned to simplify processing steps. This article reviews recent works on development of PSPBOs. After brief introduction, a typical formulation method of PSPBOs was described, followed by a facile synthetic method of a precursor of PBOs, highly sensitive PSPBOs, highly transparent poly(ohydroxy amide)s (PHAs), an efficient catalyst for low-temperature cyclization of PHA, and finally other applications of PSPBOs.

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Strongly Fluorescent and Thermally Stable Functional Polybenzoxazole Film: Excited-State Intramolecular Proton Transfer and Chemically Amplified Photopatterning

Cited by 57 publications

References 24 publications

Tetraphenylimidazole‐Based Excited‐State Intramolecular Proton‐Transfer Molecules for Highly Efficient Blue Electroluminescence

Tetraphenylimidazole‐Based Excited‐State Intramolecular Proton‐Transfer Molecules for Highly Efficient Blue Electroluminescence

Advanced Organic Optoelectronic Materials: Harnessing Excited‐State Intramolecular Proton Transfer (ESIPT) Process

Recent Development of Photosensitive Polybenzoxazoles

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