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1.
Developing red thermally activated delayed fluorescence (TADF) emitters, attainable for both high‐efficient red organic light‐emitting diodes (OLEDs) and non‐doped deep red/near‐infrared (NIR) OLEDs, is challenging. Now, two red emitters, BPPZ‐PXZ and mDPBPZ‐PXZ, with twisted donor–acceptor structures were designed and synthesized to study molecular design strategies of high‐efficiency red TADF emitters. BPPZ‐PXZ employs the strictest molecular restrictions to suppress energy loss and realizes red emission with a photoluminescence quantum yield (ΦPL) of 100±0.8 % and external quantum efficiency (EQE) of 25.2 % in a doped OLED. Its non‐doped OLED has an EQE of 2.5 % owing to unavoidable intermolecular π–π interactions. mDPBPZ‐PXZ releases two pyridine substituents from its fused acceptor moiety. Although mDPBPZ‐PXZ realizes a lower EQE of 21.7 % in the doped OLED, its non‐doped device shows a superior EQE of 5.2 % with a deep red/NIR emission at peak of 680 nm.  相似文献   

2.
Thermally activated delayed fluorescence (TADF)‐based organic light‐emitting diodes (OLEDs) have attracted enormous attention recently due to their capability to replace conventional phosphorescent organic light‐emitting diodes for practical applications. In this work, a newly designed CN‐substituted imidazopyrazine moiety was utilized as an electron‐accepting unit in a TADF emitter. Two TADF emitters, 8‐(3‐cyano‐4‐(9,9‐dimethylacridin‐10(9H)‐yl)phenyl)‐2‐phenylimidazo[1,2‐a]pyrazine‐3‐carbonitrile (Ac‐CNImPyr) and 8‐(3‐cyano‐4‐(10H‐phenoxazin‐10‐yl)phenyl)‐2‐phenylimidazo[1,2‐a]pyrazine‐3‐carbonitrile (PXZ‐CNImPyr), were developed based on the CN‐substituted imidazopyrazine acceptor combined with acridine and phenoxazine donor, respectively. A CN‐substituted phenyl spacer was introduced between the donor and acceptor for a sufficiently small singlet‐triplet energy gap (ΔEST) and molecular orbital management. Small ΔEST of 0.07 eV was achieved for the phenoxazine donor‐based PXZ‐CNImPyr emitter. As a result, an organic light‐emitting diode based on the PXZ‐CNImPyr emitter exhibited a high external quantum efficiency of up to 12.7 %, which surpassed the EQE limit of common fluorescent emitters. Hence, the CN‐modified imidazopyrazine unit can be introduced as a new acceptor for further modifications to develop efficient TADF‐based OLEDs.  相似文献   

3.
A series of green butterfly‐shaped thermally activated delayed fluorescence (TADF) emitters, namely PXZPM , PXZMePM , and PXZPhPM , are developed by integrating an electron‐donor (D) phenoxazine unit and electron‐acceptor (A) 2‐substituted pyrimidine moiety into one molecule via a phenyl‐bridge π linkage to form a D –π–A–π–D configuration. Changing the substituent at pyrimidine unit in these emitters can finely tune their emissive characteristics, thermal properties, and energy gaps between the singlet and triplet states while maintaining frontier molecular orbital levels, and thereby optimizing their optoelectronic properties. Employing these TADF emitters results in a green fluorescent organic light‐emitting diode (OLED) that exhibits a peak forward‐viewing external quantum efficiency (EQE) close to 25 % and a slow efficiency roll‐off characteristic at high luminance.  相似文献   

4.
《化学:亚洲杂志》2017,12(18):2494-2500
Donor–acceptor–donor (D–A–D)‐type thermally activated delayed fluorescence (TADF) emitters 5,5′‐bis{4‐[9,9‐dimethylacridin‐10(9H )‐yl]phenyl}‐2,2′‐bipyrimidine (Ac‐bpm) and 5,5′‐bis[4‐(10H ‐phenoxazin‐10‐yl)phenyl]‐2,2′‐bipyrimidine (Px‐bpm), based on the 2,2′‐bipyrimidine accepting unit, were developed and their TADF devices were fabricated. The orthogonal geometry between the donor unit and the 2,2′‐bipyrimidine accepting core facilitated a HOMO/LUMO spatial separation, thus realizing thermally activated delayed fluorescence. The exhibited electroluminescence ranged from green to yellow, depending on the donor unit, with maximum external quantum efficiencies of up to 17.1 %.  相似文献   

5.
Establishment of the structure–property relationships of thermally activated delayed fluorescence (TADF) materials has become a significant quest for the scientific community. Herein, two new donors, 10H‐benzofuro[3,2‐b]indole (BFI) and 10H‐benzo[4,5]thieno[3,2‐b]indole (BTI), have been developed and integrated with a aryltriazine acceptor to design the green TADF emitters benzofuro[3,2‐b]indol‐10‐yl)‐5‐(4,6‐diphenyl‐1,3,5‐triazin‐2‐yl)benzonitrile ( BFICNTrz ) and 2‐(10H‐benzo[4,5]thieno[3,2‐b]indol‐10‐yl)‐5‐(4,6‐diphenyl‐1,3,5‐triazin‐2‐yl)benzonitrile ( BTICNTrz ), respectively. The physicochemical and electroluminescence properties of the compounds were tuned by exchanging the heteroatom in the donor scaffold. Intriguingly, the electronegativity of the heteroatom and the ionization potential of the donor unit played vital roles in control of the singlet–triplet energy splitting and TADF mechanism of the compounds. Both compounds showed similar singlet excited states that originated from the charge transfer (CT) states (1CT), whereas the triplet excited states were tuned by the heteroatom in the donor unit. The origin of phosphorescence in the BTICNTrz emitter was CT emission from the triplet state (3CT), whereas that in the BFICNTrz emitter stemmed from the local triplet excited state (3LE). Consequently, BTICNTrz showed a small singlet–triplet energy splitting of 0.08 eV, compared with 0.26 eV for BFICNTrz . Thus, BTICNTrz showed efficient delayed fluorescence with a high quantum yield and a short delayed exciton lifetime, whereas BFICNTrz displayed weak delayed fluorescence with a relatively long lifetime. Furthermore, a BTICNTrz ‐based device exhibited a maximum external quantum efficiency (EQE) of 15.2 % and reduced efficiency roll‐off (12 %) compared with its BFICNTrz ‐based counterpart, which showed a maximum EQE of 6.4 % and severe efficiency roll‐off (55 %) at a practical brightness range of 1000 cd m?2. These results demonstrate that the choice of subunit plays a vital role in the design of efficient TADF emitters.  相似文献   

6.
Two efficient thermally activated delayed fluorescent (TADF) emitters were developed by utilizing CN-modified imidazopyridine as an acceptor unit. The CN-modified imidazopyridine acceptor was combined with either an acridine donor or a phenoxazine donor through a phenyl linker to produce two TADF emitters, Ac-CNImPy and PXZ-CNImPy. The acridine-based Ac-CNImPy emitter exhibited sky-blue emission with a CIE coordinate of (0.18, 0.38), whereas the phenoxazine-donor-based PXZ-CNImPy showed greenish-yellow emission with a CIE coordinate of (0.32, 0.58). A high photoluminescence quantum yield of 80 % was observed for the PXZ-CNImPy emitter compared with 40 % for the Ac-CNImPy emitter. Organic light-emitting diodes based on the PXZ-CNImPy emitter demonstrated high external quantum efficiency of 17.0 %. Hence, the CN-modified imidazopyridine unit can be considered as a useful electron acceptor for the future design of highly efficient TADF emitters.  相似文献   

7.
A novel molecular model of connecting electron‐donating (D) and electron‐withdrawing (A) moieties via a space‐enough and conjugation‐forbidden linkage (D‐Spacer‐A) is proposed to develop efficient non‐doped thermally activated delayed fluorescence (TADF) emitters. 10‐(4‐(4‐(4,6‐diphenyl‐1,3,5‐triazin‐2‐yl) phenoxy) phenyl)‐9,9‐dimethyl‐9,10‐dihydroacridine (DMAC‐o‐TRZ) was designed and synthesized accordingly. As expected, it exhibits local excited properties in single‐molecule state as D‐Spacer‐A molecular backbone strongly suppress the intramolecular charge‐transfer (CT) transition. And intermolecular CT transition acted as the vital radiation channel for neat DMAC‐o‐TRZ film. As in return, the non‐doped device exhibits a remarkable maximum external quantum efficiency (EQE) of 14.7 %. These results prove the feasibility of D‐Spacer‐A molecules to develop intermolecular CT transition TADF emitters for efficient non‐doped OLEDs.  相似文献   

8.
Despite the success of thermally activated delayed fluorescent (TADF) materials in steering the next generation of organic light‐emitting diodes (OLEDs), effective near infrared (NIR) TADF emitters are still very rare. Here, we present a simple and extremely high electron‐deficient compound, 5,6‐dicyano[2,1,3]benzothiadiazole (CNBz), as a strong electron‐accepting unit to develop a sufficiently strong donor‐acceptor (D?A) interaction for NIR emission. End‐capping with the electron‐donating triphenylamine (TPA) unit created an effective D?A?D type system, giving rise to an efficient NIR TADF emissive molecule (λem=750 nm) with a very small ΔEST of 0.06 eV. The electroluminescent device using this NIR TADF emitter exhibited an excellent performance with a high maximum radiance of 10020 mW Sr?1 m?2, a maximum EQE of 6.57% and a peak wavelength of 712 nm.  相似文献   

9.
Blue thermally activated delayed fluorescent (TADF) devices with short excited-state lifetime, high reverse intersystem crossing rate, and low-efficiency roll-off were developed by managing the molecular structure of donor–acceptor-type blue emitters. Three isomers of blue TADF emitters with a diphenyltriazine acceptor and three carbazole donors were synthesized. The position of the donor moieties in the phenyl linker connecting the donor and acceptor moieties was controlled to devise compounds with a short delayed fluorescence lifetime. A blue TADF emitter with three carbazole donors at 2-, 3-, and 4- positions of a phenyl linker shortened the excited state lifetime to 4.1 μs, showed a high external quantum efficiency of 20.4 %, and low efficiency roll-off of less than 10 % at 1000 cd m−2. Therefore, a molecular design distorting the donors by aligning them in a consecutive way is useful to resolve the issues of long delayed fluorescence lifetime and efficiency roll-off of blue TADF devices.  相似文献   

10.
Three sets of conjugated polymers with backbone‐donor/pendant‐acceptor architectures, named PCzA3PyB, PCzAB2Py, and PCzAB3Py, are designed and synthesized. The three isomeric benzoylpyridine‐based pendant acceptor groups are 6‐benzoylpyridin‐3‐yl (3PyB), 4‐((pyridin‐2‐yl)carbonyl)phenyl (B2Py) and 4‐((pyridin‐3‐yl)carbonyl)phenyl (B3Py), whereas the identical backbone consists of 3,6‐carbazolyl and 2,7‐acridinyl rings. One acridine ring and each acceptor group constitute a definite thermally activated delayed fluorescence (TADF) unit, incorporated into the main chain of the polymers through the 2,7‐position of the acridine ring with the varied content. All of the polymers display legible TADF features with a short microsecond‐scale delayed lifetime (0.56–1.62 μs) and a small singlet/triplet energy gap (0.10–0.19 eV). Progressively redshifted emissions are observed in the order PCzAB3Py, PCzA3PyB, and PCzAB2Py owing to the different substitution patterns of the pyridyl group. Photoluminescence quantum yields can be improved by regulating the molar content of the TADF unit in the range 0.5–50 %. The non‐doped organic light‐emitting devices (OLEDs) fabricated by solution‐processing technology emit yellow‐green to orange light. The polymers with 5 mol % of the TADF unit exhibit excellent comprehensive electroluminescence performance, in which PCzAB2Py5 achieves a maximum external quantum efficiency (EQE) of 11.9 %, low turn‐on voltage of 3.0 V, yellow emission with a wavelength of 573 nm and slow roll‐off with EQE of 11.6 % at a luminance of 1000 cd m?2 and driving voltage of 5.5 V.  相似文献   

11.
In this work, a design approach of three thermally activated delayed fluorescence (TADF) emitters to extend the device lifetime of the TADF sensitized fluorescent devices was studied. Three TADF materials, 5-{4,6-bis[4-(tert-butyl)phenyl]-1,3,5-triazin-2-yl}-2-(10,15-diphenyl-10,15-dihydro-5H-diindolo[3,2-a:3′,2′-c]carbazol-5-yl)benzonitrile (tTCNTruX), 4-[3-cyano-4-(10,15-diphenyl-10,15-dihydro-5H-diindolo[3,2-a:3′,2′-c]carbazol-5-yl)phenyl]-2,6-diphenylpyrimidine-5-carbonitrile (PCNTruX) and 4-(4-{10,15-bis[4-(tert-butyl)phenyl]-10,15-dihydro-5H-diindolo[3,2-a:3′,2′-c]carbazol-5-yl}-3-cyanophenyl)-2,6-diphenylpyrimidine-5-carbonitrile (PCNtTruX), were synthesized as sensitizers for TADF-sensitized fluorescent organic light-emitting diodes. The two tTCNTruX and PCNtTruX TADF emitters were designed to have Dexter energy transfer with blocking groups either in the donor or acceptor unit of the donor–acceptor-type TADF sensitizer. The TADF materials showed small singlet–triplet energy splitting and a high reverse intersystem crossing (RISC) rate for effective sensitization of the fluorescent emission of the fluorescent emitter. tTCNTruX- and PCNtTruX-sensitized fluorescent devices showed maximum external quantum efficiencies (EQEs) of 17.7 % and 11.5 % in the yellow and red devices, respectively, which were higher than those of TADF-sensitized devices with the corresponding TADF sensitizer without a blocking group. Moreover, the device lifetime was also extended by employing the tTCNTruX and PCNtTruX sensitizers. This work demonstrated that the tTCNTruX and PCNtTruX sensitizers are effective to improve the maximum EQE and device lifetime of TADF-sensitized fluorescent devices.  相似文献   

12.
Formylphenyl has been demonstrated to act as an acceptor to construct thermally activated delayed fluorescence (TADF) emitter, and therefore a series of the TADF‐conjugated polymers with formylphenyl as pendant acceptor and carbazole/acridine as backbone donor are designed and synthesized. All polymers involve the twisted donor/acceptor structural moieties with the sufficiently spatial separation between the highest occupied molecular orbital and the lowest unoccupied molecular orbital as well as a small singlet/triplet splitting, and exhibit the legible TADF features confirmed by theoretical calculation and their transient decay spectra. The solution‐processed organic light‐emitting diodes using neat film of the polymers as emissive layer achieve excellent performance with the maximum external quantum efficiency (EQE) of up to 10.6%, the maximum current efficiency of up to 35.3 cd A−1 and the low turn‐on voltage of 2.7 V. Moreover, the EQE still remains 10.3% at the luminance of 1000 cd m−2 with the low driving voltage of 4.4 V and extremely small efficiency roll‐off. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018 , 56, 1989–1996  相似文献   

13.
A new donor moiety, 7,7,13,13‐tetramethyl‐7,13‐dihydro‐5H‐indeno[1,2‐b]acridine (IAc), was developed to control the highest occupied molecular orbital (HOMO) dispersion of thermally activated delayed fluorescent (TADF) emitters. The IAc unit expanded the HOMO dispersion of the emitters and increased the quantum efficiency of the TADF devices up to 20.9 %.  相似文献   

14.
《中国化学快报》2023,34(6):107634
Through-space charge transfer (TSCT) is regarded as an effective way to develop thermally activated delayed fluorescence (TADF) emitters. Based on this strategy, many molecular frameworks have been proposed, among which spirobased scaffolds have been extensively studied due to their unique advantages. In this work, we developed three emitters SPS, SPO, and SPON, which were constructed with the same donor and various acceptors to explore the influence of acceptor modulation at the C9 position of fluorene for spirostructure TSCT emitters. The results show that the acceptor with too weak electron-withdrawing ability will cause the emitter to not have TADF properties, while the acceptor with too much steric hindrance will weaken the face-to-face π-π stacking interaction between donor/acceptor (D/A). Since SPO balances the electron-withdrawing strength and steric hindrance of the acceptor, it achieves the highest external quantum efficiency (EQE) of 17.75%. This work shows that appropriate acceptor selection is essential for the TADF properties and high efficiency of the spirobased scaffold TSCT emitter  相似文献   

15.
A new family of thermally activated delayed fluorescence (TADF) emitters based on U‐shaped D‐A‐D architecture with a novel accepting unit has been developed. All investigated compounds have small singlet‐triplet energy splitting (ΔEST) ranging from 0.02 to 0.20 eV and showed efficient TADF properties. The lowest triplet state of the acceptor unit plays the key role in the TADF mechanism. OLEDs fabricated with these TADF emitters achieved excellent efficiencies up to 16 % external quantum efficiency (EQE).  相似文献   

16.
Donor–acceptor (D–A) molecular architecture has been shown to be an effective strategy for obtaining high‐performance electroluminescent materials. In this work, two D–A molecules, Ph‐BPA‐BPI and Py‐BPA‐BPI, have been synthesized by attaching highly fluorescent phenanthrene or pyrene groups to the C6‐ and C9‐positions of a locally excited‐state emitting phenylamine–phenanthroimidazole moiety. Equipped with good physical and hybridized local and charge‐transfer properties, both molecules show high performances as blue emitters in nondoped organic light‐emitting devices (OLEDs). An OLED using Ph‐BPA‐BPI as the emitting layer exhibits deep‐blue emission with CIE coordinates of (0.15, 0.08), and a maximum external quantum efficiency (EQE), current efficiency (CE), and power efficiency (PE) of 4.56 %, 3.60 cd A?1, and 3.66 lm W?1, respectively. On the other hand, a Py‐BPA‐BPI‐based, sky‐blue OLED delivers the best results among nondoped OLEDs with CIEy values of < 0.3 reported so far, for which a very low turn‐on voltage of 2.15 V, CIE coordinates of (0.17, 0.29), and maximum CE, PE, and EQE values of 10.9 cd A?1, 10.5 lm W?1, and 5.64 %, were achieved, respectively. More importantly, both devices show little or even no efficiency roll‐off and high singlet exciton‐utilizing efficiencies of 36.2 % for Ph‐BPA‐BPI and 39.2 % for Py‐BPA‐BPI.  相似文献   

17.
Recently, researchers have focused on thermally activated delayed fluorescence (TADF) for efficient future lighting and displays. Among TADF emitters, a combination of triazine and acridine is a promising candidate for realizing high-efficiency organic light-emitting devices (OLEDs). However, simultaneous development of perfect horizontal orientation (Θ=100 %) and an external quantum efficiency (EQE) of over 40 % is still challenging. Here, to obtain insights for further improvements of a triazine/acridine combination, various asymmetric spirobiacridine (SBA)-based TADF emitters with a unity photoluminescence quantum yield and high Θ ratio of over 80 % were developed. Furthermore, the substitution effects of the triazine acceptor unit on the photophysical properties were studied, including molecular orientations and OLED performance. The corresponding OLED exhibited sky-blue emission with a high EQE of over 30 %.  相似文献   

18.
A series of blue thermally activated delayed fluorescent (TADF) emitters of 1′′-(4,6-diphenyl-1,3,5-triazin-2-yl)-9,9′′-diphenyl-9H,9′′H-3,3′:9′,4′′-tercarbazole (TrzCz1) and 3′,6′-di-tert-butyl-1-(4,6-diphenyl-1,3,5-triazin-2-yl)-9-phenyl-9H-4,9′-bicarbazole (TrzCz2) were synthesized through a molecular design approach to decorate phenylcarbazole with a donor and an acceptor. The 1- and 4-positions of the phenylcarbazole core were modified with a diphenyltriazine acceptor and a bicarbazole or tert-butylcarbazole donor, respectively, through a synthetic strategy to introduce Br at the 1-position and F at the 4-position. The TrzCz1 and TrzCz2 emitters showed maximum photoluminescence emission bands at λ=443 and 433 nm, which were blueshifted relative to those of the corresponding TADF emitters with the same donor and acceptor, respectively. In the device application, the TrzCz1 emitter showed a maximum external quantum efficiency of 22.4 %, with a color coordinate of (0.16, 0.21), and the TrzCz2 emitter showed a maximum external quantum efficiency of 9.9 %, with a color coordinate of (0.14, 0.09). This work proved that the design strategy of decorating phenylcarbazole with a donor and an acceptor is effective at blueshifting the emission of TADF emitters.  相似文献   

19.
Blue thermally activated delayed fluorescence (TADF) emitters that can simultaneously achieve high efficiency in doped and nondoped organic light‐emitting diodes (OLEDs) are rarely reported. Reported here is a strategy using a tri‐spiral donor for such versatile blue TADF emitters. Impressively, by simply extending the nonconjugated fragment and molecular length, aggregation‐caused emission quenching (ACQ) can be greatly alleviated to achieve as high as a 90 % horizontal orientation dipole ratio and external quantum efficiencies (EQEs) of up to 33.3 % in doped and 20.0 % in nondoped sky‐blue TADF‐OLEDs. More fascinatingly, a high‐efficiency purely organic white OLED with an outstanding EQE of up to 22.8 % was also achieved by employing TspiroS‐TRZ as a blue emitter and an assistant host. This compound is the first blue TADF emitter that can simultaneously achieve high electroluminescence (EL) efficiency in doped, nondoped sky‐blue, and white TADF‐OLEDs.  相似文献   

20.
Benzofurocarbazole moieties are commonly used donor structures in the design of thermally activated delayed fluorescence (TADF) emitters. However, only 5 H-benzofuro[3,2-c]carbazole (34BFCz) has been reported and, to the best of our knowledge, no other benzofurocarbazole derivatives have been covered in the literature. In the present study, two further benzofurocarbazole moieties, 12 H-benzofuro[3,2-a]carbazole (12BFCz) and 7 H-benzofuro[2,3-b]carbazole (23BFCz), have been synthesized to investigate the effect of the donor structure on the photophysics and device parameters of TADF emitters. Two benzofurocarbazole-derived TADF emitters, 12-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-12 H-benzofuro[3,2-a]carbazole (o12BFCzTrz) and 7-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-7 H-benzofuro[2,3-b]carbazole (o23BFCzTrz), have been compared with 5-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-5 H-benzofuro[3,2-c]carbazole (oBFCzTrz). The benzofurocarbazole donor structure governs the TADF characteristics, such as charge-transfer property and emission color. The 12BFCz donor has proved to be effective in blue-shifting the emission color, and 34BFCz has proven useful for improving the external quantum efficiency (EQE). The 12BFCz-derived o12BFCzTrz showed blue-shifted color coordinates of (0.159, 0.288), compared to (0.178, 0388) for o23BFCzTrz and (0.169, 0.341) for oBFCzTrz. The 34BFCz-derived oBFCzTrz exhibited an EQE of 22.9 %, compared to 19.2 % for o12BFCzTrz and 21.1 % for o23BFCzTrz.  相似文献   

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