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1.
Angew Chem Int Ed Engl ; 62(1): e202214424, 2023 Jan 02.
Artigo em Inglês | MEDLINE | ID: mdl-36331071

RESUMO

White circularly polarized organic light-emitting diodes (CP-WOLEDs) are of great significance in potential lighting sources and full-color 3D displays. However, High-performance white CP-EL sources are almost unexplored. We have constructed full-color CP-EL devices based on chiral co-assemblies by using three achiral conjugated pyrene-based dyes (BP, w-WP and c-WP) doped with chiral binaphthyl-based enantiomers (S-/R-M) as the EMLs through an intermolecular chirality induction mechanism. (S-/R-M)0.2 -(c-WP)0.8 films exhibit regular helix nanofibers under annealing treatment and emit strong white CPL. Significantly, remarkable CP-WOLEDs based on (S-/R-M)0.2 -(c-WP)0.8 were achieved with |gEL | values as high as 6.2×10-2 and an excellent CRI of 98 at the CIE coordinates of (0.33, 0.33). These are the highest gEL and CRI values of reported CP-WOLEDs to date. This is the first achievement of CP-WOLEDs based on chiral co-assembled helix nanofiber emitters, and provides a valuable strategy with which to develop white CP-EL for future practical applications.

2.
Chemistry ; 27(2): 589-593, 2021 Jan 07.
Artigo em Inglês | MEDLINE | ID: mdl-32881099

RESUMO

By combining the blue and orange CPL or functionalized bis-benzoxanethones emitters (S-/R-BN-tCz and S-/R-BN-PXZ), warm white CP-OLEDs were fabricated using solution-processed single emitting layer strategy. The successful realization of white CP-EL benefited from the same stable binaphthyl chirality and similar rigid structure of the two emissive CPL emitters. The devices exhibited the low turn-on voltage of ≈4.3 V, maximum luminance of ≈10200 cd m-2 and maximum current efficiency of ≈2.0 cd A-1 . Most significantly, the devices with CIE coordinates of (0.32, 0.45) displayed intense CP-EL signals in the spectral range of 450 to 650 nm, and showed stable gEL values of ≈10-3 as the luminance increased from 100 to 6000 cd m-2 . To the best of our knowledge, this work provides for the first time a simple and feasible strategy to fabricate solution-processed white CP-OLEDs based on the co-doping of the CPL emitters.

3.
Inorg Chem ; 60(17): 13359-13365, 2021 Sep 06.
Artigo em Inglês | MEDLINE | ID: mdl-34492766

RESUMO

A multidentate tetrazole molecule based on a TPE core, tetrakis[4-(1H-tetrazol-5-yl)phenyl]ethylene (H4ttpe) with combined advantages of two functional groups, was synthesized by cycloaddition reaction of the corresponding organic benzonitrile derivative and azide salt. Coordination self-assembly of the in situ formed aggregation-induced emission polytetrazole luminogen with cadmium(II) ion produces an unprecedented tetrazolyl-TPE-based microporous cationic metal-organic framework (MOF) with an unusual (4,5,8T14)-connected net of {[Cd4(H4ttpe)2Cl5]·(N3)3}, in which the H4ttpe serves as the first undeprotonated tetrazole ligand of octa-coordinating bridging mode. We investigate, for the first time, the utilization of the luminescent MOF containing a TPE core decorated with tetrazolyl terminals for explosive detection based on the change in fluorescence intensity, which shows high selectivity and efficiency in fluorescence quenching toward TNP detection in water solution.

4.
J Nanosci Nanotechnol ; 18(8): 5534-5541, 2018 Aug 01.
Artigo em Inglês | MEDLINE | ID: mdl-29458607

RESUMO

Two thienoisoindigo-based donor-acceptor conjugated polymers were synthesized via Sonogashira coupling reaction with 1,4-diethynylbenzene (P(TII-BEN)) and 9,10-diethynylanthracene (P(TII-ANT)) as donor units, respectively. The optical and electrochemical properties of the polymers were also investigated. The highest hole mobility were 4.38 × 10-3 cm2 V-1 s-1 for P(TII-BEN) and 9.40 × 10-3 cm2 V-1 s-1 for P(TII-ANT) in bottom-gated/top-contact field-effect transistors. The bulk heterojunction organic solar cells consisting of the polymers and PC71BM yielded power conversion efficiencies of 1.59% for P(TII-BEN) and 1.90% for P(TII-ANT). Moreover, the microstructures were investigated by X-ray diffraction and atomic force microscopy.

5.
Small ; 12(47): 6623-6632, 2016 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-27671549

RESUMO

Silole derivatives, the first reported and famous AIEgens, are a series of Si-containing conjugated rings with the σ*-π* conjugation, and this unique electronic structure imparts them high electron affinity and fast electron mobility, but not ideal blue luminogens due to their relatively long conjugation length. By replacing the Si atom with the C one, six new AIEgens without the σ*-π* conjugation effect are successfully synthesized based on a tetraphenylcyclopentadiene core. In addition to the sky-blue emission (λEL = 492 nm) with Lmax , ηC,max , and ηP,max up to 24 096 cd m-2 , 6.80 cd A-1 , and 4.07 lm W-1 , respectively, the careful control of the conjugation degree by changing the linkage mode, results in the blue one (λEL = 440 nm) with relatively good performance (Lmax : 8721 cd m-2 and ηC,max : 3.40 cd A-1 ), indicating that the replacement of the Si atom by C one is an alternative design strategy to yield blue even deep-blue AIEgens with good device performance. Meanwhile, their reversible mechanochromic properties are realized with apparent fluorescence changes between deep-blue and green emissive colors, offering them additional promising applications in optoelectronic devices.

6.
Phys Chem Chem Phys ; 17(14): 8860-9, 2015 Apr 14.
Artigo em Inglês | MEDLINE | ID: mdl-25742776

RESUMO

Low cost and high performance white polymer light-emitting diodes (PLEDs) are very important as solid-state lighting sources. In this research three commercially available phosphors were carefully chosen, bis[2-(4,6-difluorophenyl)pyridinato-N,C(2)](picolinate)iridium(III) (FIrpic), bis[2-(2-pyridinyl-N)phenyl-C](2,4-pentanedionato-O(2),O(4))iridium(III) [Ir(ppy)2(acac)], and bis(2-phenyl-benzothiazole-C(2),N)(acetylacetonate)iridium(III) [Ir(bt)2(acac)], plus a home-made red phosphor of tris[1-(2,6-dimethylphenoxy)-4-(4-chlorophenyl)phthalazine]iridium(III) [Ir(MPCPPZ)3], and their photophysical and morphological properties were systematically studied as well as their applications in single-emission layer white PLEDs comprising poly(N-vinylcarbazole) as host. Additionally, the electrochemical properties and energy level alignment, possible energy transfer process, and thin-film morphology were also addressed. The binary blue/orange complementary white PLEDs exhibit stable electroluminescence spectra, wide spectrum-covering region range from 380-780 nm, and high color rendering index (CRI) over 70 with Commission Internationale de l'Eclairage coordinates x,y (CIEx,y) of (0.388, 0.440), correlated color temperature (CCT) of around 4400, plus high efficiency of 25.5 cd A(-1). The optimized red-green-blue white PLEDs showed a satisfactory CRI of around 82.4, maximum current efficiency of 20.0 cd A(-1) and external quantum efficiency (EQE) of 10.8%, corresponding to a CCT of 3700-2800, which is a warm-white hue. At last, stable and high color quality, red-green-orange-blue four component white PLEDs, with a CRI of over 82, a high efficiency of 24.0 cd A(-1), EQE of 11.5%, and high brightness of 43,569.9 cd m(-2) have been obtained.

7.
Chemistry ; 20(18): 5317-26, 2014 Apr 25.
Artigo em Inglês | MEDLINE | ID: mdl-24665038

RESUMO

Two aggregation-induced emission active luminogens (TPE-pTPA and TPE-mTPA) were successfully synthesized. For comparison, another six similar compounds were prepared. Because of the introduced hole-dominated triphenylamine (TPA), fluorene groups with high luminous efficiency, and unconjugated linkages, the π conjugation length of the obtained luminogens is effectively restricted to ensure their blue emission. The undoped organic light-emitting diodes based on TPE-pTPA and TPE-mTPA exhibited blue or deep-blue emissions, low turn-on voltages (3 V), and high electroluminescence efficiencies with Lmax, ηC,max, and ηP,max values of up to 26,697 cd m(-2), 3.37 cd A(-1), and 2.40 Lm W(-1).

8.
Macromol Rapid Commun ; 33(2): 164-71, 2012 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-22134953

RESUMO

With the aim to develop new tetraphenylethylene (TPE)-based conjugated hyperbranched polymer, TPE units, one famous aggregation-induced emission (AIE) active group, are utilized to construct hyperbranched polymers with three other aromatic blocks, through an "A2+B4" approach by using one-pot Suzuki polycondensation reaction. These three hyperbranched polymers exhibit interesting AIEE behavior and act as explosive chemsensors with high sensitivity both in the nanoparticles and solid states. This is the first report of the AIE activity of the TPE-based conjugated hyperbranched polymers. Their corresponding PLED devices also demonstrate good performance.


Assuntos
Substâncias Explosivas/análise , Fluorescência , Polietilenos/química , Polietilenos/síntese química
9.
ACS Appl Mater Interfaces ; 13(21): 25186-25192, 2021 Jun 02.
Artigo em Inglês | MEDLINE | ID: mdl-34014633

RESUMO

This work describes the construction of a novel planar chiral [2.2]paracyclophane-based thermally activated delayed fluorescence (TADF)-active molecule with circularly polarized luminescence (CPL). The combination of the bulky planar chiral phenoxazinephane (PXZp) donor based [2.2]paracyclophane and triazine acceptor enables the highly efficient luminescence performances and excellent CPL properties. The enantiomers exhibit excellent TADF activities, the energy difference (ΔEST) between singlet and triplet of the molecule is only 0.03 eV. Notably, through solution-process, a yellow CP-OLEDs based on the molecule as the emitting layers displays high maximum brightness (Lmax) up to 34 293 cd m-2, maximum external quantum efficiency (EQEmax) up to 7.8% and remarkable CP-EL signal with gEL factor up to 4.6 × 10-3.

10.
Chemistry ; 15(33): 8275-82, 2009 Aug 17.
Artigo em Inglês | MEDLINE | ID: mdl-19609993

RESUMO

A series of novel asymmetrical fused compounds containing the backbone of fluorene[2,3-b]benzo[d]thiophene (FBT) were effectively synthesized and fully characterized. Single-crystal X-ray studies demonstrated that the length of the substituent side chains greatly affects the solid-state packing of the obtained fused compounds. DFT, photophysical, and electrochemical studies all showed that the FBTs have large band gaps, low-lying HOMO energy levels, and therefore good stability toward oxidation. Moreover, the substituents strongly influence the fluorescence properties of the resulting FBT derivatives. The di-n-hexyl compound exhibits intense fluorescence in solution with the highest quantum yield of up to 91 %. Solution-processed green phosphorescent organic light-emitting diodes with the di-n-butyl derivative as the host material exhibited a maximum brightness of 14,185 cd m(-2) and a luminescence efficiency of 12 cd A(-1).

11.
J Org Chem ; 74(19): 7322-7, 2009 Oct 02.
Artigo em Inglês | MEDLINE | ID: mdl-19711948

RESUMO

Two asymmetrically substituted dicyanovinyl heterotetracenes are synthesized and characterized. Single-crystal X-ray diffractions indicate both intermolecular hydrogen bonds and pi-stacking existing in the solid-state structures. The solvatochromic behaviors of the two heterotetracenes were investigated in a variety of solvents. Both experimental and computational results suggest that the two heterotetracenes have low-lying lowest unoccupied molecular orbitals and thus may be potential n-type or bipolar organic semiconductors for organic electronics.

12.
Org Lett ; 21(2): 439-443, 2019 01 18.
Artigo em Inglês | MEDLINE | ID: mdl-30589266

RESUMO

A pair of chiral binaphthyl enantiomers ( S-/ R-6) incorporating a tetraphenylethene (TPE) moiety as an aggregation-induced emission (AIE) active group exhibits bright yellow circularly polarized electroluminescence (CP-EL) emission with a remarkable gEL value, low turn-on voltage, and high brightness in the nondoped CP organic light emitting diodes (CP-OLEDs). This work provides a new strategy to develop doping-free CP-OLED materials.

13.
Dalton Trans ; 48(43): 16289-16297, 2019 Nov 21.
Artigo em Inglês | MEDLINE | ID: mdl-31621733

RESUMO

A series of charge-neutral cyclometalated iridium(iii) complexes (1-3 and 5-7) containing triptycene-substituted ligands (tbt and tpbi) and two parent complexes (4 and 8) were synthesized and characterized. The crystal structures indicated that π-π stacking interactions existed in ligand tbtH, but not in complex 6. However, a large intramolecular repulsion was found in complex 6. These triptycene-based complexes exhibited good thermal stability, which was higher compared with that of the parent complexes. These complexes showed green to yellow emission with peaks that ranged from 503 to 563 nm. The introduction of the rigid non-conjugate triptycene skeleton caused a slight emission red shift (<25 nm), but a significant increase in the PLQYs (>47%) was observed. The electroluminescent devices employing 2 and 6 as phosphors displayed impressive performance improvements and low efficiency roll-off because of the higher PLQYs and HOMO levels of these triptycene-based complexes. The maximum current and external quantum efficiencies of the devices based on complexes 2 and 6 were 41.7 cd A-1, 11.9% and 41.2 cd A-1, 12.6%, respectively, which were about 31% higher than that of the devices based on the parent complexes 4 and 8. This work provides a novel approach to develop highly efficient phosphors with a triptycene skeleton.

14.
ACS Appl Mater Interfaces ; 7(45): 25129-38, 2015 Nov 18.
Artigo em Inglês | MEDLINE | ID: mdl-26502064

RESUMO

Three solution-processable exciplex-type host materials were successfully designed and characterized by equal molar blending hole transporting molecules with a newly synthesized electron transporting material, which possesses high thermal stability and good film-forming ability through a spin-coating technique. The excited-state dynamics and the structure-property relationships were systematically investigated. By gradually deepening the highest occupied molecular orbital (HOMO) level of electron-donating components, the triplet energy of exciplex hosts were increased from 2.64 to 3.10 eV. Low temperature phosphorescence spectra demonstrated that the excessively high triplet energy of exciplex would induce a serious energy leakage from the complex state to the constituting molecule. Furthermore, the low energy electromer state, which only exists under the electroexcitation, was found as another possible channel for energy loss in exciplex-based phosphorescent organic light-emitting diodes (OLEDs). In particular, as quenching of the exciplex-state and the triplet exciton were largely eliminated, solution-processed blue phosphorescence OLEDs using the exciplex-type host achieved an extremely low turn-on voltage of 2.7 eV and record-high power efficiency of 22.5 lm W(-1), which were among the highest values in the devices with identical structure.

15.
Org Lett ; 17(6): 1413-6, 2015 Mar 20.
Artigo em Inglês | MEDLINE | ID: mdl-25723625

RESUMO

A novel bipolar oligomer (TPA-PO)3 was prepared as a host material for efficient blue phosphorescent organic light-emitting diodes (OLEDs). Through the C-9s of the fluorene units, three triphenylamine units attached to diphenylphosphine oxide are connected in series to form a macrocyclic structure. The solution-processed phosphorescent device based on FIrpic and (TPA-PO)3 achieved a maximum current efficiency of 19.4 cd A(-1) and a maximum luminance of 11,500 cd m(-2) with a relatively low efficiency roll-off.

16.
ACS Appl Mater Interfaces ; 7(18): 9445-52, 2015 May 13.
Artigo em Inglês | MEDLINE | ID: mdl-25895904

RESUMO

Three bipolar hosts, namely TPA-DAF, TPA-DAF2, and TPA-DAF3, comprising an electron-donating triphenylamine (TPA) group and electron-accepting 4,5-diazafluorene (DAF) units are investigated for phosphorescent organic light-emitting diodes (PhOLEDs). Given the nonplanar structure of the sp(3)-hybridized C9 atom in DAF unit, these molecules have a highly nonplanar configuration, good film-forming property, and high triplet energy (ET) of 2.88-2.89 eV. Among them, TPA-DAF shows more balanced carrier injecting/transporting ability, suitable highest occupied molecular orbital (MO) energy level and higher current density, and therefore TPA-DAF-based devices exhibit the best performances, having an extremely slight efficiency roll-off with current efficiency of 20.0 cd/A at 973 cd/m(2), 19.5 cd/A at 5586 cd/m(2), and 17.6 cd/A at 9310 cd/m(2) for blue PhOLEDs; 23.5 cd/A at 1059 cd/m(2) and 15.3 cd/A at 8850 cd/m(2) for green PhOLEDs; and 12.2 cd/A at 1526 cd/m(2), 10.5 cd/A at 5995 cd/m(2), and 9.2 cd/A at 8882 cd/m(2) for red PhOLEDs, respectively. The results also provide a direct proof for the influence of charge balance on the device performance.

17.
Chem Asian J ; 8(2): 444-9, 2013 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-23161863

RESUMO

Excimers are generally considered as detrimental to OLEDs. For pyrene-based chromophores, however, this is not always true. In this contribution, two new methylated tetraphenylpyrenes, 1,3,6,8-tetra-o-tolylpyrene (TTPy) and 1,3,6,8-tetrakis(3,5-dimethylphenyl)pyrene (TDMPPy), were synthesized through Suzuki coupling reactions. TDMPPy absorbs and emits light at longer wavelengths than TTPy due to its more planar conformation and thus better conjugation. TDMPPy is prone to excimer formation, thus leading to a strong bathochromic shift (84 nm) in the photoluminescence spectrum of its film. TDMPPy exhibits efficient electroluminescence originating from pyrene excimers, affording a maximum luminance of 26,670 cd m(-2) and a current efficiency as high as 10.8 cd A(-1) in a non-doped OLED (ITO/PEDOT:PSS (50 nm)/NPB (30 nm)/TDMPPy (30 nm)/TPBI (40 nm)/Ca:Ag).

18.
J Phys Chem B ; 114(28): 9101-8, 2010 Jul 22.
Artigo em Inglês | MEDLINE | ID: mdl-20590166

RESUMO

In this article, four "A(3)+B(2)+C(2)"-type hyperbranched conjugated polymers (P1-P4) containing hexaphenylbenzene as the core were synthesized successfully for the first time with high yields through one-pot Suzuki polymerization reaction. The copolymerization percent of 1,3,4-oxadiazole units was adjusted to investigate the effect of polymer composition on the physical, optical, and EL properties. All polymers were well-characterized and exhibited good solubility, film-forming ability, and thermal stability. Both the solution and the films of these hyperbranched polymers emitted pure and stable deep-blue light emission, and their PL spectra did not change after annealing at 150 degrees C for 0.5 h in air, indicating that the hyperbranched structure, coupled to the introduced hexaphenylbenzene moieties, effectively suppressed the formation of aggregation excimer and keto defects. Two-layer PLED devices were fabricated to investigate the electroluminescence properties of these hyperbranched polymers, and P3 demonstrated a maximum luminance efficiency of 0.72 cd/A and a maximum brightness of 549 cd/m(2) at 16.5 V.

19.
Chem Commun (Camb) ; 46(45): 8573-5, 2010 Dec 07.
Artigo em Inglês | MEDLINE | ID: mdl-20976335

RESUMO

A fused-seven-ring anthracene derivative with two sulfur bridges, benzobisthioxanthene (BTA), was synthesized, facilely. OLEDs employing BTA as the emitter exhibited bright (maximum 40,752 cd m(-2)) and efficient red emission (CIE, x = 0.64, y = 0.36) with a luminous efficiency of 4.4 cd A(-1).

20.
Adv Mater ; 22(37): 4167-71, 2010 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-20540106

RESUMO

Blue light: Incorporation of two fluorenyl rings into a phenyl group at the C9 position of fluorene builds a bulky and rigidly tetrahedral framework, which is functionalized by two carbazole groups. This molecule possesses excellent thermal and morphological stability, miscibility to the phosphorescent dopant, and high triplet energy, leading to narrow blue phosphorescent emission.


Assuntos
Carbazóis/química , Polímeros/química , Soluções/química , Varredura Diferencial de Calorimetria , Fluorenos/química , Substâncias Luminescentes/química , Microscopia de Força Atômica
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