New Blue-Light Emitting Materials in White OLED Based on Solution and Vacuum Methods

New host material of 2-tert-butyl-9,10-bis(3′′,5′′-diphenylbiphenyl-4′-yl)anthracene [T-TAT] substituted t-butyl group was investigated in solution process WOLED device compared with 9,10-bis (3′′,5′′-diphenylbiphenyl-4’-yl) anthracene [TAT]. A two-color WOLED of a co-host system using solution process method was demonstrated. The device configuration was ITO / PEDOT:PSS (40 nm) / emitting layer (50 nm) / TPBi (20 nm) / LiF (1 nm) / Al. The emitting layer consisted of TAT or T-TAT, NPB, DPAVBi (blue dopant), and rubrene (yellow dopant). NPB was used to help hole carrier transport as well as blue host role. The device using the T-TAT compound as a co-host showed a luminance efficiency of 2.73 cd/A, which is 77% higher than TAT device of 1.54 cd/A at 20 mA/cm².     

Synthesis and Properties of New Imidazole Derivatives Including Various Chromophore for OLEDs

Abstract

Two new blue compounds were successfully synthesized by introducing phenanthroimidazole group as a side group into pyrene, a chromophore with good luminous efficiency: 1-(4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-2-(pyren-1-yl)-1H-phenanthro[9,10-d]imidazole (NA-PPI) and 1-(4'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-yl)-2-(pyren-1-yl)-1H-phenanthro[9,10-d]imidazole (CP-PPI). The optical and electroluminescence properties of newly synthesized materials were measured. Both materials emit blue or sky-blue photoluminescence in the film state and have a high PLQY value of over 80% in solution state. The synthesized materials were applied as EML in non-doped devices, and high efficiency of 3.51?cd/A and EQE of 2.39% in CP-PPI device were achieved.     

Blue Emission Color Control by Co-Deposition Method in Organic Light Emitting Diodes

9,10-bis(3′′,5′′-diphenylbiphenyl-4′-yl)anthracene (TAT) and 4-(1′-(3′,5′-diphenylbiphenyl-4-yl)anthracen-9-yl)-N,N-diphenylaniline (TATa) which have electroluminescence (EL) maximum values of 441nm and 469 nm were used blue emitting materials in organic light emitting diodes (OLED). OLED devices were fabricated and characterized by co-deposited emitters of TAT and TATa with different ratios. C.I.E. values of the devices using TAT and TATa were changed from (0.148, 0.081) to (0.139, 0.194).     

The nature of the electrical conduction and light emitting efficiency in organic semiconductors layers: The case of [m-MTDATA] – [NPB] – Alq3 OLED

In this work, a detailed study on the influence of different layers in an Alq3 [aluminium-tris(8-hydroxyquinoline)] based OLED is made. Two hole transport layers have been used: m-MTDATA [4,4′,4″-tris (3-methyl-phenylphenylamino) triphenylamine] and NPB [N,N′-bis-(1-naphthyl)-N,N′-diphenyl-1,1′-biphenyl-4,4″-diamine]. It is found that the efficiency (at 520 nm) can increase up to one order of magnitude when we consider a three layer device instead of a conventional two layer. The driving voltage decreases in the three layer device, but the output electroluminescence spectra (in green spectral region) tend to be broaden towards high energies. The current–voltage behavior follows a space charge limited current behavior. The influence of the traps states and/or a Poole-Frenkel like field mobility dependence is discussed. The electroluminescence data fit to a large green band (one main green band and a small orange band) and for the three layer device a small blue band appears. Finally, a model involving an individual layer contribution with the corresponding trap levels is proposed.     

Synthesis and properties of new fluorene-containing copolymer via the catalytic dehydrocoupling reaction of 9,9-dipropargyl fluorene and 4,4′-diphenyl-2,6-dibromo-dithieno-[3,2-b:2′,3′-d]silole

ABSTRACT

New fluorene-containing copolymer was prepared via the catalytic dehydrocoupling reaction of 9,9-dipropargylfluorene and 4,4′-diphenyl-2,6-dibromo-dithieno-[3,2-b:2′,3′-d]silole in 44% yield. The resulting polymer was completely soluble in common organic solvents. The thermal behaviors and optical properties of the resulting polymer were measured and discussed. The chemical structure of polymer was characterized by NMR, IR, and UV-visible spectroscopies. The polymer showed characteristic wide UV-visible absorption band and blue PL maximum value at 440 nm, which is corresponding photon energy of 2.82 eV. The quantum yield (6.44%) of poly(DPF-DTS) was found to be 5 times higher than that of poly(DPF-bithiophene)).     

Highly Luminescent Red Phosphorescent OLED with Interfacial Layers for Hole Transport and Electron Injection

Four kinds of red phosphorescent organic light-emitting devices were fabricated and compared to investigate the effect of interfacial layers for hole transport and electron injection. 1 nm-thick LiF in the device A and C and 1 nm-thick Cs₂CO₃ in the device B and D were deposited as an electron injection layer between the anode and the electron transport layer, and 5 nm-thick layer of dipyrazion[2,3-f:2′,2′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile[HATCN] was inserted as a hole transport interfacial layer between the hole injection layer and the hole transport layer only in the device C and D. Under a luminance of 1000 cd/m², the power efficiencies were 7.6 lm/W and 8.5 lm/W in the device A and B, and 8.6 lm/W and 13.4 lm/W in the device C and D. The quantum efficiency of the device D was 15.8% under 1000 cd/m² which was somewhat lower than those of the device A and C, but a little higher than that of the device B. The luminance of the device D was much higher than those of the other devices at a given votage. The luminance of the device D at 7 V was 23,710 cd/m², which was 13.0, 3.4, and 4.0 times higher than those of the device A, B, and C at the same voltage, respectively.     

Organic Light-Emitting Diodes based on Benzo[q]quinoline Derivatives

Abstract

In this study, we synthesized two emitting materials based on benzo[q]quinoline derivatives. OLED devices using these materials were facricated in the following sequence;ITO(180nm)/4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine(2-TNATA)(30nm)/N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine(NPB)(20nm)/Emitting materials(30nm)/4,7-diphenyl-1,10-phenanthroline (Bphen)(30nm)/Liq(2nm)/Al(100nm). Particularly, a device using 2,4-di(naphtalene-1-yl)benzo[q]quinoline as an emitter exhibited the efficient emission with a luminous efficiency, a power efficiency, and exteranl quantum efficiency of, and the CIE coordinates of 2.91cd/A, 0.99lm/W, 0.90% at 20mA/cm², and (0.33, 0.55) at 1000cd/m², respectively. Interestingly, emissions from electromers and electroplexes were shown to be crucial role in electroluminescences from benzo[q]quinoline derivatives     

Synthesis,Characterization and Mesomorphic Properties of New Rod-like Thiophene Based Liquid Crystals

Two new mesogenic homologous series of Schiff base esters, 2-[4-(4′-n-Alkoxy benzoyloxy) benzylidenamino] 3-cyno thiophine (Series-A) and Schiff base cinnamates, 2-[4-(4′-n-alkoxy cinnamoyloxy) benzylidenamino] 3-cyano thiophene (Series-B), comprising a thiophene moiety were synthesized. Structural elucidation was carried out using elemental analysis and spectroscopic techniques such as FT-IR, ¹H-NMR and ¹³C-NMR, and mass spectrometry. The mesomorphic properties and thermal stabilities of the title compounds were studied by using differential scanning calorimetry and optical polarizing microscopy. All the derivatives are mesomorphic in nature showing the nematic phase, and the higher members of Series-A show a smectic C phase whereas Series-B exhibits only the nematic mesophase. The mesomorphic properties of the present series are compared with other structurally related compounds.     

Blue electroluminescent materials based on indeno[1,2-a]arene derivatives for Organic Light-Emitting Diodes

Abstract

In this study, as a continuous effort for searching efficient blue-emitting materials, we designed and synthesized materials based on indeno[1,2-a]arene. OLED devices using these materials were fabricated in the following sequence; ITO (180?nm)/N,N'-diphenyl-N,N'-(2-napthyl)-(1,1'-phenyl)-4,4'-diamine (NPB) (50?nm)/emitting materials (30?nm)/4,7-diphenyl-1,10-phenanthroline (Bphen) (30?nm)/Liq/Al (2/100?nm). Particularly, a device using 7,7-dimethyl-7H-indeno[1,2-a]pyrene as emitter showed maximum values of luminous efficiency, power efficiency, and external quantum efficiency of 1.10?cd/A, 0.49?lm/W, 1.47% at 20?mA/cm², respectively with CIE (x,y) coordinates of (0.15, 0.08) at 6.0V.     

一种多吡啶铜(Ⅰ)配合物的合成、结构及DNA光裂解研究

本文以1-甲基-4′-对苯甲基-2,2′,6′,2″-三联吡啶六氟磷酸盐(L)为配体合成了一例新的铜配合物[CuL₂](PF₆)₃·H₂O(配合物1)。通过X射线单晶衍射技术、热重分析和X射线光电子能谱(XPS)对所合成的配合物进行了结构的表征和化学价的分析。单晶衍射分析结果表明,该配合物属于单斜晶系,P2_1/c空间群,晶胞参数为a=1.273 15(10) nm、b=1.902 01(13) nm、c=2.109 55(17) nm、β=101.269(2)°、V=5.009 9(7) nm³。XPS分析结果表明,配合物中的铜离子是以＋1价的形式存在。热重分析表明,该配合物具有较高的热稳定性。琼脂糖凝胶电泳实验表明,该配合物在光照条件下能有效使DNA裂解,表明该配合物具有明显的潜在生物活性。     

Crystal Structure Analysis of 1′,2′,3′,4′‐tetrahydro‐1,3‐diphenyl‐4‐chlorospiro[2‐pyrazoline‐5,2‐napthalen]1′one

The crystal structure of the title compound “1′,2′,3′,4′‐tetrahydro‐1,3‐diphenyl‐4‐chlorospiro[2‐pyrazoline‐5,2‐napthalen] 1′one” has been determined. The structure consists of a pyrazoline ring, three aromatic rings and a tetralone moiety. All the aromatic rings are planar while the cyclohexonone ring of the tetralone moiety is in the distorted sofa conformation. The molecular packing is stabilized by C‐H…O and C‐H…π type inter molecular interactions.     

新型镉(Ⅱ)配合物荧光探针的合成及性能

以8-氨基喹啉、1,5-萘二磺酸根为配体,NaN3为pH调节剂,与Cd(NO3)2通过水热反应,合成了一个新的一维链状镉配合物:[Cd(8-aql)2(1,5-nd)]2·H2O(1)(8-aql=8-氨基喹啉,1,5-nd=1,5-萘二磺酸根),并对其进行了元素分析、红外光谱和X-射线单晶衍射表征.配合物1属于单斜晶...     

Synthesis and Characterization of Monomeric and Dimeric Structures of Calix[4]arenes Containing Amidoferrocene

Abstract The reaction of 1,1′-bis(chlorocarbonyl)ferrocene with bis-aminobenzylcalix[4]arene gave amidoferrocene calix[4]arene monomer 1. Compound 1 crystallized in the monoclinic system P21/c with a = 11.196(6) ?, b = 14.971(11) ?, c = 32.007(2) ?, β = 96.413(4)° and V = 5330.9(6) ?³. X-ray diffraction analyses of 1 showed that the calix[4]arene scaffold was in cone conformation in which the intramolecular hydrogen bonding were formed through OH groups at the lower rim to stabilize the structure. Moreover, the intramolecular hydrogen bond between the amide groups of the amidoferrocene unit also presented in the crystal structure. On the other hand, the condensation of 1,1′-bis(chlorocarbonyl)ferrocene with p-tert-bis-aminobenzylcalix[4]arene resulted in the monomeric 2 and [2 + 2] dimeric compounds 3. ¹H-NMR studies signified that the calix[4]arene building block in compounds 2 and 3 adopted the cone conformation. Index Abstract Synthesis and Characterization of Monomeric and Dimeric Structures of Calix[4]arenes Containing Amidoferrocene Chomchai Suksai*, Pannee Leeladee, Colin Jennings, Thawatchai Tuntulani*, Palangpon Kongsaeree The condensation of 1,1′-bis(chlorocarbonyl)ferrocene with p-tert-bis-aminobenzylcalix[4]arene resulted in the monomeric and [2 + 2] dimeric compounds.      

吡啶鎓盐配体构筑的多钼酸基配合物的合成、结构及光催化性能

本文在水热条件下合成了一例同多钼酸阴离子[δ-Mo₈O₂₆]^4-基配合物[Co(bipbc)(δ-Mo₈O₂₆)_0.5(H₂O)₃] (bipbc=4,4-双[(4-羧基吡啶)甲基]联苯),其为一维链状结构,包含环型双核钴配合物[Co₂(bipbc)₂]⁴⁺和[δ-Mo₈O₂₆]^4-簇。该配合物结晶于单斜晶系,P2₁/n空间群,a=1.147 9(8) nm,b=1.440 9(11) nm,c=2.082 9(16) nm,β=93.469(2)°,V=3.438 8(4) nm³,Z=4,M_r=1 129.18,F(000)=2 204,μ=1.979 mm^-1,D_c=2.181 mg·m^-3,S=1.019,R₁=0.056 2,wR₂=0.137 7。光催化性质研究表明,在可见光、近红外光和全光谱的光照条件下,标题配合物对龙胆紫(GV)和亚甲基蓝(MB)的降解,表现出一定的光催化活性。     

Synthesis and Crystal Structure of Two Diflunisal Carboxamides

Graphical abstract  

The title compounds, 2′,4′-difluoro-4-[(4-methylbenzoyl)oxy]-N-[4-nitro-3-(trifluoromethyl)phenyl]-[1,1′-biphenyl]-3-carboxamide 2a and 2′,4′-difluoro-4-[(4-chlorobenzoyl)oxy]-N-[4-nitro-3-(trifluoromethyl) phenyl]-[1,1′-biphenyl]-3-carboxamide 2b, synthesized from diflunisal, a registered anti-inflammatory drug, via amidation of carboxlic acid and esterification of phenolic hydroxy group, were confirmed by single- crystal X-ray diffraction showing their packing are stabilized by intermolecular hydrogen bonds      

三维孔道结构钒磷酸盐[H3N(CH2)3NH3]2[H3N(CH2)3NH2][H2N(CH2)3NH2]-[V(H2O)2(VO)8(OH)4(PO4)4(HPO4)4]·4H2O的水热合成和结构表征

以1,3-丙二胺为模板,水热合成了三维孔道结构钒磷酸盐[H3N(CH2)3NH3]2[H3N(CH2)3NH2][H2N(CH2)3NH2][V(H2O)2(VO)8(OH)4(PO4)4(HPO4)4]·4H2O(DAP-V9P8).用单晶X射线衍射、红外光谱和热重法对该化合物的晶体结构进行了表征.DAP-V9P8的无机骨架由[VO5]、[VO6]、[PO4]和[HPO4]通过共顶点连接而成.孔道中充填的丙二胺分子随所处结晶学位置不同,有三种完全不同的分子构象.其中,位于//b轴直径达1.82nm椭圆形孔道中心的丙二胺分子碳链呈独特的直线状分布.晶体学参数:a=1.4820(9)nm,b=1.0255(4)nm,c=1.8181(9)nm,β=90.391(8)°;P21/n(No.14);R1=0.0772,wR2=0.2004(I＞(2σI)).与等结构的其它化合物进行了系统的结构比较.     

Synthesis,spectral characterization,and single crystal structure studies of biologically relevant bis-indoline heterocyclic scaffold

The new biologically relevant compound, 5,5″-methoxy-1′-methyl-1H,1″H-[3,3′:3′,3″-terindol]-2′(1′H)-one was synthesized, in 89% yield, by the one-pot reaction between 5-methoxyindole and 1-methylisatin in the presence of a low-cost and environmentally benign commercially available sulfamic acid as an organocatalyst and have been characterized by elemental analyses, IR spectra, and single crystal X-ray analysis. The crystals are orthorhombic, sp. gr. Pbca, Z = 8. The structure is stabilized by N–H···O and C–H···O interactions.     

两例相同混合配体构筑的Pb(Ⅱ)/Ag(I)配位聚合物及其荧光性质

多齿配体2-咪唑乙酸(Hima)、4,4'-连吡啶分别与金属盐Pb(NO₃)₂和AgNO₃反应,得到[Pb₂(4,4'-bipy)(ima)(NO₃)₃]_n(1, 3D framework)和[Ag₄(4, 4'-bipy)₃(ima)₂(NO₃)₂(H₂O)₂]_n(2, 3D framework)两个配位聚合物。根据配位聚合物的结构特点,研究了这两个配位聚合物荧光性质等物理化学性能。配位聚合物1在最大激发波长(λ_ex=346 nm)激发下,荧光的最大发射波长为552 nm,配位聚合物2在最大激发波长(λ_ex=369 nm)激发下,荧光的最大发射波长为444 nm。这可能是由于金属和配体之间发生了电荷转移(LMCT)。     

X-ray diffraction investigation of trans-2,8-dihydroxy-2,8-diphenyl-4,4′,6,6′,10,10′, 12,12′-octamethylcyclohexasiloxane and trans-2,8-dihydroxy-2,4,4′,6,6′,8,10,10′, 12,12′-decamethyl-5-carbahexacyclosiloxane

The crystal structures of two organosilicon compounds are studied by X-ray diffraction. Crystals of trans-2,8-dihydroxy-2,8-diphenyl-4,4′,6,6′,10,10′,12,12′-octamethylcyclohexasiloxane, C₂₀H₃₆O₈Si₆, (I) are triclinic; at 110 K, a = 11.476(1) Å, b = 12.106(1) Å, c = 13.636(1) Å, α = 94.337(1)°, β = 112.669(1)°, γ = 112.216(1)°, space group $P\bar 1$ , Z = 2, and R = 0.057 for 5069 reflections with F > 4σ(F). Crystals of trans-2,8-dihydroxy-2,4,4′,6,6′,8,10,10′,12,12′-decamethyl-5-carbahexacyclosiloxane, C₁₁H₃₄O₇ Si₆, (II) are tetragonal; at 293 K, a = b = 15.487(3) Å, c = 11.364(3) Å, space group P4₂/n, Z = 4, and R = 0.055 for 955 reflections with F > 4σ (F). It is found that the structure of compound I, in which the substituents at the Si(1) atom differ in volume and inductive effect, contains two crystallographically independent molecules with different conformations of the hexasiloxane ring. In structure II, the oxygen atom and the methylene group are statistically disordered as a result of the location of the molecule at the center of symmetry. Although the SiCSi angle [122.1(1)°] differs noticeably from the tetrahedral angle, its value is characteristic of cyclohexasiloxanes and is not related to the disorder.     

一例混合配体构筑的钴(Ⅱ)一维配位聚合物的合成、晶体结构与磁性质

基于萘膦酸羧酸酯配体和氯化钴在水热条件下自组装得到配位聚合物[Co(5-pncee)(4,4′-bpy)(H₂O)₃(5-pnceeH₂)]·2H₂O(1)(5-pncee H₂=5-phosphono -naphthalene-1-carboxylic acid ethyl ester, 4,4′-bpy=4,4′-bipyridinyl)。采用单晶衍射(X-Ray)、元素分析(EA)、红外光谱(FT-IR)、粉末衍射(PXRD)、热重分析(TG-DTG)对配位聚合物进行晶体结构和热稳定性表征。晶体结构分析表明:该配位聚合物结晶于三斜晶系,P1空间群,a=0.824 06(6) nm,b=1.014 48(9) nm,c=1.151 44(8) nm。配位聚合物呈线性链状结构。相邻的链由中等强度的氢键连接,形成超分子层,层间被膦酸配体的有机基团所填充。通过研究配位聚合物1的磁性质,表明Co(II)离子存在自旋轨道耦合和/或Co(II)离子之间存在反铁磁相互作用。