460347-59-5

Usage

Preparation

9-Bromo-10-phenylanthracene (5.8g, 17.4mmol), bis(pinacolato)diboron(6.63 g, 26.1 mmol), Pd(dppf)Cl2 (710 mg, 0.87 mmol), and KOAc (10.23 g, 104.4 mmol) were mixed in a 250mL flask containing 1,4-dioxane (60 mL). The reaction mixture was refluxed for 24h under nitrogen. After it was cooled to room temperature, a dilute hydrochloric acid solution quenched. The mixture was extracted with CH2Cl2 and dried over anhydrous MgSO4. The crude product was concentrated by rotary evaporation and further purified by silica gel column chromatography (CH2Cl2 / petroleum ether (1:1,v/v)) to afford a light yellow powder (4.0 g, 60.4 %). 1H NMR (500 MHz, CDCl3) δ 8.46 (d, J = 8.7 Hz, 2H), 7.65 (d, J = 8.8 Hz, 2H), 7.57 (dq, J = 14.2, 7.0 Hz, 3H), 7.51 – 7.46 (m, 2H), 7.41 (d, J = 7.0 Hz, 2H), 7.34 (dd, J = 8.1, 7.1 Hz, 2H), 1.63 (s, 12H). EI-MS (m/z): Calculated for C26H25BO2: 380.29. Found [M+]: 379.92. Synthesis of 4,4,5,5-Tetramethyl-2-(10-phenylanthracen-9-yl)-1,3,2-dioxaborolane

Upstream product

• 523-27-3 9,10-Dibromoanthracene 
• 108-86-1 bromobenzene 
• 602-55-1 9-phenylanthracene 
• 1564-64-3 9-Bromoanthracene 
• 100622-34-2 anthracene-9-boronic acid 
• 23674-20-6 9-bromo-10-phenylanthracene 
• 73183-34-3 bis(pinacol)diborane 
• 98-80-6 phenylboronic acid 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 1198211-88-9 1,3-bis(9-(4-(10-phenylanthracen-9-yl)phenyl)-9H-fluoren-9-yl)benzene 
• 1263216-61-0 3,5-bis(5H-pyrido[4,3-b]indol-5-yl)-(10-phenylanthracen-9-yl)benzene 
• 1263216-69-8 5-{6-[4-(10-phenylanthracen-9-yl)phenyl]pyridin-2-yl}-5H-pyrido[4,3-b]indole 
• 1263216-67-6 5-{6-[3-(10-phenylanthracen-9-yl)phenyl]pyridin-2-yl}-5H-pyrido[4,3-b]indole 
• 1263216-38-1 5-[6-(10-phenylanthracen-9-yl)naphthalen-2-yl]-5H-pyrido[4,3-b]indole 
• 1263216-25-6 5-[3-methyl-4-(10-phenylanthracen-9-yl)phenyl]-5H-pyrido[4,3-b]indole 
• 1263216-43-8 5-[4'-(10-phenylanthracen-9-yl)biphenyl-4-yl]-5H-pyrido[4,3-b]indole 
• 1263216-52-9 5-[4-(10-phenylanthracen-9-yl)phenyl]-5H-pyrido[4,3-b]indole 
• 1263216-71-2 5-[3-(10-phenylanthracen-9-yl)phenyl]-5H-pyrido[4,3-b]indole 
• 1007375-69-0 6'-(10-phenylanthracen-9-yl)-6-(5H-pyrido[4,3-b]indol-5-yl)-[2,2']bipyridine 
• 1112955-34-6 9-(2-methoxy-1,1,3,3-tetramethylisoindolin-5-yl)-10-phenylanthracene 
• 1112955-33-5 10-phenyl-9-(1,1,3,3-tetramethylisoindolin-2-yloxyl-5-yl)anthracene 

Relevant academic research and scientific papers

ORGANIC LIGHT-EMITTING DEVICE

An organic light-emitting device including: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer, wherein the emission layer includes a polycyclic compound represented by Formula 1 and a host, and wherein an amount of the polycyclic compound is less than an amount of the host in the emission layer, wherein Formula 1 is as provided herein.

Diphenylanthracene Dimers for Triplet-Triplet Annihilation Photon Upconversion: Mechanistic Insights for Intramolecular Pathways and the Importance of Molecular Geometry

Novel approaches to modify the spectral output of the sun have seen a surge in interest recently, with triplet-triplet annihilation driven photon upconversion (TTA-UC) gaining widespread recognition due to its ability to function under low-intensity, noncoherent light. Herein, four diphenylanthracene (DPA) dimers are investigated to explore how the structure of these dimers affects upconversion efficiency. Also, the mechanism responsible for intramolecular upconversion is elucidated. In particular, two models are compared using steady-state and time-resolved simulations of the TTA-UC emission intensities and kinetics. All dimers perform TTA-UC efficiently in the presence of the sensitizer platinum octaethylporphyrin. The meta-coupled dimer 1,3-DPA2 performs best yielding a 21.2% upconversion quantum yield (out of a 50% maximum), which is close to that of the reference monomer DPA (24.0%). Its superior performance compared to the other dimers is primarily ascribed to the longer triplet lifetime of this dimer (4.7 ms), thus reinforcing the importance of this parameter. Comparisons between simulations and experiments reveal that the double-sensitization mechanism is part of the mechanism of intramolecular upconversion and that this additional pathway could be of great significance under specific conditions. The results from this study can thus act as a guide not only in terms of annihilator design but also for the design of future solid-state systems where intramolecular exciton migration is anticipated to play a major role.

Compound, organic luminescent material and organic electroluminescent device

The invention provides a compound as shown in a general formula (I), which has a mother structure of sym-triphenyl substituted anthracene, is high in bond energy among atoms, has good thermal stability, is beneficial to solid-state accumulation among molecules, is large in bandwidth, has a light-emitting region in a blue light region, is high in light-emitting intensity, and has a proper energy level with adjacent levels. And injection and migration of excitons are facilitated. When the compound is used as a blue light host material in a luminescent layer, the driving voltage of an organic electroluminescent device can be effectively reduced, the luminous efficiency is improved, and the service life is prolonged. The invention also provides an organic electroluminescent device and a display device containing the compound of the general formula (I).

ANTHRACENE DERIVATIVES CONTAINING BENZIMIDAZOLE OR BORATE AND ORGANOELECTROLUMINESCENT DEVICE INCLUDING THE SAME

An organic light-emitting diode comprises a first electrode layer, a second electrode layer, and an organic luminescent unit disposed between the first electrode layer and the second electrode layer. The organic luminescent unit has an organic electroluminescent material containing anthracene group as shown in General Formula (1): wherein A is selected from the group consisting of General Formula (2), General Formula (3) and General Formula (4): wherein B is selected from the group consisting of General Formula (5), General Formula (6) and General Formula (7): B is General Formula (5) when A is selected from the group consisting of General Formula (2) and General Formula (3); B is selected from the group consisting of General Formula (6) and General Formula (7) when A is General Formula (4); and wherein R1 to R43 are independently selected from the group consisting of hydrogen atom, fluorine atom, cyano group, alkyl group, cycloalkyl group, alkoxy group, haloalkyl group, thioalkyl group, silyl group and alkenyl group.

Organic blue fluorescent material and preparation method and application thereof

The invention relates to an organic blue fluorescent material and a preparation method and application thereof. The material adopts a delta bond as a bridge chain to connect two anthracene molecule luminescence units and regulate the conjugation state of organic molecules; meanwhile, a steric hindrance group is introduced onto the delta bond to inhibit a pi-pi accumulation effect among the organicmolecules, and correspondingly the organic blue fluorescent material is prepared and has high thermal stability and high luminous quantum efficiency. The specific preparation method and application mainly include the steps of adopting 9-benzanthracene-10 borate and 4,4'-dibromo diphenyl bis-substituted methane for conducting a Suzuki coupling reaction to prepare the organic blue fluorescent material. The material is adopted as a luminous layer and achieves a non-doped deep blue OLED device with high performance.

Organic blue fluorescent material based on dianthracene as well as preparation method and application of organic blue fluorescent material

The invention relates to an organic blue fluorescent material based on dianthracene as well as a preparation method and application of the organic blue fluorescent material. The molecular design of the material takes benzene as a central pi conjugated bridge chain, two anthracene luminescent units are connected to a meta-position of the central pi conjugated bridge chain, and the pi conjugated form of organic material molecules and pi-pi stack among molecules are regulated, so that the deep blue light emission in OLED device application is realized; meanwhile, a group with electron donating property or a group with electron withdrawing property is introduced to the central pi conjugated bridge chain, so as to further inhibit pi-pi stack among the material molecules, realize high laminationquantum efficiency of the material molecules and prepare the organic blue fluorescent material, and the material has good thermal stability and high lamination quantum efficiency.

Semiconducting Material Comprising a Phosphine Oxide Matrix and Metal Salt

The present invention is directed to a semiconducting material comprising: i) a compound according to formula (I) wherein R1, R2 and R3 are independently selected from C1-C30-alkyl, C3-C30 cycloalkyl, C2-C30-heteroalkyl, C6-C30-aryl, C2-C30-heteroaryl, C1-C30-alkoxy, C3-C30-cycloalkyloxy, C6-C30 aryloxy, and from structural unit having general formula E-A-, wherein—A is a C6-C30 phenylene spacer unit, and—E is an electron transporting unit that is selected from C10-C60 aryl and C6-C60 heteroaryl comprising up to 6 heteroatoms independently selected from O, S, P, Si and B and that comprises a conjugated system of at least 10 delocalized electrons, and—at least one group selected from R1, R2 and R3 has the general formula E-A-; and ii) at least one complex of a monovalent metal having formula (II) wherein—M+ is a positive metal ion bearing a single elementary charge, and each of A1, A2, A3 and A4 is independently selected from H, substituted or unsubstituted C6-C20 aryl and substituted or unsubstituted C2-C20 heteroaryl, wherein a heteroaryl ring of at least 5 ring-forming atoms of the substituted or unsubstituted C2-C20 heteroaryl comprises at least one hetero atom selected from O, S and N.

Organic blue fluorescent materials as well as preparation method and application thereof

The present invention relates to organic blue fluorescent materials as well as a preparation method and application thereof. The materials have a structural formula represented by a formula (I) shownin the description, wherein R includes a group having an electron-donating property or a group having an electron-withdrawing property; and the preparation method mainly includes the following preparation step: 9-benzoquinone-10 borate and 1,4-dibromo-2,5-disubstituted benzene are subjected to a Suzuki coupling reaction to prepare the organic blue fluorescent material. The method provided by the present invention uses benzene as a pi conjugated bridge chain to connect two anthracene molecule luminescent units, and introduces a sterically-hindered group at p-position of a benzene ring of the center pi conjugated bridge chain to eliminate pi-pi stacking interaction among molecules through precise design of material molecules; and the prepared organic blue fluorescent material has good thermal stability and high luminescence quantum efficiency.

An electroluminescent compound and an electroluminescent device comprising the same

The present invention relates to an organic light emitting compound adopted to an organic electroluminescent device. The organic light emitting compound is represented by chemical formula 1. When adopting the organic light emitting compound as a dopant compound or a hole transfer compound in a luminous layer, the organic electroluminescent device has excellent light emitting characteristics such as operating voltage, brightness, long lifespan, and the like.COPYRIGHT KIPO 2016

Asymmetrically twisted anthracene derivatives as highly efficient deep-blue emitters for organic light-emitting diodes

Deep-blue emission is particularly important for applications of organic light-emitting diodes (OLEDs) in full colour flat-panel displays and solid-state lighting resources. Two asymmetrically twisted anthracene derivatives, 4,5-diphenyl-1,2-bis(4-(10-phenylanthracen-9-yl)phenyl)-1H-imidazole (DPA-PIM) and 1,2-bis(4-(10-phenylanthracen-9-yl)phenyl)-1H-phen-anthro[9,10-d]imidazole (DPA-PPI), for deep-blue OLEDs have been designed and synthesized. The asymmetrically twisted conformations between anthracene and imidazole units in compounds efficiently interrupt molecular π-conjugation and inhibit π-π intermolecular interactions, resulting in high thermal stability and efficient deep-blue emission. The two anthracene derivatives in non-doped OLEDs exhibited blue emission. In particular, the non-doped device based on DPA-PIM achieved an external quantum efficiency (EQE) of 6.5% with CIE coordinates of (0.15, 0.08). In addition, the two emitters in doped devices achieved high EQEs of over 5.0% and much purer blue emission with CIE coordinates of (0.15, 0.06) for DPA-PPI and (0.15, 0.05) for DPA-PIM, which nearly match the CIE coordinates of the European Broadcasting Union (EBU) blue standard of (0.15, 0.06).