KR20140081694A - Phenophosphazines compounds - Google Patents

Abstract

The present invention provides a composition comprising at least one compound selected from below compounds: A) (In chemical formula A, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are a hydrocarbon or a substituted hydrocarbon, respectively. Selectively, at least two R groups selected from R2, R3, R4, R5, R6, R7, R8, R9 and R10 are able to form at least one ring structure.); B) (In chemical formula B, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are a hydrocarbon or a substituted hydrocarbon, respectively. Selectively, at least two R groups selected from R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are able to form at least one ring structure.); and C) which is a combination thereof.

Description

PHENOPHOSPHAZINES COMPOUNDS < RTI ID = 0.0 >

The organic light emitting device OLED is a display device employing a film stack containing an organic aromatic compound as an electroluminescent layer. Such a compound is generally classified into an electroluminescent material and a charge transporting material. Some characteristics required for such electroluminescent compounds and charge transport compounds include high fluorescence quantum yields in the solid state, high mobility of electrons and holes, chemical stability during deposition in vacuum, and the ability to form stable films.

Common problems with OLEDs include fast aging / short lifetime, undesirably high operating voltage, or poor efficiency. The discovery of new materials for the electron transport layer (ETL) and the hole transport layer (HTL) of organic light emitting diodes (OLEDs) has been aimed at improving device performance and lifetime. In the case of the HTL layer, the state of the art uses triarylamine-based materials that satisfy many current emission and phosphorescent OLED designs. In phosphorescent OLED designs, device efficiency, lifetime, and luminance still remain issues for the mass production of blue phosphorescent OLEDs.

Therefore, there is a need for a hole transport layer having enhanced properties compared to current technologies. In addition, there is a need for hole transport materials that enable faster transport of charge to the emissive layer and long lasting and efficient devices. These requirements and the like are satisfied by the following invention.

The present invention provides compositions comprising at least one compound selected from the following compounds:

A)

Wherein R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9 and R 10 are each independently a hydrocarbon or a substituted hydrocarbon,

Wherein two or more R groups optionally selected from R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9 and R 10 may form one or more ring structures;

B)

(Wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are each independently a hydrocarbon or a substituted hydrocarbon,

Wherein two or more R groups optionally selected from R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9 and R 10 may form one or more ring structures; or

C) a combination of these.

A new class of molecules based on the central phenophosphine core has been discovered. Such molecules can be manipulated through the regulation of organic groups located on 1) the center or on the phenophosphazene core, and 2) the oxidation state of phosphorus centers. Computer modeling of these derivatives suggests that the charge transport layer of such compounds retains the higher HOMO and LUMO energy levels, while retaining higher triplet energies. Also, arylamine substitution at the R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ^9, and R ¹⁰ positions delineate the HOMO orbitals across the benzene ring on which these substituents are located . As a result, the excitons formed in OLED devices are well confined to the emissive layer, resulting in improved device brightness, lifetime, and efficiency.

As discussed above, the present invention provides compositions comprising at least one compound selected from the following compounds:

A)

Wherein R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9 and R 10 in the formula (A) are each independently hydrocarbons (including H), or substituted hydrocarbons,

Wherein two or more R groups optionally selected from R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9 and R 10 may form one or more ring structures;

B)

Wherein R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9 and R 10 are independently hydrocarbons (including H) or substituted hydrocarbons,

Wherein two or more R groups optionally selected from R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9 and R 10 may form one or more ring structures; or

C) a combination of these.

The compositions of the present invention may comprise a combination of two or more of the embodiments described herein.

Is used herein ^{R1 = R 1, R2 = R} 2, R3 = R 3 ....

In one embodiment, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 in formula A are each a hydrocarbon or substituted hydrocarbon,

R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9 and R 10 are each independently a hydrocarbon or a substituted hydrocarbon.

In one embodiment, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 in formula A are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, Lt; / RTI >

Wherein R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9 and R 10 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, / RTI >

In one embodiment, R2, R4, R5, R6, R7 and R9 in formula A are each hydrogen and R2, R4, R5, R6, R7 and R9 in formula B are each hydrogen.

In one embodiment, R3 and R8 in formula A are each independently alkyl, more preferably C1 to C8 alkyl, more preferably C1 to C4 alkyl, more preferably ethyl or methyl, and R3 and R8 in formula Are each independently alkyl, more preferably C1 to C8 alkyl, more preferably C1 to C4 alkyl, more preferably ethyl or methyl.

In one embodiment, at least one of R2, R3, R4, R5, R6, R7, R8, R9 and R10 in Formula A is an arylamine and R2, R3, R4, R5, R6, At least one of R < 9 > and R < 10 > is an arylamine.

In one embodiment, R1 in formula (A) comprises 6 or more carbon atoms, wherein R1 in formula (B) comprises 6 or more carbon atoms.

In one embodiment, R10 in formula A contains at least 6 carbon atoms, wherein R10 in formula B comprises at least 6 carbon atoms.

In one embodiment, the composition comprises a compound of formula (A) and a compound of formula (B).

In one embodiment, the at least one compound is selected from the following compounds, or combinations thereof.

,

,

,

,

,

,

In one embodiment, at least one compound is selected from formula (A).

In one embodiment, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 in formula (A) are each independently a hydrocarbon or a substituted hydrocarbon.

In one embodiment, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 in formula A are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, Lt; / RTI >

In one embodiment, R2, R4, R5, R6, R7 and R9 in formula (A) are each hydrogen.

In one embodiment, R3 and R8 in formula A are each independently alkyl, more preferably C1 to C8 alkyl, more preferably C1 to C4 alkyl, more preferably ethyl or methyl.

In one embodiment, at least one of R2, R3, R4, R5, R6, R7, R8, R9 and R10 in formula (A) is an arylamine.

In one embodiment, R1 in formula A comprises at least 6 carbon atoms.

In one embodiment, R1 in formula (A) further comprises at least one oxygen atom or at least one nitrogen atom.

In one embodiment, R1 in formula A further comprises at least 12 carbon atoms.

In one embodiment, in formula A, R10 comprises 6 or more carbon atoms.

In one embodiment, the at least one compound is selected from the following compounds.

,

,

In one embodiment, the one or more compounds are the following compounds.

The compounds of formula (A) may comprise a combination of two or more of the embodiments described herein.

In one embodiment, at least one compound is selected in formula (B).

In one embodiment, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 in Formula B are each independently a hydrocarbon or a substituted hydrocarbon.

In one embodiment, R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9 and R 10 in Formula B are each independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, Lt; / RTI >

In one embodiment, R2, R4, R5, R6, R7 and R9 in formula (B) are each hydrogen.

In one embodiment, R3 and R8 in formula B are each independently alkyl, more preferably C1 to C8 alkyl, more preferably C1 to C4 alkyl, more preferably ethyl or methyl.

In one embodiment, at least one of R2, R3, R4, R5, R6, R7, R8, R9 and R10 in Formula B is an arylamine.

In one embodiment, R < 1 > in formula (B) comprises at least 6 carbon atoms.

In one embodiment, R < 1 > in formula (B) further comprises at least one oxygen atom or at least one nitrogen atom.

In one embodiment, R < 1 > in formula (B) further comprises at least 12 carbon atoms.

In one embodiment, R < 10 > in formula (B) comprises at least 6 carbon atoms.

In one embodiment, the at least one compound is selected from the following compounds.

, 또는

, or

In one embodiment, the one or more compounds are the following compounds.

The compound of formula (B) may comprise a combination of two or more of the embodiments described herein.

In one embodiment, the at least one compound has a molecular weight of at least 400 g / mol, more preferably at least 500 g / mol.

In one embodiment, the at least one compound has a molecular weight of at least 600 g / mol, more preferably at least 700 g / mol.

In one embodiment, the at least one compound has a HOMO level of from -4.7 eV to -5.6 eV.

In one embodiment, the at least one compound has a LUMO level of -1.0 eV to -3.0 eV.

In one embodiment, the at least one compound has a triplet energy of 2.00 eV to 4.00 eV.

In one embodiment, the at least one compound has a sublimation temperature of at least 200 < 0 > C.

In one embodiment, the at least one compound comprises at least one deuterium atom.

The compounds of the present invention may comprise a combination of two or more of the embodiments described herein.

In one embodiment, the composition further comprises metal quinolate. In a further embodiment, the metal quinolate is lithium quinolate.

In one embodiment, the composition comprises 10 to 90 wt%, more preferably 10 to 70 wt% metal quinolate, based on the weight of the composition. In a further embodiment, the composition comprises 10 to 50 wt% metal quinolate, based on the weight of the composition. In a further embodiment, the composition comprises 20 to 50 wt% metal quinolate, based on the weight of the composition.

In one embodiment, the composition contains 10 to 90 wt%, more preferably 10 to 70 wt%, of lithium quinolate, based on the weight of the composition. In a further embodiment, the composition comprises 10 to 50 weight percent lithium quinolate, based on the weight of the composition. In a further embodiment, the composition comprises 20 to 50 weight percent lithium quinolate, based on the weight of the composition.

The compositions of the present invention may comprise a combination of two or more of the embodiments described herein.

The present invention also provides a film comprising at least one layer formed from the composition of the present invention in one or more embodiments described herein.

The present invention also provides an electronic device comprising at least one film layer formed from the composition of the present invention in one or more embodiments described herein.

The present invention also provides an electronic device comprising one or more components formed from the composition of the present invention in one or more embodiments described herein.

The compositions of the present invention are useful in related organic electronic device applications, including organic light emitting diodes (OLEDs), or organic solar cells. More specifically, the composition of the present invention is applied to individual layers of OLEDs including HIL (hole injection layer), HTL (hole transport layer), EML (emissive layer including host and dopant), ETL (electron transport layer) do.

The film of the present invention may comprise a combination of two or more of the embodiments described herein.

The apparatus of the present invention may comprise a combination of two or more of the embodiments described herein.

The compositions of the present invention may comprise a combination of two or more of the embodiments described herein.

The one or more compounds may comprise a combination of two or more of the embodiments described herein.

The compounds of formula (A) may comprise a combination of two or more of the embodiments described herein.

The compound of formula (B) may comprise a combination of two or more of the embodiments described herein.

The synthesis of the compounds of the present invention typically requires preparation of appropriately substituted 2-bromo-N- (2-bromophenyl) -N-phenylaniline. Such a molecule reacts with an appropriately substituted nucleophile to produce the desired phenophosphazene species. If desired, the phenoxaphosphine derivative can be oxidized with H ₂ O ₂ to produce the substituted phenophosphazene 10-oxide. Synthesis of substituted 2-bromo-N- (2-bromophenyl) -N-phenylaniline is accomplished using 2 equivalents of commercially available triarylamine and N-bromosuccinimide according to the prior art . 2-bromo-N- (2-bromophenyl) -N-phenylaniline is reacted with a substituted disubstituted canthospin to produce the desired product with a -C (aryl) . These molecules are further derivatized by R substitution of phenoxaphosphine 10-oxide to produce hole-transporting molecules. For example, see the following reaction.

The term "hydrocarbon" as used herein refers to a chemical group containing only carbon and hydrogen atoms (H and C; H; or C). The term "hydrocarbon" as used herein includes hydrogen.

The term "substituted hydrocarbons" as used herein refers to an aromatic hydrocarbon group in which one or more hydrogens are independently substituted with another group containing one or more heteroatoms and / or one or more carbons are independently substituted with another group containing one or more heteroatoms ≪ / RTI >

The term "aryl" as used herein refers to an organic group derived from an aromatic hydrocarbon. The aryl group may be monocyclic and / or fused ring structures, and each ring may suitably contain from 4 to 7, preferably 5 or 6, cyclic atoms. Also included is a structure in which two or more aryl groups are bonded through a single bond. Specific examples include but are not limited to phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl and the like It does not. Anthryl may be 1-anthryl, 2-anthryl or 9-anthryl, and fluorenyl may be 1-fluorenyl, 2-fluorenyl Fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl.

The term "heteroaryl ", as used herein, refers to an aromatic cyclic backbone atom having one or more heteroatoms selected, for example, from B, N, O, S, P (= O) Quot; refers to an aryl group containing a carbon atom as an atom. Heteroaryl may be a 5- or 6-membered monocyclic heteroaryl or polycyclic heteroaryl fused to one or more benzene rings and may be partially saturated. Also included are structures having one or more heteroaryl groups bonded through a single bond. The heteroaryl group may include a divalent aryl group, and the hetero atom of the heteroaryl group may be oxidized or quaternized to form an N-oxide, a quaternary salt, or the like. Specific examples include monocyclic heteroaryl groups such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, Triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, polycyclic heteroaryl groups such as benzofuranyl, benzothiophenyl, isobenzofuranyl , Benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, (Such as pyridyl N-oxide, quinolyl N-oxide), and quaternary salts thereof, can be converted to the corresponding N-oxides, But is not limited thereto.

(C6-C30) aryl, (C6-C30) aryl substituent-containing or non-containing (C3-C30) heteroaromatic groups containing one or more heteroatoms selected from deuterium, halogen, halogen substituted or unsubstituted 5- to 7-membered heterocycloalkyl containing one or more heteroatoms selected from aryl, for example B, N, O, S, P (= O), Si and P, (C3-C30) cycloalkyl, (C6-C30) cycloalkyl fused with one or more aromatic rings, tri (C1-C30) alkylsilyl, di (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, adamantyl, (C7-C30) bicycloalkyl, (C2-C30) alkenyl, _{carbazolyl, NR 21 R 22, BR 23} R 24, PR 25 R 26, P (= O) R 27 R 28 ( where R ₂₁ to R ₂₈ are independently selected from (C1-C30) alkyl, (C6-C30) (C1-C30) alkyl (C6-C30) aryl, (C1-C30) (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, (C6-C30) alkylthio, (C6-C30) arylcarbonyloxy, (C6-C30) aryloxycarbonyl, (C1-C30) alkoxycarbonyloxy, Oxycarbonyloxy, carboxyl, nitro and hydroxyl, or adjacent substituents joined together to form a ring.

Experiment

Reagents and Test Methods

All solvents and reagents are commercially available from purum, puriss or p.a. Respectively. Dry solvents were obtained from an in-house refining / dispensing system (hexane, toluene, tetrahydrofuran and diethyl ether) or purchased from Sigma-Aldrich. All experiments using moisture sensitive compounds were performed in oven-dried glassware under a nitrogen atmosphere or in a glove box. The reaction was monitored by analytical thin layer chromatography (TLC) on a precoated aluminum plate (VWR 60 F254) and visualized with UV light and / or potassium permanganate stain. Flash chromatography was performed on an ISCO COMBIFLASH system using a GRACERESOLV cartridge.

Unless otherwise noted, 1 H-NMR-spectra (500 MHz or 400 MHz) were obtained on a Varian VNMRS-500 or VNRMS-400 spectrometer at 30 ° C. Chemical shifts were based on one of the following: TMS in CHCl3 (delta = 0.00) in CDCl3, benzene-d5 (7.15) in benzene-d6 or DMSO-d5 (delta 2.50) in DMSO-d6. Peak assignments were performed using the COZY, HSQC or NOESY experiments, if necessary.

13C spectra (125 MHz or 100 MHz) were obtained on a Varian VNMRS-500 or VNRMS-400 spectrometer (solvent or standard signal: TMS in 0.0-CDCl3, 128.02-benzene-d6, 39.43-DMSO-d6).

A typical LC / MS study was performed as follows. A 5 microliter aliquot of the sample was coupled to the AGILENT 6520 QTof (quadrupole-time-of-flight) MS system via a double spray electrospray interface (ESI) operating in PI mode as a "3 mg / ml solution in THF" Gt; AGILENT < / RTI > 1200 SL binary gradient liquid chromatography. The following assay conditions were used: Column: 150 x 4.6 mm ID 3.5 mu m ZORBAX SB-C8; Column temperature: 40 占 폚; Mobile phase: 75/25 A / B to 15/85 A / B at 40 minutes; Solvent A = 0.1% by volume formic acid in water; Solution B = THF; Flow rate 1.0 mL / min; UV detection: Diode array 210 to 600 nm (extracted wavelength 250, 280 nm); ESI conditions: gas temperature 365 DEG C; Gas flow rate - 8 ml / min; Capillary - 3.5 kV; Nebulizer - 40PSI; Fragmenter-145 V.

Cyclic voltammetry measurements were performed using a WaveNano electrostatic cascade (Pine Research Instrumentation). (Silver wire immersed in a freshly prepared solution of 5 mM silver nitrate in anhydrous acetonitrile), platinum wire, and a platinum disk (1.6 mm diameter) with 0.1 M TBAP as a supporting electrolyte were added to the reference electrode, And used as a working electrode. All oxidation scans were performed on approximately 5 mM of the analyte solution in DCM (anhydrous) containing the supporting electrolyte 1M TBAP; All reduction scans were performed on 5 mM solutions in THF (anhydrous, inhibitor free) containing 0.1 M TBAP. Three cycles (6 segments) were typically run at a sweep rate of 20 mV / s. The energy level was corrected to an offset of 4.7 V and converted to a vacuum level.

DSC was performed using a 2000 instrument at a scan rate of 10 [deg.] C / min under a nitrogen atmosphere in all cycles. The sample (about 7 to 10 mg) was scanned from room temperature to 300 캜, cooled to -60 캜, and reheated to 300 캜. The glass transition temperature (T _g ) was measured on a second heat scan. Data analysis was performed using TA Universal Analysis software. T _g was calculated using the "center of inflection point" method.

modelling

All calculations were performed using Gaussian09 program ¹ . The calculations were performed with the hybrid density function theory (DFT) method B3LYP ² , and 6-31G * (5d) basis set ³ . The singlet condition calculation uses a closed shell approximation and the triplet condition calculation uses an open shell approximation. All values are expressed in electron volts (eV). The HOMO and LUMO values were measured from the orbital energies of the optimized geometry of the singlet ground state. Triplet energy was measured as the difference between the optimized triplet state and the total energy of the optimized singlet state.

1. Gaussian 09, Revision A.02, Frisch, M. J .; Trucks, G. W .; Schlegel, H. B .; Scuseria, G. E .; Robb, M. A .; Cheeseman, J. R .; Scalmani, G .; Barone, V .; Mennucci, B .; Petersson, G. A .; Nakatsuji, H .; Caricato, M .; Li, X .; Hratchian, H. P .; Izmaylov, A. F .; Bloino, J .; Zheng, G .; Sonnenberg, J. L .; Hada, M .; Ehara, M .; Toyota, K .; Fukuda, R .; Hasegawa, J .; Ishida, M .; Nakajima, T .; Honda, Y .; Kitao, O .; Nakai, N .; Vreven, T .; Montgomery, Jr., J.A .; Peralta, J. E .; Ogliaro, F .; Bearpark, M .; Heyd, J.J .; Brothers, E .; Kudin, K. N .; Staroverov, V. N .; Kobayashi, R .; Normand, J .; Raghavachari, K .; Rendell, A .; Burant, J. C .; Iyengar, S. S .; Tomasi, J .; Cossi, M .; Rega, N .; Millam, J. M .; Klene, M .; Knox, J. E .; Cross, J.B .; Bakken, V .; Adamo, C .; Jaramillo, J .; Gomperts, R .; Stratmann, R. E .; Yazyev, O .; Austin, A. J .; Cammi, R .; Pomelli, C .; Ochterski, J. W .; Martin, R. L .; Morokuma, K .; Zakrzewski, V. G .; Voth, G. A .; Salvador, P .; Dannenberg, J. J.; Dapprich, S .; Daniels, A.D .; Farkas, O .; Foresman, J.B .; Ortiz, J. V .; Cioslowski, J .; Fox, D. J., Gaussian, Inc., Wallingford CT, 2009.

2. (a) Becke, AD J. Chem . Phys . 1993 , 98 , 5648. (b) Lee, C .; Yang, W .; Parr, RG Phys. Rev B 1988 , 37 , 785. (c) Miehlich, B .; Savin, A .; Stoll, H .; Preuss, H. Chem . Phys . Lett . 1989 , 157 , 200.

3. (a) Ditchfield, R .; Hehre, WJ; Pople, JA J. Chem . Phys . 1971 , 54 , 724. (b) Hehre, WJ; Ditchfield, R .; Pople, JA J. Chem . Phys . 1972 , 56 , 2257. (c) Gordon, MS Chem . Phys . Lett. 1980 , 76 , 163.

4- (2,8-dimethyl-5- (p- Tolyl ) Pennosphospinine -10 (5H) -yl) -N, N- Of diphenyl aniline  Produce

A 250 mL Schlenk flask was charged with 2-bromo-N- (2-bromo-4-methylphenyl) -4-methyl-N- (p- tolyl) aniline (3.00 g, 6.74 mmol) Ethyl ether. The light yellow solution was cooled to -78 < 0 > C and n- BuLi (8.42 mL, 13.5 mmol) was added dropwise over a period of 15 min. After stirring at this temperature for 1 h, 30 mL of a THF solution of 4- (dichlorophosphino) -N, N-diphenyl aniline (2.33 g, 6.74 mmol) was added dropwise over a period of 15 min. The solution was slowly warmed to room temperature and stirred overnight. The solvent was removed by rotary evaporation and the residue was dissolved in 100 mL CH ₂ Cl ₂ . After washing several times, the organic layer with brine (3 × 100 mL), dried over MgSO _4. After filtration through Celite, the solution was removed by rotary evaporation and the residue was recrystallized from EtOH.

^{1 H NMR (400 MHz, CDCl} 3) δ 2.32 (s, 6H), 2.53 (s, 3H), 6.42 (dd, J = 4, 8 Hz, 2H), 6.98 (dd, J = 4, 8 Hz, J = 8 Hz, 4H), 7.45-7.53 (m, 4H), 7.65 (dd, J = , 8 Hz, 2H).

^{13 C {1 H} NMR (} CDCl 3) δ 20.5, 21.7, 113.3, 114.9, 117.2 (d, J = 12 Hz), 121.4 (d, J = 16 Hz), 124.9, 125.2, 127.2, 130.0, 132.2 ( d, J = 16 Hz), 130.9,131.6 (d, J = 10 Hz), 132.6,134.0 (d, J = 18 Hz), 135.2, 139.3 (d, J = 30 Hz), 143.6, 146.9, 150.9.

^{31 P {1 H} NMR (} CDCl 3) δ -0.3.

Purity after sublimation (LC-MS): 97.2%. Calculated: HOMO: -5.10; LUMO: -0.60.

10- (4- ( Diphenylamino ) Phenyl ) -2, 8-dimethyl-5- (p- Tolyl ) -5,10- Dihydro - Pennosphospinine  10- Oxide  Produce

To a solution of the prepared 4- (2,8-dimethyl-5- (p-tolyl) phenopospazin-10 (5H) -yl) -N, N-diphenyl aniline in CH ₂ Cl ₂ H ₂ O ₂ 30% aqueous solution (5 mL) was added. The biphasic mixture was stirred at room temperature overnight, then 5 mL of water was added. After separating the organic fraction, dried over MgSO _4, the solvent was removed by rotary evaporation. The residue was dissolved in ethyl acetate / hexane (1: 1) and filtered through a silica plug. The organic solvent was removed by rotary evaporation and the residue was recrystallized from CH ₂ Cl ₂ / hexanes to give a white solid (mass = 1.82 g, 58.9%), T _g = 123.5 ° C.

^{1 H NMR (400 MHz, CDCl} 3) δ 2.27 (s, 6H), 2.51 (s, 3H), 6.38 (dd, J = 4, 8 Hz, 2H), 7.01 (dd, J = 4, 8 Hz, 2H), 7.06 (m, 4H), 7.15 (t, J = 8 Hz, 4H), 7.28 (t, J = 8 Hz, 4H), 7.43-7.51 , 8 Hz, 2H).

^{13 C {1 H} NMR (} CDCl 3) δ 20.3, 21.3, 113.1, 114.2, 116.7 (d, J = 9 Hz), 120.0 (d, J = 18 Hz), 124.2, 124.9, 127.7, 129.4, 129.9 ( (d, J = 14 Hz), 130.3, 131.4 (d, J = 9 Hz), 131.8, 132.6 (d, J = 18 Hz), 133.2, 138.6 (d, J = 25 Hz), 142.9,

^{31 P {1 H} NMR (} CDCl 3) δ 6.4.

T _g = 123.5 ℃. Purity (LC-MS) after sublimation: 96.8%. Calculated: HOMO: -5.04; LUMO: -0.65.

These compounds can be used as film layers for OLED devices.

Claims (15)

A composition comprising at least one compound selected from the following compounds:
A)

Wherein R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9 and R 10 are each independently a hydrocarbon or a substituted hydrocarbon,
Wherein two or more R groups optionally selected from R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9 and R 10 may form one or more ring structures;
B)

(Wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are each independently a hydrocarbon or a substituted hydrocarbon,
Wherein two or more R groups optionally selected from R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9 and R 10 may form one or more ring structures; or
C) a combination of these. A compound according to claim 1, wherein R1, R2, R3, R4, R5, R6, R7, R9 and R10 in formula A are each independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl or substituted hetero Aryl,
Wherein R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9 and R 10 in Formula B are each independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl or substituted heteroaryl. 3. The composition of claim 1 or 2 wherein R2, R4, R5, R6, R7 and R9 are each hydrogen and R2, R4, R5, R6, R7 and R9 are each hydrogen. 4. The composition according to any one of claims 1 to 3, wherein R3 and R8 in formula A are each independently alkyl and R3 and R8 in formula B are each independently alkyl. 5. The composition of any one of claims 1 to 4, wherein R1 in formula (A) comprises 6 or more carbon atoms and R1 in formula (B) comprises 6 or more carbon atoms. 6. The composition of any one of claims 1 to 5 wherein R10 in formula A comprises at least 6 carbon atoms and R10 in formula B comprises at least 6 carbon atoms. The composition of claim 1, wherein the at least one compound is selected from the following compounds, or combinations thereof.

,

,

,

The composition of claim 1, wherein the at least one compound is selected from formula (A). 9. The compound of claim 8 wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are each independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl or substituted Gt; heteroaryl < / RTI > 9. The composition of claim 8, wherein the at least one compound is the following compound.

The composition of claim 1, wherein the at least one compound is selected from formula (B). Wherein R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9 and R 10 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl or substituted Gt; heteroaryl < / RTI > 12. The composition of claim 11, wherein the at least one compound is selected from the following compounds.

A film comprising at least one layer formed from the composition of any one of claims 1 to 13. 14. An electronic device comprising at least one element formed from the composition of any one of claims 1 to 13.