Electroluminescent device

FIELD: chemistry.

SUBSTANCE: electroluminescent device has a hole injection layer, a hole transport layer, an active luminescent layer based on electroluminescent substance of formula I , a hole blocking layer, an electron transport layer and an electron injection layer.

EFFECT: high luminance of devices emitting in the green spectral region.

1 ex

 

The invention relates to electroluminescent devices based on electroluminescent substances, namely, to electroluminescent devices using chelates of zinc as an active luminescent layer.

Known electroluminescent devices based on chelate complexes of zinc - bis[N-(2-oxybenzoates)cyclohexylamino]zinc, bis[N-(2-oxybenzoates)-4-tertbutylamine]zinc and N,N'-bis(oxybenzone)-1,2-phenylenediamine, emitting in the blue, green and red regions of the spectrum (Mggopwnu and other New electroluminescent materials based on chelate complexes of zinc // Izvestiya Academy of Sciences, Series of chemical, 2004, No. 10, s-2058).

Known electroluminescent device on the basis of a complex of zinc and its derivative N,N1bis(2-hydroxybenzylidene)-l,2-phenylenediamine containing electroconductive layer, hole-transport layer, hole-an injecting layer and the active luminescent layer on the basis of the above chelate complex of zinc (RF patent No. 2140956, SC 11/06, 1999). The device emits in the green region, has 480 brightness CD/m2when the voltage of 11.8 V and a current density of 26 mA/cm2that corresponds to the consumption of 6.4 W/CD.

Known electroluminescent device on the basis of a complex of zinc with ligands based on derivatives of 8-amino nolina, containing electroconductive layer, hole-transport layer, hole-an injecting layer and the active luminescent layer on the basis of the above chelate complex of zinc (RF patent No. 2310676, SC 11/06, 2006). The device emits in the blue-green region, has a brightness of 140 CD/m2when the voltage of 19 V and current density of 1.5 mA/cm2(efficiency 9 CD/A).

The closest in performance is the electroluminescent device containing electroconductive layer, hole-an injecting layer, hole-transport layer, an active luminescent layer on the basis of the electroluminescent substance of the formula I

(application WO 2009061233, SC 11/06, 2009).

The objective of the invention is the expansion of electroluminescent devices emitting in the green region of the spectrum.

The technical result of the invention is to increase the brightness of the devices emitting in the green region of the spectrum.

The technical result is achieved in that the electroluminescent device includes a hole injection layer, hole transport layer, an active luminescent layer on the basis of the electroluminescent substance bis[2-(2'-totalminutes) benzoxazole]zinc(2+) of the formula I

the hole blocking layer, electron transport layer, elect the config injection layer.

Compound I can be obtained by the reaction of 2-(2-totalminutes)benzoxazole with dihydrate zinc acetate. Compounds I can also be obtained by anodic dissolution of zinc in the combined acetonitrile solution of 2-(2-totalminutes)benzoxazole.

Examples of embodiment of the invention.

Example 1. Obtaining 2-(2'-totalminutes)benzoxazole.

Synthesis of 2-(2'-totalminutes)benzoxazole carried out by the method of [N.I. Chernov, M.V. Losev, Bolotin BM, Nurmukhametov RUSTAM., Riabokobylko US Chemistry of heterocycle. connect. 1973. No. 4. S-498].

The scheme for synthesis of:

To a solution of 10.91 g (0.1 mole) of o-aminophenol in 250 ml of dioxane with stirring add 30.97 g (0.1 mole) of the acid chloride tailandtramadol acid. The reaction mixture is cooled to room temperature. Spin-off oil after 30 minutes turns into a crystalline precipitate, which is filtered off, washed with cold methanol and crystallized from methanol. Acylated o-aminophenol are heated at 180-200°C. the Resulting mass is then cooled and purified by chromatographytandem on alumina (eluent - chloroform) followed by recrystallization from methanol. Get 22.5 g of pure substances. So pl. 165-166°C. the Yield 64% of theory.

Elemental analysis.

Found, %: C 66.10; H 4.51; N, 7.59; S 8.75.

Brutto-formula C20H1 N2O3S.

Calculated, %: C 65.91; H 4.43; N, 7.69; S 8.80.

An NMR spectrum1H (DMSO-d6), δ (ppm): 2.25 (s, 3H, CH3), 7.24-8.12 (m, N, CHAr), 11.44 (ush. s, 1H, NH).

IR-spectrum (powder), ν (cm-1), ν (cm-1): 1615 cf., 1588 S.,1538 cf. (benzoxazolone system), 1340 S. (νasSO2), 1160 O.S (νsSO2), 3433 (NH).

UV spectrum: 320, 400 nm (absorption, toluene). Luminescence 530, 580 (toluene λvasb=310, 380 nm). Quantum yield of luminescence φ=0.77 (powder).

Example 2. Obtaining bis[2-(2'-totalminutes)benzoxazole] zinc(2+) /I/

Synthesis of bis [2-(2'-totalminutes)benzoxazole] zinc(2+) was carried out according to the method [Burlov A.S., Kuznetsova L.I., Wabuska NV, kites O.Y, garnovsky A.D. Regioselective synthesis and spectral-luminescent properties of coordination compounds (o-totalminutes)benzazoles. // Ukr. General chemistry. 1998. So 68. No. 3. S-501] according to the scheme:

To a solution of 0.72 g (0.002 mole) of 2-(2-totalminutes)benzoxazole in 50 ml of methanol was added 0.22 g (0.001 mole) dihydrate zinc acetate in 5 ml of methanol. The mixture is refluxed for 1 h Fell upon cooling a white precipitate of the complex is filtered off and recrystallized from a mixture of chloroform: methanol (1: 2). Yield 0.6 g (76.7% of theory.). The substance does not melt up to 336°C.

Elemental analysis.

Found, %: C 60.40; N, 3.64; N, 7.17; Zn 8.55.

Brutto-formula C40H30N4O6S2Zn.

Calculated, %: C 60.64; N, 3.82; N, 7.07; Zn 8.25.

An NMR spectrum1H (DMSO-d6), δ (ppm): 2.27 (s, 6N, 2CH3), 7.04-8.36 (m, 24N, CAr-H).

IR-spectrum (powder), ν (cm-1): 1598 S., S. 1562,1538 cf. (benzoxazolone system), 1266 S. (νasSO2), 1133 O.S (νsSO2).

UV spectrum: 319, 361 nm (absorption, toluene). Luminescence 430 nm (toluene, λvasb=350 nm). Quantum yield of luminescence φ=0.28 (powder).

Example 3. Electrochemical obtaining bis[2-(2'-totalminutes)benzoxazole] zinc(2+) /I/.

Electrochemical synthesis of bis[2-(2'-totalminutes)benzoxazole]zinc(2+) carried out during anodic dissolution of zinc in oxidation state zero in the combined acetonitrile solution of 2-(2-totalminutes)benzoxazole (HL) according to the scheme:

The cathode (Pt): 2HL+2E→2L-+H2

The anode (Zn): Zn0-2E→Zn2+

Solution: 2L-+Zn2+→ZnL2

In the electrochemical cell was placed a solution of 0.1 g of 2-(2-totalminutes)benzoxazole (HL) in 15 ml of acetonitrile, as conductive additives used 0.05 g [Et4N]ClO4. The electrosynthesis is carried out at a constant current of 40 mA and a voltage of 15 V At room temperature for one hour. The precipitation of the complex is filtered off and recrystallized from a mixture of chloroform: methanol (1: 2). Output 0.087 g (80% of theory.). Substance which does not melt up to 300°C.

Elemental analysis.

Found, %: C 60.42; N, 3.73; N, 7.27; Zn 8.15.

Brutto-formula C40H30N4O6S2Zn.

Calculated, %: C 60.64; N, 3.82; N, 7.07; Zn 8.25.

NMR1N, IR and UV spectral characteristics of the complexes obtained by the chemical (example 2) and electrochemical (example 3) methods are identical.

Example 4. Electroluminescent properties.

Used in the work of substances and links to directories:

1. Phthalocyanine Copper complex (CuPc), ALDRICH, CAS 147-148.

2. 4,4',4"-Tris(N-(2-naphthyl)-N-phenyl-amino)triphenylamine (2-TNATA) KINTEC, lot: KZ88BuOMEEO, sales@kintec.hk.

3. NPD - N,N'-Bis(naphthalen-l-yl)-N,N'-bis(phenyl)- -benzidine (NPD) SIGMA-ALDRICH, CAS 123847-85-8.

4. 2,9-Dimethyl-4,7-diphenyl-l,10-phenanthroline (BCP) KINTEC, lot: KZ86BUOHRYO, sales@kintec.hk.

5. 4,7-Diphenyl-l,10-phenanthroline (Bphen) KINTEC, lot: KZ88BuOMEEO, sales@kintec.hk.

6. LiF ALDRICH, CAS: 7789-24-4.

For electroluminescence device /ELU/ with the structure ITO/CuPc/2-TNATA/NPD/zinc complex/BCP/Bphen/LiF/Al use a glass substrate with a transparent layer of a mixed oxide of indium and tin with resistance 30-70 Ω/square (hole-an injecting layer). On a substrate by evaporation in a vacuum consistently applied the following layers: layer Sears (hole-an injecting layer) with a thickness of 0.005 μm, the layer 2-TNATA (hole-transport layer) with a thickness of 0.045 μm, the NPD layer (hole-transport layer) with a thickness of 0.01 μm, a layer of zinc complex of a thickness of 0.025 μm, a layer of HRV (hole-blocking layer) with a thickness of 0.005 μm,Bphen layer (electron transport layer) with a thickness of 0.015 μm and a LiF layer (cathode injects layer) with a thickness of 0.001 μm. Then also by the method of vacuum evaporation of sprayed aluminum electrode (cathode injects layer). The thickness of the metal electrode is about 0.1 μm. The area of the illuminated surface 0.56 mm2. Received ELU emits green light when a forward voltage and has the following parameters: brightness 460 CD/m2is achieved at a voltage of 8 V and a current of 30 mA/cm2that corresponds to the luminous efficiency 0.67 Lm/W.

Electroluminescent device comprising a hole-an injecting layer, hole-transport layer, an active luminescent layer on the basis of the electroluminescent substance of the formula I

hole-blocking layer, electron transport layer, electron-injects layer.



 

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