Bis[2-(n-tozylamino)benzyliden-4'-dimethylaminophenyliminato]zinc(ii) and based on it electroluminiscent device

IPC classes for russian patent Bis[2-(n-tozylamino)benzyliden-4'-dimethylaminophenyliminato]zinc(ii) and based on it electroluminiscent device (RU 2518893):

H05B33/14 - characterised by the chemical or physical composition or the arrangement of the electroluminescent material

C09K11/06 - containing organic luminescent materials

C07F3/06 - Zinc compounds

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FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds in a series of chelate complexes of zinc with azomethine derivatives, namely to bis[2-(N-tozylamino)benzyliden-4'-dimethylaminophenyliminato]zinc(II) of formula I Also claimed is electroluminescent device.

EFFECT: invention makes it possible to obtain compounds, demonstrating electroluminescent properties with high brightness.

2 cl, 3 dwg, 1 tbl, 2 ex

The invention relates to new compounds in the range of chelated zinc complexes with derivatives of h, namely 2-(N-tosylamide)benzylidene-4'-dimethylaminobenzylidene, formula I,

showing electroluminescent properties, and electroluminescent devices (organic light-emitting diodes, known as acid or OLED - Organic Light Emitting Diodes, which are used as an effective and highly efficient solid-state light source new generation) by using the above compounds as the active luminescent layer.

Known electroluminescent devices based on chelate complexes of zinc, derivatives of salicylic aldehyde with various amines, 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 others, New electroluminescent materials based on chelate complexes of zinc // Izvestiya Academy of Sciences, Series of chemical, 2004, No. 10, S. 2056 - 2058).

Known electroluminescent device on the basis of a complex of zinc and its derivative N,N¹bis(2-hydroxybenzylidene)-1,2-phenylenediamine containing electroconductive layer, hole-an injecting layer is active luminescent layer on the basis of the above chelate complex of zinc (RF patent No. 2140956, CC 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 containing electroconductive layer, hole-transport layer, hole-injects the active layer and the fluorescent layer of the complex of zinc with ligands based on derivatives of 8-aminoquinoline (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).

Known electroluminescent device comprising a hole-an injecting layer, hole-transport layer, an active luminescent layer-based fluorescent substance, a hole-blocking layer, electron transport layer, electron-an injecting layer, characterized in that the fluorescent substance use bis[2-(2'-totalminutes)benzoxazole]zinc(2+) formula A.

And

This ELU emits in the green region of the spectrum 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 (RF patent No. 2408648, IPC C09K 11/06, 2011).

Known electrolu inessential device, consisting of electronic an injecting layer, an active luminescent layer based on chelate complex of a metal, a hole-transport layer and an injecting hole layer. As the fluorescent substance contains one of oxichinolina metal complexes of 8-hydroxy-2-methoxyquinoline zinc or 8-hydroxy-2-methylinosine zinc (RF patent No. 2265940, IPC H01S 3/13, 2005). The electroluminescent material emits in the green region of the spectrum with the following settings: brightness of 140 CD/m²is achieved at a voltage of 16 V and a current density of 24 mA/cm²(efficiency 4 CD/A).

As the fluorescent substance in electroluminescent devices emitting in the blue region of the spectrum, are complexes of zinc and aluminum in the General formula B, with brightness from 204, 505, 695, 720 and 2124 CD/m², which can only be achieved when the voltage 9-15 (application JP No. 2000026472 A, IPC C09K 11/06, 2000).

The closest in performance is the electroluminescent device based on the films of bis(2-oxybenzone-4-tertbutylamine)zinc formula, and mixtures thereof (99%) with Nile red (1%), emitting in the green and red regions of the spectrum. Green radiation has the brightness of 480 CD/m²at a voltage of 11 V and a current density of 2 mA/cm². Red radiation has a brightness of 0.4 CD/m²when the voltage is AI 11 and a current density of 30 mA/cm ²(Patent RF № 2155204, IPC C09K 11/06, 2000).

The task of the invention to provide an electroluminescent materials based on chelate complexes of zinc, emitting in the yellow region of the spectrum.

In a series of chelate complexes of zinc with bases 2-(N-tosylamide)benzaldehyde unknown compounds exhibiting the electroluminescent properties.

The technical result of the invention are compounds in a series of chelate complexes of zinc with bases 2-(N-tosylamide)benzaldehyde , showing electroluminescent properties with high brightness, and the device on the basis of them.

Technical result is achieved by the new connection bis[2-(N-tosylamide)benzylidene-4'-dimethylaminobenzylidene]zinc(II) of formula I.

The technical result is also achieved by the fact that the electroluminescent device comprising a hole injection layer, hole transport layer, an active luminescent layer-based fluorescent substance, a hole blocking layer, electron transport layer, electron injection layer as a luminescent substance contains bis[2-(N-tosylamide)-benzylidene-4'-dimethylaminobenzylidene]zinc(II) of the above formula I.

The invention satisfies the criterion of inventive step, in a number of the azomethines 2-(N-tosylamide)benzaldehyde unknown compounds as ligands complexes of zinc, showing electroluminescent properties.

Compound I can be obtained by the reaction of 2-(tosylamide)-benzylidene-4'-dimethylaminobenzylidene with hydrate of zinc acetate in ethanol.

Examples of embodiment of the invention.

Example 1. Getting 2-(N-tosylamide)-benzylidene-4'-dimethylaminobenzylidene.

The scheme for synthesis of:

To a solution of 2.75 g (0.01 mol) of 2-N-tosylaminophenyl in 50 ml of ethanol was added to 1.36 g (0.01 mol) 4-dimethylaminopyridine in 10 ml of ethanol. The mixture was boiled under reflux for one hour. Fallen upon cooling the residue of h was filtered off, washed with 2 times 5 ml of ethanol and recrystallized from a mixture of chloroform: ethanol (1 : 2).

Yellow-orange crystals. Output 3,34 g (85%). TPL 194-195°C.

Elemental analysis:

Found, %: C 67,20; H 5,91; N 10,57.

Brutto-formula C₂₂H₂₃N₃O₂S.

Calculated, %: C 67,15; H Of 5.89; N Is 10.68.

¹H NMR spectrum (DMSO-d₆), δ (M. D.):

2.28 (3H, s, CH₃), 2.96 (6N, s, N(CH₃)₂), for 6.81 (2H, d, J = 9 Hz, C_Ar-H), 7,14-7,29 (1H, m, C_Ar-H), 7,32-7,47 (6H, m, C_Ar(H)to 7.61-to 7.68 (3H, m, C_Ar(H)8,78 (1H, s, CH=N), 13,38 (1H, s, NH).

In IR - spectra (powder) contains absorption bands, ν (cm^-1):

2890 W (NH), 1616 (CH=N), 1589, 1565, 1517, 1497, 1441, 1362, 1326 (as SO₂), 1281, 1229, 1156 (s, SO₂), 1117, 1090, 1044, 969, 882, 871, 805, 777, 767, 722, 657, 628, 07.

Example 2. Obtaining bis[2-(N-tosylamide)-benzylidene-4'-dimethylaminobenzylidene]zinc(II) - compound I.

The synthesis of compounds made according to the scheme:

To a solution 0,78 g (0.002 mol) of 2-(N-tosylamide)-benzylidene-4'-dimethylaminopyridine in 20 ml of ethanol was added to 0.22 g (0.001 mol) dihydrate zinc acetate in 10 ml of ethanol. The mixture was boiled for two hours. Precipitated by cooling the precipitated complex was filtered off, washed with 2 times 5 ml of ethanol and recrystallized from a mixture of benzene : ethanol (1 : 2).

Yellow-orange crystals. Output 0,70 g (82%). TPL 254-255°C.

Elemental analysis:

Found, %: C 65,21; H 5,28; N To 9.91; Zn 7,72.

Brutto-formula C₄₄H₄₄N₆O₄S₂Zn.

Calculated, %: C 65,15; H 5,22; N 9,88, Zn 7,69.

¹H NMR spectrum (DMSO-d₆), δ (M. D.):

2.29 (3H, s, CH₃), 2.90 (6N, s, N(CH₃)₂), to 6.67 (2H, d, J = 9 Hz, C_Ar-H), 6.89 in (1H, t, J = 7.2 Hz, C_Ar-H), 7,07 (2H, d, J = 7.8 Hz, C_Ar-H), 7,22-7,49 (6H, m, C_Ar(H)7,72 (1H, d, J = 7.8 Hz, C_Ar(H)to 8.70 (1H, s, CH=N).

In IR - spectra (powder) contains absorption bands, ν (cm^-1):

1611 (CH=N), 1588, 1552, 1515, 1478, 1439, 1296, 1272, 1257 (as SO₂), 1191, 1173, 1139 (s, SO₂), 1084, 1059, 948, 928, 897, 855, 813, 762, 746, 708, 661, 646, 585, 577, 556.

In Fig. 1 shows a photoluminescence spectrum of compound I, where x-axis values of the wavelength in nanometers and the y-axis is meant is I fluorescence in arbitrary units. As can be seen from the figure, the quantum yield of photoluminescence of compound I in a solution of chloroform is 2%.

Figure 2 presents electroluminescence spectrum of the compound I where x-axis values of wavelength in nanometers and the y-axis values of electroluminescence in relative units. As can be seen from the figure, the radiation has a soft yellow color.

The data of elemental analysis,¹H NMR, IR, UV spectral characteristics indicate the formation of structure I.

In Fig. 3 presents the General scheme of the electroluminescent device in longitudinal section. As a solid transparent substrate (1) use a commercially available glass substrate coated with a transparent conductive layer of a mixture of In₂O₃/SnO₂, which is the anode (2)is connected to the metal contact (3). Next, the method of irrigation on the centrifuge (spin-coating) put a layer that injects holes from poly(3,4-ethylenedioxythiophene):poly(styrene sulfonate) (PEDOT:PSS) (4), then by the method of thermal vacuum evaporation (TWI) put a hole transport layer (5), electron-blocking layer (6), the light emitting layer of 2-(N-tosylamide)-benzylidene-4'-dimethylaminobenzylidene (formula I) (7), hole-blocking layer of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) (8),electron transport layer (4,7-diphenyl-1,10-phenanthroline) (BPhen) (9), e injects a layer of lithium fluoride (LiF) (10) and aluminum cathode (11). Dividing a track (12) at the electrode coating of a mixture of In₂O₃/SnO₂isolates the anode (2) cathode. Cathode area also serves as a current conducting wire to the cathode (13) and has a metal contact (14). The thickness of each layer in the process of its formation by the method of thermal vacuum evaporation is strictly controlled.

Table 1 lists the chemical composition and the thickness of the functional layers of the device using generally accepted in the literature abbreviations connections.

Table 1

POS. the hereafter.	Name	Qty
1	Glass plate	1
2	Anode: ITO - In₂O₃:SnO₂	1
3	The metal contact to the anode	1
4	The hole injection layer: PEDOT:PSS (polyethyleneoxide: polystyrenesulfonate), the layer thickness of 40 nm	1
5	The hole transport layer: 2-TNATA (4,4,4” three(2 - naphthylvinyl-phenylamino)- triphenylamine), the layer thickness of 27 nm	1
6	Electronic blocking layer: spiro-TPD (N, N - bi(phenyl)-9,9 - spirobifluorene), the layer thickness of 6 nm	1
7	Active luminescent layer: bis[2-(N-tosylamide)-benzylidene-4'-dimethylaminobenzylidene]zinc(II), the layer thickness of 20 nm	1
8	The hole blocking layer: BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthrolin), layer thickness 5 nm	1
9	Electronic transport layer: BPhen (4,7 - diphenyl-1,10 - phenanthrolin), the layer thickness of 22 nm	1
10	Electron injection layer: LiF, the layer thickness of 0.9 nm	1
11	Cathode: Al (100 nm)	1
12	Dividing track	1
13	Conductors to the cathode/td>	1
14	The metal contact to the cathode	1

When voltage is applied to the anode (2) and the cathode (11) of them in the neighboring conductive layers injections, respectively, holes and electrons, which move towards each other. In the light-emitting layer (7) recombination of these charges, which causes the effect of electroluminescence (light emission). Blocking layers (6) and (8) provide for the accumulation of electrons and holes in the layer (7), thereby increasing the efficiency of recombination of charges, i.e. the radiation intensity.

It was established that in the wavelength range from 500 to 750 nm at a specified thickness of the layers, the brightness of the radiation received OID is 1000 CD/m²at an operating voltage of 14 V, the CIE coordinates (x=0.431, y=0.537).

Thus, the electroluminescent device based on the connection with formula I exhibit high performance characteristics that can be used as emitting organic material in the light sources with a soft yellow light. This is confirmed by the achievement of a new technical result is compared with the known technical solution, as well as expanding the range of acid.

1. Bis[2-(N-tosylamide)benzylidene-4'-dimethylaminobenzylidene] zinc(II) of the formula I
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2. The electroluminescent device, comprising an injecting hole layer, hole transport layer, electron blocking layer, an active luminescent layer-based fluorescent substance, a hole-blocking layer, electron transport layer, electron injects layer, characterized in that the luminescent substances it contains bis[2-(N-tosylamide)benzylidene-4'-dimethylaminobenzylidene]zinc(II) of formula I.