Electroluminescent device

FIELD: electricity.

SUBSTANCE: invention relates to the electroluminescent device. The device contains hole injecting layer, hole transport layer, electronic block layer, active luminescent layer based on luminescent substance, hole-block layer, electronic transport layer, electronic injecting layer. As the luminescent substance it contains bis[2-(N-tosylamino)-benzylidene-2-aminopyridinato] of zinc (II) of formula I: .

EFFECT: electroluminescent device based on chelate complexes of zinc of azometin derivants 2-(N-tosylaminobenzaldehyde), emitting in yellow-green spectrum.

6 dwg, 1 tbl, 1 ex

 

The invention relates to electroluminescent devices ELU (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 sources of a new generation.

Known electroluminescent devices for use as emissive layers chelated zinc complexes, derivatives of salicylic aldehyde with various amines, for example bis[N-(2-oxybenzone)cyclohexylamino]zinc, bis[N-(2-oxybenzone)-4-tert-butylaniline]zinc and N,N'-bis(oxybenzone)-1,2-phenylendiamine emitting in blue, green and red regions of the spectrum (M. G. Kaplunov et New electroluminescent materials based on chelate complexes of zinc // news of Academy of Sciences, chemical Series, 2004, No. 10, pp. 2056-2058).

Known electroluminescent device based on N,N'-bis[(2-hydroxybenzylidene)-1,2-phenylendiamine]zinc containing electron-injecting layer, hole-injecting layer and the active luminescent layer on the basis of the above chelate complex of zinc (patent RF №2140956, C09K 11/06, 1999). The device emits in the green region, has the brightness of 480 CD/m2when the voltage of 11.8 V and a current density of 26 mA/cm2that corresponds to the power consumption 6.4 W/CD.

Known electric�luminescence device containing electron-injecting layer, hole-transport layer, hole-injecting layer and the active luminescent layer of zinc complex with ligands based on derivatives of 8-aminoquinoline (patent RF №2310676, C09K 11/06, 2006). The device emits in the blue-green region, has a brightness of 140 CD/m2at a voltage of 19 V and a current density of 1.5 mA/cm2(efficiency of 9 CD/A).

Known electroluminescent device, where the electroluminescent material using one of oxichinolina of metal complexes of 8-hydroxy-2-methoxyquinoline zinc or 8-hydroxy-2-methylinosine zinc (patent RF №2265840, IPC C09K 11/06, 2005). This device emits in the green region of the spectrum with the following parameters: brightness 140 CD/m2is achieved at a voltage of 16 V and a current density of 24 mA/cm2(efficiency of 4 CD/A).

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

This ELU emits in the green region of the spectrum and has the following �a*: luminance of 460 CD/m 2is achieved at a voltage of 8 V and a current of 30 mA/cm2that corresponds to the luminous efficacy 0.67 Lm/W (RF patent No. 2408648, IPC C09K 11/06, 2011).

Known emits in the blue region of the spectrum of the electroluminescent device, where the fluorescent substances are used complexes of zinc and aluminum of the General formula B, having a brightness of 204, 505, 695, 720 and 2124 CD/m2illumination rising from its voltage 9-15 V (application JP No. 2000026472 A, IPC C09K 11/06, 2000).

Known emits in the yellow region of the spectrum of a multilayer electroluminescent device, where the emissive layer is a zinc complex of bis{3-methyl-1-phenyl-4[(chinolin-3-imino)methyl]1-H-pyrazol-5-olate}zinc(II) (B), the structure of ITO/CuPc/2TNTA/Spiro-TRD/zinc complex B/BCP/BPhen/LiF/Al (λEL=600 nm) with a brightness of 800 CD/m2at a voltage of 10 V, which corresponds to the luminous efficacy of 0.5 LM/W [RF Patent №2470025, IPC C07F 3/06, C09K 11/06, 2012].

The closest in the implementation of the electroluminescent device is based on the films of bis(2-oxybenzone-4-tert-butylaniline)zinc formula G, and mixtures thereof (99%) with Nile red (1%), emitting in the green and red regions of the spectrum. The green emission has a brightness 480 CD/m2at a voltage of 11 V and a current density of 2 mA/cm2. Red radiation has a bright�ness of 0.4 CD/m 2at a voltage of 11 V and a current density of 30 mA/cm2(Patent RF №2155204, IPC C09K 11/06, 2000).

The object of the invention is the expansion of the electroluminescent devices emitting in the yellow-green region of the spectrum.

The technical result of the invention is an electroluminescent device based on chelate complexes of zinc azomethine derivatives of 2-(N-tosylaminophenyl), emitting in the yellow-green region of the spectrum.

The technical result is achieved in 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, a luminescent substance contains bis[2-(N-tosylamide)-benzyliden-2-aminopyridine]zinc(II) formula I:

The invention meets the criterion of inventive step, is not known electroluminescent devices emitting in the yellow-green region of the spectrum, with active luminescent layer based on a zinc chelate complexes of 2-(N-tosylamide)-benzyliden-2-aminopyridines.

Bis[2-(N-tosylamide)-benzyliden-2-aminopyridine]zinc(II) is known as a compound exhibiting luminescent�ing activity (patent RF №2295527, example 7, IPC C09K 11/06, 2007).

Below is an example of getting a connection.

Example 1.

Obtaining bis[2-(N-tosylamide)-benzyliden-2-aminopyridine]zinc(II) - compounds I.

The synthesis of compounds made according to the scheme:

To a solution of 0.55 g (2 mmol) 2-(N-tosylamide)-benzaldehyde in 20 ml of ethanol was added 0.19 g (2 mmol) 2-aminopyridine in 20 ml of ethanol and 0.22 g (1 mmol) dihydrate zinc acetate in 10 ml of ethanol. The mixture is boiled. Precipitated after cooling, the precipitate of the complex was filtered, washed with ethanol and recrystallized from a mixture of benzene:ethanol (1:2).

Get yellow crystals. The yield of 84%. TPL>250°C.

Elemental analysis:

Found, %: C Is At 59.69; H, 4.29; N, 11.07; Zn 8.35.

Gross formula C38H32N6O4S2Zn.

Calculated, %: C, 59.57; H 4.21; N, 10.96, Zn 8.53.

1H NMR spectrum (CDCl3), δ (M. D.):

2.29 (3H, s, CH3), 6.87-7.86 (11H, m, CAr-H), 8.33 (1H, d,3J=4.8 Hz, CAr-H), 9.2 (1H, s, CH=N).

In the IR spectra (powder) registered absorption bands, ν (cm-1):

1611 (CH=N), 1257 (as SO2), 1139 (s, SO2).

Fig.1 shows the electronic absorption spectrum of compound I.

In the electronic absorption spectrum of I in chloroform observed two absorption bands at λabs=308 nm and λabs=394 nm.

Fig.2 shows the photoluminescence spectrum of compound I, where the axis AB�the Cisse delayed values of the wavelength, in nanometers, and on the ordinate the values of fluorescence in arbitrary units. When excited I the photoluminescence spectrum has a maximum at λPL=498 nm and undergoes a bathochromic shift (104 nm).

Fig.3 shows the General scheme of the electroluminescent device in longitudinal section. In table 1, including the names of the layers 1-14.

Table 1
POS. only.NameNumber
1Glass plate1
2Anode : ITO-In2O3:SnO21
3Metallic contact to the anode1
4Hole injection layer: CuPc (copper phthalocyanine), layer thickness 3 nm1
5Hole transport layer: 2-TNATA (4,4',4" tri(2-naftifine-phenylamino)-include naphtha), the layer thickness of 35 nm1
6�electronic blocking layer: TPD (N,N'-bi(3-methylphenyl)-N,N'-diphenylbenzidine), the layer thickness of 6.5 nm1
7Active luminescent layer: bis[2-(N-tosylamino)benzilidene-R'-2'-aminopyridine]zinc(II) I, the layer thickness of 23 nm1
8Hole blocking layer: BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthrolin), the thickness of the layer 51

nm
9Electron transport layer: BPhen (4,7-diphenyl-1,10-phenanthrolin), the layer thickness of 26 nm1
10Electronic injection layer: LiF, the layer thickness of 0.8 nm1
11Cathode: Al (100 nm)1
12The separation path1
13Conductor to the cathode1
14Metallic contact to the cathode1

As a solid transparent substrate (1) use commercially available glass substrate coated with transparent conductive layer of indium oxide doped with tin, which is the anode (2) is connected to a metal contact (3). Next, by the method of thermal vacuum evaporation a layer of injecting holes from the copper phthalocyanine (CuPc) (4), hole-transport layer of 2-TNATA-(4,4',4"-three(2-naftifine-phenylamino)-include naphtha) (5), electron-blocking layer TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenylbenzidine) (6), an active luminescent layer of the electroluminescent substance bis[2-(N-tosylamide)benzyliden-R'-2'-aminopyridine]zinc(II) of the General formula I (7), hole-blocking layer of BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) (8), the electron transport layer is Bphen (4,7-diphenyl-1,10-phenanthrolin) (9), electron-injecting layer (LiF) (10) and the aluminum cathode (11). The separation path (12) on the electrode coating of indium oxide doped with tin, divides the transparent conductive layer on the anode (2) and cathode zones. The cathode area was also the conductor to the cathode (13) and has a metal contact (14). The thickness of the layers in the manufacture by the method of thermal vacuum evaporation is strictly controlled.

Table 1 presents the chemical composition below when�Eden substances and the thickness of the functional layers of the device using conventional in the literature abbreviations of ports:

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

4,4',4"-Tris(N-(2-naphthyl)-N-phenyl-amino)triphenylamine (2-TNATA)

KINTEC, lot: KZ88BuOMEEO, sales@kintec.hk

TPD is N,N'-bis(3-methylphenyl)-N,N'-diphenylbenzidine SIGMA - ALDRICH, CAS 443263-5G

2,9-Dimethyl-4,7-diphenyl-1,10-phenanhroline (BCP) KINTEC, lot: KZ86BUOHRYO, sales@kintec.hk

4,7-Diphenyl-1,10-phenanthroline (Bphen) KINTEC, lot: KZ88BuOMEEO, sales@kintec.hk

LiF ALDRICH, CAS: 7789-24-4.

Before using the substance is subjected to repeated treatment by resultant deposition. The formation of a multilayer structure of acid and measurement of performance is carried out in an inert atmosphere of argon in the absence of contact with the atmosphere. Layers applied by thermal vacuum evaporation. The complex I showed a high thermal stability by thermal vacuum evaporation, which makes it a promising material for use in OLED technology.

Fig.4 shows the spectrum of the electroluminescence EL, where the abscissa axis shows the values of the radiation wavelength in nanometers and the ordinate values of electroluminescence in relative units. As can be seen from Fig.4. ELU has an emission maximum at 525 nm. Band emission in the spectrum of the electroluminescence ELU is being compared to the photoluminescence spectrum of Ia bathochromic shift of 27 nm.

On f�G. 5 shows the chromaticity coordinates (CIE) ELU, and Fig.6 shows current-voltage (a) and voltage-brightness (b) characteristics of the device.

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) is the recombination of these charges, which causes the effect of electroluminescence (emission of light). The 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.

Found that this configuration of acid and the specified thickness of the layers, brightness 220 CD/m2at an operating voltage of 10 V, the CIE coordinates (x=0.409, y=0.506) Fig.5. The maximum brightness of the device is greater than 1000 CD/m2At 16 V and a current density of 600 mA/cm2The luminous efficiency of the device is about 1 LM/W, the threshold voltage of 5 V.

Thus, AL-based compounds with the formula I demonstrates high performance, allowing it to be used as an emitting organic material in the sources of illumination with yellow-green light, and also leads to expansion of the range of acid.

Electroluminescent device comprising a hole injecting layer, a hole transport layer,electron blocking layer active luminescent layer based fluorescent substance, a hole-blocking layer, electron transport layer, electron injecting layer, characterized in that the luminescent substances it contains bis[2-(N-tosylamide)-benzyliden-2-aminopyridine]zinc(II) of the formula I



 

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