Electroluminescent material containing organic luminescent substance

FIELD: luminescent substances, organic chemistry.

SUBSTANCE: invention relates to electroluminescent materials containing organic luminescent substance. Invention describes novel electroluminescent material consisting of injection layer, active luminescent layer based on chelate metal complex, hole-transporting layer and hole-injecting layer. Material comprises metal complexes based on sulfanyl derivatives of 8-aminoquinoline as a luminescent substance, in particular, zinc complexes of 8-(methylsulfanylamino)-quinoline and 8-(3,5-difluorophenylsulfanylamino)-quinoline. Material comprises a mixture of triphenylamine oligomers as a hole-transporting layer. Invention provides creature of electroluminescent material showing the enhanced moisture resistance, enhanced resistance to crystallization and enhanced thermal stability.

EFFECT: improved and valuable properties of material.

4 cl, 5 ex

 

The invention relates to luminescent materials, namely, electroluminescent materials containing organic fluorescent substance.

Known electroluminescent material (ELM), consisting of electronic an injecting layer, an active luminescent layer-based fluorescent substance, a hole-transport layer and the hole-an injecting layer containing the luminescent layer evaporated layer of organic compounds - complexes of aluminum, zinc and some other metals derived from 8-hydroxyquinoline solution [U.Mitschke, P.Bauerle. J.Mater. Chem., 2000, 10, 1471-1507].

The closest to the technical nature of the present device is ELM, containing a luminescent layer of Tris-(8-hydroxyquinolinato) aluminum [C.W.Tang, S.A.Van Slike Appl. Phys. Letter 51, 913-915 (1987)] (see Fig.).

At the same time as the hole-an injecting layer (anode) is applied transparent low-resistance layer based on a mixed oxide of indium and tin, In2O3-SnO3(ITO), as the electron-an injecting layer (cathode) is aluminum or an alloy of magnesium and silver, and as the hole-transport layer is N,N'-diphenyl-N,N'-(3-were)-1,1'-biphenyl-4,4'-diamine (TPD).

However, the time resource electroluminescent devices based on such complexes are often small. Besides what about the other reasons this is due to the properties of these materials: their crystallization in the process of working devices, that changes the uniformity of the conductive layer properties, as well as the hydrolysis of metal complexes with traces of water and oxidation by oxygen in the air with their subsequent decay [S. Tokito et al., Appl. Phys. Lett. 1997, v.70, No15, p.1929-1931; P.E. Burrows et al., Appl. Phys. Lett. 1994, v.65. No 23, p.2922-2924]. It also leads to the loss of the operational characteristics of this layer.

In addition, the time resource electroluminescent devices is limited to low temperature resistant materials, hole-transport layers, due to changes in the morphology of the layer with increasing temperature because of their low glass transition temperature (for TPD, the glass transition temperature is 60°).

The present invention is the creation of ELM with increased temporary resource due to the increased stability of the active luminescent layer with respect to crystallization and hydrolysis, as well as high temperature resistance of the hole-transport layer.

The problem is solved by the fact that according to the invention the electroluminescent material consisting of e an injecting layer, an active luminescent layer-based fluorescent substance, a hole-transport layer and the hole-an injecting layer, as a fluorescent substance containing the metal complexes with ligands derived 8-aminoquinoline total fo the formula (I):

where M=Zn, n=2;

the group R1can be selected from the set:

is an alkyl group of 1-4 carbon atoms and having a normal or branched structure;

- aryl group; a mono - or polyhalogen phenyl group in which the halogen atoms are fluorine, chlorine, bromine, iodine; mono - or polyalkylene phenyl group, in which

- alkyl substituents consist of 1 to 4 carbon atoms and have a normal or branched structure; R2-R7- hydrogen.

As examples of substances according to formula (I) can be used zinc complexes of 8-(methylsulfonylamino)quinoline (II) and 8-(3,5-differentialformen)quinoline (III):

In sulfonylamino quinoline derivatives hydrogen atom linked to the nitrogen atom in its acidity is comparable with the corresponding hydrogen atom of phenolic hydroxyl. This allows you to get a solid salts (complexes with metal ions.

Bulky substituents at the nitrogen atom in the metal complex should impede the rapid crystallization of the latter in the electron transport layer when the device, which can improve his time resource compared with the device using the metal complexes of 8-hydroxyquinoline solution.

The volume of the s deputies alkyl - or arylsulfonyl fragments in 8-aminoquinoline screen the approach of water molecules due to the nitrogen - the metal, which hinders the hydrolysis of the metal complex in comparison with those based on 8-hydroxyquinoline solution. It also should have a positive impact on the operating time of the device.

The problem is solved also by the fact that as the hole-transport layer material preferably comprises a mixture of oligomers of triphenylamine with the General formula

where n=8-9, when the molecular-mass distribution: Mn=2332, Mw=3586 characterized by high glass transition temperature 185°that ensures the preservation of the morphology of the hole-transport layer even at elevated temperatures [Yakushenko I.K., Kaplunov MG, Shamayev, S.N., Efimov O.N., Nikolaeva, GV, Belov, M., Marchenko, H.E., starlings A.G., Voronin, VA "a Method of obtaining a mixture of oligoadenylates, the method of obtaining 3-(4-biphenylyl)-4-(4-tertbutylphenyl)-5-(4-dimethylamino-phenyl)-1,2,4-triazole and the electroluminescent device", Patent of Russian Federation N 2131411 from 10.06.99].

The invention is illustrated by the following examples.

Example 1. Synthesis of 8-(methanesulfonamido)quinoline (IV)

The syntheses are carried out by well-known methods [getter chemicals and drugs. The issue 4-5, Moscow, IREA, 1962, p.67-69.]

The scheme for synthesis of:

To a solution 2,88 g (0.02 M) 8-aminoquinoline in 10 ml of dry pyridine while cooling to 3-5°p is imously a solution of 2.8 g (0.02 M) methanesulfonamide in 3.5 ml of dry tetrahydrofuran. Time adding 15-20 minutes Then the mixture was stirred at the same temperature for 30 minutes, then 1 hour at boiling reaction mixture. After that drove the solvent, the residue was cooled to room temperature and treated with 75 ml of water. The formed precipitate was filtered, washed with 20 ml water, dried in the air. Received of 4.54 g of the crude product (IV). The compound (IV) to recrystallize from benzene (followed by the addition of hexane). Got 3,93 g of pure substances.

TPL 146,5-147°C. Output and 88.5% of theoretical.

Elemental analysis. Found, %: C Is 55.74; H 4,78; N 12,15; S 14,34. Gross formula C10H10N2About2S. Calculated, %: 54,04; N. Of 4.54; N 12,60; S 14,34. PMR-spectrum δ (ppm) a 3.15 (3H, CH3-, C.), to 7.59-7,63 (H3Shostakovich), to 7.64-7.68 per(H6Shostakovich), 7,73 to 7.75 (H7D.), of 7.75-to 7.77(H5D.), 8,44-8,46 (H4forth), to 8.94-8,96 (H2forth), 9,39 (NH, s).

Mass spectrum: m/e (I/Imax, %): 222 (M, 43), 143 (100), 116 (75), 89 (31), 63 (22), 39 (15).

Example 2. Synthesis of 8-(3,5-differentialformen)quinoline (V)

The scheme for synthesis of:

To a solution 2,02 g (0,014 M) 8-aminoquinoline in 5 ml of dry pyridine while cooling to 3-5°C was added a solution of 3.4 g (0,016 M) 3.5-differentsoftware in 10 ml of tetrahydrofuran. Time adding 10-15 min. the Mixture was stirred at the same temperature for 30 minutes, then at room 1 hour and 1 hour at the boiling reaction mixture. After this is about the mixture was cooled and treated with 250 ml of cold water. The precipitate was filtered off, washed with water, dried. The crude product (4,75 g) was dissolved by heating in benzene, the solution was filtered to remove insoluble impurities, the filtrate was added hexane. Resulting precipitate of compound (V) was filtered, washed with hexane, and dried. Got to 3.89 g of substance VI. TPL 119-119,5°C. Yield 87% of theoretical.

Elemental analysis. Found, %: C 54,00; N Is 4.21; N 8,70; S 10,37. Gross formula C15H10F2N2About2S. Calculated, %: C 56,25; N 3,15; 8,75 N; S 10,01. PMR-spectrum δ (ppm) 7,53-7,58 (1H from Ph, H3, m), 7,58-7,71 (H6Shostakovich), 7,63-of 7.70 (2H Ph, m), 7,69-7,72 (H7forth), 7,73-7,76 (H5forth), scored 8.38-8,40 (H4forth), cent to 8.85-8,87 (H2forth), and 10.5 (NH, s).

Mass spectrum: m/e (I/Imax, %): 320 (M, 35), 256 (40), 143 (100), 116 (78), 89 (31), 63 (27), 39 (12).

Example 3. Synthesis of bis-((8-methanesulfonamido)hyalinata)zinc (II)

The scheme for synthesis of:

2,22 (0.01 M) 8-(methanesulfonamido)quinoline (IV) suspended in 25 ml of dry methanol. To this mixture at room temperature was added a solution of sodium methylate, obtained by dissolution of 0.23 g (0.01 M) sodium in 6 ml of methanol. It was formed precipitate the sodium salt of the compound (IV). The mixture was stirred for 30 min at the same temperature, and then was added dropwise a solution of 0.68 g (0.005 M) of anhydrous zinc chloride in the form of its solution in ml dry methanol. Then the mixture was stirred for 2 hours while heating to 50-55°C. Upon cooling was filtered, the precipitate is white, washed it successively with water, methanol. Dried in vacuum over P2O5. Got to 2.41 g of compound (II). Output 95,1% of theoretical. For further purification, the substance was recrystallized from tetrahydrofuran. The substance does not melt up to 380°C.

Elemental analysis. Found, %: C 47,57; N 3,99; N 10,36; S 11,46; Zn 12,86. Gross formula C20H18N4About4S2Zn. Calculated, %: C 47,30; N 3,57; N 11,03; S 12,63; Zn 12,87.

UV spectrum: 242, 265, 382 nm (absorption, natart on quartz), 500 nm (photoluminescence, powder, λvasb=380 nm)

IR-spectrum (tablc): 3094, 3067, 3016, 3005, 2928, 2850, 1604, 1584, 1467, 1428, 1418, 1392, 1385, 1331, 1321, 1285, 1273, 1248, 1207, 1196, 1130, 1078, 1044, 996, 977, 956, 881, 829, 829, 804, 790, 768, 734, 663, 640, 590, 540, 552, 526, 517, 444.

The presence of bands of stretching vibrations of C-H in the region 3000-3100 cm-1and bands of vibrations of double bond C=C in the field 1500-1600 cm-1confirms the presence of aromatic rings and the system of interconnected relations of the carbon-carbon bonds.

Example 4. Synthesis of bis-[8-(3,5-differentialformen)hyalinata]zinc (III)

The scheme for synthesis of:

1.92 g (0,06 M) 8-(3,5-differentialformen)quinoline (V) suspended in 25 ml of dry methanol. To this suspension at room temperature was added a solution methylalanine, obtained by dissolving 0.14 g (0,06 M) of sodium in 6 ml of methanol. The suspension was dissolved and the mixture is stirred while heated to 35-40°With 30 minutes Then to the mixture was added dropwise a solution of 0.41 g (0,003 M) of anhydrous zinc chloride in 10 ml of methanol. Formed a white precipitate. It was stirred at 35-40°C for another 1 hour, then cooled to room temperature, was filtered, washed with water, methanol, and was dried. Got a 2.01 g of compound (III). TPL 308-309°C. Yield 95% of theoretical. For further purification, the substance was recrystallized from tetrahydrofuran

Elemental analysis. Found, %: C 52,00; N 3,32; N 7,65; S 9,10. Gross formula C30H18F4N4About4S2Zn. Calculated, %: C 51,19; N 2,58; N Of 7.96; S 9,10.

UV spectrum: 265, 370 nm (absorption, natart on quartz), 465 nm (photoluminescence, powder, λvasb=380 nm).

IR-spectrum (tablc): 3075, 3043, 3924, 2853, 1606, 1587, 1504, 1468, 1439, 1384, 1327, 1294, 1276, 1245, 1209, 1195, 1144, 1123, 1084, 1047, 987, 971, 894, 971, 894, 859, 825, 796, 788, 759, 750, 678, 665, 636, 611, 596, 578, 538, 511.

The presence of bands of stretching vibrations of C-H in the region 3000-3100 cm-1and bands of vibrations of double bond C=C in the field 1500-1600 cm-1confirms the presence of aromatic rings and the system of interconnected relations of the carbon-carbon bonds.

Example 5. Electroluminescent properties of complexes II and III

For the manufacture of electroluminescent devices with structureit/HTL/EML/Al, where ITO - hole-an injecting layer, HTL - hole-transport layer, EML - electroluminescent layer and Al cathode injects layer, use a glass substrate coated with a transparent layer of a mixed oxide of indium and tin with resistance 20-25 Ohms/square. On a substrate applied a hole-transport layer composed of the MOUTH. When the MOUTH is applied by centrifuging from a solution in toluene. The thickness of the hole-transport layer 0.05-0.1 μm. Then by the evaporation of complex II and complex III, in vacuum at a temperature of approximately 350°and a base pressure of 5·10-6mm Hg is applied to the active electroluminescent layer thickness of 0.02-0.05 micron. The sample is placed in a vacuum installation VUP-4, pump out in a dynamic mode to vacuum 5·10-6mm Hg and sprayed metal electrode by evaporation of aluminum. The thickness of the metal electrode is about 0.1 μm. The area of the illuminated surface of 4-5 mm2. Received the electroluminescent device emits blue-green light when a forward voltage. The device containing II has the following parameters: brightness of 140 CD/m2is achieved at a voltage of 19 V and current density of 1.5 mA/cm2(efficiency 9 CD/A). The device containing III, characterized by the following parameters: brightness 24 CD/m2is achieved at a voltage of 20 V, the density of t is ka 19 mA/cm 2(the efficiency of 1.2 CD/A).

Thus, in the present invention results from the electroluminescent material with a high temporal resource due to the increased stability of the active luminescent layer with respect to crystallization and hydrolysis, as well as high temperature resistance of the hole-transport layer.

1. The electroluminescent material consisting of e an injecting layer, an active luminescent layer-based fluorescent substance, a hole-transport layer and an injecting hole layer, characterized in that the fluorescent substance containing the metal complexes with ligands derived 8-aminoquinoline General formula (I)

where M=Zn, n=2;

the group R1can be selected from the set:

an alkyl group of 1-4 carbon atoms, and having a normal or branched structure;

aryl group;

mono - or polyalkylene phenyl group in which the alkyl substituents consist of 1 to 4 carbon atoms and have a normal or branched structure;

mono - or polyhalogen phenyl group in which the halogen atoms are fluorine, chlorine, bromine, iodine;

R2-R7- hydrogen.

2. The electroluminescent material p is 1, characterized in that the luminescent substances it contains zinc complex of 8-(methylsulfonylamino)-quinoline (II)

3. The electroluminescent material according to claim 1, characterized in that the luminescent substances it contains zinc complex of 8-(3,5-differentsurfaces-amino)-quinoline (III)

4. The electroluminescent material according to claim 1, characterized in that as the hole-transport layer contains a mixture of oligomers of triphenylamine General formula

where n=8-9, when the molecular weight distribution of Mn=2332, Mw=3586.



 

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The invention relates to petrochemistry, specifically to the production dialkyldithiocarbamate accelerators of vulcanization of rubbers

FIELD: luminescent materials.

SUBSTANCE: invention provides novel electroluminescent material comprised of injecting layer, metal chelate complex-based active luminescent layer, hole-transition layer and hole-injecting layer. Luminescent substance is selected from oxyquinolate metallocomplexes of zinc 8-hydroxy-2-methoxyquinolate and zinc 8-hydroxy-2-methylquinolate. Electroluminescent material shows emission in green spectrum region.

EFFECT: increased heat resistance and widened choice of stable green-emitting materials.

2 cl, 3 ex

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