Scandium compounds with heterocyclic ligands and organic light-emitting diode using said compounds as emission layer

FIELD: chemistry.

SUBSTANCE: invention relates to new chemical compounds, particularly to complexes of scandium with heterocyclic ligands tris[2-(1,3-benzox(ti/imid)azol-2-yl)phenolate-O,N]scandium of general formula , where X - is oxygen, or sulphur, or NH, which can be used as an electroluminescent (emission) layer in organic light-emitting diodes (OLED). Invented also is an organic light-emitting diode, in which the emission layer is made from tris[2-(1,3-benzoxazol-2-yl)phenolate-O,N]scandium.

EFFECT: obtaining new chemical compounds which can be used as electroluminescent (emission) layer in organic light-emitting diodes (OLED).

6 cl, 3 ex

 

The invention relates to new chemical compounds, in particular complexes of scandium with heterocyclic ligands: Tris[2-(1,3-benzox(ti,imide)azole-2-yl)phenolate-O,N]scandium General formula

where X is oxygen, or sulfur, or NH, which can be used as electroluminescent (emissive) layer in organic light emitting diodes (osid).

The emission layer in acid is the environment in which directly connects to the injection into it of electron-hole pairs and the formation of light quanta.

The invention relates to the field of semiconductor optoelectronics, namely the solid-state light sources based on organic light-emitting diodes - acid or OLED - Organic Light Emitting Diodes, which are used to create flat color information screens and color of indicator devices with high consumer properties, as well as cost-effective and efficient light sources.

For the first time as an effective material of the emission layer was proposed 8- aluminum Alq3that currently is traditionally used as a reference when creating new organic light-emitting devices. As the material of the emission layer can be used both organic and integrated with the organisations of metals (for example, Polyphenylene, oksikhinolinata complexes of aluminum, zinc carboxylates of metals and other compounds). Recently, as the material of the emission layer are actively used 8-oksikhinolinata ytterbium, neodymium and erbium, which are effective infrared electroluminescent materials (see, for example, USP, t, No. 12, s-1215, 2005).

Despite considerable achievements in the field of organic light-emitting diodes, the task of search and study of new optoelectronic materials is now extremely urgent.

The closest to the essence and the achieved effect is 8-oksikhinolinata complex Scq3formula

who is the best in comparison with Alq3electroluminescent properties at a wavelength of 540 nm, which corresponds to yellow-green color (see J. Appl. Phys., 2008, 104, 053706). However, the most problematic area of development of the organic light-emitting diodes are currently emitting devices in the blue region of the spectrum. Other compounds of scandium is used as the emissive layer in acid, are not described in literature.

In the same source described organic light-emitting diode configuration ITO/TPD/Scq3/Yb, which was determined electroluminescent properties of the known compounds of scandium. The effectiveness of the known organic light-emitting diode is 2.6 LM/W at a brightness of 300 CD/m2.

Known organic light emitting diode includes a carrier substrate in the form of a glass substrate placed on the transparent layer of the anode of indium oxide doped with tin (100 nm, 20 Ohm/cm2), which is the layer of organic matter with hole conductivity - hole-transport layer (70 nm), then is radiating (emissive) layer from scandium (Scq3) (40 nm), and on top of the organic layers is a metal layer of the cathode, is made, for example, ytterbium (150 nm). The said device is taken as a prototype.

The task, which is aimed by the invention, is expanding Arsenal of chemical compounds having a high electroluminescent properties, the expansion of the range of radiation and creation on their basis of organic light-emitting diodes with high performance through the use of a new chemical substance emission layer.

This problem is solved due to the fact that the obtained new compounds of scandium with heterocyclic ligands: Tris[2-(1,3-benzox(ti, imide)azole-2-yl)phenolate-O,N] scandium General formula 1

where X is oxygen, or sulfur, or NH, is the quiet can be used as electroluminescent (emissive) layer in organic light emitting diodes (osid).

The compound obtained Tris[2-(1,3-benzoxazol-2-yl)phenolate-O,N]scandium formula 2

where X is oxygen.

The compound obtained Tris[2-(1,3-benzothiazol-2-yl)phenolate-O,N]scandium formula 3

where X is sulfur.

The obtained Tris[2-(1H-benzimidazole-2-yl)phenolate-O,N] scandium formula 4

where X is NH.

The claimed compounds are complexes with heterocyclic ligands, chelate(O,N) associated with the scandium atom. The ligand consists of two fragments - phenolic and heterocyclic, as contains a heteroatom nitrogen or oxygen, or sulfur.

The method of obtaining compounds lies in the interaction of Tris-trimethylsilane scandium with phenol, containing in ortho-position of the heterocyclic Deputy.

where X=O(1), S(2), NH(3).

The applicant was manufactured organic light-emitting diode in which the emission layer is made of new compounds, Tris[2-(1,3-benzoxazol-2-yl)phenolate-O,N]scandium (Sc(OON)3) formula 2, or Tris[2-(1,3-benzothiazol-2-yl)phenolate-O,N]scandium (Sc(SON)3) formula 3, or Tris[2-(1H-benzimidazole-2-yl)phenolate-O,N]scandium) (Sc(NON)3) formula 4. It was found experimentally that the best electroluminescent properties of a new connection Tris[2-1,3-benzoxazol-2-yl)phenolate-O,N]scandium (Sc(OOP) 3) formula 2, which, as the emission layer may be used in acid (table 1).

Table 1
ComplexEfficiency current (CD/A)The efficiency of power (LM/W)Operating voltage (In)
Sc(OON)36.64.44.7
Sc(SON)33.11.66.0
Sc(NON)30.0050.0019.7

This problem can be solved due to the fact that the organic light-emitting diode containing a carrier substrate in the form of a substrate placed on the transparent layer of the anode contains at least an organic emitting (emissive) layer, which is made on the basis of the compounds of scandium, on top of which is a metal cathode, is made, for example, the R, from ytterbium, according to the claimed invention, the emissive layer is made of Tris[2-(1,3-benzoxazol-2-yl)phenolate-O,N]scandium formula 2

Preferably, the presence in the device layer of an organic substance with hole conductivity (hole-transport layer located on the anode, whose role is to facilitate the transfer of holes from the anode to the emission layer. As a material for the hole-transport layer are compounds with p-type conductivity, for example N,N'-bis(3-were)-N,N'-diphenylbenzidine.

Preferably, the device layer with electronic conductivity (electron transport layer)located below the cathode layer, which facilitates the injection box electrons in the emissive layer and often combines the function of the emission layer. As a material of the electron-transport layer use compounds with electronic conductivity. In this case, use the new connection Tris[2-(1,3-benzoxazol-2-yl)phenolate-O,N]scandium, which has good electronic conductivity

As the supporting framework can be used glass or plastic substrate. Glass substrate placed on them by a layer of anode material which is traditionally indium oxide doped with tin, release the camping industry. In the inventive device uses the above-mentioned substrate. At the same time as the anode material can be used other compounds with high injection holes (for example, transparent oxides of gallium and zinc, titanium nitride and gallium, and others). Electroluminescent (emissive) layer is the environment in which be connected directly injected into him electron-hole pairs and the formation of light quanta. The thickness of the emission layer is 30-50 nm.

It was found experimentally that the use of the emission layer is made of Tris[2-(1,3-benzoxazol-2-yl)phenolate-O,N]scandium improves the operating characteristics of the device compared to the prototype.

The applicant was manufactured organic light-emitting diode in which the emission layer is made of Tris[2-(1,3-benzoxazol-2-yl)phenolate-O,N]scandium and, for comparison, from 8- scandium Scq3and defined their characteristics (table 2).

Table 2
ComplexEfficiency current (CD/A)The efficiency of power (LM/W)Operating voltage (In)λ emission (nm)
Scq34.62.65.5540
Sc(OON)36.64.44.7435

Table 2 shows that when using the device with an emission layer made of Tris[2-(1,3-benzoxazol-2-yl)phenolate-O,N] scandium, in comparison with the prototype, in which the said layer is made from Scq3the effectiveness of the current increases from 4.6 to 6.6 CD/A, the efficiency of power increases from 2.6 to 4.4 LM/W, the wavelength is changed from 540 435 nm radiation corresponding to the blue color, and the working voltage when the brightness 300 CD/m2corresponding to the brightness of the running monitor, decreases from 5.5 to 4.7 Century the Improved performance when using the emission layer of the new compounds of scandium can be explained, apparently, by the properties of the chelate structure of the complexes of scandium with heterocyclic ligands. Theoretical approaches do not allow to predict the observed effect, i.e. the result is not obvious to solve the task and is not obvious from the prior art.

Example 1. Tris[2-(1,3-benzoxazol-2-yl)phenolate-O,N] scandium

To 1 mmole titrimetrically scandium SC[N(Si 3)2]3in 20 ml of tetrahydrofuran was added 3 mmole of 2-(1,3-benzoxazol-2-yl)phenol in 10 ml of tetrahydrofuran under stirring for 30 minutes. The reaction mixture is stirred for further 30 minutes at room temperature, then the solvent and volatile reaction products are removed in vacuum. The solid residue amide washed with toluene and recrystallization from dimethylformamide produce the target product in the form of colorless crystals with MP. 320°C. Calculated: C39H24N3O6SC: 69.34, H 3.58, N 6.22, Sc 6.65. Found: S, H 3.62, N 6.26, Sc 6.71. IR spectrum (liquid paraffin, cm-1): 3050 (PL), 1607 (cf), 1558 (CL), 1523 (cf), 1331 (CL), 1284 (CL), 1257 (cf), 1155 (CL), 1057 (CL), 869 (cf), 802 (cf), 740 (s), 615 (cf).1H NMR, Py-d5, δ, ppm: 6.68 (1H, d, C(6)-H), 6.85 (1H, t, (4)-H), 6.98-7.76 (m, CAr-H), 7.97-8.02 (2H, mAr-N).

Example 2. Tris[2-(1,3-benzothiazol-2-yl)phenolate-O,N] scandium

To 1 mmole of Tris-trimethylsilyl scandium SC[N(Si3)2]3in 20 ml of tetrahydrofuran was added 3 mmole of 2-(1,3-benzothiazol-2-yl)phenol in 10 ml of tetrahydrofuran under stirring for 30 minutes. The reaction mixture is stirred for further 30 minutes at room temperature, then the solvent and volatile reaction products are removed in vacuum. The solid residue is washed with toluene and recrystallization from dimethylformamide produce the target product in the form of bescot the x crystals with MP. >350°C. Calculated: C39H24N3O3S3SC: 64.72, H 3.34, N 5.81, S 13.29, Sc 6.21. Found: 64.78, H 3.41, N 5.89, S 13.33, Sc 6.27. IR spectrum (liquid paraffin, cm-1): 3050 (PL), 1597 (s), 1554 (cf), 1335 (cf), 1318 (cf), 1263 (CL), 1216 (CL), 1156 (CL), 970 (CL), 878 (cf), 842 (cf), 750 (s), 724 (s), 616 (cf).1H NMR, Py-d5, δ, ppm: 6.99 (1H, t, (4)-H), 7.28-7.49 (m, CAr-H), 8.02-8.10 (2H, mAr-H).

Example 3. Tris[2-(1H-benzimidazole-2-yl)phenolate-O,N] scandium

To 1 mmole of Tris-trimethylsilyl scandium SC[N(Si3)2]3in 20 ml of tetrahydrofuran was added 3 mmole of 2-(1H-benzimidazole-2-yl)phenol in 10 ml of tetrahydrofuran under stirring for 30 minutes. The reaction mixture is stirred for further 30 minutes at room temperature, then the solvent and volatile reaction products are removed in vacuum. The solid residue is washed with toluene and recrystallization from dimethylformamide produce the target product in the form of colorless crystals with MP. >350°C. Calculated: C39H27N6O3Sc: 69.64, H 4.05, N 12.49, Sc 6.68. Found: 69.69, H 4.15, N 12.43, Sc 6.62. IR spectrum (liquid paraffin, cm-1): 3170 (CL), 3050 (PL), 1623 (cf), 1600 (cf), 1560 (cf), 1527 (cf), 1311 (cf), 1265 (cf), 1130 (CL), 1038 (CL), 965 (CL), 915 (CL), 850 (s), 803 (cf), 738 (s), 615 (cf).1H NMR,

Py-d5, δ, ppm: 6.70-6.80 (2H, m, CAr-H), 7.06-7.34 (m, CAr-H), 8.13-8.20 (2H, mAr-H), 8.60 (1H, d, CAr-H), 13.2(1H, NH).

The drawing shows the body of the static light-emitting diode, containing a carrier substrate in the form of a glass substrate 1 is placed on the transparent layer of the anode 2 - source holes, made of indium oxide doped with tin. At the anode is a layer of organic matter with hole conductivity 3 - conductor layer holes, made of N,N'-bis(3-were-N,N'-diphenylbenzidine thickness of 20 nm. Then follow the emitting layer (emitter layer) 4 made of Tris[2-(1,3-benzoxazol-2-yl)phenolate-O,N]scandium, which is a medium, which directly be connected to the injection into it of electron-hole pairs and the formation of light quanta. The said layer at the same time performs the function of electron transport layer 5. On top of the organic layers is a layer of the cathode 6 is an electron source made of ytterbium.

The thickness of the emission and cathode layers 50 and 200 nm, respectively.

The device operates as follows. When the supply voltage minus to the cathode 6, and a plus to the anode 2 of them injections, respectively, electrons and holes, i.e. negative and positive charges. In sluchayem layer 4 recombination of these charges, which causes the effect of electroluminescence (light emission). As of the support base 1 of the device used a commercially available glass substrate placed on it n acronym layer of indium oxide, doped tin functioning as the anode. To obtain the organic film material layers making up the structure of the claimed acid layer and the cathode, used the method of thermal evaporation in vacuum.

The inventive device is used as an emission layer of the new compounds of scandium, belonging to the class of emission compounds in a blue wavelength range, is characterized by high technical characteristics: the effectiveness of current and power is 6.6 CD/a and 4,4 LM/W, respectively, the operating voltage when the brightness of 150 CD/m2that corresponds to the brightness of the running monitor 4,5 Century With said operating voltage drop the brightness by 10% is not less than 4000 hours.

The effectiveness of the inventive organic light-emitting diode is 4.4 LM/W at a brightness of 300 CD/m2.

Creating a new material expands its Arsenal of chemical compounds having a high electroluminescent and elektronoprovodyaschie properties that can be used as an emissive layer in an organic light-emitting diodes to improve their performance.

1. Compounds of scandium with heterocyclic ligands Tris[2-(1,3-benzox(ti/imide)azole-2-yl)phenolate-O,N]scandium General formula

where X is oxygen, or sulfur, or NH, which is s can be used as electroluminescent (emissive) layer in organic light emitting diodes (osid).

2. The compound according to claim 1, which is a Tris[2-(1,3-benzoxazol-2-yl)phenolate-O,N]scandium, formulas

where X is oxygen.

3. Organic light-emitting diode containing a carrier substrate in the form of a substrate placed on the transparent layer of the anode, which is at least radiant (emissive) layer based on organic compounds of scandium, on top of the emitting layer is a metal cathode, made from, for example, ytterbium, characterized in that the emission layer is made of Tris[2-(1,3-benzoxazol-2-yl)phenolate-O,N]scandium.

4. Organic light-emitting diode according to claim 3, characterized in that it contains a layer of organic matter with hole conductivity (hole-transport layer)made of N,N'-bis(3-were)-N,N'-diphenylbenzidine located on the anode layer.

5. Organic light-emitting diode according to claim 3, characterized in that it contains a layer of organic matter with electronic conductivity (electron transport layer), made of Tris[2-(1,3-benzoxazol-2-yl)phenolate-O,N]scandium, located under the cathode layer.

6. Organic light-emitting diode according to claim 3, characterized in that the layer of the anode is made of indium oxide doped with tin.



 

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