CN113224247A - Pyridine-3, 5-dinitrile-based electroluminescent material and application thereof in organic light-emitting device - Google Patents

Pyridine-3, 5-dinitrile-based electroluminescent material and application thereof in organic light-emitting device Download PDF

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CN113224247A
CN113224247A CN202110188558.7A CN202110188558A CN113224247A CN 113224247 A CN113224247 A CN 113224247A CN 202110188558 A CN202110188558 A CN 202110188558A CN 113224247 A CN113224247 A CN 113224247A
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light
emitting
compound
emitting layer
light emitting
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李晓常
许千千
坪山明
殷正凯
上野和則
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Jiangxin Guanmat Optoelectronic Materials Co ltd
Guanmat Optoelectronic Materials Shenzhen Co ltd
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Guanmat Optoelectronic Materials Shenzhen Co ltd
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Abstract

The present invention provides an organic light emitting device having a very high purity of light emission hue, high light emitting efficiency, and improved lifetime, the organic light emitting device comprising a multi-layered structure of an anode and a cathode, a hole injection layer, an emission layer, an electron layer, etc., wherein the emission layer comprises a light emitting compound (formula 1).
Figure RE-DEST_PATH_IMAGE001

Description

Pyridine-3, 5-dinitrile-based electroluminescent material and application thereof in organic light-emitting device
Technical Field
The invention relates to an organic electroluminescent material and a device, in particular to a light-emitting device formed by a reverse intersystem crossing thermal activation delay RISC light-emitting material and an organic semiconductor light-emitting compound thereof under the driving of an electric field.
Background
An organic electroluminescent device (OLED) comprises a pair of electrodes forming an anode and a cathode, and one or more layers of material consisting of a hole injection layer, an emissive layer, an electron transport layer and some other charge layer, wherein the emissive layer consists of a light-emitting compound dopant and a host material.
A conventional organic electroluminescent device (OLED) is a simple-structured device having a dopant of a fluorescent light emitting material, and the maximum internal quantum yield of such a fluorescent light emitting OLED is widely considered to be theoretically limited to within 25%, and it is often defined that the fluorescent light emitting material is a first generation light emitting material, and a light emitting device composed thereof is referred to as a first generation OLED.
As a second generation light emitting material, a phosphorescent material improves quantum yield by using a triplet state, and is proved to be a light emitting material dopant for widespread use in OLEDs. Phosphorescent dopants are essentially noble metal complexes which cause metal-d orbital interactions with theoretical internal quantum efficiencies up to 100% (appl. phys. lett., 1999,75, 4-6.). However, phosphorescent metal complex materials using iridium metal and rare metal are expensive, and have a problem of production cost. In addition, design flexibility of phosphorescent emission color is also limited due to ligand structure dependence of the complex, and the iridium complex is not necessarily thermally stable.
TADF (Thermally activated delayed fluorescence) materials, as third-generation organic light emitting materials, have been widely focused on the characteristic that they can theoretically achieve 100% of maximum exciton utilization rate, because they can participate in electroluminescence by using triplet excitons through the Reverse inter-system conversion (RISC) (US 7034454, JP 3848306, JP 3848307) process, and have become a hot spot of research.
T of TADF Material1Sufficiently close to S1And T is1Energy level below S1And allows T to be shifted by thermally activated reverse inter-system cross-over RISC1Conversion of excitons to radiated S1Excitons (appl. phys. lett., 2012,101, 093306), therefore, the theoretical internal quantum efficiency of TADF can reach 100%.
Compared with the traditional fluorescent material (the first generation organic luminescent material), the TADF material has higher electroluminescent efficiency due to the realization of 100% internal quantum efficiency; on the other hand, TADF materials have significant cost and stability advantages over metal complex phosphorescent materials because rare precious metals are not required.
Pyridine-3, 5-dinitrile and 1,3, 5-triazine have similar electroabsorption properties, and the cyano groups at the 3 and 5 positions have larger steric hindrance than the nitrogen atom of triazine, so that a donor connected with the pyridine-3, 5-dinitrile can generate a twist angle and thus the performance of the TADF material is more favorable, however, only a few TADF materials based on pyridine-3, 5-dinitrile are reported so far (J.Mater.chem.,2012,22, 8922; J.Mater.chem.C,2018,6, 6543; J.Phys.chem.Lett.2019,10,2669; CN 109912564A), and the performances such as efficiency and color scale are far inferior to the reported optimal performance of the TADF based on 1,3, 5-triazine.
Disclosure of Invention
The present invention addresses the above-described deficiencies of the prior art by disclosing an organic light emitting material and light emitting device therefrom, the disclosure of which provides an organic light emitting device application comprising an anode, a cathode and an organic light emitting layer sandwiched therebetween of at least one light emitting compound molecule as described herein, whereby a "sandwich-like" organic light emitting device constructed therefrom is capable of achieving device performance improvement with thermally activated reverse channeling RISC fluorescence, thereby providing an alternative to existing blue fluorescent materials (first generation organic light emitting materials), or achieving high luminous efficiency similar to existing organic phosphorescent light emitting materials but avoiding the use of expensive metals. The organic light emitting device can emit a light emitting hue with very high purity and realize light emission of high luminance with high light emitting efficiency and a sufficiently long life, and also provides an organic light emitting device produced at low cost because of the absence of precious metals.
First, an organic electroluminescent diode device includes
a) An anode,
b) A cathode,
c) The anode and the cathode comprise a plurality of organic layers, the plurality of organic layers comprise a light-emitting layer, and the light-emitting layer provides light emission through charge injection and effective transition; the transition being from the singlet state S1Transition to ground state S0And triplet state T1Transition to S by thermal activation1Then transited to the ground state S0Fluorescence is generated.
In the above organic light emitting device, a pair of electrodes forming an anode and a cathode, and a multilayer structure device including a hole injection layer, a transport layer, an emission layer, an electron injection layer, a transport layer, and the like are included, wherein the emission layer or the emission layer is composed of one or two kinds of host materials and a light emitting material compound, and the light emitting material compound accounts for 1 to 45% by mole in the emission layer.
The organic electroluminescent diode device according to which the light emitting material in the light emitting layer has a T calculated from Gauss1And S1The energy gap between them is less than 0.3 eV.
The organic electroluminescent diode device according to the present invention is characterized in that the light emitting material compound in the light emitting layer is represented by the following formula 1.
Figure RE-GDA0003112053430000021
Wherein all or part of the hydrogens on R selected from the group consisting of alkyl, alkoxy, alkyl and aryl may be replaced by deuterium;
ar is selected from aromatic rings, wherein the aromatic rings are monocyclic, fused aromatic rings and fused heterocyclic aromatic rings, such as phenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, pyridyl, indolyl, quinolinyl, isoquinolinyl, acridinyl, phenazinyl and phenanthridinyl; all or part of the hydrogens on Ar may be replaced with deuterium;
q is selected from the group consisting of aromatic amines, fused heterocyclic aromatic amines, carbazoles, phenazines, phenoxazines, phenothiazines, dihydroacridines, benzothiophenes, dibenzothiophenes, benzofurans, dibenzofurans, benzothiazoles, benzoxazoles, and substituted aryls selected from the group consisting of aromatic amines, fused heterocyclic aromatic amines, carbazoles, phenazines, phenoxazines, phenothiazines, dihydroacridines, benzothiophenes, dibenzothiophenes, benzofurans, dibenzofurans, benzothiazoles, benzoxazoles; q is bonded with the substituted benzene ring through a C-C bond or a C-N bond;
all or part of the hydrogens of the compound defined by formula 1 may be replaced with deuterium.
For ease of understanding, some typical compounds are given below, and exemplary compounds include, but are not limited to, the following:
Figure RE-GDA0003112053430000022
Figure RE-GDA0003112053430000031
Figure RE-GDA0003112053430000041
Figure RE-GDA0003112053430000051
Figure RE-GDA0003112053430000061
the organic light emitting device application of the material of the present invention is described in detail below. The organic light emitting device of the present invention is an organic light emitting device having at least one pair of electrodes, wherein at least one electrode comprises a transparent or translucent anode or cathode, and one or more layers containing an organic compound are between the electrodes (anode and cathode), wherein at least one of the layers contains an organic compound selected from the compounds represented by formula 1. Preferred examples of the organic light-emitting device of the present invention are shown in fig. 1 and 2.
In fact, the OLED device shown comprises the following functional layers:
1: base material 101
2: the substrate is covered with a conductive indium tin oxide coating ITO anode 101
3: luminescent layer 104
4: conductive cathode 107
5: hole transport layer 103
6: electron transport layer 105
7: electron injection layer 106
8: hole injection layer 102
9: possible hole blocking layer
10: possible electron blocking layer
Fig. 1 is a sectional view showing an example of an organic light emitting device of the present invention. Obviously, the luminous color can be adjusted by designing and selecting different luminous compounds of the invention to adjust the energy band of the luminous compound of the luminous layer. Therefore, according to the organic light emitting device, the light emitting device is characterized in that the light emitting device is blue light with a wavelength of 440-500nm, or green light with a wavelength of 510-545nm, or yellow light with a wavelength of 550-580nm, or red light with a wavelength of 590-640 nm. On the other hand, the luminescent compound can also be used as an auxiliary main body material, the usage amount is 5-20% by weight, the luminescent compound is used as a sensitizer to act, excitons (including singlet states and triplet states) generated by the main body material are collected, the host material does not emit light and transfers the excitons to a luminescent dopant, and the performance of a device is improved.
Drawings
Fig. 1 shows a cross-sectional view of an example of an organic light emitting device of the present invention:
FIG. 2 is a graph showing an ultraviolet-fluorescence spectrum of an organic luminescent compound 1 according to the present invention
FIG. 3 shows the OLED electroluminescence spectrum of the organic luminescent compound 1 of the present invention as a luminescent material (EL 450 nm; CIEx 0.15; y 0.10)
Detailed Description
In order to make the aforementioned objects, features and advantages of the present invention comprehensible, specific embodiments accompanied with examples are described in detail below. In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention. The invention can be implemented in many ways other than those described herein and similar generalizations can be made by those skilled in the art without departing from the spirit of the invention. Therefore, the invention is not limited to the specific embodiments disclosed below.
Example 1: synthesis of exemplary compound 1:
Figure RE-GDA0003112053430000071
acetic anhydride (23.9mL,0.255mol) was added dropwise to a solution of (I) (30.3g, 0.25mol) in glacial acetic acid (400 mL). The mixture was stirred to cool to room temperature. A glacial acetic acid solution containing bromine (40.75g, 0.255mol) was added dropwise to the above mixture, and the mixture gradually thickened. After the dropwise addition, the reaction was continued for 30min, and then the reaction solution was poured into 500g of ice, filtered, washed with water, and dried to obtain 53.2g of a white granular product (II) with a yield of 88%.
Compound (II) (85g) and NaOH (52g) were dissolved in 200mL of 57% ethanol solution to give a yellow solution, which was reacted at 80 ℃ under reflux for 6h, cooled to room temperature, diluted with 400mL of water, stirred at room temperature for two more hours, filtered, and dried under vacuum to give compound (III) in 80% yield.
225g of crushed ice, 90mL of concentrated hydrochloric acid and (III) (40.4g, 0.09mol) were added to a large beaker and slowly added dropwise with stirringNaNO2(15.1g, 0.097mol) in water (50mL) and the reaction temperature was kept below 5 ℃ during the addition. After the addition was completed, stirring was continued for 15min, and then an aqueous solution (120 mL) of KI (16g, 0.096mol) was slowly added dropwise to the reaction solution, the color of the solution immediately changed from yellow to brown, and the volume rapidly expanded. After the dropwise addition, the reaction was continued for 30min, then a saturated aqueous solution of sodium thiosulfate was added to the reaction solution, extraction was carried out three times with dichloromethane, the organic phases were combined, spin-dried, and silica gel column Purification (PE) was carried out to obtain an oily product (IV) with a yield of 70%.
Compound (IV) (10.0g, 32.15mmol), carbazole (5.37g, 32.15mmol), copper powder (2.47g, 38.59mmol), potassium carbonate (13.31g, 96.46mmol) and 100DMF were added in this order to the flask, replaced with nitrogen three times, and then reacted at 130 ℃ for 24 hours under nitrogen protection. After completion of the reaction, 200mL of dichloromethane was added to the reaction solution, and the mixture was filtered through celite to remove insoluble impurities, dichloromethane was removed under reduced pressure, the remaining solution was poured into water, and the filtrate was purified by silica gel column chromatography (PE/DCM ═ 10/1) to obtain a crude product, which was dissolved in dichloromethane and back-precipitated with methanol to obtain 6.3g of the compound (V) as a white solid with a yield of 56%.
Compound (V) (4.8g, 13.7mmol) was dissolved in 30mL of anhydrous THF, cooled to-78 deg.C under nitrogen, and n-butyllithium (6mL, 15.1mmol) was added dropwise slowly with stirring. After the addition was complete, the reaction was continued at this temperature for 1 hour, and then anhydrous DMF (3.0g, 41.1mmol) was slowly added dropwise. After the dropwise addition, the temperature is kept for reaction for 30min, then the reaction solution is heated to room temperature and continuously reacted for 2 hours, then 1N hydrochloric acid (50mL) is added into the reaction solution, dichloromethane is used for extraction, spin-drying is carried out, and silica gel column purification is carried out to obtain a light yellow compound (VI) with the yield of 72%.
To a reaction flask were added compound (VI) (2.6g, 8.7mmol), phenylacetonitrile (2.78g, 19.1mmol), ammonium acetate (6.7g, 87mmol) and 50mL of acetic acid in this order, and reacted under reflux for 16 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, 300mL of dichloromethane was added to the reaction mixture, acetic acid and water-soluble substances were removed by washing with water, the organic phase was dried by spinning, and the reaction mixture was recrystallized from 150mL of toluene to obtain a pale yellow solid (VII) in a yield of 85%.
Compound (VII) (3.6g, 6.5mmol) was dissolved in 30mL of dichloromethane, DDQ (1.77g, 7.8mmol) was added to the solution, and the reaction was completed after stirring at room temperature for 6 hours. Then, 300mL of methylene chloride was added to the reaction mixture, and the mixture was washed with water to remove the water-soluble substance, and the organic phase was spin-dried, slurried with methanol, and filtered to obtain the objective compound 1 as a white solid with a yield of 80%. Fig. 2 is a graph of uv-fluorescence spectrum (PL 449in film) of organic luminescent compound 1(BD175) according to the present invention.
Example 2: synthetic preparation of other compounds:
similarly, according to the above synthetic chemistry principle and general organic multistep reaction basic principle, the following organic semiconductor material compounds were synthesized, and the molecular weights and fragments of the molecules were verified by mass spectrometry, which is specifically summarized in table 1 below, without departing from the scope of the present invention:
table 1: compound synthesis and characterization
Figure RE-GDA0003112053430000081
Figure RE-GDA0003112053430000091
Figure RE-GDA0003112053430000101
Example 3. in an example of an OLED device application:
at a background vacuum of 10-5In multi-source evaporation OLED preparation equipment of Pa, the following device structure is adopted: ITO/3% HATCN: mTDATA
Figure RE-GDA0003112053430000103
/TcTa
Figure RE-GDA0003112053430000104
5% luminescent dopant/Host
Figure RE-GDA0003112053430000105
/ET
Figure RE-GDA0003112053430000106
/LiF
Figure RE-GDA0003112053430000107
Figure RE-GDA0003112053430000108
Al, different host materials were used for comparison with the light-emitting material OLED light-emitting device. Blue OLEDs use BH: BD (5%) light emitting material, green OLED using GH: BH (1:1 mixing ratio): a light emitting dopant. The vacuum deposition rates of the organic layers and the electrodes are shown in Table 3.
Table 3: OLED device preparation condition (doping wt concentration in light-emitting layer 9%)
Figure RE-GDA0003112053430000102
Figure RE-GDA0003112053430000111
The known or common materials used in the experiments are as follows in table 4:
Figure RE-GDA0003112053430000112
the performance of the manufactured OLED device after inspection and the comparison results are summarized in table 5 below.
Table 5: OLED device Performance (@10mA/cm2)
Figure RE-GDA0003112053430000113
Compared with the reference device B0 using the common electro-fluorescent luminescent doping material BD, the OLED luminescent devices B1, B2 and B3 made by the blue luminescent compounds 1, 10 and 18 of the invention have the effects of reducing the working voltage and improving the current luminescent efficiency. FIG. 3 is a compoundThe substance 1 is used as a luminescent doping material OLED at 300Cd/m2EL emission spectrum of time. Similarly, the comparative reference device G0 used a common electro-phosphorescent dopant material Ir (mppy)3The large-scale OLED light-emitting devices G1, G2 and G3 made of the green light-emitting compounds 4, 8 and 14 show the effects of reducing the working voltage and improving the current light-emitting efficiency. The compound 40 used as an auxiliary main body material can be used as a traditional blue-light OLED sensitizer to improve the efficiency of the blue-light emitting material BD, and the service life of the blue-light emitting material BD can be prolonged.
The foregoing is merely a preferred embodiment of the invention and is not intended to limit the invention in any manner. Those skilled in the art can make numerous possible variations and modifications to the disclosed embodiments, or modify equivalent embodiments, without departing from the scope of the invention, using the teachings disclosed above. Therefore, any simple modification, equivalent change and modification made to the above embodiments according to the technical essence of the present invention are still within the protection scope of the technical solution of the present invention, unless the content of the technical solution of the present invention is departed from.

Claims (7)

1. An organic electroluminescent diode device comprises
a) An anode,
b) A cathode,
c) The anode and the cathode comprise a plurality of organic layers, the plurality of organic layers comprise a light-emitting layer, and the light-emitting layer provides light emission through charge injection and effective transition; the transition being from the singlet state S1Transition to ground state S0And triplet state T1Transition to S by thermal activation1Then transited to the ground state S0Fluorescence is generated.
2. The device of claim 1, wherein the light-emitting layer comprises one or two of a host material and a compound of a light-emitting material, and the molar ratio of the light-emitting material is 1-45%.
3. The organic electroluminescent diode device according to claim 1, wherein the light-emitting material in the light-emitting layer has a T calculated from Gauss1And S1The energy gap between them is less than 0.3 eV.
4. The light-emitting element according to claims 1, 2 and 3, wherein the light-emitting material compound in the light-emitting layer is represented by the following formula 1.
Figure RE-FDA0003028478270000011
Wherein
All or part of the hydrogens on the groups selected from alkyl, alkoxy, alkyl and aryl may be replaced by deuterium;
ar is selected from aromatic rings, wherein the aromatic rings are monocyclic, fused aromatic rings and fused heterocyclic aromatic rings, such as phenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, pyridyl, indolyl, quinolinyl, isoquinolinyl, acridinyl, phenazinyl and phenanthridinyl; all or part of the hydrogens on Ar may be replaced with deuterium;
q is selected from the group consisting of aromatic amines, fused heterocyclic aromatic amines, carbazoles, phenazines, phenoxazines, phenothiazines, dihydroacridines, benzothiophenes, dibenzothiophenes, benzofurans, dibenzofurans, benzothiazoles, benzoxazoles, and substituted aryls selected from the group consisting of aromatic amines, fused heterocyclic aromatic amines, carbazoles, phenazines, phenoxazines, phenothiazines, dihydroacridines, benzothiophenes, dibenzothiophenes, benzofurans, dibenzofurans, benzothiazoles, benzoxazoles; q is bonded with the substituted benzene ring through a C-C bond or a C-N bond;
all or part of the hydrogens of the compound defined by formula 1 may be replaced with deuterium.
5. The light-emitting material compound in the light-emitting layer according to claim 4 includes the following exemplary compounds:
Figure RE-FDA0003028478270000021
Figure RE-FDA0003028478270000031
Figure RE-FDA0003028478270000041
Figure RE-FDA0003028478270000051
6. the device as claimed in claim 1 to 5, wherein the light-emitting device is visible light with a wavelength of 440-640 nm.
7. The organic light-emitting device of claims 1, 2, 3, 4, and 5, wherein the light-emitting material compound in the light-emitting layer can be used as an auxiliary host material of the light-emitting layer and as a sensitizer material to improve the light-emitting performance of the device.
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