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CN111217713A - Luminescent material and application thereof - Google Patents

Luminescent material and application thereof Download PDF

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CN111217713A
CN111217713A CN201811417168.7A CN201811417168A CN111217713A CN 111217713 A CN111217713 A CN 111217713A CN 201811417168 A CN201811417168 A CN 201811417168A CN 111217713 A CN111217713 A CN 111217713A
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黄金华
曾礼昌
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Beijing Eternal Material Technology Co Ltd
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Abstract

The invention discloses a novel organic compound, which has a structure shown in the following formula (I):
Figure DDA0001879749020000011
wherein: ar (Ar)1、Ar2、Ar3And Ar4Each independently selected from substituted or unsubstituted C6‑C30Aryl, substituted or unsubstituted C6‑C30A condensed aryl group of (A), a substituted or unsubstituted C3‑C30One of the heteroaryl groups of (a); l is1、L2、L3And L4Each independently selected from the group consisting of a single bond, substituted or unsubstituted C6‑C30Arylene of (a), substituted or unsubstituted C6‑C30Heteroarylene group of (1), substituted or unsubstituted C6‑C30One of the fused arylene groups of (a); and L as mentioned above1‑Ar1、L2‑Ar2、L3‑Ar3And L4‑Ar4The same substituent groups are not simultaneously selected; the compound of the invention shows excellent device performance and stability when used as a hole transport material in an OLED device. The invention also protects the organic electroluminescent device adopting the compound with the general formula.

Description

Luminescent material and application thereof
Technical Field
The invention relates to a novel organic compound, in particular to a compound for an organic electroluminescent device and application of the compound in the organic electroluminescent device.
Background
Organic Light Emission Diodes (OLED) devices are a kind of devices with sandwich-like structure, which includes positive and negative electrode films and Organic functional material layers sandwiched between the electrode films. And applying voltage to the electrodes of the OLED device, injecting positive charges from the positive electrode and injecting negative charges from the negative electrode, and transferring the positive charges and the negative charges in the organic layer under the action of an electric field to meet for composite luminescence. Because the OLED device has the advantages of high brightness, fast response, wide viewing angle, simple process, flexibility and the like, the OLED device is concerned in the field of novel display technology and novel illumination technology. At present, the technology is widely applied to display panels of products such as novel lighting lamps, smart phones and tablet computers, and further expands the application field of large-size display products such as televisions, and is a novel display technology with fast development and high technical requirements.
With the continuous advance of OLEDs in both lighting and display areas, much attention has been paid to the research on their core materials. This is because an efficient, long-lived OLED device is generally the result of an optimized configuration of the device structure and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures. Common functionalized organic materials are: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light emitting host materials and light emitting objects (dyes), and the like.
In order to prepare an OLED light-emitting device with lower driving voltage, better light-emitting efficiency and longer service life, the performance of the OLED device is continuously improved, the structure and the manufacturing process of the OLED device need to be innovated, and photoelectric functional materials in the OLED device need to be continuously researched and innovated, so that functional materials with higher performance can be prepared. Based on this, the OLED material industry has been working on developing new organic electroluminescent materials to achieve low starting voltage, high luminous efficiency and better lifetime of the device.
So far, the development of the existing OLED photoelectric functional material is far behind the requirements of panel manufacturing enterprises on the OLED material, so it is very urgent to develop an organic functional material with better performance to meet the development requirements of the current industry.
An organic electroluminescent material used as a transport material to solve the problems of luminous efficiency, thermal stability and lifetime is reported in korean patent application KR1020140096227A, which has the following general formula:
Figure BDA0001879749010000021
in this patent document, it is further preferable that the binaphthyl compound in which the naphthalene α and α ' positions are connected defines that the diarylamine groups are connected to the 3,3 ' positions, 4 ' positions, 4,5 ' positions, 4,6 ' positions, 4,7 ' positions, 5,3 ' positions, 5,6 ' positions, 5,7 ' positions, 6,3 ' positions, 6,7 ' positions, 7,3 ' positions, and 8,8 ' positions of the naphthalene ring in the general formula, but the binaphthyl compound in which the diarylamine groups are connected to the naphthalene α and α ' positions in the 2,2 ' positions is not involved.
An organic electroluminescent material is reported in US20040106003, emphasizing that aryl compounds are introduced at the 2, 2' position. This patent relates to the following two symmetric compounds H-1 and H-2 having exactly the same substitution on the N atom, but does not relate to asymmetric compounds having not exactly the same substitution on the N atom.
Figure BDA0001879749010000022
An organic electroluminescent material is reported in the patent JP 2003040867a, which emphasizes that a carbazole derivative is introduced at the 2, 2' position, but does not relate to a diarylamine-based compound in which the 2 position is linked by a ring opening.
However, there is still room for improvement in the luminescence property of the conventional organic electroluminescent materials, and there is a need for development of new organic electroluminescent materials.
Disclosure of Invention
in order to solve the technical problems, the invention provides a synthesis method of a novel binaphthyl compound connected at alpha, alpha' positions of naphthalene and an application of the binaphthyl compound in an OLED device.
the novel naphthalene α, α' -linked binaphthyl compound of the present invention has a specific general formula shown in formula (I):
Figure BDA0001879749010000031
wherein:
Ar1、Ar2、Ar3and Ar4Each independently selected from substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C6-C30A condensed aryl group of (A), a substituted or unsubstituted C3-C30One of the heteroaryl groups of (a);
L1、L2、L3and L4Each independently selected from the group consisting of a single bond, substituted or unsubstituted C6-C30Arylene of (a), substituted or unsubstituted C6-C30Heteroarylene group of (1), substituted or unsubstituted C6-C30One of the fused arylene groups of (a);
and L as mentioned above1-Ar1、L2-Ar2、L3-Ar3And L4-Ar4The same substituent groups are not simultaneously selected;
further, L1、L2、L3And L4Preferably a single bond.
R1、R2Each independently selected from H, halogen atom, C1-C20Alkoxy, cyclic or acyclic C of1-C20Alkyl, cyano, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C6-C30A condensed aryl group of (A), a substituted or unsubstituted C3-C30One of the heteroaryl groups of (a);
m and n are each independently selected from integers from 0 to 6;
when the above groups have substituents, the substituents are respectively and independently selected from halogen and C1-C10Alkyl or cycloalkyl of, C2-C10Alkenyl radical, C1-C6Alkoxy or thioalkoxy group of (C)6-C30Monocyclic aromatic hydrocarbon or condensed ring aromatic hydrocarbon group of (A), C3-C30One of the monocyclic heteroaromatic group or the condensed ring heteroaromatic group of (a).
Further, Ar1And Ar4Each independently preferably has the following structure of formula (a):
Figure BDA0001879749010000032
Figure BDA0001879749010000041
in the formula (A): x is selected from CR3R4、NR5O or S;
R3to R6Each independently selected from H, C with or without ring formation1-C20Alkyl, cyano, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C6-C30A condensed aryl group of (A), a substituted or unsubstituted C3-C30One of the heteroaryl groups of (a); and R is3And R4Can be connected into a ring;
p is an integer of 0 to 7;
L5selected from single bond, substituted or unsubstituted C6-C30Arylene of (a), substituted or unsubstituted C6-C30The heteroarylene group of (1) is more preferably a single bond.
Further, Ar1、Ar2、Ar3And Ar4Each independently preferably has the structure of formula (A) and Ar1、Ar2、Ar3And Ar4Are different from each other.
Further preferably, R in the above general formula (I) of the present invention1、R2Each independently selected from H, halogen atom, cyano, C1-C10Alkoxy, cyclic or acyclic C of1-C10One of the alkyl groups of (1).
The compounds of the general formula (I) according to the invention can be preferably those of the following specific structures: P1-P162, these compounds being representative only:
Figure BDA0001879749010000042
Figure BDA0001879749010000051
Figure BDA0001879749010000061
Figure BDA0001879749010000071
Figure BDA0001879749010000081
Figure BDA0001879749010000091
Figure BDA0001879749010000101
Figure BDA0001879749010000111
the naphthalene α, α' connected binaphthyl compound can be used as a hole transport layer material or a hole injection layer material in the organic electroluminescent device, and compared with the compound in the prior art, the compound can further reduce the driving voltage of the OLED device, improve the luminous efficiency and prolong the service life.
the invention also provides an organic electroluminescent device, which comprises a substrate, a first electrode, a second electrode and one or more organic layers which are inserted between the first electrode and the second electrode, wherein the organic layers comprise the novel binaphthyl compound connected at alpha, alpha' positions of naphthalene.
specifically, one embodiment of the invention provides an organic electroluminescent device, which comprises a substrate, and an anode layer, a plurality of light-emitting functional layers and a cathode layer which are sequentially formed on the substrate, wherein each light-emitting functional layer comprises a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is arranged between the hole transport layer and the electron transport layer, wherein the hole transport layer or the hole injection layer contains the binaphthyl compound shown in the formula (I) and connected with the alpha and alpha' positions of naphthalene.
The OLED device prepared by the compound has low starting voltage, high luminous efficiency and better service life, and can meet the requirements of current panel manufacturing enterprises on high-performance materials.
The compound of the present invention can be applied to organic electronic devices, for example, organic electroluminescent devices, lighting devices, organic thin-film transistors, organic field-effect transistors, organic thin-film solar cells, large-area sensors such as information labels, electronic artificial skin sheets and sheet-type scanners, electronic paper, organic EL panels, and the like.
The specific reason why the above-mentioned compound of the present invention is excellent as a hole transport layer material or a hole injection layer material in an organic electroluminescent device is not clear, and the following reason is presumed to be possible:
compared with the compound of the invention in which four completely same Ar groups are connected to N on alpha position of naphthalene ring, the compound has more changes in structure, and the performance can be accurately regulated and controlled through each part of structure, so as to obtain the material with better performance.
In addition, the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Detailed Description
The specific production method of the above-mentioned novel compound of the present invention will be described in detail below by taking a plurality of synthesis examples as examples, but the production method of the present invention is not limited to these synthesis examples.
The basic chemical materials of various chemicals used in the present invention, such as petroleum ether, ethyl acetate, sodium sulfate, toluene, tetrahydrofuran, methylene chloride, acetic acid, potassium phosphate, sodium tert-butoxide, etc., are commercially available from Shanghai Tankatake technologies, Inc. and Xilongchemical, Inc. The mass spectrometer used for determining the following compounds was a ZAB-HS type mass spectrometer measurement (manufactured by Micromass, UK).
The synthesis of the compounds of the present invention is briefly described below.
Synthetic examples
Representative synthetic route 1 (Ar in the Compound of formula1、Ar2、Ar3、Ar4Not all at the same time):
Figure BDA0001879749010000131
more specifically, the following gives synthetic methods of representative compounds of the present invention.
Synthesis example 1: synthesis of Compound P29
Figure BDA0001879749010000132
In a 1000ml single-neck flask, 16.9g (100mmol) of 4-aminobiphenyl, 25.1g (110mmol) of 2-bromobiphenyl, 0.7g (1mmol) of [1, 1' -bis (diphenylphosphino) ferrocene ] dichloropalladium, 500ml of toluene and 14.4g (150mmol) of sodium tert-butoxide are added, the mixture is vacuumized and nitrogen is exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder M1.
In a 1000ml single-neck bottle, 35.3g (110mmol) of M1, 20.6g (50mmol) of 2,2 '-dibromo-1, 1' -binaphthyl, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium and 500ml of toluene are added, vacuum pumping is carried out for 3 times of nitrogen exchange, the temperature is increased to 110 ℃ for reaction for 12 hours, after the reaction is finished, the solvent is distilled off, and silica gel column chromatography is carried out to obtain P29.
Synthesis example 2: synthesis of Compound P34
Figure BDA0001879749010000141
In a 1000ml single-neck flask, 24.6g (100mmol) of 2-bromodibenzofuran, 9.3g (100mmol) of aniline, 0.7g (1mmol) of [1, 1' -bis (diphenylphosphino) ferrocene ] palladium dichloride, 500ml of toluene and 14.4g (150mmol) of sodium tert-butoxide are added, the mixture is evacuated and nitrogen is exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder M2.
28.5g (110mmol) of M2, 20.6g (50mmol) of 2,2 '-dibromo-1, 1' -binaphthyl, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium and 500ml of toluene are added into a 1000ml single-neck bottle, vacuum pumping is carried out for 3 times of nitrogen exchange, the temperature is increased to 110 ℃ for reaction for 12 hours, after the reaction is finished, the solvent is distilled off, and silica gel column chromatography is carried out to obtain P34.
Synthesis example 3: synthesis of Compound P56
Figure BDA0001879749010000142
In a 1000ml single-neck flask, 26.1g (100mmol) of 2-bromodibenzothiophene, 9.3g (100mmol) of aniline, 0.7g (1mmol) of [1, 1' -bis (diphenylphosphino) ferrocene ] palladium dichloride, 500ml of toluene and 14.4g (150mmol) of sodium tert-butoxide are added, the vacuum is pumped and nitrogen is exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder M3.
30.2g (110mmol) of M3, 20.6g (50mmol) of 2,2 '-dibromo-1, 1' -binaphthyl, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium and 500ml of toluene are added into a 1000ml single-neck bottle, vacuum pumping is carried out for 3 times of nitrogen exchange, the temperature is increased to 110 ℃ for reaction for 12 hours, after the reaction is finished, the solvent is distilled off, and silica gel column chromatography is carried out to obtain P56.
Synthesis example 4: synthesis of Compound P80
Figure BDA0001879749010000151
In a 1000ml single-neck flask, 20.5g (100mmol) of 1-bromonaphthalene, 9.3g (100mmol) of aniline, 0.7g (1mmol) of [1, 1' -bis (diphenylphosphino) ferrocene ] palladium dichloride, 500ml of toluene and 14.4g (150mmol) of sodium tert-butoxide are added, the vacuum is pumped and nitrogen is exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder M4.
In a 1000ml single-neck bottle, 24.1g (110mmol) of M4, 20.6g (50mmol) of 2,2 '-dibromo-1, 1' -binaphthyl, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium and 500ml of toluene are added, vacuum pumping is carried out for 3 times of nitrogen exchange, the temperature is increased to 110 ℃ for reaction for 12 hours, after the reaction is finished, the solvent is distilled off, and silica gel column chromatography is carried out to obtain P80.
Synthesis example 5: synthesis of Compound P91
Figure BDA0001879749010000161
In a 1000ml single-neck flask, 20.5g (100mmol) of 1-bromonaphthalene, 16.9g (100mmol) of 2-aminobiphenyl, 0.7g (1mmol) of [1, 1' -bis (diphenylphosphino) ferrocene ] palladium dichloride, 500ml of toluene and 14.4g (150mmol) of sodium tert-butoxide are added, the mixture is vacuumized and nitrogen is exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder M5.
32.5g (110mmol) of M5, 20.6g (50mmol) of 2,2 '-dibromo-1, 1' -binaphthyl, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium and 500ml of toluene are added into a 1000ml single-neck bottle, vacuum pumping is carried out for 3 times of nitrogen exchange, the temperature is increased to 110 ℃ for reaction for 12 hours, after the reaction is finished, the solvent is distilled off, and silica gel column chromatography is carried out to obtain P91.
Synthesis example 6: synthesis of Compound P109
Figure BDA0001879749010000162
In a 1000ml single-neck flask, 27.2g (100mmol) of 2-bromo-9, 9 '-dimethylfluorene, 9.3g (100mmol) of aniline, 0.7g (1mmol) of [1, 1' -bis (diphenylphosphino) ferrocene ] dichloropalladium, 500ml of toluene and 14.4g (150mmol) of sodium tert-butoxide are added, the vacuum is pumped and nitrogen is exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder M6.
30g (110mmol) of M6, 20.6g (50mmol) of 2,2 '-dibromo-1, 1' -binaphthyl, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium and 500ml of toluene are added into a 1000ml single-neck bottle, the vacuum pumping and nitrogen exchange are carried out for 3 times, the temperature is increased to 110 ℃ for reaction for 12 hours, after the reaction is finished, the solvent is removed by evaporation, and the silica gel column chromatography is carried out to obtain P109.
Synthesis example 7: synthesis of Compound P127
Figure BDA0001879749010000171
In a 1000ml single-neck flask, 27.2g (100mmol) of 2-bromo-9, 9 '-dimethylfluorene, 14.3g (100mmol) of 1-naphthylamine, 0.7g (1mmol) of [1, 1' -bis (diphenylphosphino) ferrocene ] dichloropalladium, 500ml of toluene and 14.4g (150mmol) of sodium tert-butoxide are added, the mixture is vacuumized and nitrogen is exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder M7.
In a 1000ml single-neck bottle, 36.8g (110mmol) of M7, 20.6g (50mmol) of 2,2 '-dibromo-1, 1' -binaphthyl, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium and 500ml of toluene are added, nitrogen is exchanged for 3 times by vacuumizing, the temperature is increased to 110 ℃ for reaction for 12 hours, after the reaction is finished, the solvent is distilled off, and silica gel column chromatography is carried out to obtain P127.
Synthesis example 8: synthesis of Compound P128
Figure BDA0001879749010000181
In a 1000ml single-neck flask, 27.2g (100mmol) of 2-bromo-9, 9 '-dimethylfluorene, 14.3g (100mmol) of 2-naphthylamine, 0.7g (1mmol) of [1, 1' -bis (diphenylphosphino) ferrocene ] dichloropalladium, 500ml of toluene and 14.4g (150mmol) of sodium tert-butoxide are added, the mixture is vacuumized and nitrogen-exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder M8.
In a 1000ml single-neck bottle, 36.8g (110mmol) of M8, 20.6g (50mmol) of 2,2 '-dibromo-1, 1' -binaphthyl, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium and 500ml of toluene are added, nitrogen is exchanged for 3 times by vacuumizing, the temperature is increased to 110 ℃ for reaction for 12 hours, after the reaction is finished, the solvent is distilled off, and silica gel column chromatography is carried out to obtain P128.
Synthesis example 9: synthesis of Compound P168
Figure BDA0001879749010000182
In a 1000ml single-neck flask, 27.2g (100mmol) of 2-bromo-9, 9 '-dimethylfluorene, 16.9g (100mmol) of 2-aminobiphenyl, 0.7g (1mmol) of [1, 1' -bis (diphenylphosphino) ferrocene ] dichloropalladium, 500ml of toluene and 14.4g (150mmol) of sodium tert-butoxide are added, the mixture is vacuumized and nitrogen-exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder M9.
40g (110mmol) of M9, 23.6g (50mmol) of 4,4 ' -dimethoxy-2, 2 ' -dibromo-1, 1 ' -binaphthyl, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium and 500ml of toluene are added into a 1000ml single-neck bottle, vacuum pumping is carried out for 3 times of nitrogen exchange, the temperature is increased to 110 ℃ for reaction for 12 hours, after the reaction is finished, the solvent is distilled off, and silica gel column chromatography is carried out to obtain P168.
The solvents and reagents used in the present invention, such as aniline, 1-naphthylamine, 2-bromo-9, 9 '-dimethylfluorene, 2-bromodibenzofuran, 2-bromodibenzothiophene, 2-aminobiphenyl, 2' -dibromo-1, 1 '-binaphthyl, 4-bromobiphenyl, [1, 1' -bis (diphenylphosphino) ferrocene ] dichloropalladium, tris (dibenzylideneacetone) dipalladium, toluene, petroleum ether, n-hexane, dichloromethane, acetone, sodium sulfate, ethyl acetate, ethanol, triphenylphosphine, potassium/sodium tert-butoxide, etc., can be purchased or customized from the domestic chemical product market, for example, from national pharmaceutical group reagents, Sigma-Aldrich, Bailingo reagents. In addition, they can be synthesized by a known method by those skilled in the art.
based on the synthetic route and thought of the binaphthyl compound connected at the α th position of the above naphthalene, those skilled in the art can obtain a compound in which the substituent is Ar1、Ar2、Ar3And Ar4Compound (Ar) of (A)1、Ar2、Ar3And Ar4Not the same selection at the same time).
Device embodiments
The organic electroluminescent device is described in detail with the following embodiments:
the OLED includes first and second electrodes, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof may be used. When the first electrode is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and a combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
for example, the hole injection layer may be one or more of the above-described novel naphthalene compounds connected at the α, α 'position of naphthalene according to the present invention, or one or more of the following HI1-HI3, or one or more of the following HI1-HI3 may be doped with one or more of the novel naphthalene compounds connected at the α, α' position.
Figure BDA0001879749010000201
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
According to different technologies, the luminescent layer material can be different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescent luminescent material, and the like. In an OLED device, a single light emitting technology may be used, or a combination of a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The host material of the light emitting layer is selected from, but not limited to, one or more of RH-1 to RH-31.
Figure BDA0001879749010000202
Figure BDA0001879749010000211
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer thereof may be selected from, but not limited to, a combination of one or more of RPD-1 to RPD-28 listed below.
Figure BDA0001879749010000212
Figure BDA0001879749010000221
The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, the combination of one or more of ET-1 through ET-57 listed below.
Figure BDA0001879749010000222
Figure BDA0001879749010000231
Figure BDA0001879749010000241
Figure BDA0001879749010000251
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer materials including, but not limited to, combinations of one or more of the following.
LiQ,LiF,NaCl,CsF,Li2O,Cs2CO3,BaO,Na,Li,Ca。
The preparation process of the organic electroluminescent device in the embodiment is as follows:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, performing vacuum evaporation on the anode layer film to form HI-3 serving as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
the transport materials in the examples and comparative examples were vacuum-evaporated on the hole injection layer as the hole transport layer of the device at an evaporation rate of 0.1nm/s and a total film thickness of 80 nm;
a luminescent layer of the device is evaporated on the hole transport layer in vacuum, the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material RH-1 is adjusted to be 0.1nm/s, the evaporation rate of the dye RPD-1 is set in a proportion of 3%, and the total film thickness of evaporation is 30nm by using a multi-source co-evaporation method;
vacuum evaporating an electron transport layer material ET42 of the device on the light-emitting layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 30 nm;
LiF with the thickness of 0.5nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 150nm is used as a cathode of the device.
The organic electroluminescent device prepared by the above process was subjected to the following performance measurement:
the driving voltage and current efficiency and the lifetime of the organic electroluminescent devices prepared in examples 1 to 9 and comparative examples 1 to 2 were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 5000cd/m2The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency; the life test of LT95 is as follows: using a luminance meter at 5000cd/m2The luminance drop of the organic electroluminescent device was measured to be 4750cd/m by maintaining a constant current at luminance2Time in hours.
The following OLED devices of the examples and comparative examples of the present invention were prepared according to the above-described process, and specifically, the materials used for preparing the devices in each of the examples and comparative examples were as follows:
example 1
The following devices were prepared according to the above-described method using the compound P29 of the present invention as a hole transporting material, and device performance tests were carried out according to the above-described organic electroluminescent device test method.
Example 2
The following devices were prepared according to the above-described method using the compound P34 hole transport material of the present invention, and device performance tests were performed according to the above-described organic electroluminescent device test method.
Example 3
The following devices were prepared according to the above-described method using the compound P56 hole transport material of the present invention, and device performance tests were performed according to the above-described organic electroluminescent device test method.
Example 4
The following devices were prepared according to the above-described method using the compound P80 hole transport material of the present invention, and device performance tests were performed according to the above-described organic electroluminescent device test method.
Example 5
The following devices were prepared according to the above-described method using the compound P91 hole transport material of the present invention, and device performance tests were performed according to the above-described organic electroluminescent device test method.
Example 6
The following devices were prepared according to the above-described method using the compound P109 hole transport material of the present invention, and device performance tests were performed according to the above-described organic electroluminescent device test method.
Example 7
The following devices were prepared according to the above-described method using the compound P127 hole transport material of the present invention, and device performance tests were performed according to the above-described organic electroluminescent device test method.
Example 8
The following devices were prepared according to the above-described method using the compound P128 hole transport material of the present invention, and device performance tests were performed according to the above-described organic electroluminescent device test method.
Example 9
The following devices were prepared according to the above-described method using the compound P168 hole transport material of the present invention, and device performance tests were performed according to the above-described organic electroluminescent device test method.
Comparative example 1
The organic electroluminescent device of comparative example 1 was selected with the transport material R-1,
Figure BDA0001879749010000271
the following devices were prepared in accordance with the above-described method using the compound R-1 as a transport material, and device performance tests were conducted in accordance with the above-described organic electroluminescent device test method.
Comparative example 2
The organic electroluminescent device of comparative example 2 was selected with the transport material R-2,
Figure BDA0001879749010000281
the following devices were prepared in accordance with the above-described method using the compound R-2 as a transport material, and device performance tests were conducted in accordance with the above-described organic electroluminescent device test method.
The organic electroluminescent device properties are given in the following table:
Figure BDA0001879749010000282
the results show that the novel organic material is used for the organic electroluminescent device, can effectively reduce the take-off and landing voltage and improve the current efficiency, and is a hole transport material with good performance.
Compared with materials R-1 and R-2 in the prior art as comparative compounds, four Ar in the molecular structures of the compounds R-1 and R-2 are completely the same, and the accumulation forms of molecules and molecules cannot be well regulated, so that the hole transport capability of the material is reduced, the voltage is relatively high, and the luminous efficiency and the service life of the OLED devices prepared in comparative examples 1 and 2 are reduced.
Although the invention has been described in connection with the embodiments, the invention is not limited to the embodiments described above, and it should be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the invention, and the scope of the invention is outlined by the appended claims.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.

Claims (10)

1. A compound of the general formula (I):
Figure FDA0001879746000000011
wherein: ar (Ar)1、Ar2、Ar3And Ar4Each independently selected from substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C6-C30A condensed aryl group of (A), a substituted or unsubstituted C3-C30One of the heteroaryl groups of (a);
L1、L2、L3and L4Each independently selected from the group consisting of a single bond, substituted or unsubstituted C6-C30Arylene of (a), substituted or unsubstituted C6-C30Heteroarylene group of (a), substituted or unsubstituted C6-C30One of the fused arylene groups of (a);
and L as mentioned above1-Ar1、L2-Ar2、L3-Ar3And L4-Ar4The same substituent groups are not simultaneously selected;
R1、R2each independently selected from H, halogen atom, C1-C20Alkoxy, cyclic or acyclic C of1-C20Alkyl, cyano, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C6-C30A condensed aryl group of (A), a substituted or unsubstituted C3-C30One of the heteroaryl groups of (a);
m and n are each independently selected from integers from 0 to 6;
when the above groups have substituents, the substituents are respectively and independently selected from halogen and C1-C10Alkyl or cycloalkyl of, C2-C10Alkenyl radical, C1-C6Alkoxy or thioalkoxy group of (C)6-C30Monocyclic aromatic hydrocarbon or condensed ring aromatic hydrocarbon group of (A), C3-C30One of the monocyclic heteroaromatic group or the condensed ring heteroaromatic group of (a).
2. The compound of formula (la) according to claim 1, wherein in formula (I), Ar1And Ar4Each independently is a structure of formula (A) below, and Ar1、Ar2、Ar3And Ar4Different from each other:
Figure FDA0001879746000000021
in the formula (A): x is selected from CR3R4、NR5O or S;
R3to R6Each independently selected from H, C with or without ring formation1-C20Alkyl, cyano, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C6-C30A condensed aryl group of (A), a substituted or unsubstituted C3-C30One of the heteroaryl groups of (a); and R is3And R4Can be connected into a ring;
p is an integer of 0 to 7;
L5selected from single bond, substituted or unsubstituted C6-C30Arylene of (a), substituted or unsubstituted C6-C30One of the heteroarylene groups of (1).
3. A compound of formula (la) according to claim 1, wherein in formula (1):
L1、L2、L3and L4Is a single bond.
4. A compound of formula (la) according to claim 1, wherein formula (1):
R1、R2each independently selected from H, halogen atom, cyano, C1-C10Alkoxy, cyclic or acyclic C of1-C10One of the alkyl groups of (1).
5. The compound of formula (I) according to claim 2, wherein in formula (A), L5Is a single bond.
6. A compound of formula (la) according to claim 1, selected from the compounds of the following specific structures:
Figure FDA0001879746000000022
Figure FDA0001879746000000031
Figure FDA0001879746000000041
Figure FDA0001879746000000051
Figure FDA0001879746000000061
Figure FDA0001879746000000071
Figure FDA0001879746000000081
Figure FDA0001879746000000091
7. use of a compound of formula (la) according to claim 1 as hole transport material in an organic electroluminescent device.
8. Use of a compound according to claim 6 as a hole transport material in an organic electroluminescent device.
9. An organic electroluminescent device comprising a first electrode, a second electrode and one or more organic layers interposed between said first and second electrodes, characterized in that said organic layers comprise at least one compound represented by general formula (i) of claim 1.
10. An organic electroluminescent device comprising a first electrode, a second electrode and one or more organic layers interposed between said first and second electrodes, characterized in that said organic layers comprise at least one compound as claimed in claim 6.
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