CN111606813B - Compound, organic electronic light-emitting device comprising same and application thereof - Google Patents

Compound, organic electronic light-emitting device comprising same and application thereof Download PDF

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CN111606813B
CN111606813B CN201910140656.6A CN201910140656A CN111606813B CN 111606813 B CN111606813 B CN 111606813B CN 201910140656 A CN201910140656 A CN 201910140656A CN 111606813 B CN111606813 B CN 111606813B
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compound
fused ring
aryl
layer
heteroaryl
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CN111606813A (en
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王志鹏
张维宏
曾礼昌
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Beijing Eternal Material Technology Co Ltd
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Abstract

A compound, an organic electronic light emitting device including the same, and applications thereof. Wherein the compound is represented by the following chemical formula:Wherein Ar 1 is selected from a substituted or unsubstituted C 10～C50 fused ring aryl or C 6～C50 fused ring heteroaryl; ar 2 is selected from one of hydrogen, deuterium, halogen, C 1～C12 alkyl, C 3～C30 cycloalkyl, C 1～C12 alkoxy, C 3～C30 cycloalkoxy, alkenyl, alkynyl, carbonyl, cyano, C 6～C50 aryl, C 3～C30 heteroaryl, C 10～C50 fused ring aryl, and C 6～C50 fused ring heteroaryl; l 1 and L 2 are independently selected from one of a single bond, a substituted or unsubstituted C 1～C12 alkylene, C 6-C50 arylene, C 3-C30 heteroarylene, C 10～C50 fused ring arylene, and C 6～C50 fused ring heteroarylene; n is an integer of 0 to 5. The compound of the invention introduces condensed ring aryl or condensed ring heteroaryl at ortho position of aniline, which is beneficial to enhancing charge transmission and improving charge mobility of molecules, thereby being beneficial to reducing device voltage.

Description

Compound, organic electronic light-emitting device comprising same and application thereof
Technical Field
The invention relates to the field of organic light-emitting compounds and organic light-emitting devices, in particular to a compound, an organic light-emitting device containing the compound and application of the compound and the organic light-emitting device
Background
The display technology plays an important role in the aspects of acquiring knowledge, knowing information and leisure and entertainment, and has no great achievement obtained by the display technology from the original heavy cathode ray tube and plasma television to the light-emitting diode capable of displaying in a large area to the currently mainstream flat panel display technology, namely liquid crystal display. However, with the rapid development of information science and technology, the requirements on display devices are higher and higher, and the display devices have the aspects of high resolution, high response speed, wide viewing angle, portability, low power consumption, full color and the like, so that the display devices become the development direction of future flat panel displays.
Organic light-emitting diodes (OLEDs) using organic semiconductors as functional materials are rapidly developing as a new generation of all-solid-state flat panel display technology. Compared with other display technologies, the OLED technology has the advantages of wide viewing angle, high response speed, low driving voltage, wide adaptable display temperature range, realization of full-color display from blue light to red light spectrum region and the like. The device fabrication process is relatively simple, and OLED is most attractive to realize flexible display that can be curled by using a flexible substrate.
In the organic light emitting device, materials used as the organic layer can be largely classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and the like according to functions. According to the light emission mechanism, a fluorescent material that emits light by a singlet excited state of electrons and a phosphorescent material that emits light by a triplet excited state of electrons can be classified. In order to effectively alleviate aggregation of luminescent materials and triplet excitons and avoid concentration quenching, a host-guest doping system in which the luminescent materials are doped in a host material is generally adopted, and excitons generated by the host are transmitted to the dopant, so that high-efficiency light is emitted.
At present, the OLED display technology still has the problems of high driving voltage and short display life, which seriously affects the further practical application of the technology. Accordingly, there is a need for continued efforts to develop organic light emitting devices having low voltage driving, high luminance, and long life.
The organic hole material plays an important role in transferring holes injected from the anode to the light emitting layer, and the hole transport material having excellent hole mobility is advantageous for injection balance of carriers in the device, thereby realizing reduction of device driving voltage. On the other hand, excitons generated in the light-emitting layer move to the hole-transporting layer, and eventually emit light at the interface between the hole-transporting layer and the light-emitting layer, resulting in problems of color shift and reduction in light-emitting efficiency. This requires an auxiliary layer between the hole transport layer and the light emitting layer to block the transfer of excitons to the hole transport layer, prevent efficiency roll-off and improve the stability of the device; patent KR1020170100709 reports a triarylamine compound having a main structure of 2, 4-dinaphthyl aniline. However, there is still a continuing need in the art to meet the needs of practical use.
Disclosure of Invention
The main object of the present invention is to provide a compound, an organic electronic light emitting device comprising the same and use thereof, in order to at least partially solve at least one of the above technical problems.
According to an aspect of the present invention, there is provided a compound represented by the following chemical formula:
Wherein Ar 1 is selected from a substituted or unsubstituted C 6～C50 fused ring aryl or C 6～C50 fused ring heteroaryl;
Ar 2 is selected from one of hydrogen, deuterium, halogen, C 1～C12 alkyl, C 3～C30 cycloalkyl, C 1～C12 alkoxy, C 3～C30 cycloalkoxy, alkenyl, alkynyl, carbonyl, cyano, C 6-C50 aryl, C 3-C30 heteroaryl, C 10～C50 fused ring aryl, and C 6～C50 fused ring heteroaryl, wherein said alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkenyl, alkynyl, carbonyl, aryl, heteroaryl, fused ring aryl, and fused ring heteroaryl are substituted or unsubstituted; l 1 and L 2 are independently selected from one of a single bond, a substituted or unsubstituted C 1～C12 alkylene, C 6-C50 arylene, C 3-C30 heteroarylene, C 10～C50 fused ring arylene, and C 6～C50 fused ring heteroarylene; g 1 is selected from one of substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, fluorene, spirofluorene, dibenzofuran, dibenzothiophene, dibenzoselenophene, azafluorene, azadibenzofuran, azadibenzothiophene, and azadibenzoselenophene; g 2 is selected from one of substituted or unsubstituted C 6-C50 aryl, C 3-C30 heteroaryl, C 10-C50 fused ring aryl, and C 6-C50 fused ring heteroaryl; the substituents when G 2 and/or Ar 2 are substituted are independently selected from one of hydrogen, deuterium, halogen, C 1～C12 alkyl, C 3～C30 cycloalkyl, C 1～C12 alkoxy, C 3～C30 cycloalkoxy, alkenyl, alkynyl, carbonyl, cyano, C 6-C50 aryl, C 3-C30 heteroaryl, C 10-C50 fused ring aryl, and C 6-C50 fused ring heteroaryl; n is an integer of 0 to 5.
According to still another aspect of the present invention, there is also provided an organic electroluminescent device including a first electrode and a second electrode, and an organic material layer between the first electrode and the second electrode, wherein,
The organic material layer includes the above-described compound;
Preferably, the organic material layer includes a hole transport region containing the above-described compound;
preferably, the hole transport region comprises a hole transport layer and/or an electron blocking layer, wherein at least one of the hole transport layer and the electron blocking layer comprises the compound described above.
According to a further aspect of the present invention there is provided the use of a compound according to the above as a hole transport layer and/or electron blocking layer in an organic electroluminescent device.
Based on the technical scheme, the compound and the organic light-emitting device have the following beneficial effects compared with the prior art:
The compound of the invention introduces condensed ring aryl or condensed ring heteroaryl at ortho position of aniline (namely Ar 1), which is beneficial to enhancing charge transmission and improving charge mobility of molecules, thereby being beneficial to reducing device voltage; when the polymer is used as an electron blocking layer, the efficiency roll-off of the device can be restrained, and the service life of the device is prolonged;
When the compound is used as an auxiliary layer of an organic light-emitting device, such as an organic material layer, the hole transmission efficiency can be improved, the electron blocking capability is good, the purposes of reducing the voltage of the device, prolonging the service life of the device and improving the stability of the device can be realized;
when the compound is used as a hole transport layer, the transport speed of holes can be improved, so that the injection balance of carriers is facilitated; when the organic light-emitting device is used as an electron blocking layer, the transfer of excitons to a hole transport layer can be blocked, the occurrence of the roll-off phenomenon of efficiency can be suppressed, and a stable organic light-emitting device with low voltage and long service life can be realized.
Drawings
Fig. 1 is a schematic view of an organic electroluminescent device according to an embodiment of the present invention;
Fig. 2 is a schematic view showing a specific structure of the organic material layer in fig. 1.
Detailed Description
The present invention will be further described in detail below with reference to specific embodiments and with reference to the accompanying drawings, in order to make the objects, technical solutions and advantages of the present invention more apparent.
According to the basic concept of the present invention, the enhanced charge transport can be facilitated by providing a compound wherein a fused ring aryl or fused ring heteroaryl is introduced in the ortho position of the aniline (i.e., ar 1); and the compound may be incorporated into an organic electroluminescent device.
The compounds according to the embodiments of the present invention may be represented by the following chemical formulas:
Wherein Ar 1 is selected from a substituted or unsubstituted C 10～C50 fused ring aryl or C 6～C50 fused ring heteroaryl;
Ar 2 is selected from one of hydrogen, deuterium, halogen, C 1～C12 alkyl, C 3～C30 cycloalkyl, C 1～C12 alkoxy, C 3～C30 cycloalkoxy, alkenyl, alkynyl, carbonyl, cyano, C 6-C50 aryl, C 3-C30 heteroaryl, C 10～C50 fused ring aryl, and C 6～C50 fused ring heteroaryl, wherein said alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkenyl, alkynyl, carbonyl, aryl, heteroaryl, fused ring aryl, and fused ring heteroaryl are substituted or unsubstituted;
L 1 and L 2 are independently selected from one of a single bond, a substituted or unsubstituted C 1～C12 alkylene, C 6-C50 arylene, C 3-C30 heteroarylene, C 10～C50 fused ring arylene, and C 6～C50 fused ring heteroarylene;
G 1 is selected from one of substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, fluorene, spirofluorene, dibenzofuran, dibenzothiophene, dibenzoselenophene, azafluorene, azadibenzofuran, azadibenzothiophene, and azadibenzoselenophene;
g2 Selecting is one of a substituted or unsubstituted C 6-C50 aryl, C 3-C30 heteroaryl, C 10-C50 fused ring aryl, and C 6-C50 fused ring heteroaryl;
the substituent when G 2 or Ar 2 is substituted is selected from one of hydrogen, deuterium, halogen, C 1～C12 alkyl, C 3～C30 cycloalkyl, C 1～C12 alkoxy, C 3～C30 cycloalkoxy, alkenyl, alkynyl, carbonyl, cyano, C 6-C50 aryl, C 3-C30 heteroaryl, C 10-C50 fused ring aryl, and C 6-C50 fused ring heteroaryl;
n is an integer of 0 to 5.
In some embodiments, ar 1 may be selected from a substituted or unsubstituted C 10～C30 fused ring aryl or C 6-C30 fused ring heteroaryl; preferably a C 10～C30 fused ring aryl or C 6-C30 fused ring heteroaryl; further preferred is a C 6～C15 fused ring aryl group. Preferably, ar 1 is naphthyl, fluorenyl, phenanthryl, fluoranthenyl, triphenylenyl, furanyl, thienyl, indolyl, dibenzofuran, or dibenzothiophene.
In some embodiments, ar 2 is selected from hydrogen, deuterium, halogen, C 1～C12 alkyl, C 3～C30 cycloalkyl, C 1～C12 alkoxy, C 3～C30 cycloalkoxy, alkenyl, C 6-C50 aryl, C 3-C30 heteroaryl, alkynyl, C 10-C50 fused ring aryl, or C 6-C50 fused ring heteroaryl; preferably, ar 2 is hydrogen, deuterium, halogen, C 1～C12 alkyl, C 10-C50 fused ring aryl or C 6-C50 fused ring heteroaryl; further preferred, ar 2 is hydrogen, a C 10-C50 fused ring aryl or a C 6-C50 fused ring heteroaryl.
In some embodiments, n is 0 to 3, preferably n is 0.
In some embodiments, the substituents when G 2 or Ar 2 are substituted are selected from hydrogen, deuterium, halogen, C 1～C12 alkyl, C 1～C12 alkoxy, C 6-C50 aryl, C 3-C30 heteroaryl, C 10-C50 fused ring aryl, or C 6-C50 fused ring heteroaryl; preferably, the substituents are selected from hydrogen, deuterium, C 1～C12 alkyl, C 1～C12 alkoxy, C 6-C50 aryl, C 3-C30 heteroaryl, C 10-C50 fused ring aryl or C 6-C50 fused ring heteroaryl; further preferred substituents are selected from hydrogen, C 1～C12 alkyl, C 1～C12 alkoxy, C 6-C50 aryl or C 3-C30 heteroaryl.
The G 1 is selected from phenyl, biphenyl, terphenyl, naphthyl, fluorene, spirofluorene, dibenzofuran, dibenzothiophene, dibenzoselenophene, azafluorene, azadibenzofuran, azadibenzothiophene, and azadibenzoselenophene, or a combination thereof; preferably, G 1 is selected from fluorene, spirofluorene, dibenzofuran, dibenzothiophene or dibenzoselenophene; further preferred, G 1 is selected from fluorene, spirofluorene, dibenzofuran or dibenzothiophene.
In some embodiments, the L 1 and L 2 are independently selected from a single bond, or phenylene; preferably, L 1 and L 2 are independently selected from single bonds.
The specific compounds of the above chemical formula may be represented by, but not limited to, the following compounds:
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The compounds of the examples of the present invention may be synthesized by referring to the schemes shown below, but it should be noted that the method and route used in the present invention are not limited to the method and route used in the present invention, and those skilled in the art may select other methods or routes to obtain the novel compounds of the present invention.
The intermediates (i.e. 1, 2,3 in the schemes) present in the examples of the present invention are exemplified by, but not limited to, the following compounds:
examples of methods for synthesizing intermediates
Synthesis of intermediate M1
Synthesis of Compound M1-1
The starting material 4-aminobiphenyl (50.0 g,295 mmol) was dissolved in 350mL of solvent N, N-dimethylformamide, placed in a three-necked flask equipped with a constant pressure dropping funnel and cooled to 0℃with an ice-water bath. N-bromosuccinimide (52.6 g,295 mmol) was dissolved in 300mL of N, N-dimethylformamide, placed in a constant pressure dropping funnel, and slowly dropped in a reaction bottle, the reaction temperature was kept between 0 ℃ and 5 ℃, the dropwise addition was completed for about one hour, the reaction was further kept for half an hour, the reaction was monitored to be complete, the reaction solution was poured into 1000mL of ice water, extracted with ethyl acetate (500 mL, three times), the organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated to obtain a brown oil, and purified with a silica gel column (petroleum ether/ethyl acetate, 10/1) to obtain a pale yellow solid, 60g, with a yield of 82%.
Synthetic intermediate M1
The compound M1-1 (50.0 g,202 mmol) synthesized in the above step, 1-naphthalene boric acid (38.1 g,222 mol) and potassium carbonate (36.2 g,262 mmol) were placed in a 1000mL three-necked flask, stirred well, then the air on the flask was replaced with nitrogen three times, and tetrakis triphenylphosphine palladium (4.66 g,4.03 mmol) was added to the reaction solution under nitrogen protection, and then the temperature was raised to 100℃for 18 hours. After cooling, the reaction solution was poured into a saturated aqueous ammonium chloride solution, extracted with ethyl acetate (500 mL, three times), the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to a reddish brown oil. The crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10/1) to give 50g of an off-white solid in 84% yield.
Synthetic intermediate M2
The synthesis of intermediate M2 can be referred to the synthesis of intermediate M1, except that 1-naphthalene boronic acid is replaced by 2-naphthalene boronic acid in the synthesis.
Synthetic intermediate M3
The synthesis of intermediate M3 can be referred to the synthesis of intermediate M1, except that 1-naphthalene boronic acid is replaced by 9-phenanthrene boronic acid in the synthesis.
Synthetic intermediate M4
The synthesis of intermediate M4 can be referred to the synthesis of intermediate M1, except that 1-naphthalene boronic acid is replaced by 2-fluorene boronic acid in the synthesis.
Synthetic intermediate M5
The synthesis of intermediate M5 can be referred to the synthesis of intermediate M1, except that 1-naphthalene boronic acid is replaced by 4-fluorene boronic acid in the synthesis.
Synthetic intermediate M6
The synthesis of intermediate M6 can be referred to the synthesis of intermediate M1, except that 1-naphthalene boronic acid is replaced by 2-phenanthrene boronic acid in the synthesis.
Synthetic intermediate M7
The synthesis of intermediate M7 can be referred to the synthesis of intermediate M1, except that 1-naphthalene boronic acid is converted to fluoranthene-9-boronic acid in the synthesis.
Synthesis of Synthesis intermediate M8
The synthesis of intermediate M8 can be referred to as follows.
Synthesis of Compound M8-1
2-Bromo-4-iodoaniline (10.0 g,33.6 mmol), 4- [2- (9, 9-dimethylfluorene) ] phenylboronic acid- (11.6 g,36.9 mol) and potassium carbonate (6.03 g,43.6 mmol) were placed in a 250mL three-necked flask, stirred well enough, then the air on the flask was replaced with nitrogen three times, and tetrakis triphenylphosphine palladium (387 mg,0.336 mmol) was added to the reaction solution under nitrogen protection, then the temperature was raised to 100℃and reacted for 18 hours. After cooling, the reaction solution was poured into a saturated aqueous ammonium chloride solution, extracted with ethyl acetate (150 mL, three times), the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to a reddish brown oil. The crude product was purified by silica gel chromatography (petroleum ether/ethyl acetate, 10/1) to give 10g of an off-white solid in 68% yield.
Synthetic intermediate M8
M8-1 (10.0 g,22.7 mmol), 1-naphthalene boric acid (5.19 g,30.2 mol) and potassium carbonate (4.93 g,35.6 mmol) were placed in a 250mL three-necked flask, stirred well, then the air on the flask was replaced with nitrogen three times, and tetrakis triphenylphosphine palladium (317 mg,0.275 mmol) was added to the reaction solution under nitrogen protection, and then the temperature was raised to 100℃for 18 hours. After cooling, the reaction solution was poured into a saturated aqueous ammonium chloride solution, extracted with ethyl acetate (150 mL, three times), the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to a reddish brown oil. The crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10/1) to give 8.7g of an off-white solid in 77% yield.
Synthetic intermediate M9
The synthesis of the intermediate M9 can refer to a synthesis method of the intermediate M8, and 4- [2- (9, 9-dimethylfluorene) ] phenylboronic acid is replaced by 4- (1-naphthyl) phenylboronic acid; 1-naphthalene boric acid is changed into 2-naphthalene boric acid.
Synthetic intermediate M10
The synthesis of the intermediate M10 can refer to the synthesis method of the intermediate M1, and the 1-naphthalene boric acid is changed into 9-boric acid anthracene.
Synthesis example 1
For example, synthesis of compound C4:
synthesis of Compound C4-1
Intermediate M1 (10.0 g,33.9 mmol) and 2-bromo-9, 9 dimethylfluorene (10.2 g,37.2 mmol) were placed in a 250mL three-necked flask, then sodium tert-butoxide (3.9 g,40.6 mmol) and toluene (150 mL) were added, after thorough stirring, the air in the flask was replaced with nitrogen, and then the catalyst [1,1' -bis (diphenylphosphino) ferrocene ] palladium dichloride (248 mg,0.448 mmol) and 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (178 mg,0.678 mmol) were added and the reaction was warmed to 100℃for 16h. After cooling to room temperature, the reaction solution was poured into a saturated aqueous ammonium chloride solution, extracted with ethyl acetate (100 mL, three times), the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated by filtration to give a brown oily substance which was purified by column chromatography on silica gel (petroleum ether/dichloromethane, 15/1) to give 15g of a white solid in 90% yield.
Synthesis of Compound C4
Compound C4-1 (15 g,30.8 mmol), 2- (4-bromophenyl) dibenzothiophene (11.5 g,33.8 mmol) and sodium t-butoxide (3.55 g,36.9 mmol) were placed in a 500mL three-necked flask containing 200mL toluene, and dissolved by stirring thoroughly. The air in the flask was then fully purged with nitrogen, and then the catalyst tris (dibenzylideneacetone) dipalladium (282 mg,0.308 mmol) and 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (505 mg,1.23 mmol) were added to the reaction solution and warmed to reflux for 18h. After cooling, the reaction solution was poured into a saturated aqueous ammonium chloride solution, extracted with ethyl acetate (200 mL, three times), the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to a brown-black oil. The crude product was purified by silica gel column chromatography (petroleum ether/dichloromethane, 15/1) to give a pale yellow solid. The solid was recrystallized twice from toluene and methanol and further purified by sublimation to give 9.5g of a pale yellow solid of 99.9% purity.
Synthetic methods of synthetic examples 2-26 reference may be made to synthetic example 1, and the corresponding starting materials employed are summarized in Table 1.
TABLE 1
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Based on the same inventive concept, the embodiments of the present invention also provide an organic electroluminescent device comprising the above embodiment compound. The following description will be given by way of example using an OLED as an organic electroluminescent device as a device example, but it should be understood that the following detailed description is not limiting of the invention and that the following detailed description can be extended to other organic electroluminescent devices by those skilled in the art.
Device embodiment
As shown in fig. 1, the OLED comprises a first electrode 11 and a second electrode 12, and an organic material layer 13 between the two electrodes. As shown in fig. 2, the organic material layer 13 may be divided into a plurality of regions. For example, the organic material layer 13 may include a hole transport region 133, a light emitting layer 132, and an electron transport region 131.
In a specific embodiment, a substrate may be used under the first electrode 11 or over the second electrode 12. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency. A Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode 11 may be formed by sputtering or depositing a material serving as the first electrode 11 on the substrate. When the first electrode 11 is used as the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), zinc oxide (ZnO), or the like, and any combination thereof may be used. When the first electrode 11 is used as a cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (A1), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) and any combination thereof can be used.
The organic material layer 13 may be formed on the first electrode 11 by vacuum thermal evaporation, spin coating, printing, or the like. The compounds used as the organic material layer may be small organic molecules, large organic molecules and polymers, and combinations thereof.
The hole transport region 133 is located between the anode and the light emitting layer 132. The hole transport region 133 may be a Hole Transport Layer (HTL) of a single layer structure including a single layer hole transport layer containing only one compound and a single layer hole transport layer containing a plurality of compounds. The hole transport region may have a multilayer structure including at least one of a Hole Injection Layer (HIL) 1333, a Hole Transport Layer (HTL) 1332, and an Electron Blocking Layer (EBL) 1331.
The material of the hole transport region 133 may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or conductive dopant-containing polymers such as polystyrene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as the compounds shown below HT-1 to HT-34; or any combination thereof.
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The hole injection layer 1333 is located between the anode and the hole transport layer 1332. The hole injection layer 1333 may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer 1333 may employ one or more compounds of HT-1 through HT-34 described above, or one or more compounds of HI1 through HI3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI1 to HI3 described below.
The light emitting layer 132 includes a light emitting dye (i.e., dopant) that can emit different wavelength spectrums, and may also include a Host material (Host). The light emitting layer 132 may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The plurality of monochromatic light emitting layers with different colors can be arranged in a plane according to the pixel pattern, or can be stacked together 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 132 may be a single color light emitting layer capable of simultaneously emitting different colors of red, green, blue, etc.
The material of the light emitting layer 132 may be a fluorescent electroluminescent material, a phosphorescent electroluminescent material, a thermally activated delayed fluorescence light emitting material, or the like according to various techniques. In an OLED device, a single light emitting technology may be used, or a combination of different light emitting technologies may be used. The different luminescent materials classified by the technology can emit light of the same color, and can also emit light of different colors.
In one aspect of the invention, the light emitting layer 132 employs a fluorescent electroluminescence technique. The luminescent layer 132 fluorescent host material thereof may be selected from, but is not limited to, one or more combinations of BFH-1 through BFH-16 listed below.
In one aspect of the invention, the light emitting layer 132 employs a fluorescent electroluminescence technique. The luminescent layer fluorescent dopant thereof may be selected from, but is not limited to, one or more combinations of BFD-1 through BFD-12 listed below.
In one aspect of the present invention, the light emitting layer 132 employs phosphorescent electroluminescence technology. The luminescent layer host material is selected from, but not limited to, one or more of GPH-1 to GPH-80.
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In one aspect of the present invention, the light emitting layer 132 employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of GPD-1 to GPD-47 listed below.
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In one aspect of the present invention, the light emitting layer 132 employs phosphorescent electroluminescence technology. The luminescent layer host material is selected from, but not limited to, one or more of RH-1 to RH-31.
In one aspect of the present invention, the light emitting layer 132 employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of the RPD-1 through RPD-28 listed below.
In one aspect of the present invention, the light emitting layer 132 employs phosphorescent electroluminescence technology. The phosphorescent dopant of the light emitting layer may be selected from, but not limited to, one or more combinations of YPD-1 to YPD-11 listed below.
In one aspect of the invention, the light emitting layer 132 employs a thermally activated delayed fluorescence light emission technique. The luminescent layer fluorescent dopant thereof may be selected from, but is not limited to, one or a combination of more of TDEs 1 to 39 listed below.
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In one aspect of the invention, the light emitting layer 132 employs a thermally activated delayed fluorescence light emission technique. The host material of the luminescent layer is selected from one or a combination of a plurality of TDH-1-TDH-24.
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The OLED organic material layer may further include an electron transport region 131 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, combinations of one or more of ET-1 through ET-57 listed below.
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The device may further include an electron injection layer between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, a combination of one or more of the following:
LiQ, liF, naCl, csF, li 2O、Cs2CO3, baO, na, li or Ca.
The preparation process of the organic electroluminescent device in this embodiment is as follows:
comparative example 1
The glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam;
placing the glass substrate with the anode in a vacuum cavity, vacuumizing to 1X 10 -5～9×10-3 Pa, and vacuum evaporating HI-1 on the anode layer film as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10nm;
vacuum evaporation HT-4 is carried out on the hole injection layer to serve as a hole transmission layer of the device, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 80nm;
Vacuum evaporation is carried out on the hole transport layer to obtain HT-14 as an electron blocking layer of the device, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 35nm;
Vacuum evaporating a luminescent layer of the device on the hole transport layer, wherein the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material GPH-17 is regulated to be 0.1nm/s by utilizing a multi-source co-evaporation method, the evaporation rate of the dye GPD-12 is set to be 3 percent, and the total evaporation film thickness is 30nm;
Vacuum evaporating electron transport layer material ET-17 of the device on the luminescent layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 30nm;
LiF with the thickness of 0.5nm is vacuum evaporated on an Electron Transport Layer (ETL) to serve as an electron injection layer, and an Al layer with the thickness of 150nm serves as a cathode of the device.
The structure of part of the organic compounds used in the device examples of the present invention is as follows:
The device comparative examples 2 and 3, and examples 1 to 8 of the present invention were fabricated in the same manner as the device comparative example 1, except that the hole transport material HT-4 was replaced with the corresponding other comparative compound (HT-27, R-2) or example compound, as shown in Table 2 below.
The performance, i.e. voltage and lifetime, of the above devices was measured at a luminance of 10000cd/m 2. The method for measuring the lifetime (LT 97) is as follows: the device brightness was continuously detected at a constant current with an initial brightness of 10000cd/m 2, and the time required for the brightness to decay to 9700cd/m 2 was recorded as lifetime (LT 97). These device performance data are summarized in table 2:
TABLE 2
The results show that the organic material provided by the embodiment of the invention is used for an organic electroluminescent device, can effectively reduce the starting voltage, improves the service life of the device, and is a hole transport material with good performance.
The compounds of the embodiments of the present invention may also act as electron blocking layers. The device structure and fabrication method are the same as those of device comparative example 1, except that the electron blocking material HT-14 is replaced with the corresponding comparative compound (R-1, R-2) or example compound. The electron blocking layer material information and properties for each device example are summarized in table 3 below:
TABLE 3 Table 3
When the organic material is used as an electron blocking material, the organic material provided by the embodiment of the invention has obvious lifting effect on reducing the starting voltage and prolonging the service life of a device. In example 16, the lifetime of the device was increased by 36% and the voltage was reduced by 0.5V relative to comparative example 4. In other embodiments, it has also been found that the materials of the present invention may achieve different device performance enhancements. It can be seen that the compounds of the present embodiments are also good performing electron blocking layer materials.
The examples of the present invention are not limited to the use of the corresponding functional layers, and for example, compounds C1, C7, C8, C22 and the like as hole transport layers may be used as electron blocking layers; compounds C6, C11, C13, C23, C25, etc. as electron blocking layers may also be used as hole transport layers.
The foregoing description of the embodiments has been provided for the purpose of illustrating the general principles of the invention, and is not meant to limit the invention thereto, but to limit the invention thereto, and any modifications, equivalents, improvements and equivalents thereof may be made without departing from the spirit and principles of the invention.

Claims (9)

1. A compound represented by the formula:
Wherein Ar 1 is selected from naphthyl and phenanthryl;
Ar 2 is selected from one of hydrogen, deuterium, halogen, C 1～C12 alkyl, C 3～C30 cycloalkyl, C 1～C12 alkoxy, C 3～C30 cycloalkoxy, alkenyl, alkynyl, carbonyl, cyano, C 6-C50 aryl, C 3-C30 heteroaryl, C 10～C50 fused ring aryl, and C 6～C50 fused ring heteroaryl, wherein said alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkenyl, alkynyl, carbonyl, aryl, heteroaryl, fused ring aryl, and fused ring heteroaryl are substituted or unsubstituted;
l 1 and L 2 are independently selected from a single bond, or phenylene;
G 1 is selected from one of phenyl, biphenyl, terphenyl, naphthyl, fluorene, spirofluorene, dibenzofuran, dibenzothiophene and dibenzoselenophene;
G 2 is selected from one of substituted or unsubstituted C 6-C50 aryl and C 10-C50 condensed ring aryl;
The substituents when G 2 is substituted are independently selected from hydrogen, C 1～C12 alkyl, C 1～C12 alkoxy, C 6-C50 aryl, or C 3-C30 heteroaryl;
n is 0.
2. The compound according to claim 1, wherein G 1 is selected from fluorene, spirofluorene, dibenzofuran, dibenzothiophene or dibenzoselenophene.
3. A compound according to claim 1, wherein G 1 is selected from fluorene, spirofluorene, dibenzofuran or dibenzothiophene.
4. The compound of claim 1, wherein L 1 and L 2 are independently selected from single bonds.
5. A compound, characterized in that it is selected from one of the following compounds:
6. An organic electroluminescent device comprising a first electrode and a second electrode, and an organic material layer between the first electrode and the second electrode, wherein,
The organic material layer comprising the compound of any one of claims 1-5.
7. The organic electroluminescent device of claim 6, wherein the organic material layer comprises a hole transport region comprising the compound of any one of claims 1-5.
8. An organic electroluminescent device according to claim 7, wherein the hole transport region comprises a hole transport layer and/or an electron blocking layer, wherein at least one of the hole transport layer and the electron blocking layer comprises a compound according to any one of claims 1 to 5.
9. Use of a compound according to any one of claims 1 to 5 as hole transport layer and/or electron blocking layer in an organic electroluminescent device.
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