CN111606813A - 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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CN111606813A
CN111606813A CN201910140656.6A CN201910140656A CN111606813A CN 111606813 A CN111606813 A CN 111606813A CN 201910140656 A CN201910140656 A CN 201910140656A CN 111606813 A CN111606813 A CN 111606813A
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radical
aryl
compound
heteroaryl
fused ring
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CN111606813B (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 containing the same and application thereof are provided. Wherein the compound is represented by the following formula:
Figure DDA0001977589240000011
wherein Ar is1Selected from substituted or unsubstituted C10～C50With condensed ring aryl or C6～C50A fused ring heteroaryl; ar (Ar)2Selected from hydrogen, deuterium, halogen, C1～C12Alkyl radical, C3～C30Cycloalkyl radical, C1～C12Alkoxy radical, C3～C30Cycloalkoxy, alkenyl, alkynyl, carbonyl, cyano, C6～C50Aryl radical, C3～C30Heteroaryl group, C10～C50Condensed ring aryl and C6～C50One of fused ring heteroaryl; l is1And L2Independently selected from single bond, substituted or unsubstituted C1～C12Alkylene radical, C6‑C50Arylene radical, C3‑C30Heteroarylene group, C10～C50Arylene group having condensed rings and C6～C50One of a fused ring heteroaryl; n is an integer of 0 to 5. The compound of the invention introduces condensed ring aryl or condensed ring heteroaryl at the ortho position of aniline, which is beneficial to enhancing charge transmission and improving the charge mobility of molecules, thereby being beneficial to reducing the voltage of devices。

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 electronic light-emitting devices, in particular to a compound, an organic electronic light-emitting device containing the compound and application of the compound
Background
Display technology plays an important role in people's knowledge acquisition, information understanding, and entertainment, ranging from the original thick cathode ray tube and plasma television to the light emitting diode capable of large-area display, and then to the current mainstream flat panel display technology, liquid crystal display, without showing the huge achievement of display technology. However, with the rapid development of information science and technology, the requirements for display devices are higher and higher, and the aspects of high resolution, high response speed, wide viewing angle, portability, low power consumption, full color and the like become the development direction of the future flat panel display.
Organic light-emitting diodes (OLEDs), which use organic semiconductors as functional materials, are rapidly developing as a new generation of all-solid-state flat panel display technologies. 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, capability of realizing full-color display from blue light to red light spectrum region and the like. The device process is relatively simple, and the OLED is most attractive by using a flexible substrate to realize a rollable flexible display.
In the organic light emitting device, materials used as an organic layer are broadly 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, the fluorescent material can be classified into a fluorescent material emitting light by a singlet excited state of electrons and a phosphorescent material emitting light by a triplet excited state of electrons. In order to effectively alleviate aggregation of a light emitting material and triplet excitons and avoid concentration quenching, a host-guest doping system in which a light emitting material is doped in a host material is generally adopted, and excitons generated by the host are transferred to a dopant, thereby emitting light with high efficiency.
As far as the current is concerned, the OLED display technology still has the problems of high driving voltage and short display lifetime, which seriously affects the further practicality of the technology. Accordingly, there is a continuous effort to develop an organic light emitting device 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 with excellent hole mobility is beneficial to the injection balance of carriers in the device, so that the driving voltage of the device is reduced. On the other hand, excitons generated in the light-emitting layer move to the hole transport layer, and eventually light is emitted at the interface between the hole transport layer and the light-emitting layer, which causes 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 exciton migration to the hole transport layer, prevent the efficiency roll-off and improve the stability of the device; patent KR1020170100709 reports a triarylamine compound having a main structure of 2, 4-dinaphthylaniline. However, there is still a need for further improvement in the prior art to meet the requirements of practical use.
Disclosure of Invention
It is a primary object of the present invention to provide a compound, an organic electronic light emitting device comprising the same, and applications thereof, which are intended 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 formula:
Figure BDA0001977589220000021
wherein Ar is1Selected from substituted or unsubstituted C6～C50With condensed ring aryl or C6～C50A fused ring heteroaryl;
Ar2selected from hydrogen, deuterium, halogen, C1～C12Alkyl radical, C3～C30Cycloalkyl radical, C1～C12Alkoxy radical, C3～C30Cycloalkoxy, alkenyl, alkynyl, carbonyl, cyano, C6-C50Aryl radical, C3-C30Heteroaryl group, C10～C50Condensed ring aryl and C6～C50One of a 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 is1And L2Independently selected from single bond, substituted or unsubstituted C1～C12Alkylene radical, C6-C50Arylene radical, C3-C30Heteroarylene group, C10～C50Arylene group having condensed rings and C6～C50One of a fused ring heteroaryl; g1One selected from the group consisting of substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, fluorene, spirofluorene, dibenzofuran, dibenzothiophene, dibenzoselenophene, azafluorene, azadibenzofuran, azadibenzothiophene, and azadibenzoselenophene; g2Selected from substituted or unsubstituted C6-C50Aryl radical, C3-C30Heteroaryl group, C10-C50Condensed ring aryl and C6-C50One of fused ring heteroaryl; g2And/or Ar2The substituents when substituted are independently selected from hydrogen, deuterium, halogen, C1～C12Alkyl radical, C3～C30Cycloalkyl radical, C1～C12Alkoxy radical, C3～C30Cycloalkoxy, alkenyl, alkynyl, carbonyl, cyano, C6-C50Aryl radical, C3-C30Heteroaryl group, C10-C50Condensed ring aryl and C6-C50One of 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 electronic light emitting device including first and second electrodes, and an organic material layer between the first and second electrodes, wherein,
the organic material layer includes the compound described above;
preferably, the organic material layer includes a hole transport region containing the compound described above;
preferably, the hole transport region includes a hole transport layer and/or an electron blocking layer, wherein at least one of the hole transport layer and the electron blocking layer contains 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 an electron blocking layer in an organic electronic light emitting device.
Based on the technical scheme, compared with the prior art, the compound and the organic light-emitting device have the following beneficial effects:
compounds of the invention in the ortho position to the aniline (i.e. Ar)1) Condensed ring aryl or condensed ring heteroaryl is introduced, so that the charge transmission is enhanced, and the charge mobility of the molecule is improved, thereby being beneficial to reducing the voltage of a device; when the material is used as an electron blocking layer, the efficiency roll-off of the device can be inhibited, and the service life of the device is prolonged;
when the compound is used as an auxiliary layer of an organic material layer of an organic light-emitting device, the hole transmission efficiency can be improved, the compound has good electron blocking capability, and 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 electroluminescent device is used as an electron blocking layer, the organic electroluminescent device can block the transfer of excitons to a hole transport layer, inhibit the occurrence of an efficient roll-off phenomenon, and realize a stable organic electroluminescent device with low voltage and long service life.
Drawings
FIG. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present invention;
fig. 2 is a schematic diagram of a specific structure of the organic material layer in fig. 1.
Detailed Description
In order that the objects, technical solutions and advantages of the present invention will become more apparent, the present invention will be further described in detail with reference to the accompanying drawings in conjunction with the following specific embodiments.
According to the basic concept of the present invention, by providing a compound in the ortho position to the aniline (i.e. Ar)1) The introduction of fused ring aryl or fused ring heteroaryl can be beneficial to enhancing charge transmission; and the compound may be incorporated into an organic electronic light emitting device.
The compounds according to the embodiments of the present invention can be represented by the following chemical formula:
Figure BDA0001977589220000041
wherein Ar is1Selected from substituted or unsubstituted C10～C50With condensed ring aryl or C6～C50A fused ring heteroaryl;
Ar2selected from hydrogen, deuterium, halogen, C1～C12Alkyl radical, C3～C30Cycloalkyl radical, C1～C12Alkoxy radical, C3～C30Cycloalkoxy, alkenyl, alkynyl, carbonyl, cyano, C6-C50Aryl radical, C3-C30Heteroaryl group, C10～C50Condensed ring aryl and C6～C50One of a 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;
L1and L2Independently selected from single bond, substituted or unsubstituted C1～C12Alkylene radical, C6-C50Arylene radical, C3-C30Heteroarylene group, C10～C50Arylene group having condensed rings and C6～C50One of a fused ring heteroaryl;
G1one selected from the group consisting of substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, fluorene, spirofluorene, dibenzofuran, dibenzothiophene, dibenzoselenophene, azafluorene, azadibenzofuran, azadibenzothiophene and azadibenzoselenophene;
G2selectingFrom substituted or unsubstituted C6-C50Aryl radical, C3-C30Heteroaryl group, C10-C50Condensed ring aryl and C6-C50One of fused ring heteroaryl;
G2or Ar2When substituted, the substituents are selected from hydrogen, deuterium, halogen, C1～C12Alkyl radical, C3～C30Cycloalkyl radical, C1～C12Alkoxy radical, C3～C30Cycloalkoxy, alkenyl, alkynyl, carbonyl, cyano, C6-C50Aryl radical, C3-C30Heteroaryl group, C10-C50Condensed ring aryl and C6-C50One of fused ring heteroaryl;
n is an integer of 0 to 5.
In some embodiments, Ar1May be selected from substituted or unsubstituted C10～C30With condensed ring aryl or C6-C30A fused ring heteroaryl; preferably C10～C30With condensed ring aryl or C6-C30A fused ring heteroaryl; more preferably C6～C15A fused ring aryl group. Preferably, Ar is1Is naphthyl, fluorenyl, phenanthryl, fluoranthenyl, triphenylenyl, furanyl, thienyl, indolyl, dibenzofuran, or dibenzothiophene.
In some embodiments, Ar2Selected from hydrogen, deuterium, halogen, C1～C12Alkyl radical, C3～C30Cycloalkyl radical, C1～C12Alkoxy radical, C3～C30Cycloalkoxy, alkenyl, C6-C50Aryl radical, C3-C30Heteroaryl, alkynyl, C10-C50Condensed ring aryl or C6-C50A fused ring heteroaryl; preferably, Ar is2Is hydrogen, deuterium, halogen, C1～C12Alkyl radical, C10-C50Condensed ring aryl or C6-C50A fused ring heteroaryl; further preferably, Ar2Is hydrogen, C10-C50Condensed ring aryl or C6-C50Fused ring heteroaryl.
In some embodiments, n is 0 to 3, preferably n is 0.
In some embodiments, G2Or Ar2When substituted, the substituents are selected from hydrogen, deuterium, halogen, C1～C12Alkyl radical, C1～C12Alkoxy radical, C6-C50Aryl radical, C3-C30Heteroaryl group, C10-C50Condensed ring aryl or C6-C50A fused ring heteroaryl; preferably, the substituents are selected from hydrogen, deuterium, C1～C12Alkyl radical, C1～C12Alkoxy radical,C6-C50Aryl radical, C3-C30Heteroaryl group, C10-C50Condensed ring aryl or C6-C50A fused ring heteroaryl; further preferably, the substituents are selected from hydrogen, C1～C12Alkyl radical, C1～C12Alkoxy radical, C6-C50Aryl or C3-C30A heteroaryl group.
The G is1Selected from phenyl, biphenyl, terphenyl, naphthyl, fluorene, spirofluorene, dibenzofuran, dibenzothiophene, dibenzoselenophene, azafluorene, azadibenzofuran, azadibenzothiophene and azadibenzoselenophene, or combinations thereof; preferably, G1Selected from fluorene, spirofluorene, dibenzofuran, dibenzothiophene or dibenzoselenophene; further preferably, G1Selected from fluorene, spirofluorene, dibenzofuran or dibenzothiophene.
In some embodiments, the L1And L2Independently selected from a single bond, or phenylene; preferably, L1And L2Independently selected from single bonds.
The specific compounds of the above formula may be represented by, but are not limited to, the following compounds:
Figure BDA0001977589220000061
Figure BDA0001977589220000071
Figure BDA0001977589220000081
Figure BDA0001977589220000091
Figure BDA0001977589220000101
Figure BDA0001977589220000111
Figure BDA0001977589220000121
Figure BDA0001977589220000131
Figure BDA0001977589220000141
the compounds of the examples of the present invention can be synthesized by referring to the following schemes, but it should be noted that the obtaining of the compounds is not limited to the methods and routes used in the present invention, and those skilled in the art can select other methods or routes to obtain the novel compounds of the present invention.
Figure BDA0001977589220000142
The intermediates (i.e., 1, 2, and 3 in the schemes) appearing in the examples of the present invention are exemplified by, but not limited to, the following compounds:
Figure BDA0001977589220000151
synthetic method example of intermediate
Synthesis of intermediate M1
Figure BDA0001977589220000152
Synthesis of Compound M1-1
The starting material, 4-aminobiphenyl (50.0g, 295mmol), was dissolved in 350mL of N, N-xylene carboxamide solvent, placed in a three-necked flask equipped with a constant pressure dropping funnel and cooled to 0 ℃ with an ice-water bath. Dissolving N-bromosuccinimide (52.6g, 295mmol) in 300mL of N, N-xylene formamide, placing in a constant-pressure dropping funnel, slowly dropping the solution in a reaction bottle, keeping the reaction temperature between 0 ℃ and 5 ℃, dropping for about one hour, keeping the temperature for half an hour, monitoring the complete reaction of the raw materials, pouring the reaction solution into 1000mL of ice water, extracting with ethyl acetate (500mL, three times), combining the organic phases, washing with saturated saline solution once, drying with anhydrous sodium sulfate, filtering, concentrating to obtain brown oily matter, and purifying with a silica gel chromatographic column (petroleum ether/ethyl acetate, 10/1) to obtain 60g of light yellow solid with the yield of 82%.
Synthesis of intermediate M1
The compound M1-1(50.0g, 202mmol) synthesized in the previous step, 1-naphthalene boronic acid (38.1g, 222 mmol) and potassium carbonate (36.2g, 262mmol) were placed in a 1000mL three-necked flask, stirred well, then the air on the flask was replaced with nitrogen three times, tetratriphenylphosphine palladium (4.66g, 4.03mmol) was added to the reaction solution under nitrogen protection, and then the temperature was raised to 100 ℃ for reaction for 18 h. After cooling, the reaction was poured into saturated aqueous ammonium chloride solution, extracted with ethyl acetate (500mL, three times), the organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated to give 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.
Synthesis of intermediate M2
The synthesis of intermediate M2 was performed according to the synthesis method of intermediate M1 except that 1-naphthalene boronic acid was replaced by 2-naphthalene boronic acid in the synthesis.
Synthesis of intermediate M3
The synthesis of intermediate M3 was performed according to the synthesis method of intermediate M1 except that 1-naphthylboronic acid was replaced by 9-phenanthreneboronic acid.
Synthesis of intermediate M4
The synthesis of intermediate M4 was performed according to the synthesis method of intermediate M1 except that 1-naphthoic acid was changed to 2-fluorenylboronic acid in the synthesis.
Synthesis of intermediate M5
The synthesis of intermediate M5 was performed according to the synthesis method of intermediate M1 except that 1-naphthoic acid was changed to 4-fluorenylboronic acid.
Synthesis of intermediate M6
The synthesis of intermediate M6 was performed according to the synthesis method of intermediate M1 except that 1-naphthylboronic acid was replaced by 2-phenanthreneboronic acid.
Synthesis of intermediate M7
Synthesis of intermediate M7 reference was made to the method of synthesis of intermediate M1 except that 1-naphthalene boronic acid was replaced with fluoranthene-9-boronic acid in the synthesis.
Synthesis of Synthesis intermediate M8
The synthesis of intermediate M8 can be referred to the following method.
Figure BDA0001977589220000171
Synthesis of Compound M8-1
2-bromo-4-iodoaniline (10.0g, 33.6mmol), 4- [2- (9, 9-dimethylfluorene) ] phenylboronic acid- (11.6g, 36.9mol) and potassium carbonate (6.03g, 43.6mmol) were placed in a 250mL three-necked flask, stirred well, then the air on the flask was replaced with nitrogen three times, tetratriphenylphosphine palladium (387mg, 0.336mmol) was added to the reaction under nitrogen protection, and then the temperature was raised to 100 ℃ for 18 h. After cooling, the reaction was poured into saturated aqueous ammonium chloride, extracted with ethyl acetate (150mL, 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 10g of an off-white solid in 68% yield.
Synthesis of intermediate M8
M8-1(10.0g, 22.7mmol), 1-naphthalene boronic acid (5.19g, 30.2mol) and potassium carbonate (4.93g, 35.6mmol) were placed in a 250mL three-necked flask, stirred well, then the air on the flask was replaced with nitrogen three times, palladium tetratriphenylphosphine (317mg, 0.275mmol) was added to the reaction solution under nitrogen protection, and then the temperature was raised to 100 ℃ for reaction for 18 h. After cooling, the reaction was poured into saturated aqueous ammonium chloride, extracted with ethyl acetate (150mL, 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 (petrol ether/ethyl acetate, 10/1) to give 8.7g of an off-white solid in 77% yield.
Synthesis of intermediate M9
Synthesis of intermediate M9 referring to the synthesis of intermediate M8, 4- [2- (9, 9-dimethylfluorene) ] phenylboronic acid was changed to 4- (1-naphthyl) phenylboronic acid; 1-naphthalene boronic acid was changed to 2-naphthalene boronic acid.
Synthesis of intermediate M10
Synthesis of intermediate M10 the 1-naphthaleneboronic acid was changed to 9-boronic acid anthracene with reference to the synthesis of intermediate M1.
Synthesis example 1
For example, synthesis of compound C4:
Figure BDA0001977589220000181
synthesis of Compound C4-1
Intermediate M1(10.0g, 33.9mmol) and 2-bromo-9, 9-dimethylfluorene (10.2g, 37.2mmol) were placed in a 250mL three-necked flask, followed by the addition of sodium tert-butoxide (3.9g, 40.6mmol) and toluene (150mL), after stirring well, nitrogen was used to replace the air in the flask, followed by the addition of catalyst [1, 1 ' -bis (diphenylphosphino) ferrocene ] dichloropalladium (248mg, 0.448mmol) and 2-dicyclohexylphosphine-2 ', 6 ' -dimethoxybiphenyl (278mg, 0.678mmol), which was heated to 100 ℃ for 16 h. After cooling to room temperature, the reaction mixture was poured into a saturated aqueous ammonium chloride solution, extracted with ethyl acetate (100mL, three times), the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to give a brown oil which was purified by silica gel column chromatography (petroleum ether/dichloromethane, 15/1) to give 15g of a white solid in 90% yield.
Synthesis of Compound C4
Compound C4-1(15g, 30.8mmol), 2- (4-bromophenyl) dibenzothiophene (11.5g, 33.8mmol) and sodium tert-butoxide (3.55g, 36.9mmol) were charged in a 500mL three-necked flask containing 200mL of toluene and dissolved with stirring. Then, the atmosphere in the flask was sufficiently changed with nitrogen, and then the catalysts tris (dibenzylideneacetone) dipalladium (282mg, 0.308mmol) and 2-dicyclohexylphosphine-2 ', 6' -dimethoxybiphenyl (505mg, 1.23mmol) were added to the reaction solution, and the temperature was raised to reflux reaction for 18 hours. After cooling, the reaction was poured into saturated aqueous ammonium chloride, extracted with ethyl acetate (200mL, three times), the organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated to a brownish-black oil. The crude product was purified by column chromatography over silica gel (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 to 26 the starting materials used in synthetic example 1 were referred to and are summarized in Table 1.
TABLE 1
Figure BDA0001977589220000191
Figure BDA0001977589220000201
Figure BDA0001977589220000211
Figure BDA0001977589220000221
Based on the same inventive concept, the embodiments of the present invention also provide an organic electronic light emitting device including the compound of the above embodiment. The following is an example of an OLED as an organic electronic light emitting device, but it should be understood that the following detailed description is not a limitation of the present invention, and those skilled in the art can expand the following detailed description to be applied to other organic electronic light emitting devices.
Device embodiments
As shown in fig. 1, the OLED includes 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, an emission layer 132, and an electron transport region 131.
In a specific embodiment, a substrate may be used below the first electrode 11 or above the second electrode 12. 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 11 may be formed by sputtering or depositing a material used as the first electrode 11 on the substrate. When the first electrode 11 serves 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 11 is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (a1), 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 13 may be formed on the first electrode 11 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.
A 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 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)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 polymers containing conductive dopants such as polyphenylenevinylene, 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 compounds shown below in HT-1 to HT-34; or any combination thereof.
Figure BDA0001977589220000231
Figure BDA0001977589220000241
Figure BDA0001977589220000251
A 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 compounds. For example, the hole injection layer 1333 may employ one or more compounds of HT-1 to HT-34 described above, or one or more compounds of HI1-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-HI3 described below.
Figure BDA0001977589220000252
The light emitting layer 132 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 132 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 132 may be a single color light emitting layer capable of emitting red, green, blue, and the like at the same time.
According to different technologies, the material of the light-emitting layer 132 can be different materials such as a fluorescent electroluminescent material, a phosphorescent electroluminescent material, a thermal activation delayed fluorescent 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 132 employs a fluorescent electroluminescent technology. The luminescent layer 132 fluorescent host material may be selected from, but is not limited to, the combination of one or more of BFH-1 through BFH-16 listed below.
Figure BDA0001977589220000261
In one aspect of the invention, the light-emitting layer 132 employs a fluorescent electroluminescent technology. The luminescent layer fluorescent dopant may be selected from, but is not limited to, combinations of one or more of BFD-1 through BFD-12 listed below.
Figure BDA0001977589220000271
In one aspect of the invention, the light emitting layer 132 employs phosphorescent electroluminescent technology. The host material of the light emitting layer is selected from, but not limited to, one or more of GPH-1 to GPH-80.
Figure BDA0001977589220000272
Figure BDA0001977589220000281
Figure BDA0001977589220000291
Figure BDA0001977589220000301
In one aspect of the invention, the light emitting layer 132 employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer can be selected from, but is not limited to, one or more of GPD-1 to GPD-47 listed below.
Figure BDA0001977589220000302
Figure BDA0001977589220000311
In one aspect of the invention, the light emitting layer 132 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 BDA0001977589220000321
In one aspect of the invention, the light emitting layer 132 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 BDA0001977589220000331
In one aspect of the invention, the light emitting layer 132 employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light-emitting layer can be selected from, but is not limited to, one or more of YPD-1 to YPD-11 listed below.
Figure BDA0001977589220000341
In one aspect of the present invention, the light-emitting layer 132 employs a thermally activated delayed fluorescence emission technique. The fluorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more of TDE 1-TDE 39 listed below.
Figure BDA0001977589220000342
Figure BDA0001977589220000351
In one aspect of the present invention, the light-emitting layer 132 employs a thermally activated delayed fluorescence emission technique. The host material of the light emitting layer is selected from, but not limited to, one or more of TDH-1-TDH-24.
Figure BDA0001977589220000361
Figure BDA0001977589220000371
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, the combination of one or more of ET-1 through ET-57 listed below.
Figure BDA0001977589220000372
Figure BDA0001977589220000381
Figure BDA0001977589220000391
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, combinations of one or more of the following:
LiQ、LiF、NaCl、CsF、Li2O、Cs2CO3BaO, Na, Li or Ca.
The preparation process of the organic electroluminescent device in the embodiment is as follows:
comparative example 1
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 obtain HI-1 as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
evaporating HT-4 on the hole injection layer in vacuum to serve as a hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 80 nm;
evaporating HT-14 on the hole transport layer in vacuum to serve as an electron blocking layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 35 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 GPH-17 is adjusted to be 0.1nm/s, the evaporation rate of the dye GPD-12 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 ET-17 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 structures of some of the organic compounds used in the device examples of the present invention are as follows:
Figure BDA0001977589220000401
Figure BDA0001977589220000411
comparative examples 2 and 3 of the device of the present invention, and examples 1 to 8 were fabricated in the same manner as in comparative example 1 of the device, except that the hole transport material HT-4 was replaced with the corresponding other comparative compounds (HT-27, R-2) or example compounds, as shown in table 2 below.
At a luminance of 10000cd/m2The performance, i.e., voltage and lifetime, of the above devices were measured. The method for measuring the service life (LT97) is as follows: at an initial luminance of 10000cd/m2Then, the brightness of the device is continuously detected under the constant current, and the brightness decay is recorded to 9700cd/m2The required time is the lifetime (LT 97). These device performance data are summarized in table 2:
TABLE 2
Figure BDA0001977589220000412
Figure BDA0001977589220000421
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 and prolong the service life of the device, and is a hole transport material with good performance.
The compounds of the embodiments of the invention can also be used as electron blocking layers. The device structure and the manufacturing method were the same as those of comparative device 1 except that the electron blocking material HT-14 was replaced with the corresponding comparative compounds (R-1, R-2) or the example compounds. The information and properties of the electron barrier materials for each device example are summarized in table 3 below:
TABLE 3
Figure BDA0001977589220000422
Figure BDA0001977589220000431
When the organic material is used as an electron blocking material, the organic material provided by the embodiment of the invention has obvious effects of reducing the starting voltage and prolonging the service life of a device. In example 16, the lifetime of the device was improved by 36% and the voltage was reduced by 0.5V compared to comparative example 4. In other embodiments, it is also found that the material of the present invention can achieve different device performance improvements. It can be seen that the compounds of the embodiments of the present invention are also good electron barrier materials.
Examples given in 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 a hole transport layer can be used as an electron blocking layer; compounds C6, C11, C13, C23, C25 and the like which are electron blocking layers can also be used as the hole transporting layer.
The above-mentioned embodiments are intended to illustrate the objects, technical solutions and advantages of the present invention in further detail, and it should be understood that the above-mentioned embodiments are only exemplary embodiments of the present invention and are not intended to limit the present invention, and any modifications, equivalents, improvements and the like made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (10)

1. A compound represented by the formula:
Figure FDA0001977589210000011
wherein Ar is1Selected from substituted or unsubstituted C10～C50With condensed ring aryl or C6～C50A fused ring heteroaryl;
Ar2selected from hydrogen, deuterium, halogen, C1～C12Alkyl radical, C3～C30Cycloalkyl radical, C1～C12Alkoxy radical, C3～C30Cycloalkoxy, alkenyl, alkynyl, carbonyl, cyano, C6-C50Aryl radical, C3-C30Heteroaryl group, C10～C50Condensed ring aryl and C6～C50One of fused ring heteroaryl, wherein the alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkenyl, alkynyl, carbonyl, aryl, heteroarylThe radicals, fused ring aryl and fused ring heteroaryl are substituted or unsubstituted;
L1and L2Independently selected from single bond, substituted or unsubstituted C1～C12Alkylene radical, C6-C50Arylene radical, C3-C30Heteroarylene group, C10～C50Arylene group having condensed rings and C6～C50One of a fused ring heteroaryl;
G1one selected from the group consisting of substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, fluorene, spirofluorene, dibenzofuran, dibenzothiophene, dibenzoselenophene, azafluorene, azadibenzofuran, azadibenzothiophene, and azadibenzoselenophene;
G2selected from substituted or unsubstituted C6-C50Aryl radical, C3-C30Heteroaryl group, C10-C50Condensed ring aryl and C6-C50One of fused ring heteroaryl;
G2or Ar2The substituents when substituted are independently selected from hydrogen, deuterium, halogen, C1～C12Alkyl radical, C3～C30Cycloalkyl radical, C1～C12Alkoxy radical, C3～C30Cycloalkoxy, alkenyl, alkynyl, carbonyl, cyano, C6-C50Aryl radical, C3-C30Heteroaryl group, C10-C50Condensed ring aryl and C6-C50One of fused ring heteroaryl;
n is an integer of 0 to 5.
2. The compound of claim 1, wherein Ar is Ar1Selected from substituted or unsubstituted C10～C30With condensed ring aryl or C6-C30A fused ring heteroaryl; preferably C10～C30With condensed ring aryl or C6-C30A fused ring heteroaryl; further preferably Ar1Is naphthyl, fluorenyl, phenanthryl, fluoranthenyl, triphenylenyl, furanyl, thienyl, indolyl, dibenzofuran or dibenzofuranThiophene.
3. The compound of claim 1, wherein Ar is Ar2Selected from hydrogen, deuterium, halogen, C1～C12Alkyl radical, C3～C30Cycloalkyl radical, C1～C12Alkoxy radical, C3～C30Cycloalkoxy, alkenyl, C6-C50Aryl radical, C3-C30Heteroaryl, alkynyl, C10-C50Condensed ring aryl or C6-C50A fused ring heteroaryl; preferably, Ar is2Is hydrogen, deuterium, halogen, C1～C12Alkyl radical, C10-C50Condensed ring aryl or C6-C50A fused ring heteroaryl; further preferably, Ar2Is hydrogen, C10-C50Condensed ring aryl or C6-C50Fused ring heteroaryl.
4. The compound of claim 1, wherein n is 0 to 3, preferably n is 0.
5. The compound of claim 1, wherein G is2Or Ar2When substituted, the substituents are selected from hydrogen, deuterium, halogen, C1～C12Alkyl radical, C1～C12Alkoxy radical, C6-C50Aryl radical, C3-C30Heteroaryl group, C10-C50Condensed ring aryl or C6-C50A fused ring heteroaryl; preferably, the substituents are selected from hydrogen, deuterium, C1～C12Alkyl radical, C1～C12Alkoxy radical, C6-C50Aryl radical, C3-C30Heteroaryl group, C10-C50Condensed ring aryl or C6-C50A fused ring heteroaryl; further preferably, the substituents are selected from hydrogen, C1～C12Alkyl radical, C1～C12Alkoxy radical, C6-C50Aryl or C3-C30A heteroaryl group.
6. The compound of claim 1, wherein G is1Selected from phenyl, biphenyl, terphenyl, naphthyl, fluorene, spirofluorene, dibenzofuran, dibenzothiophene, dibenzoselenophene, azabicyclofuran, azabiphenylthiophene, azabiphenylselenophene, or combinations thereof; preferably, G1Selected from fluorene, spirofluorene, dibenzofuran, dibenzothiophene or dibenzoselenophene; further preferably, G1Selected from fluorene, spirofluorene, dibenzofuran or dibenzothiophene.
7. The compound of claim 1, wherein L is1And L2Independently selected from a single bond, or phenylene; preferably, L1And L2Independently selected from single bonds.
8. The compound of claim 1, wherein the compound is selected from one of the following compounds:
Figure FDA0001977589210000031
Figure FDA0001977589210000041
Figure FDA0001977589210000051
Figure FDA0001977589210000061
Figure FDA0001977589210000071
Figure FDA0001977589210000081
Figure FDA0001977589210000091
Figure FDA0001977589210000101
Figure FDA0001977589210000111
9. 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 comprises a compound of any one of claims 1-8;
preferably, the organic material layer includes a hole transport region comprising the compound of any one of claims 1 to 8;
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 according to any one of claims 1 to 8.
10. Use of a compound according to any one of claims 1 to 8 as a hole transport layer and/or an electron blocking layer in an organic electronic light emitting device.
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