CN111848414B - Arylamine compound and organic electroluminescent device comprising same - Google Patents

Arylamine compound and organic electroluminescent device comprising same Download PDF

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CN111848414B
CN111848414B CN202010753467.9A CN202010753467A CN111848414B CN 111848414 B CN111848414 B CN 111848414B CN 202010753467 A CN202010753467 A CN 202010753467A CN 111848414 B CN111848414 B CN 111848414B
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hole transport
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杜明珠
孙月
苗玉鹤
邵钰杰
赵倩
朱鸫达
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Changchun Hyperions Technology Co Ltd
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Abstract

The invention provides an arylamine compound and an organic electroluminescent device comprising the same, and relates to the technical field of organic electroluminescence. According to the arylamine compound provided by the invention, a specific phenylfluorene intermediate is introduced into the structure, so that the compound has a proper HOMO energy level, and can be used as a hole transport layer material, so that more holes can be received from an anode, an injection barrier between the hole transport layer and a light emitting layer can be reduced, the injection and the transmission of the holes are facilitated, and the hole mobility is improved. Secondly, the phenylfluorene intermediate has certain distortion in structure, so that the film-forming property of the compound can be effectively improved, and the crystallization effect is reduced. Thirdly, the arylamine compound has good thermal stability and higher carrier mobility by introducing a substituent group with rigidity and a large pi conjugated system. The present invention also provides an organic electroluminescent device having high luminous efficiency and excellent life performance.

Description

Arylamine compound and organic electroluminescent device comprising same
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to an arylamine compound and an organic electroluminescent device comprising the arylamine compound.
Background
An Organic Light-Emitting Diode (OLED) is an all-solid-state Light-Emitting device, and has the advantages of high brightness, high contrast, high definition, wide viewing angle, wide color gamut, ultra-thinness, ultra-Light, low power consumption, wide temperature, self-luminescence, high luminous efficiency, short reaction time, transparency, flexibility, and the like, and is already commercially available in the fields of mobile phones, televisions, micro displays, and the like, and is called as a "illusion display" by the people in the industry, and will become a novel display technology with the most development potential in the future.
In organic electroluminescent devices, the choice of materials has a significant impact on the performance of the device. OLED materials can be classified into light emitting materials, hole transport materials, electron transport materials, and the like according to their functions. The hole transport material is an important organic photoelectric functional material, and can improve the transport efficiency of holes in the device and block electrons in a light-emitting layer. Although the research on hole transport materials has been greatly advanced and commercial hole transport materials such as TPD, NPD, etc. have been available, the thermal stability is poor and the lifetime of the device is affected. Therefore, it is still a hot spot of research in this field to develop a hole transport material with stable performance that can be used for industrial mass production, and further improve the stability of the material while maintaining a higher hole transport performance, so as to improve the performance of the organic electroluminescent device in terms of efficiency, lifetime, operating voltage, and the like.
Disclosure of Invention
In view of the above problems of the prior art, the present invention provides an arylamine compound and an organic electroluminescent device including the same.
The invention provides an arylamine compound, which has a structure shown in the following formula (I):
Figure BDA0002610741080000011
wherein L is1、L2Independently selected from single bond or arylene of C6-C30;
Ar1、Ar2、Ar3、Ar4independently selected from aryl of C6-C30 or heteroaryl of C3-C30, or Ar1And Ar2Ar described in3And Ar4The independent bonds form a ring structure;
the aryl group, the arylene group and the heteroaryl group are each substituted or unsubstituted with one or more substituents selected from the group consisting of a deuterium atom, an alkyl group having from C1 to C4, an aryl group having from C6 to C30 and a heteroaryl group having from C3 to C20, and when the substituents are substituted with a plurality of substituents, the substituents may be the same or different from one another.
The invention also provides an organic electroluminescent device which comprises a cathode, an organic layer, an anode and a substrate, wherein the organic layer contains the arylamine compound.
The invention has the beneficial effects that:
the invention provides an arylamine compound, wherein a specific phenylfluorene intermediate is introduced into the structure, so that the compound can have a proper HOMO energy level, and can be used as a hole transport layer material, so that more holes can be received from an anode, an injection barrier between the hole transport layer and a light-emitting layer can be reduced, the hole injection and the hole transport are facilitated, and the hole mobility is improved. Secondly, the phenylfluorene intermediate has certain distortion in structure, so that the film-forming property of the compound can be effectively improved, and the crystallization effect is reduced. Thirdly, the arylamine compound has good thermal stability and higher carrier mobility by introducing a substituent group with rigidity and a large pi conjugated system.
The present invention also provides an organic electroluminescent device having high luminous efficiency and excellent life performance.
Drawings
FIG. 1 shows the compound prepared in example 1 of the present invention1H NMR chart.
FIG. 2 shows the compound prepared in example 2 of the present invention1H NMR chart.
FIG. 3 shows the compound prepared in example 4 of the present invention1H NMR chart.
FIG. 4 shows the compound prepared in example 5 of the present invention1H NMR chart.
FIG. 5 shows the compound prepared in example 6 of the present invention1H NMR chart.
FIG. 6 shows the compound prepared in example 8 of the present invention1H NMR chart.
FIG. 7 shows a compound prepared in example 9 of the present invention1H NMR chart.
Detailed Description
The following will clearly and completely describe the technical solutions of the specific embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the scope of protection of the present invention.
The invention firstly provides a compound which has a structure shown as the following formula (I):
Figure BDA0002610741080000031
wherein L is1、L2Independently selected from single bond or arylene of C6-C30;
Ar1、Ar2、Ar3、Ar4independently selected from aryl of C6-C30 or heteroaryl of C3-C30, or Ar1And Ar2Ar described in3And Ar4The independent bonds form a ring structure;
the aryl group, the arylene group and the heteroaryl group are each substituted or unsubstituted with one or more substituents selected from the group consisting of a deuterium atom, an alkyl group having from C1 to C4, an aryl group having from C6 to C30 and a heteroaryl group having from C3 to C20, and when the substituents are substituted with a plurality of substituents, the substituents may be the same or different from one another. The substituent may include, by way of example, deuterium atom, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, benzophenanthrenyl group, perylenyl group, pyrenyl group, fluorenyl group, 9-dimethylfluorenyl group, 9-diphenylfluorenyl group, dianilino group, carbazolyl group, 9-phenylcarbazolyl group, furyl group, thienyl group, dibenzofuryl group, dibenzothienyl group, phenothiazinyl group, phenoxazinyl group, acridinyl group, pyridyl group, pyrazinyl group, triazinyl group, pyrimidinyl group, etc., but is not limited thereto, and may be a substituent other than those listed above as long as the technical effects of the present invention can be achieved. The substituent may be one or more, and when the substituent is plural, plural substituents may be the same or different.
The alkyl group in the present invention refers to a hydrocarbon group obtained by dropping one hydrogen atom from an alkane molecule, and it may be a straight-chain alkyl group, a branched-chain alkyl group, or a cyclic alkyl group, and preferably has 1 to 15 carbon atoms, more preferably 1 to 10 carbon atoms, and particularly preferably 1 to 4 carbon atoms. Examples may include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, cyclopentyl, cyclohexyl, and the like, but are not limited thereto.
The aryl group in the present invention is a general term for a monovalent group remaining after one hydrogen atom is removed from an aromatic nucleus carbon of an aromatic compound molecule, and the number of aryl carbon atoms is preferably C6 to C30, more preferably C6 to C20, and still more preferably C6 to C12, and may be a monocyclic aryl group, a polycyclic aryl group, or a fused ring aryl group. The monocyclic aryl group means an aryl group having only one aromatic ring in the molecule, for example, phenyl group and the like, but is not limited thereto; the polycyclic aromatic group means an aromatic group having two or more independent aromatic rings in the molecule, for example, biphenyl group, terphenyl group and the like, but is not limited thereto; the fused ring aryl group refers to an aryl group having two or more aromatic rings in a molecule and fused together by sharing two adjacent carbon atoms, and examples thereof include, but are not limited to, naphthyl, anthryl, phenanthryl, fluorenyl, benzofluorenyl, pyrenyl, triphenylenyl, fluoranthenyl, spirobifluorenyl, and the like.
The arylene group in the present invention is a general term for a divalent group remaining after two hydrogen atoms have been removed from the aromatic nucleus carbon of a substituted or unsubstituted aromatic compound molecule, and the number of carbon atoms of the arylene group is preferably C6 to C30, more preferably C6 to C20, still more preferably C6 to C12, and it may be a monocyclic arylene group, a polycyclic arylene group, or a fused ring arylene group. The monocyclic arylene group includes phenylene group and the like, but is not limited thereto; the polycyclic arylene group includes, but is not limited to, biphenylene, terphenylene, and the like; the condensed ring arylene group includes naphthylene, anthrylene, phenanthrylene, fluorenylene, pyrenylene, triphenylene, fluoranthenylene, phenylfluorenylene, and the like, but is not limited thereto.
The heteroaryl group in the invention refers to a general term of a group obtained by replacing one or more aromatic nucleus carbon atoms in an aryl group by heteroatoms, including but not limited to oxygen, sulfur, nitrogen or phosphorus atoms, the connecting site of the heteroaryl group can be positioned on ring-forming carbon atoms or ring-forming heteroatoms, wherein the number of carbon atoms is preferably C3-C30, further preferably C3-C20, more preferably C3-C12, and the heteroaryl group can be monocyclic heteroaryl, polycyclic heteroaryl or fused ring heteroaryl. The monocyclic heteroaryl group includes pyridyl, pyrazinyl, pyrimidinyl, triazinyl, furyl, thienyl, pyrrolyl, imidazolyl and the like, but is not limited thereto; the polycyclic heteroaryl group includes bipyridyl, phenylpyridyl, and the like, but is not limited thereto; the fused ring heteroaryl group includes, but is not limited to, quinolyl, isoquinolyl, indolyl, phenanthrolinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, acridinyl, 9, 10-dihydroacridinyl, phenothiazinyl, phenoxazine, xanthenyl, thioxanthyl, and the like.
Preferably, L1、L2Independently selected from single bond or any one of the following groups:
Figure BDA0002610741080000041
preferably, L1Selected from any one of the following groups:
Figure BDA0002610741080000042
preferably, L2Selected from a single bond or any of the following groups:
Figure BDA0002610741080000043
preferably, Ar is1And Ar2Ar described in3And Ar4Independently bonded to form a cyclic structure, or Ar1、Ar2、Ar3、Ar4Independently selected from any one of the following groups:
Figure BDA0002610741080000044
preferably, Ar is1、Ar2、Ar3、Ar4Independently selected from any one of the following groups:
Figure BDA0002610741080000051
or said Ar is1And Ar2Ar described in3And Ar4The individual bonds form the structure shown below:
Figure BDA0002610741080000052
preferably, the compound is selected from any one of the following compounds:
Figure BDA0002610741080000061
Figure BDA0002610741080000071
Figure BDA0002610741080000081
some specific structural forms of the arylamine compounds of the present invention are listed above, but the present invention is not limited to these listed chemical structures, and any substituent group as defined above based on the structure shown in formula (I) should be included.
The preparation method of the arylamine compound can be prepared by coupling reaction which is conventional in the field, for example, the preparation method can be prepared by the following synthetic routes, but the invention is not limited to the following steps:
the method comprises the following steps: containing Ar2Bromides of radicals with Ar1Reacting the amine compound of the group by Buchwald to obtain an intermediate (A);
Figure BDA0002610741080000082
step two: containing Ar4Bromides of radicals with Ar3Reacting the amine compound of the group by Buchwald to obtain an intermediate (B);
Figure BDA0002610741080000083
step three: and (3) carrying out Buchwald reaction on the compound (C) and the intermediate (B) to obtain an intermediate (D), and carrying out boration reaction on the intermediate (D) to obtain an intermediate (E).
Figure BDA0002610741080000084
Step four: and (3) carrying out Buchwald reaction on the intermediate (F) and the intermediate (A) to obtain an intermediate (G), and carrying out Suzuki reaction on the intermediate (G) and the intermediate (E) to obtain the target compound shown in the formula (I).
Figure BDA0002610741080000091
Wherein, X1、X2、X3、X4Independently selected from any one of I, Br and Cl.
The definition of each substituent is as described above and will not be described in detail herein.
The reaction conditions for the above reactions are not particularly limited in the present invention, and those well known to those skilled in the art may be used. The starting materials used in the above reactions are not particularly limited in the present invention, and may be commercially available products or prepared by methods known to those skilled in the art. The compound provided by the invention has the advantages of few synthesis steps, simple treatment and easiness in industrial production.
The invention also provides an organic electroluminescent device which comprises a cathode, an organic layer, an anode and a substrate, wherein the organic layer contains one or more of the arylamine compounds.
Regarding the organic electroluminescent device of the present invention, the organic layer may include a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., however, the structure of the organic electroluminescent device of the present invention is not limited by the above structure, and a plurality of organic layers may be omitted or simultaneously provided if necessary. For example, organic layers having the same function may be made into a stacked structure of 2 or more layers, for example, the hole transport layer may further include a first hole transport layer and a second hole transport layer, and the electron transport layer may further include a first electron transport layer and a second electron transport layer.
Preferably, the organic layer contains a hole transport layer containing one or more of the arylamine compounds.
Preferably, the hole transport layer includes a first hole transport layer and a second hole transport layer, and at least one of the first hole transport layer and the second hole transport layer contains one or more of the arylamine compounds.
With regard to the organic electroluminescent device of the present invention, any material used for the layer as in the prior art can be used for the layer other than the hole transport layer comprising the compound represented by (I).
As the anode of the organic electroluminescent device of the present invention, a material having a large work function can be used, and examples thereof include: metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals with oxides, e.g. ZnO: Al or SnO2Sb; conductive polymers, e.g. poly (3-methyl compounds), poly [3,4- (ethylene-1, 2-dioxy) compounds](PEDOT), polypyrrole, polyaniline, and the like, but are not limited thereto.
As the cathode of the organic electroluminescent device of the present invention, a material having a small work function can be used, and examples thereof include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, or alloys thereof; materials of multilayer construction, e.g. LiF/Al or LiO2Al, etc., but are not limited thereto.
As for the light emitting layer of the organic electroluminescent device of the present invention, a red light emitting material, a green light emitting material, or a blue light emitting material can be used as the light emitting material, and two or more light emitting materials can be mixed and used if necessary. The light-emitting material may be a host material alone or a mixture of a host material and a dopant material, and the light-emitting layer is preferably formed using a mixture of a host material and a dopant material.
The hole transport layer of the organic electroluminescent device of the present invention is required to have a suitable ion potential and a high hole mobility, and an organic material based on arylamine, a conductive polymer, a block copolymer having both a conjugated portion and a non-conjugated portion, and the like can be used, but the present invention is not limited thereto. In addition to the compounds of the formula (I) according to the invention, mention may be made of: 4,4 '-bis [ N- (1-naphthyl) -N-phenylamino ] biphenyl (NPB), 4,4,4 ″ -tris (N-carbazolyl) triphenylamine (TCTA), N' -bis (3-methylphenyl) -N, N '-diphenyl- [1, 1-biphenyl ] -4,4' -diamine (TPD), N '-bis (naphthalen-1-yl) -N, N' -diphenylbenzidine (a-NPD), and the like.
The electron transport layer of the organic electroluminescent device of the present invention is required to have a high electron affinity for an electron transport material, to be capable of efficiently transporting electrons, and to be less likely to generate impurities that act as traps during production and use. The electron-transporting material used in the electron-transporting layer is not particularly limited, and examples thereof include (1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, (2) aromatic heterocyclic compounds such as imidazole derivatives, benzimidazole derivatives, and phenanthroline derivatives, and (3) polymer compounds, but the invention is not limited thereto. Examples thereof include: tris (8-hydroxyquinoline) aluminum (Alq)3) Phenanthroline derivatives such as 1,3, 5-tris (1-naphthyl-1H-benzimidazol-2-yl) benzene (TPBI) and 4, 7-diphenyl-1, 10-phenanthroline (BPhen).
The electron injection layer of the organic electroluminescent device of the present invention is mainly used for improving the efficiency of injecting electrons from the cathode into the electron transport layer and the light-emitting layer, and is required to have the ability to transport electrons, and an alkali metal salt such as lithium fluoride and cesium fluoride, an alkaline earth metal salt such as magnesium fluoride, a metal oxide such as aluminum oxide, or the like can be used.
The present invention is not particularly limited to the thickness of each organic layer of the organic electroluminescent device, and may be any thickness commonly used in the art.
The organic electroluminescent device can be prepared by various methods such as solution coating such as spin coating and ink-jet printing or vacuum evaporation.
The starting materials used in the following examples are not particularly limited in their source, and may be commercially available products or prepared by methods known to those skilled in the art.
The mass spectrum used by the compound of the invention uses AXIMA-CFRplus matrix assisted laser desorption ionization flight mass spectrometer of Kratos Analytical company of Shimadzu corporation, and chloroform is used as a solvent;
elemental analysis using a Vario EL cube type organic element analyzer of Elementar corporation, Germany, the sample mass was 5 mg;
nuclear magnetic resonance (1HNMR) Using a Bruker-510 type nuclear magnetic resonance spectrometer (Bruker, Germany), 600MHz, CDCl3As solvent, TMS as internal standard.
Example 1: preparation of Compound 1
Figure BDA0002610741080000111
The method comprises the following steps: under the protection of nitrogen, 2-bromo-7-iodo-9, 9-dimethylfluorene (12.10g, 30.3mmol), diphenylamine (5.08g, 30mmol) and sodium tert-butoxide (3.75g, 39mmol) were dissolved in 150ml of dehydrated toluene, and a toluene solution of palladium acetate (0.07g, 0.30mmol) and tri-tert-butylphosphine (0.24g, 1.20mmol) was added thereto with stirring, followed by reflux reaction for 8 hours. After cooling, the reaction mixture was filtered through a celite/silica gel funnel, the organic solvent was removed from the filtrate by distillation under reduced pressure, and the concentrated solution was recrystallized from toluene and ethanol (10: 1) and filtered to obtain (10.04g, 22.8mmol) of intermediate (D-1) in 76% yield.
Step two: intermediate (D-1) (8.81g, 20mmol) was dissolved in DMSO and diborane pinacol ester (3.07g, 24mmol), KOAc (5.89g, 60mmol), Pd (dppf) Cl was added2(0.22g, 0.3mmol), nitrogen substitution three times, at 80 degrees C under 6h reaction. After completion of the reaction, the reaction mixture was extracted with toluene, dried over anhydrous sodium sulfate, and the crude product was passed through a silica gel column to obtain intermediate (E-1) (5.84g, 14.4mmol) in a yield of 72%.
Step three: (F-1) (9.00g, 25.3mmol), diphenylamine (4.23g, 25mmol) and sodium tert-butoxide (3.17g, 33mmol) were dissolved in 100ml of dehydrated toluene under nitrogen protection, and a toluene solution of palladium acetate (0.06g, 0.25mmol) and tri-tert-butylphosphine (0.20g, 1.00mmol) was added thereto with stirring, followed by reflux reaction for 8 hours. After cooling, filtration through a celite/silica funnel, the organic solvent was removed from the filtrate by distillation under reduced pressure, the concentrate was recrystallized from toluene and ethanol (10: 1), and filtration gave (8.32G, 18.75mmol) of intermediate (G-1) in 75% yield.
Step four: adding the intermediate into a reaction bottle under the protection of nitrogenG-1(5.42G, 12.2mmol), intermediate E-1(4.86G, 12mmol), K2CO3(4.98g, 36mmol), 150mL of toluene solvent was stirred. Adding catalyst Pd (PPh)3)4(0.14g, 0.12mmol), 60mL of distilled water, the temperature was raised to reflux and the reaction was stirred for 10 h. After the reaction was completed, 60mL of distilled water was added to complete the reaction. Filtration under reduced pressure gave crude compound 1, which was washed three times with distilled water and then recrystallized from toluene, ethanol (12: 1) to give (6.50g, 8.4mmol) of the title compound 1 in 70% yield.
Mass spectrum m/z: 768.48 (calculated value: 768.35). Theoretical element content (%) C58H44N2: c, 90.59; h, 5.77; and N, 3.64. Measured elemental content (%): c, 90.62; h, 5.76; and N, 3.64.1HNMR(600MHz,CDCl3): δ 7.92-7.86(m,5H),7.81(d,1H),7.70(d,1H),7.66(dd,1H),7.60-7.55(m,2H),7.51-7.46(m,2H),7.46-7.43(m,2H),7.42(d,1H),7.27-7.21(m,9H),7.19-7.15(m,2H),7.11-7.05(m,8H),7.00(tt,4H),1.70(s,3H),1.69(s, 3H). FIG. 1 shows the compound prepared in example 1 of the present invention1H NMR chart. The above results confirmed that the obtained product was the objective product.
Example 2: preparation of Compound 2
Figure BDA0002610741080000121
Compound 2 was obtained by replacing diphenylamine in the first step and the fourth step with an equimolar amount of N-phenyl-1-naphthylamine and performing the same procedures as in example 1.
Mass spectrum m/z: 868.50 (calculated value: 868.38). Theoretical element content (%) C66H48N2: c, 91.21; h, 5.57; and N, 3.22. Measured elemental content (%): c, 91.27; h, 5.56; and N, 3.20.1H NMR(600MHz,CDCl3): δ 9.06-9.03(m,1H),8.31(dd,1H),8.12(dd,1H),8.06(dd,1H),8.03(d,1H),8.01(dt,1H),7.90(ddd,2H),7.84(dt,1H),7.79(dd,2H),7.68(ddd,2H),7.62-7.58(m,1H),7.56(d,2H),7.54(d,1H),7.53-7.51(m,1H),7.49-7.41(m,7H),7.38(dd,2H),7.26-7.19(m,11H),7.04-6.96(m,3H),6.79(td,1H),1.79(s,3H),1.78(s, 3H). Drawing (A)2 is the compound prepared in example 2 of the invention1H NMR chart. The above results confirmed that the obtained product was the objective product.
Example 3: preparation of Compound 6
Figure BDA0002610741080000122
Compound 6 can be obtained by replacing diphenylamine in the first step and the fourth step with an equimolar amount of N-phenyl-4-benzidine and carrying out the same procedures as in example 1.
Mass spectrum m/z: 920.55 (calculated value: 920.41). Theoretical element content (%) C70H52N2: c, 91.27; h, 5.69; and N, 3.04. Measured elemental content (%): c, 91.34; h, 5.71; and N, 3.05. The above results confirmed that the obtained product was the objective product.
Example 4: preparation of Compound 17
Figure BDA0002610741080000123
Compound 17 can be obtained by replacing diphenylamine in the first step and the fourth step with an equimolar amount of N-phenyl-2 (9, 9-dimethyl-9H-fluorene) amine and carrying out the same procedures as in example 1.
Mass spectrum m/z: 1000.66 (calculated value: 1000.48). Theoretical element content (%) C76H60N2: c, 91.16; h, 6.04; and N, 2.80. Measured elemental content (%): c, 91.20; h, 6.05; n, 2.79.1H NMR(600MHz,CDCl3): δ 9.13(d,1H),8.67(dd,1H),8.07(dd,1H),8.02(d,1H),7.89(dd,1H),7.80(d,1H),7.79-7.75(m,2H),7.72-7.66(m,4H),7.65(d,1H),7.62-7.56(m,3H),7.54-7.47(m,7H),7.45(dd,1H),7.43-7.38(m,2H),7.29(dd,1H),7.27-7.21(m,6H),7.19(dd,1H),7.11-7.05(m,4H),7.04-6.97(m,3H),6.79(d,1H),1.82(s,3H), 1.70(s,3H), 1.74(s,3H),1.70(s,3H), 3H),1.74(s,3H), 3H, 1.70(s, 3H). FIG. 3 shows the compound prepared in example 4 of the present invention1H NMR chart. The above results confirmed that the obtained product was the objective product.
Example 5: preparation of Compound 20
Figure BDA0002610741080000131
Compound 20 can be obtained by replacing diphenylamine in the first step and the fourth step with an equimolar amount of N-phenyl-2-dibenzofuran amine and performing the same procedures as in example 1.
Mass spectrum m/z: 948.50 (calculated value: 948.37). Theoretical element content (%) C70H48N2O2: c, 88.58; h, 5.10; n, 2.95; o, 3.37. Measured elemental content (%): c, 88.60; h, 5.11; n, 2.96; and O, 3.36.1H NMR(600MHz,CDCl3): δ 8.08(dt,3H),7.96(dd,1H),7.93(dd,1H),7.81(d,1H),7.75(d,1H),7.70(dd,1H),7.62-7.56(m,4H),7.56-7.54(m,2H),7.54(q,2H),7.50(t,2H),7.44(td,2H),7.40(dd,1H),7.38(dd,1H),7.37-7.32(m,6H),7.29-7.21(m,6H),7.08(dd,4H),7.05-6.97(m,3H),6.80(d,1H),1.95(s,3H),1.83(s, 3H). FIG. 4 shows the compound prepared in example 5 of the present invention1H NMR chart. The above results confirmed that the obtained product was the objective product.
Example 6: preparation of Compound 27
Figure BDA0002610741080000132
Compound 27 was obtained by replacing diphenylamine in the first and fourth steps with an equimolar amount of deuterated diphenylamine and performing the same other steps as in example 1.
Mass spectrum m/z: 788.59 (calculated value: 788.48). Theoretical element content (%) C58H24D20N2: c, 88.28; h, 8.17; and N, 3.55. Measured elemental content (%): c, 88.29; h, 8.19; and N, 3.55.1H NMR(600MHz,CDCl3): δ 7.86(dd,2H),7.83(d,1H),7.80(d,1H),7.54(t,4H),7.45(d,1H),7.39(td,2H),7.33(d,1H),7.28(dd,1H),7.16(dd,1H),7.14-7.11(m,2H),7.10-7.06(m,2H),1.74(s,3H),1.70(s, 3H). FIG. 5 shows the compound prepared in example 6 of the present invention1H NMR chart. The above results confirmed that the obtained product was the objective product.
Example 7: preparation of Compound 29
Figure BDA0002610741080000133
Compound 29 can be obtained by replacing diphenylamine in the first step and the fourth step with an equimolar amount of N- (phenyl-2, 3,4,5,6-D5) -2-naphthylamine and carrying out the same procedures as in example 1.
Mass spectrum m/z: 878.57 (calculated value: 878.44). Theoretical element content (%) C66H38D10N2: c, 90.17; h, 6.65; n, 3.19. Measured elemental content (%): c, 90.20; h, 6.67; and N, 3.18. The above results confirmed that the obtained product was the objective product.
Example 8: preparation of Compound 33
Figure BDA0002610741080000141
Compound 33 was obtained by replacing diphenylamine in the first step and the fourth step with an equimolar amount of carbazole, and the other steps were the same as in example 1.
Mass spectrum m/z: 764.44 (calculated value: 764.32). Theoretical element content (%) C58H40N2: c, 91.07; h, 5.27; and N, 3.66. Measured elemental content (%): c, 91.08; h, 5.28; and N, 3.65.1H NMR(600MHz,CDCl3): Δ 8.39(dd,2H),8.33(dt,2H),8.18(d,1H),8.12(td,2H),8.07(d,1H),8.00(dd,1H),7.96-7.88(m,7H),7.86(d,1H),7.78-7.74(m,2H),7.74-7.70(m,2H),7.62-7.57(m,3H),7.54-7.47(m,2H),7.44-7.39(m,2H),7.38-7.29(m,6H),1.82(s,3H),1.80(s, 3H). FIG. 6 shows the compound prepared in example 8 of the present invention1H NMR chart. The above results confirmed that the obtained product was the objective product.
Example 9: preparation of Compound 36
Compound 36 was obtained by replacing diphenylamine in step one with an equimolar amount of carbazole and the other steps were the same as in example 1.
Mass spectrum m/z: 766.42 (calculated value: 766.33). Theoretical element content (%) C58H42N2: c, 90.83; h, 5.52; and N, 3.65. Measured elemental content (%): c, 90.84; h, 5.53; and N, 3.66.1H NMR(600MHz,CDCl3): δ 8.39(dd,1H),8.33(dd,1H),8.17(d,1H),8.11(dd,1H),8.03(d,1H),7.99(dd,1H),7.93(d,1H),7.91(dd,1H),7.90(d,1H),7.89(d,1H),7.89-7.87(m,1H),7.84(d,1H),7.77(dd,1H),7.60-7.55(m,3H),7.53-7.44(m,4H),7.44-7.39(m,1H),7.38-7.31(m,3H),7.24(t,4H),7.21-7.16(m,2H),7.09(d,2H),7.07(d,2H),7.03 (d,2H), 7.7.7.80 (d, 3H), 7.80 (m,3H), 7.80 (s, 3H). FIG. 7 shows a compound prepared in example 9 of the present invention1H NMR chart. The above results confirmed that the obtained product was the objective product.
Example 10: preparation of Compound 65
Figure BDA0002610741080000142
Compound 65 was obtained by replacing diphenylamine in the first step and the fourth step with an equimolar amount of 9, 10-dihydro-9, 9-dimethylacridine and carrying out the same procedures as in example 1.
Mass spectrum m/z: 848.54 (calculated value: 848.41). Theoretical element content (%) C64H52N2: c, 90.53; h, 6.17; and N, 3.30. Measured elemental content (%): c, 90.56; h, 6.17; and N, 3.30. The above results confirmed that the obtained product was the objective product.
Device examples 1-7: preparation of light emitting devices 1-7
The ITO glass substrate is placed in distilled water for cleaning for 2 times, ultrasonic cleaning is carried out for 30 minutes, after the cleaning of the distilled water is finished, solvents such as isopropanol, acetone, methanol and the like are sequentially subjected to ultrasonic cleaning and then dried, the substrate is transferred into a plasma cleaning machine, the substrate is cleaned for 5 minutes, and the substrate is sent to an evaporation machine. Evaporating a hole injection layer 2T-NATA/50nm layer by layer, evaporating a compound of the invention into a first hole transport layer/50 nm, evaporating an HTM into a second hole transport layer 20nm, evaporating a luminescent layer into a main body BH: doping BD 10%/30 nm, steamingPlated electron transport layer Alq325nm, electron injection layer LiF/1nm, cathode Al/300 nm.
Comparative device examples 1-2:
the difference from device examples 1-7 is that the first hole transport layer was the compounds HTL-1, HTL-2.
Device examples 8-10: preparation of light emitting devices 8-10
The ITO glass substrate is placed in distilled water for cleaning for 2 times, ultrasonic cleaning is carried out for 30 minutes, after the cleaning of the distilled water is finished, solvents such as isopropanol, acetone, methanol and the like are sequentially subjected to ultrasonic cleaning and then dried, the substrate is transferred into a plasma cleaning machine, the substrate is cleaned for 5 minutes, and the substrate is sent to an evaporation machine. Evaporating a hole injection layer 2T-NATA/50nm layer by layer, evaporating NPB (N-propyl bromide) to be a first hole transport layer/50 nm, evaporating a compound of the invention to be a second hole transport layer 20nm, evaporating a luminescent layer to be a main body BH (hydrogen bromide): BD 10%/30 nm doped, evaporated electron transport layer Alq325nm, electron injection layer LiF/1nm, cathode Al/300 nm.
Comparative device example 3:
the difference from device examples 8-10 is that the second hole transport layer is compound HTL-3.
In the invention, the preparation of the device is completed by adopting a vacuum evaporation system and continuously evaporating under the vacuum uninterrupted condition. The materials are respectively arranged in different evaporation source quartz crucibles, and the temperatures of the evaporation sources can be independently controlled. The thermal evaporation rate of the organic material or the doped parent organic material is generally set at 0.1nm/s, and the evaporation rate of the doped material is adjusted according to the doping ratio; the evaporation rate of the electrode metal is 0.4-0.6 nm/s. Placing the processed glass substrate into an OLED vacuum coating machine, wherein the vacuum degree of the system should be maintained at 5 x 10 in the film manufacturing process-5And (3) evaporating an organic layer and a metal electrode respectively by replacing a mask plate under Pa, detecting the evaporation speed by using an inficon SQM160 quartz crystal film thickness detector, and detecting the film thickness by using a quartz crystal oscillator. Testing software, computer, K2400 digital source meter manufactured by Keithley of America and PR788 spectral scanning luminance meter manufactured by Photo Research of America form a combined IVL testing system to test the organic electroluminescent deviceDriving voltage, luminous efficiency, CIE color coordinates. The lifetime was measured using the M6000 OLED lifetime test system from McScience. The environment of the test is atmospheric environment, and the temperature is room temperature.
The compounds involved in the inventive and comparative device examples are as follows:
Figure BDA0002610741080000161
the luminous performance of the organic electroluminescent device prepared by the embodiment of the invention is shown in the following table 1:
table 1 test data of light emitting property of organic electroluminescent device
Figure BDA0002610741080000162
The results show that the compound of the invention is used as a hole transport material in an organic electroluminescent device, can improve the luminous efficiency and the service life of the device, and is an organic luminescent material with excellent performance.
It is obvious that the above description of the embodiments is only intended to assist the understanding of the method of the invention and its core ideas. It should be noted that, for those skilled in the art, without departing from the principle of the present invention, several improvements and modifications can be made to the present invention, and these improvements and modifications also fall into the protection scope of the present invention.

Claims (8)

1. An arylamine compound characterized by having a structure represented by the following formula (I):
Figure FDA0002960178720000011
wherein L is1、L2Independently selected from single bond or any one of the following groups:
Figure FDA0002960178720000012
Ar1、Ar2、Ar3、Ar4independently selected from any one of the following groups: (ii) a
Figure FDA0002960178720000013
Or said Ar is1And Ar2Ar described in3And Ar4The individual bonds form the structure shown below:
Figure FDA0002960178720000014
2. an arylamine compound according to claim 1 wherein L is1Selected from any one of the following groups:
Figure FDA0002960178720000015
3. an arylamine compound according to claim 1 wherein L is2Selected from a single bond or any of the following groups:
Figure FDA0002960178720000016
4. an arylamine compound according to claim 1 wherein Ar is Ar1、Ar2、Ar3、Ar4Independently selected from any one of the following groups:
Figure FDA0002960178720000017
or said Ar is1And Ar2Ar described in3And Ar4The individual bonds form the structure shown below:
Figure FDA0002960178720000021
5. an arylamine compound according to claim 1, wherein the arylamine compound is any one compound selected from the group consisting of:
Figure FDA0002960178720000022
Figure FDA0002960178720000031
Figure FDA0002960178720000041
6. an organic electroluminescent device comprising a cathode, an organic layer containing one or more of the arylamine compounds according to any one of claims 1 to 5, an anode and a substrate.
7. The organic electroluminescent device according to claim 6, wherein the organic layer contains a hole transport layer containing one or more of the arylamine compounds according to any one of claims 1 to 5.
8. The organic electroluminescent device according to claim 7, wherein the hole transport layer comprises a first hole transport layer and a second hole transport layer, and at least one of the first hole transport layer and the second hole transport layer contains one or more of the arylamine compounds according to any one of claims 1 to 5.
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