CN116535323B - A triarylamine compound and an organic electroluminescent device containing the same - Google Patents
A triarylamine compound and an organic electroluminescent device containing the same Download PDFInfo
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- CN116535323B CN116535323B CN202310483965.XA CN202310483965A CN116535323B CN 116535323 B CN116535323 B CN 116535323B CN 202310483965 A CN202310483965 A CN 202310483965A CN 116535323 B CN116535323 B CN 116535323B
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- -1 triarylamine compound Chemical class 0.000 title claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 26
- 230000005525 hole transport Effects 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- 230000000903 blocking effect Effects 0.000 claims description 31
- 238000002347 injection Methods 0.000 claims description 23
- 239000007924 injection Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical group [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims 2
- 239000000463 material Substances 0.000 abstract description 51
- 238000001704 evaporation Methods 0.000 abstract description 6
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 5
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 5
- VUVGFTPMYJWXIG-UHFFFAOYSA-N 5,5-ditert-butyl-2-phenylcyclohexa-1,3-diene Chemical group C1=CC(C(C)(C)C)(C(C)(C)C)CC=C1C1=CC=CC=C1 VUVGFTPMYJWXIG-UHFFFAOYSA-N 0.000 abstract description 4
- 238000004220 aggregation Methods 0.000 abstract description 3
- 230000002776 aggregation Effects 0.000 abstract description 3
- 230000008020 evaporation Effects 0.000 abstract description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 2
- 125000005266 diarylamine group Chemical group 0.000 abstract description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 103
- 239000010408 film Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 229910052805 deuterium Inorganic materials 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000002346 layers by function Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000008204 material by function Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- MBHPOBSZPYEADG-UHFFFAOYSA-N 2-bromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=CC=C3C2=C1 MBHPOBSZPYEADG-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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- C07D333/76—Dibenzothiophenes
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- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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Abstract
The invention discloses a novel triarylamine compound and an organic electroluminescent device containing the same, wherein the novel triarylamine compound is modified at 9, 9-positions of fluorene, and other positions are not modified, so that good hole transport characteristics and proper HOMO/LUMO energy levels of the material are ensured. In the connected diarylamine, one aryl is 4, 4-di-tert-butyl biphenyl, and the other aryl is non-4, 4-di-tert-butyl biphenyl, so that the mobility of holes in three-dimensional different directions of molecular stacking can be finely adjusted, and the transverse current can be reduced while the mobility is ensured. At the same time, the introduction of tertiary butyl can inhibit aggregation of materials, reduce evaporation temperature, improve efficiency and service life of devices.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a novel organic compound and application thereof, and an organic electroluminescent device containing the compound.
Background
The OLED light-emitting device comprises a cathode, an anode and an organic layer in the middle, wherein the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer. For the organic layer, proper mobility and energy level are key factors for realizing effective and rapid transmission and recombination of electrons and holes between different layer materials to form excitons, and further light emission. At present, the OLED display technology has been applied to the fields of smart phones, tablet computers, televisions and the like. However, the low voltage, high efficiency, long lifetime of OLED devices remains a goal of product performance as compared to actual product application requirements. In order to realize the continuous improvement of the performance of the OLED device, the innovation of the structure and the manufacturing process of the OLED device is required, and the continuous research and innovation of the OLED material are required to prepare the OLED material with higher performance.
The OLED photoelectric materials can be classified into two main types in terms of use, namely, a charge transport layer material and a light emitting layer material, and further, the charge transport layer material can be further classified into an electron injection, a transport layer material, an electron blocking layer material, a hole injection, a transport layer material and a hole blocking layer material, and the light emitting layer material can be classified into a host material and a doped light emitting material. In order to manufacture high-performance OLED light emitting devices, various organic functional materials are required to have good photoelectric properties, for example, as a charge transport layer material, good carrier mobility, suitable HOMO/LUMO energy level, high glass transition temperature, and the like, and as a host material of a light emitting layer, a material is required to be stable to light and electricity, while appropriate HOMO/LUMO energy level, and the like.
The common OLED device structure comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and other film layers, namely an organic OLED material applied to the OLED device at least comprises a hole injection material, a hole transport material, a light emitting material, an electron transport material and the like, so that the material type and the collocation form have the characteristics of richness and diversity. In addition, for the collocation of OLED devices with different structures, the used OLED materials have stronger selectivity, and the performance of the same materials in the devices with different structures can be completely different. Therefore, according to the industrial application requirements of the current OLED device and the requirements of different functional film layers of the OLED device, the photoelectric characteristics of the device are required to be matched more appropriately, and the comprehensive characteristics of low voltage, high efficiency, long service life and the like of the device can be realized by selecting and matching materials or material combinations with high performance. In view of the actual demands of the current OLED display lighting industry, the development of OLED materials is far from sufficient, and it is important to develop higher performance organic functional materials in line with the requirements of panel manufacturers.
Disclosure of Invention
The invention aims to solve the technical problems, and discovers that the 9, 9-position of fluorene is modified, and other positions are not modified, so that good hole transport property and proper HOMO/LUMO energy level of the material are ensured. In the connected diarylamine, one aryl is 4, 4-di-tert-butyl biphenyl, and the other aryl is non-4, 4-di-tert-butyl biphenyl, so that the mobility of holes in three-dimensional different directions of molecular stacking can be finely adjusted, and the transverse current can be reduced while the mobility is ensured. At the same time, the introduction of tertiary butyl can inhibit aggregation of materials, reduce evaporation temperature, improve efficiency and service life of devices.
Specifically, the present invention provides:
1) A triarylamine compound for an organic electroluminescent device, characterized in that the compound is represented by formula (1):
Wherein R 1、R2 is each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, R 1、R2 may optionally be linked to each other to form a substituted or unsubstituted saturated or unsaturated ring, R 21、R22 is a substituted or unsubstituted tert-butyl group having 1 to 50 carbon atoms, R 31～R37 is the same or different, and is hydrogen or heavy hydrogen independently of each other,
Ar is an aryl or heteroaryl group selected from the group consisting of:
Wherein R 3、R4 is each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, R 3、R4 may optionally be linked to each other to form a substituted or unsubstituted saturated or unsaturated ring;
Wherein R 5 is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms;
Wherein R 6、R7 is each independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 20 carbon atoms, and
Provided that the compound is not a molecule of the following:
2) The triarylamine compound for an organic electroluminescent device according to 1), wherein each R 1、R2 is independently selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
3) The triarylamine compound for an organic electroluminescent device according to 1), wherein each R 1、R2 is independently selected from methyl and phenyl.
4) The triarylamine compound for an organic electroluminescent device according to 1), wherein when R 1、R2 are connected to each other to form a ring, the ring is selected from the following ring structures:
5) The triarylamine compound for an organic electroluminescent device according to 1), wherein Ar is an aryl or heteroaryl group selected from the group consisting of:
Wherein R 3、R4 is each independently selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, R 3、R4 may optionally be linked to each other to form a substituted or unsubstituted saturated or unsaturated ring;
Wherein R 5 is selected from substituted or unsubstituted aryl with 6-30 carbon atoms;
Wherein R 6、R7 is independently selected from hydrogen, substituted or unsubstituted aryl with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl with 2-20 carbon atoms.
6) The triarylamine compound for an organic electroluminescent device according to 1), wherein Ar is an aryl or heteroaryl group selected from the group consisting of:
Wherein R 3、R4 are each independently selected from methyl, phenyl, R 3、R4 optionally may be linked to each other to form
Wherein R 5 is phenyl;
Wherein each R 6、R7 is independently selected from hydrogen, phenyl, dibenzofuranyl.
7) The triarylamine compound for an organic electroluminescent device as set forth in claim 1, wherein the triarylamine compound is selected from the group consisting of the following structures:
8) An organic electroluminescent device, characterized in that the organic electroluminescent device comprises an anode, a cathode and at least one layer of organic film between the anode and the cathode, wherein the organic film contains the compound of any one of 1) to 7).
9) The organic electroluminescent device according to 8), wherein the organic thin film comprises any one or a combination of at least two of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an exciton blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and at least one of the hole transport layer and the electron blocking layer contains a compound of any one of 1) to 5).
10 The organic electroluminescent device according to 8) or 9), characterized in that the compound is used as a hole transport layer and/or an electron blocking layer for green light in the organic electroluminescent device.
Compared with the prior art, the invention has the beneficial effects of ensuring good hole transmission characteristics and proper HOMO/LUMO energy level of the material, reducing transverse current while ensuring mobility, inhibiting aggregation of the material, reducing evaporation temperature, improving efficiency and service life of the device.
Drawings
The accompanying drawings, which are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate embodiments of the application and together with the description serve to explain the application and do not constitute a limitation on the application. In the drawings:
FIG. 1 is a schematic diagram of an organic electroluminescent device to which the compound of the present invention is applied, wherein the structure of each layer of the device is represented as follows:
1. Transparent substrate layer, 2, ITO anode layer, 3, hole injection layer, 4, hole transport layer A,5, hole transport layer B (or electron blocking layer), 6, luminescent layer, 7, electron transport layer B (or hole blocking layer), 8, electron transport layer A,9, electron injection layer, 10, cathode reflection electrode layer.
Detailed Description
The principles and features of the present invention will be further illustrated by the following examples of various synthetic examples and device examples, which are provided for purposes of illustration only and are not intended to limit the scope of the invention. The species of the hydrogen atom in the molecule of the compound used in the present invention is not particularly limited, and for example, all of the hydrogen atoms in the molecule may be 1 H, or some or all of the hydrogen atoms may be 2 H (deuterium (deuterium) D).
Two routes are designed, and the products can be simply synthesized. Meanwhile, in the synthetic scheme 1, when two bromides are the same, the first step may be omitted, and the second step may be directly used while doubling the amount of the bromides. The present invention is directed to material synthesis in scheme 1.
Synthetic route 1 (route of choice according to the invention)
Scheme 2
Synthesis example 1
Synthesis of intermediate M1
2.81G (10.0 mmol,1.0 eq) of 2-amino-4, 4-di-tert-butylbiphenyl (a 1), 2.33g (10.0 mmol,1.0 eq) of 4-bromobiphenyl (a 2) were added to the flask, followed by 0.18g (0.2 mmol,0.02 eq) of tris (dibenzylideneacetone) dipalladium, 1.92g (20 mmol,2.00 eq) of sodium tert-butoxide. The reaction system was purged three times with nitrogen gas. Then, 0.8ml (0.8 mmol,0.08 eq) of a toluene solution (1 mol/L) of tri-tert-butylphosphine and 20ml of toluene were added through a syringe. Under the protection of nitrogen, heating and stirring are carried out, and the reaction is carried out for 10 hours at 100 ℃. The reaction was stopped, cooled to room temperature, 100ml of deionized water was added, and extracted three times with ethyl acetate. The solvent was removed by rotary evaporation, 20ml of ethanol was added, heated under reflux until complete dissolution, and the solid was precipitated by cooling, and 3.55g of intermediate M1 was obtained by filtration, with a yield of 82%. The molecular weight of the white solid, liquid phase mass spectrum, was found to be m/z=433.
Synthesis of HT 001:
3.25g (7.5 mmol,1.0 eq) of intermediate M1, 2.05g (7.5 mmol,1.0 eq) of 9, 9-dimethyl-2-bromofluorene (a 3) and 0.16g (0.15 mmol,0.02 eq) of tris (dibenzylideneacetone) dipalladium and 1.44g (15 mmol,2 eq) of sodium tert-butoxide were added. The reaction system was purged three times with nitrogen gas. Then, 0.6ml (0.6 mmol,0.08 eq) of a toluene solution (1 mol/L) of tri-tert-butylphosphine and 20ml of xylene were added through a syringe. Under the protection of nitrogen, heating and stirring are carried out, and the reaction is carried out for 12h at 140 ℃. The reaction was stopped, cooled to room temperature, 100ml of deionized water was added, and extracted three times with ethyl acetate. Spin-evaporating the solvent, separating with silica gel column, eluting with dichloromethane/petroleum ether (1:20), spin-drying the solvent, and vacuum drying to obtain 3.89g of the target product with 83% yield. The molecular weight of the white solid, liquid phase mass spectrum, was m/z=625.
Other Synthesis examples are similar to Synthesis example 1, and specific results of the other Synthesis examples are shown in Table 1 below
TABLE 1
Device example 1 manufacture of organic electroluminescent device used as hole transport layer Material
A glass substrate having a thickness of 30mm by 1.1mm and having an Indium Tin Oxide (ITO) transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then Ultraviolet (UV) -ozone cleaned for 30 minutes. The cleaned glass substrate was mounted on a substrate holder of a vacuum deposition apparatus, and vacuum was applied to 1×10 -5～1×10-6 Pa, and a HATCN Hole Injection Layer (HIL) was deposited on an ITO transparent electrode to a film thickness of 15nm. HT 005 was deposited as a Hole Transport Layer (HTL) on top of the hole injection layer, with a thickness of 60nm. Then, EB was deposited as an Electron Blocking Layer (EBL) on top of the hole transport layer, with a film thickness of 10nm. And then, co-evaporating an emitting layer (EML) with the film thickness of 20nm on the electron blocking layer, wherein the emitting layer (EML) adopts a multi-source co-evaporation mode to evaporate a main material and emitting materials (BH and BD) of the emitting layer, wherein the doping concentration of the emitting materials is 2%wt. Then, HB was deposited as a Hole Blocking Layer (HBL) on the light-emitting layer to have a film thickness of 5nm. Then, on the hole blocking layer, an electron transport material (ET) and lithium 8-hydroxyquinoline (Liq) were co-evaporated in a 1:1 ratio as an Electron Transport Layer (ETL), and the film thickness was 30nm. Liq was deposited as an Electron Injection Layer (EIL) on the ETL to have a film thickness of 1nm. Then, metal cathode aluminum (Al) was deposited on the EIL to have a film thickness of 100nm. The structure of the organic electroluminescent device of example 1 is shown in fig. 1, and fig. 1 also shows the stacking sequence and effect of each functional layer.
The OLED has in principle the following layer structure ITO substrate/Hole Injection Layer (HIL)/Hole Transport Layer (HTL)/Electron Blocking Layer (EBL)/light emitting layer (EML)/Hole Blocking Layer (HBL)/Electron Transport Layer (ETL)/Electron Injection Layer (EIL) and finally a cathode. The cathode is formed of an aluminum layer having a thickness of 100 nm. The exact structure of the OLED is shown in table 1.
Table 2 materials for OLED
Device example 1:
ITO (130)/HATCN (15)/HT 005 (60)/EB (10)/BH: BD (20, wt. 2%)/HB (5)/ET: liq (30, wt. 50%)/Liq (1)/Al (100).
Device examples 2-16 differ from device example 1 only in the replacement of HT 005 of the present invention used in the hole transport layer with other compounds of the present invention, as detailed in Table 3.
Comparative examples 1 to 3:
this comparative example differs from device example 1 in that HT in the organic electroluminescent device was modified to be well known in the art and commercially applied, and the resulting device performance test data is shown in Table 3.
The OLED was characterized by standard methods. For this purpose, electroluminescence spectra, current efficiency (measured in cd/a), power efficiency (measured in lm/W) and external quantum efficiency (EQE, measured in%) were determined, which were calculated as a function of luminescence density from current/voltage/luminescence density characteristic lines (IUL characteristic lines) exhibiting lambertian emission characteristics. The required voltage V1000 is determined at a luminance of 1000cd/m 2. CE1000 represents the current efficiency achieved at 1000cd/m 2. Finally, EQE1000 represents the external quantum efficiency at an operating luminance of 1000cd/m 2, and T95 represents the operating time for the device to fade to 95% at an initial luminance of 1000cd/m 2. The device performance of examples 1 to 16 of the present invention and comparative examples 1 to 3 are summarized in table 3.
TABLE 3 Table 3
It can be seen from the table that, compared with the prior art, using the material examples 1 to 16 of the present invention, it is possible to slightly improve the device efficiency and greatly improve the device lifetime while maintaining the driving voltage of the OLED. CE1000 of device example 1, where EB 037 was located, improved efficiency by 4.9% and lifetime by 20.4% compared to comparative example 2. Second, as can be seen from comparison of HT 026, HT 208 and HT 240, the replacement of hydrogen (H) atoms in the material of the present invention, partially or completely, with deuterium (D) atoms, will significantly increase the lifetime, and the ratio of the enhancement will increase with increasing deuteration rate, because the C-D bond is shorter relative to the C-H bond, thereby making the C-D bond more stable relative to the C-H bond, and thus increasing the lifetime of the device.
Device example 17 production of organic electroluminescent device used as hole transport layer Material
A glass substrate having a thickness of 30mm by 1.1mm and having an Indium Tin Oxide (ITO) transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then Ultraviolet (UV) -ozone cleaned for 30 minutes. The cleaned glass substrate was mounted on a substrate holder of a vacuum deposition apparatus, and vacuum was applied to 1×10 -5～1×10-6 Pa, and a HATCN Hole Injection Layer (HIL) was deposited on an ITO transparent electrode to a film thickness of 15nm. HT was deposited as a Hole Transport Layer (HTL) on top of the hole injection layer, with a film thickness of 60nm. Then, HT 102 was deposited as an Electron Blocking Layer (EBL) on top of the hole transport layer, with a film thickness of 40nm. And then, co-evaporating an emitting layer (EML) with the film thickness of 40nm on the electron blocking layer, wherein the emitting layer (EML) adopts a multi-source co-evaporation mode to evaporate a main material and emitting materials (GH and GD) of the emitting layer, wherein the doping concentration of the emitting material is 5%wt. Then, HB was deposited as a Hole Blocking Layer (HBL) on the light-emitting layer to have a film thickness of 5nm. Then, on the hole blocking layer, an electron transport material (ET) and lithium 8-hydroxyquinoline (Liq) were co-evaporated in a 1:1 ratio as an Electron Transport Layer (ETL), and the film thickness was 30nm. Liq was deposited as an Electron Injection Layer (EIL) on the ETL to have a film thickness of 1nm. Then, metal cathode aluminum (Al) was deposited on the EIL to have a film thickness of 100nm. The structure of the organic electroluminescent device of example 1 is shown in fig. 1, and fig. 1 also shows the stacking sequence and effect of each functional layer.
The OLED has in principle the following layer structure ITO substrate/Hole Injection Layer (HIL)/Hole Transport Layer (HTL)/Electron Blocking Layer (EBL)/light emitting layer (EML)/Hole Blocking Layer (HBL)/Electron Transport Layer (ETL)/Electron Injection Layer (EIL) and finally a cathode. The cathode is formed of an aluminum layer having a thickness of 100 nm. The exact structure of the OLED is shown in table 4.
Table 4 materials for OLED
Device example 17:
ITO (130)/HATCN (15)/HT (60)/HT 102 (40)/GH: GD (40, wt% 5)/HB (5)/ET: liq (30, wt% 50)/Liq (1)/Al (100).
Device examples 18-29 differ from device example 17 only in the replacement of the inventive HT 102 used in the electron blocking layer with other compounds of the invention, see in particular table 5.
Comparative examples 4 to 5:
This comparative example differs from device example 17 in that EB in the organic electroluminescent device was changed to EB-1, EB-2, which are well known in the art and commercially applied, and the resulting device performance test data are shown in table 5.
The OLED was characterized by standard methods. For this purpose, electroluminescence spectra, current efficiency (measured in cd/a), power efficiency (measured in lm/W) and external quantum efficiency (EQE, measured in%) were determined, which were calculated as a function of luminescence density from current/voltage/luminescence density characteristic lines (IUL characteristic lines) exhibiting lambertian emission characteristics. The required voltage V1000 is determined at a luminance of 1000cd/m 2. CE1000 represents the current efficiency achieved at 1000cd/m 2. Finally, EQE1000 represents the external quantum efficiency at an operating luminance of 1000cd/m 2, and T95 represents the operating time for the device to fade to 95% at an initial luminance of 10000cd/m 2. The device properties of examples 17 to 29 of the present invention and comparative examples 4 to 5 are summarized in table 5.
TABLE 5
It can be seen from the table that, compared to the prior art, using the material examples 17-29 of the present invention, it is possible to slightly improve the device efficiency and greatly improve the device lifetime while maintaining the driving voltage of the OLED. CE1000 of device example 21, as compared to comparative example 4, had an efficiency improvement of 10% and a lifetime improvement of 15.9% for HT 157. Second, comparing HT 157 and HT 252, it is known that replacing hydrogen (H) atoms in the material of the present invention with deuterium (D) atoms, in part or in whole, significantly improves lifetime (16%), because the C-D bonds are shorter relative to the C-H bonds, thereby making the C-D bonds more stable relative to the C-H bonds, and thus improving the lifetime of the device.
Claims (9)
1. A triarylamine compound for an organic electroluminescent device, characterized in that the compound is represented by formula (1):
Wherein R 1、R2 is independently selected from alkyl having 1 to 50 carbon atoms, alkoxy having 1 to 50 carbon atoms, aryl having 6 to 50 carbon atoms, heteroaryl having 2 to 50 carbon atoms, R 1、R2 is optionally capable of being linked to each other to form a saturated or unsaturated ring, and R 1、R2 is linked to each other to form a ring, wherein the ring is selected from the following ring structures:
R 21、R22 represents tert-butyl which is monosubstituted, polysubstituted or unsubstituted by heavy hydrogen, R 31～R37 are each identical or different and are each, independently of one another, hydrogen, heavy hydrogen,
Ar is an aryl or heteroaryl group selected from the group consisting of:
Wherein R 3、R4 is independently selected from alkyl group having 1-50 carbon atoms, alkoxy group having 1-50 carbon atoms, aryl group having 6-50 carbon atoms, heteroaryl group having 2-50 carbon atoms, R 3、R4 is optionally connected with each other to form saturated or unsaturated ring, R 3、R4 is optionally connected with each other to form
Wherein R 5 is selected from alkyl with 1-20 carbon atoms, alkoxy with 1-20 carbon atoms, aryl with 6-30 carbon atoms, and heteroaryl with 2-30 carbon atoms;
Wherein R 6、R7 is each independently selected from the group consisting of hydrogen, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, and
Provided that the compound is not a molecule of the following:
2. the triarylamine compound for an organic electroluminescent element according to claim 1, wherein each R 1、R2 is independently selected from an alkyl group having 1 to 30 carbon atoms and an aryl group having 6 to 30 carbon atoms.
3. The triarylamine compound for an organic electroluminescent device according to claim 1, wherein each R 1、R2 is independently selected from methyl, phenyl.
4. The triarylamine compound for an organic electroluminescent device according to claim 1, wherein Ar is an aryl or heteroaryl group selected from the group consisting of:
Wherein R 3、R4 is each independently selected from alkyl having 1 to 30 carbon atoms, aryl having 6 to 30 carbon atoms, R 3、R4 may optionally be linked to each other to form a saturated or unsaturated ring, R 3、R4 may optionally be linked to each other to form
Wherein R 5 is selected from aryl groups with 6-30 carbon atoms;
Wherein R 6、R7 is independently selected from hydrogen, unsubstituted aryl group with 6-30 carbon atoms, and heteroaryl group with 2-20 carbon atoms.
5. The triarylamine compound for an organic electroluminescent device according to claim 1, wherein Ar is an aryl or heteroaryl group selected from the group consisting of:
Wherein R 3、R4 are each independently selected from methyl, phenyl, R 3、R4 optionally may be linked to each other to form
Wherein R 5 is phenyl;
Wherein each R 6、R7 is independently selected from hydrogen, phenyl, dibenzofuranyl.
6. The triarylamine compound for an organic electroluminescent device of claim 1, wherein the triarylamine compound is selected from the group consisting of the following structures:
7. an organic electroluminescent device, comprising an anode, a cathode, and at least one organic thin film between the anode and the cathode, wherein the organic thin film contains the compound of any one of claims 1 to 6.
8. The organic electroluminescent device according to claim 7, wherein the organic thin film comprises any one or a combination of at least two of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an exciton blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and at least one of the hole transport layer and the electron blocking layer contains the compound according to any one of claims 1 to 4.
9. The organic electroluminescent device according to claim 7 or 8, wherein the compound is used as a hole transport layer and/or an electron blocking layer for green light in the organic electroluminescent device.
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