CN114805323A - Aromatic amine compound having quaterphenyl structure and organic electroluminescent device comprising the same - Google Patents
Aromatic amine compound having quaterphenyl structure and organic electroluminescent device comprising the same Download PDFInfo
- Publication number
- CN114805323A CN114805323A CN202210549787.1A CN202210549787A CN114805323A CN 114805323 A CN114805323 A CN 114805323A CN 202210549787 A CN202210549787 A CN 202210549787A CN 114805323 A CN114805323 A CN 114805323A
- Authority
- CN
- China
- Prior art keywords
- substituted
- aromatic amine
- amine compound
- ring
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/625—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing at least one aromatic ring having 7 or more carbon atoms, e.g. azulene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses an aromatic amine compound containing a quaterphenyl structure and an organic electroluminescent device comprising the sameThe structural general formula of the aromatic amine compound is shown as formula I, wherein R in the formula I 1 、R 2 Each independently represents hydrogen and has carbon atom number of C 1 ～C 10 Alkyl group of (2), C 6 ～C 60 Aryl group of (2), C 5 ～C 60 Heteroaryl of (A), R 1 、R 2 May be linked to each other to form an alicyclic, aromatic, heteroaromatic, fused or hetero-fused ring, R 1 、R 2 Not simultaneously represent hydrogen; r 11 Represents hydrogen and carbon number is C 1 ～C 10 Alkyl group of (2), C 3 ～C 15 Cycloalkyl of (a); x represents a single bond, O or CH 2 . The aromatic amine compound of the present invention has a structure in which nitrogen atoms can be well protected, and an organic electroluminescent device comprising the aromatic amine compound as a hole transport layer and/or a light emission auxiliary layer has a low driving voltage, a high external quantum efficiency, and a long service life.
Description
Technical Field
The invention relates to the technical field of organic light-emitting semiconductors. And more particularly, to an aromatic amine compound having a quaterphenyl structure and an organic electroluminescent device including the same.
Background
The organic photoelectric material has diversity, low cost and excellent photoelectric performance in synthesis, so that the prepared display panel or lighting equipment has the advantages of wide visual angle, quick response, light weight, thin thickness, low voltage, low power consumption, high contrast, flexibility and the like.
An organic light emitting element generally includes a cathode, an electron injection layer, an electron transport layer, a light emitting layer, a hole transport layer, a hole injection layer, and an anode, and when a voltage is applied to both electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and the holes and the electrons migrate from both sides of the anode and the cathode toward the light emitting layer in the middle and meet each other to form excitons having localized electron-hole pairs in an excited energy state, which emit light by relaxation of a light emitting mechanism. It can be seen that a plurality of organic layers between the anode and the cathode bear different functions, so that the photoelectric properties of the material have difference, and the property difference of the organic material depends on the structural difference, so that the photoelectric property requirement of the material can be met through reasonable structural segments.
Currently, OLED materials have been widely used in electronic devices such as mobile phones and tablet computers, and gradually expanded to large-sized display devices such as televisions. However, in order to obtain better display effect and wider application range, the light emitting efficiency and the service life of the OLED light emitting element need to be further improved, and the driving voltage needs to be further reduced. The improvement of the performance of the light emitting device not only requires the improvement of the device structure and the manufacturing process, but also requires the innovation of the high-performance OLED material.
In the organic electroluminescent device, the hole transport rate directly affects the driving voltage of the organic electroluminescent device. The faster the hole transport rate, the smaller the driving voltage, and the slower the hole transport rate, the larger the driving voltage. As the driving voltage increases, the power consumption of the device also increases. The hole transport layer in the organic electroluminescent device has the greatest influence on the hole transport rate, and therefore, it is very important to improve the hole transport rate of the hole transport layer material. With the continuous development of organic electroluminescent devices and materials, light-emitting auxiliary layers are developed in the devices. The light-emitting auxiliary layer serves to block electrons transferred from the light-emitting layer from entering the hole transport layer. In addition, the light-emitting auxiliary layer has higher hole transmission rate, and is beneficial to improving the driving voltage of the organic electroluminescent device. Therefore, it is desired to develop a new material having a suitable HOMO level and a fast hole transport efficiency.
Disclosure of Invention
Based on the above facts, it is an object of the present invention to provide an aromatic amine compound having a quaterphenyl structure and an organic electroluminescent device comprising the same, which have a low driving voltage, a high external quantum efficiency and a long lifetime by providing a compound in which a nitrogen atom in the structure can be well protected, and an organic electroluminescent device comprising the same as a hole transport layer and/or a light emission auxiliary layer.
In one aspect, the present invention provides an aromatic amine compound containing a quaterphenyl structure, wherein the structural formula of the aromatic amine compound is shown in formula i:
wherein:
Ar 1 represents a carbon number of C 6 ～C 60 Substituted or unsubstituted aryl of (2), having the number of carbon atoms of C 6 ～C 60 Substituted or unsubstituted heteroaryl of (1), having the number of carbon atoms of C 6 ～C 60 Substituted or unsubstituted condensed ring aryl of (2), C 5 ～C 60 Substituted or unsubstituted hetero-condensed ring aryl group of (1), having carbon atom number C 3 ～C 30 Wherein, Ar is one of substituted or unsubstituted cycloalkyl groups of (A), wherein 1 Each substituent in (A) may be the same or different, and each substituent is independently selected from deuterium, halogen, and C 1 ～C 10 Alkyl group of (2), C 6 ～C 60 Aryl group of (2), C 6 ～C 60 With condensed ring aryl or with carbon number C 3 ～C 30 Wherein two or more substituents may be linked to each other to form an alicyclic ring, an aromatic ring or a condensed ring;
R 1 、R 2 each independently represents hydrogen and has carbon atom number of C 1 ～C 10 Alkyl group of (2), C 6 ～C 60 Aryl or C 5 ～C 60 Wherein R is 1 、R 2 May be linked to each other to form an alicyclic, aromatic, heteroaromatic, fused or hetero-fused ring, and R 1 、R 2 Not simultaneously represent hydrogen;
R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 each independently represents hydrogen, deuterium, or C 1 ～C 10 Alkyl group of (2), C 3 ～C 15 Cycloalkyl group of (C) 2 ～C 10 Alkenyl or C 6 ～C 60 And R is one of the aryl groups of (1), and 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 two or more of them may be linked to each other to form an alicyclic ring, an aromatic ring or a condensed ring;
R 11 represents hydrogen and carbon number is C 1 ～C 10 Alkyl or C 3 ～C 15 One of cycloalkyl groups of (a);
x represents a single bond, O or CH 2 One of (1);
L 1 、L 2 、L 3 each independently represents a single bond,
And any one or more non-adjacent C on the ring of the group may be substituted with N, and any one H may be substituted with F, D, alkyl or cycloalkyl;
the hydrogens on the ring structure of the compounds of formula I may each independently be replaced with deuterium.
It will be appreciated that L is exemplified above 1 、L 2 、L 3 In the group represented, when L 1 、L 2 、L 3 Are each selected from
In these groups, any two positions on the benzene ring may be used as the connecting sites.
Further, the compound shown in the formula I is one of the following structures shown in the formulas I-1 to I-10:
wherein Ar is 1 Represents a carbon number of C 6 ～C 60 Substituted or unsubstituted aryl group of (2), number of carbon atomsIs C 6 ～C 60 Substituted or unsubstituted heteroaryl of (1), having the number of carbon atoms of C 6 ～C 60 Substituted or unsubstituted condensed ring aryl of (2), having carbon number C 5 ～C 60 Substituted or unsubstituted hetero-condensed ring aryl group of (1), having carbon atom number C 3 ～C 30 Wherein, Ar is one of substituted or unsubstituted cycloalkyl groups of (A), wherein 1 Each substituent in (A) may be the same or different, and each substituent is independently selected from deuterium, halogen, and C 1 ～C 10 Alkyl group of (2), C 6 ～C 60 Aryl group of (2), C 6 ～C 60 With condensed ring aryl or with carbon number C 3 ～C 30 Wherein two or more substituents may be linked to each other to form an alicyclic ring, an aromatic ring or a condensed ring;
R 11 represents hydrogen and carbon number is C 1 ～C 10 Alkyl or C 3 ～C 15 One of cycloalkyl groups of (a);
L 1 、L 2 、L 3 each independently represents a single bond or
And any one or more non-adjacent C on the ring of the group may be substituted with N, and any one H may be substituted with F, D, alkyl or cycloalkyl;
the hydrogens on the ring structure of the compounds of formula I-1 to formula I-10 may each independently be replaced by deuterium.
Further, said L 1 Represents a single bond.
Further, said Ar 1 Represents:
Further, the cycloalkyl is selected from one of cyclobutyl, cyclopentyl, cyclohexyl or adamantane.
Further, the alkyl is C 1 ～C 10 Straight-chain alkyl or C 1 ～C 10 One of the branched alkyl groups.
Further, the compound shown in the formula I is selected from any one of the following compounds:
in another aspect, the present invention provides an organic electroluminescent device, including an anode, a hole transport region, a light emitting layer, an electron transport region, and a cathode sequentially disposed on a substrate; wherein the hole transport region comprises one or more aromatic amine compounds as described above.
Further, the hole transport region comprises a hole transport layer and a light-emitting auxiliary layer, the light-emitting auxiliary layer is positioned between the hole transport layer and the light-emitting layer, and one or more aromatic amine compounds are contained in the light-emitting auxiliary layer and/or the hole transport layer.
Further, when the organic electroluminescent device is a red or green organic electroluminescent device, one or more of the aromatic amine compounds are included in the light-emission auxiliary layer.
Further, the electron transport region includes an electron transport layer and an electron injection layer.
The invention has the following beneficial effects:
the aromatic amine compound provided by the invention is an aromatic amine compound containing a quaterphenyl structure, has high hole transport rate, can be used as a hole transport layer and also can be used as a light-emitting auxiliary layer, and is beneficial to reducing the driving voltage of a device. The thermal stability of the compound is improved by introducing a quaterphenyl structure into the molecule of the aromatic amine compound, which is beneficial to prolonging the service life of an organic electroluminescent device using the aromatic amine compound. In addition, in the aromatic amine compound, the phenyl group at the ortho position of the nitrogen atom connected with the quaterphenyl structure can effectively protect positive ions generated by the nitrogen atom, and is beneficial to improving the hole transport efficiency and stability, thereby playing roles in reducing the driving voltage of a device and improving the external quantum efficiency. And the phenyl group at the para position of the nitrogen atom can increase the electron cloud density of the compound, improve the conjugation degree and further improve the service life of the device. In addition, the compound has a proper HOMO energy level, and is beneficial to improving the hole transport efficiency and blocking the migration of electrons to the hole transport layer. Therefore, the organic electroluminescent device comprising the compound has a low driving voltage, high external quantum efficiency, and a long lifespan.
Drawings
The following describes embodiments of the present invention in further detail with reference to the accompanying drawings.
Fig. 1 shows a schematic view of the structure of an organic electroluminescent device containing the aromatic amine compound of the present invention.
FIG. 2 shows a mass spectrum of the compound shown in Synthesis example 2.
FIG. 3 shows a mass spectrum of the compound shown in Synthesis example 3.
FIG. 4 shows a mass spectrum of the compound shown in Synthesis example 32.
FIG. 5 shows a mass spectrum of the compound shown in Synthesis example 39.
FIG. 6 shows a mass spectrum of a compound shown in Synthesis example 44.
FIG. 7 shows a mass spectrum of the compound shown in Synthesis example 45.
Description of the drawings: 1-substrate, 2-anode, 3-hole transport layer, 4-luminescence auxiliary layer, 5-luminescent layer, 6-electron transport layer, 7-electron injection layer and 8-cathode.
Detailed Description
In order to more clearly illustrate the invention, the invention is further described below with reference to preferred embodiments and the accompanying drawings. Similar parts in the figures are denoted by the same reference numerals. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
The compound of the present invention is suitable for use in a light-emitting element, a display panel, and an electronic device, particularly in an organic electroluminescent device. The electronic device according to the present invention is a device including at least one layer containing at least one organic compound, and the device may also contain an inorganic material or a layer formed entirely of an inorganic material. The electronic device is preferably an organic electroluminescent device (OLED), an organic integrated circuit (O-IC), an organic field effect transistor (O-FET), an organic thin film transistor (O-TFT), an organic light emitting transistor (O-LET), an organic solar cell (O-SC), an organic dye sensitized solar cell (O-DSSC), an organic optical detector, an organic photoreceptor, an organic field quench device (O-FQD), a light emitting electrochemical cell (LEC), an organic laser diode (O-laser) and an organic plasma emitter. The electronic device is preferably an organic electroluminescent device (OLED). A schematic diagram of an exemplary organic electroluminescent device is shown in fig. 1.
Experimental part
However, the scope of the present invention, which is modified to various forms and numbers according to the examples and comparative examples of the present invention, is not to be construed as being limited to the examples and comparative examples described in detail below, and the examples and comparative examples of the present invention are provided to more fully explain the present invention to those skilled in the art.
The aromatic amine compound of the present invention is produced by a typical reaction such as a Buhward-Hartvisch coupling reaction, Suzuki coupling reaction, and Heck coupling reaction.
Synthesis examples of some aromatic amine compounds:
(1) synthesizing an intermediate:
adding SUB1-X (0.05mol) and SUB2-X (0.05mol) into a 500ml three-necked bottle under the protection of nitrogen, dissolving the mixture by using 250ml of toluene and 70ml of water, stirring the solution for 30min, adding potassium carbonate (0.1mol) and tetrakistriphenylphosphine palladium (5mmol), heating the solution to 90 ℃ and reacting the solution for 8h, cooling the solution to room temperature, adding water for separating the solution for quenching, and separating an organic phase by using column chromatography after spin drying to obtain an intermediate B-X, wherein the yield is 88% and the purity is 99%. MS (M/z) (M +) 385.
The intermediates a1-a50 used in the examples were prepared synthetically in the above manner.
(2) Aromatic amine compound synthesis example:
synthesis example 1
A1(4.02 g; 10mmol), B1(3.47 g; 9mmol), and sodium tert-butoxide (1.05 g; 11mmol) were added to toluene (50ml), and then, under nitrogen, bis-dibenzylidene was introduced together with palladium (274.J28mg, 0.30mmol) and tri-tert-butylphosphine (121.2mg, 0.6mmol), the reaction was heated to reflux and maintained for 10 hours, after cooling to room temperature, water was added to quench and separate the liquids, the organic phase was filtered and dried over anhydrous sodium sulfate, the solvent was removed, and the crude product was purified by column chromatography. The final product was C1:4.7g (yield: 74%), MS (M/z) (M +): 706.
Synthesis example 2
The procedure is as in example 1, except that A2(5.26 g; 10mmol), B2(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C2:4.11g (yield: 55%), MS (M/z) (M +): 830.
Synthesis example 3
The procedure is as in example 1, except that A3(5.24 g; 10mmol), B3(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C2:4.99g (yield: 67%), MS (M/z) (M +): 828.
Synthesis example 4
The procedure is as in example 1, except that A4(4.16 g; 10mmol), B4(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C4:4.92g (yield: 76%), MS (M/z) (M +): 720.
Synthesis example 5
The procedure is as in example 1, except that A5(5.18 g; 10mmol), B5(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C5:4.96g (yield: 67%), MS (M/z) (M +): 822.
Synthesis example 6
The procedure is as in example 1, except that A6(6.36 g; 10mmol), B6(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C6:4.48g (yield: 53%), MS (M/z) (M +): 940.
Synthesis example 7
The procedure is as in example 1, except that A7(6 g; 10mmol), B7(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C7:6.35g (yield: 78%), MS (M/z) (M +): 904.
Synthesis example 8
The procedure is as in example 1, except that A8(4.51 g; 10mmol), B8(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C8:4.01g (yield: 59%), MS (M/z) (M +): 755.
Synthesis example 9
The procedure is as in example 1, except that A9(5.85 g; 10mmol), B9(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C9:4g (yield: 50%), MS (M/z) (M +): 889.
Synthesis example 10
The procedure is as in example 1, except that A10(5.02 g; 10mmol), B10(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C10:5.08g (yield: 70%), MS (M/z) (M +): 806.
Synthesis example 11
The procedure is as in example 1, except that A11(4.52 g; 10mmol), B11(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C11:4.49g (yield: 66%), MS (M/z) (M +): 756.
Synthesis example 12
The procedure is as in example 1, except that A12(5.74 g; 10mmol), B12(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C12:4.9g (yield: 62%), MS (M/z) (M +): 878.
Synthesis example 13
The procedure is as in example 1, except that A13(6.06 g; 10mmol), B13(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C13:5.98g (yield: 73%), MS (M/z) (M +): 910.
Synthesis example 14
The procedure is as in example 1, except that A14(5.02 g; 10mmol), B14(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C14:4.5g (yield: 62%), MS (M/z) (M +): 806.
Synthesis example 15
The procedure is as in example 1, except that A15(5.74 g; 10mmol), B15(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C15:6.32g (yield: 80%), MS (M/z) (M +): 878.
Synthesis example 16
The procedure is as in example 1, except that A16(6.86 g; 10mmol), B16(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C16:5.35g (yield: 60%), MS (M/z) (M +): 990.
Synthesis example 17
The procedure is as in example 1, except that A17(6.17 g; 10mmol), B17(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C17:5.14g (yield: 62%), MS (M/z) (M +): 921.
Synthesis example 18
The procedure is as in example 1, except that A18(4.52 g; 10mmol), B18(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C18:4.35g (yield: 64%), MS (M/z) (M +): 756.
Synthetic example 19
The procedure is as in example 1, except that A19(6.06 g; 10mmol), B19(3.62 g; 9mmol) are substituted for A1 and B1 to give the final product C19:6.67g (yield: 80%), MS (M/z) (M +): 927.
Synthesis example 20
The procedure is as in example 1, except that A20(4.86 g; 10mmol), B20(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C20:4.05g (yield: 57%), MS (M/z) (M +): 790.
Synthesis example 21
The procedure is as in example 1, except that A21(3.71 g; 10mmol), B21(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C21:3.4g (yield: 56%), MS (M/z) (M +): 675.
Synthesis example 22
The procedure is as in example 1, except that A22(5.26 g; 10mmol), B22(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C22:4.48g (yield: 60%), MS (M/z) (M +): 830.
Synthesis example 23
The procedure is as in example 1, except that A23(4.38 g; 10mmol), B23(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C23:5.34g (yield: 80%), MS (M/z) (M +): 742.
Synthesis example 24
The procedure is as in example 1, except that A24(4.38 g; 10mmol), B24(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C24:3.47g (yield: 52%), MS (M/z) (M +): 742.
Synthetic example 25
The procedure is as in example 1, except that A25(4.38 g; 10mmol), B25(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C25:3.67g (yield: 55%), MS (M/z) (M +): 742.
Synthesis example 26
The procedure is as in example 1, except that A26(4.38 g; 10mmol), B26(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C26:4.27g (yield: 64%), MS (M/z) (M +): 742.
Synthesis example 27
The procedure is as in example 1, except that A27(4.38 g; 10mmol), B27(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C27:3.47g (yield: 52%), MS (M/z) (M +): 742.
Synthesis example 28
The procedure is as in example 1, except that A28(5.14 g; 10mmol), B28(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C28:5.6g (yield: 76%), MS (M/z) (M +): 818.
Synthetic example 29
The procedure is as in example 1, except that A29(3.61 g; 10mmol), B29(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C29:3.48g (yield: 58%), MS (M/z) (M +): 666.
Synthesis example 30
The procedure is as in example 1, except that A30(4.19 g; 10mmol), B30(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C30:4.58g (yield: 71%), MS (M/z) (M +): 716.
Synthetic example 31
The procedure is as in example 1, except that A31(5.24 g; 10mmol), B31(3.62 g; 9mmol) are substituted for A1 and B1 to give the final product C31:4.79g (yield: 63%), MS (M/z) (M +): 845.
Synthesis example 32
The procedure is as in example 1, except that A32(5.4 g; 10mmol), B32(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C32:4.1g (yield: 54%), MS (M/z) (M +): 844.
Synthetic example 33
The procedure is as in example 1, except that A33(5.4 g; 10mmol), B33(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C33:4.03g (yield: 53%), MS (M/z) (M +): 844.
Synthesis example 34
The procedure is as in example 1, except that A34(5.42 g; 10mmol), B34(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C34:4.04g (yield: 53%), MS (M/z) (M +): 846).
Synthesis example 35
The procedure is as in example 1, except that A35(5.02 g; 10mmol), B35(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C35:4.72g (yield: 65%), MS (M/z) (M +): 806.
Synthesis example 36
The procedure is as in example 1, except that A36(5.74 g; 10mmol), B36(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C36:4.43g (yield: 56%), MS (M/z) (M +): 878.
Synthesis example 37
The procedure is as in example 1, except that A37(5.54 g; 10mmol), B37(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C37:5.95g (yield: 77%), MS (M/z) (M +): 858.
Synthesis example 38
The procedure is as in example 1, except that A38(5.89 g; 10mmol), B38(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C38:6.19g (yield: 77%), MS (M/z) (M +): 893.
Synthesis example 39
The procedure is as in example 1, except that A39(5.24 g; 10mmol), B39(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C39:5.59g (yield: 75%), MS (M/z) (M +): 828.
Synthesis example 40
The procedure is as in example 1, except that A40(5.89 g; 10mmol), B40(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C40:4.1g (yield: 51%), MS (M/z) (M +): 893.
Synthesis example 41
The procedure is as in example 1, except that A41(4.52 g; 10mmol), B41(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C41:3.54g (yield: 52%), MS (M/z) (M +): 756.
Synthesis example 42
The procedure is as in example 1, except that A42(4.52 g; 10mmol), B42(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C42:5.38g (yield: 79%), MS (M/z) (M +): 756.
Synthetic example 43
The procedure is as in example 1, except that A43(4.52 g; 10mmol), B43(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C43:5.38g (yield: 79%), MS (M/z) (M +): 756.
Synthesis example 44
The procedure is as in example 1, except that A44(3.61 g; 10mmol), B44(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C44:3.05g (yield: 51%), MS (M/z) (M +): 665.
Synthesis example 45
The procedure is as in example 1, except that A45(3.75 g; 10mmol), B45(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C45:4.52g (yield: 74%), MS (M/z) (M +): 679.
Synthesis example 46
The procedure is as in example 1, except that A46(3.75 g; 10mmol), B46(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C46:3.54g (yield: 58%), MS (M/z) (M +): 679.
Synthetic example 47
The procedure is as in example 1, except that A47(3.75 g; 10mmol), B47(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C47:3.79g (yield: 62%), MS (M/z) (M +): 679.
Synthetic example 48
The procedure is as in example 1, except that A48(3.92 g; 10mmol), B48(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C48:3.38g (yield: 54%), MS (M/z) (M +): 696.
Synthesis example 49
The procedure is as in example 1, except that A49(4.52 g; 10mmol), B49(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C49:4.69g (yield: 69%), MS (M/z) (M +): 756.
Synthesis example 50
The procedure is as in example 1, except that A50(3.75 g; 10mmol), B50(3.47 g; 9mmol) are substituted for A1 and B1 to give the final product C50:4.09g (yield: 67%), MS (M/z) (M +): 679.
Properties of the compound
HOMO energy level testing
The HOMO energy level was determined by cyclic voltammetry. The instrument model is as follows: ZENNIUM. Electrolyte solution: an electrolyte solution having a concentration of 0.1mol/L was prepared by using an ultra-dry methylene chloride or DMF solvent and adding tetrabutylammonium hexafluorophosphate thereto.
The test method comprises the following steps: 10ml of the prepared 0.1mol/L electrolyte was added to a50 ml beaker. Before testing, the solvent needs to be deoxygenated, the plastic tube is connected to a nitrogen pipeline, and the solvent is inserted for deoxygenation. After deoxygenation, the gas tube was removed from the solvent but not out of the bottle, ensuring that the test procedure was always a nitrogen environment. And sequentially testing the baseline, the sample and the ferrocene internal standard.
Thermal stability experiments:
each ampoule was filled with 1g of the compound of examples 1 to 50. And then sealing with a tube sealing machine. Respectively putting the sealed ampoule tubes into separate cavities of a thermal stabilizer, starting a vacuum system to pump the vacuum degree to 10 -5 Pa or less. The temperature of the cavity is set to 300 ℃, the heating time is 240 hours, and the heating is started. After the 240h experiment, grinding and sampling are respectively carried out to test the purity. When the purity of the compound is changed within 0.5%, the compound has good thermal stability, and the thermal stability test is passed.
The results of the above HOMO level test, thermal stability test, and the like are shown in table 1 below.
TABLE 1
As shown in table 1 above, the compound provided in the embodiment of the present invention has a suitable HOMO energy level, is beneficial to improving the hole transport efficiency, and has good thermal stability. The drive voltage, the external quantum efficiency and the service life of the device are improved.
Fabrication and characterization of OLEDs
Device embodiments
The organic electroluminescent device provided by the invention comprises an anode, a hole transmission area, a luminescent layer, an electron transmission area and a cathode which are sequentially arranged on a substrate;
further, the hole transport region includes a hole transport layer and a light emission auxiliary layer; the electron transport region includes an electron transport layer and an electron injection layer.
Further, the light-emitting layer is composed of a host and a doped guest, and the host of the light-emitting layer can be composed of one molecular material or multiple molecular materials.
The aromatic amine compound of the present invention may be used for one or more layers of the above-mentioned organic electroluminescent device, preferably for a hole transport layer and/or a light emission auxiliary layer material of the device.
The anode in the embodiment is made of anode materials commonly used in the art, such as ITO, Ag or a multilayer structure thereof. The hole transport unit adopts a hole transport material commonly used in the field, and F4TCNQ, HATCN, NDP-9 and the like are added for doping. The light emitting unit is made of a light emitting material commonly used in the art, and for example, the light emitting unit may be formed by doping a host material and an emitting guest material, and the emitting guest material may be an organic material such as a boron-nitrogen compound, or may be a metal complex (e.g., metal Ir, Pt, etc.). The electron transport unit uses electron transport materials commonly used in the art. The electron injection layer is made of an electron injection material commonly used in the art, such as Liq, LiF, Yb, and the like. The cathode is made of materials commonly used in the art, such as metallic Al, Ag or a mixture of metals (Ag-doped Mg, Ag-doped Ca, etc.).
The electrode preparation method and the deposition method of each functional layer in this embodiment are conventional methods in the art, such as vacuum thermal evaporation or inkjet printing, and are not described herein again, and only some process details and test methods in the preparation process are described below:
device example 1
In the preparation of a blue light device, first, a hole transport layer was formed by vacuum-depositing C1 and F4TCNQ (mass ratio 97:3) at a thickness of 120nm on an ITO layer (anode) formed on a substrate; secondly, depositing B-prime on the hole transport layer in vacuum with the thickness of 10nm to form a light-emitting auxiliary layer; on the above luminescence auxiliary layer again, BH was vacuum-deposited as a host and BD-01 as a dopant at a thickness of 20nm, and the ratio of 98: 2 weight ratio of the doped mixture to form a light-emitting layer; then, vacuum depositing ET-01 on the luminescent layer with the thickness of 30nm to form an electron transport layer; then depositing LiF on the electron transport layer with the thickness of 0.2nm to form an electron injection layer; and finally, depositing aluminum (Al) on the electron injection layer in a thickness of 150nm to form a cathode, and preparing the blue light organic electroluminescent device.
Device example 2
In the preparation of a green device, first, a hole transport layer was formed by vacuum deposition of HTL and F4TCNQ (mass ratio 97:3) at a thickness of 120nm on an ITO layer (anode) formed on a substrate, and then a light-emitting auxiliary layer was formed by vacuum deposition of C11 at a thickness of 30nm on the above hole transport layer; vacuum depositing GH1 and GH2 with the mass ratio of 4:6 as a host and Ir (phq)2tpy as a dopant on the light-emitting auxiliary layer at the thickness of 30nm again, and forming a mixture doped with the weight ratio of 97:3 to form a light-emitting layer; then, vacuum depositing ET-01 on the luminescent layer with the thickness of 40nm to form an electron transport layer; then depositing LiF on the electron transport layer with the thickness of 0.2nm to form an electron injection layer; and finally, depositing aluminum (Al) on the electron injection layer in a thickness of 150nm to form a cathode, and preparing the green organic electroluminescent device.
Device example 3
In the preparation of a red light device, first, on an ITO layer (anode) formed on a substrate, a hole transport layer was formed by vacuum deposition of HTL and F4TCNQ (mass ratio 97:3) at a thickness of 120 nm; secondly, vacuum depositing C31 on the hole transport layer with the thickness of 80nm to form a light-emitting auxiliary layer; depositing RH as a main body and RD-01 as a dopant on the luminescence auxiliary layer in a vacuum manner with the thickness of 30nm, and forming a luminescent layer by a mixture doped with 95:5 by weight ratio; then, vacuum depositing ET-01 on the light-emitting layer with the thickness of 40nm to form an electron transport layer; and depositing LiF on the electron transport layer in a thickness of 0.2nm to form an electron injection layer, and depositing aluminum (Al) on the electron injection layer in a thickness of 150nm to form a cathode, thereby preparing the red light organic electroluminescent device.
Preparing the compound into an organic electroluminescent device by adopting the method, wherein the blue-light organic electroluminescent device is prepared from C2, C3, C4, C5, C6, C7, C8, C9, C10 and substituted C1; preparing a green organic light-emitting device by replacing C11 with C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, C41, C42, C43, C44, C45, C46, C47, C48, C49 and C50; c32, C33, C34, C35, C36, C37, C38, C39 and C40 are used for replacing C31 to prepare the red organic light-emitting device.
Comparative device example
The organic electroluminescent device prepared from the comparative compound by the method is used as a device comparative example. The blue organic electroluminescent device is prepared by replacing C1 with comparative compound 1 as device comparative example 1, the blue organic electroluminescent device is prepared by replacing C11 with comparative compound 2 as device comparative example 2, and the red organic electroluminescent device is prepared by replacing C1 with comparative compound 3 as device comparative example 3.
The OLED devices described above were tested by standard methods. For this purpose, J is 10mA/cm 2 Determining the drive voltage, luminance, electroluminescence current efficiency (measured in cd/a) and external quantum efficiency (EQE, measured in percent) of the organic electroluminescent device as a function of the luminous density, calculated from a current/voltage/luminous density characteristic line (IVL characteristic line) exhibiting lambert emission characteristicsSpectra. The lifetime LT is defined as the time after which the luminance is changed from the initial light-emission luminance L when operating at the constant current J 0 Down to a specific ratio L 1 ；J＝50mA/cm 2 And L 1 The expression 90% means at 50mA/cm 2 In the down operation, the light emission luminance is decreased to its initial value L after time LT 0 Similarly, J ═ 20mA/cm 2 ，L 1 80% means at 20mA/cm 2 In the down operation, the light emission luminance is decreased to its initial value L after time LT 0 80% of the total.
The bond dissociation energy of the example compound and the comparative example compound can be calculated by a density functional theory method. Bond Dissociation Energy (BDE) is defined as the change in enthalpy of reaction of a chemical Bond cleavage process in a molecule, which reflects the Energy required for the Bond cleavage process. The stability of the compound can be judged by the BDE of each bond of the compound in the hole state. The greater the dissociation energy of the compound, the better the stability of the compound, and the less stable the compound.
Data for various OLED devices are summarized in tables 2-4. The examples are compared to the parameters of comparative example 1, comparative example 2 and comparative example 3, showing performance data for various OLED devices.
The test instrument and method for testing the performance of the OLED devices of the above examples and comparative examples are as follows:
the brightness was tested using a spectroscanner Photoresearch PR-635;
current density and lighting voltage: testing using a digital source table Keithley 2400;
and (3) life test: an LT-96ch life test apparatus was used.
The results of the performance tests of the above devices are shown in tables 2 to 4.
TABLE 2 blue light device Performance test results
TABLE 3 Green light device Performance test results
TABLE 4 Red light device Performance test results
As can be seen from the results of the device performance tests in tables 2 to 4, the organic electroluminescent devices of examples 1 to 50 containing an aromatic amine compound having a quaterphenyl structure according to the present invention have significantly improved external quantum efficiency and significantly reduced driving voltage, as compared to comparative examples 1 to 3. And at 20mA/cm 2 Or 50mA/cm 2 When in down operation, the brightness of the light is reduced to its initial value L 0 Of 95% or 90%, i.e. the service life, the example device is significantly longer than the comparative example device. The organic light-emitting device prepared by using the aromatic amine compound containing the quaterphenyl structure has the advantages that the BDE is remarkably increased due to the protection effect of the ortho-phenyl group on the nitrogen atom, the stability of the material is increased, and finally, the service life attenuation is greatly slowed down. By calculating the dominant conformations (shown in the following formulas) of the example compound and the comparative compound by a density functional theory method, it can be seen that the tetrabiphenyl structures contained in the invention are arranged in the same direction, the tetrabiphenyl structures arranged in the same direction enable the molecular arrangement to be more ordered, and the intermolecular stacking is better, so that when the tetrabiphenyl structures are used as a hole transport layer or a light emitting auxiliary layer, the method is beneficial to improving the hole transport and reducing the driving voltage, and finally the driving voltage of the examples in tables 2 to 4 is smaller than that of the comparative examples.
The dominant conformations of examples 1, 2, 3, 42, 44, 45 and comparative compound 1, comparative compound 2, comparative compound 3 are shown in the following order:
therefore, the organic electroluminescent device comprising the aromatic amine compound having a quaterphenyl structure of the present invention has a lower driving voltage, a higher external quantum efficiency, and a longer lifetime.
It should be understood that the above-mentioned embodiments of the present invention are only examples for clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention, and it will be obvious to those skilled in the art that other variations or modifications may be made on the basis of the above description, and all embodiments may not be exhaustive, and all obvious variations or modifications may be included within the scope of the present invention.
Claims (9)
1. An aromatic amine compound containing a quaterphenyl structure, wherein the structural formula of the aromatic amine compound is shown as a formula I:
wherein:
Ar 1 represents a carbon number of C 6 ～C 60 Substituted or unsubstituted aryl of (2), having the number of carbon atoms of C 6 ～C 60 Substituted or unsubstituted heteroaryl of (1), having the number of carbon atoms of C 6 ～C 60 Substituted or unsubstituted condensed ring aryl of (2), having carbon number C 5 ～C 60 Substituted or unsubstituted hetero-condensed ring aryl group of (1), having carbon atom number C 3 ～C 30 Wherein, Ar is one of substituted or unsubstituted cycloalkyl groups of (A), wherein 1 Wherein each substituent may be the same or different and each substituent is independently selectedFrom deuterium, halogen, having a number of carbon atoms C 1 ～C 10 Alkyl group of (2), C 6 ～C 60 Aryl group of (2), C 6 ～C 60 With condensed ring aryl or with carbon number C 3 ～C 30 Wherein two or more substituents may be linked to each other to form an alicyclic ring, an aromatic ring or a condensed ring;
R 1 、R 2 each independently represents hydrogen and has carbon atom number of C 1 ～C 10 Alkyl group of (2), C 6 ～C 60 Aryl or C 5 ～C 60 Wherein R is 1 、R 2 May be linked to each other to form an alicyclic, aromatic, heteroaromatic, fused or hetero-fused ring, and R 1 、R 2 Not simultaneously represent hydrogen;
R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 each independently represents hydrogen, deuterium, or C 1 ～C 10 Alkyl group of (2), C 3 ～C 15 Cycloalkyl group of (C) 2 ～C 10 Alkenyl or C 6 ～C 60 And R is one of the aryl groups of (1), and 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 two or more of them may be linked to each other to form an alicyclic ring, an aromatic ring or a condensed ring;
R 11 represents hydrogen and carbon number is C 1 ～C 10 Alkyl or C 3 ～C 15 One of cycloalkyl groups of (a);
x represents a single bond, O or CH 2 One of (1);
L 1 、L 2 、L 3 each independently represents a single bond,
And any one or more of the radicals are not adjacent to each other on the ringC may be substituted with N, any one H may be substituted with F, D, alkyl or cycloalkyl;
the hydrogens on the ring structure of the compounds of formula I may each independently be replaced with deuterium.
2. The aromatic amine compound of claim 1, wherein the compound of formula I is one of the following structures of formula I-1 to formula I-10:
wherein Ar is 1 Represents a carbon number of C 6 ～C 60 Substituted or unsubstituted aryl of (2), having the number of carbon atoms of C 6 ～C 60 Substituted or unsubstituted heteroaryl of (1), having the number of carbon atoms of C 6 ～C 60 Substituted or unsubstituted condensed ring aryl of (2), having carbon number C 5 ～C 60 Substituted or unsubstituted hetero-condensed ring aryl group of (1), having carbon atom number C 3 ～C 30 Wherein, Ar is one of substituted or unsubstituted cycloalkyl groups of (A), wherein 1 Wherein each substituent may be the same or different, and each substituent is independently selected from deuterium, halogen, and a group having carbon atoms of C 1 ～C 10 Alkyl group of (2), C 6 ～C 60 Aryl group of (2), C 6 ～C 60 With condensed ring aryl or with carbon number C 3 ～C 30 Wherein two or more substituents may be linked to each other to form an alicyclic ring, an aromatic ring or a condensed ring;
R 11 represents hydrogen and carbon number is C 1 ～C 10 Alkyl or C 3 ～C 15 One of cycloalkyl groups of (a);
L 1 、L 2 、L 3 each independently represents a single bond or
And any one or more non-adjacent C on the ring of the group may be substituted with N, and any one H may be substituted with F, D, alkyl or cycloalkyl;
the hydrogens on the ring structure of the compounds of formula I-1 to formula I-10 may each independently be replaced by deuterium.
3. The aromatic amine compound according to claim 1, wherein L is 1 Represents a single bond.
4. The aromatic amine compound according to claim 1, wherein Ar is Ar 1 Represents:
5. The aromatic amine compound according to claim 1 or 2, wherein the cycloalkyl group is selected from one of cyclobutyl, cyclopentyl, cyclohexyl, or adamantane.
6. The aromatic amine compound according to claim 1 or 2, wherein the alkyl group has a carbon number of C 1 ～C 10 Straight-chain alkyl or C 1 ～C 10 One of the branched alkyl groups.
7. The aromatic amine compound according to claim 1, wherein the compound represented by the formula i is selected from any one of the following compounds:
8. an organic electroluminescent device is characterized by comprising an anode, a hole transmission area, a luminescent layer, an electron transmission area and a cathode which are sequentially arranged on a substrate; wherein the hole transport region comprises one or more aromatic amine compounds as claimed in any one of claims 1 to 7.
9. The organic electroluminescent device as claimed in claim 8, wherein the hole transport region comprises a hole transport layer and a light-emitting auxiliary layer, the light-emitting auxiliary layer is disposed between the hole transport layer and the light-emitting layer, and the light-emitting auxiliary layer and/or the hole transport layer comprises one or more of the aromatic amine compounds.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210549787.1A CN114805323A (en) | 2022-05-20 | 2022-05-20 | Aromatic amine compound having quaterphenyl structure and organic electroluminescent device comprising the same |
| PCT/CN2022/100267 WO2023221231A1 (en) | 2022-05-20 | 2022-06-22 | Aromatic amine compound containing quaterphenyl structure and organic electroluminescent device comprising same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210549787.1A CN114805323A (en) | 2022-05-20 | 2022-05-20 | Aromatic amine compound having quaterphenyl structure and organic electroluminescent device comprising the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114805323A true CN114805323A (en) | 2022-07-29 |
Family
ID=82517307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210549787.1A Pending CN114805323A (en) | 2022-05-20 | 2022-05-20 | Aromatic amine compound having quaterphenyl structure and organic electroluminescent device comprising the same |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN114805323A (en) |
| WO (1) | WO2023221231A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115028623A (en) * | 2022-07-27 | 2022-09-09 | 广州追光科技有限公司 | Arylamine compound and application thereof in organic electronic device |
| WO2024066916A1 (en) * | 2022-09-29 | 2024-04-04 | 石家庄诚志永华显示材料有限公司 | Aromatic amine compound comprising quaterphenyl structure and organic electroluminescent device comprising same |
| CN118324733A (en) * | 2024-06-17 | 2024-07-12 | 浙江华显光电科技有限公司 | Organic compound, OLED (organic light-emitting diode) with organic compound and organic light-emitting device |
| DE102024102533A1 (en) | 2023-02-02 | 2024-08-08 | Rohm And Haas Electronic Materials Korea Ltd. | ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118005585B (en) * | 2024-01-16 | 2024-09-27 | 石家庄诚志永华显示材料有限公司 | Long-life organic electroluminescent compound and organic electroluminescent device comprising same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102519794B1 (en) * | 2017-05-31 | 2023-04-11 | 주식회사 동진쎄미켐 | Novel compound and organic electroluminescent divice including the same |
| KR102649025B1 (en) * | 2017-09-13 | 2024-03-20 | 주식회사 동진쎄미켐 | Novel compound and organic electroluminescent divice including the same |
| KR20220007307A (en) * | 2020-07-10 | 2022-01-18 | 주식회사 동진쎄미켐 | Novel compounds and organic electroluminescent device comprising the same |
-
2022
- 2022-05-20 CN CN202210549787.1A patent/CN114805323A/en active Pending
- 2022-06-22 WO PCT/CN2022/100267 patent/WO2023221231A1/en unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115028623A (en) * | 2022-07-27 | 2022-09-09 | 广州追光科技有限公司 | Arylamine compound and application thereof in organic electronic device |
| CN115028623B (en) * | 2022-07-27 | 2024-01-05 | 广州追光科技有限公司 | Arylamine compound and application thereof in organic electronic device |
| WO2024066916A1 (en) * | 2022-09-29 | 2024-04-04 | 石家庄诚志永华显示材料有限公司 | Aromatic amine compound comprising quaterphenyl structure and organic electroluminescent device comprising same |
| DE102024102533A1 (en) | 2023-02-02 | 2024-08-08 | Rohm And Haas Electronic Materials Korea Ltd. | ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME |
| CN118324733A (en) * | 2024-06-17 | 2024-07-12 | 浙江华显光电科技有限公司 | Organic compound, OLED (organic light-emitting diode) with organic compound and organic light-emitting device |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2023221231A1 (en) | 2023-11-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6025959B2 (en) | 2-Azatriphenylene materials for organic light-emitting diodes | |
| CN114805323A (en) | Aromatic amine compound having quaterphenyl structure and organic electroluminescent device comprising the same | |
| Zhuang et al. | Synthesis, characterization, physical properties, and blue electroluminescent device applications of phenanthroimidazole derivatives containing anthracene or pyrene moiety | |
| JP6357422B2 (en) | Organic electroluminescence device | |
| KR102174066B1 (en) | Organic compounds and organic light emitting diode device comprising the same | |
| TWI470056B (en) | Oled device with stabilized yellow light-emitting layer | |
| KR20170118113A (en) | Phosphorescent compound, manufacturing method and organic light emitting diode device | |
| US20210296594A1 (en) | Organic electroluminescent materials and devices | |
| Hu et al. | High-efficiency and long-lifetime deep-blue organic light-emitting diode with a maximum external quantum efficiency of 20.6% and CIEy of 0.04 | |
| JP2023153909A (en) | Organic electroluminescent element | |
| TW202210612A (en) | Organic compound of formula (i) for use in organic electronic devices, a composition comprising a compound of formula (iv) and at least one compound of formula (iva) to (ivd), an organic semiconductor layer comprising the compound or composition, an organic electronic device comprising the organic semiconductor layer, and a display device comprising the organic electronic device | |
| CN117263893A (en) | Organic compound containing dimethylfluorene structure and organic electroluminescent device containing same | |
| US20230320121A1 (en) | Organic electroluminescent device | |
| KR102175791B1 (en) | Organic compounds and organic light emitting diode device comprising the same | |
| KR102707603B1 (en) | Organic electroluminescent device | |
| CN111574428B (en) | Donor-receptor type compound and application of organic electroluminescent device thereof | |
| CN116925020A (en) | Aromatic amine compound and organic electroluminescent device comprising same | |
| CN112151682B (en) | Organic electroluminescent device comprising hole blocking layer and electron transport layer | |
| CN117229252A (en) | Aromatic amine compound containing spirofluorene structure and organic electroluminescent device containing same | |
| CN116969847A (en) | Aromatic amine compound and organic electroluminescent device comprising same | |
| KR20240107010A (en) | Organic electroluminescent device | |
| KR20230168981A (en) | Organic electroluminescent materials and devices | |
| KR20230061277A (en) | Organic electroluminescent device | |
| KR20240002222A (en) | Organic electroluminescent device | |
| KR20240068576A (en) | Organic electroluminescent device and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication |