CN117843501A - Aromatic amine compound containing tetrabenamine structure and organic electroluminescent device containing aromatic amine compound - Google Patents

Aromatic amine compound containing tetrabenamine structure and organic electroluminescent device containing aromatic amine compound Download PDF

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CN117843501A
CN117843501A CN202211200073.6A CN202211200073A CN117843501A CN 117843501 A CN117843501 A CN 117843501A CN 202211200073 A CN202211200073 A CN 202211200073A CN 117843501 A CN117843501 A CN 117843501A
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substituted
unsubstituted
aromatic amine
amine compound
light
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刘嵩远
魏天宇
张景
郑双权
徐凌伟
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Priority to CN202211200073.6A priority Critical patent/CN117843501A/en
Priority to PCT/CN2023/116380 priority patent/WO2024066916A1/en
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Abstract

The invention discloses an aromatic amine compound containing a tetrabenamine structure and an organic electroluminescent device containing the aromatic amine compound. The structure of the aromatic amine compound is shown as a formula I; wherein, the compound takes the formula i as a mother nucleus and has the following advantages: on one hand, the parent nucleus has relatively large molecular weight, can effectively improve the glass transition temperature and the thermal stability of the aromatic amine compound, and on the other hand, the special connection mode of the parent nucleus can reduce the steric hindrance and improve the LUMO, the energy gap value and the T1 value of the aromatic amine compound; the aromatic amine compound provided by the invention is applied to a hole transport layer material or a light-emitting auxiliary layer of an organic electroluminescent device, the hole transport layer material or the light-emitting auxiliary layer material is more matched with the energy level of an adjacent organic layer, the light-emitting efficiency of the organic electroluminescent device can be obviously improved, the preparation process of the aromatic amine compound is simple and easy to implement, raw materials are easily available, and the aromatic amine compound is suitable for mass production and amplification;

Description

Aromatic amine compound containing tetrabenamine structure and organic electroluminescent device containing aromatic amine compound
Technical Field
The invention relates to the technical field of organic light-emitting semiconductors. And more particularly, to an aromatic amine compound including a tetrabenamine structure and an organic electroluminescent device including the same.
Background
The organic electroluminescent device is generally composed of 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, electrons and holes are injected from the cathode and the anode, respectively, under an applied electric field, and then move in opposite directions, holes are transported to the light emitting layer via the hole transport layer, electrons are transported to the light emitting layer via the electron transport layer, and electrons and holes meeting in the light emitting layer are recombined to form electron-hole pairs, i.e., excitons, and then exciton radiation transitions to generate light emission. Because the Highest Occupied Molecular Orbital (HOMO) value of the hole transport layer material is low, excitons generated in the light emitting layer are easy to diffuse to the interface of the hole transport layer or the hole transport layer side, and finally cause luminescence at the interface in the light emitting layer or charge imbalance in the light emitting layer, so that luminescence is generated at the interface of the hole transport layer, the color purity and efficiency of the organic electroluminescent device are reduced, and finally the luminous efficiency of the organic electroluminescent device is reduced and the service life of the organic electroluminescent device is shortened. The technical problems can be effectively avoided by improving the performance of the hole transport layer material or introducing a light-emitting auxiliary layer between the light-emitting layer and the hole transport layer. The light emitting auxiliary layer has an auxiliary hole transport layer function and can block electrons transferred from the cathode to confine electrons within the light emitting layer, increasing the utilization ratio of holes, thereby improving the light emitting efficiency and lifetime of the device.
However, the existing hole transport layer material and light-emitting auxiliary layer material have the common problems of poor energy level and energy collocation, and the like, so that the driving voltage is higher. In order to reduce the driving voltage of the organic electroluminescent device, the current common technical means is to introduce rigid planar conjugated structures such as naphthalene, fluorene, phenanthrene and the like into a hole transport layer material or a light-emitting auxiliary layer material of the organic electroluminescent device, wherein the structures have larger pi electron clouds, which are beneficial to reducing the driving voltage of the device, but the structures deepen the conjugation degree of organic molecules, so that the T1 of the hole transport layer material or the light-emitting auxiliary layer material is obviously reduced, when the energy transferred by a carrier of the light-emitting auxiliary layer cannot meet the light-emitting energy required by transition of the light-emitting layer, the efficiency of the organic electroluminescent device is obviously reduced, and the structures are easy to break bonds at high temperature or in an electrically excited state, so that the service life of the organic electroluminescent device is reduced. Therefore, development of a novel organic electroluminescent material is needed.
Disclosure of Invention
In view of the above, the present invention provides an aromatic amine compound having a tetrabiphenyl structure and an organic electroluminescent device including the same, which not only has relatively high HOMO, LUMO energy levels and high T1, but also has high glass transition temperature and high molecular thermal stability, and can be used as a hole transport layer material or a light emitting auxiliary layer material of the organic electroluminescent device, thereby effectively reducing the driving voltage of the organic electroluminescent device, improving the efficiency of the device and prolonging the lifetime of the device, and overcoming the defects of the prior art.
In order to achieve the aim of the invention, the invention adopts the following technical scheme: the first aspect of the invention provides an aromatic amine compound containing a tetrabiphenyl structure, wherein the structural formula of the aromatic amine compound is shown as formula I:
wherein the Ar is 1 、Ar 2 Each independently selected from substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 5 ～C 60 Heteroaryl, substituted or unsubstituted C 10 ～C 60 Substituted or unsubstituted C 9 ～C 60 Substituted or unsubstituted C 3 ～C 30 Any one of cycloalkyl groups of (a);
when said Ar is 1 Or Ar 2 When a substituent is present, the substituent is selected from deuterium, halogen, hydroxy, cyano, nitro, amino, carboxy or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, C 1 ～C 10 Alkyl, C of (2) 6 ～C 60 Aryl group of (C),C 5 ～C 60 Heteroaryl, C 10 ～C 60 Condensed ring aryl, C 9 ～C 60 Hetero-condensed ring aryl or C 3 ～C 30 Wherein two or more substituents may be the same or different and may be linked to each other to form an aliphatic ring, an aromatic ring, a heteroaromatic ring, a condensed ring or a heterocondensed ring;
the L is 2 Selected from single bonds, substituted or unsubstituted C 1 ～C 12 Alkylene, substituted or unsubstituted C 6 ～C 30 Arylene, substituted or unsubstituted C 6 ～C 30 Any one of heteroarylene groups of (a);
any one of the hydrogens on the compound of formula I may be each independently substituted with deuterium, alkyl, or cycloalkyl.
With reference to the first aspect, the Ar 1 The structural formula of (2) is shown as formula II:
wherein the R is 1 、R 2 Each independently selected from hydrogen, deuterium, substituted or unsubstituted C 1 ～C 10 Alkyl, substituted or unsubstituted C 3 ～C 10 Cycloalkyl, substituted or unsubstituted C 6 ～C 30 Aryl, substituted or unsubstituted C 5 ～C 30 Heteroaryl, substituted or unsubstituted C 1 ～C 6 Alkoxy, substituted or unsubstituted C 10 ～C 60 Substituted or unsubstituted C 9 ～C 30 Aralkyl, substituted or unsubstituted C 6 ～C 30 Aryloxy, substituted or unsubstituted C 6 ～C 30 Any one of the above-mentioned two or more groups may be linked to each other to form an aliphatic ring, an aromatic ring, a heteroaromatic ring, a condensed ring or a hetero condensed ring;
the a is selected from integers from 1 to 5; the b is selected from integers from 1 to 4;
the saidL 1 Selected from single bonds, O, S, substituted or unsubstituted C 1 ～C 12 Alkylene, substituted or unsubstituted C 6 ～C 30 Any one of arylene groups of (a);
any one of the hydrogens on the compound of formula II may be independently substituted with deuterium, alkyl or cycloalkyl.
In combination with the first aspect, the compound shown in the formula II is one of the structures shown in the following formulas II-1 to II-7:
wherein n is selected from integers from 1 to 4; the m is selected from integers from 1 to 3;
the L is 1 Selected from single bonds, O, S, substituted or unsubstituted C 1 ～C 12 Alkylene, substituted or unsubstituted C 6 ～C 30 Any one of arylene groups of (a);
the L is 2 Any one selected from single bond and O, S;
the X is selected from O, S, CR 3 R 4 、NR 5 Any one of them;
the R is 3 、R 4 Each independently selected from hydrogen, deuterium, substituted or unsubstituted C 1 ～C 10 Alkyl, substituted or unsubstituted C 6 ～C 30 Aryl, substituted or unsubstituted C 5 ～C 30 Heteroaryl, substituted or unsubstituted C 10 ～C 60 Substituted or unsubstituted C 6 ～C 30 Aralkyl, substituted or unsubstituted C 6 ～C 30 Aryloxy, substituted or unsubstituted C 6 ～C 30 Arylthio, R 3 、R 4 May be linked to each other to form an aliphatic ring, an aromatic ring, a heteroaromatic ring, a condensed ring, or a heterocondensed ring;
the R is 5 Selected from hydrogen, deuterium, substituted or unsubstituted C 1 ～C 10 Alkyl, substituted or unsubstituted C 6 ～C 30 Aryl of (a);
any one of the hydrogens on the compounds of formulas II-1 to II-7 may be each independently substituted with deuterium, alkyl or cycloalkyl.
With reference to the first aspect, the Ar 2 Selected from substituted or unsubstituted C 6 ～C 30 Aryl, substituted or unsubstituted C 5 ～C 30 Heteroaryl, substituted or unsubstituted C 10 ～C 30 Substituted or unsubstituted C 9 ～C 30 Substituted or unsubstituted C 3 ～C 15 Any one of cycloalkyl groups of (a).
With reference to the first aspect, the Ar 2 Selected from any one of the groups indicated by a-1 to a-92:
with reference to the first aspect, the L 2 Selected from single bond,Any one of the following.
It will be appreciated that the above-exemplified list is given when L 2 Selected from single bond,In any of these, the meaning is that of these groups, the benzene ring isAny position capable of bonding may be used as the attachment site.
With reference to the first aspect, the compound represented by formula i is selected from any one of the following compounds:
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the second aspect of the invention provides application of the aromatic amine compound in an organic electroluminescent device.
The third aspect of the present invention provides an organic electroluminescent device, comprising an anode, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport region and a cathode, which are sequentially disposed on a substrate; wherein the light-emitting auxiliary layer and/or the hole transport layer comprises one or more aromatic amine compounds as described above.
The beneficial effects of the invention are as follows:
the aromatic amine compound provided by the invention takes the formula i as a parent nucleus, on one hand, the parent nucleus has relatively large molecular weight, the glass transition temperature and the thermal stability of the aromatic amine compound can be effectively improved, on the other hand, the 3 rd position and the 5 th position of benzene connected with nitrogen are respectively replaced by biphenyl and monophenyl, the biphenyl connected with the 3 rd position is ortho-position substituted, the special mode is used for connection, the steric hindrance can be reduced, and the LUMO, the energy gap value and the T1 value of the aromatic amine compound are improved; the aromatic amine compound provided by the invention is applied to a hole transport layer material or a light-emitting auxiliary layer of an organic electroluminescent device, and the energy level of the hole transport layer material or the light-emitting auxiliary layer material is more matched with the energy level of an adjacent organic layer, so that the driving voltage of the organic electroluminescent device can be effectively reduced; the hole transport layer material or the light-emitting auxiliary layer material has relatively high LUMO and energy gap values, and can block electrons or excitons from leaving the light-emitting layer, so that the efficiency of the device is improved; the hole transport layer material or the light-emitting auxiliary layer material has a relatively high T1 value, and the energy transferred by the carriers of the hole transport layer or the light-emitting auxiliary layer can meet the light-emitting energy required by the transition of the light-emitting layer, so that the light-emitting efficiency of the organic electroluminescent device can be remarkably improved; the hole transport layer material or the light-emitting auxiliary layer material has higher glass transition temperature and thermal stability, can inhibit evaporation decomposition of the material, and effectively prolongs the service life of the device; overcomes the defects of the prior art.
The preparation process of the compound is simple and feasible, raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Drawings
The following describes the embodiments of the present invention in further detail with reference to the drawings.
Fig. 1 shows a schematic structure of an organic electroluminescent device containing the aromatic amine compound according to the present invention;
FIG. 2 shows the LOMO profile of aromatic amine compound C1;
fig. 3 shows a triplet energy level orbital profile of the aromatic amine compound C1;
FIG. 4 shows the LOMO profile of aromatic amine compound C2;
fig. 5 shows a triplet energy level orbital profile of the aromatic amine compound C2;
FIG. 6 shows the LOMO profile of aromatic amine compound C3;
FIG. 7 shows a triplet energy level orbital profile of aromatic amine compound C3;
FIG. 8 shows the LOMO profile of aromatic amine compound C4;
fig. 9 shows a triplet energy level orbital profile of the aromatic amine compound C4;
FIG. 10 shows the LOMO profile of aromatic amine compound C29;
FIG. 11 shows a triplet energy level orbital profile of aromatic amine compound C29;
FIG. 12 shows the LOMO profile of aromatic amine compound C180;
FIG. 13 shows a triplet energy level orbital profile of aromatic amine compound C180;
FIG. 14 shows the LOMO profile of aromatic amine compound C216;
fig. 15 shows a triplet energy level orbital profile of aromatic amine compound C216;
FIG. 16 shows the LOMO profile of aromatic amine compound C227;
fig. 17 shows a triplet energy level orbital profile of the aromatic amine compound C227.
Description of the drawings: 1-base plate, 2-anode, 3-hole transport layer, 4-luminescent auxiliary layer, 5-luminescent layer, 6-electron transport layer, 7-electron injection layer, 8-cathode.
Detailed Description
In order to more clearly illustrate the present invention, the present invention will be further described with reference to preferred embodiments and the accompanying drawings. Like parts in the drawings 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 that this invention is not limited to the details given herein. The examples and comparative examples of the present specification are provided to more fully explain the present specification to those skilled in the art, and according to the present specification, the examples and comparative examples may be modified into various different forms, and the scope of the present invention should not be limited to only the examples and comparative examples described in detail below.
The compound is suitable for light-emitting elements, display panels and electronic devices, and is especially suitable for organic electroluminescent devices. The electronic device of the invention is a device comprising a layer of at least one organic compound, which device may also comprise 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 emission device. The electronic device is preferably an organic electroluminescent device (OLED). A schematic structural diagram of an exemplary organic electroluminescent device is shown in fig. 1.
The aromatic amine compound of the present invention is prepared by using a representative reaction of a Buch-Hastey coupling reaction, a Suzuki coupling reaction or a Heck coupling reaction.
Example 1
This example provides an intermediate compound a, which is synthesized as follows:
e (21.78 g,0.11 mol), F (31.20 g,0.1 mol) and sodium carbonate (21.20 g,0.2 mol) were added under nitrogen protection to 300ml of a mixed solvent of toluene, ethanol and water, wherein the volume ratio of toluene, water and ethanol in the mixed solvent is 8:3:1, introduction of PdCl (PPh 3 ) 2 (1.40 g,2 mmol) was then heated to 80 ℃, refluxed for 5 hours, cooled to room temperature, added with 200ml of deionized water, stirred for 20min, separated, the organic phase filtered, dried over anhydrous sodium sulfate, the solvent was removed by rotary evaporation, and the crude product was purified by column chromatography. 23.10g (yield: 60%) of product A, MS (M/z) (M+): 385 were finally obtained.
The intermediate compounds a used in the following examples were each prepared in the above manner.
Example 2
The present example provides an aromatic amine compound C-1, which is synthesized as follows:
a (3.85 g,10 mmol), B-1 (4.38 g,10 mmol) and sodium tert-butoxide (1.06 g,11 mmol) were added to toluene (50 mL), then under nitrogen, bis-dibenzylideneacetone palladium (0.09 g,0.1 mmol) and tri-tert-butylphosphorus (0.08 g,0.2 mmol) were introduced, the reaction system was then heated to 110℃and refluxed for 8 hours, cooled to room temperature, quenched with water and separated, the organic phase was filtered and dried over anhydrous sodium sulfate, the solvent was removed by swirling, and the crude product was purified by column chromatography. Finally, 5.42g (yield: 73%) of the product C-1 was obtained, MS (M/z) (M+): 742.
Example 3
The present example provides an aromatic amine compound C-2, which is synthesized as follows:
the procedure is as in example 1 except that B-2 (4.58 g,10 mmol) is substituted for B-1 to give 6.40g (yield: 84%) of product C-2, MS (M/z) (M+): 762.
Example 4
The present example provides an aromatic amine compound C-3, which is synthesized as follows:
the procedure is as in example 1 except that B-3 (4.58 g,10 mmol) is substituted for B-1 to give final product C-3:6.02g (yield: 79%), MS (M/z) (M+): 762.
Example 5
The present example provides an aromatic amine compound C-4, which is synthesized as follows:
the procedure is as in example 1 except that B-4 (4.24 g,10 mmol) is substituted for B-1 to give final product C-4:5.97g (yield: 82%), MS (M/z) (M+): 728.
Example 6
The present example provides an aromatic amine compound C-9, which is synthesized as follows:
the procedure is as in example 1 except that B-9 (4.79 g,10 mmol) is substituted for B-1 to give the final product C-9:6.03g (yield: 77%), MS (M/z) (M+): 783.
Example 7
The present example provides an aromatic amine compound C-11, which is synthesized as follows:
the procedure is as in example 1 except that B-11 (4.51 g,10 mmol) is substituted for B-1 to give final product C-11:5.59g (yield: 74%), MS (M/z) (M+): 755.
Example 8
The present example provides an aromatic amine compound C-14, which is synthesized as follows:
the procedure is as in example 1 except that B-14 (4.69 g,10 mmol) is substituted for B-1 to give 6.18g (yield: 80%) of the product C-14, MS (M/z) (M+): 773.
Example 9
The present example provides an aromatic amine compound C-16, which is synthesized as follows:
the procedure is as in example 1 except that A-16 (4.02 g,10 mmol) is substituted for A and B-16 (5.26 g,10 mmol) is substituted for B-1, to give final product C-16:6.01g (yield: 71%), MS (M/z) (M+): 847.
Example 10
The present example provides an aromatic amine compound C-17, which is synthesized as follows:
the procedure is as in example 1 except that B-17 (5.75 g,10 mmol) is substituted for B-1 to give 6.68g (yield: 76%) of the product C-17, MS (M/z) (M+): 879.
Example 11
The present example provides an aromatic amine compound C-20, which is synthesized as follows:
the procedure is as in example 1 except that B-20 (4.96 g,10 mmol) is substituted for B-1 to give the final product C-20:5.76g (yield: 72%), MS (M/z) (M+): 800.
Example 12
The present example provides an aromatic amine compound C-21, which is synthesized as follows:
the procedure is as in example 1 except that B-21 (5.24 g,10 mmol) is substituted for B-1 to give final product C-21:5.80g (yield: 70%), MS (M/z) (M+): 828.
Example 13
The present example provides an aromatic amine compound C-22, which is synthesized as follows:
the procedure is as in example 1 except that B-22 (5.73 g,10 mmol) is substituted for B-1 to give 6.14g (yield: 70%) of the product C-22, MS (M/z) (M+): 877.
Example 14
The present example provides an aromatic amine compound C-23, which is synthesized as follows:
the procedure is as in example 1 except that B-23 (5.73 g,10 mmol) is substituted for B-1 to give final product C-23:7.19g (yield: 82%), MS (M/z) (M+): 877.
Example 15
The present example provides an aromatic amine compound C-26, which is synthesized as follows:
the procedure is as in example 1 except that B-26 (4.51 g,10 mmol) is substituted for B-1 to give final product C-26:5.89g (yield: 78%), MS (M/z) (M+): 755.
Example 16
The present example provides an aromatic amine compound C-29, which is synthesized as follows:
the procedure is as in example 1 except that B-29 (4.69 g,10 mmol) is substituted for B-1 to give 6.34g (yield: 82%) of the product C-29, MS (M/z) (M+): 773.
Example 17
The present example provides an aromatic amine compound C-31, which is synthesized as follows:
the procedure is as in example 1 except that B-31 (5.40 g,10 mmol) is substituted for B-1 to give the final product C-31:6.75g (yield: 80%), MS (M/z) (M+): 844.
Example 18
The present example provides an aromatic amine compound C-52, which is synthesized as follows:
the procedure is as in example 1 except that B-52 (5.26 g,10 mmol) is substituted for B-1 to give 6.14g (yield: 74%) of the product C-52, MS (M/z) (M+):830.
Example 19
The present example provides an aromatic amine compound C-53, which is synthesized as follows:
the procedure is as in example 1 except that B-53 (5.33 g,10 mmol) is substituted for B-1 to give 6.53g (yield: 78%) of the product C-53, MS (M/z) (M+): 837.
Example 20
The present example provides an aromatic amine compound C-73, which is synthesized as follows:
the procedure is as in example 1 except that B-73 (4.95 g,10 mmol) is substituted for B-1 to give final product C-73:6.07g (yield: 76%), MS (M/z) (M+): 799.
Example 21
The present example provides an aromatic amine compound C-84, which is synthesized as follows:
the procedure is as in example 1 except that B-84 (5.76 g,10 mmol) is substituted for B-1 to give final product C-84:7.13g (yield: 81%), MS (M/z) (M+):880.
Example 22
The present example provides an aromatic amine compound C-111, which is synthesized as follows:
the procedure is as in example 1 except that B-111 (3.61 g,10 mmol) is substituted for B-1 to give final product C-111:5.59g (yield: 84%), MS (M/z) (M+): 666.
Example 23
The present example provides an aromatic amine compound C-115, which is synthesized as follows:
the procedure is as in example 1 except that B-115 (3.75 g,10 mmol) is substituted for B-1 to give final product C-115:5.44g (yield: 80%), MS (M/z) (M+): 680.
Example 24
The present example provides an aromatic amine compound C-121, which is synthesized as follows:
the procedure is as in example 1 except that B-121 (3.71 g,10 mmol) is substituted for B-1 to give final product C-121:5.67g (yield: 84%), MS (M/z) (M+): 675.
Example 25
The present example provides an aromatic amine compound C-131, which is synthesized as follows:
the procedure is as in example 1 except that B-131 (4.93 g,10 mmol) is substituted for B-1 to give final product C-131:5.66g (yield: 71%), MS (M/z) (M+): 797.
Example 26
The present example provides an aromatic amine compound C-133, which was synthesized as follows:
the procedure is as in example 1 except that B-133 (4.84 g,10 mmol) is substituted for B-1 to give 6.70g (yield: 85%) of the product C-133, MS (M/z) (M+): 788.
Example 27
The present example provides an aromatic amine compound C-164, which is synthesized as follows:
the procedure is as in example 1 except that B-164 (4.63 g,10 mmol) is substituted for B-1 to give final product C-164:6.29g (yield: 82%), MS (M/z) (M+): 767.
Example 28
The present example provides an aromatic amine compound C-172, which is synthesized as follows:
the procedure is as in example 1 except that B-172 (3.71 g,10 mmol) is substituted for B-1 to give final product C-172:4.73g (yield: 70%), MS (M/z) (M+): 675.
Example 29
The present example provides an aromatic amine compound C-180, which is synthesized as follows:
the procedure is as in example 1 except that B-180 (5.24 g,10 mmol) is substituted for B-1 to give final product C-180:6.21g (yield: 75%), MS (M/z) (M+): 828.
Example 30
The present example provides an aromatic amine compound C-181, which is synthesized as follows:
the procedure is as in example 1 except that B-181 (5.24 g,10 mmol) is substituted for B-1 to give final product C-181:6.46g (yield: 78%), MS (M/z) (M+): 828.
Example 31
The present example provides an aromatic amine compound C-186, which is synthesized as follows:
the procedure is as in example 1 except that B-186 (3.76 g,10 mmol) is substituted for B-1 to give final product C-186:5.58g (yield: 82%), MS (M/z) (M+): 680.
Example 32
The present example provides an aromatic amine compound C-216, which is synthesized as follows:
the procedure is as in example 1 except that B-216 (4.72 g,10 mmol) is substituted for B-1 to give 5.51g (yield: 71%) of the product C-216, MS (M/z) (M+): 776.
Example 33
The present example provides an aromatic amine compound C-219, which is synthesized as follows:
the procedure is as in example 1 except that B-219 (3.96 g,10 mmol) is substituted for B-1 to give final product C-219:5.11g (yield: 73%), MS (M/z) (M+): 700.
Example 34
The present example provides an aromatic amine compound C-221, which is synthesized as follows:
the procedure is as in example 1 except that B-221 (4.72 g,10 mmol) is substituted for B-1 to give the final product C-221:6.44g (yield: 83%), MS (M/z) (M+): 776.
Example 35
The present example provides an aromatic amine compound C-227, which is synthesized as follows:
the procedure is as in example 1 except that B-227 (4.12 g,10 mmol) is substituted for B-1 to give final product C-227:5.66g (yield: 79%), MS (M/z) (M+): 716.
Example 36
The present example provides an aromatic amine compound C-228, which is synthesized as follows:
the procedure is as in example 1 except that B-228 (5.00 g,10 mmol) is substituted for B-1 to give the final product C-228:6.76g (yield: 84%), MS (M/z) (M+): 805.
Example 37
The present example provides an aromatic amine compound C-237, which is synthesized as follows:
the procedure is as in example 1 except that B-237 (4.11 g,10 mmol) is substituted for B-1 to give 5.65g (yield: 79%) of product C-237, MS (M/z) (M+): 715.
Example 38
The present example provides an aromatic amine compound C-255, which is synthesized as follows:
the procedure is as in example 1 except that B-255 (4.96 g,10 mmol) is substituted for B-1 to give the final product C-255:6.56g (yield: 82%), MS (M/z) (M+): 800.
Example 39
The present example provides an aromatic amine compound C-278, the synthetic route of which is as follows:
the procedure is as in example 1 except that B-278 (3.71 g,10 mmol) is substituted for B-1 to give final product C-278:5.21g (yield: 77%), MS (M/z) (M+): 676.
Example 40
The present example provides an aromatic amine compound C-283, which is synthesized as follows:
the procedure is as in example 1 except that B-283 (3.81 g,10 mmol) is substituted for B-1 to give the final product C-283:4.86g (yield: 71%), MS (M/z) (M+): 685.
Example 41
The present example provides an aromatic amine compound C-299, which is synthesized as follows:
the procedure is as in example 1 except that B-299 (5.13 g,10 mmol) is substituted for B-1 to give 6.70g (yield: 82%) of the product C-299, MS (M/z) (M+): 817.
Comparative example 1
The comparative example provides a compound D1 which is tested in the research process, and the specific structural formula is as follows:
comparative example 2
The comparative example provides a compound D2 which is tested in the research process, and the specific structural formula is as follows:
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comparative example 3
The comparative example provides a compound D3 which is tested in the research process, and the specific structural formula is as follows:
effect example 1
Energy level evaluation
In order to illustrate the molecular configuration, electron cloud distribution and energy level characteristics of the aromatic amine compound provided by the invention, the molecular structures of the Gaussian 09W software based on a Density Functional Theory (DFT) calculation method (the group level is set to be 6-311+G (2D, p), the charge number is 0), C-1, C-2, C-3, C-4, C-11, C-20, C-29, C-52, C-53, C-73, C-111, C-121, C-131, C-172, C-180, C-186, C-227, C-228, C-237, C-299, D1, D2 and D3 are selected to perform geometric Optimization (Optimization), and finally the molecular geometric configuration and the front molecular track distribution and the related energy level theoretical parameters are shown in the following table 1:
TABLE 1
Numbering device GAP T1 LUMO Molecular weight Mother nucleus fragment molecular weight ratio
C-1 3.87 2.72 -0.97 742 41.11％
C-2 3.80 2.66 -0.90 762 40.03％
C-3 3.72 2.65 -0.91 762 40.03％
C-4 3.90 2.69 -0.84 728 41.90％
C-11 3.79 2.64 -0.91 755 40.40％
C-20 3.86 2.68 0.88 800 38.13％
C-29 3.83 2.89 -0.81 773 39.46％
C-52 3.98 2.75 -0.86 830 36.75％
C-53 3.97 2.75 -0.87 837 36.44％
C-73 4.07 2.97 -0.81 799 38.17％
C-111 3.91 2.67 -0.90 666 45.80％
C-121 3.90 2.68 -0.90 675 45.19％
C-131 3.88 2.66 -0.94 797 38.27％
C-172 3.93 2.71 -0.91 675 45.19％
C-180 3.93 2.73 -0.97 828 36.84％
C-186 4.05 2.91 -0.97 680 44.85％
C-227 3.86 2.75 -1.06 716 42.60％
C-228 3.82 2.75 -1.13 805 37.89％
C-237 3.87 2.78 -1.08 715 42.66％
C-299 3.83 2.76 -1.09 817 37.33％
D1 3.64 2.60 -1.06 / /
D2 3.61 2.61 -1.11 / /
D3 3.71 2.53 -1.15 / /
As can be seen from the data of table 1, the aromatic amine compound provided by the present invention has a relatively large energy gap value, a relatively high LUMO value, and a relatively large T1 as compared with the comparative example compound, and is used as a hole transport layer material or a light emitting auxiliary layer material, the energy level of which is more matched with the energy level of the adjacent organic layer, and can block electrons or excitons from leaving the light emitting layer; in addition, as can be seen from the data of table 1, the molecular weight of the aromatic amine compound provided by the present invention is mainly between 700 and 850, and the molecular weight of the compound having more condensed ring structures can reach more than 850, because the aromatic amine compound provided by the present invention has a relatively large molecular weight, the molecular weight of the tetrabiphenyl in the parent nucleus is more than 35% of the molecular weight of the whole aromatic amine compound, the aromatic amine compound has a relatively high glass transition temperature and thermal stability, and other unnecessary large molecular weight fragments are not introduced in order to raise Tg in the later stage, so that the aromatic amine compound provided by the present invention can meet the requirements of the organic electroluminescent device on the hole transport layer or the light-emitting auxiliary layer.
Device embodiment
The organic electroluminescent device of the following embodiment includes an anode 2, a hole transport region, a light emitting layer 5, an electron transport region, and a cathode 8 sequentially disposed on a substrate 1; wherein the hole transport region comprises a hole transport layer 3 and a light emitting auxiliary layer 4; the electron transport region includes an electron transport layer 6 and an electron injection layer 7; the light-emitting layer 5 is composed of a host and a doped guest, and the host of the light-emitting layer may be composed of one molecular material or multiple molecular materials. A typical structure of the organic electroluminescent device is shown in fig. 1.
The anode of the following examples employs anode materials commonly used in the art, such as ITO, ag, or a multilayer structure thereof. The hole injection unit adopts a hole injection material commonly used in the field, and F4TCNQ, HATCN, NDP-9 and the like are added for doping. The hole transport unit uses a hole transport material commonly used in the art. The light-emitting unit is made of a light-emitting material commonly used in the art, for example, the light-emitting unit can be formed by doping a host material and an emitted guest material, and the emitted guest material can be an organic material such as pyrene compound or a metal complex (such as metal Ir, pt and the like). The electron transport unit uses electron transport materials commonly used in the art. The electron injection layer uses electron injection materials commonly used in the art, such as Liq, liF, yb. 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 the following embodiments are conventional methods in the art, such as vacuum thermal evaporation, ink-jet printing, etc., and are not described herein, but only some process details and test methods in the preparation process are described in the following supplementary manner:
red light device example 1
The embodiment provides a red light organic electroluminescent device, which is prepared by the following steps: firstly, forming a hole injection layer by vacuum deposition of an HTL and F4TCNQ (the mass ratio of the HTL to the F4TCNQ is 97:3) on an ITO layer (anode) formed on a substrate at a thickness of 10 nm; secondly, forming a hole transport layer by vacuum deposition of an HTL with a thickness of 120nm on the hole injection layer, and secondly, forming a light emitting auxiliary layer by vacuum deposition of C-1 with a thickness of 80nm on the hole transport layer; forming a luminescent layer by vacuum deposition of a mixture of RH and RD on the luminescent auxiliary layer at a thickness of 40nm, wherein RH is taken as a main body, RD is taken as a doping agent, and the mass ratio of the main body to the doping agent is 97:3; then forming an electron transport layer by vacuum depositing a mixture of ET-01 and Liq on the light-emitting layer at a thickness of 35nm, wherein the mass ratio of ET-01 to Liq is 1:1, a step of; then, liF is deposited on the electron transport layer to form an electron injection layer with a thickness of 0.2nm, and finally, aluminum (Al) is deposited on the electron injection layer to form a cathode with a thickness of 150nm, so that the red light organic electroluminescent device is prepared. The molecular structural formula of the materials of the other layers except the light-emitting auxiliary layer is as follows:
red light device examples 2-10
The embodiment provides a red light organic electroluminescent device, which is prepared by the following steps: the red light organic electroluminescent device was prepared by replacing compound C-1 in example 1 with compounds C-4, C-9, C-11, C-14, C-20, C-52, C-53, C-73 and C-84, respectively, to form a light-emitting auxiliary layer, and the other preparation steps were the same as those of example 1.
Red light device comparative example 1
The comparative example provides a red light organic electroluminescent device which is tested in the research process, and the preparation method comprises the following steps: the red organic electroluminescent device was prepared by replacing compound C1 in example 1 of the red device with comparative compound D1 to form a light-emitting auxiliary layer, and the other preparation steps were the same as those of example 1 of the red device.
Green light device example 1
The embodiment provides a green light organic electroluminescent device, which is prepared by the following steps: firstly, forming a hole injection layer by vacuum deposition of an HTL and F4TCNQ (the mass ratio of the HTL to the F4TCNQ is 97:3) on an ITO layer (anode) formed on a substrate at a thickness of 10 nm; secondly, forming a hole transport layer by vacuum deposition of an HTL with a thickness of 120nm on the hole injection layer, and secondly, forming a light emitting auxiliary layer by vacuum deposition of C-111 with a thickness of 30nm on the hole transport layer; forming a luminescent layer by vacuum depositing a mixture of GPH, GNH and GD on the luminescent auxiliary layer with the thickness of 35nm, wherein the GPH and the GNH are uniformly mixed in a mass ratio of 4:6 and then serve as a main body, the GD serves as a doping agent, and the mass ratio of the main body to the doping agent is 95:5; then forming an electron transport layer by vacuum depositing a mixture of ET-01 and Liq on the light-emitting layer at a thickness of 35nm, wherein the mass ratio of ET-01 to Liq is 1:1, a step of; then, liF was deposited on the electron transport layer to form an electron injection layer at a thickness of 0.2nm, and finally, aluminum (Al) was deposited on the electron injection layer to form a cathode at a thickness of 150nm, thereby preparing a green organic electroluminescent device. The molecular structural formula of the materials of the other layers except the light-emitting auxiliary layer is as follows:
green light device examples 2 to 10
The embodiment provides a green light organic electroluminescent device, which is prepared by the following steps: the green light organic electroluminescent device was prepared by replacing the compound C-111 in the green light device example 1 with the compounds C-115, C-121, C-131, C-133, C-164, C-172, C-180, C-181 and C-186, respectively, to form a light-emitting auxiliary layer, and the other preparation steps were the same as those of the green light device example 1.
Green light device comparative example 1
The comparative example provides a green light organic electroluminescent device which is tested in the research process, and the preparation method comprises the following steps: the green organic electroluminescent device was prepared by substituting compound C-111 in example 1 for comparative compound D2 to form a light-emitting auxiliary layer, and the other preparation steps were the same as those in example 1.
Blue light device example 1
The embodiment provides a blue light organic electroluminescent device, which is prepared by the following steps: firstly, forming a hole injection layer by vacuum deposition of an HTL and F4TCNQ (the mass ratio of the HTL to the F4TCNQ is 97:3) on an ITO layer (anode) formed on a substrate at a thickness of 10 nm; secondly, forming a hole transport layer by vacuum deposition of an HTL with a thickness of 120nm on the hole injection layer, and secondly, forming a light emitting auxiliary layer by vacuum deposition of C-216 with a thickness of 10nm on the hole transport layer; forming a light-emitting layer by vacuum deposition of a mixture of BH and BD on the light-emitting auxiliary layer at a thickness of 20nm, wherein BH is used as a main body, BD is used as a doping agent, and the mass ratio of the main body to the doping agent is 98:2; then forming an electron transport layer by vacuum depositing a mixture of ET-01 and Liq on the light-emitting layer at a thickness of 35 nm; then, liF is deposited on the electron transport layer to form an electron injection layer with a thickness of 0.2nm, and finally, aluminum (Al) is deposited on the electron injection layer to form a cathode with a thickness of 150nm, so that the blue-light organic electroluminescent device is prepared. The molecular structural formula of the materials of the other layers except the light-emitting auxiliary layer is as follows:
blue light device examples 2-10
The embodiment provides a blue light organic electroluminescent device, which is prepared by the following steps: the blue organic electroluminescent device was prepared by replacing compound C-216 in blue device example 1 with compounds C-219, C-221, C-227, C-228, C-237, C-255, C-278, C-283 and C-299, respectively, to form a light-emitting auxiliary layer, and performing the other preparation steps in the same manner as in blue device example 1.
Blue light device examples 11-20
The embodiment provides a blue light organic electroluminescent device, which is prepared by the following steps: the blue light organic electroluminescent device was prepared by replacing compound C-216 in example 1 with P-1 to form a light-emitting auxiliary layer, and replacing the hole transport layer materials in example 1 with compounds C-2, C-3, C-16, C-17, C-21, C-22, C-23, C-26, C-29 and C-31, respectively, in the same manner as in example 1.
Blue light device comparative example 1
The comparative example provides a blue light organic electroluminescent device which is tested in the research process, and the preparation method comprises the following steps: the blue organic electroluminescent device was prepared by replacing compound C-216 in example 1 with comparative compound D3 to form a light-emitting auxiliary layer, and the other preparation methods were the same as those of example 1.
Blue light device comparative example 2
The comparative example provides a blue light organic electroluminescent device which is tested in the research process, and the preparation method comprises the following steps: the compound C-216 in the blue light device example 1 was replaced with P-1 to form a light-emitting auxiliary layer, and the other preparation steps were the same as those of the blue light device example 1, to prepare a blue light organic electroluminescent device.
Effect example
The organic electroluminescent devices provided in red light device examples 1 to 10, red light device comparative example 1, green light device examples 1 to 10, green light device comparative example 1, blue light device examples 1 to 20, and blue light device comparative example 1 to 2 were subjected to standard method test at j=10ma/cm 2 The driving voltage, luminance, electroluminescence current efficiency (measured in cd/a) and external quantum efficiency (EQE, measured in percent) of the organic electroluminescent device were determined as a function of the luminous density, which was calculated from the current/voltage/luminous density characteristic line (IVL characteristic line) exhibiting lambertian emission characteristics, and the luminescence spectrum. The lifetime LT is defined as the time after which the luminance is changed from the initial light-emitting luminance L when operated at a 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-emitting brightness is reduced to its initial value L after the time LT 0 Similarly, j=20 mA/cm 2 ，L 1 By 80% is meant that at 20mA/cm 2 In the down operation, the light-emitting brightness is reduced to its initial value L after the time LT 0 80% of (C).
The organic electroluminescent devices provided in red light device examples 1 to 10, red light device comparative example 1, green light device examples 1 to 10, green light device comparative example 1, blue light device examples 1 to 20 and blue light device comparative example 1 to 2 were subjected to performance test, and specific test instruments and methods are as follows: brightness was tested using a spectrum scanner photosearch PR-635; current density and lighting voltage: testing using a digital source table Keithley 2400; life test: using an LT-96ch life test device; the specific test results are shown in tables 2-5:
TABLE 2 Red light device Performance test results
TABLE 3 green device Performance test results
Table 4 blue device performance test results
TABLE 5 blue device Performance test results
As can be seen from the device performance test results in tables 2 to 5, compared with the comparative compounds, the driving voltage of the organic electroluminescent device prepared by using the aromatic amine compound provided by the present invention as a hole transport layer material or a light-emitting auxiliary layer is significantly reduced, the light-emitting efficiency is significantly improved, the lifetime is significantly prolonged, and the reason is presumed to be: the aromatic amine compound provided by the invention contains a tetrabiphenyl structure in a special connection mode, wherein the 3 # position and the 5 # position of benzene connected with nitrogen in the tetrabiphenyl are respectively replaced by monophenyl and bipartite benzene, the special connection mode enables the aromatic amine compound provided by the invention to have relatively higher LUMO and energy gap values, the aromatic amine compound provided by the invention is used as a hole transport layer material or a light-emitting auxiliary layer material, the hole transport layer material or the light-emitting auxiliary layer material is more matched with the energy level of an adjacent organic layer, and electrons or excitons can be blocked from leaving the light-emitting layer, so that the driving voltage of an organic electroluminescent device can be effectively reduced, and the efficiency of the device can be improved; the special connection mode enables the aromatic amine compound provided by the invention to have conjugation with proper degree, so that the aromatic amine compound has relatively high T1 value, and the aromatic amine compound provided by the invention is used as a hole transmission layer material or a light-emitting auxiliary layer material, and the energy transferred by a carrier of the hole transmission layer or the light-emitting auxiliary layer can meet the light-emitting energy required by the transition of a light-emitting layer, so that the light-emitting efficiency of the organic electroluminescent device can be remarkably improved; the molecular weight of the aromatic amine compound provided by the invention is more than 650, so that the excessively low glass transition temperature can be avoided, the decomposition of materials is inhibited, and the service life of a device can be effectively prolonged. Therefore, the aromatic amine compound provided by the invention is a hole transport layer material or a light-emitting auxiliary layer material with good performance, can meet the performance requirement of an organic electroluminescent device, and has practical value.
It should be understood that the foregoing examples of the present invention are provided merely for clearly illustrating the present invention and are not intended to limit the embodiments of the present invention, and that various other changes and modifications may be made therein by one skilled in the art without departing from the spirit and scope of the present invention as defined by the appended claims.

Claims (9)

1. An aromatic amine compound comprising a tetrabenamine structure, wherein the aromatic amine compound has the structural formula shown in formula i:
wherein the Ar is 1 、Ar 2 Each independently selected from substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 5 ～C 60 Heteroaryl, substituted or unsubstituted C 10 ～C 60 Substituted or unsubstituted C 9 ～C 60 Substituted or unsubstituted C 3 ～C 30 Any one of cycloalkyl groups of (a);
when saidAr 1 Or Ar 2 When a substituent is present, the substituent is selected from deuterium, halogen, hydroxy, cyano, nitro, amino, carboxy or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, C 1 ～C 10 Alkyl, C of (2) 6 ～C 60 Aryl, C of (2) 5 ～C 60 Heteroaryl, C 10 ～C 60 Condensed ring aryl, C 9 ～C 60 Hetero-condensed ring aryl or C 3 ～C 30 Wherein two or more substituents may be the same or different and may be linked to each other to form an aliphatic ring, an aromatic ring, a heteroaromatic ring, a condensed ring or a heterocondensed ring;
the L is 2 Selected from single bonds, substituted or unsubstituted C 1 ～C 12 Alkylene, substituted or unsubstituted C 6 ～C 30 Arylene, substituted or unsubstituted C 6 ～C 30 Any one of heteroarylene groups of (a);
any one of the hydrogens on the compound of formula I may be each independently substituted with deuterium, alkyl, or cycloalkyl.
2. The aromatic amine compound according to claim 1, wherein Ar 1 The structural formula of (2) is shown as formula II:
wherein the R is 1 、R 2 Each independently selected from hydrogen, deuterium, substituted or unsubstituted C 1 ～C 10 Alkyl, substituted or unsubstituted C 3 ～C 10 Cycloalkyl, substituted or unsubstituted C 6 ～C 30 Aryl, substituted or unsubstituted C 5 ～C 30 Heteroaryl, substituted or unsubstituted C 1 ～C 6 Alkoxy, substituted or unsubstituted C 10 ～C 60 Substituted or unsubstituted C 9 ～C 30 Aralkyl, substituted or unsubstituted C 6 ～C 30 Aryloxy, substituted or unsubstituted C 6 ～C 30 Any one of the above-mentioned two or more groups may be linked to each other to form an aliphatic ring, an aromatic ring, a heteroaromatic ring, a condensed ring or a hetero condensed ring;
the a is selected from integers from 1 to 5; the b is selected from integers from 1 to 4;
the L is 1 Selected from single bonds, O, S, substituted or unsubstituted C 1 ～C 12 Alkylene, substituted or unsubstituted C 6 ～C 30 Any one of arylene groups of (a);
any one of the hydrogens on the compound of formula II may be independently substituted with deuterium, alkyl or cycloalkyl.
3. The aromatic amine compound according to claim 2, wherein the compound represented by the formula ii is one of the structures represented by the following formulas ii-1 to ii-7:
wherein n is selected from integers from 1 to 4; the m is selected from integers from 1 to 3;
the L is 1 Selected from single bonds, O, S, substituted or unsubstituted C 1 ～C 12 Alkylene, substituted or unsubstituted C 6 ～C 30 Any one of arylene groups of (a);
the L is 2 Any one selected from single bond and O, S;
the X is selected from O, S, CR 3 R 4 、NR 5 Any one of them;
the R is 3 、R 4 Each independently selected from hydrogen, deuterium, substituted or unsubstituted C 1 ～C 10 Alkyl, substituted or unsubstituted C 6 ～C 30 Aryl, substituted or unsubstituted C 5 ～C 30 Heteroaryl, substituted or unsubstituted C 10 ～C 60 Substituted or unsubstituted C 6 ～C 30 Aralkyl, substituted or unsubstituted C 6 ～C 30 Aryloxy, substituted or unsubstituted C 6 ～C 30 Arylthio, R 3 、R 4 May be linked to each other to form an aliphatic ring, an aromatic ring, a heteroaromatic ring, a condensed ring, or a heterocondensed ring;
the R is 5 Selected from hydrogen, deuterium, substituted or unsubstituted C 1 ～C 10 Alkyl, substituted or unsubstituted C 6 ～C 30 Aryl of (a);
any one of the hydrogens on the compounds of formulas II-1 to II-7 may be each independently substituted with deuterium, alkyl or cycloalkyl.
4. The aromatic amine compound according to claim 1, wherein Ar 2 Selected from substituted or unsubstituted C 6 ～C 30 Aryl, substituted or unsubstituted C 5 ～C 30 Heteroaryl, substituted or unsubstituted C 10 ～C 30 Substituted or unsubstituted C 9 ～C 30 Substituted or unsubstituted C 3 ～C 15 Any one of cycloalkyl groups of (a).
5. The aromatic amine compound according to claim 1, wherein Ar 2 Selected from any one of the groups indicated by a-1 to a-92:
6. the aromatic amine compound according to claim 1, wherein L 2 Selected from single bond,Any one of the following.
7. The aromatic amine compound according to claim 1, wherein the compound represented by formula i is selected from any one of the following compounds:
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8. use of the aromatic amine compound according to any one of claims 1 to 7 in the field of organic electroluminescence.
9. An organic electroluminescent device is characterized by comprising an anode, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport region and a cathode which are sequentially arranged on a substrate; wherein the light-emitting auxiliary layer and/or the hole transport layer comprises one or more aromatic amine compounds according to any one of claims 1 to 7.
CN202211200073.6A 2022-09-29 2022-09-29 Aromatic amine compound containing tetrabenamine structure and organic electroluminescent device containing aromatic amine compound Pending CN117843501A (en)

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EP3312166B1 (en) * 2016-10-21 2019-11-27 Samsung Display Co., Ltd. Monoamine compound and organic electroluminescence device including the same
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
KR20200122116A (en) * 2019-04-17 2020-10-27 엘지디스플레이 주식회사 Novel compound and organic light emitting device
CN110156611B (en) * 2019-05-23 2022-11-11 武汉尚赛光电科技有限公司 Phenyl branched luminescent material and organic electroluminescent device thereof
CN112778253B (en) * 2019-11-07 2024-02-09 北京鼎材科技有限公司 Organic compound and organic electroluminescent device containing the same
CN111440156A (en) * 2020-05-07 2020-07-24 吉林奥来德光电材料股份有限公司 Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device
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KR20220007307A (en) * 2020-07-10 2022-01-18 주식회사 동진쎄미켐 Novel compounds and organic electroluminescent device comprising the same
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