Light-emitting material and organic electroluminescent device

Abstract

The application provides a luminescent material and an organic electroluminescent device, and has a compound, wherein Ar1, Ar2, Ar3 and Ar3 are independently substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl or substituted or unsubstituted aryl. The technical scheme of the application can be used as a blue fluorescent luminescent material, and the OLED device matched with the luminescent material has good service life.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of organic electroluminescent devices, in particular to a light emitter material and an organic electroluminescent device having the same. BACKGROUND

[0002] Organic electroluminescence (EL) is the phenomenon that organic materials emit light under the excitation of electric energy, which was discovered as early as 50 years ago, but it did not get wide attention until the birth of organic light-emitting diode (OLED) in 1987. In simple terms, OLED is a device that uses multi-layer organic thin film structure to generate electrically excited light, which is easy to manufacture and only needs very low driving voltage, and has excellent display characteristics and quality compared with LCD, such as self-luminescence, wide viewing angle, high efficiency, wide color gamut, and flexible display, so OLED has become a new generation of mainstream flat panel display.

[0003] High-performance OLED functional materials are selected and reasonably matched to play the comprehensive characteristics of high efficiency, long service life and low voltage of the device. The materials constituting the organic material layer, such as hole transport material, light-emitting material, electron transport material, etc., should have the following characteristics: high efficiency of fluorescence in the visible light region, high conductivity, good semiconductor characteristics; good film-forming properties, and the formed thin film has good uniformity, etc.

[0004] Although the industrialization process of organic electroluminescent display devices has made great progress, there are still many major fundamental problems in the light-emitting materials of OLED, colorization technology, film forming technology, active driving technology, packaging technology, etc. This makes the device have a short service life and low efficiency, and due to the immaturity of the process, the cost is high.

[0005] Therefore, the present application provides a light emitter material with low voltage, high efficiency and the like, and an organic electroluminescent device having the same. SUMMARY

[0006] In view of the problems in the prior art, the purpose of the present application is to provide a light emitter material and an organic electroluminescent device having the same, which not only has a low voltage, but also has a high efficiency and a long service life.

[0007] According to one aspect of the present application, a light emitter material is provided, which is a compound having a structure shown in Formula I:

[0008]

[0009] wherein Ar1, Ar2, Ar3 and Ar4 are each independently substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, or substituted or unsubstituted aryl.

[0010] Preferably, each of Ar1, Ar2, Ar3and Ar4is independently substituted or unsubstituted C6-C10aryl. 60 Preferably, each of Ar1, Ar2, Ar3and Ar4is independently substituted or unsubstituted C6-C10aryl.

[0011] Preferably, each of Ar1, Ar2, Ar3and Ar4is independently substituted or unsubstituted C6-C10aryl.

[0012] Preferably, each of Ar1, Ar2, Ar3and Ar4is independently substituted or unsubstituted C6-C10aryl. 15 Preferably, each of Ar1, Ar2, Ar3and Ar4is independently substituted or unsubstituted C6-C10aryl.

[0013] Preferably, each of Ar1, Ar2, Ar3and Ar4is independently substituted or unsubstituted C6-C10aryl. 60 Preferably, each of Ar1, Ar2, Ar3and Ar4is independently substituted or unsubstituted C6-C10aryl.

[0014] Preferably, each of Ar1, Ar2, Ar3and Ar4is independently substituted or unsubstituted C6-C10aryl. 60 Preferably, each of Ar1, Ar2, Ar3and Ar4is independently substituted or unsubstituted C6-C10aryl.

[0015] Preferably, each of Ar1, Ar2, Ar3and Ar4is independently substituted or unsubstituted C6-C10aryl.

[0016]

[0017]

[0018] Preferably, the light-emitting material is a blue fluorescent light-emitting material.

[0019] According to another aspect of the present application, there is also provided an organic electroluminescent device doped with the light-emitting material described above.

[0020] The light-emitting material and the organic electroluminescent device having the same according to the present application can be used as a blue fluorescent light-emitting material, and the OLED device combined with the same has a good lifetime. DETAILED DESCRIPTION

[0021] Example implementations will now be described more fully with reference to the accompanying drawings. Example implementations may, however, be implemented in many different forms and should not be construed as limited to the implementations set forth herein. Rather, these implementations are provided as example implementations so as to convey the principles of the application to those skilled in the art fairly and most simply.

[0022] In embodiments of the present application, there is provided a light-emitting material and an organic electroluminescent device having the same, a compound having a structure represented by Formula I:

[0023]

[0024] wherein Ar1, Ar2, Ar3 and Ar4 are each independently substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl or substituted or unsubstituted aryl.

[0025] The luminescent material and the organic electroluminescent device having the same according to the embodiments of the present application adopt the stereorigid structure of benzazepine, thereby having good stability and better efficiency.

[0026] Preferably, Ar1, Ar2, Ar3 and Ar4 are each independently substituted or unsubstituted C6-C 60 aryl, fluorenyl, C2-C 60 heterocyclyl containing O, N or S or C3-C 60 aliphatic cyclyl.

[0027] In the embodiments of the present application, the compound of the structure shown in Formula I is preferably:

[0028]

[0029] The present application is described in detail in the following specific examples:

[0030] Compound 1

[0031] The synthetic method for preparing Compound 1 is as follows:

[0032]

[0033] The structure thereof is determined according to mass spectrum. HRMS C 54 H 34 N4 calculated value: 738.28 test value: 738.89 C 54 H 34 Elemental analysis theoretical value: C, 87.78; N, 7.58; H, 4.64 elemental analysis test value: C, 87.87; N, 7.48; H, 4.62

[0034] Compound 2

[0035]

[0036] The synthetic method of Compound 2 is consistent with that of Compound 1, except that the arylamine compound A6 is replaced by B6, to obtain 3.7 g of Compound 2 (yield 65%).

[0037] The structure thereof is determined according to mass spectrum. HRMS C 56 H38 N4Calcd: 766.31 Found: 766.92 C 56 H 38 N4Elemental analysis theory: C, 87.75; N, 7.32; H, 4.92 Elemental analysis test: C, 87.70; N, 7.28; H, 4.95

[0038] Compound 3

[0039]

[0040] The synthesis method of compound 3 is consistent with that of compound 1, except that the aromatic amine compound A6 is replaced by C6, to obtain 3.9 g of compound 3 (yield 68%).

[0041] The structure is determined according to mass spectrum. HRMS C 56 H 38 N4Calcd: 766.31 Found: 766.92 C 56 H 38 N4Elemental analysis theory: C, 87.75; N, 7.32; H, 4.92 Elemental analysis test: C, 87.70; N, 7.28; H, 4.95

[0042] Compound 4

[0043]

[0044] The synthesis method of compound 4 is consistent with that of compound 1, except that the aromatic amine compound A6 is replaced by D6, to obtain 4.1 g of compound 4 (yield 70%).

[0045] The structure is determined according to mass spectrum. HRMS C 58 H 42 N4Calcd: 794.34 Found: 795 C 58 H 42 N4Elemental analysis theory: C, 87.63; N, 7.05; H, 5.33 Elemental analysis test: C, 87.70; N, 7.08; H, 5.35

[0046] Compound 5

[0047]

[0048] The synthesis method of compound 5 is consistent with that of compound 1, except that the aromatic amine compound A6 is replaced by E6, to obtain 4.05 g of compound 5 (yield 69%).

[0049] The structure was determined by mass spectrometry. HRMS for C58H42N4calculated: 794.34 found: 795 Elemental analysis for C58H42N4theoretical: C, 87.61; N, 7.08; H, 5.35 Elemental analysis for C58H42N4found: C, 87.63; N, 7.11; H, 5.28

[0050] Compound 6

[0051]

[0052] The synthesis of compound 6 was carried out in the same manner as that of compound 1, except that the arylamine compound A6 was replaced by F6, to obtain 4.1 g of compound 6 (yield 70%).

[0053] The structure was determined by mass spectrometry. HRMS for C 60 H 46 N4calculated: 822.37 found: 823.06 C 60 H 46 Elemental analysis for C58H42N4theoretical: C, 87.61; N, 6.81; H, 5.63 Elemental analysis for C58H42N4found: C, 87.56; N, 6.85; H, 5.63

[0054] Control test

[0055] Examples 1-6

[0056] The organic light emitting elements 1-6 were prepared by using the compounds 1-6 prepared by the present application, respectively.

[0057] The organic light emitting elements 1-6 sequentially include an anode substrate, a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an emission layer (EML), an electron transport layer (ETL), and a cathode, from bottom to top.

[0058] The composition materials of each layer of the organic light emitting elements 1-6 are as follows:

[0059] Anode substrate: ITO (indium tin oxide), thickness 50 nm;

[0060] Hole injection layer: hexacyno hexaazatriphenylene (HAT), thickness 5 nm;

[0061]

[0062] Hole transport layer: HTM of the following formula, thickness 125 nm;

[0063]

[0064] Electron blocking layer: SpMA3 of the following formula, thickness 10 nm;

[0065]

[0066] Emission layer: host material BH, guest material is compound 1-6 prepared respectively, mass ratio of host and guest material is 19:1; thickness is 20 nm;

[0067]

[0068] Electron transport layer: host material ETM, guest material LiQ, mass ratio of host and guest material is 1:1; thickness is 30 nm;

[0069]

[0070] Cathode: LiF and aluminum, thickness is 100 nm.

[0071] Comparative Example 1

[0072] Organic light emitting element 7 was prepared. The difference between the organic light emitting element 7 and the organic light emitting element 1-6 prepared by using compound 1-6 is that the following formula BDV is used instead of compound 1-6 in the guest material of the emission layer in the organic light emitting element 7, and the rest is the same.

[0073]

[0074] Performance test

[0075] The organic light emitting elements 1-6 prepared by the examples 1-6 of the present application and the organic light emitting element 7 prepared by the comparative example 1 were subjected to the following performance test:

[0076] The voltage (V@10mA / cm2), efficiency (Cd / A@10mA / cm2) and service life were measured when a current density of 10mA / cm2was applied to the organic light emitting elements 1-7. 2 2 2

[0077] The performance test results are shown in Table 1:

[0078] Table 1: Test results

[0079] Classification Emission layer Voltage Efficiency T95 (hours) Organic light emitting element 1 BH: Compound 1 3.91 6.61 355 Organic light emitting element 2 BH: Compound 2 3.63 7.65 405 Organic light emitting element 3 BH: Compound 3 3.76 7.88 410 Organic light emitting element 4 BH: Compound 4 3.67 7.76 415 Organic light emitting element 5 BH: Compound 5 3.77 7.84 420 Organic light emitting element 6 BH: Compound 6 3.74 7.75 410 Organic light emitting element 7 BH: BDV 3.84 7.85 425

[0080] From the performance data in Table 1, it can be seen that the organic light emitting element prepared by the material of the examples of the present application has better performance in current efficiency, driving voltage and service life compared with the comparative example due to the good stability and stereorigid structure of the benzazepine ring.

[0081] ​​​In conclusion, the luminescent material and the organic electroluminescent device having the same have lower voltage and higher efficiency.

[0082] The above is further detailed description of the present application in combination with specific preferred embodiments, and cannot be deemed as limitation of the specific implementation of the present application to these descriptions. For those skilled in the art to which the present application belongs, without departing from the concept of the present application, a number of simple deductions or substitutions can be made, which shall be deemed as falling within the protection scope of the present application.

Claims

1. A luminescent material, characterized in that, Compounds having the structure of Formula I: Formula I wherein Ar1is a substituted or unsubstituted phenyl group, the substituents being C1to C5alkyl groups or C5to C10cycloalkyl groups, Ar2, Ar3and Ar4are each independently a phenyl group, or a C1to C5alkyl-substituted phenyl group. 15 wherein Ar1is a substituted or unsubstituted phenyl group, the substituents being C1to C5alkyl groups or C5to C10cycloalkyl groups, Ar2, Ar3and Ar4are each independently a phenyl group, or a C1to C5alkyl-substituted phenyl group.

2. The luminophoric material of claim 1, wherein: The compound of Formula I is: 、 、 , , or .

3. An organic electroluminescent device, characterized by: The organic electroluminescence device is doped with the light emitter material according to claim 1 or 2.

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