CN113816960A - Organic compound and organic electroluminescent device comprising the same - Google Patents

Organic compound and organic electroluminescent device comprising the same Download PDF

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CN113816960A
CN113816960A CN202111139804.6A CN202111139804A CN113816960A CN 113816960 A CN113816960 A CN 113816960A CN 202111139804 A CN202111139804 A CN 202111139804A CN 113816960 A CN113816960 A CN 113816960A
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compound
organic
layer
electroluminescent device
organic electroluminescent
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高春吉
叶绪兵
胡聪丛
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Zhejiang Huadisplay Optoelectronics Co Ltd
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Zhejiang Huadisplay Optoelectronics Co Ltd
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Abstract

The present invention provides an organic compound represented by the following formula 1:

Description

Organic compound and organic electroluminescent device comprising the same
Technical Field
The present invention relates to an organic compound, and more particularly, to an organic compound and an organic electroluminescent device including the same.
Background
With the development of multimedia technology and the increase of information-oriented requirements, the requirements for the performance of panel displays are increasing. The OLED has a series of advantages of autonomous light emission, low-voltage direct current driving, full curing, wide viewing angle, rich colors and the like, is widely noticed due to potential application in new-generation displays and lighting technologies, and has a very wide application prospect. The organic electroluminescent device is a spontaneous light emitting device, and the OLED light emitting mechanism is that under the action of an external electric field, electrons and holes are respectively injected from a positive electrode and a negative electrode and then migrate, recombine and attenuate in an organic material to generate light. A typical structure of an OLED comprises one or more functional layers of a cathode layer, an anode layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport layer, a hole injection layer and an organic light emitting layer.
Although the research on organic electroluminescence is rapidly progressing, there are still many problems to be solved, such as the improvement of External Quantum Efficiency (EQE), the design and synthesis of new materials with higher color purity, the design and synthesis of new materials with high efficiency electron transport/hole blocking, and the like. For the organic electroluminescent device, the luminous quantum efficiency of the device is the comprehensive reflection of various factors and is an important index for measuring the quality of the device.
Luminescence can be divided into fluorescence and phosphorescence. In fluorescence emission, an organic molecule in a singlet excited state transits to a ground state, thereby emitting light. On the other hand, in phosphorescence, organic molecules in a triplet excited state transition to a ground state, thereby emitting light.
At present, some organic electroluminescent materials have been applied in the market due to their excellent performance, but as host materials in organic electroluminescent devices, in addition to the triplet energy level being higher than the guest materials, it is more important to have good hole transport performance to prevent the energy reverse transfer of exciton transition release. Currently, materials having both a high triplet level and good hole mobility in the host material are still lacking. Therefore, how to design a new host material with better performance is a problem to be solved by those skilled in the art.
Disclosure of Invention
An object of the present invention is to provide an organic compound having a reduced driving voltage, excellent luminous efficiency and a lifetime, and an organic electroluminescent device including the same.
In order to realize the purpose of the invention, the technical scheme of the invention is as follows:
the invention provides an organic compound, the structure of which is shown as formula 1:
Figure BDA0003283367930000021
wherein R is1Is substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-30 aryl or substituted or unsubstituted C3-C30 heteroaryl.
Ar1 is selected from the group consisting of:
Figure BDA0003283367930000022
Figure BDA0003283367930000031
wherein R is2、R3And R4Each independently selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl.
Preferably wherein the organic compound is selected from the group consisting of:
Figure BDA0003283367930000041
Figure BDA0003283367930000051
Figure BDA0003283367930000061
Figure BDA0003283367930000071
Figure BDA0003283367930000081
Figure BDA0003283367930000091
Figure BDA0003283367930000101
Figure BDA0003283367930000111
Figure BDA0003283367930000121
Figure BDA0003283367930000131
Figure BDA0003283367930000141
Figure BDA0003283367930000151
Figure BDA0003283367930000161
Figure BDA0003283367930000171
Figure BDA0003283367930000181
the present invention also provides an organic electroluminescent device comprising an anode, an organic layer and a cathode deposited in this order, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer or an electron injection layer, wherein the organic layer comprises the organic compound of the present invention.
Preferably wherein the organic layer further comprises a doping compound.
More preferably wherein the weight ratio of the organic compound to the doping compound is 1: 99-99: 1.
the electron-rich heterocyclic ring linked structure in the organic compound structure has great influence on the photoelectric property of the whole compound molecule, thereby being beneficial to reducing unnecessary vibration energy loss and realizing high-efficiency luminous performance. By adjusting substituent groups, the complex has better thermal stability and chemical properties. The preparation method of the organic compound is simple, the raw materials are easy to obtain, and the industrial requirements can be met.
The organic compound is prepared into an organic electroluminescent device, and particularly used as a main material, the device has the advantages of low driving voltage and high luminous efficiency, and is superior to the conventional common OLED device.
Detailed Description
The invention also provides application of the organic compound in an organic electroluminescent device.
Preferably, the organic electroluminescent device comprises an anode, a cathode and a plurality of organic energy layers positioned between the anode and the cathode, wherein the organic functional layer contains the organic compound.
The organic electroluminescent device of the present invention preferably comprises an anode, a cathode and a plurality of organic functional layers located between the anode and the cathode. The term "organic functional layer" refers to all layers disposed between an anode and a cathode in an organic electroluminescent device, and the organic functional layer may be a layer having a hole property and a layer having an electron property, for example, the organic functional layer includes one or more of a hole injection layer, a hole transport layer, a hole injection and transport functional layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron transport and injection functional layer.
The hole injection layer, the hole transport layer, and the functional layer having both hole injection and hole transport properties of the present invention may include an electron-generating substance in addition to a conventional hole injection substance, a conventional hole transport substance, and a substance having both hole injection and hole transport properties. For example, the organic functional layer is an emissive layer, and the emissive layer includes one or more of phosphorescent hosts, fluorescent hosts, phosphorescent dopants, and fluorescent dopants. The compound for the organic electroluminescent device can be used as a fluorescent main body, can also be used as fluorescent doping, and can be used as the fluorescent main body and the fluorescent doping at the same time.
The light-emitting layer of the present invention may be a red, yellow or blue light-emitting layer. And when the luminescent layer is a red luminescent layer, the compound for the organic electroluminescent device is used as a red main body, so that the organic electroluminescent device with high efficiency, high resolution, high brightness and long service life can be obtained.
The organic electroluminescent device comprises an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode which are sequentially deposited, wherein the red phosphorescent compound is used as a host material of the light-emitting layer.
The method for preparing the organic electroluminescent device of the present invention is not particularly limited, and other methods and materials for preparing the organic electroluminescent device known to those skilled in the art may be used in addition to the host compound represented by formula 1.
Examples
Example 1: synthesis of Compound 1-1
1. Synthesis of intermediate Sub-1
Figure BDA0003283367930000201
A500 mL reaction flask was charged with intermediate phenylboronic acid (7.49g,61.4mmol), 2, 4-dibromothiazole (17.68g,61.4mmol), tetrakis (triphenylphosphine) palladium (5 mol%), K2CO3(17.0g,122.8mmol), 1, 4-dioxane (200mL) and water (50 mL). The reaction system is heated to 80 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated and recrystallized to give a crude product, which was then passed through a silica gel column to obtain intermediate Sub-1(13.13g, yield 75%). LC-MS: M/Z283.99 (M +).
2. Synthesis of intermediate Sub-4
Figure BDA0003283367930000202
A250 mL three-necked flask was charged with intermediate Sub-3(3.46g, 10mmol), bromobenzene (1.65g,10.5mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.8g,33.6mmol) and o-xylene (80 mL). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product, which was then passed through a silica gel column to obtain Compound Sub-4(1.27g, yield 30%). LC-MS: M/Z422.18 (M +).
3. Synthesis of Compound 1-1
Figure BDA0003283367930000203
A250 mL three-necked flask was charged with intermediate Sub-4(4.23g, 10mmol), intermediate Sub-1(2.99g,10.5mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.8g,33.6mmol) and o-xylene (80 mL). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product, which was then subjected to silica gel column to obtain Compound 1-1(4.51g, yield 72%). LC-MS: M/Z626.25 (M +).
Example 2: synthesis of Compounds 1-5
1. Synthesis of intermediate Sub-5
Figure BDA0003283367930000211
A250 mL three-necked flask was charged with intermediate 2, 4-dibromobenzo [4,5] thieno [3,2-d ] pyrimidine (3.85g, 11.2mmol), intermediate carbazole (3.0g,12.3mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.8g,33.6mmol) and o-xylene (80 mL). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give crude product, which was then passed through a silica gel column to give Sub-5(3.86g, yield 80%). LC-MS: M/Z430.32 (M +).
2. Synthesis of Compounds 1-5
Figure BDA0003283367930000212
Compounds 1-5 were synthesized according to the method of example 1, and the other steps were carried out according to the synthesis of compound 1-1 to give compounds 1-5(4.65g, yield 65%). LC-MS: M/Z715.27(M +).
Example 3: synthesis of Compounds 1-10
Figure BDA0003283367930000213
Compounds 1-10 were synthesized according to the method of example 1, and the other steps refer to the synthesis of compound 1-1, to give compounds 1-10(4.45g, yield 60%). LC-MS: M/Z742.31 (M +).
Example 4: synthesis of Compounds 1-11
Figure BDA0003283367930000221
Compounds 1 to 11 were synthesized by the method of reference example 1, and the other steps referred to the synthesis of Compound 1-1, to give Compound 1 to 11(4.51g, yield 63%). LC-MS: M/Z716.26 (M +).
Example 5: synthesis of Compounds 1-50
Figure BDA0003283367930000222
Compounds 1 to 50 were synthesized by the method of reference example 1, and the other steps referred to the synthesis of compound 1 to 1, to give compounds 1 to 50(3.99g, yield 55%). LC-MS: M/Z726.28 (M +)
Example 6: synthesis of Compounds 4-17
Figure BDA0003283367930000223
Compounds 4-17 were synthesized according to the method of example 1, and the other steps were carried out according to the synthesis of compound 1-1 to obtain compounds 4-17(4.50g, yield 58%). LC-MS: M/Z775.28 (M +).
Example 7: synthesis of Compounds 4-21
Figure BDA0003283367930000224
Compounds 4 to 21 were synthesized by the method of reference example 1, and the other steps referred to the synthesis of compound 1 to 1, to give compounds 4 to 21(4.45g, yield 55%). LC-MS: M/Z808.30 (M +).
Example 8: synthesis of Compounds 4-24
Figure BDA0003283367930000231
Compounds 4 to 24 were synthesized by the method of reference example 1, and the other steps referred to the synthesis of Compound 1, to give compounds 4 to 24(4.13g, yield 57%). LC-MS: M/Z724.30 (M +).
Table 1: evaluation results of HOMO, LUMO, triplet energy level and S1-T1 energy level of organic compound of the present invention (DFT calculation by Gaussian software/based on B3LYP functional)
TABLE 1
Figure BDA0003283367930000232
Figure BDA0003283367930000241
As can be seen from Table 1, the HOMO value of the compound of the present invention is reduced as compared with that of the comparative compound, the Eg (eV) value is more suitable for the RH (phosphorescent host) condition, and the delayed fluorescence property (S1-T1) is enhanced.
Device embodiments
1. First embodiment
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. The patterned ITO glass substrate was then washed.
The substrate is then placed in a vacuum chamber. The standard pressure was set at 1X 10-6 Torr. Thereafter on an ITO substrate
Figure BDA0003283367930000242
Compound 1-1+ RD-1 (2% by weight)
Figure BDA0003283367930000243
HB-1
Figure BDA0003283367930000244
And
Figure BDA0003283367930000245
the sequence of (a) and (b) forming layers of organic material.
Figure BDA0003283367930000246
Figure BDA0003283367930000251
2. Second embodiment
An organic electroluminescent device of the second embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with compound 1-5 instead of compound 1-1 of the first embodiment.
3. Third embodiment
An organic electroluminescent device of the second embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with the compound 1-10 instead of the compound 1-1 of the first embodiment.
4. Fourth embodiment
An organic electroluminescent device of the second embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with compound 1-11 instead of compound 1-1 of the first embodiment.
5. Fourth embodiment
An organic electroluminescent device of the second embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with the compound 1-50 instead of the compound 1-1 of the first embodiment.
6. Third embodiment
An organic electroluminescent device of the third embodiment was fabricated in the same manner as in the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with compounds 4 to 17 from compound 1 to 1 of the first embodiment.
7. Fourth embodiment
An organic electroluminescent device of the fourth embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with compounds 4 to 21 instead of compound 1 to 1 of the first embodiment.
8. Fifth embodiment
An organic electroluminescent device of the fifth embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with compounds 4 to 24 from compound 1 to 1 of the first embodiment.
9. Comparative example 1
An organic electroluminescent device of a comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with the compound Ref-1 instead of the compound 1-1 of the first embodiment.
10. Comparative example 2
An organic electroluminescent device of a comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with the compound Ref-2 instead of the compound 1-1 of the first embodiment.
11. Comparative example 3
An organic electroluminescent device of a comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with the compound Ref-3 instead of the compound 1-1 of the first embodiment.
12. Comparative example 4
An organic electroluminescent device of a comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with the compound Ref-4 instead of the compound 1-1 of the first embodiment.
13. Comparative example 5
An organic electroluminescent device of a comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with the compound Ref-5 instead of the compound 1-1 of the first embodiment.
The prepared organic electroluminescent device is at 10mA/cm2Voltage, efficiency and life were tested under current conditions.
Table 2 shows the performance test results of the organic electroluminescent devices prepared in the examples and comparative examples of the present invention.
TABLE 2
Figure BDA0003283367930000261
Figure BDA0003283367930000271
As shown in table 2, the organic electroluminescent device comprising the compound according to the present invention as a host material has higher luminous efficiency and longer life characteristics than those of the comparative compound.
The foregoing has described the general principles, principal features, and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are given by way of illustration of the principles of the present invention, and that various changes and modifications may be made without departing from the spirit and scope of the invention as defined by the appended claims. The scope of the invention is defined by the appended claims and equivalents thereof.

Claims (5)

1. An organic compound having a structure represented by formula 1:
Figure FDA0003283367920000011
wherein R1 is substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-30 aryl or substituted or unsubstituted C3-C30 heteroaryl;
ar1 is selected from the group consisting of:
Figure FDA0003283367920000012
Figure FDA0003283367920000021
wherein R is2、R3And R4Each independently selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.
2. The organic compound of claim 1, wherein the organic compound is selected from the group consisting of:
Figure FDA0003283367920000031
Figure FDA0003283367920000041
Figure FDA0003283367920000051
Figure FDA0003283367920000061
Figure FDA0003283367920000071
Figure FDA0003283367920000081
Figure FDA0003283367920000091
Figure FDA0003283367920000101
Figure FDA0003283367920000111
Figure FDA0003283367920000121
Figure FDA0003283367920000131
Figure FDA0003283367920000141
Figure FDA0003283367920000151
Figure FDA0003283367920000161
Figure FDA0003283367920000171
3. an organic electroluminescent device comprising an anode, an organic layer and a cathode deposited in this order, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer or an electron injection layer, wherein the organic layer comprises the organic compound of any one of claims 1-2.
4. The organic electroluminescent device according to claim 3, wherein the organic layer further comprises a doping compound.
5. The organic electroluminescent device according to claim 4, wherein the weight ratio of the organic compound to the dopant compound is 1: 99-99: 1.
CN202111139804.6A 2021-09-28 2021-09-28 Organic compound and organic electroluminescent device comprising the same Pending CN113816960A (en)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002265938A (en) * 2001-03-14 2002-09-18 Toyo Ink Mfg Co Ltd Material for organic electroluminescence device and organic electroluminescence device using the same
KR20110120075A (en) * 2010-04-28 2011-11-03 에스에프씨 주식회사 Spiro compounds and organic light-emitting diode including the same
CN109942601A (en) * 2019-03-18 2019-06-28 深圳大学 A kind of fluorescent material, preparation method and application
CN110343105A (en) * 2018-04-05 2019-10-18 三星显示有限公司 Organnic electroluminescent device and polycyclic compound for Organnic electroluminescent device
CN110981871A (en) * 2019-12-11 2020-04-10 北京大学深圳研究生院 Blue light material and preparation method and application thereof
CN111423440A (en) * 2020-03-27 2020-07-17 浙江华显光电科技有限公司 Red phosphorescent host compound and organic light-emitting device using same

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002265938A (en) * 2001-03-14 2002-09-18 Toyo Ink Mfg Co Ltd Material for organic electroluminescence device and organic electroluminescence device using the same
KR20110120075A (en) * 2010-04-28 2011-11-03 에스에프씨 주식회사 Spiro compounds and organic light-emitting diode including the same
CN110343105A (en) * 2018-04-05 2019-10-18 三星显示有限公司 Organnic electroluminescent device and polycyclic compound for Organnic electroluminescent device
CN109942601A (en) * 2019-03-18 2019-06-28 深圳大学 A kind of fluorescent material, preparation method and application
CN110981871A (en) * 2019-12-11 2020-04-10 北京大学深圳研究生院 Blue light material and preparation method and application thereof
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