CN107586307B - Silafluorene derivative for electroluminescent material - Google Patents
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Abstract
The invention provides a silafluorene derivative for an electroluminescent material, which has a structure shown as a general formula (I):
wherein R is1～R7Each independently selected from: H. C1-C8 alkanyl, C1-C8 alkoxy, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heterocyclic aryl, or-NR8R9And R is8、R9Each independently selected from C1-C8 alkanyl, C1-C8 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C6-C30 heterocyclic aryl; x is N or P. The invention also provides a luminescent main body material, an electron transport layer material, a hole transport layer material and an OLED device containing the silafluorene derivative, which have the advantages of excellent hole transport property, solubility and thermal stability, wide energy band, high glass transition temperature, difficult crystallization and the like.
Description
Technical Field
The invention relates to a compound, in particular to a silafluorene derivative for an electroluminescent material.
Background
Organic electroluminescence is known as the most potential next generation flat panel display technology by the industry and academia, and has the advantages of low power consumption, wide viewing angle, fast response, lightness, thinness, flexible display and the like.
Organic electroluminescent diodes (OLEDs), as a brand new display technology, have the advantages of the existing display technology, such as all solid state, self-luminescence, high brightness, high resolution, wide viewing angle (over 170 degrees), fast response speed, thin thickness, small volume, light weight, use of a flexible substrate, low-voltage direct current driving (3-10V), low power consumption, wide working temperature range and the like, which are not in ethical proportion, so that the organic electroluminescent diodes (OLEDs) have wide application markets, such as lighting systems, communication systems, vehicle-mounted displays, portable electronic devices, high-definition displays and even military fields.
Materials used for OLEDs are classified into fluorescent materials and phosphorescent materials according to the mechanism of light emission. According to the spin quantum statistical theory, the ratio of singlet and triplet excitons formed after recombination of electrons and holes is 1:3, and thus the maximum internal quantum efficiency of fluorescence emitted by radiative decay of singlet excitons is 25%. And the phosphorescent material can realize phosphorescence emission of mixed singlet state and triplet state through intersystem crossing, so that the theoretical internal quantum efficiency of the PHOOLED is 100%.
In order to realize high efficiency of phosphorescent devices, the light emitting layer in the organic light emitting diode currently adopts a host-guest structure, i.e. a guest light emitting material is dispersed in a host material, and energy is transferred to the guest light emitting material through the host light emitting material to emit light, so that concentration quenching and triplet-triplet annihilation are reduced. Therefore, it is generally required that the energy gap of the host material should be larger than that of the guest emitter material, otherwise it is easy to cause energy to be transferred from the guest emitter to the host material to reduce the efficiency of the device; in addition, the main material has higher requirements on crystallization performance and glass transition temperature.
In fact, although the application range of OLEDs is continuously expanded, there still exist disadvantages, for example, some existing OLED materials have a series of problems of insufficient hole transport property, low luminous efficiency, low thermal stability, narrow energy band, low solubility, etc., and the fundamental factor determining the performance of OLEDs is the choice of materials, so that designing and searching a compound as a novel OLED material to overcome the disadvantages in the practical application process is a key point in the research work of OLED materials and the future development trend.
Disclosure of Invention
In order to better embody the epoch-making technical advantages of the OLED over the TFT-LCD and solve the problems occurring in the prior art of the OLED material in the practical application process, the present invention aims to design and provide a series of organic electroluminescent compounds with excellent properties for the electroluminescent material.
Accordingly, in a first aspect of the present invention, there is provided a silafluorene derivative for use in an electroluminescent material, which has a structure represented by general formula (i):
wherein R is1～R7Each independently selected from: H. C1-C8 alkanyl, C1-C8 alkoxy, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heterocyclic aryl, or-NR8R9And R is8、R9Each independently selected from C1-C8 alkanyl, C1-C8 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C6-C30 heterocyclic aryl;
wherein X is N or P.
Preferably, in the above general formula (I), R is1And R2Each independently selected from: H. C1-C3 alkanyl, C1-C2 alkoxy, cyano, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C6-C14 heterocyclic aryl, or-NR8R9And R is8、R9Each independently selected from: methyl, ethyl, methoxy, phenyl, p-tolyl, o-tolyl, m-tolyl, p-cyanophenyl, o-cyanophenyl, m-cyanophenyl.
Preferably, in the above general formula (I), R is3And R4Each independently selected from: H. C1-C3 alkanyl, C1-C2 alkoxy, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted C6-C18 heterocyclic aryl.
Preferably, in the above general formula (I), R is5、R6、R7Selected from: H. C1-C3 alkanyl, C1-C2 alkoxy, cyano, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C6-C14 heterocyclic aryl, and the R5、R6、R7At least two of which are simultaneously H.
Further preferably, said R5、R6、R7Are all H.
Still further preferably, the structure of the silafluorene derivative is selected from any one of the following:
in a second aspect of the present invention, there is provided a light emitting host material for an OLED light emitting layer containing the above silafluorene derivative.
In a third aspect of the invention, an OLED electron transport layer material containing the silafluorene derivative is provided.
In a fourth aspect of the present invention, there is provided an OLED hole transport layer material containing the above silafluorene derivative.
In a fifth aspect of the present invention, there is provided an OLED device containing the above silafluorene derivative.
The invention provides a silafluorene derivative based on a structure shown in a general formula (I), which is mainly used as a light-emitting main material. In addition, the silafluorene derivative with the structure shown in the general formula (I) has a simple structure, is easy to synthesize, can effectively reduce the preparation cost of the OLED material, and has good industrial prospect. The silafluorene derivative containing the structure shown in the general formula (I) can be used for a luminescent layer, an electron transport layer, a hole transport layer and the like, and has the advantages of wide energy band, high glass transition temperature, difficulty in crystallization and the like, so that the OLED display screen can achieve the effects of high brightness, high efficiency and low power consumption.
Detailed Description
The present invention will be further described with reference to specific embodiments, but the present invention is not limited to the following embodiments.
In a first aspect of the present invention, a silafluorene derivative for electroluminescent material is provided, which has a structure represented by general formula (i):
wherein R is1～R7Each independently selected from: H. C1-C8 alkanyl, C1-C8 alkoxy, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heterocyclic aryl, or-NR8R9And R is8、R9Each independently selected from C1-C8 alkanyl, C1-C8 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C6-C30 heterocyclic aryl;
wherein X is N or P.
In a preferred embodiment, said R1And R2Each independently selected from: H. C1-C3 alkanyl, C1-C2 alkoxy, cyano, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C6-C14 heterocyclic aryl, or-NR8R9And R is8、R9Each independently selected from: methyl, ethyl, methoxy, phenyl, p-tolyl, o-tolyl, m-tolyl, p-cyanophenyl, o-cyanophenyl, m-cyanophenyl.
In a preferred embodiment, said R3And R4Each independently selected from: H. C1-C3 alkanyl, C1-C2 alkoxy, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted C6-C18 heterocyclic aryl.
In a preferred embodiment, said R5、R6、R7Selected from: H. C1-C3 alkanyl, C1-C2 alkoxy, cyano, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C6-C14 heterocyclic aryl, and the R5、R6、R7At least two of which are simultaneously H.
In a further preferred embodiment, said R is5、R6、R7Are all H.
In a still further preferred embodiment, the structure of the silafluorene derivative is selected from any one of the following:
in a second aspect of the present invention, there is provided a light emitting host material for an OLED light emitting layer containing the above silafluorene derivative.
In a third aspect of the invention, an OLED electron transport layer material containing the silafluorene derivative is provided.
In a fourth aspect of the present invention, there is provided an OLED hole transport layer material containing the above silafluorene derivative.
In a fifth aspect of the present invention, there is provided an OLED device containing the above silafluorene derivative.
The present invention is further illustrated below with reference to specific examples, wherein the process is conventional unless otherwise specified; the starting materials are commercially available from the open literature unless otherwise specified.
EXAMPLE 1 preparation of Compound 5
Dissolving compound A-1(31.2g, 100mmol) in anhydrous ether (300ml), and cooling to-78 deg.C under nitrogen protection; then butyllithium (1.6mol/L, 128ml, 205mmol) was slowly added dropwise, followed by stirring at-78 ℃ for 1 hour, and silicon tetrachloride (17.0g, 100mmol) was slowly added dropwise to the reaction solution; the reaction mixture was kept at low temperature (-78 ℃) for 1 hour and then naturally warmed to room temperature to obtain a crude product of the compound A-2, which was used in the next reaction without purification.
(2) Synthesis of Compound A-4
Compound a-3(17.2g, 100mmol), o-bromoiodobenzene (31.1g, 110mmol) and potassium carbonate (41.4g, 300mmol) were added to acetonitrile (500ml) and refluxed for 12 hours, then cooled to room temperature, filtered, the mother liquor was collected, water (100ml) was added and stirred for half an hour, followed by extraction with ethyl acetate (200ml x 3), the organic phases were combined, washed with water (50ml x 2), dried, and concentrated to give a yellow liquid, i.e. said compound a-4, weighed 32.8g, with HPLC assay content 98.2%, which was used directly in the next reaction.
(3) Synthesis of Compound A-5
Compound a-4(32.8g, 100mmol), 4-iodotoluene (23.0g, 110mmol) and potassium carbonate (41.4g, 300mmol) were added to acetonitrile (500ml) and refluxed for 12 hours, then cooled to room temperature, poured into ice water, extracted with ethyl acetate (300ml x 2), the organic phases combined, washed with water (30ml x 2), dried, concentrated, and the crude product washed with diethyl ether (30ml x 2) to give a white solid, i.e. said compound a-5, weighed 32.1g, content by HPLC 99.8%, yield 77%.
(4) Synthesis of Compound 5
Dissolving compound A-5(35g, 83.9mmol) in tetrahydrofuran (350ml) and cooling to-78 deg.C under nitrogen protection; slowly dropping butyl lithium (1.6mol/L, 108ml, 172mmol) and maintaining at low temperature (-78 ℃) for 30 minutes, then slowly dropping the A-2 crude product solution into the reaction system and maintaining at low temperature (-78 ℃) for 1 hour; then, the reaction mixture was slowly warmed to room temperature, poured into ice water, extracted with ethyl acetate (200ml × 3), and the organic phases were combined, washed with water (30ml × 3), dried, concentrated, recrystallized 2 times with toluene, and sublimed 2 times to obtain the target compound 5, which was weighed 21.3g, had a content of 99.87% by HPLC, and a yield of 58.2%.1H NMR(DMSO-d6，δ)＝7.60-7.58(4H)，7.42(2H)，7.32-7.29(4H),7.11(2H),6.81-6.72(4H),6.56-6.34(4H),2.35(3H)。
Example 2 preparation of OLED devices containing Compound 18
Ultrasonically cleaning a transparent anode electrode ITO substrate in isopropanol for 5-10 minutes, exposing the transparent anode electrode ITO substrate to ultraviolet light for 20-30 minutes, treating the transparent anode electrode ITO substrate with plasma for 5-10 minutes, and then putting the treated ITO substrate into evaporation equipment for evaporation: firstly, evaporating a layer of NPB (nitrogen-phosphorus) with the thickness of 30-50 nm as a hole transport layer; then mixing and evaporating a compound 18 and 5-10% of TBPe to be used as a light-emitting layer; then evaporating 20-40 nm Alq 3; then evaporating 0.5-2 nm LiF; and finally, evaporating 100-200 nm of metal Al to obtain an OLED device S1: ITO/NPB/Compound 18 TBPe/Alq 3/LiF/Al.
Example 3 preparation of an OLED device containing Compound 20
Ultrasonically cleaning a transparent anode electrode ITO substrate in isopropanol for 5-10 minutes, exposing the transparent anode electrode ITO substrate to ultraviolet light for 20-30 minutes, treating the transparent anode electrode ITO substrate with plasma for 5-10 minutes, and then putting the treated ITO substrate into evaporation equipment for evaporation: firstly, evaporating a layer of NPB (nitrogen-phosphorus) with the thickness of 30-50 nm as a hole transport layer; then mixing and evaporating a compound 20 and 5-10% of TBPe to be used as a light-emitting layer; then evaporating 20-40 nm Alq3 to be used as an electron transport layer; then evaporating 0.5-2 nm LiF; and finally, evaporating 100-200 nm of metal Al to obtain an OLED device S2: ITO/NPB/Compound 20 TBPe/Alq 3/LiF/Al.
Example 4 preparation of OLED devices containing Compound 22
Ultrasonically cleaning a transparent anode electrode ITO substrate in isopropanol for 5-10 minutes, exposing the transparent anode electrode ITO substrate to ultraviolet light for 20-30 minutes, treating the transparent anode electrode ITO substrate with plasma for 5-10 minutes, and then putting the treated ITO substrate into evaporation equipment for evaporation: firstly, evaporating a layer of NPB (nitrogen-phosphorus) with the thickness of 30-50 nm as a hole transport layer; then mixing and evaporating a compound 22 and 5-10% of TBPe to be used as a light-emitting layer; then evaporating 20-40 nm Alq3 to be used as an electron transport layer; then evaporating 0.5-2 nm LiF; and finally, evaporating 100-200 nm of metal Al to obtain an OLED device S3: ITO/NPB/Compound 22 TBPe/Alq 3/LiF/Al.
Example 5 preparation of OLED devices containing Compound 24
Ultrasonically cleaning a transparent anode electrode ITO substrate in isopropanol for 5-10 minutes, exposing the transparent anode electrode ITO substrate to ultraviolet light for 20-30 minutes, treating the transparent anode electrode ITO substrate with plasma for 5-10 minutes, and then putting the treated ITO substrate into evaporation equipment for evaporation: firstly, evaporating a layer of NPB (nitrogen-phosphorus) with the thickness of 30-50 nm as a hole transport layer; then, performing mixed evaporation on CBP and 5-10% of TBPe to serve as a light-emitting layer; then evaporating a 20-40 nm compound 24 as an electron transport layer; then evaporating 0.5-2 nm LiF; and finally, evaporating 100-200 nm of metal Al to obtain an OLED device S4: ITO/NPB/CBP TBPe/compound 24/LiF/Al.
Example 6 preparation of OLED devices containing Compound 26
Ultrasonically cleaning a transparent anode electrode ITO substrate in isopropanol for 5-10 minutes, exposing the transparent anode electrode ITO substrate to ultraviolet light for 20-30 minutes, treating the transparent anode electrode ITO substrate with plasma for 5-10 minutes, and then putting the treated ITO substrate into evaporation equipment for evaporation: firstly, evaporating a layer of NPB (nitrogen-phosphorus) with the thickness of 30-50 nm as a hole transport layer; then, performing mixed evaporation on CBP and 5-10% of TBPe to serve as a light-emitting layer; then evaporating a compound 26 with the thickness of 20-40 nm as an electron transport layer; then evaporating 0.5-2 nm LiF; and finally, evaporating 100-200 nm of metal Al to obtain an OLED device S5: ITO/NPB/CBP TBPe/compound 26/LiF/Al.
Example 7 preparation of an OLED device containing Compound 28
Ultrasonically cleaning a transparent anode electrode ITO substrate in isopropanol for 5-10 minutes, exposing the transparent anode electrode ITO substrate to ultraviolet light for 20-30 minutes, treating the transparent anode electrode ITO substrate with plasma for 5-10 minutes, and then putting the treated ITO substrate into evaporation equipment for evaporation: firstly, evaporating a layer of NPB (nitrogen-phosphorus) with the thickness of 30-50 nm as a hole transport layer; then, performing mixed evaporation on CBP and 5-10% of TBPe to serve as a light-emitting layer; then evaporating a compound 28 with the thickness of 20-40 nm as an electron transport layer; then evaporating 0.5-2 nm LiF; and finally, evaporating 100-200 nm of metal Al to obtain an OLED device S6: ITO/NPB/CBP TBPe/compound 28/LiF/Al.
Example 8 preparation of an OLED device containing Compound 30
Ultrasonically cleaning a transparent anode electrode ITO substrate in isopropanol for 5-10 minutes, exposing the transparent anode electrode ITO substrate to ultraviolet light for 20-30 minutes, treating the transparent anode electrode ITO substrate with plasma for 5-10 minutes, and then putting the treated ITO substrate into evaporation equipment for evaporation: firstly, evaporating a layer of 30-50 nm compound 30 as a hole transport layer; then, performing mixed evaporation on CBP and 5-10% of TBPe to serve as a light-emitting layer; then evaporating 20-40 nm Alq3 to be used as an electron transport layer; then evaporating 0.5-2 nm LiF; and finally, evaporating 100-200 nm of metal Al to obtain an OLED device S7: ITO/Compound 30/CBP TBPe/Alq 3/LiF/Al.
Example 9 preparation of OLED devices containing Compound 32
Ultrasonically cleaning a transparent anode electrode ITO substrate in isopropanol for 5-10 minutes, exposing the transparent anode electrode ITO substrate to ultraviolet light for 20-30 minutes, treating the transparent anode electrode ITO substrate with plasma for 5-10 minutes, and then putting the treated ITO substrate into evaporation equipment for evaporation: firstly, evaporating a layer of 30-50 nm compound 32 as a hole transport layer; then, performing mixed evaporation on CBP and 5-10% of TBPe to serve as a light-emitting layer; then evaporating 20-40 nm Alq3 to be used as an electron transport layer; then evaporating 0.5-2 nm LiF; and finally, evaporating 100-200 nm of metal Al to obtain an OLED device S8: ITO/Compound 32/CBP TBPe/Alq 3/LiF/Al.
Wherein, the structural formulas of the used compounds CBP, NPB and TBPe are as follows:
comparative example of OLED device
And ultrasonically cleaning the transparent anode electrode ITO substrate in isopropanol for 5-10 minutes, exposing the transparent anode electrode ITO substrate to ultraviolet light for 20-30 minutes, and then treating the transparent anode electrode ITO substrate with plasma for 5-10 minutes. And then putting the processed ITO substrate into evaporation equipment for evaporation: firstly, evaporating a layer of NPB (nitrogen-phosphorus) with the thickness of 30-50 nm as a hole transport layer; then, mixing and evaporating CBP and 5-10% of Ir (ppy)3 to be used as a hole transport layer; then evaporating 20-40 nm Alq3 as an electron transport layer; then evaporating 0.5-2 nm LiF; and finally, evaporating 100-200 nm of metal Al to obtain an OLED device D: ITO/NPB/CBP TBPe/Alq 3/LiF/Al.
The OLED devices S1-S8 and the OLED device D are detected under 1000nits, and the detection results are shown in the following table 1, wherein Driver Voltage represents driving Voltage, Cd/A represents luminous flux per unit area, and CIEx and CIEy represent color coordinates:
| OLED device | Cd/A | Driver Voltage | CIEx | CIEy |
| D | 6.5 | 4.7V | 0.12 | 0.64 |
| S1 | 7.2 | 4.1V | 0.13 | 0.64 |
| S2 | 6.9 | 4.2V | 0.13 | 0.64 |
| S3 | 6.6 | 3.9V | 0.13 | 0.64 |
| S4 | 7.5 | 4.0V | 0.13 | 0.64 |
| S5 | 6.9 | 4.3V | 0.13 | 0.64 |
| S6 | 7.2 | 4.3V | 0.13 | 0.64 |
| S7 | 7.3 | 4.5V | 0.13 | 0.64 |
| S8 | 7.3 | 4.1V | 0.13 | 0.64 |
TABLE 1
The data presented in table 1 demonstrate that OLED devices containing the silafluorene derivatives of the present invention require lower driving voltages, greater luminous flux per unit area, and thus higher luminous efficiency and better color coordinates than comparative OLED devices.
The embodiments of the present invention have been described in detail, but the embodiments are merely examples, and the present invention is not limited to the embodiments described above. Any equivalent modifications and substitutions to those skilled in the art are also within the scope of the present invention. Accordingly, equivalent changes and modifications made without departing from the spirit and scope of the present invention should be covered by the present invention.
Claims (5)
1. A silafluorene derivative for use in an electroluminescent material, wherein the structure of the silafluorene derivative is selected from any one of the following:
2. a light emitting host material of an OLED light emitting layer containing the silafluorene derivative of claim 1.
3. An OLED electron transport layer material containing the silafluorene derivative of claim 1.
4. An OLED hole transport layer material containing the silafluorene derivative of claim 1.
5. An OLED device containing the silafluorene derivative of claim 1.
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| KR102607902B1 (en) | 2018-05-28 | 2023-11-30 | 삼성디스플레이 주식회사 | Organic electroluminescence device and monoamine compound for organic electroluminescence device |
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| CN101035878A (en) * | 2004-09-24 | 2007-09-12 | Lg化学株式会社 | New compound and organic light emitting device using the same(10) |
| CN104326980A (en) * | 2014-09-16 | 2015-02-04 | 武汉大学 | 9,9'- connected host material based on 4,4'-difluorene structure and application thereof |
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Address after: 201506, No. nine, No. 1568, Jinshan Industrial Zone, Shanghai, Jinshan District Patentee after: Shanghai Hehui optoelectronic Co., Ltd Address before: 201506, No. nine, No. 1568, Jinshan Industrial Zone, Shanghai, Jinshan District Patentee before: EverDisplay Optronics (Shanghai) Ltd. |