CN114989170A - Compound with 5,10- [1,2] phenazine derivative as core and application thereof - Google Patents

Compound with 5,10- [1,2] phenazine derivative as core and application thereof Download PDF

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CN114989170A
CN114989170A CN202210797970.3A CN202210797970A CN114989170A CN 114989170 A CN114989170 A CN 114989170A CN 202210797970 A CN202210797970 A CN 202210797970A CN 114989170 A CN114989170 A CN 114989170A
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organic electroluminescent
phenazine derivative
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郭强
孙军
张宏科
刘凯鹏
田密
何海晓
杨丹丹
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Xi'an Manareco New Materials Co ltd
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Abstract

The present invention belongs to the field of organic electroluminescent material technology, and is especially one kind of 5,10- [1,2] organic electroluminescent material]A compound with a phenazine derivative as a core and application thereof. The compound is shown as a formula (I), wherein X is a single bond or CR 1 R 2 ，R 1 、R 2 Independently selected from methyl; l is aryl; d is a typical electron donating group. The present invention provides a new kind of medicine composition 5,10- [1,2]]The compound with the phenazine derivative as the core has electron donating property and is suitableHOMO/LUMO values and higher triplet energy values, can be used to prepare high performance organic EL devices.
Figure DDA0003732850960000011

Description

Compound with 5,10- [1,2] phenazine derivative as core and application thereof
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and relates to a compound taking 5,10- [1,2] phenazine derivatives as cores and application thereof.
Background
With the advent of the information age, the research on new displays with human-computer interfaces has attracted more and more attention, especially the technology of various flat panel display devices. Organic Light Emitting Diodes (OLEDs) belong to a novel photoelectric information technology, and are used as self-luminous electronic elements, and the OLED Light Emitting mechanism is that under the action of a direct current electric field, electric energy is directly converted into Light energy by means of Organic semiconductor functional materials. The color of the emitted light of the OLED can be red, green, blue, yellow alone or in combination with white light. The OLED light-emitting display technology has the biggest characteristics of ultra-thin property, high response speed, ultra-light weight, surface light-emitting property and flexible display, can be used for manufacturing monochromatic or full-color displays, and can also be used for manufacturing illumination, display products or backlight sources of liquid crystal displays. The OLED light emitting display technology is considered as a new flat panel display device that can replace the liquid crystal display, and has become a hot spot for research and development of new materials and display technology field in recent years. With the continuous optimization of the structure of the organic electroluminescent device, a multifunctional hierarchical structure is gradually formed, and the efficiency and the stability of the device are greatly improved.
The hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer in the organic electroluminescent device are mainly used for reducing a potential barrier between an electrode and a light-emitting layer and improving the injection rate and the transmission rate of holes and electrons, so that the power consumption of the device is reduced, the luminous efficiency of the device is improved, and the service life of the device is prolonged. The material and structure of the organic electroluminescent device directly determine the deviceHigh efficiency and short service life. CN108315010B discloses the use of dibenzophenazines of the formula as phosphorescent materials, in particular as room temperature phosphorescent materials
Figure BDA0003732850940000021
The invention also relates to an organic electroluminescent device using dibenzophenazine as a phosphorescent material; dibenzophenazine as a pure organic nitrogen heterocyclic room temperature phosphorescent material without heavy atoms can realize a novel pure organic electrophosphorescent material with high efficiency and direct exciton utilization. However, the compound disclosed in CN108315010B is only single in function as a phosphorescent material, and its structure is not stable enough, so it is difficult to reduce quenching and molecular vibration caused by molecular aggregation, and the performance of the prepared organic electroluminescent device is difficult to meet the market requirement.
The compound with 5,10- [1,2] phenazine derivative as core has electron donating characteristic, proper HOMO/LUMO value and high triplet state energy value, and can improve the performance of organic electroluminescent device greatly. The organic electroluminescent material has important value for manufacturing organic electroluminescent elements and developing organic electroluminescent display technology.
Disclosure of Invention
The invention aims to provide a compound taking 5,10- [1,2] phenazine derivative as a core, which is applied to an organic electroluminescent device as a hole transport material or a luminescent material to improve the device performance of the organic electroluminescent device.
In view of the above, the present application addresses this need in the art by providing a compound having a 5,10- [1,2] phenazine derivative as a core and uses thereof.
The present invention provides a new compound 5,10- [1,2]]The compound with the phenazine derivative as the core can effectively inhibit pi-pi accumulation due to the specific rigidity and spatial three-dimensional structure of the compound, reduce quenching and molecular vibration caused by molecular aggregation, and has more stable molecular structure. The nitrogen atom in the molecule of the compound has the electron-withdrawing characteristic different from C, Si and P atoms, and the parent nucleus structure has the amino property due to the existence of two N atoms, so that air can be effectively transferredThe hole, further the acridine ring or the carbazole ring can improve the hole transmission capability of the mother nucleus structure, and on the basis, the electron-donating groups such as amino, carbazolyl and the like are introduced to construct the material with typical hole transmission performance. The material has proper molecular front linear orbital energy level and higher triplet state energy (T) 1 ) The organic electroluminescent material can be used as a hole transport material and a luminescent material, improves the device performance of an organic electroluminescent device, and has wide application market prospect.
On one hand, the invention provides a compound taking 5,10- [1,2] phenazine derivative as a core, and the structural general formula of the compound is shown as the formula (I):
Figure BDA0003732850940000031
wherein X is a single bond or CR 1 R 2 ，R 1 、R 2 Independently selected from methyl; l is aryl; d is a typical electron donating group; the typical electron donating group is selected from substituted or unsubstituted amine group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted phenoxazinyl group, substituted or unsubstituted acridinyl group, substituted or unsubstituted 10H spiro [ acridine-9, 9' -fluorene]Substituted or unsubstituted 10H spiro [ acridine-9, 9' -xanthene]A substituted or unsubstituted 5-phenyl-5, 10-dihydrophenazinyl group, a substituted or unsubstituted 10H-phenothiazinyl group.
Preferably, in the compound with the 5,10- [1,2] phenazine derivative as the core, L is an aryl group, and the aryl group is one of phenyl, naphthyl, anthryl and pyrenyl.
Furthermore, in the compound taking the 5,10- [1,2] phenazine derivative as the core, the structural general formula is shown as a formula (II) or a formula (III):
Figure BDA0003732850940000041
further, in the compound having a 5,10- [1,2] phenazine derivative as a core, D is selected from structures represented by any one of formulas (1) to (7):
Figure BDA0003732850940000042
Figure BDA0003732850940000043
specifically, Ar is 1 、Ar 2 Is represented by one of phenyl, biphenyl, carbazolyl and furyl; the R is 1 And R 2 Is represented by one of methyl, ethyl, tertiary butyl, phenyl, biphenyl, carbazolyl and furyl.
Furthermore, the compound taking the 5,10- [1,2] phenazine derivative as the core provided by the invention has a specific structure as any one of the following compounds 1-18:
Figure BDA0003732850940000044
Figure BDA0003732850940000051
Figure BDA0003732850940000061
furthermore, the compound taking the 5,10- [1,2] phenazine derivative as the core provided by the invention has a specific structure as any one of the following compounds 19-41:
Figure BDA0003732850940000062
Figure BDA0003732850940000071
furthermore, the compound taking the 5,10- [1,2] phenazine derivative as the core provided by the invention has a specific structure as any one of the following compounds 42-47:
Figure BDA0003732850940000081
the invention provides a series of compounds taking 5,10- [1,2] phenazine derivatives as cores, the 5,10- [1,2] phenazine derivatives are adopted as the core parent nucleus of the core, electron-donating groups such as amido, carbazolyl and the like are further introduced, and the constructed compounds have typical electron-donating characteristics. The compound provided by the invention is proved to have outstanding performance through T1 energy level and HOMO and LUMO energy level tests, and is suitable for being used as a hole transport material or a luminescent material. The organic electroluminescent device prepared by using the compound provided by the invention as a hole transport material or a luminescent material is found to have excellent performance through performance tests, and has good performance in improving photoelectric properties such as luminous efficiency, brightness and the like of the device. The invention further claims an organic electroluminescent material containing the compound which takes the 5,10- [1,2] phenazine derivative as the core; an organic electroluminescent element comprises an anode, a cathode, and a luminescent layer, an electron transport layer and a hole transport layer, wherein the hole transport layer, the luminescent layer and the electron transport layer are arranged between the anode and the cathode; specifically, the light emitting layer is any one of a phosphorescent device, a fluorescent device, and a thermally active delayed fluorescent device. And the application of the organic electroluminescent material or the organic electroluminescent element in organic electroluminescent display is claimed.
Compared with the prior art, the invention has the following beneficial effects or advantages:
the invention provides a plurality of compounds taking 5,10- [1,2] phenazine derivatives as cores and provides a synthesis method of the compounds taking the 5,10- [1,2] phenazine derivatives as cores. The compound taking the 5,10- [1,2] phenazine derivative as the donor is further modified by an electron donating group to form a structure with a typical hole transport property, has a proper HOMO/LUMO value and a higher triplet state energy value, and can be used for preparing a high-performance organic EL element. The compound taking the 5,10- [1,2] phenazine derivative as the core has higher thermal stability by adding the spatial three-dimensional structure, can obviously improve the luminous stability of a light-emitting device, is suitable for being used as a hole transport material and a light-emitting layer material, and has wide application prospect in OLED light-emitting devices and display devices.
Drawings
Fig. 1 is a schematic structural diagram of an organic electroluminescent device provided in an embodiment of the present invention.
Description of reference numerals: 1 is a substrate, 2 is an anode layer, 3 is a hole injection layer, 4 is a first hole transport layer, 5 is a second hole transport layer, 6 is a light emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer.
Detailed Description
The following examples are given to illustrate the technical means of the present invention, but the present invention is not limited to the following examples.
In order to make the technical solutions of the present invention better understood and implemented by those skilled in the art, the present invention is further described below with reference to the following specific embodiments and the accompanying drawings, but the embodiments are not meant to limit the present invention.
The experimental methods and the detection methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
Example 1
This example provides methods and procedures for the synthesis of compound 1, compound 2, compound 3, compound 30, compound 37, compound 42, and intermediates involved.
(1) Synthesis of intermediates 1 to 3
Figure BDA0003732850940000101
300g of intermediate 1-2, 1170.5g of intermediate 1-1, 1004.1g of potassium carbonate and 8L of toluene are sequentially added into a three-neck flask, nitrogen is introduced to replace air in the reaction flask, 34.5g of cuprous iodide and 32.8g of 1, 10-phenanthroline are added, and the reaction solution is heated to 110 ℃ and is refluxed and stirred for reaction for 8 hours. After cooling to room temperature, the reaction solution was washed with water to neutrality, and the organic phase was dried over anhydrous sodium sulfate and purified through a silica gel column to obtain 337.8g of intermediate 1-3 with a yield of 62.7%.
Figure BDA0003732850940000102
200g of intermediate 1-3, 99.5g of intermediate 1-4, 3L of toluene are sequentially added into a three-necked bottle, after nitrogen is introduced to replace the air in the reaction bottle, 16.6g of 1, 1' -bis (diphenylphosphino) ferrocene, 6.7g of palladium acetate and 86.2g of sodium tert-butoxide are added, and the mixture is heated to reflux and stirred for reaction for 6 hours. Cooling to room temperature, washing to neutrality, and distilling at normal pressure to remove toluene. The obtained solid was purified by a silica gel column to obtain 177.6g of intermediate 1-5 with a yield of 73.2%.
Figure BDA0003732850940000111
170g of intermediate 1-5, 2L tetrahydrofuran is sequentially added into a three-necked flask, and after the temperature is reduced to-78 ℃, nitrogen is introduced to replace the air in the reaction flask. 629.3mL of 3.0M methylmagnesium bromide solution in 2-methyltetrahydrofuran is slowly dropped into the solution, the temperature is raised to room temperature, the mixture is stirred and reacts for 12 hours, then distilled water is added to quench the reaction, and toluene is added to extract. The organic phase was washed with water to neutrality, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column to obtain 95.4g of intermediates 1 to 6 with a yield of 56.1%.
Figure BDA0003732850940000112
Adding 90g of intermediate 1-6 and 1L of polyphosphoric acid into a three-necked bottle obtained after nitrogen replacement in sequence, heating to 60 ℃, stirring for reacting for 8h, cooling to room temperature, slowly pouring into 3L of ice water under stirring, and continuously stirring for 0.5 h. The precipitated solid was filtered, and the filter cake was dissolved in toluene, washed with water to neutrality, and then dried over anhydrous sodium sulfate. The solution was concentrated, purified by silica gel column and recrystallized to give 57.9g of intermediate 1, yield 67.3%.
Figure BDA0003732850940000113
100g of intermediate 1-3, 41.8g of intermediate 2-1 and 1.5L of toluene are sequentially added into a three-neck flask, 8.3g of 1, 1' -bis (diphenylphosphino) ferrocene, 3.4g of palladium acetate and 43.1g of sodium tert-butoxide are added after the air in the reaction flask is replaced by nitrogen, and the mixture is heated to reflux and stirred for reaction for 6 hours. Cooling to room temperature, washing to neutrality, and distilling at normal pressure to remove toluene. The resulting solid was purified by silica gel column to give 87.0g of intermediate 2-2 in 76.3% yield.
Figure BDA0003732850940000121
85g of intermediate 2-2, 61.6g of potassium carbonate, 6.8g of pivalic acid and 1 LN-methylpyrrolidone are added in sequence to a three-necked flask. Introducing nitrogen to replace the air in the reaction bottle, adding 2.5g of palladium acetate and 20.0mL of 30% toluene solution of tri-tert-butylphosphine, heating to 128-130 ℃, reacting for 6h, and cooling to room temperature. Adding 3L of water into the reaction solution, stirring to separate out a solid, dissolving a filter cake after filtration in toluene, washing with water to neutrality, drying with anhydrous sodium sulfate, concentrating by reduced pressure distillation, purifying by a silica gel column, and recrystallizing to obtain 60.6g of the intermediate 2 with the yield of 78.7%.
(2) Synthesis of Compound 1
Figure BDA0003732850940000122
10g of intermediate 2, 11.2g of intermediate 1-1, 7.8g of potassium carbonate and 200mL of toluene are sequentially added into a three-mouth bottle, nitrogen is introduced to replace air in the reaction bottle, 0.41g of cuprous bromide and 0.52g of 1, 10-phenanthroline are added, and the reaction solution is heated to 110 ℃ and is refluxed and stirred for reaction for 8 hours. After cooling to room temperature, the reaction mixture was washed with water to neutrality, and the organic phase was dried over anhydrous sodium sulfate and purified over a silica gel column to give 14.0g of compound 1 in 82.2% yield.
1 H NMR(400MHz,CDCl3)δ8.23(d,J＝8.0,2H),8.21(d,J＝8.0,1H),8.12(s,1H),7.88(d,J＝6.4,2H),7.91(d,J＝6.4,2H),7.52-7.57(m,6H),7.13-7.19(m,8H),6.96(d,J＝7.2,4H)。
(3) Synthesis of Compound 2
Figure BDA0003732850940000131
10g of intermediate 2, 11.2g of intermediate 1-1, 7.8g of potassium carbonate and 200mL of toluene are sequentially added into a three-mouth bottle, nitrogen is introduced to replace air in the reaction bottle, 0.41g of cuprous bromide and 0.52g of 1, 10-phenanthroline are added, and the reaction solution is heated to 110 ℃ and is refluxed and stirred for reaction for 8 hours. After cooling to room temperature, the reaction mixture was washed with water to neutrality, and the organic phase was dried over anhydrous sodium sulfate and purified by silica gel column to obtain 13.4g of compound 2 with a yield of 78.5%.
1 H NMR(400MHz,CDCl3)δ8.21(d,J＝8.0,1H),8.12(s,1H),7.76(d,J＝6.4,2H),7.61(d,J＝6.8,1H),7.51(t,J＝6.8,1H),7.42(d,J＝6.4,2H),7.19-7.23(m,5H),7.15(s,1H),7.04-7.10(m,8H),6.95-7.00(m,6H)。
(4) Synthesis of Compound 3
Figure BDA0003732850940000141
10g of the intermediate 2, 16.7g of the intermediate 3-1, 7.8g of potassium carbonate and 200mL of toluene are sequentially added into a three-mouth bottle, nitrogen is introduced to replace air in the reaction bottle, 0.41g of cuprous bromide and 0.52g of 1, 10-phenanthroline are added, and the reaction solution is heated to 110 ℃ and is refluxed and stirred for reaction for 8 hours. After cooling to room temperature, the reaction mixture was washed with water to neutrality, and the organic phase was dried over anhydrous sodium sulfate and purified by silica gel column to obtain 16.5g of compound 3 with a yield of 75.9%.
1 H NMR(400MHz,CDCl3)δ8.21(d,J＝8.0,1H),8.12(s,1H),7.97(d,J＝6.8,2H),7.73(d,J＝6.4,2H),7.61(d,J＝6.8,1H),7.57(d,J＝6.8,2H),7.51(t,J＝6.8,1H),7.45(t,J＝6.8,2H),7.40(d,J＝6.4,2H),7.32(t,J＝6.8,2H),7.15-7.22(m,8H),7.09(d,J＝6.8,4H),6.94-7.00(m,6H)。
(5) Synthesis of Compound 30
Figure BDA0003732850940000142
The intermediate 30-1 can be obtained by the synthesis method of the intermediate 1-3. 10g of the intermediate 1, 10.9g of the intermediate 30-1, 5.0g of sodium tert-butoxide and 200mL of toluene are sequentially added into a three-necked flask, nitrogen is introduced to replace the air in the reaction flask, 0.3g of palladium acetate and 2.4mL of 30% toluene solution of tri-tert-butylphosphine are added, and the mixture is heated to reflux reaction for 6 hours. Cooling to room temperature, washing to neutrality, drying with anhydrous sodium sulfate, purifying with silica gel column, and recrystallizing to obtain 12.3g of compound 30 with a yield of 72.6%.
1 H NMR(400MHz,CDCl3)δ7.92(s,1H),7.36-7.40(m,4H),7.21-7.26(m,6H),7.13-7.17(m,5H),7.02-7.08(m,6H),6.95(d,J＝6.8,4H),2.37(s,6H),1.62(s,6H)。
(6) Synthesis of Compound 37
Figure BDA0003732850940000151
Intermediate 37-1 can be obtained by the synthesis method of intermediate 1-3 described above. 10g of the intermediate 1, 15.1g of the intermediate 37-1, 5.0g of sodium tert-butoxide and 200mL of toluene are sequentially added into a three-necked flask, nitrogen is introduced to replace the air in the reaction flask, 0.3g of palladium acetate and 2.4mL of 30% toluene solution of tri-tert-butylphosphine are added, and the mixture is heated to reflux reaction for 6 hours. Cooling to room temperature, washing to neutrality, drying with anhydrous sodium sulfate, purifying with silica gel column, and recrystallizing to obtain 15.4g of compound 37 with yield of 75.2%.
1 H NMR(400MHz,CDCl3)δ7.92(s,1H),7.38-7.43(m,4H),7.30-7.35(m,4H),7.19-7.26(m,10H),7.13-7.16(m,5H),7.02-7.10(m,8H),6.94(d,J＝6.8,4H),1.60(s,6H)。
(7) Synthesis of Compound 42
Figure BDA0003732850940000161
Intermediate 42-1 can be obtained by the synthesis method of intermediate 1-3 described above. 10g of intermediate 2, 12.6g of intermediate 42-1, 7.8g of potassium carbonate and 200mL of toluene are sequentially added into a three-mouth bottle, nitrogen is introduced to replace air in the reaction bottle, 0.41g of cuprous bromide and 0.52g of 1, 10-phenanthroline are added, and the reaction solution is heated to 110 ℃ and is refluxed and stirred for reaction for 8 hours. After cooling to room temperature, the reaction mixture was washed with water to neutrality, and the organic phase was dried over anhydrous sodium sulfate and purified by silica gel column to obtain 14.1g of compound 42 with a yield of 77.3%.
1 H NMR(400MHz,CDCl3)δ8.21(d,J＝8.0,1H),8.12(s,1H),7.79(d,J＝6.4,2H),7.61(d,J＝6.8,1H),7.51(t,J＝6.8,1H),7.38(d,J＝6.4,2H),7.14-7.21(m,8H),7.09(d,J＝6.8,4H),6.95-7.00(m,6H),1.63(s,6H)。
Example 2
This example provides the use of 5,10- [1,2]]The performance verification of the compound taking the phenazine derivative as the core specifically comprises T 1 Energy level and HOMO, LUMO energy level tests.
T was performed on a portion of the compound provided in example 1 and the existing material, respectively 1 Energy level and HOMO, LUMO energy level measurements, Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO) triplet energy (T) 1 ) For the data obtained by the simulation calculation, the B3LYP hybridization functional was used in the calculation method, the basis set was 6-31G (d, p), and the test results are shown in Table 1.
TABLE 1 results of performance tests on compounds having 5,10- [1,2] phenazine derivatives as core
Compound (I) HOMO(eV) LUMO(eV) T 1 (eV)
Compound 1 -5.344 -0.902 3.186
Compound 2 -5.031 -0.763 2.984
Compound 3 -5.045 -0.927 2.971
Compound 16 -5.127 -0.831 2.942
Compound 30 -4.938 -0.594 2.996
Compound 37 -4.810 -0.689 2.912
Compound 40 -4.936 -0.702 2.963
Compound 41 -5.015 -0.812 2.816
Compound 42 -4.877 -0.894 2.810
Compound 47 -4.861 -0.684 2.953
HT-2 -5.270 -2.091 /
BD01 -4.75 -1.61 2.63
HT-2 and BD01 are conventional materials and have the following structures:
Figure BDA0003732850940000171
as can be seen from Table 1, the compounds provided by the invention, which take 5,10- [1,2] phenazine derivatives as cores, have higher triplet energy and more appropriate HOMO/LUMO, are beneficial to the transport of carriers and the transfer of energy in OLED devices, and can be used as hole transport materials and luminescent materials. Based on the data test results, those skilled in the art can easily understand that the organic electroluminescent device may be a phosphorescent device, a fluorescent device, or a Thermally Activated Delayed Fluorescence (TADF) material device without specific limitation. Based on the data test results, those skilled in the art can easily know that the compound using the 5,10- [1,2] phenazine derivative as the core can effectively improve the luminous efficiency, the service life and other properties of the device after being applied to the OLED device.
Example 3
This example provides an example of a compound with a core of 5,10- [1,2] phenazine derivative, which is used as a light emitting material and/or a hole transporting material applied to an organic electroluminescent device to verify the excellent effects obtained.
The excellent effect of the OLED material applied to the device is detailed through the device performances of the device examples 1-10 and the device comparative examples 1-2. The manufacturing processes of the device examples 1-10 and the device comparative examples 1-2 are the same, the same glass substrate and the same electrode material are adopted, the thickness of the electrode material film is also kept consistent, and the difference is that the material of the second hole transport layer or the main body material in the luminescent layer is adjusted, which is specifically as follows.
Comparative device example 1
Device comparative example 1 provides an organic electroluminescent device, the specific structure of which is shown in fig. 1, comprising a substrate 1, an anode layer 2, a hole injection layer 3, a first hole transport layer 4, a second hole transport layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9 and a cathode layer 10, which are sequentially stacked.
Wherein, the substrate 1 is a glass substrate with the thickness of 0.7mm, the anode layer 2 is made of Indium Tin Oxide (ITO) with high common function, the hole injection layer 3 is made of HAT-CN with the thickness of 5 nm; the material of the first hole transport layer 4(HTL1) is HT-1 and has the thickness of 60 nm; the material of the second hole transport layer 5(HTL2) is HT-2 and has the thickness of 15 nm; the light-emitting layer 6 used BD01 as a light-emitting material and BH1 as a host material, and had a dopant content ratio of 3% and a thickness of 30 nm; HB1 is selected as the material of the hole blocking layer 7(HBL), and the thickness is 10 nm; the material of the electron transport layer 8(ETL) is ET-1, and the thickness is 35 nm; liq is selected as the material of the electron injection layer 9, and the thickness is 2 nm; the cathode layer is made of Al and has a thickness of 100 nm.
The structural formula of the basic material used by each functional layer in the device is as follows:
Figure BDA0003732850940000191
Figure BDA0003732850940000201
the organic electroluminescent device is prepared by the following specific steps:
1) cleaning an ITO anode on a transparent glass substrate, respectively carrying out ultrasonic cleaning for 20 minutes by using deionized water, acetone and ethanol, and then carrying out Plasma (Plasma) treatment for 5 minutes in an oxygen atmosphere;
2) evaporating a hole injection layer material HAT-CN on the ITO anode layer in a vacuum evaporation mode, wherein the thickness of the hole injection layer material HAT-CN is 5nm, and the hole injection layer is used as a hole injection layer;
3) evaporating a hole transport material HT-1 on the hole injection layer in a vacuum evaporation mode, wherein the thickness of the hole transport material HT-1 is 60nm, and the hole transport layer is used as a first hole transport layer;
4) evaporating a hole transport material HT-2 on the first hole transport layer HT-1 in a vacuum evaporation mode, wherein the thickness of the hole transport material HT-2 is 15nm, and the layer serves as a second hole transport layer;
5) co-evaporating a light-emitting layer on the second hole transport layer by a vacuum evaporation method, wherein BD01 is used as a light-emitting material, BH1 is used as a main material, the doping amount ratio is 3%, and the thickness is 30 nm;
6) evaporating a hole blocking material HB1 with the thickness of 10nm on the luminescent layer in a vacuum evaporation mode, wherein the layer is used as a hole blocking layer;
7) evaporating an electron transport material ET-1 on the hole blocking layer in a vacuum evaporation mode, wherein the thickness of the electron transport material ET-1 is 35nm, and the electron transport material ET-1 serves as an electron transport layer;
8) evaporating an electron injection material Liq on the electron transport layer in a vacuum evaporation mode, wherein the thickness of the electron injection material Liq is 2nm, and the electron injection layer is used as an electron injection layer;
9) on the electron injection layer, a cathode Al was deposited by vacuum deposition to a thickness of 100nm, and the layer was used as a cathode conductive electrode.
Comparative device example 2
Same as device comparative example 1, except that: CBP was used as a host material instead of BH1, and GD02 was used as a light-emitting material instead of BD 01.
Device example 1
Same as device comparative example 1, except that: compound 2 was used as the second hole transport layer material in place of HT-2.
Device example 2
Same as device comparative example 1, except that: compound 16 was used as the second hole transport layer material in place of HT-2.
Device example 3
Same as device comparative example 1, except that: compound 27 was used as the second hole transport layer material in place of HT-2.
Device example 4
Same as device comparative example 1, except that: compound 34 was used as the second hole transport layer material in place of HT-2.
Device example 5
Same as device comparative example 1, except that: compound 40 was used as the second hole transport layer material in place of HT-2.
Device example 6
Same as device comparative example 1, except that: compound 41 was used as the second hole transport layer material in place of HT-2.
Device example 7
Same as device comparative example 1, except that: compound 47 was used as the second hole transport layer material in place of HT-2.
Device example 8
Same as device comparative example 2, except that: compound 1 was used as host material instead of CBP.
Device example 9
Same as device comparative example 2, except that: compound 3 was used as host material instead of CBP.
Device example 10
Same as device comparative example 2, except that: compound 36 was used as the host material instead of CBP.
The components of the devices prepared in the device examples 1-10 and the device comparative examples 1-2 are shown in table 2.
TABLE 2 comparison table of components of each organic electroluminescent device
Figure BDA0003732850940000221
Figure BDA0003732850940000231
The cathode and the anode of each group of organic electroluminescent devices were connected by a known driving circuit, and the voltage-efficiency-current density relationship of the OLED devices was measured by a standard method using a Keithley2400 power supply in combination with a PR670 photometer, and the specific test results are shown in table 3.
Table 3, results of testing the performance of each group of organic electroluminescent devices
Figure BDA0003732850940000232
Figure BDA0003732850940000241
As can be seen from Table 3, the compound provided by the invention is applied to an OLED light-emitting device as a light-emitting material and a second hole transport layer material, and has excellent performance. As compound 27 in device example 3 as the second hole layer material compared to HT-2 in device comparative example 1, the device emitted lightThe efficiency is remarkably improved, the luminous efficiency is 8.53cd/A, and the brightness reaches 2369cd/m under the voltage of 6V 2 (ii) a Compared with CBP in comparative example 2, the luminescent efficiency of the device is remarkably improved by taking the compound 3 in the embodiment 9 as the phosphorescent main body material, the luminescent efficiency is 60.63cd/A, and the brightness reaches 6230cd/m at 6V 2 . The compound of the invention is used as a main material or a second hole transport layer material of the OLED device, and compared with the OLED light-emitting device applied by the existing material, the compound has good performances of photoelectric properties such as light-emitting efficiency, brightness and the like, and has great application value and commercial prospect in the application of the OLED device and good industrial prospect.
As described above, the present invention can be preferably implemented, and the above-mentioned embodiments only describe the preferred embodiments of the present invention, and do not limit the scope of the present invention, and various changes and modifications of the technical solution of the present invention made by those skilled in the art without departing from the design spirit of the present invention shall fall within the protection scope defined by the present invention.

Claims (12)

1. A compound taking 5,10- [1,2] phenazine derivative as a core has a structural general formula shown in formula (I):
Figure FDA0003732850930000011
wherein X is a single bond or CR 1 R 2 ，R 1 、R 2 Independently selected from methyl; l is aryl; d is a typical electron donating group;
the typical electron donating group is one selected from the group consisting of a substituted or unsubstituted amine group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted 10H spiro [ acridine-9, 9 '-fluorene ] group, a substituted or unsubstituted 10H spiro [ acridine-9, 9' -xanthene ] group, a substituted or unsubstituted 5-phenyl-5, 10-dihydrophenazinyl group, and a substituted or unsubstituted 10H-phenothiazinyl group.
2. The 5,10- [1,2] phenazine derivative as core compound of claim 1, wherein L is aryl group, and the aryl group is one of phenyl, naphthyl, anthryl and pyrenyl.
3. The compound of claim 1 having a core of 5,10- [1,2] phenazine derivative represented by the general formula (II) or (III):
Figure FDA0003732850930000012
4. a compound having as core a 5,10- [1,2] phenazine derivative according to any one of claims 1 to 3, wherein D is selected from the structures represented by any one of formulae (1) to (7):
Figure FDA0003732850930000021
5. the pharmaceutical composition of claim 4, wherein the compound is 5,10- [1,2]]A compound having a phenazine derivative as a core, wherein Ar is 1 、Ar 2 Is represented by one of phenyl, biphenyl, carbazolyl and furyl; the R is 1 And R 2 Is represented by one of methyl, ethyl, tertiary butyl, phenyl, biphenyl, carbazolyl and furyl.
6. The compound having a core of 5,10- [1,2] phenazine derivative according to claim 1, which has a specific structure described in any one of the following compounds 1 to 18:
Figure FDA0003732850930000022
Figure FDA0003732850930000031
Figure FDA0003732850930000041
7. the compound of claim 1 having a core of 5,10- [1,2] phenazine derivative, which has a specific structure of any one of the following compounds 19 to 41:
Figure FDA0003732850930000042
Figure FDA0003732850930000051
8. the compound of claim 1 having as a core a 5,10- [1,2] phenazine derivative having a specific structure as defined in any one of the following compounds 42 to 47:
Figure FDA0003732850930000061
9. an organic electroluminescent material comprising the compound having a core of a 5,10- [1,2] phenazine derivative according to any one of claims 1 to 8.
10. An organic electroluminescent element comprising an anode and a cathode, and at least a hole transport layer, a light-emitting layer, and an electron transport layer disposed between the anode and the cathode, wherein at least one of the hole transport layer and the light-emitting layer comprises the organic electroluminescent material according to claim 9.
11. The organic electroluminescent element according to claim 10, wherein the light-emitting layer is any one of a phosphorescent device, a fluorescent device, and a thermally activated delayed fluorescent device.
12. Use of the organic electroluminescent material according to claim 9 or the organic electroluminescent element according to claim 10 in an organic electroluminescent display.
CN202210797970.3A 2022-07-06 2022-07-06 Compound with 5,10- [1,2] phenazine derivative as core and application thereof Pending CN114989170A (en)

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Citations (3)

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Publication number Priority date Publication date Assignee Title
WO2019076198A1 (en) * 2017-10-16 2019-04-25 北京鼎材科技有限公司 Compound and organic electroluminescent device
WO2020135686A1 (en) * 2018-12-29 2020-07-02 江苏三月光电科技有限公司 Organic compound with carbazole derivative as core and application thereof to organic electroluminescent device
CN114644637A (en) * 2022-03-26 2022-06-21 西安瑞联新材料股份有限公司 Tris (1, 2-phenyl) diamine derivative organic photoelectric material and its use

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019076198A1 (en) * 2017-10-16 2019-04-25 北京鼎材科技有限公司 Compound and organic electroluminescent device
WO2020135686A1 (en) * 2018-12-29 2020-07-02 江苏三月光电科技有限公司 Organic compound with carbazole derivative as core and application thereof to organic electroluminescent device
CN114644637A (en) * 2022-03-26 2022-06-21 西安瑞联新材料股份有限公司 Tris (1, 2-phenyl) diamine derivative organic photoelectric material and its use

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