A composition and an organic electroluminescent device

By using deuterated biscarbazole or indolocarbazole and triazine host material in the light-emitting layer of the organic electroluminescent device and adding deuterated doping material, the problem of insufficient recombination of electrons and holes is solved, and OLED devices with high efficiency, stability and low power consumption are achieved.

CN119020024BActive Publication Date: 2025-06-10NANJING TOPTO MATERIALS CO LTD
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Patent Information

Application Number
CN202411498618.5
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2024-10-25
Publication Date
2025-06-10
Estimated Expiration
2044-10-25

AI Technical Summary

Technical Problem

In existing organic electroluminescent devices, electrons and holes are not fully recombined in the luminescent layer, resulting in low energy utilization, affecting device performance and lifetime.

Method used

A two-component host material consisting of compound one (deuterated biscarbazole or indolocarbazole) and compound two (triazine-based compound, phenyl-substituted dibenzofuran and carbazole) is used as the luminescent layer, and deuterated compound three is added as the doping material.

Benefits of technology

By optimizing the injection and recombination of electrons and holes, luminescence efficiency and device stability are improved, service life is extended, and power consumption is reduced.

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Abstract

The present invention relates to a composition and an organic electroluminescent device. The present invention provides a composition comprising Compound One, Compound Two, and Compound Three. Compound One is as shown in Formula 1; Compound Two is selected from one of Formula 2-1, Formula 2-2, or Formula 3; Compound Three is selected from one of Formula 4 to Formula 8. The composition of the present invention realizes an OLED device with high performance, high stability, and low power consumption.
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Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescence, and more particularly, to a composition and an organic electroluminescent device. Background Art

[0002] Generally, an organic electroluminescent device has a structure including an anode and a cathode and an organic material layer therebetween. The organic layer is usually formed of a multi-layer structure composed of different materials to improve the efficiency and stability of the organic electronic device, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0003] Research on improving the performance of organic electroluminescent devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, and extending the service life of the device. In order to continuously improve the performance of organic electroluminescent devices, not only continuous research and innovation of organic electro-optical functional materials are required to create higher-performance organic electro-functional materials, but also innovation in the structure and manufacturing process of organic electroluminescent devices, and there is a continuous need to develop new materials for the above-mentioned organic light-emitting devices.

[0004] In an organic electroluminescent device, the organic light-emitting layer is generally prepared by doping a dye with a single host material. The recombination of electrons and holes in the light-emitting layer is insufficient, resulting in reduced energy utilization efficiency and affecting the device performance. Taking a green organic electroluminescent device as an example, its organic light-emitting layer (EML) is usually prepared by doping a dye with a single N-type host material; a single N-type green host material often has a low hole mobility or even a strong hole-blocking effect, so that the recombination of electrons and holes in the organic light-emitting layer is insufficient, the energy utilization efficiency is low, and finally the current efficiency is low and the device life is seriously affected.

[0005] To optimize the device performance, a material with a two-component host can be used as the light-emitting layer. The light-emitting layer with a two-component host usually contains an N-type host material and a P-type host material. The compound disclosed in the patent with the publication number 《CN112225726A》 adopts a triazine host structure, and an N-phenylcarbazolyl group and a deuterated phenyl-substituted dibenzofuran group are arranged on the side chain of the triazine. This compound is used as an N-type green host material, and the P-type green host material paired with it discloses compounds of bis-carbazole and tris-carbazole, but the P-type host materials are not deuterated;

[0006] The P-type host material disclosed in the patent with the publication number 《CN117295715A》 has a bis-carbazole compound and the P-type host material is substituted by deuterium. The N-type host material paired with it adopts a triazine host structure, and the group arranged on the side chain of the triazine is indolocarbazole.

[0007] The patent with the publication number 《CN117377655 A》 also discloses a P-type host material of the deuterated biscarbazole type, but the N-type host material it is paired with also uses a triazine as the main body and is paired with an indolocarbazole group on its side chain.

[0008] The patent with the publication number 《KR20240015487 A》 discloses a P-type host material of the deuterated biscarbazole type, and the N-type host material it is paired with uses a triazine as the main body and has benzothiophene and benzofuran groups arranged on its side chain.

[0009] The patent with the publication number 《CN114599647 A》 discloses a P-type host material of the deuterated biscarbazole type, and the N-type host material it is paired with uses a triazine as the main body and has benzothiophene and / or benzofuran groups arranged on its side chain, and the N-type host material side chain does not carry a carbazole group.

[0010] Based on this research foundation, further research and exploration are needed to develop and combine different organic electroluminescent materials and develop organic electroluminescent devices with excellent luminous efficiency and lifespan. The compounds and organic electroluminescent devices in the present invention can improve the green light luminous efficiency and lifespan and promote the localization of OLED materials. Summary of the Invention

[0011] The present invention provides a composition on the basis of the existing technology, which is at least applied to the light-emitting layer of an organic electroluminescent device. This composition at least contains Compound One, Compound Two, and Compound Three. Compound One is as shown in Formula 1:

[0012] ;

[0013] Wherein: R1-R24 are independently selected from hydrogen, deuterium, phenyl, deuterated phenyl; L is a single bond, phenylene or deuterated phenylene;

[0014] Compound Two is selected from one of Formula 2-1, Formula 2-2 or Formula 3:

[0015] ;

[0016] Wherein: R25-R30 are independently selected from hydrogen, deuterium, phenyl, deuterated phenyl;

[0017] R31-R63 are each independently selected from hydrogen, deuterium;

[0018] R64-R73 are each independently selected from hydrogen, deuterium, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl;

[0019] Compound Three is selected from one of Formula 4 - Formula 8:

[0020] ;

[0021] Wherein: R74 - R86 are each independently selected from hydrogen, deuterium, cyano, substituted or unsubstituted C1 - C10 alkyl, substituted or unsubstituted C6 - C20 aryl, and the substituents are selected from at least one of the following atoms or groups: deuterium, monodeuteriomethyl, dideuteriomethyl, trideuteriomethyl; R87 and R88 are each independently selected from hydrogen or deuterium, and R89 - R92 are each independently selected from hydrogen, deuterium, substituted or unsubstituted C6 - C20 aryl, and two adjacent ones of R89 - R92 can be joined or fused to form a phenyl or naphthyl group.

[0022] As a preferred embodiment of the present invention, Compound I is selected from one of Formula 1 - 1 and 1 - 2: , Wherein R1 - R24 are independently selected from hydrogen, deuterium, phenyl, deuterated phenyl.

[0023] As a preferred embodiment of the present invention, the compound shown in Formula 4 - Formula 6 contains at least one trideuteriomethyl group.

[0024] As a preferred embodiment of the present invention, the deuteration rate of Compound II is 18% - 100%.

[0025] As a preferred embodiment of the present invention, the Compound I is at least one of the compounds of the following structural formulas:

[0026] 。

[0027] As a preferred embodiment of the present invention, the compound two is at least one of the compounds with the following structural formulas:

[0028] 。

[0029] As a preferred embodiment of the present invention, the compound three is at least one of the compounds with the following structural formulas:

[0030] 。

[0031] As a preferred embodiment of the present invention, it includes a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, and the organic layer contains the composition of any one of the above.

[0032] As a preferred embodiment of the present invention, the organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; the light-emitting layer is composed of the composition of any one of the above.

[0033] As a preferred embodiment of the present invention, the hole injection layer contains at least one of the following structural formula compounds:

[0034] 。

[0035] Advantages of the present invention:

[0036] The composition of the present invention consists of Compound One and Compound Two as the light-emitting host material, and Compound Three as the doping material. Among them, Compound One selects a compound with a host structure of bis-carbazole or indolo-carbazole, and deuteration is carried out on the carbazole or indolo-carbazole; Compound Two is a compound with a triazine host, and a phenyl-substituted dibenzofuran and carbazole are provided on its side chain group; at the same time, the doping material selects a deuterated compound. Through such a device combination, the luminous efficiency can be enhanced: the combination of Compound One (deuterated bis-carbazole or indolo-carbazole) and Compound Two helps to achieve the effective transport and balance of electrons and holes, can optimize the injection and recombination of electrons and holes, thereby improving the luminous efficiency. Deuterated Compound Three as the doping material has a higher quantum efficiency and improves the overall luminous efficiency of the device.

[0037] Improving device stability: The application of deuteration technology in Compound I and Compound III improves the thermal and chemical stability of the material, thereby enhancing the device stability and extending the device lifespan.

[0038] Improving color purity and brightness: Through precise molecular design and deuteration technology, the present invention can improve the color purity of the luminescent material and achieve a more pure emission color. The optimized electron and hole recombination process helps to increase the device brightness and improve the display or lighting effect.

[0039] Reducing power consumption: The high luminous efficiency and optimized electron transport contribute to reducing the power consumption of the device during operation and improving the energy efficiency ratio.

[0040] In summary, through the careful design and combination of the host material and dopant, the present invention realizes high-performance, high-stability, and low-power OLED devices, providing new possibilities for the development of display and lighting technologies. Description of the Drawings

[0041] Figure 1 It is a schematic structural diagram of the organic electroluminescent device provided by the present invention;

[0042] The reference numerals in the figure respectively represent: 1 - anode, 2 - hole injection layer, 3 - hole transport layer, 4 - electron blocking layer, 5 - light-emitting layer, 6 - hole blocking layer, 7 - electron transport layer, 8 - electron injection layer, 9 - cathode. Detailed Embodiments

[0043] The following further illustrates and describes the embodiments of various aspects. It should be understood that the description herein is not intended to limit the claims to the specific aspects described. Instead, it is intended to cover alternatives, modifications, and equivalents that may be included within the spirit and scope of the present disclosure as defined by the appended claims.

[0044] As used herein, in "substituted" or "unsubstituted", the term "substituted" means that at least one hydrogen in the group is re-coordinated with deuterium, a hydrocarbon group, a hydrocarbon derivative group, a halogen, or a cyano group (-CN). The term "unsubstituted" means that at least one hydrogen in the group is not re-coordinated with deuterium, a hydrocarbon group, a hydrocarbon derivative group, a halogen, or a cyano group (-CN). Examples of hydrocarbon or hydrocarbon derivative groups may include C1 - C30 alkyl, C2 - C30 alkenyl, C2 - C30 alkynyl, C6 - C30 aryl, C5 - C30 heteroaryl, C1 - C30 alkylamino, C6 - C30 arylamino, C6 - C30 heteroarylamino, C6 - C30 arylheteroarylamino, etc., but are not limited thereto.

[0045] Deuterium in the present invention refers to a stable isotope of hydrogen, also known as heavy hydrogen, with the element symbol D.

[0046] In the present invention, the aryl group refers to a fully carbonaceous monocyclic or fused polycyclic group having 6 to 30 carbon atoms and having a completely conjugated π-electron system. Non-limiting examples of the aryl group include phenyl, naphthyl, anthracenyl, biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, benzophenanthryl, triphenyl[1,12-bcd]furanyl, phenanthryl, etc.

[0047] For those not specified in the examples, the operations were carried out under conventional conditions or conditions recommended by the manufacturer. For those reagents or instruments without indicating the manufacturer, they were all conventional products that could be obtained through commercial purchase.

[0048] Synthesis Example 1:

[0049]

[0050] S1:

[0051] Procedure: Under nitrogen, carbazole-D8 (50 g, 285.4 mmol, 1 eq) and ultra-dry THF (500 ml) were added to a three-necked flask, and the temperature was lowered to below 0 °C. Sodium tert-butoxide (32.9 g, 342.4 mmol, 1.2 eq) was added. After the addition, the mixture was transferred to room temperature and stirred for 2 h. The triazine compound (71 g, 313.9 mmol, 1.1 eq) was dissolved in 500 mL of ultra-dry THF, cooled to below 0 °C, and slowly added dropwise to the above reaction solution. After the addition, the mixture was allowed to warm to room temperature and stirred while monitoring by HPLC.

[0052] Work-up: After the reaction was completed, water was added and the mixture was filtered by suction. The filter cake was purified by recrystallization from toluene to obtain 72.5 g of a white solid, with a yield of 70.4%.

[0053] S2:

[0054] Procedure: Intermediate 1 (44 g, 120.6 mmol, 1.05 eq), a borate compound (42.9 g, 114.9 mmol, 1 eq), potassium carbonate (47.3 g, 344.7 mmol, 3 eq) and THF / water (600 ml + 200 ml) were added to a three-necked flask. Under N2 protection, tetrakis(triphenylphosphine)palladium(0) (2.64 g, 2.3 mmol, 0.02 eq) was added, and the mixture was refluxed and stirred at 85 °C for 8 h.

[0055] Work-up: The reaction was stopped, and the mixture was filtered by suction while it was hot. The filter cake was washed with water and ethanol, dried, and then recrystallized from toluene to obtain 35.4 g (0.0612 mol) of a white solid, with a yield of 50.7% and an HPLC purity of 99.98%.

[0056] Synthesis Example 2:

[0057]

[0058] S1:

[0059] S2:

[0060] Procedure: Add triazine compound (550 g, 1.271 mol, 1 eq), borate compound (525 g, 1.4 mol, 1.1 eq), potassium carbonate (439 g, 3.18 mol, 2.5 eq) and toluene / ethanol / water (8250 ml + 1375 ml + 1375 ml) into a three-necked flask. Under N2 protection, add tetrakis(triphenylphosphine)palladium (29.35 g, 25.4 mmol, 0.02 eq), and heat to reflux with stirring for 8 h.

[0061] Work-up: Stop the reaction, filter while hot, wash the filter cake with water and ethanol, and recrystallize the filter cake 4 times with toluene to obtain approximately 450 g, with a yield of 54.9%.

[0062] Synthesize compounds N-2, N-3, N-10, N-15, N-17, N-26, N-43, N-59 in a similar manner. See Tables 1-1, 1-2, 1-3, 1-4 for details:

[0063] Table 1-1

[0064]

[0065] Table 1-2

[0066]

[0067] Table 1-3

[0068]

[0069] Table 1-4

[0070]

[0071] Synthesis Example 11:

[0072]

[0073] S1:

[0074] Procedure: Under nitrogen protection, add borate (66 g, 0.1758 mol, 1 eq), triazine compound (80 g, 0.3517 mol, 2 eq) into the reaction flask, then add 700 ml of toluene, 100 ml of ethanol, potassium carbonate (29 g, 0.21 mol, 1.2 eq), 100 ml of water, and palladium tetrakis(triphenylphosphine) (2 g, 0.0017 mol, 1% eq). After the addition is complete, heat the reaction solution to reflux for 5 h, and sample for HPLC detection until the reaction is complete.

[0075] Work-up: Add water to the reaction solution, filter by suction, wash the filter cake with water and then with ethanol, and dry under a blast of air to obtain approximately 41 g of the product with a yield of 53%.

[0076] S2:

[0077] Procedure: Under nitrogen protection, add intermediate 1 (41 g, 0.0934 mol, 1 eq), borate compound (36.95 g, 0.098 mol, 1.05 eq) into the reaction flask, then add 600 ml of toluene, 140 ml of ethanol, potassium carbonate (38 g, 0.28 mol, 3 eq), 140 ml of water, and palladium tetrakis(triphenylphosphine) (1.07 g, 0.0009 mol, 1% eq). After the addition is complete, heat the reaction solution to reflux for 6 h, and sample for HPLC detection until the reaction is complete.

[0078] Work-up: After the reaction solution is cooled, filter it, wash the filter cake with water and then with ethanol, and purify it by recrystallization from toluene to obtain approximately 36.8 g (0.0562 mol) of the product with a yield of 60.2%.

[0079] Synthesis Example 12:

[0080]

[0081] S1:

[0082] S2:

[0083] The procedure and work-up are referred to Synthesis Example 11, and approximately 33.4 g of the product is obtained with a yield of 52.7%.

[0084] Synthesis Example 13:

[0085]

[0086] S1:

[0087] Procedure: Under nitrogen protection, add the intermediate bi-carbazole compound (42 g, 0.1 mol, 1 eq), the halide (23.3 g, 0.1 mol, 1 eq) into the reaction flask, then add 400 ml of toluene, sodium tert-butoxide (11.5 g, 0.12 mol, 1.2 eq), Pd2(dba)3 (1.37 g, 0.0015 mol, 1.5% eq), and tbu-xphos (1.27 g, 0.003 mol, 3%). After the addition is complete, heat the reaction solution to reflux overnight, and take a sample for HPLC detection until the reaction is complete.

[0088] Work-up: Cool down the reaction solution and directly filter it through silica gel. Concentrate the filtrate to dryness and recrystallize it with toluene to obtain approximately 24.2 g (0.0421 mol) of the product, with a yield of 42.1%.

[0089] Synthesize compounds P-1, P-8, P-9, P-18, P-19, P-25, and P-49 in a similar manner. See Tables 2-1, 2-2, and 2-3 for details:

[0090] Table 2-1

[0091]

[0092] Table 2-2

[0093]

[0094] Table 2-3

[0095]

[0096] The synthetic identification results of the compounds prepared above are shown in Tables 3-1, 3-2, 3-3, 3-4, and 3-5 as follows:

[0097] Table 3-1

[0098]

[0099] Table 3-2

[0100]

[0101] Table 3-3

[0102]

[0103] Table 3-4

[0104]

[0105] Table 3-5

[0106]

[0107] Device performance test:

[0108] Application Example 1:

[0109] ITO was used as the anode substrate material of the reflective layer, and it was successively treated with water, acetone, and N 2 for its surface treatment;

[0110] Above the ITO anode substrate, 10 nm of HT-1 was deposited. HT-1 contained 3 wt% of PD-25 to form a hole injection layer (HIL);

[0111] Above the hole injection layer (HIL), 100 nm of HT-1 was evaporated to form a hole transport layer (HTL);

[0112] Above the hole transport layer (HTL), the compound GP-2 of the present invention was vacuum-evaporated to form an electron blocking layer (GPL) with a thickness of 30 nm;

[0113] The compound P-11 of the present invention and the compound N-5 were co-evaporated as the light-emitting host material in a mass ratio of 6:4, and GD-29 was used as the doping material (the dosage of GD-29 was 8% of the total weight of the compounds P-11 and N-5) and evaporated on the electron blocking layer (GPL) to form a light-emitting layer with a thickness of 30 nm;

[0114] NB-1 was evaporated onto the light-emitting layer to obtain a hole blocking layer (HBL) with a thickness of 20 nm;

[0115] ET-1 and LiQ were co-evaporated onto the hole blocking layer (HBL) in a mass ratio of 5:5 to obtain an electron transport layer (ETL) with a thickness of 50 nm;

[0116] Magnesium (Mg) and silver (Ag) were mixed and evaporated in a mass ratio of 9:1 above the electron transport layer (ETL) to form an electron injection layer (EIL) with a thickness of 50 nm;

[0117] Thereafter, silver (Ag) was evaporated above the electron injection layer to form a cathode with a thickness of 100 nm. On the above cathode sealing layer, 50 nm of DNTPD was deposited. In addition, the cathode surface was sealed with a UV-curing adhesive and a packaging film (seal cap) containing a dehumidifying agent to protect the organic electroluminescent device from being affected by oxygen or moisture in the atmosphere. Thus, the organic electroluminescent device was prepared.

[0118]

[0119]

[0120] Application Example 2 - 19

[0121] Replace the compound N - 5 in Application Example 1 with the compounds N - 7, N - 2, N - 3, and N - 10 of the present invention respectively, and keep the other parts the same as those in Application Example 1. Based on this, Application Examples 2 - 5 are prepared;

[0122] Replace the compound N - 5 in Application Example 1 with the compounds N - 15, N - 17, N - 26, N - 43, and N - 59 of the present invention respectively, and replace the compound GD - 29 in Application Example 1 with the compound GD - 22 of the present invention. Keep the other parts the same as those in Application Example 1. Based on this, Application Examples 6 - 10 are prepared;

[0123] Replace the compound N - 5 in Application Example 1 with the compounds N - 87 and N - 86 of the present invention respectively, and replace the compound PD - 25 in Application Example 1 with the compound PD - 9 of the present invention. Keep the other parts the same as those in Application Example 1. Based on this, Application Examples 11 - 12 are prepared;

[0124] Replace the compound P - 11 in Application Example 1 with the compounds P - 1 and P - 8 of the present invention respectively, and replace the compound PD - 25 in Application Example 1 with the compound PD - 9 of the present invention. Keep the other parts the same as those in Application Example 1. Based on this, organic electroluminescent devices of Application Examples 13 - 14 are prepared;

[0125] Replace the compound P - 11 in Application Example 1 with the compounds P - 9, P - 18, P - 19, P - 25, and P - 49 of the present invention respectively, replace the compound PD - 25 in Application Example 1 with the compound PD - 9 of the present invention, and replace the compound GD - 29 in Application Example 1 with the compound GD - 38 of the present invention. Keep the other parts the same as those in Application Example 1. Based on this, organic electroluminescent devices of Application Examples 15 - 19 are prepared.

[0126] Comparative Example 1 - 3

[0127] Use HAT - CN, 1, G1, and GD1 used in the examples of CN112225726A to replace the corresponding layers in Application Example 1 to prepare Comparative Example 1; use PD - 25, 1, G1, and GD - 29 to replace the corresponding layers in Application Example 1 to prepare Comparative Example 2; use HAT - CN, 1 - 2a, 2 - 22, and Ir(ppy)3 used in the examples of CN117295715A to replace the corresponding layers in Application Example 1 to prepare Comparative Example 3; use PD - 25, 1 - 2a, 2 - 22, and GD - 29 to replace the corresponding layers in Application Example 1 to prepare Comparative Example 4.

[0128] The organic electroluminescent devices prepared in Application Examples 1-19 and Comparative Examples 1-4 were tested separately. The organic electroluminescent devices prepared in Comparative Examples 1-4 and Application Examples 1-19 were tested for voltage, luminous efficiency, lifespan, and luminous lifespan. The luminous lifespan test obtained the luminous lifespan T97% data (the time when the luminous brightness decreased to 97% of the initial brightness). The test equipment was the TEO luminous device lifespan test system. The test results are shown in Table 4 below.

[0129] Table 4

[0130] Experimental group Hole injection layer N-type host P-type host GD Voltage (V) Luminous efficiency (Cd / A) Lifetime Emission color Control Example 1 HAT-CN 1 G1 GD1 3.68 142.6 100% Green Control Example 2 PD-25 1 G1 GD-29 3.57 136.7 98% Green Control Example 3 HAT-CN 1-2a 2-22 Ir(ppy)3 4.7 118.4 92% Green Control Example 4 PD-25 1-2a 2-22 GD-29 3.94 125.9 94% Green Application Example 1 PD-25 N-5 P-11 GD-29 3.18 204.3 150% Green Application Example 2 PD-25 N-7 P-11 GD-29 3.25 198.7 135% Green Application Example 3 PD-25 N-2 P-11 GD-29 3.30 199.4 133% Green Application Example 4 PD-25 N-3 P-11 GD-29 3.20 205.8 149% Green Application Example 5 PD-25 N-10 P-11 GD-29 3.19 203.9 148% Green Application Example 6 PD-25 N-15 P-11 GD-22 3.20 202.7 147% Green Application Example 7 PD-25 N-17 P-11 GD-22 3.28 197.4 138% Green Application Example 8 PD-25 N-26 P-11 GD-22 3.29 196.2 139% Green Application Example 9 PD-25 N-43 P-11 GD-22 3.32 195.6 137% Green Application Example 10 PD-25 N-59 P-11 GD-22 3.33 194.1 136% Green Application Example 11 PD-9 N-87 P-11 GD-29 3.34 195.3 134% Green Application Example 12 PD-9 N-86 P-11 GD-29 3.35 196.4 140% Green Application Example 13 PD-9 N-5 P-1 GD-29 3.22 201.5 144% Green Application Example 14 PD-9 N-5 P-8 GD-29 3.24 200.6 145% Green Application Example 15 PD-9 N-5 P-9 GD-38 3.36 195.2 141% Green Application Example 16 PD-9 N-5 P-18 GD-38 3.23 199.4 143% Green Application Example 17 PD-9 N-5 P-19 GD-38 3.37 196.8 142% Green Application Example 18 PD-9 N-5 P-25 GD-38 3.38 197.7 132% Green Application Example 19 PD-9 N-5 P-49 GD-38 3.45 194.1 131% Green

[0131] As can be seen from Table 4 above, the composition of the present invention consists of Compound 1 and Compound 2 as the light-emitting host material, and Compound 3 as the dopant. Among them, Compound 1 is a compound with a host structure of biscarbazole or indolocarbazole, and deuteration is carried out on the carbazole or indolocarbazole; Compound 2 is a compound with a triazine host, and phenyl-substituted dibenzofuran and carbazole are provided on its side chain groups; at the same time, the dopant is a deuterated compound, which is used in the organic electroluminescent device as the light-emitting host material, realizing high-performance, high-stability, and low-power OLED devices, providing new possibilities for the development of display and lighting technologies.

Claims

1. A composition, characterized in that At least comprising compound 1, compound 2, and compound 3, wherein compound 1 is as shown in formula 1-1: ; Wherein: R1-R24 are independently selected from hydrogen, deuterium, phenyl, deuterated phenyl; Compound 2 is selected from Formula 2-1: ; Wherein: R25-R34 are independently selected from hydrogen, deuterium, phenyl, deuterated phenyl; Compound 3 is selected from one of Formula 4 to Formula 7 ; Wherein: R74-R86 are each independently selected from hydrogen, deuterium, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C20 aryl, and the substituent is selected from at least one of the following atoms or groups: deuterium, monodeuteriomethyl, dideuteriomethyl, trideuteriomethyl; R87 and R88 are each independently selected from hydrogen or deuterium.

2. A composition according to claim 1, characterized in that The compounds shown in Formulae 4 to 6 contain at least one trideuterated methyl group.

3. A composition according to claim 1, characterized in that The deuterium substitution rate of compound 2 is 18%-100%.

4. A composition according to claim 1, characterized in that The compound 1 is at least one of the following compounds: 。 5. A composition according to claim 1, characterized in that The second compound is at least one of the following compounds: 。 6. A composition according to claim 1, characterized in that The compound three is at least one of the following structural compounds: 。 7. An organic electroluminescent device, characterized in that: The method comprises a first electrode, a second electrode and an organic layer formed between the first electrode and the second electrode, wherein the organic layer contains the composition according to any one of claims 1 to 6.

8. An organic electroluminescent device as claimed in claim 7, characterized in that: The organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; and the light-emitting layer is composed of the composition according to any one of claims 1 to 6.

9. An organic electroluminescent device as claimed in claim 8, characterized in that: The hole injection layer contains at least one of the following compounds: 。

Citation Information

Patent Citations

  • Compound and organic electroluminescent device

    CN112225726A

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    CN114599647A

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    CN117295715A

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    CN117377655A

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    CN117800897A