A light-emitting auxiliary material and preparation method thereof and organic electroluminescent device

Abstract

The invention relates to a luminescent auxiliary material and a preparation method thereof and an organic electroluminescent device, belonging to the field of organic photoelectric luminescent materials. The general structural formula of the luminescent auxiliary material is: the invention uses a seven-membered nitrogen-containing heterocycle as a parent core and connects it with an aromatic amine group. The obtained compound can be used in green and red organic electroluminescent devices. The prepared device has the characteristics of high luminescent efficiency, low driving voltage and long service life.

Description

Technical Field

[0001] The invention relates to the technical field of organic photoelectric luminescent materials, in particular to a luminescent auxiliary material and a preparation method thereof and an organic electroluminescent device. Background Art

[0002] With the rapid development of information technology, people have put forward new goals and requirements for the performance of information display systems. Organic electroluminescent devices (OLEDs) have become a research hotspot with high brightness, high resolution, wide viewing angle and low energy consumption. They can meet the above needs of people, and at the same time have other advantages such as wide operating temperature and flexible display, becoming the new favorite of the new generation of flat panel displays.

[0003] An organic light-emitting diode generally has the following structure: an anode, a cathode, and an organic material layer between the two. In order to improve the efficiency and stability of organic EL elements, the organic material layer includes multiple layers with different materials, such as a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer (ETL), and an electron injection layer (EIL). Among them, layers with the function of transporting holes, such as a hole injection layer, a hole transport layer, an electron blocking layer, etc., can change the hole transfer efficiency, luminous efficiency, life, etc. from holes to the light-emitting layer, and have a huge impact on the performance data of electronic devices.

[0004] Usually, a luminescent auxiliary layer is added between the hole transport layer and the light-emitting layer (i.e., a multi-layer hole transport layer is provided) to improve the life and efficiency of the device. The luminescent auxiliary layer can reduce the potential barrier between the hole transport layer and the light-emitting layer, reduce the driving voltage of the organic electroluminescent device, and further increase the utilization rate of holes, thereby improving the luminous efficiency and life of the device and reducing the driving voltage. However, there are few functional materials that can form luminescent auxiliary layers, especially the life and luminous efficiency of OLEDs are not significantly improved, and the glass transition temperature is low. Therefore, it is particularly important to develop higher performance organic functional materials to meet the requirements of panel manufacturers. Summary of the invention

[0005] The object of the present invention is to provide a luminescence auxiliary material and a preparation method thereof and an organic electroluminescent device to solve the problems raised in the above background technology.

[0006] To achieve the above object, the present invention provides the following technical solutions:

[0007] A luminescence auxiliary material, the general structural formula of the luminescence auxiliary material is Formula I:

[0008]

[0009] Wherein, X is O, S, -CR4R5-, -NR6;

[0010] R1-R3 are each independently hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C18 aryl, or substituted or unsubstituted 3-30 membered heteroaryl;

[0011] R4 and R5 are each independently a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted C6-C24 aryl group, or a substituted or unsubstituted 3-30-membered heteroaryl group;

[0012] L 1 is at least one of a connecting bond, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted 3-20-membered heteroaryl group, a substituted or unsubstituted C10-C30 condensed ring group, and a substituted or unsubstituted C5-C30 spirocyclic group;

[0013] R6, Ar1, Ar2 represent at least one of substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted 3-30 membered heterocycloalkyl; substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-20 membered heteroaryl; substituted or unsubstituted C10-C30 condensed ring group, substituted or unsubstituted C5-C30 spirocyclic group.

[0014] As a further technical solution of the present invention, the heteroatom in the 3-membered to 30-membered heterocycloalkyl is at least one of N, O, S, Si, P, and Se; the heteroatom in the substituted or unsubstituted 3-membered to 20-membered heteroaryl is at least one of N, O, S, Si, P, and Se.

[0015] As a further technical solution of the present invention, R1-R3 are each independently hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, alkoxy, phenyl, methylbenzene, biphenyl, naphthyl, terphenyl, butyl, pentyl, hexyl, dibenzofuranyl, dibenzothienyl, phenanthrenyl, carbazolyl, pyridyl; R1-R3 are each substituted at any position on the benzene ring, and the number of substitutions is 0-4.

[0016] As a further technical solution of the present invention, Ar1 and Ar2 are connected to N at any connectable position, and Ar1 and Ar2 are each independently at least one of the following groups:

[0017]

[0018] As a further technical solution of the present invention, the general formula I is one of the following general formulas Ia to If:

[0019]

[0020]

[0021] Among them, L 1 One of the following groups:

[0022]

[0023] As a further technical solution of the present invention, the general formula Ia is one of the following general formulas Ia-1 to Ia-4; the general formula If is one of the following general formulas If-1 to If-4:

[0024]

[0025]

[0026] As a further technical solution of the present invention, R 4 -R 6 Each is independently methyl, ethyl, phenyl, biphenyl, methylbenzene, naphthyl or terphenyl.

[0027] As a further technical solution of the present invention, the L 1 It is at least one of phenyl, naphthyl, biphenyl, terphenyl and phenanthryl.

[0028] A method for preparing a luminescent auxiliary material, the synthetic route of the preparation method is as follows:

[0029]

[0030] When L 1 When it is a non-chemical bond, the method comprises the following steps: under N2 protection, reactant AI, reactant BI, tetrakis(triphenylphosphine)palladium and potassium carbonate are added to a mixed solvent consisting of toluene, ethanol and water respectively, after heating for reaction, cooling to room temperature, after solid precipitation is completed, filtering and washing with water to remove salt, then rinsing with a small amount of ethanol, and drying the filter cake; placing in 1,4-dioxane for recrystallization to obtain a luminescent auxiliary material;

[0031] When L 1When it is a chemical bond, the method comprises the following steps: adding reactant AI and reactant B-II to a reaction container and dissolving them in toluene, then adding Pd2(dba)3, P(t-Bu)3, and t-BuONa under a nitrogen atmosphere; after the addition, slowly raising the reaction temperature and stirring; using diatomaceous earth to filter while hot to remove salt and catalyst, cooling the filtrate to room temperature, then adding distilled water to the filtrate for washing, retaining the organic phase after separation, and extracting the aqueous phase with ethyl acetate; then drying the combined organic layer with magnesium sulfate, and removing the solvent with a rotary evaporator to obtain a luminescent auxiliary material, and the synthesis route thereof is as follows:

[0032]

[0033] Compared with the prior art, the beneficial effects of the present invention are: a seven-membered nitrogen-containing heterocyclic ring is used as a parent core to connect with an aromatic amine group, and the obtained compound can be used in organic electroluminescent devices that emit green light and red light at the same time. The prepared device has the characteristics of high luminous efficiency, low driving voltage and long service life. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] Figure 1 This is the hydrogen nuclear magnetic resonance spectrum of the luminescence auxiliary material prepared in Example 1;

[0035] Figure 2 This is the hydrogen nuclear magnetic resonance spectrum of the luminescence auxiliary material prepared in Example 2;

[0036] Figure 3 This is the nuclear magnetic resonance hydrogen spectrum of the luminescence auxiliary material prepared in Example 3. DETAILED DESCRIPTION

[0037] A luminescent auxiliary material, the general structural formula of which is as follows:

[0038]

[0039] Where X is O, S, -CR 4 R 5 -,-NR 6 ;

[0040] R 1 -R 3 Each is independently hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C18 aryl, or substituted or unsubstituted 3-30-membered heteroaryl;

[0041] R 4 , R 5 Each is independently a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted C6-C24 aryl group, or a substituted or unsubstituted 3-30-membered heteroaryl group;

[0042] L 1 is at least one of a connecting bond, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted 3-20-membered heteroaryl group, a substituted or unsubstituted C10-C30 condensed ring group, and a substituted or unsubstituted C5-C30 spirocyclic group;

[0043] R 6 ,Ar 1 ,Ar 2 It represents at least one of a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted 3-30-membered heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted 3-20-membered heteroaryl group, a substituted or unsubstituted C10-C30 condensed ring group, and a substituted or unsubstituted C5-C30 spirocyclic group.

[0044] Preferably, the luminescent auxiliary material is any one of the following structural formulas 1-179:

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052] Example 1

[0053] A method for preparing a luminescent auxiliary material, the synthetic route of the preparation method is as follows:

[0054]

[0055] Among them, the CAS of reactant A-24 is: 2493275-15-1.

[0056] The preparation method is as follows: after reactant A-24 (30 mmol) and reactant B-24 (36 mmol) are added to a reaction vessel and dissolved in toluene, Pd2(dba)3 (0.3 mmol), P(t-Bu)3 (0.6 mmol), and t-BuONa (60 mmol) are added under a nitrogen atmosphere; after addition, the reaction temperature is slowly raised to 105°C, and the mixture is stirred for 8 hours; diatomaceous earth is used for hot filtration to remove salt and catalyst, and the filtrate is cooled to room temperature, and then distilled water is added to the filtrate for washing, and the organic phase is retained after separation, and the aqueous phase is extracted with ethyl acetate; the combined organic layer is then dried with magnesium sulfate, and the solvent is removed using a rotary evaporator; the remaining substance is purified by column chromatography using dichloromethane: petroleum ether in a volume ratio of 1:(1-9) as an eluent to obtain compound 24 (18.7 g, yield: 87%).

[0057] Compound 24 was characterized, and the characterization results are as follows:

[0058] HPLC purity: >99.7%;

[0059] Mass spectrometry test: theoretical value is 718.94; test value is Ms:718.61;

[0060] Elemental Analysis:

[0061] Theoretical values: C, 90.21; H, 5.89; N, 3.90;

[0062] Test values: C, 90.03; H, 6.05; N, 4.02;

[0063] Please see the attached H NMR spectrum Figure 1 .

[0064] Example 2

[0065] A method for preparing a luminescent auxiliary material, the synthetic route of the preparation method is as follows:

[0066]

[0067] Among them, the CAS of reactant A-132 is 2493275-15-1 (the same as reactant A-24).

[0068] The preparation method is as follows: 2Under protection, reactant A-132 (30 mmol), reactant B-132 (36 mmol), tetrakis(triphenylphosphine)palladium (0.45 mmol) and potassium carbonate (66 mmol) were respectively added to a mixed solvent of toluene, ethanol and water (300 ml: 100 ml: 100 ml), heated to 110 ° C, and reacted for 8 hours. After the reaction was completed, it was cooled to room temperature. After the solid was precipitated, it was filtered and washed with water to remove the salt, and then rinsed with a small amount of ethanol, and the filter cake was dried; it was placed in 1,4-dioxane for recrystallization to obtain compound 132 (20.4 g, yield: 90%).

[0069] Compound 132 was characterized, and the characterization results are as follows:

[0070] HPLC purity: >99.8%;

[0071] Mass spectrometry test: theoretical value is 754.98; test value is Ms:754.72;

[0072] Elemental Analysis:

[0073] Theoretical values: C, 90.68; H, 5.61; N, 3.71;

[0074] Test values: C, 90.38; H, 5.88; N, 3.82;

[0075] For H NMR spectra, please see Figure 2 .

[0076] Example 3

[0077] A method for preparing a luminescent auxiliary material, the synthetic route of the preparation method is as follows:

[0078]

[0079] Among them, the CAS of reactant A-150 is: 2493274-82-9.

[0080] The preparation method is as follows: 2 Under protection, reactant A-150 (30mmol), reactant B-150 (45mmol), tetrakistriphenylphosphine palladium (0.3mmol) and potassium carbonate (63mmol) were respectively added to a mixed solvent of toluene, ethanol and water (400ml:100ml:100ml), heated to 115°C, reacted for 8h, after the reaction was completed, cooled to room temperature, after the solid was precipitated, filtered and washed with water to remove the salt, then rinsed with a small amount of ethanol, and the filter cake was dried; it was placed in 1,4-dioxane for recrystallization to obtain compound 150 (20.7g, yield: 80%, Ms: 861.27).

[0081] Compound 150 was characterized, and the characterization results are as follows:

[0082] HPLC purity: >99.6%;

[0083] Mass spectrometry test: theoretical value is 861.12; test value is Ms:861.27;

[0084] Elemental Analysis:

[0085] Theoretical values: C, 87.87; H, 5.15; N, 3.25; S, 3.72;

[0086] Test values: C, 87.67; H, 5.34; N, 3.30; S, 3.81;

[0087] For H NMR spectra, please see Figure 3 .

[0088] Example 4-Example 24

[0089] The synthesis of compounds 7, 12, 16, 18, 22, 24, 28, 36, 43, 55, 66, 70, 83, 99, 114, 124, 125, 140, 157, 164 and 174 was completed by referring to the synthesis methods of Examples 1 to 3; the mass spectra, molecular formulas and yields are shown in Table 1 below.

[0090] Table 1

[0091] Example Compound Molecular formula Mass spectrometry theoretical value Mass spectrometry test value Yield % Example 4 7 <![CDATA[C 58 H 44 N 2 ]]> 769.00 769.23 88 Example 5 12 <![CDATA[C 60 H 46 N 2 ]]> 795.04 795.30 81 Example 6 16 <![CDATA[C 60 H 45 N 3 ]]> 808.04 808.28 75 Example 7 18 <![CDATA[C 55 H 38 N 2 O]]> 742.92 743.11 85 Example 8 22 <![CDATA[C 56 H 42 N 2 ]]> 742.97 742.75 87 Example 9 24 <![CDATA[C 54 H 42 N 2 ]]> 718.94 718.80 90 Example 10 28 <![CDATA[C 53 H 38 N 2 ]]> 702.90 702.58 86 Embodiment 11 36 <![CDATA[C 57 H 42 N 2 ]]> 754.98 754.77 88 Example 12 43 <![CDATA[C 69 H 49 N 3 ]]> 920.17 920.44 72 Embodiment 13 55 <![CDATA[C 49 H 34 N 2 S]]> 682.89 683.09 83 Embodiment 14 66 <![CDATA[C 56 H 34 N 2 O 2 ]]> 766.90 766.71 78 Embodiment 15 70 <![CDATA[C 63 H 43 N 3 O]]> 858.06 858.24 82 Example 16 83 <![CDATA[C 56 H 36 N 2 O]]> 752.92 752.84 85 Embodiment 17 99 <![CDATA[C 54 H 35 N 3 O]]> 741.89 741.66 83 Embodiment 18 114 <![CDATA[C 63 H 45 N 3 ]]> 844.07 844.07 87 Embodiment 19 124 <![CDATA[C 66 H 48 N 2 ]]> 869.12 869.34 75 Embodiment 20 125 <![CDATA[C 57 H 42 N 2 ]]> 754.98 755.31 86 Embodiment 21 140 <![CDATA[C 66 H 49 N 3 ]]> 884.14 884.41 74 Embodiment 22 157 <![CDATA[C 61 H 41 N 3 O]]> 832.02 832.17 80 Embodiment 23 164 <![CDATA[C 63 H 45 N 3 ]]> 844.07 844.31 81 Embodiment 24 174 <![CDATA[C 55 H 40 N 2 ]]> 728.94 729.10 72

[0092] In addition, it should be noted that other compounds of the present application can be obtained by referring to the synthesis methods of the embodiments listed above, so they are not listed one by one here.

[0093] Application Example 1

[0094] A method for preparing a red light organic electroluminescent device comprises the following steps:

[0095] a. ITO anode: wash the ITO (indium tin oxide)-Ag-ITO (indium tin oxide) glass substrate with a coating thickness of 150nm in distilled water twice, ultrasonically wash for 30 minutes, and then repeatedly wash it with distilled water twice, ultrasonically wash for 10 minutes. After washing, transfer it to a spin dryer for drying, and finally bake it in a vacuum oven at 220°C for 2 hours. After baking, cool it down and it can be used; use the substrate as the anode, use an evaporation machine to carry out the evaporation device process, and evaporate other functional layers thereon in sequence;

[0096] b. HIL (hole injection layer): The hole injection layer materials HT and P-dopant are vacuum evaporated at a deposition rate of 97:3, and the thickness is 10 nm.

[0097] c. HTL (hole transport layer): At a deposition rate of 100%, 125 nm of HT was vacuum-deposited on the hole injection layer as a hole transport layer.

[0098] d. Light-emitting auxiliary layer: The compound provided in the above embodiment 1 is vacuum-deposited on the hole transport layer at a deposition rate of 100 nm as a light-emitting auxiliary layer;

[0099] e. EML (light-emitting layer): Then on the above-mentioned light-emitting auxiliary layer, The evaporation rate of the host material (Host) and the dopant material (Dopant) with a thickness of 40nm are vacuum evaporated as the light-emitting layer. The chemical formulas of the Host and Dopant are as follows; the evaporation rate ratio of the Host and Dopant is 97:3;

[0100] f. HB (hole blocking layer): The evaporation rate is 5.0 nm, and the hole blocking layer is vacuum-deposited with a thickness of 5.0 nm;

[0101] g. ETL (Electron Transport Layer): ET and Liq were vacuum-deposited at a deposition rate of 30 nm as an electron transport layer, and the chemical formula of ET is shown below; wherein the deposition rate ratio of ET to Liq is 50:50;

[0102] h. EIL (electron injection layer): The evaporation rate is 1.0 nm, and a Yb film layer is evaporated to form an electron injection layer;

[0103] i. Cathode: 18 nm of magnesium and silver were evaporated at a deposition rate ratio of 1:9 to form a cathode;

[0104] j. Light extraction layer: At a deposition rate of , CPL with a thickness of 70 nm was vacuum-deposited on the cathode as a light extraction layer;

[0105] k. Package the substrate after evaporation. First, use the glue coating equipment to coat the cleaned cover with UV glue, then move the coated cover to the pressing section, place the evaporation-deposited substrate on the upper end of the cover, and finally bond the substrate and cover with the bonding equipment, and complete the light curing of the UV glue.

[0106] The structure of the prepared red light organic electroluminescent device and the raw materials used in the preparation are as follows:

[0107] ITO / Ag / ITO / HT:P-dopant(10nm) / HT(125nm) / Compound 1(100nm) / Host-R:Dopant-R(40nm) / HB(5nm) / ET:Liq(30nm) / Yb(1nm) / Mg:Ag(18nm) / CPL(70nm);

[0108]

[0109] Application Example 2-117

[0110] The organic electroluminescent devices of Application Examples 2-117 were prepared according to the above-mentioned method for preparing a red organic electroluminescent device, except that the compound 1 in Application Example 1 was replaced by a corresponding compound to form a light-emitting auxiliary layer.

[0111] Comparative Examples 1-8

[0112] An organic electroluminescent device was prepared according to the preparation method of the red organic electroluminescent device in Application Example 1, except that the compound 1 in Application Example 1 was replaced by comparative compound 1-8, wherein the structural formula of comparative compound 1-8 is as follows:

[0113]

[0114] The driving voltage, luminous efficiency, and lifespan of the organic electroluminescent devices obtained in the above Examples 1-117 and Comparative Examples 1-8 were characterized at a brightness of 6000 (nits). The test results are shown in Table 2 below:

[0115] Table 2 Luminous characteristics test results (brightness value is 6000nits)

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123] It can be seen from Table 2 that, compared with the existing organic electroluminescent devices provided by comparative examples 1-8, the organic electroluminescent devices prepared by application examples 1-117 using the luminescent auxiliary materials provided by the present invention have improved driving voltage, luminous efficiency and lifespan.

[0124] Application Example 118

[0125] A method for preparing a green organic electroluminescent device comprises the following steps:

[0126] a. ITO anode: wash the ITO (indium tin oxide)-Ag-ITO (indium tin oxide) glass substrate with a coating thickness of 150nm in distilled water twice, ultrasonically wash for 30 minutes, and then repeatedly wash it with distilled water twice, ultrasonically wash for 10 minutes. After washing, transfer it to a spin dryer for drying, and finally bake it in a vacuum oven at 220°C for 2 hours. After baking, cool it down and it can be used; use the substrate as the anode, use an evaporation machine to carry out the evaporation device process, and evaporate other functional layers thereon in sequence;

[0127] b. HIL (hole injection layer): The hole injection layer materials HT and P-dopant are vacuum evaporated at a deposition rate of 97:3, and the thickness is 10 nm.

[0128] c. HTL (hole transport layer): At a deposition rate of 100%, 120 nm of HT was vacuum-deposited on the hole injection layer as a hole transport layer.

[0129] d. Light-emitting auxiliary layer: At a deposition rate of , 45 nm of the compound 1 provided in the above embodiment is vacuum-deposited on the hole transport layer as a light-emitting auxiliary layer;

[0130] e. EML (light-emitting layer): Then on the above-mentioned light-emitting auxiliary layer, The evaporation rate of the main material (Host-G1 and Host-G2) and the dopant material (Dopant) with a thickness of 400nm are vacuum evaporated as the light-emitting layer, wherein Host-G1 and Host-G2 are co-evaporated as dual main materials with the dopant material, and the ratio of Host-G1 to Host-G2 is 50%:50%. The chemical formulas of Host-G1, Host-G2 and Dopant are shown below; wherein the evaporation rate ratio of the main material to the Dopant is 88:12;

[0131] f. HB (hole blocking layer): The evaporation rate is 5.0 nm, and the hole blocking layer is vacuum-deposited with a thickness of 5.0 nm;

[0132] g. ETL (Electron Transport Layer): ET and Liq were vacuum-deposited at a deposition rate of 30 nm as an electron transport layer, and the chemical formula of ET is shown below; wherein the deposition rate ratio of ET to Liq is 50:50;

[0133] h. EIL (electron injection layer): The evaporation rate is 1.0 nm, and a Yb film layer is evaporated to form an electron injection layer;

[0134] i. Cathode: 18 nm of magnesium and silver were evaporated at a deposition rate ratio of 1:9 to form a cathode;

[0135] j. Light extraction layer: At a deposition rate of , CPL with a thickness of 70 nm was vacuum-deposited on the cathode as a light extraction layer;

[0136] k. Package the substrate after evaporation. First, use the glue coating equipment to coat the cleaned cover with UV glue, then move the coated cover to the pressing section, place the evaporation-deposited substrate on the upper end of the cover, and finally bond the substrate and cover with the bonding equipment, and complete the light curing of the UV glue.

[0137] The structure of the prepared green light organic electroluminescent device and the raw materials used in the preparation are as follows:

[0138] ITO / Ag / ITO / HT:P-dopant(10nm) / HT(120nm) / Compound 1(45nm) / (Host-G1+Host-G2):Dopant-G(400nm) / HB(5nm) / ET:Liq(30nm) / Yb(1nm) / Mg:Ag(18nm) / CPL(70nm);

[0139]

[0140]

[0141] Application Examples 119-165

[0142] The organic electroluminescent devices of Application Examples 119-165 are prepared according to the above-mentioned method for preparing a green organic electroluminescent device, except that the compound 1 in Application Example 118 is replaced by corresponding compounds to form a light-emitting auxiliary layer.

[0143] Comparative Examples 9-16

[0144] An organic electroluminescent device is prepared according to the preparation method of the green organic electroluminescent device in the above-mentioned Application Example 118, except that the compound 1 in Application Example 118 is replaced by a comparative compound 1-8, wherein the structural formula of the comparative compound 1-8 is shown in Comparative Example 1-8.

[0145] The driving voltage, luminous efficiency and life of the organic electroluminescent devices obtained from the device application examples 118-165 and the device comparative examples 9-16 were characterized at a brightness of 15000 (nits). The test results are shown in Table 3 below:

[0146] Table 3 Luminous characteristics test results (brightness value is 15000nits)

[0147]

[0148]

[0149]

[0150]

[0151] It can be seen from Table 3 that, compared with the existing organic electroluminescent devices provided by comparative examples 9-16, the organic electroluminescent devices prepared by application examples 118-165 using the luminescent auxiliary materials provided by the present invention have improved driving voltage, luminous efficiency and lifespan.

[0152] For red light devices, the top-emitting device system provided by the present invention can generally improve the efficiency by 4-6%, and some can even reach 7%. For this device combination, a significant improvement has been achieved.

[0153] For green light devices, the top-emitting device system provided by the present invention can generally improve the efficiency by 4-7%, which has achieved a significant improvement for the combination of this device.

[0154] It will be apparent to those skilled in the art that the invention is not limited to the details of the exemplary embodiments described above and that the invention can be implemented in other specific forms without departing from the spirit or essential features of the invention. Therefore, the embodiments should be considered exemplary and non-limiting in all respects, and the scope of the invention is defined by the appended claims rather than the foregoing description, and it is intended that all variations falling within the meaning and scope of the equivalent elements of the claims be included in the invention. Any reference numeral in a claim should not be considered as limiting the claim to which it relates.

[0155] In addition, it should be understood that although the present specification is described according to implementation modes, not every implementation mode contains only one independent technical solution. This description of the specification is only for the sake of clarity. Those skilled in the art should regard the specification as a whole. The technical solutions in each embodiment may also be appropriately combined to form other implementation modes that can be understood by those skilled in the art.

Claims

1. A luminous auxiliary material, It is characterized in that The general structural formula of the luminescent auxiliary material is general formula I: Wherein, X is independently O, S, -CR 4 R 5 -; R 1 -R 3 Each is independently hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, phenyl, methylbenzene, biphenyl, naphthyl; R 1 -R 3 Each is substituted at any position on the benzene ring, and the number of substitutions is 0-4; R 4 -R 5 Each is independently methyl, ethyl, phenyl, biphenyl, methylbenzene, or naphthyl; L 1 are independently a linking bond, a phenyl group, or a naphthyl group; Ar 1 ,Ar 2 Connect with N at any connectable position, Ar 1 ,Ar 2 Each independently is at least one of the following groups:

2. The luminescence auxiliary material according to claim 1, It is characterized in that The general formula I is one of the following general formulas Id to If:

3. The luminescence auxiliary material according to claim 2, It is characterized in that The general formula I is one of the following general formulas Ia-2, Ia-4, and If-2:

4. A luminous auxiliary material, It is characterized in that The chemical structural formula of the luminescence auxiliary material is any one of Formula 1 to Formula 63, Formula 65 to Formula 179:

5. An organic electroluminescent device comprising a first electrode, a second electrode opposite to the first electrode, and one or more organic layers between the first electrode and the second electrode, It is characterized in that At least one layer of the organic layer comprises the luminescence-assisting material according to any one of claims 1 to 4.

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