An organic compound with 1,3,5-s-triazine-2,4,6-trione as core and preparation method and application thereof

Abstract

The present invention belongs to the field of semiconductor technology, and specifically relates to an organic compound with 1,3,5-triazine-2,4,6-trione as the core and its application. The organic compound provided by the present invention contains rigid 1,3,5-triazine-2,4,6-trione and benzo five-membered heterocyclic group in spatial structure, and the three substituent groups on the 1,3,5-triazine-2,4,6-trione parent nucleus are cross-spaced to avoid free rotation of the groups, so that the organic compound of the present invention has a higher density and a higher refractive index. The organic compound of the present invention can meet the requirements of the light extraction layer for the thermal stability, film crystallinity and light transmission of the material, and the rigid 1,3,5-triazine-2,4,6-trione and benzo five-membered heterocyclic group improve the thermal stability of the material; high T g Temperature ensures that the material does not crystallize in the thin film state. The compound of the present invention has good application effect and industrialization prospect in OLED light-emitting devices. #imgabs0#

Description

Technical Field

[0001] The present invention belongs to the field of semiconductor technology, and specifically relates to an organic compound with 1,3,5-s-triazine-2,4,6-trione as the core, and a preparation method and application thereof. Background Art

[0002] At present, organic light-emitting diode (OLED) display technology has been applied in smart phones, tablet computers and other fields, and will further expand to large-size application fields such as televisions. However, due to the huge gap between the external quantum efficiency and internal quantum efficiency of OLED, the development of OLED is greatly restricted. Therefore, how to improve the light extraction efficiency of OLED has become a research hotspot. Due to total reflection at the interface between ITO film and glass substrate and the interface between glass substrate and air, the light emitted to the front external space of the OLED device accounts for about 20% of the total EL of the organic material film, and the remaining about 80% of the light is mainly confined in the organic material film, ITO film and glass substrate in the form of waveguide. It can be seen that the light extraction efficiency of conventional OLED devices is low (about 20%), which seriously restricts the development and application of OLED. How to reduce the total reflection effect in OLED devices and increase the proportion of light coupled to the front external space of the device (light extraction efficiency) has attracted widespread attention.

[0003] At present, an important method to improve the external quantum efficiency of OLED is to form structures such as wrinkles, photonic crystals, microlens arrays (MLA) and add surface covering layers on the light-emitting surface of the substrate. The first two structures will affect the angular distribution of the radiation spectrum of OLED, and the third structure has a complex manufacturing process. The use of surface covering layers is simple, and the luminous efficiency is increased by more than 30%, which is of particular concern. According to optical principles, when light passes through a substance with a refractive index of n1 to a substance with a refractive index of n2 (n1>n2), it can only be incident on a substance with a refractive index of n2 within the angle of arcsin(n2 / n1), and the absorption rate B can be calculated using the following formula 1:

[0004]

[0005] Let n1 = n 一般OLED有机材料 =1.70, n2=n 玻璃 =1.46, then 2B = 0.49. Assuming that all the light propagating outward is reflected by the metal electrode, only 51% of the light can be waveguided by the high refractive index organic film and ITO layer. The transmittance of light emitted from the glass substrate to the air can also be calculated. Therefore, when the light emitted from the organic layer is emitted outside the device, only about 17% of the light can be seen by people. Therefore, in view of the current low light extraction efficiency of OLED devices, it is necessary to add a layer of light extraction layer material to the device structure.

[0006] The main problems with the current light extraction layer are as follows: the refractive index of the light extraction layer, such as Alq3, is low in the visible light range, resulting in low light extraction efficiency. After being applied to OLED devices, the device luminous efficiency is only limitedly improved. Summary of the invention

[0007] The object of the present invention is to provide an organic compound with 1,3,5-s-triazine-2,4,6-trione as the core and its application. The organic compound with 1,3,5-s-triazine-2,4,6-trione as the core provided by the present invention has a high refractive index in the visible light field. After being applied to the light extraction layer of an OLED device, the light extraction efficiency of the OLED device can be effectively improved.

[0008] The present invention provides an organic compound with 1,3,5-s-triazine-2,4,6-trione as the core, and the structure of the organic compound is shown in formula (1). The organic compound provided by the present invention contains rigid 1,3,5-s-triazine-2,4,6-trione and benzo five-membered heterocyclic group in spatial structure, and the three substituent groups on the 1,3,5-s-triazine-2,4,6-trione mother nucleus are cross-spaced to avoid free rotation of the groups, so that the organic compound of the present invention has a higher density and a higher refractive index. The organic compound of the present invention can meet the requirements of the light extraction layer for the thermal stability, film crystallinity and light transmission of the material. The rigid 1,3,5-s-triazine-2,4,6-trione and benzo five-membered heterocyclic group improve the thermal stability of the material; high T g Temperature, to ensure that the material does not crystallize in the thin film state and the evaporation temperature is low. The compound of the present invention has good application effect and industrialization prospect in OLED light-emitting devices. BRIEF DESCRIPTION OF THE DRAWINGS

[0009] Figure 1 A schematic diagram of the structure of an OLED device provided in Example 1 of the present invention;

[0010] Among them, 1 is the substrate layer, 2 is the anode layer, 3 is the hole injection layer, 4 is the hole transport layer, 5 is the electron blocking layer, 6 is the light-emitting layer, 7 is the electron transport layer, 8 is the electron injection layer, 9 is the cathode layer, and 10 is the light extraction layer. DETAILED DESCRIPTION

[0011] The present invention provides an organic compound with 1,3,5-s-triazine-2,4,6-trione as the core, and the structure of the organic compound is shown in formula (1):

[0012]

[0013] In formula (1), L1, L2 and L3 are independently a single bond, a substituted or unsubstituted C6-C 30arylene or substituted or unsubstituted 5-30 membered heteroarylene;

[0014] The R1 is a structure represented by formula (2) or formula (3);

[0015] The R2 and R3 are independently substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl or a structure represented by formula (4);

[0016]

[0017] In formula (2) and formula (3), the X is independently -O-, -S- or -N(R0)-, the Z is independently a carbon atom, CH or a nitrogen atom, and the Z at the connection site in formula (2) is a carbon atom; the R0 is a substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted 5-30 membered heteroaryl; said R4-R7 are independently hydrogen atoms, deuterium atoms, halogens, cyano groups, C1-C 10 Alkyl, substituted or unsubstituted C1-C 20 Alkoxy, substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted 5-30 membered heteroaryl;

[0018] In formula (4), R8 and R9 are independently substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0019] The substituents of the substitutable group are independently halogen, cyano, C1-C 10 Alkyl, C1-C 20 Alkoxy, C6-C 20 Aryl or 5-20 membered heteroaryl;

[0020] The heteroatoms in the heteroaryl group and the heteroarylene group are independently one or more of nitrogen, oxygen or sulfur.

[0021] In the present invention, R2 and R3 are preferably independently selected from the group consisting of formula (2), formula (3), formula (4), formula (5) or formula (6):

[0022]

[0023] In the present invention, in formula (5), X1 is -O-, -S-, -C(R 16 R 17 )-、-N(R 18 )-, formula (5) and (6), X2, X3 are independently -O-, -S-, -C(R 16 R17 )-、-N(R 18 )- or a single bond; said R 10 -R 15 are each independently preferably a hydrogen atom, a deuterium atom, a halogen, a cyano group, a C1-C 10 Alkyl, substituted or unsubstituted C1-C 20 Alkoxy, substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted 5-30 membered heteroaryl; said R 16 and R 17 are each independently preferably substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted 5-30 membered heteroaryl or said R 16 , R 17 Together with the C atoms to which they are attached, they form a substituted or unsubstituted five-membered ring or six-membered ring; said R 18 Preferably, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted 5-30 membered heteroaryl; in the present invention, the substituents of the above-mentioned substitutable groups are independently preferably halogen, cyano, C1-C 10 Alkyl, C6-C 20 Aryl or 5-20 membered heteroaryl; the heteroatoms in the heteroaryl and heteroarylene group are independently preferably one or more of nitrogen, oxygen or sulfur.

[0024] In the present invention, the structure of the organic compound with 1,3,5-s-triazine-2,4,6-trione as the core is preferably as shown in formula (1-1):

[0025]

[0026] The R2 and R3 are preferably independently a structure represented by formula (2), formula (3), formula (4), formula (5) or formula (6):

[0027]

[0028] In the present invention, in formula (2) and formula (3), X is independently -O-, -S-, -N(R0)-, and the Z is independently preferably a carbon atom, CH or N, and the Z at the connection site in formula (2) is a carbon atom; the R0 is a substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted 5-30 membered heteroaryl; said R4-R7 are independently preferably a hydrogen atom, a deuterium atom, a halogen, a cyano group, a C1-C 10 Alkyl, substituted or unsubstituted C1-C20 Alkoxy, substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted 5-30 membered heteroaryl; said R8 and R9 are independently preferably substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl; in formula (5), X1 is preferably -O-, -S-, -C(R 16 R 17 )-or-N(R 18 )-; Formula (5) and (6), X2, X3 are each independently preferably -O-, -S-, -C(R 16 R 17 )-、-N(R 18 )- or a single bond; said R 10 -R 15 are each independently preferably a hydrogen atom, a deuterium atom, a halogen, a cyano group, a C1-C 10 Alkyl, substituted or unsubstituted C1-C 20 Alkoxy, substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted 5-30 membered heteroaryl; said R 16 -R 17 are each independently preferably substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted 5-30 membered heteroaryl or said R 16 , R 17 Together with the C atoms to which they are attached, they form a substituted or unsubstituted five-membered ring or a six-membered ring; said R 18 Preferably, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted 5-30 membered heteroaryl; in the present invention, the substituents of the above-mentioned substitutable groups are independently halogen, cyano, C1-C 10 Alkyl, C6-C 20 Aryl or 5-20 membered heteroaryl; the heteroatoms in the heteroaryl and heteroarylene group are selected from one or more of nitrogen, oxygen or sulfur.

[0029] In the present invention, the structure of the organic compound with 1,3,5-s-triazine-2,4,6-trione as the core is preferably any one of formulas (1-2) to (1-5):

[0030]

[0031]

[0032] In the present invention, the structure of the organic compound is preferably as shown in formula (1-6):

[0033]

[0034] In the present invention, L1, L2 and L3 are each independently preferably a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted benzoxazolyl group or a substituted or unsubstituted benzimidazolyl group.

[0035] In the present invention, the R4-R7, R 10 -R 15 Preferably, the radical is independently a hydrogen atom, a deuterium atom, a methyl group, an ethyl group, a tert-butyl group, an adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted piperonyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, or a substituted or unsubstituted carbazolyl group.

[0036] In the present invention, R0, R8-R9, R 16 -R 18 Preferably, the radical is independently methyl, ethyl, tert-butyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted furyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted indenyl, substituted or unsubstituted piperonyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted diphenylfluorenyl, or substituted or unsubstituted carbazolyl.

[0037] In the present invention, the substituents of the substitutable group are independently one or more of a deuterium atom, a methyl group, an ethyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group, a furyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group or a dibenzothienyl group.

[0038] In the present invention, the specific structural formula of the organic compound with 1,3,5-s-triazine-2,4,6-trione as the core is preferably any one of the following structures:

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050] The present invention provides the use of the organic compound with 1,3,5-s-triazine-2,4,6-trione as the core described in the above technical solution in preparing the functional layer of an organic electroluminescent device.

[0051] The present invention provides an organic electroluminescent device, which comprises at least one functional layer containing the organic compound with 1,3,5-s-triazine-2,4,6-trione as the core as described in the above technical solution.

[0052] In the present invention, the functional layer includes a light extraction layer, and the light extraction layer contains the organic compound with 1,3,5-s-triazine-2,4,6-trione as the core as described in the above technical solution.

[0053] In the present invention, the structural schematic diagram of the organic electroluminescent device is as follows Figure 1As shown: the structure of the organic electroluminescent device includes a substrate layer 1, an anode layer 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, an electron transport layer 7, an electron injection layer 8, a cathode layer 9, and a light extraction layer 10 which are stacked in sequence.

[0054] In the present invention, the material of the substrate layer 1 is transparent glass. The material of the anode layer 2 is Ag, with a thickness of 100nm. The material of the hole injection layer 3 is HAT-CN, with a thickness of 10nm. The material of the hole transport layer 4 is HT-1, with a thickness of 140nm. The material of the electron blocking layer 5 is EB-1, with a thickness of 30nm. The material of the light-emitting layer is preferably GH-2 and GH-1 as the main material, and GD-1 as the doping material, the mass ratio of GH-2, GH-1 and GD-1 is 45:45:10, and the thickness is 40nm; the material of the electron transport layer 7 is preferably ET-1 and Liq, the mass ratio of ET-1 and Liq is 1:1, and the thickness is 40nm. The material of the electron injection layer 8 is preferably LiF, with a thickness of 1nm. The material of the cathode layer 9 is preferably Mg and Ag, the mass ratio of Mg and Ag is 1:9, and the thickness is 15nm. The material of the light extraction layer 10 is preferably the organic compound containing an azobenzene skeleton structure as described in the above technical solution, and the thickness is 70 nm.

[0055] In the present invention, the electron transport layer 7 may also serve as a hole blocking layer.

[0056] In the present invention, the chemical structures of the HAT-CN, the HT-1, the EB-1, the GD-1, the ET-1, the GH-1, the GH-2, and the Liq are as follows:

[0057]

[0058] In the present invention, the method for preparing the organic electroluminescent device is preferably vacuum evaporation.

[0059] In order to further illustrate the present invention, the technical solution provided by the present invention is described in detail below in conjunction with the accompanying drawings and embodiments, but they should not be construed as limiting the protection scope of the present invention.

[0060] Example 1: The synthesis of compound (1) was carried out according to the following preparation process:

[0061]

[0062] In a 250 mL three-necked flask, nitrogen was introduced, 0.02 mol of raw material A-1, 350 mL of DMF, 0.067 mol of raw material B-1, and 0.00065 mol of palladium acetate were added, stirred, and then 8 mL of 0.01 mol / mL K3PO4 aqueous solution was added, heated under reflux at 150°C for 18 hours, and a sampling point plate was taken. When the reaction was complete, the mixture was cooled naturally, 180 mL of water was added, the mixture was filtered, and the filter cake was dried in a vacuum drying oven. The residue was purified by silica gel column to obtain compound (1); elemental analysis structure (molecular formula C 42 H 24 N6O6): theoretical value C, 71.18; H, 3.41; N, 11.86; measured value C, 71.15; H, 3.43; N, 11.88. MS: theoretical value 708.18, measured value 709.21.

[0063] Example 2: The synthesis of compound (51) was carried out according to the following preparation process:

[0064]

[0065] In a 250mL three-necked flask, nitrogen was introduced, 0.02mol of raw material A-2, 200mL of DMF, 0.045mol of raw material B-1, and 0.0004mol of palladium acetate were added, stirred, and then 6mL of 0.01mol / mL K3PO4 aqueous solution was added, heated under reflux at 150°C for 15 hours, and the sample point plate was taken, and the reaction was complete. Natural cooling was performed, 100mL of water was added, the mixture was filtered, and the filter cake was dried in a vacuum drying oven. The residue was purified by silica gel column to obtain intermediate C-1;

[0066] Intermediate C-1 continues to participate in the next reaction as a raw material;

[0067] In a 250mL three-necked flask, nitrogen was introduced, 0.02mol of intermediate C-1, 150mL of DMF, 0.023mol of raw material D-1, and 0.0002mol of palladium acetate were added, stirred, and then 3mL of 0.01mol / mL K3PO4 aqueous solution was added, and the mixture was heated under reflux at 150°C for 10 hours. The sample point plate was taken and the reaction was complete. Natural cooling was performed, 80mL of water was added, the mixture was filtered, and the filter cake was dried in a vacuum drying oven. The residue was purified by silica gel column to obtain compound (51); the elemental analysis structure (molecular formula C 47 H 28 N6O5): theoretical value C, 74.59; H, 3.73; N, 11.11; measured value C, 74.61; H, 3.75; N, 11.13. MS: theoretical value 756.21, measured value 757.23.

[0068] Example 3: The synthesis of compound (101) was carried out according to the following preparation process:

[0069]

[0070] The preparation method of compound 101 is the same as that of Example 2, except that raw material D-2 is used to replace raw material D-1 to obtain compound (101); elemental analysis structure (molecular formula C 47 H 30 N6O5): theoretical value C, 74.40; H, 3.99; N, 11.08; measured value C, 74.44; H, 3.97; N, 11.05. MS: theoretical value 758.23, measured value 759.21.

[0071] Example 4: The synthesis of compound (240) was carried out according to the following preparation process:

[0072]

[0073] The preparation method of compound (240) is the same as that of Example 2, except that raw material D-3 is used to replace raw material D-1 to obtain compound (240); elemental analysis structure (molecular formula C 48 H 30 N6O6): theoretical value C, 73.27; H, 3.84; N, 10.68; O, 12.20; measured value C, 73.25; H, 3.81; N, 10.66. MS: theoretical value 786.22, measured value 787.20.

[0074] Example 5: Synthesis of compound (5)

[0075]

[0076] The preparation method of compound (5) is the same as that of Example 2, except that raw material D-4 is used to replace raw material D-1 to obtain compound (5); the elemental analysis structure (molecular formula C 45 H 25 N5O5): theoretical value C, 75.52; H, 3.52; N, 9.79; measured value C, 75.53; H, 3.55; N, 9.83. MS: theoretical value 715.19, measured value 716.22.

[0077] Example 6: The synthesis of compound (71) was carried out according to the following preparation process:

[0078]

[0079] The preparation method of compound (71) is the same as that of Example 2, except that raw material B-2 is used to replace raw material B-1, and raw material D-5 is used to replace raw material D-1, to obtain compound (71); elemental analysis structure (molecular formula C 63 H 44 N6O5): theoretical value C, 78.41; H, 4.60; N, 8.71; measured value C, 78.39; H, 4.58; N, 8.69. MS: theoretical value 964.34, measured value 965.31.

[0080] Example 7: The synthesis of compound (168) was carried out according to the following preparation process:

[0081]

[0082] The preparation method of compound (168) is the same as that of Example 2, except that raw material B-3 is used to replace raw material B-1, and raw material D-6 is used to replace raw material D-1, to obtain compound (168); elemental analysis structure (molecular formula C 47 H 28 N6O5): theoretical value C, 74.59; H, 3.73; N, 11.11; measured value C, 74.61; H, 3.72; N, 11.13. MS: theoretical value 756.21, measured value 757.19.

[0083] Example 8: The synthesis of compound (177) was carried out according to the following preparation process:

[0084]

[0085] In a 250mL three-necked flask, nitrogen was introduced, 0.02mol of raw material A-3, 120mL of DMF, 0.021mol of raw material B-1, 0.0002mol of palladium acetate were added, stirred, and then 3mL of 0.01mol / mL K3PO4 aqueous solution was added, heated under reflux at 150°C for 10 hours, and the sample point plate was taken, and the reaction was complete. Natural cooling was performed, 80mL of water was added, the mixture was filtered, and the filter cake was dried in a vacuum drying oven. The residue was purified by silica gel column to obtain intermediate C-7;

[0086] Intermediate C-7 is used as a raw material to continue to participate in the next reaction;

[0087] In a 250mL three-necked flask, nitrogen was introduced, 0.02mol of intermediate C-7, 150mL of DMF, 0.023mol of raw material D-7, 0.0002mol of palladium acetate were added, stirred, and then 3mL of 0.01mol / mL K3PO4 aqueous solution was added, heated under reflux at 150°C for 12 hours, and the sample point plate was taken, and the reaction was complete. Natural cooling was performed, 100mL of water was added, the mixture was filtered, and the filter cake was dried in a vacuum drying oven. The residue was purified by silica gel column to obtain intermediate C-8;

[0088] In a 250mL three-necked flask, nitrogen was introduced, 0.02mol of intermediate C-8, 150mL of DMF, 0.023mol of raw material D-1, and 0.0002mol of palladium acetate were added, stirred, and then 3mL of 0.01mol / mL K3PO4 aqueous solution was added, and the mixture was heated under reflux at 150°C for 15 hours. The sample point plate was taken and the reaction was complete. After natural cooling, 100mL of water was added, the mixture was filtered and the filter cake was dried in a vacuum drying oven. The residue was purified by silica gel column to obtain compound (177); elemental analysis structure (molecular formula C 55 H 37 N5O4): theoretical value C, 79.41; H, 4.48; N, 8.42; measured value C, 79.39; H, 4.46; N, 8.38. MS: theoretical value 831.28, measured value 832.25.

[0089] Example 9: The synthesis of compound (201) was carried out according to the following preparation process:

[0090]

[0091] The preparation method of compound (201) is the same as that of Example 2, except that raw material B-4 is used to replace raw material B-1, and raw material D-8 is used to replace raw material D-1, to obtain compound (201); elemental analysis structure (molecular formula C 60 H 42 N 10 O3): Theoretical value C, 75.77; H, 4.45; N, 14.73; Test value C, 75.76; H, 4.49; N, 14.77. MS: Theoretical value 950.34, measured value 951.36.

[0092] Example 10: The synthesis of compound (237) was carried out according to the following preparation process:

[0093]

[0094] The preparation method of compound (237) is the same as that of Example 2, except that raw material D-9 is used instead of raw material D-1 to obtain compound (237); elemental analysis structure (molecular formula C54 H 33 N5O6): theoretical value C, 76.50; H, 3.92; N, 8.26; measured value C, 76.48; H, 3.97; N, 8.24. MS: theoretical value 847.24, measured value 848.22.

[0095] Example 11: The synthesis of compound (126) was carried out according to the following preparation process:

[0096]

[0097] The preparation method of compound (126) is the same as that of Example 2, except that raw material B-5 is used to replace raw material B-1, and raw material D-2 is used to replace raw material D-1, to obtain compound (126); elemental analysis structure (molecular formula C 59 H 38 N6O3S2): theoretical value C, 75.14; H, 4.06; N, 8.91; S, 6.80; measured value C, 75.16; H, 4.09; N, 8.93; S, 6.81. MS: theoretical value 942.24, measured value 943.26.

[0098] Application Example 1

[0099] according to Figure 1 The structural schematic diagram of the OLED light-emitting device shown is prepared:

[0100] a) The substrate layer 1 is transparent glass, and an anode layer 2 (Ag, thickness of 100 nm) is deposited on the surface of the substrate layer 1 by vacuum evaporation;

[0101] b) on the surface of the anode layer 2, HAT-CN is deposited by vacuum evaporation with a thickness of 10 nm as the hole injection layer 3;

[0102] c) HT-1 was deposited on the surface of the hole injection layer 3 by vacuum evaporation with a thickness of 140 nm as the hole transport layer 4;

[0103] d) On the surface of the hole transport layer 4, EB-1 is deposited by vacuum evaporation with a thickness of 30 nm as the electron blocking layer 5,

[0104] e) evaporating a light-emitting layer 6 on the surface of the electron blocking layer 5, wherein GH-2 and GH-1 are used as the main materials, GD-1 is used as the doping material, the mass ratio of GH-2, GH-1 and GD-1 is 45:45:10, and the thickness is 40 nm;

[0105] f) on the surface of the light-emitting layer 6, ET-1 and Liq are evaporated by vacuum evaporation in a mass ratio of 1:1 with a thickness of 40 nm to serve as an electron transport layer 7;

[0106] g) vacuum evaporating LiF on the surface of the electron transport layer 7 to a thickness of 1 nm as the electron injection layer 8;

[0107] h) On the surface of the electron injection layer 8, a Mg:Ag layer with a mass ratio of 1:9 and a thickness of 15 nm is vacuum-deposited as the cathode layer 9;

[0108] i) On the surface of the cathode layer 9, the organic substances prepared in Examples 1 to 14 were respectively deposited by vacuum evaporation to a thickness of 70 nm to obtain an OLED light-emitting device having the organic substances prepared in Examples 1 to 11 as the light extraction layer 10.

[0109] Comparative Example 1

[0110] The preparation method is basically the same as that of Application Example 1, except that Alq3 is used to replace the organic matter prepared in Examples 1 to 11, and the thickness is 70 nm, thereby obtaining an OLED light-emitting device with Alq3 as the light extraction layer.

[0111] In this comparative example, the chemical structure of Alq3 is

[0112] The present invention uses the organic compound prepared in Examples 1 to 11 as the light extraction layer to prepare the device and the device prepared in Comparative Example 1 using Alq3 as the light extraction layer to prepare the device in detail to prove the application effect of the synthesized OLED material of the present invention in the device. Compared with the device prepared in Comparative Example 1, the device of the present invention using the organic material prepared in Examples 1 to 11 as the light extraction layer has the same manufacturing method, and uses the same substrate material and electrode material, and the film thickness of the electrode material is also the same. The difference is that the light extraction layer material in the device is changed in Device Examples 1-11. The performance test results of the devices obtained in each embodiment are shown in Table 3.

[0113] Table 2 Device parameters prepared in application examples and reference documents

[0114]

[0115]

[0116] The test data of the obtained electroluminescent device are shown in Table 2.

[0117] Table 2 Device performance of application example 1 and comparative example 1

[0118]

[0119] Note: The current efficiency is tested using the IVL (current-voltage-luminance) test system, and the current density during the test is 10mA / cm 2 .

[0120] The results in Table 2 show that after the organic compound of the present invention is used to prepare an OLED light-emitting device, the light extraction is significantly improved compared with the device comparison example 1, and the device efficiency is improved at the same current density.

[0121] Although the above embodiment describes the present invention in detail, it is only a part of the embodiments of the present invention, not all of the embodiments. Other embodiments can be obtained based on this embodiment without creativity, and these embodiments all fall within the protection scope of the present invention.

Claims

1. An application of an organic compound with 1,3,5-s-triazine-2,4,6-trione as the core in preparing a light extraction layer of an organic electroluminescent device, characterized in that: The structure of the organic compound is shown in formula (1): In formula (1), L1, L2 and L3 are independently a single bond, a phenyl group or a biphenyl group; R1 is a structure represented by formula (2) or formula (3), R4 in the structure represented by formula (2) is a hydrogen atom, Z is a carbon atom, X is -O- or -S-, and R5 is a phenyl group; X in the structure represented by formula (3) is -O- or -S-, Z is a carbon atom, and R6 and R7 are hydrogen atoms; The R2 is a structure shown in formula (2), formula (3) or formula (5), R4 in the structure shown in formula (2) is a hydrogen atom, Z is a carbon atom, X is -O- or -S-, and R5 is a phenyl group; X in the structure shown in formula (3) is -O- or -S-, Z is a carbon atom, R6 and R7 are hydrogen atoms; X2 in the structure shown in formula (5) is a single bond, X1 is -C(R 16 R 17 )-, R 16 and R 17 are independently methyl or ethyl, R 10 and R 11 is hydrogen; The R3 is a structure shown in formula (3), formula (4), formula (5) or formula (6), wherein X in formula (3) is -O- or -S-, Z is a carbon atom, and R6 and R7 are hydrogen atoms; R8 and R9 in formula (4) are phenyl groups; X2 in formula (5) is -O-, -S- or a single bond, and X1 is -N(R 18 )-or-C(R 16 R 17 )-, R 18 is phenyl or substituted phenyl, wherein the substituent of the substituted phenyl is methyl, ethyl or tert-butyl, and R 16 and R 17 is phenyl, R 10 and R 11 is hydrogen; X3 in formula (6) is -C(R 16 R 17 )- or single bond, R 16 and R 17 are independently methyl or ethyl, R 12 , R 13 , R 14 , R 15 is a hydrogen atom; 2. An application of an organic compound with 1,3,5-s-triazine-2,4,6-trione as the core in preparing a light extraction layer of an organic electroluminescent device, characterized in that: The structure of the organic compound is shown below:

3. An application of an organic compound with 1,3,5-s-triazine-2,4,6-trione as the core in preparing a light extraction layer of an organic electroluminescent device, characterized in that: The structure of the organic compound is shown below:

4. An application of an organic compound with 1,3,5-s-triazine-2,4,6-trione as the core in preparing a light extraction layer of an organic electroluminescent device, characterized in that: The structure of the organic compound is shown below:

5. The use according to claim 1, characterized in that: The specific structural formula of the organic compound is any one of the following structures:

6. An organic electroluminescent device, characterized in that: At least the light extraction layer in the functional layer of the organic electroluminescent device contains an organic compound with 1,3,5-s-triazine-2,4,6-trione as the core; The structure of the organic compound with 1,3,5-s-triazine-2,4,6-trione as the core is shown in formula (1): In formula (1), L1, L2 and L3 are independently a single bond, a phenyl group or a biphenyl group; R1 is a structure represented by formula (2) or formula (3), R4 in the structure represented by formula (2) is a hydrogen atom, Z is a carbon atom, X is -O- or -S-, and R5 is a phenyl group; X in the structure represented by formula (3) is -O- or -S-, Z is a carbon atom, and R6 and R7 are hydrogen atoms; The R2 is a structure shown in formula (2), formula (3) or formula (5), R4 in the structure shown in formula (2) is a hydrogen atom, Z is a carbon atom, X is -O- or -S-, and R5 is a phenyl group; X in the structure shown in formula (3) is -O- or -S-, Z is a carbon atom, R6 and R7 are hydrogen atoms; X2 in the structure shown in formula (5) is a single bond, X1 is -C(R 16 R 17 )-, R 16 and R 17 are independently methyl or ethyl, R 10 and R 11 is hydrogen; The R3 is a structure shown in formula (3), formula (4), formula (5) or formula (6), wherein X in formula (3) is -O- or -S-, Z is a carbon atom, and R6 and R7 are hydrogen atoms; R8 and R9 in formula (4) are phenyl groups; X2 in formula (5) is -O-, -S- or a single bond, and X1 is -N(R 18 )-or-C(R 16 R 17 )-, R 18 is phenyl or substituted phenyl, wherein the substituent of the substituted phenyl is methyl, ethyl or tert-butyl, and R 16 and R 17 is phenyl, R 10 and R 11 is hydrogen; X3 in formula (6) is -C(R 16 R 17 )- or single bond, R 16 and R 17 are independently methyl or ethyl, R 12 , R 13 , R 14 , R 15 is a hydrogen atom; 7. An organic electroluminescent device, characterized in that: At least the light extraction layer in the functional layer of the organic electroluminescent device contains an organic compound with 1,3,5-s-triazine-2,4,6-trione as the core; The structure of the organic compound with 1,3,5-s-triazine-2,4,6-trione as the core is shown below:

8. An organic electroluminescent device, characterized in that: At least the light extraction layer in the functional layer of the organic electroluminescent device contains an organic compound with 1,3,5-s-triazine-2,4,6-trione as the core; The structure of the organic compound with 1,3,5-s-triazine-2,4,6-trione as the core is shown below:

9. An organic electroluminescent device, characterized in that: At least the light extraction layer in the functional layer of the organic electroluminescent device contains an organic compound with 1,3,5-s-triazine-2,4,6-trione as the core; The structure of the organic compound with 1,3,5-s-triazine-2,4,6-trione as the core is shown below:

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