A triazine compound and its application

Abstract

The present invention provides a triazine compound and its application, belonging to the technical field of organic electroluminescence. The triazine compound has a structure of formula I. The present invention designs the structure of the triazine compound, and the obtained triazine compound has excellent performance. The organic electroluminescent device prepared as the material of the light-emitting layer has a lower driving voltage, higher current efficiency and lifespan.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescence, and specifically relates to a triazine compound and application thereof. Background Art

[0002] Organic light emitting diodes (OLEDs) are display components that utilize the phenomenon of self-luminescence. They have a wide viewing angle. Compared with liquid crystal display components, OLED components are thinner and lighter, have a faster response speed, and can achieve flexible displays. Therefore, their application as full-color display components or lighting equipment is highly anticipated.

[0003] Generally, organic light emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light emitting element using the organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer interposed between the anode and the cathode.

[0004] Among them, the organic layer is composed of a multilayer structure composed of different substances in most cases in order to improve the efficiency and stability of the organic light-emitting element. For example, it can be composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. If a voltage is applied between the two electrodes in the structure of such an organic light-emitting element, the holes in the anode will be injected into the organic layer, and the electrons in the cathode will also be injected into the organic layer. When the injected holes and electrons meet, excitons are formed. When the excitons release energy and transition to the ground state, photons will be emitted, thereby generating light. Such organic light-emitting elements are widely recognized to have the characteristics of self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed responsiveness.

[0005] At present, the research on organic electroluminescent materials has been widely carried out in academia and industry. Among them, improving device life and current efficiency and reducing driving voltage have always restricted the development of OLED devices. Therefore, designing and finding a compound as a new OLED material to overcome its shortcomings in practical applications is the focus of OLED material research and the future research and development trend. Summary of the invention

[0006] In view of the shortcomings of the prior art, the present invention aims to provide a triazine compound and its application. The present invention is designed through the structure of the triazine compound, and the obtained triazine compound has excellent performance and is suitable for being used as the main material of the light-emitting layer in the organic electroluminescent device. The obtained organic electroluminescent device has a lower driving voltage, a higher current efficiency and a longer life.

[0007] To achieve this object, the present invention adopts the following technical solutions:

[0008] In a first aspect, the present invention provides a triazine compound having a structure as shown in the following formula I:

[0009] Formula I;

[0010] Among them, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 Each is independently selected from any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C1-C12 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group;

[0011] Ar1 and Ar2 are each independently selected from any one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group;

[0012] R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 , Ar1, Ar2 are each independently selected from any one of a deuterium atom (-D), -F, -CN, a C1-C5 alkyl group, a C1-C5 alkoxy group or a C6-C12 aryl group;

[0013] n is selected from an integer between 1 and 4;

[0014] The hydrogen atoms in the compound of formula I may be independently substituted by a deuterium atom (-D), -F, -CN, a C1-C12 alkyl group, a substituted or unsubstituted C1-C12 alkoxy group, a C6-C30 aryl group or a C3-C30 heteroaryl group.

[0015] The triazine compounds obtained by structural design in the present invention have good thermal stability and excellent luminescent performance, and can be used to prepare organic electroluminescent devices, especially as light-emitting layer materials in organic electroluminescent devices, which can effectively reduce the driving voltage of organic electroluminescent devices and improve the current efficiency and life of organic electroluminescent devices.

[0016] It should be noted that, in the present invention, "-D" represents a deuterium atom, and the same applies hereinafter.

[0017] In the present invention, C1-C12 can be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11 or C12.

[0018] C6-C30 can be C6, C8, C10, C12, C13, C15, C18, C20, C24, C28 or C30, etc.

[0019] C3-C30 can be C3, C4, C5, C7, C9, C11, C14, C15, C16, C18, C20, C22, C25, C27 or C30, etc. In the present invention, the C1-C12 alkyl group illustratively includes but is not limited to: methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, tert-pentyl, n-hexyl, cyclohexyl, etc.

[0020] The C1-C12 alkoxy groups include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, tert-pentyloxy, n-hexyloxy, cyclohexyloxy, and the like.

[0021] The C6-C30 aromatic group refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon nucleus of an aromatic hydrocarbon molecule, which may be a monocyclic aromatic group or a condensed-ring aromatic group, and illustratively includes but is not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, indenyl, fluorenyl, perylenyl, phenanthrenyl, pyrenyl, fluoranthenyl or triphenylenyl, etc.

[0022] The C3-C30 heteroaryl group refers to a general term for groups in which one or more aromatic carbon atoms in an aromatic group are replaced by heteroatoms, wherein the heteroatoms include but are not limited to oxygen, sulfur and nitrogen atoms, and the heteroaryl group may be a monocyclic heteroaryl group or a condensed-ring heteroaryl group, and illustratively include but are not limited to pyridyl, pyrimidinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, diarylideneamine, benzofuranocarbazolyl, benzofuranothiophenyl, triazine and the like.

[0023] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. Through the following preferred technical solutions, the objectives and beneficial effects of the present invention can be better achieved and realized.

[0024] As a preferred technical solution of the present invention, the C1-C12 alkyl group is selected from any one of methyl, ethyl, tert-butyl, cyclopentyl, cyclohexyl, octyl and adamantyl, preferably any one of methyl, ethyl or tert-butyl.

[0025] As a preferred technical solution of the present invention, the C1-C12 alkoxy group is selected from any one of methoxy, ethoxy or butoxy, preferably methoxy or ethoxy.

[0026] As a preferred technical solution of the present invention, the C6-C30 aromatic group is selected from any one of phenyl, biphenyl, naphthyl, terphenyl, anthracenyl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthoxyfluorenyl, pyrene, peryl, spirofluorenyl, triphenylene, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthoxyfluorenyl or benzonaphthofluorenyl, preferably any one of phenyl, biphenyl, naphthyl or terphenyl.

[0027] As a preferred technical solution of the present invention, the C3-C30 heteroaryl group is selected from any one of triazine, pyridyl, pyrimidinyl, dibenzofuranyl, dibenzothiophenyl, naphthiobenzofuranyl, naphthiobenzothiophenyl, dinaphthofuranyl, dinaphthothiophenyl, carbazolyl, phenylcarbazolyl, and carbazolylphenyl, and is preferably any one of dibenzofuranyl, dibenzothiophenyl, or carbazolyl.

[0028] As a preferred technical solution of the present invention, the C1-C5 alkyl group is selected from any one of a methyl group, an ethyl group or a tert-butyl group.

[0029] As a preferred technical solution of the present invention, the C1-C5 alkoxy group is selected from any one of methoxy, ethoxy or propoxy.

[0030] As a preferred technical solution of the present invention, the C6-C12 aryl group is selected from any one of phenyl, naphthyl or biphenyl.

[0031] As a preferred technical solution of the present invention, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 are each independently selected from a hydrogen atom or a deuterium atom.

[0032] As a preferred technical solution of the present invention, Ar1 and Ar2 are each independently selected from any one of phenyl, naphthyl, biphenyl or 9,9-dimethylfluorenyl.

[0033] As a preferred technical solution of the present invention, n is 1.

[0034] As a preferred technical solution of the present invention, n is 2.

[0035] As a preferred technical solution of the present invention, n is 3.

[0036] As a preferred technical solution of the present invention, the triazine compound has a structure as shown in the following formula I-1:

[0037] ;

[0038] wherein Ar1, Ar2, and n have the same definitions as above.

[0039] As a preferred technical solution of the present invention, the triazine compound includes any one of compounds 1-57:

[0040]

[0041] As a preferred technical solution of the present invention, the triazine compound includes the following compounds:

[0042] , , , , , , .

[0043] The present invention lists some specific structural forms of the triazine compounds, but the triazine compounds of the present invention are not limited to these listed chemical structures. As long as the structure shown in formula I is based on R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 All structures where Ar1, Ar2, and n satisfy the above-mentioned restrictions should be included.

[0044] It should be noted that the present invention does not have any special restrictions on the preparation method of the above triazine compounds, and the commonly used preparation methods in the art are applicable.

[0045] In a second aspect, the present invention provides an organic electroluminescent device, wherein the organic electroluminescent device comprises the triazine compound as described in the first aspect.

[0046] Preferably, the organic electroluminescent device comprises a first electrode, a second electrode and an organic layer disposed between the first electrode and the second electrode;

[0047] The material of the organic layer includes the triazine compound as described in the first aspect.

[0048] Preferably, the organic layer includes a light-emitting layer;

[0049] The material of the light-emitting layer includes the triazine compound as described in the first aspect.

[0050] In a third aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the second aspect.

[0051] Compared with the prior art, the present invention has the following beneficial effects:

[0052] The triazine compound obtained by the present invention has good luminescent performance by designing the structure of the triazine compound, and can be used to prepare an organic electroluminescent device, especially as a luminescent layer material in an organic electroluminescent device, which can effectively reduce the driving voltage of the organic electroluminescent device and improve the current efficiency and life of the organic electroluminescent device. DETAILED DESCRIPTION

[0053] For the convenience of understanding the present invention, the present invention lists the preparation examples and embodiments as follows. It should be understood by those skilled in the art that the preparation examples and embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0054] Synthesis Example 1

[0055] This embodiment provides a method for synthesizing compound 1, and the synthesis method is as follows:

[0056]

[0057] 0.1 mol of carbazole 1, 0.1 mol of bromide 1, 0.001 mol of tridibenzylideneacetone dipalladium, 0.003 mol of tri-tert-butylphosphine, 0.3 mol of sodium tert-butyl alcohol and 300 mL of dry toluene were added into a 1 L reaction bottle. After evacuating and replacing with nitrogen for 5 times, the temperature was raised to reflux for reaction for 12 h, cooled and cooled to room temperature, and water was added to separate. The organic layer was washed until neutral and then passed through a silica gel column. The column liquid was concentrated and recrystallized from toluene and ethanol to obtain compound 1.

[0058] Compound 1 was tested and the mass-to-charge ratio (m / z) was measured to be 686.22.

[0059] Synthesis Example 2

[0060] This embodiment provides a method for synthesizing compound 2, and its synthesis method is as follows:

[0061]

[0062] Referring to the synthesis method of Synthesis Example 1, bromide 2 is used to replace bromide 1 in Synthesis Example 1, and compound 2 can be obtained while keeping other conditions unchanged.

[0063] Compound 2 was tested and the mass-to-charge ratio (m / z) was measured to be 686.22.

[0064] Synthesis Example 3

[0065] This embodiment provides a method for synthesizing compound 3, as described below:

[0066]

[0067] Referring to the synthesis method of Synthesis Example 1, the chloro compound 3 is used to replace the brominated compound 1 in Synthesis Example 1, the reaction time is changed to 20 hours, and other conditions remain unchanged to obtain Compound 3.

[0068] Compound 3 was tested and the mass-to-charge ratio (m / z) was measured to be 686.22.

[0069] Synthesis Example 4

[0070] This example provides a method for synthesizing compound 57, as described below:

[0071]

[0072] Referring to the synthesis method of Synthesis Example 1, bromide 1 in Synthesis Example 1 is replaced by bromide 4, and compound 57 can be obtained while keeping other conditions unchanged.

[0073] Compound 57 was tested and the mass-to-charge ratio (m / z) was measured to be 711.22.

[0074] Synthesis Example 5

[0075] This embodiment provides a method for synthesizing compound 5, as described below:

[0076]

[0077] Referring to the synthesis method of Synthesis Example 1, the chloro compound A1 is used to replace the brominated compound 1 in Synthesis Example 1, the reaction time is changed to 20 hours, and other conditions remain unchanged to obtain Compound 5.

[0078] Compound 5 was tested and the mass-to-charge ratio (m / z) was measured to be 686.22.

[0079] Synthesis Example 6

[0080] This embodiment provides a method for synthesizing compound 8, as described below:

[0081]

[0082] Referring to the synthesis method of Synthesis Example 1, the chloro compound A2 is used to replace the brominated compound 1 in Synthesis Example 1, and the reaction time is changed to 20 hours. The other conditions remain unchanged to obtain Compound 8.

[0083] Compound 8 was tested and the mass-to-charge ratio (m / z) was measured to be 686.22.

[0084] Synthesis Example 7

[0085] This embodiment provides a method for synthesizing compound 9, as described below:

[0086]

[0087] Referring to the synthesis method of Synthesis Example 1, bromide A3 is used to replace bromide 1 in Synthesis Example 1, and compound 9 can be obtained while keeping other conditions unchanged.

[0088] Compound 9 was tested and the mass-to-charge ratio (m / z) was measured to be 686.22.

[0089] Other compounds for which specific synthesis steps are not listed can be prepared by common knowledge in the art in combination with the above embodiments.

[0090] The specific structures of the compounds used in the following device examples and device comparative examples are shown below:

[0091] , , , , .

[0092] Application Example 1

[0093] This application example provides a green light organic electroluminescent device, using the compound provided by the present invention as a main material of the light-emitting layer, and the structure of the green light organic electroluminescent device is:

[0094] ITO / HT(60nm) / EB-1(20nm) / Main material: PGD-1[5%] (35nm) / TPBI(25 nm) / LiF(0.5nm) / Al(150 nm), where ITO is indium tin oxide, LiF is lithium fluoride, and Al is aluminum.

[0095] The preparation method of the green organic electroluminescent device is as follows:

[0096] The material was placed in a vacuum chamber and evacuated to 1×10 -5 ~1×10 -6 Pa was vacuum evaporated onto the cleaned ITO substrate in turn to prepare an OLED device.

[0097] PGD-1[5%] refers to the doping ratio of the dye, that is, the volume ratio of the main material to the dye PGD-1 is 95:5; HT is the hole transport material, and EB-1 is the electron blocking layer.

[0098] The main material of the light-emitting layer of the green organic electroluminescent device provided in this application example is compound 1.

[0099] Application Example 2-7, Comparative Application Example 1-2

[0100] Application Examples 2-7 and Comparative Application Examples 1-2 respectively provide a green light organic electroluminescent device, which differs from Application Example 1 only in that the main material of the light-emitting layer is replaced with other compounds (see Table 1 below for details), and the other preparation steps and conditions are the same as those of Application Example 1.

[0101] Performance Testing

[0102] The voltage, brightness, current efficiency and LT95 of the organic electroluminescent device provided above were tested, wherein the voltage and current efficiency were measured at a brightness of 1000 cd / m 2 The corresponding value, LT95, refers to maintaining the initial current density of the device at 10mA / cm 2 The time required for the device efficiency to drop to 95% of the efficiency corresponding to the initial current density is constant. The driving voltage, current efficiency and LT95 are relative values. The specific test results are shown in Table 1 below:

[0103] Table 1

[0104]

[0105] From the above content, it can be seen that the triazine compounds obtained by designing the structure of the triazine compounds in the present invention have good luminescence properties and can be used to prepare organic electroluminescent devices, especially as light-emitting layer materials in organic electroluminescent devices, which can effectively reduce the driving voltage of the organic electroluminescent devices and improve the current efficiency and life of the organic electroluminescent devices.

[0106] From the comparison between Application Example 4 and Application Examples 1-3 and Application Examples 5-7, it can be seen that the driving voltage of the organic electroluminescent device can be further reduced by designing the triazine compound to contain two cyano groups.

[0107] From the comparison between Application Examples 6-7 and Application Examples 1-5, it can be seen that using the triazine compound conforming to the structure of Formula I-1 as the main material of the light-emitting layer in the organic electroluminescent device can further improve the current efficiency and life of the organic electroluminescent device.

[0108] In summary, the present invention designs the structure of triazine compounds and uses triazine compounds with specific structures as the main material of the light-emitting layer in the organic electroluminescent device, which can effectively reduce the driving voltage of the organic electroluminescent device and improve the current efficiency and life of the organic electroluminescent device.

[0109] The present invention illustrates the detailed process flow of the present invention through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned detailed process flow, that is, it does not mean that the present invention must rely on the above-mentioned detailed process flow to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of various raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A triazine compound, characterized in that: The triazine compound has a structure as shown in the following formula I: Formula I; Among them, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 Each is independently selected from any one of a hydrogen atom and a deuterium atom; Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C30 aryl groups; The substituents in Ar1 and Ar2 are each independently selected from any one of a deuterium atom, -F, -CN, a C1-C5 alkyl group or a C1-C5 alkoxy group; n is 1 or 2; The hydrogen atoms in the compound of formula I may each independently be substituted by a deuterium atom, -F, -CN, a C1-C12 alkyl group, or a substituted or unsubstituted C1-C12 alkoxy group; The C1-C12 alkyl group is selected from any one of methyl, ethyl, tert-butyl, cyclopentyl, cyclohexyl, octyl or adamantyl; The C1-C12 alkoxy group is selected from any one of methoxy, ethoxy or butoxy; The C6-C30 aryl group is selected from any one of phenyl, biphenyl, naphthyl, terphenyl, anthracenyl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthfluoroenyl, pyrenyl, peryl, spirofluorenyl, triphenylene, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthfluoroenyl or benzonaphthfluoroenyl; The C1-C5 alkyl group is selected from any one of methyl, ethyl or tert-butyl; The C1-C5 alkoxy group is selected from any one of methoxy, ethoxy or propoxy.

2. The triazine compound according to claim 1, characterized in that The Ar1 and Ar2 are each independently selected from any one of phenyl, naphthyl, biphenyl and 9,9-dimethylfluorenyl.

3. The triazine compound according to claim 1, characterized in that: The triazine compound has a structure as shown in the following formula I-1: ； The n is 1 or 2.

4. The triazine compound according to claim 1, characterized in that: The triazine compound includes any one of the following compounds: ； ； ； 。 5. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises the triazine compound according to any one of claims 1 to 4.

6. The organic electroluminescent device according to claim 5, characterized in that: The organic electroluminescent device comprises a first electrode, a second electrode and an organic layer disposed between the first electrode and the second electrode; The material of the organic layer includes the triazine compound as claimed in any one of claims 1 to 4.

7. The organic electroluminescent device according to claim 6, characterized in that: The organic layer includes a light-emitting layer; The material of the light-emitting layer includes the triazine compound according to any one of claims 1 to 4.

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