A compound containing triazine and phenanthrene structures and its application

By using compounds containing triazine and phenanthrene structures as the luminescent layer or electron transport layer material of OLED, the improvement needs of existing OLEDs in terms of device voltage, current efficiency and life are solved, and the effects of low voltage, high efficiency and long life are achieved.

CN114835697BActive Publication Date: 2025-06-06JIANGSU SUNERA TECH CO LTD
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Patent Information

Application Number
CN202110143058.1
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2021-02-02
Publication Date
2025-06-06
Estimated Expiration
2041-02-02

AI Technical Summary

Technical Problem

There are improvements in the voltage, current efficiency and life of existing triplet luminescent phosphorescence OLEDs, especially in terms of light-up voltage and high temperature life.

Method used

A compound containing triazine and phenanthrene structures is provided, whose structure is represented by a specific general formula, with suitable HOMO and LUMO energy levels, higher T1 energy levels and increased molecular asymmetry, for use as a light emitting layer or electron transport layer material.

Benefits of technology

This compound can achieve low voltage, low light-on voltage, high efficiency and long life, especially long life under high temperature conditions, improving the overall performance of the device.

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Abstract

The present invention relates to a compound containing triazine and phenanthrene structures and application thereof, belonging to the field of semiconductor technology. The present invention provides a compound having a structure as shown in general formula (1). After the compound of the present invention is applied to a light-emitting layer or an electron transport layer of an OLED device, the voltage of the device can be effectively reduced, and the current efficiency and service life of the device can be improved.
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Description

Technical Field

[0001] The invention relates to the field of semiconductor technology, in particular to a compound containing triazine and phenanthrene structures and application thereof. Background Art

[0002] There may be a hole transport region between the anode and the light-emitting layer of the organic electroluminescent device, and there may be an electron transport region between the light-emitting layer and the cathode. Holes from the anode may migrate to the light-emitting layer through the hole transport region, and electrons from the cathode may migrate to the light-emitting layer through the electron transport region, and the holes and electrons recombine in the light-emitting layer to generate excitons. According to the principles of quantum mechanics, organometallic compound materials as doping materials can achieve an internal quantum yield of 100%.

[0003] Nevertheless, for triplet-luminescent phosphorescent OLEDs, there is still a need for improvement in device voltage, current efficiency and life. The performance of the host material in the light-emitting layer usually affects the above-mentioned key properties of the organic electroluminescent device to a large extent. According to the prior art, the compounds used as host materials usually contain triazine groups. When the existing triazine derivatives are used as host materials, there is a need for improvement in device voltage, current efficiency, especially in turn-on voltage and device life. The present invention provides a host replacement material with low voltage, high efficiency, long life, especially low turn-on voltage and long high-temperature life.

[0004] For phosphorescent OLED, there is usually an imbalance between holes and electrons in the light-emitting layer, and the device efficiency roll-off is serious under high current density. The present invention also provides a combination of two host materials, which can effectively solve the above-mentioned drawbacks. Summary of the invention

[0005] In view of the above problems existing in the prior art, a compound containing triazine and phenanthrene structures and its application are provided. The present invention provides a main body replacement material with low voltage and low start-up voltage, high efficiency, and especially longer life and longer high temperature life.

[0006] The technical solution of the present invention is:

[0007] A compound containing triazine and phenanthrene structures, wherein the compound structure is shown in general formula (1):

[0008]

[0009] In the general formula (1), Ar 1 Indicates substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 One of the heteroaryl groups;

[0010] Z 1 Each occurrence is represented independently as CR 1 , Z 2 Each occurrence is represented independently as CR 2 ;

[0011] R 1 , R 2 Each occurrence is independently represented by one of H, deuterium, phenyl, biphenyl, naphthyl, phenanthryl, dibenzofuranyl, and carbazolyl; Z at the connection 2 It is represented by C;

[0012] L 1 It is represented by phenylene, biphenylene or the structure represented by general formula (2);

[0013]

[0014] In the general formula (2), Z 3 Indicated as CR 3 , R 3 Each occurrence of the same or different radicals is represented by one of H, deuterium, phenyl, biphenyl, naphthyl, phenanthryl, dibenzofuranyl, and carbazolyl; It is expressed as in the general formula (1) Connection position, any Z indicated by "*" 3 Can be connected with Z by single key 2 Connected, Z at the connection 2 , Z 3 It is represented by C;

[0015] The substituents for the substituent groups are selected from deuterium, tritium, cyano, halogen, C 1-10 Alkyl, C 6 -C 30 Aryl, C 3 -C 30 one or more of heteroaryl groups;

[0016] The heteroatom is an oxygen, sulfur or nitrogen atom.

[0017] In a preferred embodiment, the compound structure is represented by any one of the general formulas (3-1) to (3-5):

[0018]

[0019] The compound structure is preferably represented by any one of the general formulas (4-1) to (4-6):

[0020]

[0021]

[0022] In a preferred embodiment, the compound structure is represented by any one of the general formulas (5-1) to (5-8):

[0023]

[0024]

[0025] Preferably, the Ar 1 represents phenyl, biphenyl, naphthyl, phenanthryl, dibenzofuranyl or carbazolyl;

[0026] The substituent for the substituent group may be selected from one or more of deuterium, tritium, methyl, tert-butyl, cyano, fluorine, phenyl, biphenyl, phenanthryl, carbazolyl, and dibenzofuranyl.

[0027] Preferably, the Z 2 Each occurrence is represented independently as CR 2 , and there is an R 2 Represents phenyl, and the remaining R 2 represents H; preferably, when L 1 When expressed as general formula (2), Ar 1 It is represented by dibenzofuranyl or carbazolyl.

[0028] In a preferred embodiment, the specific structure of the compound is any one of the following structures:

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036] An organic electroluminescent device comprises a cathode, an anode and a functional layer, wherein the functional layer is located between the cathode and the anode, and at least one functional layer in the organic electroluminescent device contains the compound containing triazine and phenanthrene structures.

[0037] In a preferred embodiment, the functional layer includes a light-emitting layer, and the light-emitting layer contains the compound containing triazine and phenanthrene structures; preferably, the light-emitting host material of the light-emitting layer is a mixture of the compound containing triazine and phenanthrene structures and any one or more of the compounds GH-1-GH-170, and the specific structure of the compound GH-1-GH-170 is:

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046] In a preferred embodiment, the functional layer comprises a hole blocking layer and / or an electron transport layer, and the hole blocking layer and / or the electron transport layer contain the compound containing triazine and phenanthrene structures.

[0047] A lighting or display element, comprising the organic electroluminescent device.

[0048] Compared with the prior art, the beneficial technical effects of the present invention are:

[0049] 1) The compound provided by the present invention has suitable HOMO and LUMO energy levels, which can ensure efficient injection and recombination of carriers in the light-emitting layer, and ensure low voltage and high efficiency of the device.

[0050] 2) The higher T1 energy level of the compound provided by the present invention can ensure the energy transfer efficiency between the host and the guest.

[0051] 3) The introduction of the phenanthrene group in the compound provided by the present invention increases the asymmetry of the molecule, reduces the crystallinity of the molecule (high Tg), and helps to improve the high temperature stability of the device.

[0052] 4) The compound provided by the present invention has strong stereochemistry and weak intermolecular interactions, so it has the characteristics of being difficult to crystallize, having a low evaporation temperature, and having good film-forming properties, and has excellent industrial processing performance.

[0053] 5) Cross-talk risk (because the blue and green light pixels have higher turn-on voltage than red light, there is a risk of lighting up adjacent red light pixels while lighting up blue and green light pixels) has always troubled OLED display manufacturers. The compound provided by the present invention has a rigid large π conjugated group and an acceptor group connected by a specific group, which can significantly improve the electron mobility of the material and help improve the device voltage and turn-on voltage compared with the comparative compound.

[0054] 6) Device life, especially high-temperature device life, has always restricted the promotion of OLED displays in various application fields. The compounds provided by the present invention have high chemical stability, which helps to reduce the efficiency roll-off under high current density and also helps to increase device life and high-temperature device life. BRIEF DESCRIPTION OF THE DRAWINGS

[0055] Figure 1 This is a schematic diagram of the structure of an OLED device in which the materials listed in the present invention are applied;

[0056] Among them, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is an electron transport layer, 8 is an electron injection layer, 9 is a cathode layer, and 10 is a CPL layer. DETAILED DESCRIPTION

[0057] The principles and features of the present invention are described below in conjunction with the accompanying drawings and embodiments. The examples given are only used to explain the present invention and are not used to limit the scope of the present invention.

[0058] In the present invention, unless otherwise specified, HOMO means the highest occupied orbital of a molecule, and LUMO means the lowest unoccupied orbital of a molecule. In addition, in the present invention, HOMO and LUMO energy levels are expressed in absolute values, and the comparison between energy levels is also a comparison of the magnitude of their absolute values. Those skilled in the art know that the greater the absolute value of an energy level, the lower the energy of the energy level.

[0059] Any numerical range listed herein is intended to include all sub-ranges with the same numerical precision included in the listed range. For example, "1.0 to 10.0" means all sub-ranges (and including 1.0 and 10.0) included between the listed minimum value 1.0 and the listed maximum value 10.0, that is, all sub-ranges with a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0. Any maximum numerical limit listed herein is intended to include all smaller numerical limits included in this article, and any minimum numerical limit listed herein is intended to include all larger numerical limits included in this article. Therefore, the applicant reserves the right to modify this specification including the claims to clearly describe any sub-ranges falling within the scope clearly described herein.

[0060] In the accompanying drawings, the sizes of layers and regions may be exaggerated for clarity. It will also be understood that when a layer or element is referred to as being "on" another layer or substrate, the layer or element may be directly on the other layer or substrate, or there may be intervening layers. In addition, it will be understood that when a layer is referred to as being "between" two layers, the layer may be the only layer between the two layers, or there may be one or more intervening layers. The same reference numerals throughout the text represent the same elements.

[0061] In the present invention, when describing electrodes and organic electroluminescent devices, as well as other structures, the words "upper", "lower", "top" and "bottom" used to indicate orientation only indicate the orientation in a certain state, and do not mean that the related structure can only exist in the orientation described; on the contrary, if the structure can change its position, such as inverted, the orientation of the structure will be changed accordingly. Specifically, in the present invention, the "bottom" or "lower" side of the electrode refers to the side of the electrode close to the substrate during the preparation process, and the opposite side away from the substrate is the "top" or "upper" side.

[0062] In the present specification, "aryl" refers to a group having at least one aromatic hydrocarbon moiety and generally the aromatic hydrocarbon moieties are connected by a single bond and a non-aromatic fused ring containing a directly or indirectly fused aromatic hydrocarbon moiety. The aryl group can be a monocyclic, polycyclic or fused polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional group.

[0063] In the present specification, the "heterocyclic group" includes a heteroaryl group and a cyclic group containing at least one heteroatom selected from N, O and S and not carbon (C) of a cyclic compound, such as an aryl group, a cycloalkyl group, a condensed ring or a combination thereof. When the heterocyclic group is a condensed ring, each ring or all rings of the heterocyclic group may contain at least one heteroatom.

[0064] More specifically, substituted or unsubstituted C 6 -C 30 Aryl and / or substituted or unsubstituted C 3 -C 30 The heteroaryl group refers to substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted para-terphenyl, substituted or unsubstituted meta-terphenyl, substituted or unsubstituted substituted or unsubstituted triphenylene, substituted or unsubstituted perylene, substituted or unsubstituted indenyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenathiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, combinations thereof, or condensed rings of combinations of the foregoing groups, but are not limited thereto.

[0065] The C of the present invention 1 -C 10 Alkyl (including straight-chain alkyl and branched alkyl) refers to methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl and the like, but is not limited thereto.

[0066] The halogen atom described in the present invention refers to a chlorine atom, a fluorine atom or a bromine atom, but is not limited thereto.

[0067] Example 1: Synthesis of Compound 2:

[0068]

[0069] 0.02 mol of raw material A-1 and 0.023 mol of intermediate B-1 were added to 150 mL of a mixed solvent of toluene: ethanol = 2:1, and 3 mol / L of K 2 CO 3 15 mL of aqueous solution, after deoxygenation, 0.0004 mol Pd(PPh 3 ) 4, heated to 110°C under nitrogen atmosphere, reacted for 48 hours, sampled and plated, cooled and filtered after the reaction of raw material A-1 was complete, the filtrate was evaporated to remove the solvent, and the crude product was passed through a silica gel column to obtain compound 2; elemental analysis structure (C47H28N4O) theoretical value: C, 84.92; H, 4.25; N, 8.43; test value: C, 84.95; H, 4.26; N, 8.43. LC-MS: measured value: 665.35 ([M+H]+), accurate mass: 664.23.

[0070] The following target compound was synthesized by referring to the preparation process of Example 1; the reaction conditions were the same, except that the intermediate B and raw material A listed in Table 1 below were used;

[0071] Table 1

[0072]

[0073]

[0074]

[0075] The synthetic route of intermediate B-2 is as follows:

[0076]

[0077] 0.05 mol of raw material I-1 and 0.08 mol of bis-pinacol borate were added to 60 mL of 1,4-dioxane, and 0.001 mol of Pd(dba) was added after deoxygenation. 2 and 0.002 mol Xphos (2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl), react at 110°C for 18 hours under a nitrogen atmosphere, take a sample point plate, and after the reactants are completely reacted, cool and filter, and the filtrate is evaporated to remove the solvent, and the crude product is passed through a silica gel column to obtain intermediate I-1;

[0078] 0.02 mol of intermediate I-1 and 0.024 mol of raw material II-1 were added to 150 mL of a mixed solvent of toluene: ethanol = 2:1, and 3 mol / L of K 2 CO 3 15 mL of aqueous solution, after deoxygenation, 0.0004 mol Pd(PPh 3 ) 4 , heat to 110°C under a nitrogen atmosphere, react for 48 hours, take a sample plate, and after the intermediate I-1 is completely reacted, cool and filter, evaporate the filtrate to remove the solvent, and pass the crude product through a silica gel column to obtain intermediate II-1;

[0079] Add 0.05 mol of intermediate II-1 and 0.08 mol of bis-pinacol borate to 60 mL of 1,4-dioxane, deoxygenate and add 0.001 mol of Pd(dba) 2 and 0.002 mol Xphos (2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl), react at 110°C for 18 hours under a nitrogen atmosphere, take a sample point plate, and after the reactants are completely reacted, cool and filter, and the filtrate is evaporated to remove the solvent, and the crude product is passed through a silica gel column to obtain intermediate B-2;

[0080] The synthesis steps of intermediate B-1, intermediate B-3 to intermediate B-15 are similar to those of intermediate B-2, except that the raw materials used are changed. The specific raw materials used are shown in Table 2 below:

[0081] Table 2

[0082]

[0083]

[0084] The compounds of the present invention are used in light-emitting devices and can be used as light-emitting layer or electron transport layer materials. The compounds prepared in the above embodiments of the present invention were tested for their physicochemical and photoelectric properties, and the test results are shown in Table 3:

[0085] Table 3

[0086]

[0087]

[0088] Note: The triplet energy level T1 is tested by Horiba's Fluorolog-3 series fluorescence spectrometer, and the material test sample is 2*10 -5 mol / L toluene solution; the glass transition temperature Tg is measured by differential scanning calorimetry (DSC, DSC204F1 differential scanning calorimeter of NETZSCH, Germany), with a heating rate of 10°C / min; the highest occupied molecular orbital HOMO energy level is tested by an ionization energy test system (IPS-3), and the test is an atmospheric environment; Eg is tested by a double-beam UV-visible spectrophotometer (model: TU-1901), LUMO=HOMO+Eg. The electron mobility test is to make the material of the present invention into a single-charge device and measure it by the SCLC method.

[0089] From the data in the above table, it can be seen that the organic compound of the present invention has a high glass transition temperature (Tg), which can improve the phase stability and high temperature stability of the material film; the organic compound of the present invention has suitable HOMO and LUMO energy levels, which can reduce the injection barrier of carriers, reduce the device voltage and improve the device efficiency. The organic compound of the present invention has a high T1 energy level, and its use as a main material can ensure the energy transfer efficiency between the host and the guest and inhibit energy loss. (Corresponding to the conventional technical effect)

[0090] Surprisingly, the organic compounds of the present invention have high electron mobility, which helps to improve the device voltage (especially the turn-on voltage) and current efficiency.

[0091] The following describes in detail the application effects of the OLED materials synthesized by the present invention in devices through device embodiments 1-25 and device comparative examples 1-9. The device manufacturing processes of device embodiments 2-25 and device comparative examples 1-9 of the present invention are exactly the same as those of device embodiment 1, and the same substrate materials and electrode materials are used, and the film thickness of the electrode materials is also the same. The difference is that the light-emitting layer or the electron transport layer in the device is replaced.

[0092] Device Example 1

[0093] like Figure 1As shown, the transparent substrate layer 1 is a transparent PI film, and the anode layer 2 (ITO (15nm) / Ag (150nm) / ITO (15nm)) is washed, that is, washed with a detergent (SemiClean M-L20), washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the anode layer. On the anode layer 2 after the above washing, HT-1 and P-1 are evaporated on the anode layer 2 using a vacuum evaporation device as a hole injection layer 3, with a film thickness of 10nm, and a mass ratio of HT-1 to P-1 of 97:3. Then HT-1 is evaporated as a hole transport layer 4 with a thickness of 130nm. Subsequently, EB-1 is evaporated as an electron blocking layer 5 with a thickness of 40nm. After the above-mentioned electron blocking layer material is evaporated, the light-emitting layer 6 of the OLED light-emitting device is prepared, and its structure includes the compound 2 and GH-1 used in the OLED light-emitting layer 6 as the main materials, GD-1 as the guest material, the mass ratio of compound 2, GH-1, and GD-1 is 47:47:6, and the thickness of the light-emitting layer is 40nm. After the above-mentioned light-emitting layer 6, ET-1 and Liq are vacuum evaporated, the mass ratio of ET-1 and Liq is 1:1, the film thickness is 35nm, and this layer is the electron transport layer 7. On the electron transport layer 7, a LiF layer with a film thickness of 1nm is prepared by a vacuum evaporation device, and this layer is the electron injection layer 8. On the electron injection layer 8, a Mg:Ag electrode layer with a film thickness of 15nm is prepared by a vacuum evaporation device, and the mass ratio of Mg and Ag is 1:9, and this layer is the cathode layer 9. On the cathode layer 9, CP-1 is vacuum evaporated as the CPL layer 10, with a thickness of 70nm. An organic electroluminescent device 1 is obtained.

[0094] The molecular structure formula of the relevant materials is shown below:

[0095]

[0096] After the OLED light-emitting device is completed as described above, the anode and cathode are connected with a known driving circuit, and the voltage, current efficiency, luminescence spectrum and device life of the device are measured. The device examples and comparative examples prepared by the same method are shown in Table 4; the voltage, current efficiency and 20 mA / cm 2 The test results of LT95 life under the conditions are shown in Table 5.

[0097] Table 4

[0098]

[0099]

[0100]

[0101] Table 5

[0102]

[0103] Note: Voltage and current efficiency are calculated at a current density of 10 mA / cm 2 The test was conducted under the following conditions: IVL (current-voltage-luminance) test system (Suzhou Fushida Scientific Instrument Co., Ltd.); the life test system was EAS-62C OLED device life tester from Japan System Technology Co., Ltd.; the device life LT95 refers to the device life under the condition of current density of 20mA / cm 2 The device brightness decays to 95% of the initial brightness when the current density is 20mA / cm 2 When the temperature is 85°C, the time taken for the device brightness to decay to 95% of the initial brightness; the start-up voltage refers to the driving voltage of the device when the device brightness is 1 nit.

[0104] It can be seen from the device data results in Table 5 that: compared with device comparison examples 1-3 and device comparison examples 5-7, the organic light-emitting devices using the compounds of the present invention have obvious improvements in device voltage, which may be mainly related to the higher electron mobility of the compounds of the present invention; compared with device comparison example 4 and device comparison example 8, the organic light-emitting devices using the compounds of the present invention have obvious improvements in device life, which may be mainly related to the higher T1 energy level of the compounds of the present invention ensuring efficient host-guest energy transfer.

[0105] Compared with device comparison example 9, the compound of the present invention has better device voltage and life when used as an electron transport layer material, which may be related to the higher electron mobility of the compound of the present invention, so that it also has certain advantages when used as an ET layer material.

[0106] In general, the organic light-emitting devices using the compounds of the present invention are improved in terms of device voltage, device efficiency and device life compared with OLED devices made of known materials, especially the turn-on voltage and high-temperature life of the device are also significantly improved.

[0107] In order to compare the efficiency attenuation of different devices at high current density, the efficiency attenuation coefficient φ of each device is defined, φ=(μ m -μ 50 ) / μ m ; where μ m Expressed as the maximum current efficiency of the device, μ 50 Indicates that the driving current is 50mA / cm 2 The current efficiency of the device at the time of the current density is measured. The larger the φ value, the more serious the efficiency roll-off of the device. Conversely, it means that the problem of rapid attenuation of the device at high current density has been controlled. The present invention measures the efficiency attenuation coefficient φ of the devices obtained in device embodiments 1-25 and device comparison examples 1-9. The results are shown in Table 6:

[0108] Table 6

[0109]

[0110] It can be seen from the data in Table 6 that the organic light-emitting device prepared using the compound of the present invention has a smaller efficiency attenuation coefficient than that of the comparative example, indicating that the organic electroluminescent device prepared using the compound of the present invention can effectively reduce the efficiency roll-off of the device at high current density.

[0111] In summary, the above are only preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention should be included in the protection scope of the present invention.

Claims

1. A compound containing triazine and phenanthrene structures, It is characterized in that The compound structure is shown in general formula (1): In the general formula (1), Ar 1 is represented by one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted carbazolyl; Z 1 Each occurrence is represented independently as CR 1 , Z 2 Each occurrence is represented independently as CR 2 ; R 1 , R 2 Each occurrence is independently represented by one of H, deuterium, and phenyl; Z at the connection 2 It is represented by C; L 1 It is represented by phenylene and biphenylene; The substituent for the substituent group is optionally selected from one or more of deuterium and phenyl.

2. A compound containing triazine and phenanthrene structures, It is characterized in that The compound structure is shown in general formula (1): In the general formula (1), Ar 1 It is represented by one of phenyl or biphenyl; Z 1 Each occurrence is represented independently as CR 1 , Z 2 Each occurrence is represented independently as CR 2 ; R 1 , R 2 Each occurrence is independently represented by one of H and phenyl; Z at the connection 2 It is represented by C; L 1 It is represented by the structure shown in general formula (2); In the general formula (2), Z 3 Indicated as CR 3 , R 3 Each occurrence of the same or different is represented by one of H and phenyl; It is expressed as in the general formula (1) Connection position, any Z indicated by "*" 3 Can be connected with Z by single key 2 Connected, Z at the connection 2 , Z 3 Indicated as C.

3. The compound according to claim 2, It is characterized in that The compound structure is represented by any one of the general formulas (3-1) to (3-2):

4. The compound according to claim 1, It is characterized in that The compound structure is represented by any one of the general formulas (3-3) to (3-5):

5. The compound according to claim 2, It is characterized in that The compound structure is represented by any one of the general formulas (4-1) to (4-3):

6. The compound according to claim 1, It is characterized in that The compound structure is represented by any one of the general formulas (4-4) to (4-6):

7. The compound according to claim 1, It is characterized in that The compound structure is represented by any one of the general formulas (5-1) to (5-8):

8. The compound according to claim 2, It is characterized in that The compound structure is represented by any one of the general formulas (5-1) to (5-8):

9. The compound according to claim 1, It is characterized in that The Z 2 Each occurrence is represented independently as CR 2 , and there is an R 2 Represents phenyl, and the remaining R 2 Indicates H.

10. The compound according to claim 2, It is characterized in that The Z 2 Each occurrence is represented independently as CR 2 , and there is an R 2 Represents phenyl, and the remaining R 2 Indicates H.

11. The compound according to claim 1 or 2, It is characterized in that The specific structure of the compound is any one of the following structures:

12. An organic electroluminescent device comprising a cathode, an anode and a functional layer, wherein the functional layer is located between the cathode and the anode, It is characterized in that At least one functional layer in the organic electroluminescent device contains the compound containing triazine and phenanthrene structures according to any one of claims 1 to 11.

13. The organic electroluminescent device according to claim 12, wherein the functional layer comprises a light-emitting layer. It is characterized in that The light-emitting layer contains the compound containing triazine and phenanthrene structures according to any one of claims 1 to 11; 14. The organic electroluminescent device according to claim 12, wherein the functional layer comprises a light-emitting layer. It is characterized in that The luminescent host material of the luminescent layer is formed by mixing the compound containing triazine and phenanthrene structures according to any one of claims 1 to 11 with any one or more of the compounds GH-1 to GH-170, and the specific structure of the compounds GH-1 to GH-170 is:

15. The organic electroluminescent device according to claim 12, wherein the functional layer comprises a hole blocking layer and / or an electron transport layer. It is characterized in that The hole blocking layer and / or electron transport layer contains the compound containing triazine and phenanthrene structures according to any one of claims 1 to 11.

16. A lighting or display element, It is characterized in that The lighting or display element comprises the organic electroluminescent device according to any one of claims 12 to 15.

Citation Information

Patent Citations

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