A compound and its applications

Abstract

The present invention relates to a compound and its application, and the compound has a structure shown in Formula I. The compound provided by the present invention uses indolocarbazole with two nitrogen atoms substituting carbazole at the 4,5 positions to form a large conjugated ring, which increases the planarity and rigidity of the molecule, thereby effectively improving the overall performance of the molecule. When the compound of the present invention is used in an organic electroluminescent device, especially as a light-emitting layer material, it can effectively improve the carrier transport balance in the device, thereby ensuring that the device obtains excellent effects of high luminous efficiency and low turn-on voltage.

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescence, and particularly to a compound and its application. Background Art

[0002] In recent years, optoelectronic devices based on organic materials have become increasingly popular. The inherent flexibility of organic materials makes them very suitable for manufacturing on flexible substrates, and beautiful and cool optoelectronic products can be designed and produced according to requirements, obtaining incomparable advantages over inorganic materials. Examples of such organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic photovoltaic cells, organic sensors, etc. Among them, the development of OLEDs has been particularly rapid and has achieved commercial success in the field of information display. OLEDs can provide three primary colors of high saturation, red, green, and blue. The full-color display device made of them does not require an additional backlight source and has the advantages of gorgeous colors, lightness, and softness.

[0003] The core of an OLED device is a thin-film structure containing various organic functional materials. Common functionalized organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, as well as light-emitting host materials and light-emitting guests (dyes), etc. When powered on, electrons and holes are respectively injected, transported to the light-emitting region and recombined here, thereby generating excitons and emitting light.

[0004] People have developed a variety of organic materials. Combining various peculiar device structures can improve the carrier mobility, regulate the carrier balance, break through the electroluminescence efficiency, and delay the device decay. For quantum mechanical reasons, common fluorescent emitters mainly utilize singlet excitons generated when electrons and holes combine and are still widely used in various OLED products. Some metal complexes such as iridium complexes can emit light by simultaneously utilizing triplet excitons and singlet excitons and are called phosphorescent emitters. Their energy conversion efficiency can be increased by up to four times compared with traditional fluorescent emitters. Thermally activated delayed fluorescence (TADF) technology can still effectively utilize triplet excitons to achieve high luminescence efficiency without using metal complexes by promoting the conversion of triplet excitons to singlet excitons. Thermally activated sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize the emitter through energy transfer and can also achieve high luminescence efficiency.

[0005] As OLED products gradually enter the market, people have higher and higher requirements for the performance of such products. The currently used OLED materials and device structures cannot completely solve various problems such as the efficiency, lifespan, and cost of OLED products. Summary of the Invention

[0006] One of the objectives of the present invention is to provide a compound, which can improve the luminous efficiency and reduce the driving voltage when applied to an OLED device.

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

[0008] A compound having the structure shown in Formula I:

[0009]

[0010] In Formula I, Ar is selected from one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups;

[0011] L is selected from one of a single bond, substituted or unsubstituted C6-C30 arylene groups, and substituted or unsubstituted C3-C30 heteroarylene groups;

[0012] Ring A, Ring B, Ring C, Ring D, and Ring E are each independently selected from one of substituted or unsubstituted C6-C30 aromatic rings and substituted or unsubstituted C3-C30 heterocyclic rings.

[0013] When substituents exist on the above-mentioned Ar, L, Ring A, Ring B, Ring C, Ring D, and Ring E, the substituents are selected from one of halogen, cyano, nitro, hydroxyl, C1-C10 linear alkyl groups, C3-C10 cycloalkyl groups, C1-C10 alkoxy groups, C1-C10 thioalkoxy groups, C1-C10 silyl groups, amino groups, C6-C30 arylamino groups, C3-C30 heteroarylamino groups, C6-C30 monocyclic aryl groups, C10-C30 fused-ring aryl groups, C3-C30 monocyclic heteroaryl groups, and C6-C30 fused-ring heteroaryl groups, or a combination of at least two of them.

[0014] The above-mentioned "substituted or unsubstituted" groups can be substituted with one substituent or multiple substituents. When there are multiple substituents, they can be selected from different substituents. When the same expression is involved in the present invention, it has the same meaning, and the selection range of the substituents is as shown above and will not be elaborated one by one.

[0015] Further preferably, the compound of the present invention has the structure shown in Formula I-1:

[0016]

[0017] In Formula I-1, the definitions of Ar, L, Ring A, Ring B, and Ring D are the same as those in Formula I;

[0018] The ring C1 and the ring E1 are each independently selected from a substituted or unsubstituted C6-C26 aromatic ring and a substituted or unsubstituted C3-C26 heterocyclic ring; preferably, the ring C1 and the ring E1 are each independently selected from a substituted or unsubstituted C6-C10 aromatic ring and a substituted or unsubstituted C3-C10 heterocyclic ring;

[0019] When substituents are present on the above-mentioned ring C1 and ring E1, the substituents are selected from a halogen, a cyano group, a nitro group, a hydroxyl group, a C1-C10 linear alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a C1-C10 thioalkoxy group, a C1-C10 silyl group, an amino group, a C6-C30 arylamino group, a C3-C30 heteroarylamino group, a C6-C30 monocyclic aryl group, a C10-C30 fused-ring aryl group, a C3-C30 monocyclic heteroaryl group, and a C6-C30 fused-ring heteroaryl group, or a combination of at least two of them.

[0020] More preferably, the compound of the present invention has the structure shown in the following formula I-2:

[0021]

[0022] In formula I-2, the definitions of Ar and L are the same as those in formula I;

[0023] The X 1 -X 16 are each independently selected from CR 1 or N, and the R 1 is independently selected from hydrogen, a halogen, a cyano group, a nitro group, a hydroxyl group, a C1-C10 linear alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a C1-C10 thioalkoxy group, a C1-C10 silyl group, an amino group, a C6-C30 arylamino group, a C3-C30 heteroarylamino group, a C6-C30 monocyclic aryl group, a C10-C30 fused-ring aryl group, a C3-C30 monocyclic heteroaryl group, a C6-C30 fused-ring heteroaryl group, or a combination of at least two of them;

[0024] Preferably, the X 1 -X 16 are each independently selected from CR 1 , and the R 1 is independently selected from hydrogen, a halogen, a cyano group, a nitro group, a hydroxyl group, a C1-C10 linear alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a C1-C10 thioalkoxy group, a C1-C10 silyl group, an amino group, a C6-C30 arylamino group, a C3-C30 heteroarylamino group, a C6-C30 monocyclic aryl group, a C10-C30 fused-ring aryl group, a C3-C30 monocyclic heteroaryl group, a C6-C30 fused-ring heteroaryl group, or a combination of at least two of them;

[0025] Even more preferably, the X1 -X 16 are each independently selected from CR 1 , where the R 1 is hydrogen.

[0026] Further preferably, in the above formula I, formula (I-1), and formula (I-2), the Ar is selected from substituted or unsubstituted C3-C30 electron-deficient heteroaryl groups; more preferably, the Ar is selected from substituted or unsubstituted C3-C30 electron-deficient heteroaryl groups containing nitrogen;

[0027] When the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, nitro, hydroxy, C1-C10 linear alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 fused-ring aryl, C3-C30 monocyclic heteroaryl, and C6-C30 fused-ring heteroaryl.

[0028] The "electron-deficient heteroaryl group (also known as an electron-deficient group)" in this specification refers to a group that reduces the electron cloud density on the benzene ring after substituting the hydrogen on the benzene ring. Generally, the Hammett value of such a group is greater than 0.6. The Hammett value is a characterization of the charge affinity of a specific group and is a measure of an electron-withdrawing group (positive Hammett value) or an electron-donating group (negative Hammett value). The Hammett equation is described in more detail on pages 143-151 of Thomas H. Lowry and Katheleen Schueller Richardson, "Mechanism and Theory In Organic Chemistry", New York, 1987, and is hereby incorporated by reference. Such groups may include but are not limited to: triazinyl, pyrimidinyl, benzopyrimidinyl, benzopyridyl, phthalazinyl, phenanthrolinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, pyridazinyl, and the above groups substituted with alkyl or aryl.

[0029] Even more preferably, in the above formula I, formula (I-1), and formula (I-2), the Ar is selected from any one of the structures shown in the following formulas (3-1) to (3-4):

[0030]

[0031] In formula (3-1), the Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are each independently selected from CR 2or N atoms, and Z 1 , Z 2 , Z 3 , Z 4 and Z 5 At least one of them is a N atom,

[0032] In formula (3-2), Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 and Z 13 Each independently selected from CR 2 or N atoms, and Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 and Z 13 At least one of them is a N atom,

[0033] In formula (3-3), Z 14 , Z 15 , Z 16 , Z 17 , Z 18 , Z 19 , Z 20 , Z 21 , Z 22 and Z 23 Each independently selected from CR 2 or N atoms, and Z 14 , Z 15 , Z 16 , Z 17 , Z 18 , Z 19 , Z 20 , Z 21 , Z 22 and Z 23 At least one of them is a N atom,

[0034] In formula (3-4), Z 24 , Z 25 , Z 26 , Z 27 , Z 28 , Z 29 , Z 30 , Z 31 , Z 32 and Z 33 Each independently selected from CR 2 or N atoms, and Z 24 , Z25 , Z 26 , Z 27 , Z 28 , Z 29 , Z 30 , Z 31 , Z 32 and Z 33 at least one of them is an N atom;

[0035] Said R 2 is selected from one of hydrogen, halogen, cyano, nitro, hydroxy, C1-C10 linear alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 fused-ring aryl, C3-C30 monocyclic heteroaryl, C6-C30 fused-ring heteroaryl, or a combination of at least two of them;

[0036] wherein, * represents the bonding site of the group.

[0037] More preferably, said Ar has the structure shown in (3-1) or (3-2).

[0038] More preferably, in formula (3-1), at least two of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are N atoms; in formula (3-2), at least two of Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 and Z 13 are N atoms.

[0039] Furthermore, in the above formula I, formula (I-1), and formula (I-2), said Ar is selected from one of the following substituted or unsubstituted groups: pyridyl, quinolinyl, quinazolinyl, triazinyl, pyrimidinyl, or quinoxalinyl;

[0040] Preferably, said Ar is selected from one of the following substituted or unsubstituted groups: quinazolinyl, triazinyl, quinoxalinyl;

[0041] When the above-mentioned group has a substituent, the substituent is selected from the group consisting of halogen, cyano, nitro, hydroxyl, C1-C10 linear alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 fused-ring aryl, C3-C30 monocyclic heteroaryl, C6-C30 fused-ring heteroaryl, or a combination of at least two of them.

[0042] Furthermore, in the above formulas I, (I-1), and (I-2), the Ar is selected from one of the substituted or unsubstituted A1-A14 groups:

[0043]

[0044] Among them, * represents the bonding site of the group; when the above-mentioned group has a substituent, the substituent is selected from the group consisting of halogen, cyano, nitro, hydroxyl, C1-C10 linear alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 fused-ring aryl, C3-C30 monocyclic heteroaryl, C6-C30 fused-ring heteroaryl, or a combination of at least two of them.

[0045] Furthermore, in the above formulas I, (I-1), and (I-2), the Ar is selected from one of the B1-B19 groups:

[0046]

[0047] Among them, * represents the bonding site of the group.

[0048] More preferably, in the above formulas I, (I-1), and (I-2), the L is selected from a single bond or one of the following substituted or unsubstituted groups: phenylene, naphthylene, biphenylene; when the above-mentioned group has a substituent, the substituent is selected from the group consisting of halogen, cyano, nitro, hydroxyl, C1-C10 linear alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 fused-ring aryl, C3-C30 monocyclic heteroaryl, C6-C30 fused-ring heteroaryl, or a combination of at least two of them.

[0049] In this specification, the expression Ca-Cb means that the group has a carbon atom number of a-b. Generally speaking, unless otherwise specified, the carbon atom number does not include the carbon atom number of the substituent.

[0050] In this specification, the expression of a ring structure crossed by "—" indicates that the connection site is at any bond-forming position on the ring structure.

[0051] The heteroatoms in the present invention generally refer to atoms or atomic groups selected from N, O, S, P, Si, and Se, preferably selected from N, O, and S.

[0052] The atomic names described in the present invention include their corresponding various isotopes. For example, hydrogen (H) includes 1 H (protium or H), 2 H (deuterium or D), etc.; carbon (C) includes 12 C, 13 C, etc.

[0053] Among the above substituents, the number of carbon atoms in the C1-C10 linear alkyl group can be C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.; the number of carbon atoms in the C3-C10 cycloalkyl group can be C4, C5, C6, C7, C8, C9, C10, etc.; the number of carbon atoms in the C1-C10 alkoxy group can be C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.; the number of carbon atoms in the C1-C10 thioalkoxy group can be C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.; the number of carbon atoms in the C6-C30 monocyclic aryl group can be C6, C12, C14, C16, C18, C20, C26, C28, etc.; the number of carbon atoms in the C10-C30 polycyclic aryl group can be C10, C12, C14, C16, C18, C20, C26, C28, etc.; the number of carbon atoms in the C3-C30 monocyclic heteroaryl group can be C3, C4, C6, C8, C10, C12, C14, C16, C18, C20, C26, C28, etc.; the number of carbon atoms in the C6-C30 polycyclic heteroaryl group can be C6, C12, C14, C16, C18, C20, C26, C28, etc.

[0054] Further preferably, the substituent is selected from any one of C6-C30 monocyclic aryl groups, C10-C30 polycyclic aryl groups, C3-C30 monocyclic heteroaryl groups, and C6-C30 polycyclic heteroaryl groups, and specifically, it can be preferably phenyl, naphthyl, biphenyl, pyridyl, pyrimidinyl, quinolinyl, quinoxalinyl, quinazolinyl, dibenzofuranyl, dibenzothiophenyl, etc.

[0055] In this specification, C3-C10 cycloalkyl groups include monocyclic alkyl groups and polycyclic alkyl groups.

[0056] In this specification, the linear alkyl groups of C1 to C10 are preferably linear alkyl groups of C1 to C6, and examples thereof include methyl, ethyl, n-propyl, n-butyl, n-hexyl, n-octyl, isopropyl, isobutyl, tert-butyl, etc.

[0057] Furthermore, the following specific structural compounds can be preferably selected from the compounds of the general formula of the present invention, and these compounds are only representative:

[0058]

[0059]

[0060]

[0061]

[0062] The second object of the present invention is to provide an application of the compound described in the first object, and the compound is applied to an organic electronic device.

[0063] Preferably, the organic electronic device includes an organic light-emitting device, an optical sensor, a solar cell, a lighting element, an organic thin-film transistor, an organic field-effect transistor, an organic thin-film solar cell, an information tag, an electronic artificial skin sheet, a sheet-type scanner or an electronic paper, and preferably an organic light-emitting device.

[0064] Preferably, the compound is used as a host material for the light-emitting layer in the organic light-emitting device. More preferably, the compound is used as a red phosphorescent host material for the light-emitting layer in the organic light-emitting device.

[0065] The third object of the present invention is to provide an organic light-emitting device, which includes a substrate, a first electrode, a second electrode, and at least one organic layer located between the first electrode and the second electrode, and the organic layer contains at least one compound described in the first object.

[0066] Preferably, the organic layer includes a light-emitting layer, and the light-emitting layer contains at least one compound described in the first object.

[0067] Preferably, the compound is used as the host material for the light-emitting layer.

[0068] The specific reason why the compound of the present invention has excellent performance as a host material for the light-emitting layer is not yet clear, and it is speculated that the possible reasons are as follows:

[0069] The compound provided by the present invention uses indolocarbazole, where two nitrogen atoms substitute the 4,5 positions of carbazole to form a large conjugated ring, increasing the planarity and rigidity of the molecule, providing good hole transport properties, and matching with common electron transport groups to achieve carrier balance. Therefore, it can effectively improve the electron injection and migration efficiency in the device, thereby ensuring that the device obtains excellent effects of high luminous efficiency and low turn-on voltage.

[0070] In addition, the preparation process of the compound of the present invention is simple and easy to implement, and the raw materials are easily available, suitable for mass production and amplification. Detailed implementation manners

[0071] The technical solutions of the present invention will be further described below through specific implementation manners. Those skilled in the art should understand that the embodiments are only for helping to understand the present invention and should not be regarded as specific limitations to the present invention.

[0072] The representative synthesis method of the compound represented by general formula I-2 of the present invention is as follows:

[0073]

[0074] The substituents in the reaction formula are defined as in the general formula. By replacing different substituents, we can obtain the corresponding compounds.

[0075] The compounds of the synthesis methods not mentioned in the following synthesis examples of the present invention are all raw material products obtained through commercial channels. The solvents and reagents used in the present invention, such as chemical reagents like dichloromethane, ethanol, carbazole, quinazoline, quinoxaline, triazine, etc., can all be purchased from the domestic chemical product market, such as purchased from Sinopharm Chemical Reagent Co., Ltd., TCI Co., Ltd., Puyang Huicheng Co., Ltd., Shanghai Bide Pharmaceutical Co., Ltd., J&K Scientific Ltd., etc. In addition, those skilled in the art can also synthesize them through well-known methods.

[0076] Synthesis example 1

[0077] Synthesis of compound P9

[0078]

[0079] Add 4,5-dichlorocarbazole (100 mmol), 2-chloro-4-phenylquinazoline (110 mmol), potassium carbonate (150 mmol), and 200 mL of DMF into a reaction flask, heat to 150 °C and react for 4 h. Monitor the reaction by TLC until it is complete. After cooling, add it to water, filter and dry to obtain P9-A.

[0080] Add indolo[2,3-a]carbazole (30 mmol), P9-A (30 mmol), sodium tert-butoxide (100 mmol), Tris(dibenzylideneacetone)dipalladium Compound(1mmol), tri-tert-butylphosphine (2mmol) and 200mL of xylene were added to the reaction bottle, heated to 140°C for 12h, and the reaction was completed after TLC monitoring. After cooling, water and dichloromethane were added, the organic phase was separated, concentrated and purified by column chromatography to obtain compound P9.

[0081] Synthesis example 2

[0082] Synthesis of compound P13

[0083] The difference from Synthesis Example 1 is that 2-chloro-4-phenylquinazoline is replaced with an equal amount of 2-(4-fluorophenyl)-4-phenylquinazoline to obtain Compound P13.

[0084] Synthesis example 3

[0085] Synthesis of compound P17

[0086] The difference from Synthesis Example 1 is that 2-chloro-4-phenylquinazoline is replaced with an equal amount of 2-chloro-3-phenylquinoxaline to obtain Compound P17.

[0087] Synthesis example 4

[0088] Synthesis of compound P20

[0089] The difference from Synthesis Example 1 is that 2-chloro-4-phenylquinazoline is replaced with an equal amount of 2-chloro-3-(biphenyl-3-yl)quinoxaline to obtain Compound P20.

[0090] Synthesis example 5

[0091] Synthesis of compound P21

[0092] The difference from Synthesis Example 1 is that 2-chloro-4-phenylquinazoline is replaced with an equal amount of 2-chloro-4,6-diphenyl(1,3,5)triazine to obtain Compound P21.

[0093] Synthesis example 6

[0094] Synthesis of compound P27

[0095] The difference from Synthesis Example 1 is that 2-chloro-4-phenylquinazoline is replaced with an equal amount of 2-(2-fluorophenyl)-4,6-diphenyl(1,3,5)triazine to obtain Compound P27.

[0096] The present invention exemplifies the specific synthesis methods of the above compounds. For the compounds for which the specific synthesis methods are not given in the following embodiments, they are also prepared by similar methods, and only the raw materials need to be replaced, which will not be described here. Alternatively, those skilled in the art can also prepare them by other methods in the prior art.

[0097] To verify the certainty of the molecular structure of the compound of Formula I used in the embodiments of the present invention, we confirmed it by elemental analysis (Thermo Fisher FLASH 2000 CHNS / O organic elemental analyzer) and mass spectrometry information (ZAB-HS type mass spectrometer manufactured by Micromass UK). The results are shown in Table 1.

[0098] The present invention exemplarily gives the specific synthesis methods of the above several compounds. For the compounds without specific synthesis methods in the following embodiments, they are also prepared by similar methods, and can be obtained only by replacing the raw materials, which will not be elaborated here. Or those skilled in the art can also prepare them by other methods in the prior art.

[0099] To verify the certainty of the molecular structure of the compound of Formula I used in the embodiments of the present invention, we confirmed it by elemental analysis (Thermo Fisher FLASH 2000 CHNS / O organic elemental analyzer) and mass spectrometry information (ZAB-HS type mass spectrometer manufactured by Micromass UK). The results are shown in Table 1.

[0100] Table 1:

[0101] Compound Elemental analysis (%) Mass spectrometry (M / Z) P9 C, 84.74; H, 4.05; N, 11.21 623.21 P13 C, 85.80; H, 4.19; N, 10.02 699.24 P17 C, 84.74; H, 4.03; N, 11.23 623.21 P20 C, 85.83; H, 4.18; N, 10.00 699.24 P21 C, 83.05; H, 4.02; N, 12.93 650.22 P27 C, 84.28; H, 4.17; N, 11.55 726.25

[0102] Device Example

[0103] Embodiment

[0104] The OLED includes a first electrode and a second electrode, and an organic material layer located between the electrodes. The organic material can be further divided into multiple regions. For example, the organic material layer can include a hole transport region, a light-emitting layer, and an electron transport region.

[0105] In a specific embodiment, a substrate can be used under the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a thin film transistor (TFT) can also be provided on the substrate for a display.

[0106] The first electrode can be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, oxide transparent conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), and any combination thereof can be used. When the first electrode is used as a cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof can be used.

[0107] The organic material layer can be formed on the electrode by methods such as vacuum thermal evaporation, spin coating, printing, etc. The compounds used as the organic material layer can be organic small molecules, organic macromolecules, polymers, and combinations thereof.

[0108] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multi-layer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); where the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer.

[0109] The materials of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers, or polymers containing conductive dopants such as poly(phenylene vinylene), polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives such as the compounds shown as HT-1 to HT-51 below; or any combination thereof.

[0110]

[0111]

[0112]

[0113] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can adopt one or more of the above-mentioned compounds of HT-1 to HT-51, or one or more of the following compounds of HI-1 - HI-3; it can also adopt one or more of the compounds of HT-1 to HT-51 doped with one or more of the compounds of HI-1 - HI-3.

[0114]

[0115] The light-emitting layer includes light-emitting dyes (i.e., dopants) that can emit spectra of different wavelengths, and may also include a host material at the same time. The light-emitting layer can be a monochromatic light-emitting layer that emits a single color such as red, green, or blue. Monochromatic light-emitting layers of multiple different colors can be arranged in a planar pattern according to a pixel pattern, or stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

[0116] According to different technologies, the light-emitting layer material can be a fluorescent electroluminescent material, a phosphorescent electroluminescent material, a thermally activated delayed fluorescence light-emitting material, or other different materials. In an OLED device, a single light-emitting technology can be adopted, or a combination of multiple different light-emitting technologies can be adopted. These different light-emitting materials classified by technology can emit light of the same color or light of different colors.

[0117] In one aspect of the present invention, the light-emitting layer adopts the technology of phosphorescent electroluminescence. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of RPD-1 to RPD-28 listed below.

[0118]

[0119]

[0120] In one aspect of the present invention, an electron blocking layer (EBL) is located between the hole transport layer and the light-emitting layer. The electron blocking layer can be made of, but not limited to, one or more of the above compounds HT-1 to HT-51, or made of, but not limited to, one or more of the following compounds PH-47 to PH-77; it can also be made of a mixture of one or more of the compounds HT-1 to HT-51 and one or more of the compounds PH-47 to PH-77.

[0121]

[0122]

[0123] The OLED organic material layer may also include an electron transport region between the light-emitting layer and the cathode. The electron transport region can be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region can also be a multi-layer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0124] In one aspect of the present invention, the electron transport layer material may be selected from, but not limited to, one or more combinations of ET-1 to ET-65 listed below.

[0125]

[0126]

[0127]

[0128] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may be formed of, but not limited to, one or more compounds selected from the above ET-1 to ET-65, or one or more compounds selected from the following PH-1 to PH-46; it may also be a mixture of one or more compounds selected from ET-1 to ET-65 and one or more compounds selected from PH-1 to PH-46.

[0129]

[0130]

[0131] The device may further include an electron injection layer located between the electron transport layer and the cathode, and the electron injection layer material includes, but is not limited to, one or more combinations listed below.

[0132] LiQ, LiF, NaCl, CsF, Li 2 O, Cs 2 CO 3 , BaO, Na, Li, Ca, Mg.

[0133] Device Example 1:

[0134] Provide an organic electroluminescent device, and the specific preparation method is as follows:

[0135] Ultrasonically treat the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, rinse it in deionized water, ultrasonically degrease it in an acetone:ethanol mixed solvent, bake it in a clean environment until all moisture is completely removed, clean it with ultraviolet light and ozone, and bombard the surface with a low-energy cation beam;

[0136] Place the glass substrate with the anode in a vacuum chamber and evacuate to <1×10 -5Pa, a 10-nm mixture of HT-4:HI-3 (97 / 3, w / w) was vacuum thermally evaporated in sequence on the above-mentioned anode layer film as the hole injection layer, 60 nm of compound HT-4 as the hole transport layer, 5 nm of compound HT-48 as the electron blocking layer; 40 nm of a binary mixture of compound P-9:RPD-10 (100:3, w / w) as the light-emitting layer; 5 nm of ET-23 as the hole blocking layer, 25 nm of a mixture of compound ET-61:ET-57 (50 / 50, w / w) as the electron transport layer, 1 nm of LiF as the electron injection layer, and 150 nm of metallic aluminum as the cathode. The total evaporation rate of all organic layers and LiF was controlled at 0.1 nm / second, and the evaporation rate of the metal electrode was controlled at 1 nm / second.

[0137] Device Examples 2 to 6 were fabricated using the same method as Device Example 1, except that the compound P9 of the present invention as the host material of the light-emitting layer was replaced with the compounds P13, P17, P20, P21, and P27 of the present invention, respectively.

[0138] Device Comparative Example 1 was fabricated using the same method as Device Example 1, except that the compound P9 of the present invention as the host material of the light-emitting layer was replaced with the compound C1 in the prior art.

[0139] The structure of C1 is as follows:

[0140]

[0141] Among them, C1 is detailed in Patent Application KR1020190007792A.

[0142] Testing method of the device (including equipment and testing conditions):

[0143] The following performance measurements were performed on the organic light-emitting devices prepared by the above process:

[0144] At the same brightness, the driving voltage and current efficiency of the organic light-emitting devices prepared in Examples 1 to 6 and Comparative Example 1 were measured using a digital source meter and a luminance meter. Specifically, the voltage was increased at a rate of 0.1 V per second, and the voltage when the brightness of the organic light-emitting device reached 1000 cd / m 2 was measured as the driving voltage, and the current density at this time was also measured; the ratio of brightness to current density is the current efficiency.

[0145] The performance of the organic light-emitting devices is shown in Table 2 below.

[0146] Table 2:

[0147]

[0148] As can be seen from Table 1, when the material schemes and preparation processes of other functional layers in the organic electroluminescent device structure are exactly the same, compared with the comparative examples, the organic electroluminescent devices provided by Examples 1-6 of the present invention have higher current efficiency and lower driving voltage.

[0149] The above experimental results show that the novel organic material of the present invention is used in the organic electroluminescent device, enabling the device to have both a lower driving voltage and a higher current efficiency.

[0150] The above experimental data show that the novel organic material of the present invention as the light-emitting layer material of the organic electroluminescent device is a red light host material with good performance and has broad application prospects.

[0151] The present invention uses the above embodiments to illustrate the detailed method of the present invention, but the present invention is not limited to the above detailed method, that is, it does not mean that the present invention must rely on the above detailed method to be implemented. Those skilled in the art should understand that any improvement of the present invention, the equivalent substitution of each raw material of the product of the present invention, the addition of auxiliary components, the selection of specific methods, etc. all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A general formula compound has the structure shown in Formula I-2; In Formula I-2, the Ar is selected from any one of the structures shown in the following Formulas (3-1) to (3-4): In formula (3-1), the Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently selected from a CR 2 or an N atom, and at least one of Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 is an N atom, In formula (3-2), the Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 and Z 13 are each independently selected from a CR 2 or an N atom, and at least one of Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 and Z 13 is an N atom. In formula (3-3), the said Z 14 、Z 15 、Z 16 、Z 17 、Z 18 、Z 19 、Z 20 、Z 21 、Z 22 and Z 23 are each independently selected from a CR 2 or an N atom, and at least one of Z 14 、Z 15 、Z 16 、Z 17 、Z 18 、Z 19 、Z 20 、Z 21 、Z 22 and Z 23 is an N atom, In formula (3-4), Z 24 、Z 25 、Z 26 、Z 27 、Z 28 、Z 29 、Z 30 、Z 31 、Z 32 and Z 33 are each independently selected from CR 2 or an N atom, and at least one of Z 24 、Z 25 、Z 26 、Z 27 、Z 28 、Z 29 、Z 30 、Z 31 、Z 32 and Z 33 is an N atom, The R 2 is selected from one or a combination of at least two of hydrogen, halogen, cyano, nitro, hydroxy, C1-C10 linear alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 fused-ring aryl, C3-C30 monocyclic heteroaryl, and C6-C30 fused-ring heteroaryl; Wherein, * represents the bonding site of the group; In Formula I-2, the L is selected from a single bond or an arylene group having 6 to 30 carbon atoms; In Formula I-2, the X 1 -X 16 are each independently selected from CR 1 wherein the R 1 is independently selected from hydrogen, halogen, cyano, nitro, hydroxy, C1-C10 linear alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 fused-ring aryl, C3-C30 monocyclic heteroaryl, C6-C30 fused-ring heteroaryl, or a combination of at least two thereof.

2. The compound according to claim 1, in formula I-2, said X 1 -X 16 are each independently selected from CR 1 , said R 1 is hydrogen.

3. The compound according to claim 1, wherein the Ar has the structure shown in (3-1) or (3-2).

4. The compound according to claim 1, in formula (3-1), Z 1 , Z 2 , Z 3 , Z 4 and Z 5 at least two of them are N atoms; In formula (3-2), Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , and Z 13 at least two of them are N atoms.

5. The compound according to claim 1, in the above Formula (Ⅰ-2): The Ar is selected from one of the following substituted or unsubstituted groups: pyridyl, quinolinyl, quinazolinyl, triazinyl, pyrimidinyl or quinoxalinyl; When the Ar has a substituent, the substituent is selected from halogen, cyano, nitro, hydroxyl, C1-C10 linear alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 polycyclic aryl, C3-C30 monocyclic heteroaryl, C6-C30 polycyclic heteroaryl, or a combination of at least two of them.

6. The compound according to claim 1, in the above Formula (Ⅰ-2): The Ar is selected from one of the following substituted or unsubstituted groups: quinazolinyl, triazinyl, quinoxalinyl; When the Ar has a substituent, the substituent is selected from halogen, cyano, nitro, hydroxyl, C1-C10 linear alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 polycyclic aryl, C3-C30 monocyclic heteroaryl, C6-C30 polycyclic heteroaryl, or a combination of at least two of them.

7. The compound according to claim 1, in the above Formula (Ⅰ-2): The Ar is selected from one of the substituted or unsubstituted groups A1 to A14: Wherein, * represents the bonding site of the group; When the above group has a substituent, the substituent is selected from halogen, cyano, nitro, hydroxyl, C1-C10 linear alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 polycyclic aryl, C3-C30 monocyclic heteroaryl, C6-C30 polycyclic heteroaryl, or a combination of at least two of them.

8. The compound according to claim 1, in the above Formula (Ⅰ-2): The Ar is selected from one of the groups B1 to B19: Wherein, * represents the bonding site of the group.

9. The compound according to claim 1, in the above Formula (Ⅰ-2), the L is selected from a single bond or one of the following groups: phenylene, naphthylene, biphenylene.

10. The compound according to claim 1, the compound has the structure shown below:

11. Use of the compound according to any one of claims 1-10 as a functional material in an organic electronic device, wherein the organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet-type scanner or an electronic paper.

12. Use of the compound according to any one of claims 1-10 as a host material for a light-emitting layer in an organic electroluminescent device.

13. An organic electroluminescent device, comprising a first electrode, a second electrode and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer includes a hole transport region, a light-emitting layer, and an electron transport region, the hole transport region is formed on the anode layer, the cathode layer is formed on the electron transport region, and the light-emitting layer is located between the hole transport region and the electron transport region; wherein, the light-emitting layer contains the compound according to any one of claims 1-10.

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