A compound and application thereof, an organic electroluminescent device comprising the same

Abstract

The present application relates to an organic compound, belongs to organic luminescent material technical field, and simultaneously relates to the application of the compound and the organic electroluminescent device containing the compound.The organic compound has the structure shown as formula I.The compound provided by the present application is a main body material containing large condensed ring, has good transmission performance and stability, and when applied to the OLED device, can effectively improve the service life of the device.

Description

TECHNICAL FIELD

[0001] The present application relates to a kind of compound, belong to organic luminescent material technical field, simultaneously, it relates to the application of the compound and the organic electroluminescent device comprising it. BACKGROUND

[0002] In recent years, optoelectronic devices based on organic materials have developed rapidly and become a hot spot in the field. Examples of such organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic photovoltaic cells, organic sensors, and the like. Among them, OLEDs have developed particularly rapidly and have achieved commercial success in the field of information display. OLEDs can provide high saturation of red, green, and blue colors, and full-color display devices made with them do not require additional backlights, have vivid colors, and are lightweight, flexible, and other advantages.

[0003] The core of an OLED device is a multi-layer thin film structure containing various functional organic materials. Commonly used functional organic materials include hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light-emitting host materials and light-emitting guests (dyes), etc. When powered on, electrons and holes are injected and transported to the light-emitting region and recombine there, generating excitons and emitting light.

[0004] 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 utilize both triplet and singlet excitons for light emission, and are called phosphorescent emitters, which can improve energy conversion efficiency by up to four times compared to traditional fluorescent emitters. Thermal activation delayed fluorescence (TADF) technology promotes the conversion of triplet excitons to singlet excitons, effectively utilizing triplet excitons without using metal complexes to achieve high light-emitting efficiency. Thermal activation sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize emitters through energy transfer, also achieving high light-emitting efficiency.

[0005] Although products using OLED display technology have been commercialized, there is still a need to continuously improve the performance of devices such as lifetime and efficiency to meet people's pursuit of higher quality. Therefore, there is an urgent need in the art to develop more types of organic materials for use in organic electroluminescent devices to enable the devices to have high light-emitting efficiency, low driving voltage, and long service life. SUMMARY

[0006] In view of the deficiencies of the prior art, one of the purposes of the present application is to provide a kind of compound. The compound has good photoelectric performance when applied to OLED devices.

[0007] To achieve the above object, the present application adopts the following technical solution:

[0008] The present application provides a compound having the structure shown in Formula I:

[0009]

[0010] In Formula I, Y and Z are each independently selected from O, S, NR 1 , CR 2 R 3 .

[0011] R 1 is selected from one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C12-C36 arylamino, and substituted or unsubstituted C3-C30 heteroarylamino;

[0012] R 2 and R 3 are each independently selected from one of substituted or unsubstituted C1-C18 chain alkyl, substituted or unsubstituted C3-C20 cyclic alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, and R 2 and R 3 may be connected to form a ring;

[0013] X1-X 13 are each independently selected from CH, CR 4 , or N, R 4 is selected from one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C12-C36 arylamino, and substituted or unsubstituted C3-C30 heteroarylamino, and when R 4 is a plurality, adjacent R 4 do not form a ring;

[0014] When the above-mentioned substituted or unsubstituted groups have a substituent group, the substituent group is selected from one or a combination of two of deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde, ketone, ester, carbonyl, C1-C30 chain alkyl, C1-C30 alkoxy, C3-C20 cyclic alkyl, C3-C20 heterocyclic alkyl, C6-C60 aryl, C6-C60 fused ring aryl, C3-C60 heteroaryl, and C3-C60 fused ring heteroaryl.

[0015] Preferably, Y is NR 1 .

[0016] Further preferably, Z is O, S, or NR1 .

[0017] In the present application, the "substituted or unsubstituted" group can be substituted with one substituent or can be substituted with a plurality of substituents, and when the substituents are a plurality, they can be selected from different substituents. When the same expression is used in the present application, it has the same meaning, and the selection range of the substituents is as described above and will not be described again.

[0018] In the present specification, the expression of Ca~Cb represents that the number of carbon atoms of the group is a~b, and unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms of the substituents.

[0019] In the present specification, "each independently" means that when the subject has a plurality, they can be the same or different.

[0020] In the present application, the expression of a chemical element, unless otherwise specified, generally includes the concept of its isotope, for example, the expression of "hydrogen (H)" includes the concept of its isotope 1 H (protium or H), 2 H (deuterium or D); carbon (C) includes 12 C, 13 C, and the like, and will not be described again.

[0021] In the present application, the heteroatom in the heteroaryl group generally refers to an atom or atom group selected from N, O, S, P, Si, and Se, preferably N, O, and S.

[0022] In the present specification, as examples of halogen, fluorine, chlorine, bromine, iodine, and the like can be given.

[0023] In the present application, the substituted or unsubstituted C6-C60 aryl group includes monocyclic aryl groups and fused ring aryl groups, preferably C6-C30 aryl groups, and further preferably C6-C20 aryl groups. The monocyclic aryl group refers to a group having at least one phenyl group in the molecule, and when there are at least two phenyl groups in the molecule, the phenyl groups are independent of each other and connected by a single bond, and exemplary examples are phenyl, biphenyl, terphenyl, and the like. Specifically, the biphenyl includes 2-biphenyl, 3-biphenyl, and 4-biphenyl; and the terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, and m-terphenyl-2-yl. The fused ring aryl group refers to a group having at least two aromatic rings in the molecule, and the aromatic rings are not independent of each other but share two adjacent carbon atoms and are fused to each other. Exemplary examples are naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, fluoranthene, triphenylene, pyrenyl, perylenyl, The naphthyl group includes 1-naphthyl or 2-naphthyl; the anthryl group is selected from 1-anthryl, 2-anthryl and 9-anthryl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracenyl group is selected from 1-tetracenyl, 2-tetracenyl and 9-tetracenyl. The derivative group of fluorene is selected from 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, 9,9'-spirobifluorene and benzofluorenyl.

[0024] In the present application, the substituted or unsubstituted C3-C60 heteroaryl group includes monocyclic heteroaryl group and fused ring heteroaryl group, preferably C3-C30 heteroaryl group, further preferably C4-C20 heteroaryl group, and more preferably C5-C12 heteroaryl group. The monocyclic heteroaryl group means a group having at least one heteroaryl group in the molecule, and when the molecule has one heteroaryl group and other groups (e.g., aryl group, heteroaryl group, alkyl group, etc.), the heteroaryl group and the other groups are connected independently of each other by a single bond. Examples of the monocyclic heteroaryl group include furyl group, thienyl group, pyrrolyl group, pyridyl group, etc. The fused ring heteroaryl group means a group having at least one aromatic heterocyclic ring and one aromatic ring (aromatic heterocyclic ring or aromatic ring) in the molecule, and the two rings are fused to each other by sharing two adjacent atoms. Examples of the fused ring heteroaryl group include benzofuranyl group, benzothienyl group, isobenzofuranyl group, indolyl group, dibenzofuranyl group, dibenzothienyl group, carbazolyl group, acridinyl group, isobenzofuranyl group, isobenzothienyl group, benzocarbazolyl group, azacarbazolyl group, phenothiazinyl group, phenoxazinyl group, 9-phenylcarbazolyl group, 9-naphthylcarbazolyl group, dibenzocarbazolyl group, indolocarbazolyl group, etc.

[0025] In the present application, the C12-C36 arylamino group represents a group in which one or both hydrogens of the C12-C36 arylamino group are replaced by C12-C36 aryl group. The C12-C36 arylamino group can be connected to the aryl group of the arylamino group or to the N of the arylamino group. Examples of the C12-C36 arylamino group include phenylamino group, methylphenylamino group, naphthylamino group, phenanthrylamino group, biphenylamino group, etc.

[0026] In the present application, the C3-C30 heteroarylamino group is the same as the C12-C36 arylamino group. Examples of the C3-C30 heteroarylamino group include carbazolylamino group, dibenzothienylamino group, dibenzofuranylamino group, etc.

[0027] The chain alkyl mentioned in the present application includes straight chain alkyl and branched chain alkyl if not otherwise specified. Specifically, the substituted or unsubstituted C1-C30 chain alkyl, preferably the substituted or unsubstituted C1-C16 chain alkyl, more preferably the substituted or unsubstituted C1-C10 chain alkyl. The substituted or unsubstituted C3-C30 cycloalkyl, preferably the substituted or unsubstituted C3-C20 cycloalkyl, more preferably the substituted or unsubstituted C3-C10 cycloalkyl, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, n-hexyl, n-octyl, i-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, t-amyl, cyclohexyl, adamantyl, etc.

[0028] Further, the R 1 and R 4 are each independently selected from the group consisting of substituted or unsubstituted phenyl, naphthyl, anthryl, phenanthryl, indenyl, fluoranthene, triphenylene, pyrene, perylene, phenanthrene, 2-biphenyl, 3-biphenyl, 4-biphenyl, 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirofluorenyl and benzofluorenyl, furanyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothienyl, acridinyl, pyridyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, phenoxazinyl, phenylamino, methylphenylamino, naphthylamino, anthrylamino, phenanthrylamino, biphenylamino, carbazolylamino, dibenzothienylamino, dibenzofuranylamino;

[0029] Each of the above-mentioned substituted or unsubstituted groups has a substituent selected from one or a combination of at least two of deuterium, halogen, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl when the group has a substituent.

[0030] Further, the R 2 , R 3 are each independently selected from the group consisting of substituted or unsubstituted methyl, ethyl, n-propyl, i-propyl, n-butyl, n-hexyl, n-octyl, i-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, anthryl, phenanthryl, indenyl, fluoranthene, triphenylene, pyrene, perylene, one of the following groups: deuterium, halogen, C1-C10 linear alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, or a combination of at least two of them.

[0031] When the above-mentioned each group with or without substitution has a substituent, the substituent is selected from one of the following groups: deuterium, halogen, C1-C10 linear alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, or a combination of at least two of them.

[0032] The design point of the present application is to provide a large planar mother nucleus (as shown in general formula I) structure, while breaking the conjugation of the molecule through O, S, CR 2 R 3 or N, so that the molecule can maintain a high triplet energy level T1 while increasing the planar structure, meeting the energy level requirements of the host material. The large planar structure is beneficial to the transport of carriers, so that the material of the present application has good injection and transport capacity. The performance embodied in the device is lower voltage and higher efficiency.

[0033] Further, the general compound of the present application is preferably the following specific compounds, but the present application is not limited to the specific compounds shown below:

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052] As another aspect of the present application, there is also provided a use of the compound as described above in an organic electroluminescent device. Specifically, the use as a light-emitting layer material in an organic electroluminescent device is preferred, and the use in a red organic electroluminescent device is more preferred.

[0053] More preferably, the compound according to the present application is used as a host material of the organic electroluminescent device, preferably as a red host material.

[0054] In addition to the organic electroluminescent device, the compound according to the present application can be applied to a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet-type scanner, or an electronic paper.

[0055] As still another aspect of the present application, there is also provided an organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode, characterized in that the organic layer contains the compound of Formula I as described above, or contains a compound having a structure represented by at least one of P1 to P241 as described above.

[0056] In particular, one embodiment of the present application provides an organic electroluminescent device, comprising a substrate, and a first electrode, a plurality of light-emitting functional layers and a second electrode formed in sequence on the substrate; the light-emitting functional layers comprise a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is between the hole transport layer and the electron transport layer; wherein the light-emitting layer comprises a host material and a dopant material, the host material comprises at least one compound represented by the formula I as described above, or a compound containing a structure represented by at least one of P1 to P241 as described above.

[0057] The present application also discloses a display screen or display panel, wherein the organic electroluminescent device as described above is used in the display screen or display panel; as a preferred embodiment, the display screen or display panel is an OLED display.

[0058] The present application also discloses an electronic device, wherein the electronic device has a display screen or display panel, and the display screen or display panel uses the organic electroluminescent device as described above. DETAILED DESCRIPTION

[0059] The technical solutions of the present application are further described below through specific embodiments. It should be understood by those skilled in the art that the embodiments are only used to help understand the present application, and should not be regarded as specific limitations of the present application.

[0060] The mass spectrometry characterization data in the following synthesis examples are obtained by using a ZAB-HS mass spectrometer manufactured by Micromass Company in the United Kingdom.

[0061] The compound of the present application can be obtained through the following general reaction:

[0062]

[0063] wherein M represents a functional group required for synthesizing Y ring, such as nitro group, mercapto group, hydroxyl group, alcohol functional group, etc.

[0064] The synthesis route of the specific intermediate is as follows:

[0065] Synthesis of M1

[0066]

[0067] Into a flask, 10-(2-bromophenyl)-10H-phenoxazine (0.1 mol), bis(pinacolato)diboron (0.12 mol), potassium acetate (0.15 mol), [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride (0.001 mol), dioxane 300 ml, reflux for 6 h, TLC monitor the reaction complete after cooling, add water and dichloromethane extraction, the organic phase concentrated after column chromatography purification of A.

[0068] Into a flask, A (0.08 mol), 2-chloro-3-bromonitrobenzene (0.08 mol), potassium carbonate (0.1 mol), tetrakis(triphenylphosphine) palladium (0.0008 mol), water 50 ml, dioxane 200 ml, 80 °C for 5 h, TLC monitor the reaction complete after adding water and ethyl acetate extraction, the organic phase concentrated after methanol washed after filtration of the intermediate B.

[0069] Into a flask, intermediate B (0.05 mol), potassium carbonate (0.1 mol), palladium acetate (0.0025 mol), tricyclohexylphosphine (0.005 mol), N, N-dimethylacetamide (150 ml), heated to 150 °C for 3 h, TLC monitor the reaction complete, the reaction was cooled after pouring into water, filter cake was washed with methanol after the intermediate C.

[0070] Into a flask, intermediate C (0.03 mol), triphenylphosphine (0.09 mol), o-dichlorobenzene (100 ml) heated to reflux for 4 h, TLC monitor the reaction complete directly reduced pressure to remove the solvent, column chromatography purification of intermediate M1. (MS = 347.11)

[0071] Synthesis of M2

[0072] Synthesis of M2 is the same as M1, except that 10-(2-bromophenyl)-10H-phenoxazine is replaced by the same mass of 10-(2-bromophenyl)-10H-phenothiazine, the intermediate M2. (MS = 363.09)

[0073]

[0074] Synthesis of M3

[0075] Synthesis of M3 is the same as M1, except that 10-(2-bromophenyl)-10H-phenoxazine is replaced by the same mass of 10-(2-bromophenyl)-9,9-dimethylacridine, the intermediate M2. (MS = 373.16)

[0076]

[0077] Synthesis of M4

[0078]

[0079] Into a reaction flask was placed 10-(2-bromophenyl)-10H-phenoxazine (0.1 mol), bis(pinacolato)diboron (0.12 mol), potassium acetate (0.15 mol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (0.001 mol), dioxane 300 ml, and the mixture was refluxed for 6 h. After the reaction was completed, the mixture was cooled, water and dichloromethane were added, and the organic phase was concentrated and purified by column chromatography to obtain A.

[0080] Into a reaction flask was placed A (0.08 mol), 2-chloro-3-bromothioanisole (0.08 mol), potassium carbonate (0.1 mol), tetrakis(triphenylphosphine)palladium (0.0008 mol), water 50 ml, dioxane 200 ml, and the mixture was refluxed at 80°C for 5 h. After the reaction was completed, water and ethyl acetate were added, and the organic phase was concentrated and washed with methanol, and then filtered to obtain intermediate B.

[0081] Into a reaction flask was placed intermediate B (0.05 mol), potassium carbonate (0.1 mol), palladium acetate (0.0025 mol), tricyclohexylphosphine (0.005 mol), and N,N-dimethylacetamide (150 ml), and the mixture was heated to 150°C and reacted for 3 h. After the reaction was completed, the reaction solution was cooled, poured into water, and the filter cake was washed with methanol to obtain intermediate C.

[0082] Into a reaction flask was placed intermediate C (0.03 mol), 34.5% hydrogen peroxide (0.045 mol), acetic acid (50 ml), and tetrahydrofuran 100 ml, and the mixture was reacted at room temperature for 24 h. After the reaction was completed, the solvent was removed under reduced pressure, the organic phase was extracted with dichloromethane and aqueous sodium bicarbonate solution, concentrated, and purified by column chromatography to obtain intermediate D.

[0083] Into a reaction flask was placed intermediate D (0.03 mol) and trifluoromethanesulfonic acid (100 ml), and the mixture was reacted at room temperature for 48 h. After the reaction was completed, 30 ml of pyridine and 1 mol / L aqueous sodium hydroxide solution were added at 0°C to adjust the pH to 6-7, and the mixture was heated to 100°C and reacted for 1 h. The mixture was directly filtered, and the filter cake was purified by column chromatography to obtain intermediate M4 (MS, 364.08).

[0084] Synthesis of M5

[0085] The synthesis of M5 was the same as that of M4, except that 10-(2-bromophenyl)-10H-phenoxazine was replaced by 10-(2-bromophenyl)-10H-phenothiazine in an equal amount to obtain intermediate M5 (MS, 380.05).

[0086]

[0087] Synthesis of M6

[0088]

[0089] Synthesis of S: 0.2 mol of 5,10-dihydro-5-phenylphenazine, o-bromoidobenzene 0.2 mol, cuprous iodide 0.04 mol, o-phenanthroline 0.08 mol, potassium phosphate 0.3 mol, toluene were added into a reaction bottle, and refluxed for 8 h. After monitoring the completion of the reaction, the filtrate was directly concentrated and purified by column chromatography to obtain the intermediate S.

[0090] Synthesis of M6 was the same as M1, except that 10-(2-bromophenyl)-10H- phenoxazine was replaced by the same amount of S to obtain the intermediate M6 (MS, 422.16).

[0091] Synthesis Example 1

[0092] Synthesis of compound P9

[0093]

[0094] M1 (0.05 mol), 3-bromo-1,1':2',1"-terphenyl (0.06 mol), sodium tert-butoxide (0.1 mol), tris(dibenzylideneacetone)dipalladium (0.0005 mol), tri-tert-butylphosphine (0.001 mol), and xylene (200 ml) were added into a reaction bottle, heated to 140°C and reacted for 5 h. After the reaction was completed by TLC monitoring, water and dichloromethane were added after cooling, and the organic phase was concentrated and purified by column chromatography to obtain P9 (MS, 575.20).

[0095] The synthesis methods of the following synthesis examples 2-6 were the same as synthesis example 1, except that the raw materials in synthesis example 1 were replaced by the same amount of raw materials in Table 1 below.

[0096] Table 1:

[0097]

[0098]

[0099] Synthesis Example 7

[0100] Synthesis of compound P43

[0101]

[0102] M2 (0.05 mol), 2-chloro-4-phenylquinazoline (0.07 mol), potassium carbonate (0.1 mol) were added into 200 ml of N,N-dimethylformamide, heated to 140°C for 4 h, after the reaction was completed, it was cooled to room temperature, poured into water, and the filter cake was purified by column chromatography to obtain P43 (MS, 551.18).

[0103] The following synthesis examples 8 to 18 have the same synthesis method as synthesis example 7, except that the raw material in synthesis example 7 is replaced with the same amount of raw material in Table 2 below.

[0104] Table 2:

[0105]

[0106]

[0107]

[0108]

[0109] Synthesis example 19:

[0110] Synthesis of compound P108

[0111]

[0112] M4 (0.1 mol) was added into 400 ml of tetrahydrofuran, cooled to -78°C, and 2.5 mol / L of n-butyllithium (0.12 mol) was added dropwise. After 30 min of incubation, isopropyl alcohol pinacol ester (0.15 mol) was added dropwise, and the reaction was gradually recovered to room temperature. Water and ethyl acetate were added for extraction, and the organic phase was concentrated and washed with methanol to obtain intermediate P108-A.

[0113] P108-A (0.03 mol), 4-bromo-N-(4-(naphthalen-2-yl)phenyl)-N-phenylamine (0.03 mol), potassium carbonate (0.05 mol), tetrakis(triphenylphosphine)palladium (0.0005 mol), 30 ml of water, and 200 ml of dioxane were refluxed under nitrogen protection for 5 h. After the reaction was completed, water and dichloromethane were added for separation, and the organic phase was concentrated and purified by column chromatography to obtain P108 (MS, 733.22).

[0114] Synthesis example 20:

[0115] Synthesis of compound P222

[0116]

[0117] The difference from Synthesis Example 19 is that M4 is replaced with an equal amount of M5, and 4-bromo-N-(4-(naphthalen-2-yl)phenyl)-N-phenylamine is replaced with an equal amount of N-phenyl-3-bromocarbazole to obtain compound P222 (MS, 621.14).

[0118] The present application exemplarily gives the above several compounds specific synthesis method, for the following examples in which the specific synthesis method is not given compounds, also by similar method preparation and obtained, only need to replace the raw material can be obtained, hereinafter will not be repeated, or those skilled in the art can also use other ways in the prior art to prepare.

[0119] Device embodiments

[0120] The OLED includes a first electrode and a second electrode, and an organic material layer 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.

[0121] In specific embodiments, a substrate can be used under the first electrode or on the second electrode. The substrate is a glass or a polymer material that has excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, the substrate can also have a thin film transistor (TFT) for display.

[0122] The first electrode can be formed by sputtering or depositing a material used as the first electrode on a substrate. When the first electrode is used as an anode, an oxide transparent conductive material 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, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof can be used.

[0123] The organic functional layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer can be an organic small molecule, an organic macromolecule, and a polymer, and a combination thereof.

[0124] The hole transport region is between the anode and the light emitting layer. The hole transport region can be a single layer structure of a 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); wherein the HIL is between the anode and the HTL, and the EBL is between the HTL and the light emitting layer.

[0125] The material of the hole transport layer can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or conductive dopant-containing polymers such as polyphenylene vinylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphor sulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, wherein the aromatic amine derivatives include compounds as shown in HT-1 to HT-50 below; or any combination thereof.

[0126]

[0127]

[0128]

[0129] 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 employ one or more compounds of HT-1 to HT-50 described above, or employ one or more compounds of HI-1 to HI-3 described below; or employ one or more compounds of HT-1 to HT-50 doped with one or more compounds of HI-1 to HI-3 described below.

[0130]

[0131] The light-emitting layer includes light-emitting dyes (i.e., dopants) that can emit different wavelengths of light spectrum, and can also include host materials. The light-emitting layer can be a single-color light-emitting layer that emits a single color such as red, green, blue, etc. Multiple single-color light-emitting layers of different colors can be arranged in a planar pattern according to a pixel pattern, or can be stacked together to form a color light-emitting layer. When the 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 emit different colors such as red, green, blue, etc. at the same time.

[0132] Depending on the different technologies, the light-emitting layer material can employ different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, thermally activated delayed fluorescence light-emitting materials, etc. In an OLED device, a single light-emitting technology can be employed, or a combination of multiple different light-emitting technologies can be employed. These different light-emitting materials classified by technology can emit the same color of light, or can emit different colors of light.

[0133] In one aspect of the present application, the light-emitting layer employs phosphorescent electroluminescent technology. 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.

[0134]

[0135] The electron transport zone can be a single layer structure of an 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 zone 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).

[0136] In one aspect of the present application, the electron transport layer material can be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0137]

[0138]

[0139]

[0140]

[0141] The device can also include an electron injection layer between the electron transport layer and the cathode, and the electron injection layer material includes, but is not limited to, one or more combinations of the following.

[0142] Liq, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Yb.

[0143] The cathode is a magnesium-silver mixture, LiF / Al, ITO and other metals, metal mixtures, oxides.

[0144] Example 1

[0145] In this embodiment, the process of preparing an organic electroluminescent device is as follows:

[0146] The glass plate coated with ITO transparent conductive layer is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixture of acetone and ethanol solvent, baked in a clean environment until the water is completely removed, cleaned with ultraviolet light and ozone, and the surface is bombarded with low-energy cation beams;

[0147] The above glass substrate with ITO anode is placed in a vacuum chamber, vacuumed to <1×10 -5Pa, on the anode layer film in the above order, vacuum thermal evaporation of 10 nm of HT-4:HI-3 (97 / 3, w / w) mixture as a hole injection layer; 60 nm of compound HT-4 as a hole transport layer; vacuum evaporation of compound HT-47 as an electron blocking layer material of the device on the hole transport layer, the evaporation rate is 0.1 nm / s, the total film thickness of evaporation is 60 nm; 40 nm of binary mixture of compound P43:RPD-8 (100:3, w / w) of the application as a light emitting layer; vacuum evaporation of 5 nm of ET-17 as a hole blocking layer of the device on the light emitting layer; 25 nm of compound ET-69:ET-57 (50 / 50, w / w) mixture as an electron transport layer; 1 nm of LiF as an electron injection layer; 150 nm of metal aluminum as a cathode. The total evaporation rate of all organic layers and LiF is controlled at 0.1 nm / s, and the evaporation rate of the metal electrode is controlled at 1 nm / s.

[0148] The organic electroluminescent device prepared by the above process was subjected to the following performance test:

[0149] The driving voltage and current efficiency of the organic electroluminescent device prepared by the above method were determined at the same brightness. Specifically, the voltage was increased at a rate of 0.1 V per second, and the voltage when the brightness of the organic electroluminescent device reached 3000 cd / m 2 was determined, which is the driving voltage, and the current density at this time was also measured; the ratio of brightness to current density is the current efficiency. The lifetime test of LT98 was as follows: using a luminance meter, the time for the brightness of the organic electroluminescent device to decrease to 9800 cd / m 2 was measured under a constant current, and the unit was hour. 2

[0150] The device examples 2-10 of the application, comparative examples 1 and 2 were completed according to the above preparation steps and test methods, in examples 2-10, the compound P43 in example 1 was replaced by the compounds of the application listed in Table 3; in comparative examples 1 and 2, the compound P43 was replaced by comparative compounds C3 and C4 shown in Table 3.

[0151] The structure of the comparative compound in the application is as follows:

[0152]

[0153] The following Table 3 is the specific performance data table of the devices prepared in the above examples and comparative examples, in order to more clearly reflect the performance difference between the compounds of the application and the comparative compounds, the test data of voltage, efficiency and lifetime of comparative example 1 are all 1, and the data of each example in the following table are the ratio of the data of the comparative examples.

[0154] Table 3:​

[0155]

[0156]

[0157] Device examples 11-17 and comparative examples 3, 4 of the present application were still prepared according to the above preparation steps and test methods, which were different from example 1 in that a double host material structure was designed in the light-emitting layer, the light-emitting layer of the double host material was prepared by three-source co-evaporation, the weight ratio of the first host and the second host was maintained at 3:7, and the ratio of the total weight of the double host to the dye was still 100:3. The host material of the light-emitting layer in device examples 11-17 and comparative examples 3, 4 was the compound shown in Table 4. Similarly, the test data of voltage, efficiency and lifetime of comparative example 3 were all set to 1, and the data of each example in the table below were the ratio of the data of the comparative example.

[0158] Table 4:

[0159]

[0160] From the above data, it can be seen that when the material of the present application is used as a bipolar single host, the voltage, efficiency and lifetime are all greatly improved compared with comparative example 4. The reason is that the material of the present application has greater rigidity and stronger hole transport capacity compared with C3, and is balanced with electron transport, thereby showing more excellent performance. Although the patent of comparative example 4 also mentions that a more rigid parent nucleus structure can be formed, but since its conjugation degree is already very large, if a host like C1, C2 is formed, its triplet energy level T1 will be greatly reduced, thereby cannot meet the requirements of red light host, resulting in a large decrease in performance.

[0161] When comparative compounds C1, C2 are used as hole-type hosts and matched with P185, the rigidity is too large, which leads to a decrease in the triplet energy level and poor performance.

[0162] The present application provides a compound with a large planar parent nucleus structure. The compound of the present application has good carrier injection and transport performance, and the material is relatively suitable for use as a light-emitting host in the light-emitting layer of an OLED device. Because the light-emitting host needs to balance the transport of holes and electrons, when Y is NR 1 in the general structure of the compound of the present application, R 1 When an electron-deficient group is used, it can be beneficial for the compound of the present application to better achieve the balance of hole and electron transport, at this time the compound of the present application can be used as a bipolar material as a light-emitting host material alone. When Y is NR 1 in the general structure of the compound of the present application, R 1When selected from electron-rich groups, since the compound of the present application is structurally only favorable for hole injection and transport at this time, it is necessary to be used as a dual light-emitting host material together with a compound containing an electron-deficient group.

[0163] Although the present application has been described in connection with the embodiments thereof with reference to the drawings, it is to be understood that the present application is not limited to the embodiments, but those skilled in the art can make various modifications and improvements within the scope of the present inventive concept, and the scope of the present application is outlined by the appended claims.

Claims

1. An organic compound having a structure as shown in Formula I: In formula I, Y is NR 1 , and Z is selected from one of O, S, NR 1 . R 1 one selected from the group consisting of substituted or unsubstituted C6to C30aryl, substituted or unsubstituted C3to C30heteroaryl, substituted or unsubstituted C12to C36arylamino, and substituted or unsubstituted C3to C30heteroarylamino; X1-X 13 each independently selected from CH; each of the above-mentioned substituted or unsubstituted groups, when having a substituent, has the substituent selected from one or a combination of at least two of deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde, C1-C30 chain alkyl, C1-C30 alkoxy, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl.

2. The organic compound according to claim 1, in the formula I, the R 1 one of the following groups selected from the group consisting of substituted or unsubstituted phenyl, naphthyl, anthryl, phenanthryl, indenyl, fluoranthenyl, triphenylenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, benzofluorenyl, furanyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothienyl, pyridyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, phenoxazinyl, phenylamino, naphthylamino, anthrylamino, phenanthrylamino, biphenylamino, carbazolylamino, dibenzothienylamino, dibenzofuranylamino; each of the above-mentioned substituted or unsubstituted groups, when having a substituent, has the substituent selected from one or a combination of at least two of deuterium, halogen, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

3. An organic compound selected from any one of the following structures:

4. Use of the organic compound according to any one of claims 1 to 3 as a functional material in an organic electronic device selected from an organic electroluminescent device. The organic compound is used as a light-emitting layer host material in an organic electroluminescent device.

5. An organic electroluminescent device comprising a first electrode, a second electrode, and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layers contain the organic compound according to any one of claims 1 to 3.

6. An organic electroluminescent device comprising a first electrode, a second electrode, and a hole transport layer, a light-emitting layer, and an electron transport layer interposed between the first electrode and the second electrode, wherein the light-emitting layer contains the organic compound according to any one of claims 1 to 3. The light-emitting layer further contains a phosphorescent light-emitting material.

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