Organic electroluminescent device and electronic device comprising the same

Abstract

The application provides an organic electroluminescent device, a light-emitting layer host material of the organic electroluminescent device comprises a first host compound and a second host compound, the first host compound has a relatively strong bipolar characteristic with electron characteristics, and the second host compound is a bipolar characteristic with relatively strong hole characteristics, the two are matched and applied, the charge mobility and stability are increased, and the luminous efficiency and life characteristics are significantly improved. A hole adjustment layer is further arranged between the light-emitting layer and the anode of the organic electroluminescent device, the layer can adjust the thickness of the hole transport layer, and needs to have an energy level matched with the light-emitting layer host material, so as to adjust the hole injection and transport, and effectively prevent the electrons in the light-emitting layer from entering the hole transport layer, the layer can adjust the carrier transport performance of the device, improve the electron and hole combination rate, and further improve the luminous efficiency of the device.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic electroluminescence, in particular to an organic electroluminescent device and an electronic device comprising the same. BACKGROUND

[0002] In recent years, organic electroluminescent devices (OLED) have been widely concerned as the next generation of flat panel display technology. Compared with liquid crystal display (LCD), OLED has a wider color gamut, higher contrast, wider temperature range, faster response time, and can realize flexible display, etc.

[0003] An organic electroluminescent device (OLED) generally comprises an anode, a cathode and an organic layer formed between the two electrodes. The organic layer can include a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (containing a host and a dopant material), an electron transport layer, an electron injection layer, etc. If a voltage is applied to the organic electroluminescent device, holes and electrons are injected into the light-emitting layer by the anode and the cathode, respectively. Then in the light-emitting layer, the injected holes and electrons recombine to form excitons. The excitons in the excited state release energy outward, and then the light-emitting layer emits light outward.

[0004] According to the statistical rules of electron spin, singlet excitons and triplet excitons are generated in a ratio of 25%:75%. And according to the classification of light-emitting principle, fluorescent light is the light-emitting of singlet excitons, so 25% is the limit of internal quantum efficiency in organic electroluminescent elements. As for phosphorescent light, it is the light-emitting of triplet excitons, so in the case of effective intersystem crossing from triplet excitons, the internal quantum efficiency can theoretically reach 100% (i.e. using all singlet and triplet excitons). For organic electroluminescent devices, the elements with optimal performance are designed according to the light-emitting mechanisms of fluorescent and phosphorescent types. In particular, for phosphorescent organic electroluminescent devices, it is known from their light-emitting characteristics that when simply borrowing fluorescent element technology, high-performance elements cannot be obtained. However, with the acceleration of industrialization process, more and more OLED materials and device design schemes with low power consumption, high efficiency and long life have attracted people's attention. In the more common OLED device structure at present, because the mobility of hole type (P) material is generally higher than that of electron type (N) material, the host material is usually a single N-type material, and the use of a single N-type host material often has a lower hole mobility and even a strong hole blocking effect, which leads to insufficient recombination of electrons and holes in the light-emitting layer, low energy utilization rate, and ultimately low current efficiency and serious impact on device life.

[0005] At present, there are still problems of poor performance in the use of organic electroluminescent devices, such as high driving voltage, low luminous efficiency or short service life, which affect the use field of organic electroluminescent devices. Therefore, it is still necessary to further study in this field to improve the performance of organic electroluminescent devices. SUMMARY

[0006] The present application aims to overcome the deficiencies in the prior art, and provide an organic electroluminescent device and an electronic device comprising the same, which can improve the luminous efficiency and prolong the service life of the device.

[0007] In one aspect, the present application provides an organic electroluminescent device, which comprises, in sequence, an anode, a hole injection layer, a hole transport layer, an organic light-emitting layer, an electron transport layer, an electron injection layer and a cathode, wherein a hole adjustment layer is further provided between the hole transport layer and the organic light-emitting layer, and the hole adjustment layer contains a compound represented by Formula I:

[0008]

[0009] wherein L is selected from a single bond or a substituted or unsubstituted arylene group having 6-20 carbon atoms;

[0010] Ar is selected from a substituted or unsubstituted aryl group having 6-30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12-30 carbon atoms;

[0011] Each of R1, R2, R3, R4, R5 and R6, which are the same or different, is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1-5 carbon atoms, an aryl group having 6-12 carbon atoms, a heteroaryl group having 5-12 carbon atoms, a haloalkyl group having 1-5 carbon atoms, a deuterated alkyl group having 1-5 carbon atoms, a trialkylsilyl group having 3-12 carbon atoms, or an alkoxy group having 1-5 carbon atoms;

[0012] R1-R6 are represented by R i , n1-n6 are represented by n i , i is a variable representing 1, 2, 3, 4, 5 or 6, and n1, n2, n3, n4, n5 and n6 represent the number of R1, R2, R3, R4, R5 and R6, respectively;

[0013] wherein when i is 1, n i is selected from 0, 1, 2 or 3; when i is 2, 4, 5 or 6, n i is selected from 0, 1, 2, 3 or 4; when i is 3, n i is selected from 0, 1, 2, 3, 4 or 5, and any two of n i have the same or different values;

[0014] the substituents in Ar and L are the same or different, and are each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms; optionally, in Ar, any two adjacent substituents form a ring;

[0015] the organic light-emitting layer is composed of a light-emitting layer host and a dopant, the light-emitting layer host comprises a first host compound and a second host compound, the first host compound has a structure as shown in Formula II:

[0016]

[0017] in Formula II, X and Z are each independently O, S, — N=, or N(R7), and only one of X and Z is — N=;

[0018] R7 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 30 carbon atoms;

[0019] R8 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 30 carbon atoms;

[0020] each R9 is independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, n9 represents the number of R9, and n9 is selected from 0, 1, 2, 3, 4, 5, 6, or 7;

[0021] Het is a 6- to 18-membered electron-deficient nitrogen-containing heteroarylene group;

[0022] L1, L2, and L3 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms;

[0023] Ar1 and Ar2 are each independently hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0024] R7, R8, L1, L2, L3, Ar1and Ar2independently of each other are selected from deuterium, cyano, a halogen group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms;

[0025] The structure of the second host compound consists of formula III and formula III-2:

[0026]

[0027] the position marked with * in formula III is fused to the position marked with * in formula III-2;

[0028] ring A and ring B are independently selected from a phenyl ring or a naphthyl ring;

[0029] L4is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms;

[0030] Ar3is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0031] Y is selected from O, S or N(R 11 ), R 11 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 12 to 30 carbon atoms;

[0032] each R a , R b and R 10 is independently selected from deuterium, cyano, a halogen group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms or an alkoxy group having 1 to 5 carbon atoms;

[0033] n a denotes the number of R a , n a is selected from 0, 1, 2, 3, 4, 5 or 6, when n a is greater than 1, any two R a are identical or different;

[0034] n b denotes the number of R b , n b0, 1, 2, 3, 4, 5, or 6, when n b Any two R b are the same or different;

[0035] n 10 represents the number of R 10 , n 10 is selected from 0, 1, or 2, when n 10 is greater than 1, any two R 10 are the same or different; optionally, any two adjacent R 10 are connected to each other to form a 6-10 membered aromatic ring.

[0036] Ar3, L4, and R 11 independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1-5 carbon atoms, a haloalkyl group having 1-5 carbon atoms, a deuterated alkyl group having 1-5 carbon atoms, an aryl group having 6-12 carbon atoms, a heteroaryl group having 5-12 carbon atoms, a trialkylsilyl group having 3-12 carbon atoms, an alkoxy group having 1-5 carbon atoms, or a cycloalkyl group having 5-10 carbon atoms; optionally, in Ar3and R 11 , any two adjacent substituents form a ring.

[0037] The present application provides an organic electroluminescent device, the light-emitting layer host material of which comprises a first host compound (compound of formula II) and a second host compound (compound consisting of formula III and formula III-2) of the light-emitting layer, the first host compound has a relatively strong bipolar characteristic with electron characteristics, and the second host compound has a relatively strong bipolar characteristic with hole characteristics. The use of the two compounds increases the charge mobility and stability, thereby significantly improving the luminous efficiency and lifetime characteristics. The organic light-emitting layer and the hole transport layer of the organic electroluminescent device provided by the present application further comprise a hole adjustment layer. This layer can adjust the thickness of the hole transport layer and needs to have a LUMO energy level matching the light-emitting layer host material to effectively prevent electrons in the light-emitting layer from entering the hole transport layer. This layer can adjust the carrier transport performance of the device, improve the electron and hole combination rate, and thus improve the luminous efficiency of the device.

[0038] In the present application, GH-N is an electron-type host material, and GH-P is a hole-type host material.

[0039] Specifically, the first host compound (GH-N type material) of the light-emitting layer of the organic electroluminescent device comprises a nitrogen-containing six-membered ring (Het group) with high electron transport properties and a fused nitrogen-containing heteroaromatic ring to stably and effectively transport electrons, and the second host compound (GH-P type material) comprises an indolocarbazole structure with high T1, which effectively injects and transports holes. The two host materials are reasonably matched, thereby reducing the driving voltage and improving the current efficiency. The hole adjustment layer compound (compound shown in Formula I) of the organic electroluminescent device is a triarylamine structure with a double fluorene group. The LUMO value of the compound is matched with the first host and the second host compound. Through a large number of experiments, it is verified that the addition of the hole adjustment compound in the adjacent functional layer of the light-emitting layer can finally realize the adjustment of the electron and hole transport properties in the functional layer of the device, so as to realize the optimal balance of hole and electron transport, maximize the luminous efficiency of the device and reduce the working voltage of the device, and prolong the service life of the device.

[0040] In another aspect, the present application provides an electronic device comprising the above-mentioned organic electroluminescent device.

[0041] It should be understood that the above general description and the following detailed description are only exemplary and explanatory, and cannot limit the present application. BRIEF DESCRIPTION OF DRAWINGS

[0042] The accompanying drawings are included to provide a further understanding of the present application, and constitute a part of the specification, and are used together with the following detailed description to explain the present application, but do not constitute a limitation on the present application.

[0043] Figure 1 is a structural schematic diagram of an organic electroluminescent device according to an embodiment of the present application.

[0044] Figure 2 is a structural schematic diagram of an electronic device according to an embodiment of the present application.

[0045] EXPLANATION OF REFERENCE NUMERALS

[0046] 100, anode; 200, cathode; 300, functional layer; 310, hole injection layer; 321, hole transport layer; 322, hole adjustment layer; 330, organic light-emitting layer; 340, hole blocking layer; 350, electron transport layer; 360, electron injection layer; 400, electronic device. DETAILED DESCRIPTION

[0047] Example embodiments now will be described more fully hereinafter with reference to the accompanying drawings; however, the example embodiments can be implemented in any number of ways. Rather, the present embodiments are to be considered as illustrative and not restrictive, and the example embodiments are susceptible to various modifications and alternative forms. Specific implementations are described in detail herein with reference to the accompanying drawings, but the example embodiments are not limited to the specific implementations described herein. The described features, structures, or characteristics can be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of the present embodiments. The embodiments described herein are not intended to be hardware dependent unless specifically stated otherwise.

[0048] In the drawings, the thicknesses of regions and layers can be exaggerated for clarity. Like reference numerals in different drawings denote like or similar structures, and thus their detailed descriptions will be omitted.

[0049] The present application provides an organic electroluminescent device, comprising in sequence an anode, a hole injection layer, a hole transport layer, an organic light-emitting layer, an electron transport layer, an electron injection layer and a cathode, wherein a hole adjustment layer is further provided between the hole transport layer and the organic light-emitting layer, and the hole adjustment layer contains a compound represented by Formula I:

[0050]

[0051] wherein L is selected from a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms;

[0052] Ar is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 30 carbon atoms;

[0053] each of R1, R2, R3, R4, R5 and R6 is the same or different, and is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, or an alkoxy group having 1 to 5 carbon atoms;

[0054] R1 to R6 are represented by R i , and n1 to n6 are represented by n i , i is a variable, representing 1, 2, 3, 4, 5 or 6, and n1, n2, n3, n4, n5 and n6 represent the number of R1, R2, R3, R4, R5 and R6, respectively;

[0055] wherein when i is 1, n i is selected from 0, 1, 2 or 3; when i is 2, 4, 5 or 6, n i is selected from 0, 1, 2, 3 or 4; when i is 3, n i is selected from 0, 1, 2, 3, 4 or 5, and any two of n i have the same or different values.

[0056] the substituents in Ar and L are the same or different, and are each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms; optionally, in Ar, any two adjacent substituents form a ring;

[0057] the organic light-emitting layer is composed of a light-emitting layer host and a dopant, the light-emitting layer host comprises a first host compound and a second host compound, the structure of the first host compound is shown in formula II:

[0058]

[0059] in formula II, X and Z are each independently O, S, — N= or N(R7), and only one of X and Z is — N=;

[0060] that is, in the above formula II, the dotted line indicates that when X is — N=, then X-C(R8) is a double bond and Z-C(R8) is a single bond, and vice versa, if Z is — N=, then Z-C(R8) is a double bond and C(R8)-X is a single bond; R7 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 30 carbon atoms;

[0061] R8 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 30 carbon atoms;

[0062] each R9 is independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, and n9 represents the number of R9, n9 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0063] Het is a 6-18 membered electron-deficient nitrogen-containing heteroarylene;

[0064] L1, L2 and L3 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms;

[0065] Ar1and Ar2are each independently hydrogen, a substituted or unsubstituted aryl group having a carbon number of 6 to 30, a substituted or unsubstituted heteroaryl group having a carbon number of 3 to 30;

[0066] R7, R8, L1, L2, L3, Ar1, and Ar2are each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having a carbon number of 1 to 5, a haloalkyl group having a carbon number of 1 to 5, a deuterated alkyl group having a carbon number of 1 to 5, an aryl group having a carbon number of 6 to 12, a heteroaryl group having a carbon number of 5 to 12, a trialkylsilyl group having a carbon number of 3 to 12, an alkoxy group having a carbon number of 1 to 5, or a cycloalkyl group having a carbon number of 5 to 10;

[0067] The structure of the second host compound consists of Formula III and Formula III-2:

[0068]

[0069] the position indicated by * in Formula III is fusedly connected to any two adjacent positions of * in Formula III-2;

[0070] Ring A and Ring B are each independently selected from a benzene ring or a naphthalene ring;

[0071] L4is selected from a single bond, a substituted or unsubstituted arylene group having a carbon number of 6 to 20, a substituted or unsubstituted heteroarylene group having a carbon number of 5 to 18;

[0072] Ar3is selected from a substituted or unsubstituted aryl group having a carbon number of 6 to 30, or a substituted or unsubstituted heteroaryl group having a carbon number of 3 to 30;

[0073] Y is selected from O, S, or N(R 11 ), R 11 is selected from a substituted or unsubstituted aryl group having a carbon number of 6 to 30, or a substituted or unsubstituted heteroaryl group having a carbon number of 12 to 30;

[0074] Each R a , R b , and R 10 is independently selected from deuterium, a cyano group, a halogen group, an alkyl group having a carbon number of 1 to 5, a haloalkyl group having a carbon number of 1 to 5, a deuterated alkyl group having a carbon number of 1 to 5, an aryl group having a carbon number of 6 to 12, a heteroaryl group having a carbon number of 5 to 12, a trialkylsilyl group having a carbon number of 3 to 12, or an alkoxy group having a carbon number of 1 to 5;

[0075] n a represents the number of R a , n a is selected from 0, 1, 2, 3, 4, 5, or 6, when n a is greater than 1, any two R athe same or different;

[0076] n b represents the number of R b , n b is selected from 0, 1, 2, 3, 4, 5 or 6, when n b is greater than 1, any two R b the same or different;

[0077] n 10 represents the number of R 10 , n 10 is selected from 0, 1 or 2, when n 10 is greater than 1, any two R 10 the same or different; optionally, any two adjacent R 10 are connected to each other to form a 6-10 membered aromatic ring;

[0078] the substituents in Ar3, L4, R 11 are each independently selected from deuterium, cyano, a halogen group, an alkyl group having 1-5 carbon atoms, a haloalkyl group having 1-5 carbon atoms, a deuterated alkyl group having 1-5 carbon atoms, an aryl group having 6-12 carbon atoms, a heteroaryl group having 5-12 carbon atoms, a trialkylsilyl group having 3-12 carbon atoms, an alkoxy group having 1-5 carbon atoms, or a cycloalkyl group having 5-10 carbon atoms, optionally, in Ar3and R 11 , any two adjacent substituents form a ring.

[0079] In the present application, the description mode "each of…… is independently" and "…… is independently selected from" can be interchangeable, and should be interpreted in a broad sense, which can mean that the specific options expressed by the same symbols in different groups do not affect each other, or that the specific options expressed by the same symbols in the same group do not affect each other. For example, "each of R1, R2, R3, R4, R5and R6is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, an alkyl group having 1-5 carbon atoms, a deuterated alkyl group having 1-5 carbon atoms, an aryl group having 6-12 carbon atoms, a heteroaryl group having 5-12 carbon atoms, a trialkylsilyl group having 3-12 carbon atoms, an alkoxy group having 1-5 carbon atoms, or a cycloalkyl group having 5-10 carbon atoms" means that: R1, R2, R3, R4, R5and R6are selected from hydrogen, deuterium, fluorine, chlorine, bromine, an alkyl group having 1-5 carbon atoms, a deuterated alkyl group having 1-5 carbon atoms, an aryl group having 6-12 carbon atoms, a heteroaryl group having 5-12 carbon atoms, a trialkylsilyl group having 3-12 carbon atoms, an alkoxy group having 1-5 carbon atoms, or a cycloalkyl group having 5-10 carbon atoms, and the options of each R1, R2, R3, R4, R5and R6do not affect each other. wherein each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, chlorine, means that: formula Q-1 represents that there are q substituents R" on the benzene ring, each R" can be the same or different, and the options of each R" do not affect each other; formula Q-2 represents that there are q substituents R" on each benzene ring of the biphenyl, the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.

[0080] In the present application, the term "optionally", "optionally" means that the event or circumstance described subsequently can occur or not occur. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents can form a ring or not form a ring, that is, it includes the case where the two adjacent substituents form a ring and the case where the two adjacent substituents do not form a ring. For another example, "optionally, any two adjacent Ra form a ring" means that any two adjacent substituents Ra can be connected to each other to form a ring, or any two adjacent substituents Ra can exist independently. In the present application, in "two adjacent substituents form a ring", "adjacent" can include two substituents on the same atom, and can also include two substituents on two adjacent atoms; when the two substituents are on the same atom, the two substituents can form a saturated or unsaturated ring with the atom to which they are commonly connected; when the two substituents are on two adjacent atoms, the two substituents can be fused into a ring. For example, two adjacent R 10 Connected to each other to form a 6-10 membered aromatic ring, that is, when the adjacent substituents form a ring, a 6-10 membered aromatic ring such as a benzene ring or a naphthalene ring can be formed.

[0081] The "ring" in the present application includes saturated rings (i.e. aliphatic rings) and unsaturated rings; saturated rings are cycloalkyl and heterocycloalkyl, and unsaturated rings are cycloalkenyl, heterocycloalkenyl, aryl and heteroaryl. In the present application, a ring system formed by n atoms is an n-membered ring. For example, a phenyl group is a 6-membered aryl group. The 5-13 membered ring in the present application is, for example but not limited to, cyclopentane, cyclohexane, benzene ring, indene ring, adamantane, fluorene ring, naphthalene ring, etc. The 5-13 membered ring refers to a ring system formed by 5-13 ring atoms. For example, a fluorene ring is a 13-membered ring, a cyclohexane is a 6-membered ring, and adamantane is a 10-membered ring.

[0082] Further, the 6-10 membered aromatic ring is selected from a benzene ring or a naphthalene ring.

[0083] In the present application, the term "substituted or unsubstituted" means that the functional group recited after the term can or can not have a substituent (hereinafter, the substituents will be collectively referred to as Rcfor convenience of description). For example, "substituted or unsubstituted aryl" means aryl having a substituent Rc, or aryl which is not substituted. The substituents Rcmentioned above, for example, can be deuterium, cyano, fluorine, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms. In the present application, a "substituted" functional group can be substituted with one or more than two substituents from the above-mentioned Rc; when two substituents Rcare attached to the same atom, the two substituents Rcmay exist independently or be connected to each other to form a ring with the atom; when two substituents Rcexist adjacently on a functional group, the two adjacent substituents Rcmay exist independently or be fused with the functional group to which they are attached to form a ring.

[0084] In the present application, "a plurality of" means two or more, for example, two, three, four, five, six, and the like.

[0085] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group means the total number of carbon atoms. For example, if L is selected from a substituted arylene group having 12 carbon atoms, the total number of carbon atoms of the arylene group and the substituents thereon is 12. For example, L is having 12 carbon atoms.

[0086] In the present application, an alkyl group having 1 to 5 carbon atoms can include a straight-chain alkyl group having 1 to 5 carbon atoms and a branched-chain alkyl group having 3 to 5 carbon atoms. The number of carbon atoms of the alkyl group, for example, can be 1, 2, 3, 4, 5, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and the like.

[0087] In the present application, a cycloalkyl group means a saturated hydrocarbon containing an alicyclic structure, including monocyclic and fused ring structures. The cycloalkyl group can have 5 to 10 carbon atoms, and the numerical range of "5 to 10", for example, means each integer in the given range; for example, "5 to 10 carbon atoms" means a cycloalkyl group which can contain 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, or 10 carbon atoms, for example, but not limited to, a cyclohexyl group, a cyclopentyl group, an adamantyl group.

[0088] In the present application, aryl refers to an optionally functionalized or substituted group derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups linked by a carbon-carbon bond in conjugation, a monocyclic aryl group and a fused ring aryl group linked by a carbon-carbon bond in conjugation, or two or more fused ring aryl groups linked by a carbon-carbon bond in conjugation. That is, unless otherwise specified, two or more aromatic groups linked by a carbon-carbon bond in conjugation can also be considered as an aryl group in the present application. Among them, the fused ring aryl group can include, for example, a bicyclic fused aryl group (e.g., naphthyl), a tricyclic fused aryl group (e.g., phenanthryl, fluorenyl, anthryl), and the like. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of the aryl group can include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrenyl, triphenylenyl, benzofluoranthene, and the like.

[0089] In the present application, the fluorenyl group can be substituted by 1, 2, or more substituents, wherein any 2 adjacent substituents can also combine with each other to form a substituted or unsubstituted spiro ring structure. In the case where the above-mentioned fluorenyl group is substituted, the substituted fluorenyl group can be, for example, but is not limited to:

[0090]

[0091] In the present application, the arylene group refers to a divalent group formed by further losing one hydrogen atom from the aryl group.

[0092] In the present application, the terphenyl group includes

[0093] In the present application, the number of carbon atoms of the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group having a carbon atom number of 18 refers to a total carbon atom number of 18 of the aryl group and the substituents.

[0094] In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group can be 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 25, or 30. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having a carbon atom number of 6-30, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having a carbon atom number of 6-25, in yet other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having a carbon atom number of 6-18, and in still other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having a carbon atom number of 6-15.

[0095] In the present application, the aryl group as a substituent group is, for example, but is not limited to, phenyl, naphthyl, anthryl, phenanthryl, biphenyl, fluorenyl, and the like.​​

[0096] In the present application, heteroaryl refers to a monovalent aromatic ring or its derivative which can contain 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatoms can be at least one of B, O, N, P, Si, Se and S. The heteroaryl can be a monocyclic heteroaryl or a polycyclic heteroaryl, in other words, the heteroaryl can be a single aromatic ring system or a plurality of aromatic ring systems connected by a carbon-carbon bond in conjugation, and any of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. For example, the heteroaryl can include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, thienothiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, etc., but is not limited thereto.

[0097] In the present application, the term "heteroaryl" refers to a divalent or higher valent group formed by further losing one or more hydrogen atoms from the heteroaryl.

[0098] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having 5 to 30 carbon atoms, in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having 12 to 18 carbon atoms, in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having 5 to 18 carbon atoms, in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having 5 to 12 carbon atoms.

[0099] In the present application, the heteroaryl as a substituent group is, for example, but not limited to, pyridyl, carbazolyl, dibenzothiophenyl, dibenzofuranyl.

[0100] In the present application, the substituted heteroaryl can be a heteroaryl in which one or more hydrogen atoms in the heteroaryl is substituted with a group such as a deuterium atom, a halogen group, -CN, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, a halogenated alkyl group, etc. It should be understood that the number of carbon atoms of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and the substituents on the heteroaryl.

[0101] In the present application, a 6-18 membered electron-deficient nitrogen-containing heteroarylene group refers to a group formed by removing two or more hydrogen atoms from a heteroaromatic ring having 6-18 ring atoms and containing an sp2 hybridized nitrogen atom. Examples of such a group include, but are not limited to, a pyrimidinylene group, a triazinylene group, a pyridazinylene group, a pyrazinylene group, a quinazolinylene group, a quinoxalinylene group, a pyridopyrimidinylene group, a pyridopyrazinylene group, a pyrazinopyrazinylene group, a phenanthrolinylene group, a dithiadiazepinylene group, a dithiadiazepinylene group, and the like. 2 In the present application, a 6-18 membered electron-deficient nitrogen-containing heteroarylene group refers to a group formed by removing two or more hydrogen atoms from a heteroaromatic ring having 6-18 ring atoms and containing an sp2 hybridized nitrogen atom. Examples of such a group include, but are not limited to, a pyrimidinylene group, a triazinylene group, a pyridazinylene group, a pyrazinylene group, a quinazolinylene group, a quinoxalinylene group, a pyridopyrimidinylene group, a pyridopyrazinylene group, a pyrazinopyrazinylene group, a phenanthrolinylene group, a dithiadiazepinylene group, a dithiadiazepinylene group, and the like.

[0102] Further, the 6-18 membered electron-deficient nitrogen-containing heteroarylene group contains at least two nitrogen atoms.

[0103] In the present application, a halogen group can include fluorine, iodine, bromine, chlorine, and the like.

[0104] In the present application, a trialkylsilyl group refers to a group represented by the following formula (a): wherein R G1 , R G2 , and R G3 are each independently an alkyl group. Specific examples of the trialkylsilyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a propyldimethylsilyl group.

[0105] In the present application, a halogenated alkyl group means an alkyl group substituted with one or more halogen atoms, wherein the alkyl group has the meaning as described in the present application. In one embodiment, a halogenated alkyl group having 1-5 carbon atoms includes a fluorine-substituted alkyl group having 1-5 carbon atoms. Examples of such a group include, but are not limited to, a trifluoromethyl group, a difluoromethyl group, a 1-fluoro-2-chloroethyl group, and the like.

[0106] In the present application, an indefinite position linking bond means a single bond extending from a ring system which means that one end of the linking bond can be connected to any position in the ring system through which the bond extends, and the other end is connected to the rest of the molecule. For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to the rest of the molecule through two indefinite position linking bonds extending through the bicyclic ring, and the meaning represented thereby includes any of the possible connection modes as shown in formulae (f-1) to (f-10).

[0107]

[0108] For example, as shown in the following formula (X'), the fluorenyl group represented by formula (X') is connected to the rest of the molecule through an unspecified bond from the side of the central benzene ring, and the meaning represented thereby includes any of the possible connection modes as shown in formulae (X'-1) to (X'-5).

[0109]

[0110] In the present application, an unspecified substituent refers to a substituent connected through a single bond from the center of a ring system, and it means that the substituent can be connected to any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is connected to the quinoline ring through an unspecified bond, and the meaning represented thereby includes any of the possible connection modes as shown in formulae (Y-1) to (Y-7).

[0111]

[0112] In the present application, the compound represented by formula I specifically has the structures represented by formulae I-1 to I-4:

[0113]

[0114] In some embodiments, in formula I, each of R1, R2, R3, R4, R5, and R6 is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, trifluoromethyl, trideuteromethyl, or trimethylsilyl.

[0115] In some embodiments, in formula I, n4 is 0 or 1, and R4 is selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, trifluoromethyl, or trideuteromethyl.

[0116] In some embodiments, in formula I, Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl.

[0117] Alternatively, each of the substituents in Ar is independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, or naphthyl; optionally, in Ar, any two adjacent substituents form a benzene ring or a fluorene ring

[0118] Optionally, Ar is selected from the group consisting of:

[0119]

[0120]

[0121] Further optionally, Ar is selected from the group consisting of:

[0122]

[0123] In some embodiments, in Formula I, L is selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene.

[0124] Optionally, each substituent in L is independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, or phenyl.

[0125] In some more specific embodiments, in Formula I, L is selected from a single bond or the following groups:

[0126]

[0127] In some more specific embodiments, the compound of Formula I is selected from the group consisting of:

[0128]

[0129]

[0130]

[0131]

[0132]

[0133] In some embodiments of the application, in Formula II, the Het group is selected from the group consisting of:

[0134] wherein, the * indicates the bond to L3, and the remaining two connecting bonds are to L1and L2, respectively.

[0135] In some embodiments of the application, in Formula II, the Het group is selected from the group consisting of:

[0136]

[0137] wherein, denotes the position at which Het is attached to the L3 group, denotes the position at which Het is attached to -L1-Ar1, denotes the position at which Het is attached to -L2-Ar2; does not contain denotes that in this structure L2 is a single bond and Ar2 is hydrogen.

[0138] In the present application, when the Het group in formula II is a triazine group, a better balance between hole and electron mobility of the compound is achieved, and the efficiency of the device is better when the compound is used in the light-emitting layer of the device.

[0139] In some embodiments of the present application, in formula II, X and Z are each independently O, S, or -N=. In some embodiments of the present application, in formula II, L3 is a single bond or a phenylene group.

[0140] Alternatively, in formula II, is selected from the group consisting of the following structures:

[0141] In some embodiments of the present application, the compound of formula II has the following structural formula II-1:

[0142] Z is selected from O or S.

[0143] Further, the compound of formula II has the following structures of formulae II-2 to II-5:

[0144]

[0145] In some embodiments of the present application, in formula II, R8 is selected from the group consisting of the following groups:

[0146]

[0147] Further alternatively, in formula II, R8 is selected from the group consisting of the following groups:

[0148]

[0149]

[0150] In some embodiments, in formula II, each R9 is independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, or naphthyl.

[0151] In some embodiments, in Formula II, L1, L2 and L3 are each independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl.

[0152] Optionally, the substituents in L1, L2 and L3 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0153] In some more specific embodiments, in Formula II, L1, L2, and L3 are each independently selected from the group consisting of single bonds or the following groups:

[0154]

[0155] In some embodiments, Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted carbazoyl.

[0156] Ar2 is selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted carbazoyl.

[0157] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0158] In some embodiments, Ar1 is selected from the following groups, and Ar2 is selected from the group consisting of hydrogen or the following groups:

[0159]

[0160] In some more specific embodiments, Ar1 is selected from the group consisting of the following groups, and Ar2 is selected from the group consisting of hydrogen or the group consisting of the following groups:

[0161]

[0162] In some more specific embodiments, the compound of formula II is selected from the group consisting of the following compounds:

[0163]

[0164]

[0165]

[0166]

[0167] In some embodiments, in the second host compound, n a , n b are each 0.

[0168] In some embodiments, the second host compound is selected from the following structures III-3 to III-21:

[0169]

[0170] In some embodiments, in the second host compound, R a , R b and R 10 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl, trifluoromethyl, trideuteromethyl or trimethylsilyl, optionally, any two adjacent R 10 are connected to each other to form a benzene ring or a naphthalene ring.

[0171] In some embodiments, in the second host compound, L4is selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted dithiophenylene, substituted or unsubstituted dibenzofuranylene.

[0172] Optionally, the substituents in L4are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0173] In some more specific embodiments, in the second host compound, L4is selected from the group consisting of a single bond or the following groups:

[0174]

[0175] In some embodiments, in the second host compound, Ar3and R 11 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted terphenylyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dithiophenyl, substituted or unsubstituted carbazolyl.

[0176] Optionally, Ar3and R11 The substituents in each group are independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthio, dibenzothiophene, or dibenzofuranyl; optionally, Ar3 and R 11 In this process, any two adjacent substituents form a fluorene ring.

[0177] Optionally, in the second host compound, Ar3 is selected from the group consisting of:

[0178]

[0179] Optionally, R 11 Selected from the group consisting of the following groups:

[0180]

[0181] Further, optionally, Ar3 is selected from the following groups:

[0182]

[0183] Optionally, in the second host compound, R 11 Selected from the group consisting of the following groups:

[0184]

[0185] In some more specific embodiments, the second host compound is selected from the group consisting of:

[0186]

[0187]

[0188]

[0189] In this application, the light-emitting layer of the organic electroluminescent device comprises a host material and a dopant. The host material comprises a first host compound and a second host compound. The mass ratio of the first host compound to the second host compound is 1:99 to 99:1, preferably 10:90 to 90:10, more preferably 30:70 to 70:30, and even more preferably 40:60 to 60:40.

[0190] In some embodiments, the mass ratio of the first host compound (compound of formula II) and the second host compound (compound formed by fusion of formula III and formula III-2) in the light-emitting layer of the organic electroluminescent device is 30:70 to 70:30.

[0191] Optionally, the mass ratio of the first host compound (compound of Formula II) and the second host compound (compound of Formula III) in the light-emitting layer host is 35:60, 40:60, 45:55, 50:50, 55:45, 60:40, 65:35.

[0192] The first host compound and the second host compound can be combined in the desired ratio by placing them in a shaker and then mixing them; by placing them in a glass tube with the aid of heating, dissolving them, and then collecting the result, or by dissolving them in a solvent, etc.

[0193] The present application not only provides an organic electroluminescent device comprising a compound represented by Formula II and a compound represented by Formula III as a light-emitting layer and a compound of Formula I as a hole adjustment layer of the device. The present application also provides an electronic device comprising the organic electroluminescent device of the present disclosure.

[0194] The organic electroluminescent device of the present application includes a first electrode; a second electrode; and at least one organic layer between the first electrode and the second electrode. One of the first electrode and the second electrode can be an anode, and the other can be a cathode. The organic layer includes an organic light-emitting layer, and further includes at least one layer selected from a hole injection layer, a hole transport layer, a hole adjustment layer, an electron transport layer, a hole blocking layer, an electron injection layer. Each layer can further consist of multiple layers or be formed by mixing multiple materials.

[0195] Depending on the kind of materials forming the first electrode and the second electrode, the organic electroluminescent device can be a top emission type, a bottom emission type, or a dual emission type.

[0196] To form each layer constituting the organic electroluminescent device of the present application, a dry film formation method such as vacuum deposition, sputtering, plasma, ion plating method, etc., or a wet film formation method such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating method, etc., can be used. When using a wet film formation method, a thin film is formed by dissolving or dispersing the material constituting each layer in a suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent is not particularly limited as long as the material constituting each layer is soluble or dispersible in a solvent that is not a problem in terms of film formation ability.

[0197] In addition, the first host compound and the second host compound can be subjected to film formation in the above-listed methods, typically by a co-evaporation method or a mixed evaporation method. The co-evaporation is a mixed deposition method in which two or more materials are placed in respective single crucible sources and an electric current is applied to both cells to evaporate the materials at the same time. The mixed evaporation is a mixed deposition method in which two or more materials are mixed in one crucible source before evaporation and an electric current is applied to the cell to evaporate the materials.

[0198] According to an embodiment, as shown in FIG. 1, an organic electroluminescent device can include an anode 100, a hole injection layer 310, a hole transport layer 321, a hole adjustment layer 322, an organic light-emitting layer 330, an electron transport layer 350, an electron injection layer 360, and a cathode 200, which are sequentially stacked. Figure 1

[0199] Optionally, a hole blocking layer 340 is provided between the organic light-emitting layer 330 and the electron transport layer 350.

[0200] Optionally, the anode 100 includes an anode material, which is optionally a material having a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include a metal such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); a combination of a metal and an oxide such as ZnO:Al or SnO2:Sb; or a conductive polymer such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but is not limited thereto. Optionally, a transparent electrode including indium tin oxide (ITO) as the anode is included.

[0201] In the present application, the hole transport layer 321 can include one or more hole transport materials, which can be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, and can be specifically selected from the compounds shown below or any combination thereof:

[0202]

[0203]

[0204]

[0205]

[0206]

[0207] ​In an embodiment, the hole transport layer 321 comprises compound HT-17.

[0208] Optionally, the hole adjustment layer 322 (also referred to as a second hole transport layer or an electron blocking layer) can also comprise other triarylamine compounds, which are not particularly limited in the present application. In an embodiment, the hole adjustment layer 322 is a compound of formula I of the present application.

[0209] The compound provided in the present application has a high hole transport efficiency, which can improve the overall hole transport efficiency of the hole transport layer. The organic compound provided in the present application is a triarylamine compound, which has a large band gap. The LUMO is relatively shallow, so that the hole adjustment layer 322 can achieve an electron blocking effect, thereby improving the service life of the organic electroluminescent device. In another aspect, the organic compound provided in the present application can have a suitable HOMO energy level, so that the HOMO energy level between the hole adjustment layer 322 and the hole transport layer 321 is relatively small, thereby improving the hole injection efficiency of the hole transport layer 321 and reducing the operating voltage of the organic electroluminescent device.

[0210] In the present application, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to enhance the ability of injecting holes into the hole transport layer 321. The hole injection layer 310 can be selected from diphenylamine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in the present application. The material of the hole injection layer 310 can be selected from the following compounds or any combination thereof, for example;

[0211]

[0212] In an embodiment of the present application, the hole injection layer 310 comprises HAT-CN.

[0213] In the present application, the organic light-emitting layer is a layer from which light is emitted, and can be a single layer or a plurality of layers stacked therein. According to an embodiment of the present application, the doping concentration of the dopant compound in the light-emitting layer can be less than 20% (wt%) relative to the host compound.

[0214] The organic light-emitting layer 330 is composed of a host material and a dopant. The holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form an exciton, which transfers energy to the host material, and the host material transfers energy to the dopant, thereby enabling the dopant to emit light.

[0215] The dopant is at least one phosphorescent dopant or fluorescent dopant, preferably at least one phosphorescent dopant. The dopant can be selected from a red phosphorescent dopant, a green phosphorescent dopant, or a blue dopant. The phosphorescent dopant material used in the present application is not particularly limited, but can be preferably selected from a complex compound of metalized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably selected from a complex compound of ortho-metalized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably an ortho-metalized iridium complex compound.

[0216] Specific examples of the phosphorescent dopant include, but are not limited to,

[0217]

[0218] In one embodiment, the dopant is Ir(dmpq)2(acac).

[0219] The electron transport layer 350 can be a single layer structure or a multi-layer structure, which can include one or more electron transport materials, which can generally include a metal complex and / or a nitrogen-containing heterocyclic derivative, wherein the metal complex material can be selected from LiQ, Alq3, Bepq2, etc.; the nitrogen-containing heterocyclic derivative can be an aromatic ring having a nitrogen-containing six-membered ring or five-membered ring skeleton, a fused aromatic ring compound having a nitrogen-containing six-membered ring or five-membered ring skeleton, etc., and specific examples include, but are not limited to, BCP, Bphen, NBphen, DBimiBphen, BimiBphen, etc. 1,10-phenanthroline compounds, or nitrogen-containing aryl-containing anthracene compounds, triazine compounds, or pyrimidine compounds having the following structure.

[0220]

[0221] In one specific embodiment, the electron transport layer 350 contains LiQ and ET-17.

[0222] Optionally, the cathode 200 includes a cathode material, which is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or an alloy thereof; or a multi-layer material such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but are not limited thereto. It is preferable to include a metal electrode containing magnesium and silver as the cathode.

[0223] Optionally, the organic electroluminescent device further includes a hole blocking layer 340, which is located between the organic light-emitting layer 330 and the electron transport layer 350. The hole blocking layer can adjust the electron transport rate and can block holes from flowing out of the light-emitting layer.

[0224] Specific examples of hole-blocking layers include, but are not limited to, triazine or pyrimidine compounds, as shown below. In one specific embodiment, the hole-blocking layer 340 comprises α-ET-1.

[0225]

[0226] Optionally, such as Figure 1 As shown, an electron injection layer 360 is further disposed between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic substances. For example, the material of the electron injection layer 360 may be selected from one or more of LiF, NaCl, CsF, Li₂O, BaO, Li₂O, NaCl, CsF, Cs₂CO₃, Na, Li, Ca, Al, and Yb. In one specific embodiment, the material of the electron injection layer 360 may include Yb.

[0227] Secondly, this application provides an electronic device that includes the aforementioned organic electroluminescent device.

[0228] like Figure 2 As shown, the electronic device is electronic device 400, which can be a display device, a lighting device, an optical communication device, or other types of electronic devices, such as including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0229] The present application will now be described in detail with reference to embodiments. However, the following description is intended to explain the present application and not to limit the scope of the present application in any way.

[0230] Synthesis Examples

[0231] Those skilled in the art will recognize that the chemical reactions described in this application can be suitably used to prepare many other compounds of this application, and other methods for preparing the compounds of this application are considered to be within the scope of this application. For example, the synthesis of those non-illustrative compounds according to this application can be successfully accomplished by those skilled in the art through modification methods, such as appropriately protecting interfering groups, utilizing other known reagents besides those described in this application, or making some conventional modifications to the reaction conditions. Additionally, the synthesis of anti-compounds disclosed in this application...

[0232] (I) Compounds of formula I can be prepared according to analogous synthesis procedures, which are exemplified below with the preparation of the following compounds.

[0233] Synthesis of intermediate A

[0234]

[0235] Under N2protection, 9-(3-bromophenyl)-9-phenylfluorene (0.056 mol, 22.2 g), 4- aminodimethylfluorene (0.056 mol, 11.7 g), toluene (160 mL) were added into a 250 mL three-necked round-bottom flask, stirred at reflux for 30 min, cooled to 70-80 °C, t-BuONa (0.084 mol, 8.07 g), x-Phos (0.001 mol, 0.53 g), Pd2(dba)3(0.0005 mol, 0.4576 g) were added, after the system temperature stabilized, refluxed for 4 hours, stopped the reaction, after the reaction liquid cooled to room temperature, 100 mL deionized water was added, extracted with toluene / water, and the organic phase was washed to neutral, added anhydrous magnesium sulfate to remove water for 30 min, filtered and concentrated, and then eluted with a silica gel column using EA (ethyl acetate): n-heptane (n-heptane) = 1:10 (volume ratio) as the eluent to obtain intermediate MA-1 (23.5 g, yield 79.9%) in the form of a white solid.

[0236] Referring to the synthesis procedure of intermediate MA-1, intermediate MA-1X, MB-X, MC-X, MD-1 were prepared by replacing raw material 2 with 4-aminodimethylfluorene and raw material 3 with 9-(3-bromophenyl)-9-phenylfluorene, wherein the number of the intermediate, the corresponding raw material, the structure and the synthesis yield are shown in Table 1:

[0237] Table 1

[0238]

[0239]

[0240] Synthesis of compound 1

[0241]

[0242] In a 250 mL three necked round bottom flask, under N2, intermediate MA-1 (15.98 g, 30.4 mmol), bromobenzene (4.77 g, 30.4 mmol), toluene (100 mL), stirred at reflux, the solution dissolved to clear, cooled to 70-80 °C, added sodium tert-butoxide (4.4 g, 45.7 mmol), s-Phos (0.25 g, 0.61 mmol), Pd2(dba)3(0.28 g, 0.330 mmol), refluxed for 6 h, stopped the reaction, allowed the reaction temperature to cool to room temperature, extracted the reaction with toluene, deionized water, washed to neutral, added anhydrous magnesium sulfate to remove water, passed through a column using DCM: n-Heptane = 1:4 as eluent, concentrated the columnate, recrystallized with toluene and n-Heptane, filtered to get white product, compound A-1 (15.5 g, 84.7% yield). LC-MS (ESI, pos.ion), m / z: 602.28 [M+H] + .

[0243] Referring to the procedure for synthesis of compound A-1, intermediate X was used in place of intermediate MA-1 and raw material 4 was used in place of bromobenzene to prepare compounds, wherein the compound number, raw material, structure, synthesis yield and mass spectrometry characterization are shown in Table 2.

[0244] Table 2

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255] Synthesis of compound A-131

[0256]

[0257] Under the protection of nitrogen, 2-bromo-biphenyl (123 g, 530 mmol) and THF (852 mL) were weighed into a 2 L three-necked round-bottom flask, dissolved to be clear, and then cooled to -80 to -90 °C. n-BuLi (2.5 M, 254.75 mL) was added dropwise to the reaction system slowly. After constant temperature reaction at -80 to -90 °C for 50 min, (3-chloro-5-methylphenyl) phenyl methanone (122.2 g, 530 mmol) was weighed, dissolved in THF (260 mL), and then added dropwise to the reaction system slowly. After constant temperature reaction at -80 to -90 °C for 1 h, the reaction was completed. The reaction solution was naturally warmed to room temperature, poured into 5% hydrochloric acid to pH < 7, stirred thoroughly, extracted with DCM, and then the organic phases were combined, washed with water to neutral, dried with anhydrous magnesium sulfate, filtered, and then the solvent was removed under reduced pressure. The obtained oil was added to a flask containing n-heptane, heated to reflux to be a clear solution, recrystallized at -20 °C, and then a white solid intermediate M-1 (79.4 g, yield 39%) was obtained.

[0258]

[0259] Under the protection of nitrogen, intermediate M-1 (138.6 g, 360 mmol) and glacial acetic acid (1.5 L) were weighed, and stirred at 50 to 60 °C. After the reaction solution was completely clear, concentrated sulfuric acid (3.08 mL) was added dropwise. The temperature was continuously increased to 70 to 80 °C, and stirred for 30 min. The reaction solution was naturally cooled to room temperature, poured into deionized water (2 L), stirred thoroughly, and then filtered. The filter cake was washed with deionized water to neutral, placed in a vacuum drying oven, and dried for 1 h. The filter cake was dissolved in DCM, dried with anhydrous sodium sulfate for 30 min, filtered, and then the solvent was removed under reduced pressure. The crude product was recrystallized with n-heptane and DCM at -20 °C, filtered, and then dried in a vacuum drying oven to obtain a white solid intermediate M-2 (120 g, yield 91%).

[0260]

[0261] Intermediate M-2 (11.15 g, 30.4 mmol), N-[1,1 '-biphenyl-4-yl]-9,9-dimethyl-9H- fluoren-2-amine (10.98 g, 30.4 mmol), toluene (100 mL) were added into a 250 mL three-necked round bottom flask under N2protection, stirred at reflux, the solution was dissolved to be clear, the temperature was adjusted to 70-80 °C, sodium tert-butoxide (4.4 g, 45.7 mmol), s-Phos (0.25 g, 0.61 mmol), Pd2(dba)3(0.28 g, 0.330 mmol) were added, the reaction was carried out at reflux for 6 h, the reaction was stopped, and the reaction temperature was allowed to cool to room temperature, and the reaction solution was extracted with toluene and deionized water, and the organic phase was washed with water until it was neutral, then anhydrous magnesium sulfate was added to remove water, and the product was purified by silica gel column with DCM: n-heptane (v / v) = 1 :4 as eluent, and then concentrated, recrystallized with toluene and n-heptane, and filtered to obtain white product, i.e. compound A-131 (17.8 g, yield 84.7%). LC-MS (ESI, pos.ion), m / z: 692.32 [M+H] + The NMR data of some of the compounds are shown in Table 3 below:

[0262] Table 3:

[0263]

[0264] (2) The second host compounds can be prepared according to similar synthesis processes, and the following preparation of a compound is taken as an example.

[0265] Synthesis of intermediate D-1-a:

[0266]

[0267] 2-bromocarbazole (30.0 g, 121.8 mmol), iodobenzene (24.8 g, 78.03 mmol), CuI (4.64 g, 24.3 mmol), K2CO3(37.0 g, 268.1 mmol), 18-crown-6 (3.2 g, 12.1 mmol) were added into a three-necked flask, and dry DMF (300 mL) solvent was added, and the temperature was raised to 150 °C under nitrogen protection, and the temperature was kept stirring for 17 h; cooled to room temperature, stopped stirring, and the organic phase was separated after the reaction solution was washed with water, dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography with dichloromethane / n-heptane as the mobile phase to obtain white solid product intermediate D-1-a (26.3 g, 67%).

[0268] Preparation of intermediate MD-1-b

[0269]

[0270] Intermediate D-1-a (26.0 g, 80.6 mmol), o-chloroaniline (11.3 g, 88.7 mmol), Pd2(dba)3(0.73 g, 0.8 mmol), x-phos (0.76 g, 1.6 mmol), sodium tert-butoxide (11.6 g, 121.0 mmol) were added into a three-necked flask, and toluene (300 mL) was added as solvent, and the temperature was raised to 110 °C under nitrogen protection, and the temperature was kept for 15 hours with stirring; after cooling to room temperature, the stirring was stopped, and the organic phase was separated after the reaction solution was washed with water, dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain white solid product intermediate MD-1-b (15.7 g, yield 53%).

[0271]

[0272] Preparation of intermediate MD-1

[0273] Intermediate MD-1-b (15.0 g, 46.5 mmol), cesium carbonate (37.9 g, 116.3 mmol), tricyclohexylphosphine fluoroborate (8.5 g, 23.2 mmol), Pd2(dba)3(0.52 g, 2.3 mmol) were added into a three-necked flask, and toluene (150 mL) was added as solvent, and the temperature was raised to 110 °C under nitrogen protection, and the temperature was kept for 10 hours with stirring; after cooling to room temperature, the stirring was stopped, and the organic phase was separated after the reaction solution was washed with water, dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain white solid product intermediate MD-1 (9.43 g, yield 61%).

[0274] Referring to the synthesis process of intermediate MD-1, intermediate D-X was prepared by replacing raw material 5 with 2-bromocarbazole, raw material 6 with iodobenzene, and raw material 7 with o-chloroaniline, wherein the number, raw material, intermediate structure, and synthesis yield of intermediate D-X are shown in Table 4:

[0275] Table 4

[0276]

[0277] Synthesis of compound B-81

[0278]

[0279] Intermediate MD-7 (12.76 g, 27.0 mmol), 4-bromobiphenyl (6.32 g, 27.0 mmol), tris(dibenzylideneacetone)dipalladium (0.2 g, 0.3 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-biphenyl (0.2 g, 0.5 mmol), sodium tert-butoxide (5.2 g, 154.1 mmol) were added into a three-necked flask, and toluene (300 mL) was added as solvent, and the mixture was heated to 110 °C under nitrogen protection, and stirred for 15 hours at the same temperature; after cooling to room temperature, the stirring was stopped, and the organic phase was separated after the reaction solution was washed with water, dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain white solid product B-81 (10.98 g, yield 64%); mass spectrum: m / z = 625.22 [M+H] + .

[0280] The synthesis of compound B-81 was carried out by replacing intermediate MD-7 with intermediate MD-X, and raw material 8 with 4-bromobiphenyl, wherein the raw material, the number and structure of the compound, the synthesis yield and characterization are shown in Table 5:

[0281] Table 5

[0282]

[0283]

[0284] (3) The compounds of formula II can all be prepared according to similar synthesis processes, and the following preparation of compounds is taken as an example.

[0285] Synthesis of compound C-1

[0286]

[0287] Under N2 protection, weigh out the following raw materials: R-1 (CAS: 2085325-18-2) (12.6 g, 0.03 mol), R-2 (CAS: 1883265-32-4) (10.7 g, 0.03 mol), potassium carbonate (8.2 g, 0.06 mol), TBAB (0.97 g, 0.003 mol), Pd(PPh3)4 (0.35 g, 0.0003 mol), toluene (60 mol), and anhydrous ethanol (3 g, 0.003 mol). 0 mL of deionized water (10 mL) was added to a 250 mL three-necked round-bottom flask. The mixture was refluxed and stirred for 4 h. TLC analysis showed that the reaction was complete, and the reaction was stopped. The mixture was allowed to cool to room temperature. The reaction solution was extracted with water and toluene. The organic phase was washed with water until neutral. Anhydrous sodium sulfate was added to remove water. The mixture was filtered and concentrated. The solution was purified by column chromatography using DCM:n-heptane (v / v) = 1:3 to give a white solid product, compound C-1 (12.7 g, yield 69%). Mass spectrometry: m / z = 617.19 M + H. + .

[0288] The compound was synthesized according to the reaction route of compound C-1, with reactant 9 replacing reactant R-1 and reactant 10 replacing reactant R-2. The compound numbers, reactants, structures, synthesis yields and characterizations are shown in Table 6.

[0289] Table 6

[0290]

[0291]

[0292]

[0293] Fabrication and Evaluation Examples of Organic Electroluminescent Devices

[0294] Example 1: Red Organic Electroluminescent Device

[0295] First, anodizing pretreatment is performed through the following process: [The process is repeated in the original text, so the translation is incomplete.] On the ITO / Ag / ITO substrate, surface treatment is performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. Organic solvents are used to clean the surface of the ITO substrate to remove impurities and oil stains.

[0296] HAT-CN was vacuum-deposited on the experimental substrate (anode) to form a thickness of [thickness value missing]. A hole injection layer (HIL) is formed, and compound HT-17 is vacuum-deposited onto the hole injection layer to form a thickness of [missing information]. The hole transport layer.

[0297] Compound A-1 was vacuum-deposited onto the hole transport layer to form a layer with a thickness of [missing information]. Hole adjustment layer.

[0298] Then, compound C-3 was used as the first host and compound B-33 as the second host, and the two were mixed at a weight ratio of 6:4 to form a hybrid host. On the hole adjustment layer, the hybrid host and dopant Ir(dmpq)2(acac) were co-vacuum-deposited at a deposition rate ratio of 95%:5% to form a layer with a thickness of [missing information]. Organic light-emitting layer (EML).

[0299] Next, compound a-ET-1 was vacuum-deposited onto the organic light-emitting layer to form a layer with a thickness of [missing information]. A hole-blocking layer was formed; and on the hole-blocking layer, compounds ET-17 and LiQ were co-deposited at a weight ratio of 50%:50% to form a thickness of [missing information]. The electron transport layer (ETL) is formed by depositing Yb onto the electron transport layer to create a thickness of [thickness value missing]. An electron-injected layer (EIL) was formed, and then magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:9 and vacuum-deposited onto the electron-injected layer to form a layer with a thickness of [missing information]. The cathode.

[0300] Furthermore, CP-1 is deposited on the aforementioned cathode to form a thickness of [missing information]. The capping layer (CPL) is then applied to complete the fabrication of the red organic light-emitting device.

[0301]

[0302]

[0303] Examples 2-67

[0304] Except that when forming the mixed body of hole adjustment layer and light emission layer, the compounds listed in Table 7 below are used instead of the compounds used in Example 1, a red organic electroluminescent device is fabricated using the same method as in Example 1.

[0305] Comparative Example 1

[0306] Except that, when forming the light-emitting layer substrate, compound S-RH-1 from Table 7 below is used instead of the mixed substrate used in Example 1, a red organic electroluminescent device is fabricated using the same method as in Example 1.

[0307] Comparative Example 2

[0308] Except that, when forming the hybrid host of the light-emitting layer, compound C-39 from Table 7 is used in combination with compound RP-1 instead of the compound used in Example 1, a red organic electroluminescent device is fabricated using the same method as in Example 1.

[0309] Comparative Example 3

[0310] A red organic electroluminescent device was produced using the same method as in Example 1 except that Compound EB-1 in Table 7 below was used instead of Compound A-1 used in Example 1 when forming the hole adjusting layer.

[0311] Comparative Example 4

[0312] A red organic electroluminescent device was produced using the same method as in Example 1 except that Compound EB-2 in Table 7 below was used instead of Compound A-1 used in Example 1 when forming the hole adjusting layer.

[0313] Comparative Example 5

[0314] A red organic electroluminescent device was produced using the same method as in Example 1 except that no hole adjusting layer was provided in the device.

[0315] Comparative Example 6

[0316] A red organic electroluminescent device was produced using the same method as in Example 1 except that Compound C-3 was used instead of the mixed host used in Example 1 when forming the light-emitting layer host.

[0317] The structures of the compounds in the comparative examples are as follows:

[0318]

[0319] The red organic electroluminescent devices produced in Examples 1 to 67 and Comparative Examples 1 to 6 were tested for performance, specifically the IVL performance of the devices was tested under the condition of 10 mA / cm 2 , and the T95 device lifetime was tested under the condition of 20 mA / cm 2 . The test results are shown in Table 7 below.

[0320] Table 7

[0321]

[0322]

[0323]

[0324]

[0325] As can be seen from Table 7 above, compared with Comparative Examples 1 to 6, the luminous efficiency of the devices of Examples 1 to 67 was improved by at least 16% overall, and the T 95 95 device lifetime was improved by at least 14%.

[0326] In Comparative Example 1, the light-emitting layer host material of the device used compound SRH-1 as a single host, compared with Examples 1-67, the light-emitting efficiency and T95 lifetime of the device were decreased, wherein the light-emitting efficiency was decreased by at least 30%, and the service life was decreased by at least 28%. In Comparative Example 2, the light-emitting layer host of the device still used a mixed host, and the P-type host therein was replaced with compound RP-1, compared with Examples 1-67, the light-emitting efficiency and T95 lifetime of the device were decreased, wherein the light-emitting efficiency was decreased by at least 16%, and the service life was decreased by at least 14%. Therefore, it can be seen that when the hole adjusting layer of the device is a compound of Formula I, the light-emitting layer host material is matched with the compounds of Formula II and Formula III of the present application, which can significantly improve the light-emitting efficiency and service life of the device.

[0327] In Comparative Examples 3-5, after the hole adjusting layer material was replaced by the mixed compounds of Formula II and Formula III, the light-emitting performance of the device was also significantly decreased. It can be verified that when the compound of Formula I of the present application is used as the hole adjusting layer, and the compounds of Formula II and Formula III of the present application are used as the light-emitting layer mixed host material, such matching can significantly improve the light-emitting efficiency and service life of the organic electroluminescent device.

Claims

1. An organic electroluminescence device comprising, in the stated order, an anode, a hole injection layer, a hole transport layer, an organic light-emitting layer, an electron transport layer, an electron injection layer, and a cathode, wherein a hole adjustment layer is further provided between the hole transport layer and the organic light-emitting layer, and the hole adjustment layer comprises a compound represented by Formula I: wherein: L is selected from a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group; Ar is selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group; each substituent in Ar is independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, or phenyl; or, in Ar, any two adjacent substituents form a benzene ring or a fluorene ring; each substituent in L is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, or phenyl; each of R1, R2, R3, R4, R5, and R6 is the same or different, and is independently selected from deuterium, methyl, ethyl, isopropyl, or tert-butyl; the organic light-emitting layer is composed of a light-emitting layer host and a dopant, the light-emitting layer host comprises a first host compound and a second host compound, and the first host compound has a structure represented by Formula II-1: wherein: Z is selected from O or S; R8 is selected from the group consisting of: L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group; each substituent in L1 and L2 is independently selected from deuterium, cyano, trideuteromethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, or phenyl; Ar1 is selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group; Ar2 is selected from hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group; each substituent in Ar1 and Ar2 is independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteromethyl, methyl, ethyl, isopropyl, tert-butyl, or phenyl; the second host compound is selected from the following structures III-3 to III-9: L4 is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group; each substituent in L4 is independently selected from deuterium, fluorine, cyano, trideuteromethyl, methyl, ethyl, isopropyl, tert-butyl, or phenyl; Ar is selected from the group consisting of: the compound represented by Formula I is selected from the group consisting of: wherein ​ ​ ​ ​ ​ R1~R6 are represented by R i n1~n6 are represented by n i i is a variable, representing 1, 2, 3, 4, 5 or 6, n1, n2, n3, n4, n5 and n6 represent the number of R1, R2, R3, R4, R5 and R6, respectively; wherein, when i is 1, n i is selected from 0, 1, 2, or 3; when i is 2, 4, 5, or 6, n i is selected from 0, 1, 2, 3, or 4; when i is 3, n i is selected from 0, 1, 2, 3, 4, or 5, any two of n i are the same or different; ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Ar3and R 11 each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl; Ar3and R 11 each independently is selected from deuterium, fluorine, cyano, trideuteromethyl, methyl, ethyl, isopropyl, tert-butyl, or phenyl; or, in Ar3and R 11 any two adjacent substituents form a fluorene ring.

2. The organic electroluminescent device according to claim 1, wherein ​ 3. The organic electroluminescent device according to claim 1, wherein ​ 4. The organic electroluminescent device according to claim 1, wherein Ar1is selected from the group consisting of:

5. The organic electroluminescent device according to claim 1, wherein The first host compound is selected from the group consisting of:

6. The organic electroluminescent device according to claim 1, wherein Ar3is selected from the group consisting of:

7. The organic electroluminescent device according to claim 6, characterized in that R 11 selected from the group consisting of:

8. The organic electroluminescent device according to claim 1, wherein The second host compound is selected from the group consisting of:

9. The organic electroluminescent device according to claim 1, wherein The mass ratio of the first host compound to the second host compound in the organic light-emitting layer is 30:70-70:

30.

10. An electronic device, characterized by The organic electroluminescent device according to any one of claims 1-9.

Images