WO2024078137A1

WO2024078137A1 - Organic electroluminescent device and electronic apparatus

Info

Publication number: WO2024078137A1
Application number: PCT/CN2023/113869
Authority: WO
Inventors: 徐先彬; 张孔燕; 张鹤鸣
Original assignee: 陕西莱特光电材料股份有限公司
Priority date: 2022-10-09
Filing date: 2023-08-18
Publication date: 2024-04-18
Also published as: CN117412652A

Abstract

An organic electroluminescent device and an electronic apparatus. The organic electroluminescent device comprises a cathode, an anode, and an organic layer, the organic layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises a first compound and a second compound. The first compound is selected from compounds represented by formula 1, and the second compound is selected from compounds represented by formula 2 or formula 3.

Description

Organic electroluminescent device and electronic device

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims priority to Chinese patent application No. CN202211226718.3 filed on October 9, 2022. The full text of the above-mentioned Chinese patent application is hereby cited as part of this application.

Technical Field

The present application relates to the technical field of organic electroluminescent materials, and in particular to an organic electroluminescent device and an electronic apparatus.

Background technique

In recent years, organic electroluminescent devices (OLEDs) have become a very popular emerging flat-panel display product both at home and abroad. This is because OLED displays have the characteristics of self-luminescence, wide viewing angle, short response time, high efficiency, and wide color gamut.

An organic electroluminescent device (OLED) generally includes an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer may include a hole injection layer, a hole transport layer, a hole auxiliary layer, an electron blocking layer, a light-emitting layer (containing a host and a dopant material), a hole blocking layer, 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 are in an excited state and release energy outward, thereby causing the light-emitting layer to emit light outward.

At present, there are still problems of poor performance in the use of organic electroluminescent devices, such as excessively high driving voltage, low luminous efficiency or short life, which all affect the use field of organic electroluminescent devices. Therefore, it is still necessary to conduct further research in this field to improve the performance of organic electroluminescent devices.

Summary of the invention

In view of the above problems existing in the prior art, the purpose of the present application is to provide an organic electroluminescent device and an electronic device to improve the performance of the device and the device.

According to a first aspect of the present application, there is provided an organic electroluminescent device, comprising a cathode, an anode and an organic layer;

Wherein, the cathode and the anode are arranged opposite to each other;

The organic layer is located between the cathode and the anode;

The organic layer includes an organic light-emitting layer;

The organic light-emitting layer includes a first compound and a second compound;

The first compound has a structure shown in Formula 1:

wherein, Z ₁ , Z ₂ and Z ₃ are each independently selected from N or C(H), and at least one of Z ₁ to Z ₃ is N;

Y is selected from S or O;

One of _X1 and _X2 is -N=, and the other is O or S;

Ring A is selected from a naphthalene ring or a phenanthrene ring;

L ₁ , L ₂ and L ₃ are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

Ar ₁ , Ar ₂ and Ar ₃ are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

The substituents in L ₁ , L ₂ , L ₃ , Ar ₁ , Ar ₂ and Ar ₃ are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, aryloxy group having 6 to 20 carbon atoms or arylthio group having 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;

Each R ₁ is the same or different and is independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms; n ₁ represents the number of R ₁ ; n ₁ is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;

The second compound has a structure shown in Formula 2 or Formula 3:

One of _X3 and _X4 is -N=, and the other is O or S;

L ₄ , L ₅ and L ₆ are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

Ar ₄ , Ar ₅ and Ar ₆ are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

The substituents in L ₄ , L ₅ , L ₆ , Ar ₄ , Ar ₅ and Ar ₆ are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, aryloxy group having 6 to 20 carbon atoms or arylthio group having 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;

Each _R2 is the same or different and is independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms; _n2 represents the number of _R2 ; _n2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

Ring C and Ring E are each independently selected from an aromatic ring having 6 to 14 carbon atoms;

_L7 and _L8 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

Ar ₇ and Ar ₈ are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

The substituents in L ₇ , L ₈ , Ar ₇ and Ar ₈ are the same or different and are independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 20 carbon atoms or arylthio having 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;

Each R ₃ , R ₄ and R ₅ is the same or different and is independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent R ₄ groups form a ring; n ₃ represents the number of R ₃ , n ₄ represents the number of R ₄ , and n 5 represents the number of R ₅ ; n ₃ and n ₅ are independently selected from 0, 1, 2, 3, 4, ₅ or 6; n ₄ is selected from 0, 1 or 2.

According to a second aspect of the present application, an electronic device is provided, comprising the organic electroluminescent device according to the first aspect.

The light-emitting layer host material of the organic electroluminescent device of the present application includes the first compound and the second compound, and the first compound has a structure in which the parent nucleus of benzodibenzofuran/thiophene and oxazole/thiazole fused electron transport groups is connected, and has strong electron transport properties, and the second compound is selected from indole carbazole compounds or phenanthroline oxazole/thiazole parent nucleus with hole transport properties, and the two are mixed into red light host materials. First, the hole transport material and the electron transport material used in the present application have a relatively large conjugated area, and the first excited triplet energy level of the compound can be reduced on the one hand, and the molecular action between the hole transport material and the electron transport material can be enhanced on the other hand, and the exciplex can be formed more effectively, and the carrier mobility is improved, so as to improve the energy transfer efficiency of the host material to the luminescent material, and finally improve the luminous efficiency of the device. Secondly, in the first compound used in the present application, the parent nucleus is connected to the electron transport group in the parent nucleus, and the LUMO (lowest empty orbital) electron cloud distribution of the compound can be limited to benzodibenzofuran/thiophene and oxazole/thiazole parts, and the attack of the exciton on the C-N bond in the aromatic amine is suppressed, so as to improve the life of the device.

BRIEF DESCRIPTION OF THE DRAWINGS

The accompanying drawings are used to provide further understanding of the present application and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present application, but do not constitute a limitation to the present application.

FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.

FIG. 2 is a schematic diagram of the structure of an electronic device according to an embodiment of the present application.

Reference numerals

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. Electron transport layer

350. Electron injection layer 400. Electronic device

Detailed ways

Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in a variety of forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that the present application will be more comprehensive and complete and the concepts of the exemplary embodiments are fully conveyed to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, many specific details are provided to provide a full understanding of the embodiments of the present application.

In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals in the drawings represent the same or similar structures. structures, and thus their detailed description will be omitted.

In a first aspect, the present application provides an organic electroluminescent device, comprising a cathode, an anode and an organic layer;

Wherein, the cathode and the anode are arranged opposite to each other;

The organic layer is located between the cathode and the anode;

The organic layer includes an organic light-emitting layer;

The first compound has a structure shown in Formula 1:

Y is selected from S or O;

One of _X1 and _X2 is -N=, and the other is O or S;

Ring A is selected from a naphthalene ring or a phenanthrene ring;

The second compound has a structure shown in Formula 2 or Formula 3:

One of _X3 and _X4 is -N=, and the other is O or S;

Ar ₄ , Ar ₅ and Ar ₆ are the same or different and are independently selected from substituted or unsubstituted aryl groups, carbon atoms and A substituted or unsubstituted heteroaryl group having 3 to 40 substituents;

In the present application, the terms "optionally" and "optionally" mean that the event or environment described subsequently may or may not occur. For example, "optionally, any two adjacent substituents form a saturated or unsaturated 3-15 membered ring" includes: the scenario where any two adjacent substituents form a ring, and the scenario where any two adjacent substituents exist independently and do not form a ring. "Any two adjacent" can include two substituents on the same atom, and can also include two adjacent atoms each having one substituent; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spiro ring with the atom to which they are commonly connected; when there is a substituent on two adjacent atoms each, the two substituents can be fused into a ring.

In the present application, the descriptions "each ... independently is" and "... are independently" and "... are independently" are interchangeable and should be understood in a broad sense, which means that in different groups, the specific options expressed by the same symbols do not affect each other. It can also mean that in the same group, the specific options expressed by the same symbols do not affect each other. For example, Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine, which means: Formula Q-1 indicates that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 indicates that there are q substituents R" on each benzene ring of biphenyl, and 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.

In the present application, the term "substituted or unsubstituted" means that the functional group recorded after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" means an aryl having a substituent Rc or an unsubstituted aryl. The substituent Rc mentioned above may be, for example, deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, halogenated alkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 20 carbon atoms, or arylthio having 6 to 20 carbon atoms. The number of substitutions may be one or more.

In the present application, "plurality" means more than 2, for example, 2, 3, 4, 5, 6, etc.

In the present application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the number of all carbon atoms.

The hydrogen atoms in the structures of the compounds of the present application include various isotope atoms of the hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).

In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl and a condensed ring aryl connected by carbon-carbon bond conjugation, and two or more condensed ring aryl groups connected by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups connected by carbon-carbon bond conjugation can also be regarded as aryl of the present application. Wherein, condensed ring aryl can, for example, include bicyclic condensed aryl (e.g., naphthyl), tricyclic condensed aryl (e.g., phenanthrenyl, fluorenyl, anthracenyl), etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, peryl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Ji et al.

In the present application, the arylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from an aryl group.

In the present application, terphenyl includes

In the present application, the carbon number of the substituted or unsubstituted aryl (arylene) group may be 6, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

In the present application, the fluorenyl group may be substituted by one or more substituents. When the fluorenyl group is substituted, the substituted fluorenyl group may be: etc., but not limited thereto.

In the present application, examples of aryl groups as substituents include, but are not limited to, phenyl, naphthyl, phenanthrenyl, biphenyl, fluorenyl, dimethylfluorenyl, and the like.

In the present application, heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatoms may be one or more of B, O, N, P, Si, Se and S. The heteroaryl may be a monocyclic heteroaryl or a polycyclic heteroaryl. In other words, the heteroaryl group can be a single aromatic ring system or a plurality of aromatic ring systems conjugated via carbon-carbon bonds, and any aromatic ring system is an aromatic monocyclic ring or an aromatic condensed ring. By way of example, the heteroaryl group may include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothiphenyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silyfluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto.

In the present application, the heteroarylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from a heteroaryl group.

In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) 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, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 3 to 30, in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 12 to 18, and in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 5 to 12.

In the present application, the heteroaryl group as a substituent is, for example but not limited to, pyridyl, carbazolyl, dibenzothiophenyl, dibenzofuranyl, benzoxazolyl, benzothiazolyl, and benzimidazolyl.

In the present application, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups 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 haloalkyl group, or the like.

In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms in the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, 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, n-hexyl, and the like.

In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

In the present application, the carbon number of the cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

In the present application, the carbon number of the deuterated alkyl group having 1 to 10 carbon atoms is, for example, 1, 2, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the deuterated alkyl group include, but are not limited to, trideuterated methyl group.

In the present application, the carbon number of the haloalkyl group having 1 to 10 carbon atoms is, for example, 1, 2, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

In the present application, a ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6-membered ring. A 3-15-membered ring refers to a cyclic group having 3-15 ring atoms. Examples of 3-15-membered rings include cyclopentane, cyclohexane, fluorene ring, benzene ring, etc.

In this application, Refers to the chemical bonds that connect to other groups.

In this application, no single bond extending from the ring system is involved in the positioning of the connecting bond. It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that pass through the bicyclic ring. The meaning represented by it includes any possible connection mode shown in formula (f-1) to formula (f-10):

For another example, as shown in the following formula (X'), the dibenzofuranyl represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and the meaning represented by it includes any possible connection mode shown in formula (X'-1) to formula (X'-4):

The non-positioning substituent in the present application refers to a substituent connected by a single bond extending from the center of the ring system, which 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 a non-positioning connection bond, and the meaning represented includes any possible connection mode shown in formula (Y-1) to formula (Y-7):

In some embodiments, in some embodiments, in the first compound, Z ₁ , Z ₂ and Z ₃ are each independently selected from N or C(H), and at least one of Z ₁ to Z ₃ is N.

More specifically, in some embodiments of the present application, in the first compound, _X1 and _X2 are both C(H), and _X3 is N; or _X1 and _X3 are both C(H), _X2 is N, _X2 and _X3 are both C(H), and _X1 is N; or _X1 and _X2 are both N, and _X3 is C(H); or _X1 and _X3 are both N, and _X2 is C(H); or _X2 and _X3 are both N, and _X1 is C(H); or _X1 , _X2 , and _X3 are all N.

In some embodiments, Z ₁ , Z ₂ and Z ₃ are each independently selected from N or C(H), and at least two of Z ₁ to Z ₃ are N; or Z ₁ , Z ₂ and Z ₃ are all N.

In some embodiments, the first compound is selected from the following structures represented by formula (1-1) to formula (1-15):

Wherein, Y is O or S.

In some embodiments, in the first compound, Ar ₁ , Ar ₂ and Ar ₃ are the same or different and are each independently selected from substituted or unsubstituted aryl having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40 carbon atoms; substituted or unsubstituted heteroaryl having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40 carbon atoms.

Optionally, the substituents in Ar ₁ , Ar ₂ and Ar ₃ are the same or different and are independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms or a deuterated aryl group having 6 to 15 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

In some embodiments, in the first compound, Ar ₁ , Ar ₂ and Ar ₃ are the same or different, and are each independently selected from a substituted or unsubstituted group W ₁ ; the unsubstituted group W ₁ is selected from the group consisting of the following groups:

The substituted group _W1 has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzoxazolyl or benzothiazolyl, and when the number of substituents on the group W1 is greater than ₁ , each substituent is the same or different.

In some embodiments, in the first compound, Ar ₁ , Ar ₂ and Ar ₃ are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted peryl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted pyridyl.

Optionally, the substituents in Ar ₁ , Ar ₂ and Ar ₃ are the same or different and are independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl or carbazolyl. Optionally, in Ar ₁ and Ar ₂ , any two adjacent substituents form a benzene ring.

In some embodiments, in the first compound, Ar ₁ and Ar ₂ are the same or different and are each independently selected from the following groups:

Ar ₃ is selected from the following groups:

In some embodiments, in the first compound, The same or different, and each independently selected from the following groups:

In some embodiments, in the first compound, Ar ₁ and Ar ₂ are the same or different and are independently selected from the group consisting of the following groups:

In some embodiments, in the first compound, Ar ₃ is selected from the group consisting of:

In some embodiments, in the first compound, L ₁ , L ₂ and L ₃ are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

Optionally, the substituents in L ₁ , L ₂ and L ₃ are the same or different and are independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 8 carbon atoms, fluoroalkyl having 1 to 4 carbon atoms, deuterated alkyl having 1 to 4 carbon atoms, phenyl or naphthyl.

In some embodiments, in the first compound, L ₁ , L ₂ and L ₃ are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted dibenzothienylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted benzoxazolylene, and a substituted or unsubstituted benzothiazolylene.

Optionally, the substituents in L ₁ , L ₂ and L ₃ are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.

In some embodiments, in the first compound, _L3 is selected from a single bond or the group consisting of the following groups:

In some embodiments, in the first compound, _L1 and _L2 are the same or different, and are each independently selected from a single bond or the group consisting of the following groups:

In some embodiments, in the first compound, each R ₁ is the same or different and is independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl or carbazolyl.

In some embodiments, the second compound is selected from the structures represented by Formula (2-1), Formula (2-2), or Formula (3-1) to Formula (3-20).

In some embodiments, the compound of formula 2 has a structure shown in formula (2-1) or formula (2-2):

In some embodiments, in Formula 2, _Ar4 , _Ar5 and _Ar6 are each independently selected from substituted or unsubstituted aryl having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40 carbon atoms, and substituted or unsubstituted heteroaryl having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40 carbon atoms.

Optionally, the substituents in Ar ₄ , Ar ₅ and Ar ₆ are the same or different and are independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms or a deuterated aryl group having 6 to 15 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

In some embodiments, in Formula 2, Ar ₄ , Ar ₅ and Ar ₆ are the same or different, and are each independently selected from a substituted or unsubstituted group W ₂ ; the unsubstituted group W ₂ is selected from the group consisting of the following groups:

The substituted group _W2 has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl or carbazolyl, and when the number of substituents on the group _W2 is greater than 1, the substituents are the same or different.

In some embodiments, in Formula 2, Ar ₄ , Ar ₅ and Ar ₆ are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted peryl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl.

Optionally, the substituents in Ar ₄ , Ar ₅ and Ar ₆ are the same or different and are each independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl or carbazolyl. Optionally, in Ar ₄ and Ar ₅ , any two adjacent substituents form a benzene ring.

In some embodiments, in Formula 2, Ar ₄ and Ar ₅ are the same or different and are each independently selected from the following groups:

Ar ₆ is selected from the following groups:

In some embodiments, in Formula 2, The same or different, and each independently selected from the following groups:

In some embodiments, in Formula 2, Ar ₄ and Ar ₅ are the same or different and are each independently selected from the group consisting of the following groups:

In some embodiments, in Formula 2, Ar ₆ is selected from the group consisting of the following groups:

In some embodiments, in Formula 2, _L4 , _L5 and _L6 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

Optionally, the substituents in L ₄ , L ₅ and L ₆ are the same or different and are independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 8 carbon atoms, fluoroalkyl having 1 to 4 carbon atoms, deuterated alkyl having 1 to 4 carbon atoms, phenyl or naphthyl.

In some embodiments, in Formula 2, L ₄ , L ₅ and L ₆ are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted dibenzothienylene, a substituted or unsubstituted dibenzofuranylene, or a substituted or unsubstituted carbazolylene.

Optionally, the substituents in L ₄ , L ₅ and L ₆ are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.

In some embodiments, in Formula 2, _L4 is selected from a single bond or the group consisting of the following groups:

In some embodiments, in Formula 2, L ₅ and L ₆ are the same or different, and are each independently selected from a single bond or the group consisting of the following groups:

In some embodiments, in Formula 2, each R ₂ is the same or different and is independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

In some embodiments, the second compound is selected from the following structures represented by formula (3-1) to formula (3-20):

In some embodiments, in Formula 3, Ring C and Ring E are each independently selected from a benzene ring or a naphthalene ring.

In some embodiments, in Formula 3, _L7 and _L8 are the same or different and are independently selected from a single bond, a carbon number of 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 substituted or unsubstituted arylene group, and 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 substituted or unsubstituted heteroarylene group.

Optionally, the substituents in _L7 and _L8 are the same or different and are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a phenyl group or a naphthyl group.

In some embodiments, in Formula 3, _L7 and _L8 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted anthraceneylene, a substituted or unsubstituted dibenzothienylene, a substituted or unsubstituted dibenzofuranylene, or a substituted or unsubstituted carbazolylene.

Optionally, the substituents in _L7 and _L8 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.

In some embodiments, in Formula 3, _L7 and _L8 are the same or different, and are each independently selected from a single bond or the group consisting of the following groups:

In some embodiments, in Formula 3, _Ar7 and _Ar8 are the same or different and are each independently selected from substituted or unsubstituted aryl having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40 carbon atoms, and substituted or unsubstituted heteroaryl having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40 carbon atoms.

In some embodiments, in Formula 3, the substituents in Ar ₇ and Ar ₈ are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, or a deuterated aryl group having 6 to 15 carbon atoms, and optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

In some embodiments, in Formula 3, Ar ₇ and Ar ₈ are the same or different and are each independently selected from a substituted or unsubstituted group W ₃ ; the unsubstituted group W ₃ is selected from the group consisting of the following groups:

The substituted group _W3 has one or more substituents, the substituents are the same or different, and each is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl or carbazolyl, and when the number of substituents on the group _W3 is greater than 1, each substituent is the same or different.

In some embodiments, in Formula 3, Ar ₇ and Ar ₈ are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted peryl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted pyridyl.

Optionally, the substituents in Ar ₇ and Ar ₈ are the same or different and are each independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl or carbazolyl, and optionally, in Ar ₇ and Ar ₈ , any two adjacent substituents form a benzene ring.

In some embodiments, in Formula 3, Ar ₇ and Ar ₈ are the same or different and are each independently selected from the group consisting of the following groups:

In some embodiments, The same or different, and each independently selected from the following groups:

In some embodiments, in Formula 1, each R ₁ is the same or different and is independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

In some embodiments, in Formula 2, each _R2 is the same or different and is independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl or carbazolyl.

In some embodiments, in Formula 3, each R ₃ , R ₄ and R ₅ are the same or different and are independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

In some embodiments, the first compound is selected from the following compounds A-1 to A-276:

In some embodiments, the second compound is selected from the following compounds B1 to B-162 and C-1 to C-104:

The present application also provides a light-emitting layer composition, which comprises a first compound and a second compound, wherein the first compound has a structure shown in Formula 1:

Y is selected from S or O;

One of _X1 and _X2 is -N=, and the other is O or S;

Ring A is selected from a naphthalene ring or a phenanthrene ring;

The substituents in L ₁ , L ₂ , L ₃ , Ar ₁ , Ar ₂ and Ar ₃ are the same or different and are independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, halogenated alkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, alkyl having 3 to 12 carbon atoms, trialkylsilyl, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 20 carbon atoms or arylthio having 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;

The second compound has a structure shown in Formula 2 or Formula 3:

One of _X3 and _X4 is -N=, and the other is O or S;

The substituents in L ₇ , L ₈ , Ar ₇ and Ar ₈ are the same or different and are independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, halogenated alkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, trioxane having 3 to 12 carbon atoms, alkylsilyl, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 20 carbon atoms or arylthio having 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;

Optionally, the mass ratio of the first compound to the second compound in the light-emitting layer composition 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.

The present application also provides use of the light-emitting layer composition in a light-emitting layer of an organic electroluminescent device.

The present application also provides an organic electroluminescent device comprising the composition.

The organic electroluminescent device provided in the present application comprises an anode and a cathode arranged opposite to each other, the cathode, the anode and an organic layer. The organic layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises a first compound and a second compound.

Furthermore, the organic light-emitting layer comprises a host material and a dopant. The host material comprises a first compound and a second compound. Generally, based on the total weight of the two compounds, the mass ratio of the first compound to the second compound is 1:99 to 99:1, preferably 10:90 to 90:10, further preferably 30:70 to 70:30, and more preferably 40:60 to 60:40.

In some embodiments, the mass ratio of the first compound (the compound of Formula 1) to the second compound (the compound of Formula 2) in the light-emitting layer host of the organic electroluminescent device is 30:70 to 70:30.

Optionally, in the host material, the mass ratio of the first compound (the compound of Formula 1) to the second compound (the compound of Formula 2) is 35:65, 40:60, 45:55, 50:50, 55:45, 60:40, or 65:35.

In order to obtain the host material mixture, the first compound and the second compound may be placed in an oscillator and mixed to obtain a mixture of a desired weight ratio.

In order to form each layer constituting the organic electroluminescent device of the present application, a dry film-forming method such as vacuum deposition, sputtering, plasma, ion plating method, etc., or a wet film-forming method such as inkjet printing, nozzle printing, slit coating, spin coating, dip coating, flow coating method, etc. can be used.

In addition, the first compound and the second compound can be subjected to film formation in the above-listed methods, usually by a co-evaporation method or a hybrid evaporation method. Co-evaporation is a hybrid deposition method in which two or more materials are placed in a corresponding single crucible source and current is applied to multiple chambers simultaneously to evaporate the materials. Hybrid evaporation is a hybrid deposition method in which two or more materials are mixed in one crucible source before evaporation and current is applied to the chambers to evaporate the materials.

In some embodiments of the present application, the organic electroluminescent device is a phosphorescent device.

In some specific embodiments of the present application, the organic electroluminescent device is a green organic electroluminescent device or a red organic electroluminescent device.

In some embodiments of the present application, the organic electroluminescent device includes an anode (e.g., ITO/Ag/ITO substrate), a hole transport layer, a hole adjustment layer, an organic light emitting layer, an electron transport layer, an electron injection layer, a cathode (e.g., a Mg-Ag mixture), and an organic covering layer in sequence. The hole transport layer is located between the anode and the organic light emitting layer, and the hole adjustment layer is located between the hole transport layer and the organic light emitting layer.

According to a specific embodiment, as shown in FIG. 1 , the organic electroluminescent device includes an anode 100, a hole injection layer 310, a hole transport layer 321, a hole adjustment layer (also called a hole auxiliary layer) 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350 and a cathode 200 which are stacked in sequence.

In the present application, the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys. Gold; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined metals and oxides such as ZnO:Al or SnO ₂ :Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole and polyaniline, but not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as an anode is included.

In the present application, the hole transport layer or the hole adjustment layer may include one or more hole transport materials, respectively. The hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, and may be specifically selected from the following compounds or any combination thereof:

In one embodiment, the hole transport layer 321 is composed of HT-1 or HT-5.

In one embodiment, the hole-regulating layer 322 is composed of HT-2 or HT-1.

Optionally, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and the present application does not impose any particular limitation thereto. The material of the hole injection layer 310 may be selected from the following compounds or any combination thereof, for example;

In one embodiment of the present application, the hole injection layer 310 consists of PD and HT-1 or PD and HT-5.

Optionally, the organic light-emitting layer 330 may include the host material and the guest material. Optionally, the organic light-emitting layer 330 is composed of the host material and the guest material, and the holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 may be recombined in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

The host material of the organic light emitting layer 330 includes the first compound and the second compound.

The guest material of the organic light-emitting layer 330 can be a compound having a condensed aromatic ring or a derivative thereof, a compound having a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other materials, and the present application does not impose any special restrictions on this. The guest material is also called a doping material or a dopant. According to the type of light emission, it can be divided into a fluorescent dopant and a phosphorescent dopant. For example, specific examples of the phosphorescent dopant include, but are not limited to,

In one embodiment of the present application, the organic electroluminescent device is a red organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 is composed of the first compound and the second compound. The guest material may be RD-1, for example.

In another embodiment, the organic electroluminescent device is a green organic electroluminescent device. In the embodiment, the host material of the organic light emitting layer 330 is composed of the first compound and the second compound. The guest material may be, for example, fac-Ir(ppy) ₃ .

The electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from but not limited to BmPyPhB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, triazine derivatives and other electron transport materials, and this application does not specifically limit this. The material of the electron transport layer 340 includes LiQ and other electron transport materials, and the other electron transport materials may be selected from but not limited to the following compounds:

In one embodiment of the present application, the electron transport layer 340 is composed of ET-1 and LiQ.

In the present application, the cathode 200 includes a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multilayer materials such as LiF/Al, Liq/Al, LiO ₂ /Al, LiF/Ca, LiF/Al and BaF ₂ /Ca. Optionally, a metal electrode containing magnesium and silver is included as the cathode.

Optionally, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include a complex of an alkali metal and an organic substance. In one embodiment of the present application, the electron injection layer 350 includes ytterbium (Yb).

The present application not only provides the organic electroluminescent device comprising the compound represented by Formula 1 and the compound represented by Formula 2 for the organic light emitting layer, but also provides an electronic device comprising the organic electroluminescent device of the present application.

According to one embodiment, as shown in Fig. 2, the provided electronic device is an electronic device 400. The electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as but not limited to a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.

The synthesis methods of the first compound and the second compound of the present application are specifically described below in conjunction with the synthesis examples, but the present application is not limited thereto.

Synthesis Example

Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many of the heterocyclic compounds of the present invention, and that other methods for preparing the compounds of the present invention are considered to be within the scope of the present invention. For example, the synthesis of the compounds not exemplified herein can be successfully accomplished by those skilled in the art by modification methods, such as appropriate protection of interfering groups, by utilizing other known reagents in addition to those described herein, or by making some conventional modifications to the reaction conditions. The compounds for which the synthesis methods are not mentioned in the present invention are all raw materials obtained from commercial sources.

Synthesis of the first compound:

Synthesis of 7-bromo-1-iodo-2-naphthol:

Under nitrogen atmosphere, 7-bromo-1-iodo-2-naphthylamine (CAS: 2411719-24-7, 17.40 g, 50 mmol), concentrated hydrochloric acid (25 mL) and deionized water (25 mL) were added to a 1000 mL three-necked flask in sequence, and the system was cooled to 0°C with an ice-water bath. An aqueous solution (25 mL) of sodium nitrite (3.45 g, 50 mmol) was added dropwise to the system. After the addition was completed, an aqueous solution (25 mL) of potassium thiocyanate (9.72 g, 100 mmol) and ferric chloride (4.1 g, 25 mmol) were added dropwise to the reaction system. After the addition was completed, the system was slowly heated to room temperature and stirred to react overnight. The reaction solution was poured into deionized water (200 mL), extracted with dichloromethane (100 mL × 3 times), the organic phases were combined and dried with anhydrous sodium sulfate, filtered, and the solvent was removed by reduced pressure distillation to obtain a crude product, which was directly used in the next step without purification.

Under nitrogen atmosphere, add the obtained crude product, sodium sulfide nonahydrate (9.61g, 100mmol), ethanol (180mL) and deionized water (360mL) to a 1000mL three-necked flask at once, heat to reflux and stir to react for 16h. After the reaction system is cooled to room temperature, filter, acidify the filtrate with 1M hydrochloric acid to pH = 2, then extract with dichloromethane (100mL×3 times), combine the organic phases and dry with anhydrous sodium sulfate, filter and remove the solvent by vacuum distillation to obtain a crude product; use n-heptane as the mobile phase to purify the crude product by silica gel column chromatography to obtain a white solid (8.03g, yield 44%). Synthesis of Sub-a1:

Under nitrogen atmosphere, 7-bromo-2-phenylbenzoxazole (CAS: 1268137-13-8, 12.06 g, 44 mmol), bipyraclostrobin (12.28 g, 48.4 mmol), potassium acetate (9.50 g, 96.8 mmol) and 1,4-dioxane (120 mL) were added to a 500 mL three-necked flask in sequence. Stirring and heating were started. When the system was heated to 40° C., tris(dibenzylideneacetone)dipalladium (Pd ₂ (dba) ₃ , 0.40 g, 0.44 mmol) and (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (XPhos, 0.42 g, 0.88 mmol) were quickly added. The temperature was continued to rise to reflux and the reaction was stirred overnight. After the system was cooled to room temperature, 200 mL of water was added to the system, and the mixture was stirred for 30 min. The mixture was filtered under reduced pressure. The filter cake was washed with deionized water until neutral, and then rinsed with 100 mL of anhydrous ethanol. The filter cake was collected to obtain a gray solid. The crude product was slurried once with n-heptane, dissolved with 200 mL of toluene, and then passed through a silica gel column to remove the catalyst. After concentration, a white solid Sub-a1 (10.17 g, yield 72%) was obtained.

Referring to the synthesis of Sub-a1, reactant A shown in Table 1 was used instead of 7-bromo-2-phenylbenzoxazole to synthesize Sub-a2 to Sub-a4.

Table 1: Synthesis of Sub-a2 and Sub-a4

Synthesis of Sub-b1:

Under nitrogen atmosphere, Sub-a1 (17.66 g, 55 mmol), 7-bromo-1-iodo-2-hydroxynaphthalene (17.45 g, 50 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ , 0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (180 mL), anhydrous ethanol (45 mL) and deionized water (45 mL) were added to a 500 mL three-necked flask in sequence, stirring and heating were started, and the temperature was raised to reflux for reaction for 16 h. After the system was cooled to room temperature, it was extracted with dichloromethane (150 mL×3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid (11.03 g, yield 53%).

Referring to the synthesis of Sub-b1, reactant Sub-aX shown in Table 2 was used instead of Sub-a1, and reactant B was used instead of 7-bromo-1-iodo-2-hydroxynaphthalene to synthesize Sub-b2 to Sub-b10.

Table 2: Synthesis of Sub-b2 to Sub-b10

Synthesis of Sub-c1:

Under nitrogen atmosphere, add Sub-b1 (20.81 g, 50 mmol), tert-butyl peroxybenzoate, (BzOOt-Bu, 19.42g, 100mmol), palladium acetate (1.12g, 5mmol), 3-nitropyridine (0.62g, 5mmol), hexafluorobenzene (C ₆ F ₆ , 210mL) and N,N'-dimethylimidazolidinone (DMI, 140mL), start stirring and heating, raise the temperature to 90°C and react for 4h. After the system is cooled to room temperature, extract with ethyl acetate (100mL×3 times), dry the organic phase with anhydrous magnesium sulfate, filter, and distill the filtrate to remove the solvent under reduced pressure to obtain a crude product. Use n-heptane/dichloromethane as the mobile phase to purify the crude product by silica gel column chromatography to obtain a white solid (10.77g, yield 52%).

Sub-c2 to Sub-c10 were synthesized by referring to Sub-c1 and using Sub-bX shown in Table 3 instead of Sub-b1.

Table 3: Synthesis of Sub-c2 to Sub-c10

Synthesis of Sub-c11:

Under nitrogen atmosphere, add Sub-c1 (10.36 g, 25 mmol) and 200 mL of benzene-D6 to a 100 mL three-necked flask, heat to 60 ° C, add trifluoromethanesulfonic acid (22.51 g, 150 mmol), continue to heat to boiling and stir for 24 hours. After the reaction system is cooled to room temperature, add 50 mL of heavy water, stir for 10 minutes, and then add saturated K ₃ PO ₄ aqueous solution to neutralize the reaction solution. Extract the organic layer with dichloromethane (50 mL × 3 times), combine the organic phases and dry over anhydrous sodium sulfate, filter, and distill the filtrate to remove the solvent under reduced pressure to obtain a crude product. Use n-heptane/dichloromethane as the mobile phase to purify the crude product by silica gel column chromatography to obtain a white solid Sub-c11 (6.82 g, yield 64%).

Synthesis of Sub-c12:

Under nitrogen atmosphere, add Sub-b10 (10.80 g, 25 mmol), palladium dichloride (0.22 g, 1.25 mmol) and DMSO (120 mL) to a 250 mL three-necked flask, heat to 140 ° C and stir for 12 hours. After the reaction system is cooled to room temperature, extract the organic layer with dichloromethane (50 mL × 3 times), combine the organic phases and dry over anhydrous sodium sulfate, filter, and distill the filtrate under reduced pressure to remove the solvent to obtain a crude product. Use n-heptane/dichloromethane as the mobile phase to purify the crude product by silica gel column chromatography to obtain a white solid Sub-c12 (7.85 g, yield 73%).

Synthesis of Sub-d1:

Under nitrogen atmosphere, Sub-c1 (13.36 g, 50 mmol), 4-chlorophenylboronic acid (8.60 g, 55 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ , 0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (140 mL), anhydrous ethanol (35 mL) and deionized water (35 mL) were added to a 500 mL three-necked flask in sequence, stirring and heating were started, and the temperature was raised to reflux for reaction for 16 h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL×3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid sub-d1 (13.82 g, yield 62%).

Referring to the synthesis of Sub-d1, Sub-cX shown in Table 4 was used instead of Sub-c1, and reactant C was used instead of 4-chlorophenylboronic acid to synthesize Sub-d2 to Sub-d8.

Table 4: Synthesis of Sub-d2 to Sub-d8

Preparation of Compound A2

The intermediate Sub-c1 (35.0 g, 84.8 mmol) was added to a round-bottom flask, and 350 mL of THF was added to the flask after dehydration. The system was cooled to -80°C to -90°C with liquid nitrogen, and n-butyl lithium (6.5 g, 101.4 mmol) was added dropwise. After the addition, the temperature was kept at -80°C to -90°C. After the addition, the temperature was kept at 1 h, and then the temperature was naturally raised to room temperature. After the reaction was completed, 100 mL of HCl aqueous solution (concentration of 2 mol/L) was added and stirred for 0.5 h. Dichloromethane and water were added for liquid separation and extraction. The organic phase was washed to a neutral pH of 7, the organic phases were combined, dried over anhydrous MgSO ₄ for 10 min, filtered, the filtrate was spin-dried, and the white solid intermediate Sub-e1 (16.0 g, yield 50%) was obtained by slurrying with n-heptane twice.

Sub-e1 (16.0 g, 42.2 mmol), 2-(4-biphenyl)-4-chloro-6-phenyl-1,3,5-triazine (14.5 g, 42.2 mmol), tetrakistriphenylphosphine palladium (0.5 g, 0.4 mmol), potassium carbonate (11.6 g, 84.4 mmol), tetrabutylammonium bromide (0.1 g, 0.4 mmol), toluene (128 mL), ethanol (64 mL) and deionized water (32 mL) were added to a three-necked flask, heated to 76 ° C under nitrogen protection, heated to reflux and stirred for 8 h. After the reaction was completed, the solution was cooled to room temperature, toluene and water were added to extract the reaction solution, the organic phases were combined, the organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated; the crude product was purified by silica gel column chromatography to obtain solid compound A2 (16.8 g, yield 62%, m/z = 643.2 [M + H] ⁺ ).

Sub-eX was synthesized by referring to Sub-c1 and using the reactant Sub-cX shown in Table 5 instead of Sub-c1.

Table 5: Synthesis of Sub-e2 to Sub-e10

Compound AX shown in the following Table 6 was synthesized in a similar manner to A2, except that starting material 1 was used instead of 2-(4-biphenyl)-4-chloro-6-phenyl-1,3,5-triazine, and Sub-eX was used instead of sub-e1.

Table 6: Synthesis of Compound AX

Mass spectrometry analysis was performed on some of the compounds synthesized above, and the analysis results shown in Table 7 were obtained:

Table 7: Mass spectral data of compound AX

Synthesis of the second compound:

Synthesis of intermediate sub-I-A1

1) Preparation of intermediate sub1-I-A1

2-Bromocarbazole (30.0 g, 121.8 mmol), iodobenzene (24.8 g, 78.03 mmol), CuI (4.64 g, 24.3 mmol), K ₂ CO ₃ (37.0 g, 268.1 mmol), 18-crown ether-6 (3.2 g, 12.1 mmol) were added to a three-necked flask, and dried DMF (300 mL) solvent was added. Under nitrogen protection, the temperature was raised to 150°C, and the temperature was maintained and stirred for 17 hours; cooled to room temperature, and stirring was stopped. The reaction solution was washed with water, and the organic phase was separated, dried over 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 a white solid product intermediate sub1-I-A1 (26.3 g, yield 67%).

2) Preparation of intermediate sub1-II-A1

The intermediate sub1-I-A1 (26.0 g, 80.6 mmol), o-chloroaniline (11.3 g, 88.7 mmol), Pd(dba) ₂ (0.73 g, 0.8 mmol),

2-Dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (x-phos, 0.76 g, 1.6 mmol), sodium tert-butoxide (11.6 g, 121.0 mmol) were added to a three-necked flask, and toluene (300 mL) solvent was added. Under nitrogen protection, the temperature was raised to 110°C and stirred for 15 hours. After cooling to room temperature, stirring was stopped, the reaction solution was washed with water to separate the organic phase, dried over 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 the intermediate sub1-II-A1 (15.7 g, yield 53%) as a white solid.

3) Preparation of intermediate sub-A1

The intermediate sub1-II-A1 (15.0 g, 46.5 mmol), cesium carbonate (37.9 g, 116.3 mmol), tricyclohexylphosphinofluoroborate (8.5 g, 23.2 mmol), Pd(dba) ₂ (0.52 g, 2.3 mmol) were added to a three-necked flask, and toluene (150 mL) solvent was added. Under nitrogen protection, the temperature was raised to 110°C and stirred for 10 hours. After cooling to room temperature, stirring was stopped, the reaction solution was washed with water and the organic phase was separated, dried over 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 a white solid product intermediate sub-A1 (9.43 g, yield 61%).

Substitute 2-bromocarbazole with raw material 2, substitute iodobenzene with raw material 3, and substitute o-chloroaniline with raw material 4 in the following table, and use a similar method to Sub-A1 to synthesize the intermediates Sub-A2 to Sub-A10 shown in the following Table 8:

Table 8: Synthesis of intermediates Sub-A2 to Sub-A10

Synthesis of compound B1

The intermediate sub-A1 (9.0 g, 27.0 mmol), 1-bromo-4-(2-phenyl)benzene (8.3 g, 27.0 mmol), tris(dibenzylideneacetone)dipalladium (0.2 g, 0.3 mmol), 2-dicyclohexylphosphine-2′,6′-dimethoxy-biphenyl (0.2 g, 0.5 mmol), sodium tert-butoxide (5.2 g, 154.1 mmol) were added to a three-necked flask, and toluene (300 mL) solvent was added. Under nitrogen protection, the temperature was raised to 110° C. and the temperature was maintained and stirred for 15 hours; The mixture was cooled to room temperature and stirring was stopped. The reaction solution was washed with water and the organic phase was separated and dried over anhydrous magnesium sulfate. 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 a white solid product B1 (9.9 g, yield 64%). Mass spectrum: m/z = 561.2 [M+H] ⁺ .

In the following table, intermediates sub-A2 to sub-A10 are substituted for intermediate sub-A1, and raw material 5 is substituted for 1-bromo-4-(2-phenyl)benzene. A similar method is used to synthesize the compounds shown in the following Table 9:

Table 9: Synthesis of Compound BX

Mass spectrometry analysis was performed on some of the compounds synthesized above, and the analysis results shown in Table 10 were obtained:

Table 10: Mass spectrum of compound BX

C22 Synthesis of Compounds:

Under nitrogen atmosphere, 10-chloro-2-phenylphenanthro[3,4-D]oxazole (10.0 g, 30.3 mmol), N-phenyl-4-benzidine (CAS: 32228-99-2, 7.5 g, 30.9 mmol), tris(dibenzylideneacetone)dipalladium (0.27 g, 0.3 mmol), (2-dicyclohexylphosphine-2', 4', 6'triisopropylbiphenyl) (X-phos, 0.28 g, 0.6 mmol), sodium tert-butoxide (4.4 g, 45.4 mmol) and toluene (100 mL) were added to a 250 mL three-necked flask in sequence, and the temperature was raised to reflux, and the reaction was stirred overnight. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by reduced pressure distillation to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain white solid compound C22 (12.7 g, yield 78%, m/z = 539.2 [M+H] ⁺ ).

Referring to the synthesis of compound 3, the starting material 6 shown in Table 11 was used instead of N-phenyl-4-benzidine to synthesize the compounds in Table 11.

Table 11: Synthesis of Compound CX

Synthesis of compound C12

10-Chloro-2-phenylphenanthro[3,4-D]oxazole (35.0 g, 106.1 mmol), biboronic acid pinacol ester (32.3 g, 127.3 mmol), Pd(dppf)Cl ₂ (0.7 g, 1.1 mmol), KOAc (20.8 g, 212.2 mmol), 1,4-dioxane (350 mL) were added and refluxed at 100°C for 12 h. When the reaction was completed, CH ₂ Cl ₂ and water were used for extraction. The organic layer was dried and concentrated with anhydrous MgSO ₄ , and the resulting compound was subjected to silica gel column and recrystallization to obtain compound sub-B1 (28.6 g, yield 64%).

Sub-B1 (25.0 g, 59.3 mmol), N-(4-bromophenyl-)-N-phenyl-benzidine (23.7 g, 59.3 mmol), tetrakistriphenylphosphine palladium (0.7 g, 0.6 mmol), potassium carbonate (16.4 g, 118.6 mmol), tetrabutylammonium bromide (0.2 g, 0.6 mmol) were added to a three-necked flask, and toluene (200 mL), ethanol (100 mL) and deionized water (50 mL) were added to the three-necked flask, and the temperature was raised to 76°C under nitrogen protection, and heated to reflux and stirred for 18 h. Cool to room temperature, stop stirring, wash the reaction solution with water, separate the organic phase, dry with anhydrous magnesium sulfate, and remove the solvent under reduced pressure to obtain a crude product; use dichloromethane/n-heptane as the mobile phase to purify the crude product by silica gel column chromatography to obtain a white product C12 (24.7 g, yield 68%, m/z = 615.2 [M+H] ⁺ ).

Referring to the synthesis of compound C12, the raw material 7 shown in Table 12 was used instead of N-(4-bromophenyl-)-N-phenyl-benzidine to obtain The compounds in Table 12 were obtained.

Table 12: Synthesis of Compound CX

Mass spectrometry analysis was performed on some of the compounds synthesized above, and the analysis results shown in Table 13 were obtained:

Table 13: Mass spectrum of compound CX

Preparation and evaluation of organic electroluminescent devices:

Example 1: Preparation of red organic electroluminescent device

First, the anode pretreatment is carried out through the following process: the thickness is On the ITO/Ag/ITO substrate, the surface is treated by using ultraviolet ozone and O ₂ :N ₂ plasma to increase the work function of the anode, and the surface of the ITO substrate is cleaned by using an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

On the experimental substrate (anode), PD:HT-1 was co-evaporated at an evaporation rate ratio of 2%:98% to form a film with a thickness of Then, HT-1 was vacuum-deposited on the hole injection layer to form a hole injection layer with a thickness of hole transport layer.

Compound HT-2 is vacuum-deposited on the hole transport layer to form a layer with a thickness of Holes adjustment layer.

Next, on the hole adjustment layer, compound A2 was used as the first host, compound C22 was used as the second host, and RD-1 was used as the dopant to prepare a red light emitting layer by co-evaporation. Compound A2: compound C22: RD-1 were co-evaporated at an evaporation rate ratio of 49%: 49%: 2% to form a layer with a thickness of The red light emitting layer (EML)

On the light-emitting layer, compound ET-1 and LiQ were mixed in a weight ratio of 1:1 and evaporated to form A thick electron transport layer (ETL) is formed by evaporating Yb on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a deposition rate of 1:9 and vacuum-deposited on the electron injection layer to form a layer with a thickness of cathode.

In addition, the thickness of the vacuum evaporation layer on the cathode is CP-1 is formed to form a covering layer, thereby completing the manufacture of a red organic electroluminescent device.

Embodiments 2 to 36

An organic electroluminescent device was prepared by the same method as in Example 1, except that the combination of compounds A2 and C22 in Example 1 was replaced by the combination of light-emitting layer hosts shown in Table 14 below when preparing the light-emitting layer.

Comparative Examples 1 to 3

An organic electroluminescent device was prepared by the same method as in Example 1, except that the light-emitting layer host combinations shown in Table 14 were used to replace the combination of compounds A2 and C22 in Example 1.

Among them, when preparing each embodiment and comparative example, the compound structure used is as follows:

The red organic electroluminescent devices prepared in Examples 1 to 36 and Comparative Examples 1 to 3 were subjected to performance tests. Specifically, the IVL performance of the devices was tested under the condition of 10 mA/cm ² , and the T95 device life was tested under the condition of 20 mA/cm ^2. The test results are shown in Table 14.

Table 14

Referring to Table 14 above, it can be seen that the organic electroluminescent device of the present invention uses two specific compounds as the main materials of the light-emitting layer. Compared with the device of the comparative example, the luminous efficiency is increased by at least 10.82% and the life is increased by at least 12.9%.

Example 37: Preparation of red organic electroluminescent device

On the experimental substrate (anode), PD:HT-5 was co-evaporated at an evaporation rate ratio of 3%:97% to form a film with a thickness of Then, HT-5 was vacuum-deposited on the HIL to form a HIL with a thickness of hole transport layer.

Compound HT-1 is vacuum-deposited on the hole transport layer to form a layer with a thickness of Holes adjustment layer.

Next, on the hole adjustment layer, compound A2 was used as the first host, compound B9 was used as the second host, and RD-1 was used as the dopant, and a red light emitting layer was prepared by a co-evaporation method. The first host and the second host were mixed in a weight ratio of 50:50 to obtain a composition; the composition of the host material and RD-1 were simultaneously evaporated at an evaporation rate ratio of 97%:3% to form a layer with a thickness of The red light emitting layer (EML)

On the light-emitting layer, compound ET-3 and LiQ were mixed in a weight ratio of 1:1 and evaporated to form A thick electron transport layer (ETL) is formed by evaporating Yb on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:8 and vacuum evaporated on the electron injection layer to form a layer with a thickness of cathode.

In addition, the thickness of the vacuum evaporation layer on the cathode is CP-1, thereby completing the manufacture of the red organic electroluminescent device.

Embodiments 38 to 45

An organic electroluminescent device was prepared by the same method as in Example 37, except that the combination of compounds A2 and B9 in Example 37 was replaced by the combination of light-emitting layer hosts shown in Table 15 below when preparing the light-emitting layer.

Comparative Examples 4 to 5

An organic electroluminescent device was prepared by the same method as in Example 37, except that the light-emitting layer host combinations shown in Table 15 were used instead of the combination of compounds A2 and B9 in Example 37 when preparing the light-emitting layer.

The red organic electroluminescent devices prepared in Examples 37 to 45 and Comparative Examples 4 to 5 were subjected to performance tests. Specifically, the IVL performance of the devices was tested under the condition of 10 mA/cm ² , and the T95 device life was tested under the condition of 20 mA/cm ^2. The test results are shown in Table 15.

Table 15

Referring to Table 15 above, it can be seen that the organic electroluminescent device of the present invention uses two specific compounds as the main materials of the light-emitting layer. Compared with the device of the comparative example, the luminous efficiency is increased by at least 16.5%, and the T95 life is increased by at least 13.1%.

The preferred embodiments of the present invention are described in detail above in conjunction with the accompanying drawings. However, the present invention is not limited to the specific details in the above embodiments. Within the technical concept of the present invention, a variety of simple modifications can be made to the technical solution of the present invention, and these simple modifications all belong to the protection scope of the present invention.

Claims

An organic electroluminescent device comprises a cathode, an anode and an organic layer;

Wherein, the cathode and the anode are arranged opposite to each other;

The organic layer is located between the cathode and the anode;

The organic layer includes an organic light-emitting layer;

The organic light-emitting layer comprises a first compound and a second compound;

The first compound has a structure shown in Formula 1:

wherein, Z 1 , Z 2 and Z 3 are each independently selected from N or C(H), and at least one of Z 1 to Z 3 is N;

Y is selected from S or O;

One of X1 and X2 is -N=, and the other is O or S;

Ring A is selected from a naphthalene ring or a phenanthrene ring;

L 1 , L 2 and L 3 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

Ar 1 , Ar 2 and Ar 3 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

The substituents in L 1 , L 2 , L 3 , Ar 1 , Ar 2 and Ar 3 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, aryloxy group having 6 to 20 carbon atoms or arylthio group having 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;

Each R 1 is the same or different and is independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms; n 1 represents the number of R 1 ; n 1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;

The second compound has a structure shown in Formula 2 or Formula 3:

One of X3 and X4 is -N=, and the other is O or S;

L 4 , L 5 and L 6 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

Ar 4 , Ar 5 and Ar 6 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

The substituents in L 4 , L 5 , L 6 , Ar 4 , Ar 5 and Ar 6 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, aryloxy group having 6 to 20 carbon atoms or arylthio group having 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;

Each R2 is the same or different and is independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms; n2 represents the number of R2 ; n2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

Ring C and Ring E are each independently selected from an aromatic ring having 6 to 14 carbon atoms;

L7 and L8 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

Ar 7 and Ar 8 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

The substituents in L 7 , L 8 , Ar 7 and Ar 8 are the same or different and are independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 20 carbon atoms or arylthio having 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;

Each R 3 , R 4 and R 5 is the same or different and is independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent R 4 groups form a ring; n 3 represents the number of R 3 , n 4 represents the number of R 4 , and n 5 represents the number of R 5 ; n 3 and n 5 are independently selected from 0, 1, 2, 3, 4, 5 or 6; n 4 is selected from 0, 1 or 2.
The organic electroluminescent device according to claim 1, wherein the first compound is selected from the structures shown in the following formulas (1-1) to (1-15):

Wherein, Y is O or S.
The organic electroluminescent device according to claim 1 or 2, wherein in the first compound, Ar 1 , Ar 2 and Ar 3 are the same or different and are independently selected from a substituted or unsubstituted group W 1 ; the unsubstituted group W 1 is selected from the group consisting of:

The substituted group W1 has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzoxazolyl or benzothiazolyl, and when the number of substituents on the group W1 is greater than 1 , each substituent is the same or different.
The organic electroluminescent device according to any one of claims 1 to 3, wherein in the first compound, L 1 , L 2 and L 3 are the same or different, and are independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted dibenzothienylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted benzoxazolylene group, and a substituted or unsubstituted benzothiazolylene group;

Optionally, the substituents in L 1 , L 2 and L 3 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.
The organic electroluminescent device according to any one of claims 1 to 4, wherein the second compound is selected from the structure represented by formula (2-1), formula (2-2) or formula (3-1) to formula (3-20):
The organic electroluminescent device according to any one of claims 1 to 5, wherein in formula 2, Ar 4 , Ar 5 and Ar 6 are the same or different and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted peryl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl;

Optionally, the substituents in Ar 4 , Ar 5 and Ar 6 are the same or different and are each independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl or carbazolyl. Optionally, in Ar 4 and Ar 5 , any two adjacent substituents form a benzene ring.
The organic electroluminescent device according to any one of claims 1 to 6, wherein in formula 2, L 4 , L 5 and L 6 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolylene group.

Optionally, the substituents in L 4 , L 5 and L 6 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.
The organic electroluminescent device according to any one of claims 1 to 7, wherein in formula 1, each R 1 is the same or different and is independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl;

Optionally, in Formula 2, each R 2 is the same or different and is independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl or carbazolyl;

Optionally, in Formula 3, each R 3 , R 4 and R 5 are the same or different and are independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.
The organic electroluminescent device according to any one of claims 1 to 8, wherein, in Formula 3, L7 and L8 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolylene group;

Optionally, the substituents in L7 and L8 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.
The organic electroluminescent device according to any one of claims 1 to 9, wherein in formula 3, Ar 7 and Ar 8 are the same or different and are each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted peryl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzothiazolyl group, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted pyridyl;

Optionally, the substituents in Ar 7 and Ar 8 are each independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl or carbazolyl, and optionally, in Ar 7 and Ar 8 , any two adjacent substituents form a benzene ring.
The organic electroluminescent device according to any one of claims 1 to 10, wherein in the first compound represented by formula 1, The same or different, and each independently selected from the following groups:

Optionally, in Formula 2, Each is independently selected from the following groups:

Optionally, in Formula 3, Each is independently selected from the following groups:
The organic electroluminescent device according to any one of claims 1 to 11, wherein the organic light-emitting layer comprises a host material and a dopant, the host material comprises a first compound and a second compound; and the mass ratio of the first compound to the second compound is 30:70 to 70:30.
The organic electroluminescent device according to any one of claims 1 to 12, wherein the first compound is selected from the group consisting of the following compounds:

Preferably, the second compound is selected from the group consisting of the following compounds:

The second compound shown in Formula 3 is selected from the following structures:
An electronic device, characterized in that it comprises the organic electroluminescent device according to any one of claims 1 to 13.