CN117412652A

CN117412652A - Organic electroluminescent device and electronic device

Info

Publication number: CN117412652A
Application number: CN202211226718.3A
Authority: CN
Inventors: 徐先彬; 张孔燕; 张鹤鸣
Original assignee: Shaanxi Lighte Optoelectronics Material Co Ltd
Current assignee: Shaanxi Lighte Optoelectronics Material Co Ltd
Priority date: 2022-10-09
Filing date: 2022-10-09
Publication date: 2024-01-16
Also published as: WO2024078137A1

Abstract

The application provides an organic electroluminescent device and an electronic device, wherein the organic electroluminescent device comprises a cathode, an anode and an organic layer. The organic layer includes an organic light emitting layer including a first compound and a second compound; the first compound is selected from compounds shown in a formula 1; the second compound is selected from compounds shown in formula 2 or formula 3.

Description

Organic electroluminescent device and electronic device

Technical Field

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

Background

In recent years, organic electroluminescent devices (OLEDs) are very popular flat display products at home and abroad because OLED displays have characteristics of self-luminescence, wide viewing angle, short reaction time, high efficiency, wide color gamut, etc.

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 assist layer, an electron blocking layer, a light emitting layer (containing a host and dopant materials), a hole blocking layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied to the organic electroluminescent device, holes and electrons are injected into the light emitting layer from the anode and the cathode, respectively. Then, in the light emitting layer, the injected holes recombine with electrons to form excitons. The excitons are in an excited state to release energy outwards, so that the light-emitting layer emits light outwards.

At present, the organic electroluminescent device still has the problem of poor performance in the use process, such as the problems of too high driving voltage, too low luminous efficiency or short service life, which affect the use field of the organic electroluminescent device, so that further research on the field is still necessary to improve the performance of the organic electroluminescent device.

Disclosure of Invention

In view of the foregoing problems of the prior art, an object of the present application is to provide an organic electroluminescent device and an electronic apparatus for improving performance of the device and the apparatus.

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 represented by formula 1:

wherein, Z is ₁ 、Z ₂ And Z ₃ Each independently selected from N or C (H), and Z ₁ ～Z ₃ At least one of which is N;

y is selected from S or O;

X ₁ and X ₂ One of them is-n=, the other is O or S;

ring a is selected from naphthalene or phenanthrene rings;

L ₁ 、L ₂ And L ₃ 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 is a group ₃ 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;

L ₁ 、L ₂ 、L ₃ 、Ar ₁ 、Ar ₂ and Ar is a group ₃ The substituents in (a) are the same or different and are each 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 is ₁ The two groups are identical or different and are each independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, halogenated alkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms or cycloalkyl groups with 3 to 10 carbon atoms; n is n ₁ R represents ₁ Is the number of (3); n is n ₁ Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;

the second compound has a structure represented by formula 2 or formula 3:

X ₃ and X ₄ One of them is- (I)N=, the other is O or S;

L ₄ 、L ₅ and L ₆ 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 is a group ₆ 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;

L ₄ 、L ₅ 、L ₆ 、Ar ₄ 、Ar ₅ and Ar is a group ₆ The substituents in (a) are the same or different and are each 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 is ₂ The two groups are identical or different and are each independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, halogenated alkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms or cycloalkyl groups with 3 to 10 carbon atoms; n is n ₂ R represents ₂ Is the number of (3); n is n ₂ Selected from 0, 1, 2, 3, 4, 5, 6 or 7;

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

L ₇ and L ₈ 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 is a group ₈ 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;

L ₇ 、L ₈ 、Ar ₇ and Ar is a group ₈ The substituents in (a) are the same or different and are each 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 is ₃ 、R ₄ And R is ₅ The two groups are identical or different and are respectively and independently selected from deuterium, cyano, halogen groups, alkyl with 1-10 carbon atoms, halogenated alkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, trialkyl silicon group with 3-12 carbon atoms, triphenyl silicon group, aryl with 6-20 carbon atoms, heteroaryl with 3-20 carbon atoms or cycloalkyl with 3-10 carbon atoms; optionally, any two adjacent R ₄ Forming a ring; n is n ₃ R represents ₃ Number n of (n) ₄ R represents ₄ Number n of (n) ₅ R represents ₅ Is the number of (3); n is n ₃ And n ₅ Each independently selected from 0, 1, 2, 3, 4, 5, or 6; n is n ₄ Selected from 0, 1 or 2.

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

The luminescent layer host material of the organic electroluminescent device comprises a first compound and a second compound, wherein the first compound has a structure of connecting electron transport groups with a benzodibenzofuran/thiophene and oxazole/thiazole fused mother nucleus, the second compound is selected from indole carbazole compounds or phenanthroazole/thiazole mother nucleus and has hole transport properties, and the first compound and the second compound are mixed into a red light host material. Firstly, the hole transport material and the electron transport material used in the application have larger conjugate areas, on one hand, the first excited triplet state energy level of the compound can be reduced, on the other hand, the molecular action between the hole transport material and the electron transport material can be enhanced, an exciplex can be formed more effectively, the carrier mobility can be improved, the energy transfer efficiency of the main material to the luminescent material can be improved, and finally the luminescent efficiency of the device can be improved. Secondly, in the first compound used in the application, the parent nucleus in the parent nucleus is connected with the electron transport group, so that the LUMO (lowest unoccupied orbital) electron cloud distribution of the compound can be limited to benzodibenzofuran/thiophene and oxazole/thiazole parts, and the attack of excitons on C-N bonds in aromatic amines is inhibited, so that the service life of the device is prolonged.

Drawings

The accompanying drawings are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate the application and, together with the description, do not limit the application.

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

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

Reference numerals

100. Anode 200, cathode 300, functional layer 310, and 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 and electronic device

Detailed Description

Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments may be embodied in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the exemplary embodiments 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, numerous specific details are provided to give a thorough understanding of 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 denote the same or similar structures, and thus detailed descriptions thereof 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 represented by formula 1:

y is selected from S or O;

X ₁ and X ₂ One of them is-n=, the other is O or S;

ring a is selected from naphthalene or phenanthrene rings;

The second compound has a structure represented by formula 2 or formula 3:

X ₃ and X ₄ One of them is-n=, the other is O or S;

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

In this application, the descriptions "each … … is independently" and "… … is independently" and "… … is independently" are interchangeable, and should be understood in a broad sense, which may mean that specific options expressed between the same symbols in different groups do not affect each other, or that specific options expressed between the same symbols in the same groups do not affect each other. For example, the number of the cells to be processed,wherein each q is independently 0, 1, 2 or 3, and each R "is independently selected from hydrogen, deuterium, fluorine, chlorine", with the meaning: the formula Q-1 represents Q substituent groups R ' on the benzene ring, wherein R ' can be the same or different, and the options of each R ' are not mutually influenced; the formula Q-2 represents that each benzene ring of the biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced each other.

In the present application, such terms as "substituted or unsubstituted" mean that the functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to aryl having a substituent Rc or unsubstituted aryl. Wherein Rc, the substituent mentioned above, may be, for example, deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuteroaryl 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, arylthio having 6 to 20 carbon atoms or the like. The number of substitutions may be 1 or more.

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

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

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

Aryl in this application refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups connected by a carbon-carbon bond conjugate. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered aryl groups herein unless otherwise indicated. Among them, the condensed ring aryl group may include, for example, a bicyclic condensed aryl group (e.g., naphthyl group), a tricyclic condensed aryl group (e.g., phenanthryl group, fluorenyl group, anthracenyl group), and the like. The aryl group does not contain hetero atoms such as B, N, O, S, P, se, si and the like. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, triphenylene, perylenyl, benzo [9,10 ] ]Phenanthryl, pyrenyl, benzofluoranthenyl,A base, etc.

In the present application, reference to arylene means a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from the aryl group.

In the present application, terphenyl includes

In the present application, the substituted or unsubstituted aryl (arylene) group may have 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 carbon atoms. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 25 carbon atoms, in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 18 carbon atoms, and in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 15 carbon atoms.

In this application, the fluorenyl group may be substituted with 1 or more substituents, and in the case where the above fluorenyl group is substituted, the substituted fluorenyl group may be:and the like, but is not limited thereto.

In the present application, aryl groups as substituents are exemplified by, but not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl, and the like.

In the present application heteroaryl means a monovalent aromatic ring or derivative thereof containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, which may be one or more of B, O, N, P, si, se and S. Heteroaryl groups may be monocyclic heteroaryl or polycyclic heteroaryl, in other words, heteroaryl groups may be a single aromatic ring system or multiple aromatic ring systems that are conjugated through carbon-carbon bonds, with either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, thiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without limitation thereto.

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

In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) group may 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 having a total of from 3 to 30 carbon atoms, in other embodiments the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total of from 12 to 18 carbon atoms, and in other embodiments the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total of from 5 to 12 carbon atoms.

Heteroaryl groups as substituents in the present application are, for example, but not limited to, pyridyl, carbazolyl, dibenzothienyl, dibenzofuranyl, benzoxazolyl, benzothiazolyl, benzimidazolyl.

In the present application, a substituted heteroaryl group may be one in which one or more hydrogen atoms in the heteroaryl group are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, and 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 of the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 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, iodine.

Specific examples of trialkylsilyl groups herein include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

Specific examples of haloalkyl groups herein include, but are not limited to, trifluoromethyl.

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

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

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

In this application, a ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6 membered ring. The 3-15 membered ring means a cyclic group having 3-15 ring atoms. Examples of the 3-to 15-membered ring include cyclopentane, cyclohexane, fluorene ring, and benzene ring.

In the present application,refers to chemical bonds that interconnect other groups.

In the present application, the connection key is not positioned in relation to a single bond extending from the ring systemIt means that one end of the bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the remainder of the compound molecule. For example, as shown in formula (f), the naphthyl group represented by formula (f) is linked to the other positions of the molecule via two non-positional linkages extending through the bicyclic ring, which means includes any of the possible linkages shown in formulas (f-1) to (f-10):

as another example, as shown in the following formula (X '), the dibenzofuranyl group represented by the formula (X ') is linked to the other position of the molecule through an unoositioned linkage extending from the middle of one benzene ring, and the meaning represented by the formula (X ' -1) to (X ' -4) includes any possible linkage as shown in the formula (X ' -1):

an delocalized substituent in this application refers to a substituent attached by a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system. For example, as shown in formula (Y) below, the substituent R' represented by formula (Y) is attached to the quinoline ring via an unoositioned bond, which means that it includes any of the possible linkages shown in formulas (Y-1) to (Y-7):

In some embodiments, in the first compound, Z ₁ 、Z ₂ And Z ₃ Each independently selected from N or C (H), and Z ₁ ～Z ₃ At least one of which is N.

More specifically, in some embodiments of the present application, whatIn the first compound, X ₁ 、X ₂ Are all C (H), X ₃ Is N; or X ₁ 、X ₃ Are all C (H), X ₂ Is N, X ₂ 、X ₃ Are all C (H), X ₁ Is N; or alternatively; x is X ₁ 、X ₂ Are all N, X ₃ C (H); or X ₁ 、X ₃ Are all N, X ₂ C (H); alternatively, X ₂ 、X ₃ Are all N, X ₁ C (H); alternatively, X ₁ 、X ₂ 、X ₃ Are all N.

In some embodiments, Z ₁ 、Z ₂ And Z ₃ Each independently selected from N or C (H), and Z ₁ ～Z ₃ At least two of which are N; or Z is ₁ 、Z ₂ And Z ₃ Are all N.

In some embodiments, the first compound is selected from the structures shown in 1-1 to 1-15 below:

wherein Y is O or S.

In some embodiments, in the first compound, ar ₁ 、Ar ₂ And Ar is a group ₃ Each independently selected from substituted or unsubstituted aryl groups 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 groups 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.

Alternatively, ar ₁ 、Ar ₂ And Ar is a group ₃ The substituents in (a) are each independently selected from deuterium, halogen group, cyano group, haloalkyl group having 1 to 4 carbon atoms, and carbon atomDeuterated alkyl with 1-4 sub-numbers, alkyl with 1-4 carbon atoms, cycloalkyl with 5-10 carbon atoms, aryl with 6-15 carbon atoms, heteroaryl with 5-12 carbon atoms, trialkyl silicon group with 3-8 carbon atoms or deuterated aryl with 6-15 carbon atoms, and optionally any two adjacent substituents form benzene ring or fluorene ring.

In some embodiments, in the first compound, ar ₁ 、Ar ₂ And Ar is a group ₃ Each independently selected from the group consisting of substituted or unsubstituted groups W ₁ The method comprises the steps of carrying out a first treatment on the surface of the The unsubstituted group W ₁ Selected from the group consisting of:

substituted group W ₁ Each independently selected from deuterium, fluoro, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, t-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzoxazolyl or benzothiazolyl, and when the group W ₁ When the number of the substituents is more than 1, the substituents are the same or different.

In some embodiments, in the first compound, ar ₁ 、Ar ₂ And Ar is a group ₃ Each independently selected from the group consisting of 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 triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, and substituted or unsubstituted pyridyl.

Alternatively, ar ₁ 、Ar ₂ And Ar is a group ₃ Each substituent of (a) is independently selected from deuterium, fluoro, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, t-butyl, phenyl, naphthyl, pyridinyl, dibenzofuranyl, dibenzothienyl or carbazolyl, optionally Ar ₁ And Ar is a group ₂ Any two adjacent substituents form a benzene ring.

In some embodiments, in the first compound,each independently selected from the following groups:

in some embodiments, in the first compound, ar ₁ And Ar is a group ₂ Each independently selected from the group consisting of:

in some embodiments, in the first compound, ar ₃ Selected from the group consisting of:

in some embodiments, in the first compound, L ₁ 、L ₂ And L ₃ Identical or different and are each independently selected from single bonds, substituted or unsubstituted arylene groups having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, and carbon atomsSubstituted or unsubstituted heteroarylene of 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18.

Alternatively, L ₁ 、L ₂ And L ₃ The substituents in (a) are each 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, deuteroalkyl having 1 to 4 carbon atoms, phenyl or naphthyl.

In some embodiments, in the first compound, L ₁ 、L ₂ And L ₃ 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 phenanthrylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted benzoxazolylene group, and a substituted or unsubstituted benzothiazolylene group.

Alternatively, L ₁ 、L ₂ And L ₃ The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, tridentate methyl, trimethylsilyl or phenyl.

In some embodiments, in the first compound, L ₃ Selected from the group consisting of single bonds or:

in some embodiments, in the first compound, L ₁ And L ₂ Each independently selected from the group consisting of a single bond or:

in some embodiments, in the first compound, each R ₁ The same or different and are each independently selected from deuterium, cyano, fluoro, tridentate 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 structures represented by formulas (2-1), (2-2), or (3-1) - (3-20).

In some embodiments, the compound of formula 2 has a structure represented by formula 2-1 or 2-2:

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in some embodiments, in formula 2, ar ₄ 、Ar ₅ And Ar is a group ₆ Each independently selected from substituted or unsubstituted aryl groups 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 groups 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.

Alternatively, ar ₄ 、Ar ₅ And Ar is a group ₆ Each substituent of (a) is 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 2, ar ₄ 、Ar ₅ And Ar is a group ₆ Each independently selected from the group consisting of substituted or unsubstituted groups W ₂ The method comprises the steps of carrying out a first treatment on the surface of the The unsubstituted group W ₂ Selected from the group consisting of:

substituted group W ₂ Each independently selected from deuterium, fluoro, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, t-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl or carbazolyl, and when the group W ₂ When the number of the substituents is more than 1, the substituents are the same or different.

In some embodiments, in formula 2, ar ₄ 、Ar ₅ And Ar is a group ₆ Each independently selected from the group consisting of 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 triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoxazolyl, and substituted or unsubstituted benzimidazolyl.

Alternatively, ar ₄ 、Ar ₅ And Ar is a group ₆ Each substituent of (a) is independently selected from deuterium, fluoro, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, t-butyl, phenyl, naphthyl, pyridinyl, dibenzofuranyl, dibenzothienyl or carbazolyl, optionally Ar ₄ And Ar is a group ₅ Any two adjacent substituents form a benzene ring.

In some embodiments of the present invention, in some embodiments,each independently selected from the following groups: / >

In some embodiments, in formula 2, ar ₄ And Ar is a group ₅ Each independently selected from the group consisting of:

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in some embodiments, in formula 2, ar ₆ Selected from the group consisting of:

in some embodiments, in formula 2, L ₄ 、L ₅ And L ₆ And 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, a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

Alternatively, L ₄ 、L ₅ And L ₆ The substituents in (a) are each 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, deuteroalkyl having 1 to 4 carbon atoms, phenyl or naphthyl.

In some embodiments, in formula 2, L ₄ 、L ₅ And L ₆ 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 phenanthrylene group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted carbazole group.

Alternatively, L ₄ 、L ₅ And L ₆ The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, tridentate methyl, trimethylsilyl or phenyl.

In some embodiments, in formula 2, L ₄ Selected from the group consisting of single bonds or:

in some embodiments, in formula 2, L ₅ And L ₆ Each independently selected from the group consisting of a single bond or:

in some embodiments, in formula 2, each R ₂ The same or different and are each independently selected from deuterium, cyano, fluoro, tridentate 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 structures represented by the following formulas (3-1) to (3-20):

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in some embodiments, ring C and ring E of formula 3 are each independently selected from benzene rings or naphthalene rings.

In some embodiments, in formula 3, L ₇ And L ₈ 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, 15, 16, 17, or 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 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 carbon atoms.

Alternatively, L ₇ And L ₈ The substituents in (a) are each 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, deuteroalkyl having 1 to 4 carbon atoms, phenyl or naphthyl.

In some embodiments, in formula 3, L ₇ And L ₈ 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 phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted carbazole group.

Alternatively, L ₇ And L ₈ The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, tridentate methyl, trimethylsilyl or phenyl.

In some embodiments, in formula 3, L ₇ And L ₈ Each independently selected from the group consisting of a single bond or:

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in some embodiments, in formula 3, ar ₇ And Ar is a group ₈ Each independently selected from substituted or unsubstituted aryl groups 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 groups 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, ar ₇ And Ar is a group ₈ Each substituent of (a) is 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 is a group ₈ Each independently selected from the group consisting of substituted or unsubstituted groups W ₃ The method comprises the steps of carrying out a first treatment on the surface of the The unsubstituted group W ₃ Selected from the group consisting of:

substituted group W ₃ Each independently selected from deuterium, fluoro, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, t-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiopheneA radical or carbazolyl radical, and when a radical W ₃ When the number of the substituents is more than 1, the substituents are the same or different.

In some embodiments, in formula 3, ar ₇ And Ar is a group ₈ Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, and substituted or unsubstituted pyridyl.

Alternatively, ar ₇ And Ar is a group ₈ Each substituent of (a) is independently selected from deuterium, fluoro, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, t-butyl, phenyl, naphthyl, pyridinyl, dibenzofuranyl, dibenzothienyl or carbazolyl, optionally Ar ₇ And Ar is a group ₈ Any two adjacent substituents form a benzene ring.

In some embodiments, in formula 3, ar ₇ And Ar is a group ₈ Each independently selected from the group consisting of:

in some embodiments of the present invention, in some embodiments,each independently selected fromThe following groups:

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in some embodiments, each R ₁ The same or different and are each independently selected from deuterium, cyano, fluoro, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

In some embodiments, in formula 3, each R ₃ 、R ₄ And R is ₅ Identical or different and are each independently selected from deuterium, cyano, fluoro, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

In some embodiments, the first compound is selected from the group consisting of the compounds shown in a-1 to a-276 of claim 13.

In some embodiments, the second compound is selected from the group consisting of compounds shown in B1-B-162 and C-1-C-104 of claim 13.

The present application also provides a light emitting layer composition comprising a first compound having a structure represented by formula 1 and a second compound:

y is selected from S or O;

X ₁ and X ₂ One of them is-n=, the other is O or S;

ring a is selected from naphthalene or phenanthrene rings;

Each R is ₁ The same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, and carbon atomHeteroaryl groups of 3 to 20 or cycloalkyl groups of 3 to 10 carbon atoms; n is n ₁ R represents ₁ Is the number of (3); n is n ₁ Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;

the second compound has a structure represented by formula 2 or formula 3:

X ₃ and X ₄ One of them is-n=, the other is O or S;

Each R is ₂ And are the same or different and are each 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, and carbon atom3 to 12 trialkylsilyl groups, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms or cycloalkyl groups with 3 to 10 carbon atoms; n is n ₂ R represents ₂ Is the number of (3); n is n ₂ Selected from 0, 1, 2, 3, 4, 5, 6 or 7;

Each R is ₃ 、R ₄ And R is ₅ Are identical or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, and,Aryl with 6-20 carbon atoms, heteroaryl with 3-20 carbon atoms or cycloalkyl with 3-10 carbon atoms; optionally, any two adjacent R ₄ Forming a ring; n is n ₃ R represents ₃ Number n of (n) ₄ R represents ₄ Number n of (n) ₅ R represents ₅ Is the number of (3); n is n ₃ And n ₅ Each independently selected from 0, 1, 2, 3, 4, 5, or 6; n is n ₄ Selected from 0, 1 or 2.

Alternatively, the mass ratio of the first compound to the second compound in the light emitting layer composition is from 1:99 to 99:1, preferably from 10:90 to 90:10, more preferably from 30:70 to 70:30, even more preferably from 40:60 to 60:40.

The application also provides application of the luminescent layer composition to a luminescent layer of an organic electroluminescent device.

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

The organic electroluminescent device comprises an anode, a cathode, an anode and an organic layer which are oppositely arranged. The organic layer includes an organic light emitting layer including a first compound and a second compound.

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

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

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

To obtain a host material mixture, the first compound and the second compound may be mixed in a shaker to obtain a desired weight ratio of the mixture.

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, or the like, or a wet film forming method such as inkjet printing, nozzle printing, slit coating, spin coating, dip coating, flow coating method, or the like may be used.

In addition, the first compound and the second compound may be subjected to film formation in the above-listed methods, typically by a co-evaporation method or a mixed evaporation method. Co-evaporation is a hybrid deposition method in which two or more materials are placed in respective single crucible sources and current is applied to multiple cells 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 an electric current is applied to a cell to evaporate the materials.

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

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

In some aspects of the present application, an organic electroluminescent device includes, in order, an anode (e.g., an 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., mg—ag mixture), and an organic capping layer. 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 sequentially stacked.

In this application, anode 100 includes an anode material that preferably facilitates hole injection intoThe functional layer has a large work function (work function) material therein. Specific examples of the anode material include metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metal and oxide such as ZnO, al or SnO ₂ Sb; or conductive polymers such as poly (3-methylthiophene) and poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but not limited thereto. It is preferable to include a transparent electrode containing Indium Tin Oxide (ITO) as an anode.

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

In one embodiment, hole transport layer 321 consists of HT-1 or HT-5.

In one embodiment, hole adjustment layer 322 is comprised 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 a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, which are not particularly limited in this application. The material of the hole injection layer 310 may be selected from, for example, the following compounds or any combination thereof;

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

Alternatively, the organic light emitting layer 330 may include the host material and the guest material. Alternatively, the organic light emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be recombined at the organic light emitting layer 330 to form excitons, which transfer energy to the host material, which 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 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which are not particularly limited herein. Guest materials are also known as doping materials or dopants. Fluorescent dopants and phosphorescent dopants can be classified according to the type of luminescence. For example, specific examples of phosphorescent dopants 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 and second compounds. The guest material may be, for example, RD-1.

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

The electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from, but not limited to, bmppiphb, liQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, triazine derivatives, and the like. The material of the electron transport layer 340 comprises LiQ and other electron transport materials that may be selected from, but are not limited to, the following compounds:

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

In this application, 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 the cathode material 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 a multi-layer material such as LiF/Al, liq/Al, liO ₂ Al, liF/Ca, liF/Al and BaF ₂ and/Ca. Optionally, a metal electrode comprising magnesium and silver is included as a 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 an inorganic material such as an alkali metal sulfide, an alkali metal halide, or may include a complex of an alkali metal and an organic substance. In one embodiment of the present application, electron injection layer 350 comprises ytterbium (Yb).

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

According to one embodiment, as shown in fig. 2, the electronic device provided 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 type of electronic device, which may include, for example, but is not limited to, a computer screen, a cell phone screen, a television, an electronic paper, an emergency light, an optical module, etc.

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

Synthetic examples

Those skilled in the art will recognize that the chemical reactions described herein can be used to suitably prepare many of the heterocyclic compounds of the present application, and that other methods for preparing the compounds of the present application are considered to be within the scope of the present application. For example, the synthesis of those compounds not exemplified in accordance with the present application may be successfully accomplished by modification methods, such as appropriate protection of interfering groups, by use of other known reagents in addition to those described herein, or by some conventional modification of the reaction conditions, by those skilled in the art. None of the compounds mentioned in this application as synthetic methods are commercially available starting products.

Synthesis of the first compound:synthesis of 7-bromo-1-iodo-2-naphthalenethiol:

7-bromo-1-iodo-2-naphthylamine (CAS: 2411719-24-7, 17.40g,50 mmol) and deionized water (25 mL) were sequentially added to a 1000mL three-necked flask under nitrogen atmosphere, the system was cooled to 0℃with an ice-water bath, an aqueous solution (25 mL) of sodium nitrite (3.45 g,50 mmol) was added dropwise to the system, then an aqueous solution (25 mL) of potassium thiocyanate (9.72 g,100 mmol) and an aqueous solution (4.1 g,25 mmol) of ferric trichloride were added dropwise to the reaction system after the dropwise addition, and the system was allowed to slowly warm to room temperature after the dropwise addition and stirred overnight. The reaction solution was poured into deionized water (200 mL), extracted with methylene chloride (100 mL. Times.3), the organic phases were combined and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure after filtration to give a crude product, which was used in the next reaction without purification.

The resulting crude product, sodium sulfide nonahydrate (9.61 g,100 mmol), ethanol (180 mL) and deionized water (360 mL) were added in one portion to a 1000mL three-necked flask under nitrogen atmosphere, and the mixture was warmed to reflux and stirred for 16h. After the reaction system was cooled to room temperature, filtration was carried out, the filtrate was acidified to ph=2 with 1M hydrochloric acid, then extracted with dichloromethane (100 ml×3 times), the organic phases were combined and dried over anhydrous sodium sulfate, and after filtration, the solvent was distilled off under reduced pressure to obtain a crude product; purification by silica gel column chromatography using n-heptane as the mobile phase afforded a white solid (8.03 g, 44% yield). Synthesis of Sub-a 1:

7-bromo-2-phenylbenzoxazole (CAS: 1268137-13-8, 12.06g,44 mmol), pinacol biborate (12.28 g,48.4 mmol), potassium acetate (9.50 g,96.8 mmol) and 1, 4-dioxane (120 mL) were added sequentially to a 500mL three-necked flask under nitrogen atmosphere, stirring and heating were turned on, and tris (dibenzylideneacetone) dipalladium (Pd) was added rapidly until the system warmed to 40 ℃ ₂ (dba) 3,0.40g,0.44 mmol) and (2-dicyclohexylphosphine-2 ',4',6' triisopropylbiphenyl) (XPhos, 0.42g,0.88 mmol), the reaction was continued to warm to reflux and stirred overnight. After the system is cooled to room temperature, 200mL of water is added into the system, the system is fully stirred for 30min, the pressure is reduced, the filtration is carried out, a filter cake is washed to be neutral by deionized water, and then 100mL of absolute ethyl alcohol is used for leaching, and the filter cake is collected to obtain gray solid; the crude product was slurried once with n-heptane, purified by 200mL of toluene, passed through a silica gel column, the catalyst removed, and concentrated to give Sub-a1 (10.17 g, yield 72%) as a white solid.

Referring to the synthesis of Sub-a1, sub-a2 to Sub-a4 were synthesized using reactant a shown in table 1 instead of 7-bromo-2-phenylbenzoxazole.

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

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Synthesis of Sub-b 1:

to a 500mL three-necked flask under nitrogen atmosphere was successively added 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 0.58g,0.5 mmol), anhydrous sodium carbonate (10.60 g,100 mmol), toluene (180 mL), anhydrous ethanol (45 mL) and deionized water (45 mL), stirring and heating were turned on, and the temperature was raised to reflux for 16h. After the system was cooled to room temperature, it was extracted with methylene chloride (150 mL. Times.3 times), and the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off from the filtrate under reduced pressure to obtain a crude product. Purification by silica gel column chromatography using n-heptane as the mobile phase afforded a white solid (11.03 g, 53% yield).

Referring to the synthesis of Sub-a1, sub-B2 to Sub-B11 were synthesized using reactant Sub aX shown in table 2 instead of Sub-a1 and reactant B instead of 7-bromo-1-iodo-2-hydroxynaphthalene.

Table 2: synthesis of Sub-b2 to Sub-b11

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Synthesis of Sub-c 1:

sub-b1 (20.81 g,50 mmol), tert-butyl peroxybenzoate (BzOOt-Bu, 19.42g,100 mmol), palladium acetate (1.12 g,5 mmol), 3-nitropyridine (0.62 g,5 mmol), hexafluorobenzene (C) ₆ F ₆ 210 mL) and N, N' -dimethylimidazolidinone (DMI, 140 mL), stirring and heating were turned on, and the temperature was raised to 90 ℃ to react for 4 hours. After the system was cooled to room temperature, it was extracted with ethyl acetate (100 mL. Times.3 times), and the organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off from the filtrate under reduced pressure to obtain a crude product. Purification by silica gel column chromatography using n-heptane/dichloromethane as the mobile phase afforded a white solid (10.77 g, 52% yield).

Sub-c2 to Sub-c11 were synthesized with reference to Sub-c1 using Sub-bX shown in Table 3 instead of Sub-b 1.

Table 3: synthesis of Sub-c2 to Sub-c11

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Synthesis of Sub-c 11:

sub-c1 (10.36 g,25 mmol) and 200mL benzene-D6 were added to a 100mL three-necked flask under nitrogen atmosphere, and after heating to 60℃the trifluoromethanesulfonic acid (22.51 g,150 mmol) was added thereto, and the temperature was further raised to boiling and stirring for reaction for 24 hours. After the reaction system was cooled to room temperature, 50mL of heavy water was added thereto, and after stirring for 10 minutes, saturated K was added ₃ PO ₄ The reaction solution was neutralized with an aqueous solution. The organic layer was extracted with dichloromethane (50 mL. Times.3), the combined organic phases were dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure from the filtrate to obtain a crude product. Silica gel column chromatography using n-heptane/dichloromethane as mobile relative crudeSpectral purification gave Sub-c10 (6.82 g, 64% yield) as a white solid.

Synthesis of Sub-c 12:

sub-b12 (10.80 g,25 mmol), palladium dichloride (0.22 g,1.25 mmol) and DMSO (120 mL) were added to a 250mL three-necked flask under nitrogen atmosphere, and the mixture was stirred for 12 hours after the temperature was raised to 140 ℃. After the reaction system was cooled to room temperature, the organic layer was extracted with methylene chloride (50 mL. Times.3 times), the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off from the filtrate under reduced pressure to obtain a crude product. Purification by silica gel column chromatography using n-heptane/dichloromethane as the mobile phase afforded Sub-c13 (7.85 g, 73% yield) as a white solid.

Synthesis of Sub-d 1:

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

Referring to synthesis of Sub-d1, sub-d2 to Sub-d8 were synthesized using Sub-cX shown in Table 5 instead of Sub-C1, reactant C instead of 4-chlorobenzoic acid

Table 5: synthesis of Sub-d2 to Sub-d8

Preparation of Compound A2

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Intermediate Sub-c1 (35.0 g,84.8 mmol) was added to a round bottom flask, 350mL of THF was added to the flask after removal of water, the system was cooled to-80℃to-90℃with liquid nitrogen, and dropwise addition of n-butyllithium (6.5 g,101.4 mmol) was started, and the mixture was incubated for 1h. Trimethyl borate (11.4 g,109.8 mmol) was added dropwise, the temperature was kept at-80℃to-90℃and after 1h incubation, the reaction was allowed to spontaneously warm to room temperature, 100mL (2 mol/l concentration) of aqueous HCl solution was added after the completion of the reaction, and the mixture was stirred for 0.5h. Adding dichloromethane and water for liquid-separating extraction, washing the organic phase to neutral pH=7, mixing the organic phases, and anhydrous MgSO ₄ After drying for 10min, filtration, spin-drying of the filtrate and beating 2 times with n-heptane gave intermediate Sub-e1 (16.0 g, yield 50%) as a white solid.

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), tetrakis triphenylphosphine 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, and the mixture was heated to 76℃under nitrogen protection, heated under reflux, and stirred for 8h. After the reaction, the solution is cooled to room temperature, toluene and water are added to extract the reaction solution, the organic phases are combined, the organic layer is dried by anhydrous magnesium sulfate, filtered and concentrated; purification of the crude product by silica gel column chromatography gave solid compound A2 (16.8 g, yield 62%, m/z=643.2 [ m+h)] ⁺ )。

Sub-eX was synthesized with reference to Sub-c1 using reactant Sub-cX shown in Table 6 instead of Sub-c 1.

Table 6: synthesis of Sub-e2 to Sub-e10

The compound AX shown in the table below 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 7: synthesis of Compound AX

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Mass spectrometry analysis was performed on a part of the compounds synthesized above, to obtain the analysis results shown in table 8 below:

Table 8: mass spectrum data of compound AX

Compound A2	m/z＝643.2[M+H] ⁺	Compound A101	m/z＝657.1[M+H] ⁺
				Compound A13	m/z＝657.1[M+H] ⁺	Compound A114	m/z＝565.1[M+H] ⁺
Compound A4	m/z＝719.2[M+H] ⁺	Compound A147	m/z＝656.2[M+H] ⁺
				Compound A9	m/z＝667.2[M+H] ⁺	Compound A159	m/z＝595.2[M+H] ⁺
Compound A23	m/z＝693.2[M+H] ⁺	Compound A156	m/z＝577.2[M+H] ⁺
				Compound A46	m/z＝693.2[M+H] ⁺	Compound A136	m/z＝743.2[M+H] ⁺
Compound A34	m/z＝679.3[M+H] ⁺	Compound A268	m/z＝797.2[M+H] ⁺
				Compound A47	m/z＝567.1[M+H] ⁺	Compound A269	m/z＝723.1[M+H] ⁺
Compound A69	m/z＝673.1[M+H] ⁺	Compound A170	m/z＝684.1[M+H] ⁺
				Compound A84	m/z＝566.1[M+H] ⁺	Compound A171	m/z＝619.1[M+H] ⁺
Compound A62	m/z＝719.2[M+H] ⁺	Compound A172	m/z＝585.1[M+H] ⁺
				Compound A91	m/z＝567.1[M+H] ⁺

Synthesis of the second compound:

synthesis of intermediate sub-I-A1

1) Preparation of intermediate sub 1-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-6 (3.2 g,12.1 mmol) was added to a three-necked flask, and dried DMF (300 mL) solvent was added, and the temperature was raised to 150℃under nitrogen protection, and the temperature was maintained under stirring for 17 hours; cooling to room temperature and stopping stirring. Washing the reaction solution with water, separating an organic phase, drying the organic phase by using anhydrous magnesium sulfate, and removing a solvent under reduced pressure to obtain a crude product; purification by silica gel column chromatography using dichloromethane/n-heptane as mobile phase afforded the intermediate sub 1-I-A1 (26.3 g, 67% yield) as a white solid.

2) Preparation of intermediate sub 1-II-A1

Intermediate sub 1-I-A1 (26.0 g,80.6 mmol), o-chloroaniline (11.3 g,88.7 mmol), pd (dba) ₂ (0.73g，0.8mmol)，

2-dicyclohexylphosphorus-2, 4, 6-triisopropylbiphenyl (x-phos, 0.76g,1.6 mmol), sodium t-butoxide (11.6 g,121.0 mmol) was added to a three-necked flask, and toluene (300 mL) solvent was added thereto, and the temperature was raised to 110℃under nitrogen protection, and the mixture was stirred at the same temperature for 15 hours. Cooling to room temperature, stopping stirring, washing the reaction solution with water, separating out an organic phase, drying by using anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by silica gel column chromatography using dichloromethane/n-heptane as mobile phase afforded intermediate sub 1-I-A1 (15.7 g, 53% yield) as a white solid.

3) Preparation of intermediate sub-A1

Intermediate sub 1-I-A1 (15.0 g,46.5 mmol), cesium carbonate (37.9 g,116.3 mmol), tricyclohexylphosphonium fluoroborate (8.5 g,23.2 mmol), pd (dba) ₂ (0.52 g,2.3 mmol) was added to a three-necked flask, and toluene (150 mL) solvent was added thereto, and the temperature was raised to 110℃under nitrogen protection, and the mixture was stirred at the maintained temperature for 10 hours. Cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying by using anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purifying by silica gel column chromatography using dichloromethane/n-heptane as mobile phase crude product,the product intermediate sub-A1 was obtained as a white solid (9.43 g, 61% yield).

In the following table, raw material 2 was substituted for 2-bromocarbazole, raw material 3 was substituted for iodobenzene, raw material 4 was substituted for o-chloroaniline, and intermediates Sub-A2 to Sub-a10 shown in table 9 below were synthesized by a similar method using Sub-A1:

table 9: synthesis of intermediates Sub-A2 to Sub-A10

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Synthesis of Compound B1

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 t-butoxide (5.2 g,154.1 mmol) were added to a three-necked flask, toluene (300 mL) solvent was added, and the temperature was raised to 110℃under nitrogen protection, and the mixture was kept at stirring for 15 hours; cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying by using anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by silica gel column chromatography using methylene chloride/n-heptane as the mobile phase afforded product B1 (9.9 g, 64% yield) as a white solid. Mass spectrometry: m/z=561.2 [ m+h ]] ⁺ 。

The following table intermediates sub-A2 to sub-a10, instead of intermediate sub-A1, raw material 5, instead of 1-bromo-4- (2-phenyl) benzene, were used to synthesize the compounds shown in table 10 below using a similar method:

table 10: synthesis of Compound BX

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Mass spectrometry analysis was performed on a part of the compounds synthesized above, to obtain the analysis results shown in table 11 below:

table 11: mass spectrum of compound BX

Compound B1	m/z＝561.2[M+H] ⁺	Compound B95	m/z＝641.2[M+H] ⁺
				Compound B2	m/z＝611.2[M+H] ⁺	Compound B96	m/z＝565.1[M+H] ⁺
Compound B5	m/z＝611.2[M+H] ⁺	Compound B93	m/z＝625.2[M+H] ⁺
				Compound B19	m/z＝625.2[M+H] ⁺	Compound B94	m/z＝641.2[M+H] ⁺
Compound B129	m/z＝625.2[M+H] ⁺	Compound B24	m/z＝611.2[M+H] ⁺
				Compound B162	m/z＝701.2[M+H] ⁺

C22 synthesis of compound:

10-chloro-2-phenylphenanthrene [3,4-D ] is added into a 250mL three-necked flask in sequence under the atmosphere of nitrogen]Oxazole (10.0 g,30.3 mmol), N-phenyl-4-benzidine (CAS: 32228-99-2,7.5g,30.9 mmol), tris (dibenzylideneacetone) dipalladium (0.27 g,0.3 mmol), (2-dicyclohexylphosphine-2 ',4',6' triisopropylbiphenyl) (X-phos, 0.28g,0.6 mmol), sodium t-butoxide (4.4 g,45.4 mmol) and toluene (100 mL) were warmed to reflux and reacted overnight with stirring. After the system was cooled to room temperature, it was extracted with methylene chloride (100 mL. Times.3 times), and the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to give a crude product. Silica gel column chromatography purification of the crude product with n-heptane as mobile phase gave compound C22 (12.7 g, yield 78%, m/z=539.2 [ m+h)] ⁺ )。

Referring to the synthesis of compound 3, the compounds in table 12 were synthesized using starting material 6 shown in table 12 instead of N-phenyl-4-benzidine.

Table 12: synthesis of Compound CX

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Synthesis of Compound C12

10-chloro-2-phenylphenanthrene [3,4-D ]]Oxazole (35.0 g,106.1 mmol), pinacol biborate (32.3 g,127.3 mmol), pd (dppf) Cl ₂ (0.7 g,1.1 mmol) and KOAc (20.8 g,212.2 mmol) were added to 1, 4-dioxane (350 mL) and reacted at 100℃under reflux for 12h. When the reaction is completed, CH is used ₂ Cl ₂ And extracting with water. Using MgSO ₄ The organic layer was dried and concentrated, and the resultant compound was subjected to silica gel column and recrystallization to obtain a 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), tetrakis triphenylphosphine 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, 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℃under nitrogen protection, and the mixture was heated under reflux and stirred for 18 hours. Cooling to room temperature, stopping stirring, washing the reaction solution with water, separating out an organic phase, drying by using anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; silicon using dichloromethane/n-heptane as mobile relative crudeColumn chromatography gave C12 (24.7 g, 68% yield, m/z=615.2 [ m+h ] ⁺ )。

Referring to the synthesis of compound C12, the compounds in Table 13 were synthesized using starting material 7 shown in Table 13 in place of N- (4-bromophenyl-) -N-phenyl-benzidine.

Table 13: synthesis of Compound CX

Mass spectrometry analysis was performed on a part of the compounds synthesized above, to obtain the analysis results shown in table 14 below:

table 14: mass spectrum of compound CX

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Organic electroluminescent device preparation and evaluation:

example 1: preparation of red organic electroluminescent device

The anode pretreatment is carried out by the following steps: in the thickness of in turnThe ITO/Ag/ITO substrate is subjected to surface treatment by utilizing ultraviolet ozone and O2: N2 plasma to increase the work function of an anode, and the surface of the ITO substrate is cleaned by adopting an organic solvent to remove impurities and greasy dirt on the surface of the ITO substrate.

On the experimental substrate (anode), PD: HT-1 was set at 2%: co-evaporation is carried out at an evaporation rate ratio of 98% to form a film with a thickness ofIs then vacuum evaporated with HT-1 on the Hole Injection Layer (HIL), shapedThickness of->Is provided.

Vacuum evaporating compound HT-2 on the hole transport layer to form a film having a thickness ofIs provided.

Next, on the hole-adjusting layer, a red light-emitting layer was prepared by a co-evaporation method using the compound A2 as a first host, the compound C22 as a second host, and RD-1 as a dopant. Performing co-evaporation on the compound A2 and the compound C22 and RD-1 according to the evaporation rate ratio of 49 percent to 2 percent to form the film with the thickness of Red light emitting layer (EML).

On the light-emitting layer, mixing and evaporating the compounds ET-1 and LiQ in a weight ratio of 1:1 to formA thick Electron Transport Layer (ETL) on which Yb is vapor deposited to form a thickness +.>Then magnesium (Mg) and silver (Ag) are mixed at a vapor deposition rate of 1:9, and vacuum vapor deposited on the electron injection layer to form a film having a thickness +.>Is provided.

In addition, the thickness of the vacuum evaporation on the cathode isAnd forming a cover layer, thereby completing the manufacture of the red organic electroluminescent device.

Examples 2 to 36

An organic electroluminescent device was prepared by the same method as in example 1, except that the light-emitting layer host combinations in table 15 below were used instead of the combinations of compounds A2 and C22 in example 1 when the light-emitting layers were fabricated.

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 main body combinations in table 15 below were used instead of the combinations of the compounds A2 and C22 in example 1, respectively, at the time of producing the light-emitting layer.

Wherein, in preparing each example and comparative example, the structures of the compounds used are as follows:

performance test was performed on the red organic electroluminescent devices prepared in examples 1 to 36 and comparative examples 1 to 3, specifically at 10mA/cm ² IVL performance of the device was tested under the conditions of T95 device lifetime at 20mA/cm ² The test was conducted under the conditions of (2) and the test results are shown in Table 15.

TABLE 15

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Referring to table 15 above, it can be seen that the organic electroluminescent device of the present invention employs two specific compounds as the host material of the light emitting layer, and has an improved light emitting efficiency of at least 11.5% and an improved lifetime of at least 12.9% as compared to the device of the comparative example.

Example 37: preparation of red organic electroluminescent device

On the experimental substrate (anode), PD: HT-5 was set at 3%: co-evaporation is carried out at an evaporation rate of 97% to form a film with a thickness ofIs then vacuum evaporated with HT-5 on the hole injection layer to form a layer having a thickness +.>Is provided.

Vacuum evaporating compound HT-1 on the hole transport layer to form a film having a thickness ofIs provided.

Next, on the hole-adjusting layer, a red light-emitting layer was prepared by a co-evaporation method using the compound A2 as a first host, the compound B9 as a second host, and RD-1 as a dopant. Wherein the first body: uniformly mixing the second main body according to the weight ratio of 50:50 to obtain a composition; the composition of the host material: RD-1 is at 97%: vapor deposition rate ratio of 3% and vapor deposition thickness of Red light emitting layer (EML).

On the light-emitting layer, mixing and evaporating the compounds ET-3 and LiQ in a weight ratio of 1:1 to formA thick Electron Transport Layer (ETL) on which Yb is vapor deposited to form a thickness +.>Electron Injection Layer (EIL) of (a), then magnesium (Mg) and silver (Ag) in a 1:8 ratioMixing the vapor deposition rates, and vacuum evaporating on the electron injection layer to form a film with a thickness of +.>Is provided.

In addition, the thickness of the vacuum evaporation on the cathode isTo complete the manufacture of the red organic electroluminescent device.

Examples 37 to 45

An organic electroluminescent device was prepared by the same method as in example 37, except that the light-emitting layer host combinations in table 8 below were used instead of the combinations of the compounds A2 and B9 in example 1 when the light-emitting layers were fabricated.

Comparative examples 4 to 5

An organic electroluminescent device was prepared by the same method as in example 31, except that the light-emitting layer main body combinations in table 8 below were used instead of the combinations of the compounds A2 and B9 in example 31, respectively, at the time of producing the light-emitting layers.

performance test was performed on the red organic electroluminescent devices prepared in examples 37 to 45 and comparative examples 4 to 5, specifically at 10mA/cm ² IVL performance of the device was tested under the conditions of T95 device lifetime at 20mA/cm ² The test was conducted under the conditions of (2) and the test results are shown in Table 16.

Table 16

Referring to table 16 above, it can be seen that the organic electroluminescent device of the present invention employs two specific compounds as the host material of the light emitting layer, and has an improvement in light emitting efficiency of at least 16.5% and a T95 lifetime of at least 13.2% as compared to the device of the comparative example.

The preferred embodiments of the present invention have been described in detail above with reference to the accompanying drawings, but the present invention is not limited to the specific details of the above embodiments, and various simple modifications can be made to the technical solution of the present invention within the scope of the technical concept of the present invention, and all the simple modifications belong to the protection scope of the present invention.

Claims

1. An organic electroluminescent device includes 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 represented by formula 1:

y is selected from S or O;

X ₁ and X ₂ One of them is-n=, the other is O or S;

ring a is selected from naphthalene or phenanthrene rings;

Ar ₁ 、Ar ₂ and Ar is a group ₃ Identical or different and are each independently selected from substituted or unsubstituted aromatic groups having 6 to 40 carbon atomsA group, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

the second compound has a structure represented by formula 2 or formula 3:

X ₃ and X ₄ One of them is-n=, the other is O or S;

Ar ₇ and Ar is a group ₈ Identical or different and each is independentA substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

2. The organic electroluminescent device of claim 1, wherein the first compound is selected from structures shown in 1-1 to 1-15:

wherein Y is O or S.

3. The organic electroluminescent device according to claim 1, wherein, in the first compound, ar ₁ 、Ar ₂ And Ar is a group ₃ Each independently selected from the group consisting of substituted or unsubstituted groups W ₁ The method comprises the steps of carrying out a first treatment on the surface of the The unsubstituted group W ₁ Selected from the group consisting of:

4. The organic electroluminescent device according to claim 1, wherein, in the first compound, L ₁ 、L ₂ And L ₃ 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 phenanthrylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted benzoxazolylene group, a substituted or unsubstituted benzothiazolylene group;

alternatively, L ₁ 、L ₂ And L ₃ Substituent phase of (a)And are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, trifluoromethyl, tridentate methyl, trimethylsilyl or phenyl.

5. The organic electroluminescent device according to claim 1, wherein the second compound is selected from structures represented by formulae (2-1), (2-2) or (3-1) to (3-20):

6. the organic electroluminescent device according to claim 1, wherein in formula 2, ar ₄ 、Ar ₅ And Ar is a group ₆ Each independently selected from the group consisting of 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 triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoxazolyl, and substituted or unsubstituted benzimidazolyl;

alternatively, ar ₄ 、Ar ₅ And Ar is a group ₆ Each substituent of (a) is independently selected from deuterium, fluoro, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, t-butyl, phenyl, naphthyl, pyridinyl, dibenzofuranyl, dibenzothienyl or carbazolyl, optionally Ar ₄ And Ar is a group ₅ Any two ofThe adjacent substituents form benzene rings.

7. The organic electroluminescent device according to claim 1, wherein in formula 2, L ₄ 、L ₅ And L ₆ 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 phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted carbazole group.

8. The organic electroluminescent device according to claim 1, wherein in formula 1, each R ₁ Identical or different and are each independently selected from deuterium, cyano, fluoro, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl or carbazolyl;

alternatively, in formula 2, each R ₂ Identical or different and are each independently selected from deuterium, cyano, fluoro, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl or carbazolyl;

Alternatively, in formula 3, each R ₃ 、R ₄ And R is ₅ Identical or different and are each independently selected from deuterium, cyano, fluoro, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

9. The organic electroluminescent device according to claim 1, wherein in formula 3, L ₇ And L ₈ 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 phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted carbazole group;

10. The organic electroluminescent device according to claim 1, wherein in formula 3, ar ₇ And Ar is a group ₈ Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, and substituted or unsubstituted pyridyl.

11. The organic electroluminescent device of claim 1, wherein, in the first compound,andeach independently selected from the following groups:

alternatively, in the formula 2,and->Each independently selected from the following groups:

alternatively, in the formula 3,and->Each independently selected from the following groups:

12. the organic electroluminescent device of claim 1, wherein the organic light-emitting layer comprises a host material and a dopant, the host material comprising a first compound and a second compound; the mass ratio of the first compound to the second compound is 30:70-70:30.

13. The organic electroluminescent device of claim 1, wherein the first compound is selected from the group consisting of:

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preferably, the second compound is selected from the group consisting of:

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The second compound represented by formula 3 is selected from the following structures:

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14. an electronic device comprising the organic electroluminescent device as claimed in any one of claims 1 to 13.