CN111704621B

CN111704621B - Compound, display panel and display device

Info

Publication number: CN111704621B
Application number: CN202010589330.4A
Authority: CN
Inventors: 代文朋; 牛晶华; 高威; 张磊; 冉佺; 李侠
Original assignee: Wuhan Tianma Microelectronics Co Ltd
Current assignee: Wuhan Tianma Microelectronics Co Ltd
Priority date: 2020-06-24
Filing date: 2020-06-24
Publication date: 2021-11-30
Anticipated expiration: 2040-06-24
Also published as: CN111704621A

Abstract

The invention discloses a compound, a display panel and a display device. The compound has a structure shown in formula 1, wherein A, B, R¹～R³And m₁～m₃Each as defined herein. The compound provided by the invention can be used for display panels and display devices.

Description

Compound, display panel and display device

Technical Field

The invention belongs to the technical field of organic light emitting, and particularly relates to a compound, a display panel and a display device.

Background

An Organic Light Emitting Diode (OLED) is a self-emitting device that generates electroluminescence by using an organic thin film layer. Specifically, under the drive of an external electric field, the OLED is respectively injected with holes and electrons by an anode and a cathode; the hole and the electron respectively migrate to the light emitting layer and combine in the organic light emitting material to generate an exciton; the excitons in the excited state may release energy in the form of light back to a stable ground state, generating visible light. Different luminescent materials can be selected to generate different colors of emitted light, so that different color requirements can be met.

Generally, a Hole Transport Layer (HTL) including a Hole Transport Material (HTM) and an Electron Transport Layer (ETL) including an Electron Transport Material (ETM) are disposed in an OLED structure to help transport holes and electrons to an emission layer. In the OLED, the electron transport rate and the hole transport rate are balanced, so that the luminous quantum efficiency of the OLED device is improved. However, the commonly used HTM has a high hole transport capability, while the ETM has a much lower electron transport capability, resulting in a larger amount of holes than electrons migrating to the light emitting layer, which makes the electron and hole transport ratio of the whole device unbalanced, and greatly reduces exciton formation efficiency, affecting the light emitting efficiency of the OLED device.

Disclosure of Invention

Therefore, the invention provides a compound capable of improving the luminous efficiency of an OLED device, and a display panel and a display device comprising the compound.

In a first aspect of the invention, there is provided a compound having a structure represented by formula 1,

wherein the content of the first and second substances,

a represents a benzene ring or a 5-to 7-membered aromatic heterocycle,

to represent

Wherein Y is independentlyAnd is represented by a group of a carbon atom,

R¹、R²and R³Each independently represents a substituted or unsubstituted 5-to 40-membered azaaryl group, -PO (X)₂、—PS(X)₂Or (X)²)m₅-(X¹)m₄-, wherein

X independently represents a substituted or unsubstituted 6-to 40-membered aryl group or a substituted or unsubstituted 5-to 40-membered heteroaryl group,

X¹independently represents a C1-C20 alkyl group, a 3-20 membered cycloalkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a 3-20 membered heterocycloalkyl group, a 6-40 membered aryl group, or a 5-40 membered nitrogen heteroaryl group,

X²independently represent a substituted or unsubstituted 5-to 40-membered nitrogen heteroaryl group, a substituted or unsubstituted 6-to 40-membered aryl group, -PO (X)₂or-PS (X)₂，

m₄And m₅Each independently is 1,2 or 3, and (X)²)m₅-(X¹)m₄Having an azaaryl group in the formula-, -PO (X)₂and-PS (X)₂One or more of the above-mentioned (b) are,

m₁、m₂and m₃Each independently is 0, 1,2 or 3, and m₁+m₂+

m

₃1,2 or 3.

A second aspect of the present invention provides a display panel including an organic light emitting device including an anode, a cathode, and an organic thin film layer between the anode and the cathode, the organic thin film layer including a light emitting layer and an electron transport layer; the electron transport layer comprises at least one compound according to the first aspect of the present invention.

A third aspect of the invention provides a display device comprising a display panel as described in the second aspect of the invention.

It has been surprisingly found that the compound of the present invention has a suitable HOMO level and a deep LUMO level due to the compound having a parent nucleus comprising ring a and ring B and an appropriate functional group attached to the parent nucleus, can improve electron injection ability and electron mobility while effectively blocking holes, and also has a high triplet level, and can block excitons in a light emitting layer, thereby enabling an organic light emitting device employing the same to achieve lower turn-on and operating voltages and higher light emitting efficiency. Particularly, the compound also has excellent solubility and easy sublimation processability, so that an organic thin film layer adopting the compound has better film uniformity and stability, and the service life of a device is prolonged. The display panel and the display device of the present invention comprise the compound, and thus may have a lower driving voltage, a higher luminous efficiency, and a longer lifespan.

Drawings

In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings needed to be used in the embodiments of the present invention will be briefly described below, and it is obvious that the drawings described below are only some embodiments of the present invention, and it is obvious for those skilled in the art that other drawings can be obtained according to the drawings without creative efforts.

Fig. 1 is a schematic structural diagram of an organic light emitting device according to an embodiment of the present invention.

Fig. 2 is a schematic diagram of a display device according to an embodiment of the present invention.

Detailed Description

In order to make the objects, technical solutions and advantageous technical effects of the present invention more clear, the present invention is further described in detail with reference to the following embodiments. It should be understood that the embodiments described in this specification are only for the purpose of explaining the present invention and are not intended to limit the present invention.

The above summary of the present invention is not intended to describe each disclosed embodiment or every implementation of the present invention. The following description more particularly exemplifies illustrative embodiments. At various points throughout this application, guidance is provided through a list of embodiments that can be used in various combinations. In each instance, the list is merely a representative group and should not be construed as exhaustive.

In the description herein, it is to be noted that, unless otherwise specified, "above" and "below" are inclusive of the present number, and the meaning of "a plurality" or "plural" in "one or plural" is two or more.

The term "comprising" and its variants are not to be taken in a limiting sense when these terms appear in the description and claims.

The terms "a", "an", "the" each refer to one or more molecules of the compound, and are not limited to a single molecule of the compound. Furthermore, one or more molecules may or may not be the same, provided they fall within the category of the chemical compound.

The terms "preferred" and "preferably" refer to embodiments of the invention that may provide certain benefits under certain circumstances. However, other embodiments may also be preferred, under the same or other circumstances. Furthermore, the recitation of one or more preferred embodiments does not imply that other embodiments are not useful, and is not intended to exclude other embodiments from the scope of the disclosure.

Groupings of alternative elements or embodiments disclosed herein are not to be construed as limitations. Each group member may be employed and claimed individually or in any combination with other members of the group or other elements found herein. It is contemplated that one or more members of a group may be included in or deleted from the group for reasons of convenience and/or patentability. When any such inclusion or deletion occurs, the specification is considered herein to contain the modified group and thus satisfy the written description of all markush groups used in the appended claims.

When a compound or chemical structural feature (e.g., aryl, azaaryl, etc.) is referred to as "substituted," the feature may have one or more substituents, unless otherwise specified. The term "substituent" has the broadest meaning known to those of ordinary skill in the art and includes such fragments (moieity): which occupies the position normally occupied by one or more hydrogen atoms attached to the parent compound or chemical structural feature. In some embodiments, the substituent may be the sameCommon organic moieties known in the art may have a molecular weight (e.g., the sum of the atomic masses of the atoms of the substituents) of 15-50 g/mol, 15-100 g/mol, 15-200 g/mol, or 15-500 g/mol. Some substituents include F, Cl, Br, I, NO₂、C_1- ₁₂H_3-25、C_1-12H_1-25O、C_1-12H_1-25O₂、C_1-12H_3-26N、C_1-12H_1-26NO、C_1-12H_3-27N₂、C_1-12F_3-25Substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted C3-C10 heteroaryl, and the like.

The term "alkyl" includes not only straight-chain or branched-chain saturated hydrocarbon groups such as methyl, ethyl, propyl (e.g., n-propyl, isopropyl), butyl (e.g., n-butyl, isobutyl, sec-butyl, tert-butyl), pentyl (e.g., n-pentyl, isopentyl, neopentyl) and the like, but also alkyl substituents bearing other substituents known in the art, such as hydroxyl, alkylsulfonyl, halogen atoms, cyano, nitro, amino, carboxyl and the like. Thus, "alkyl" includes ether groups, haloalkyl groups, nitroalkyl groups, carboxyalkyl groups, hydroxyalkyl groups, sulfoalkyl groups, and the like. In various embodiments, the C1-C20 alkyl groups, i.e., alkyl groups, contain 1-20 carbon atoms.

The term "alkoxy" refers to-O-alkyl. Examples of alkoxy groups include, but are not limited to, methoxy, ethoxy, propoxy (e.g., n-propoxy, isopropoxy), butoxy (e.g., n-butoxy, isobutoxy, sec-butoxy, tert-butoxy), and the like.

The term "alkylthio" refers to-S-alkyl. Examples of alkylthio include, but are not limited to, methylthio, ethylthio, propylthio (e.g., n-propylthio, isopropylthio), butylthio (e.g., n-butylthio, isobutylthio, sec-butylthio, tert-butylthio), and the like.

The term "cycloalkyl" refers to a non-aromatic carbocyclic group, including cyclized alkyl, alkenyl, and alkynyl groups. Cycloalkyl groups can be monocyclic (e.g., cyclohexyl) or polycyclic (e.g., fused, bridged, and/or spiro rings). Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl.

The term "heterocycloalkyl" refers to a cycloalkyl group in which one or more of the atoms in the ring is an element other than carbon (e.g., N, O, S, etc.), and optionally contains one or more double or triple bonds. "optionally comprising" means that it may or may not be comprised. In some embodiments, the nitrogen atom of a cycloheteroalkyl group may contain one substituent, such as a hydrogen atom, an alkyl group, or other substituents as described herein. Examples of cycloheteroalkyl groups include, but are not limited to, morpholinyl, thiomorpholinyl, pyranyl, imidazolidinyl, imidazolinyl, oxazolidinyl, pyrazolidinyl, pyrazolinyl, pyrrolidinyl, pyrrolinyl, tetrahydrofuranyl, tetrahydrothienyl, piperidinyl, piperazinyl, and similar heterocycloalkyl groups. In various embodiments, the 3-20 membered heterocycloalkyl group, i.e., heterocycloalkyl group, can contain 3-20 carbon atoms for forming a ring.

The term "aryl" refers to a closed aromatic ring or ring system. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, indenyl, anthracenyl, phenanthrenyl, pyrenyl, spirobifluorenyl, and similar aryl groups. In various embodiments, the 6-to 40-membered aryl group, i.e., aryl group, can contain 6 to 40 carbon atoms for forming a ring.

The term "azaaryl" refers to an aryl group in which one or more of the atoms in the ring is a nitrogen atom. But does not exclude the case where one or more of the atoms in the ring of the aryl group is an element other than carbon, nitrogen (e.g., O, S, etc.). In some embodiments, the 5-40 membered azaaryl group, as a whole, can contain 1-10 or 1-6 ring nitrogen atoms. Further, the compound also optionally comprises 1-3 other ring heteroatoms (such as O, S and the like). Examples of azaaryls include, but are not limited to, pyrrolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazolyl (e.g., 1,2, 3-triazolyl, 1,3, 4-triazolyl, 1,2, 5-triazolyl), tetrazolyl, triazinyl (e.g., 1,3, 5-triazinyl), tetrazinyl, pyrazolyl, imidazolyl, isothiazolyl, thiazolyl, thiadiazolyl (e.g., 1,2, 3-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,2, 5-thiadiazolyl), isoxazolyl, oxazolyl, oxadiazolyl (e.g., 1,2, 3-oxadiazolyl, 1,3, 4-oxadiazolyl, 1,2, 5-oxadiazolyl), indolyl, isoindolyl, carbazolyl, phenanthrolinyl, quinolinyl, isoquinolinyl, quinoxalinyl, Quinazolinyl, acridinyl, benzotriazolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxadiazolyl, benzoxazolyl, cinnolinyl, 1H-indazolyl, 2H-indazolyl, indolizinyl, naphthyridinyl (e.g., 1, 8-naphthyridinyl, 1, 5-naphthyridinyl), phthalazinyl, pteridinyl, purinyl, oxazolopyridyl, thiazolopyridyl, imidazopyridinyl, furopyridinyl, thienopyridinyl, pyridopyrimidinyl, pyridopyrazinyl, pyridopyridazinyl, thienothiazolyl, thienooxazolyl, thienoimidazolyl, and similar heteroaryl groups. In various embodiments, a 5-40 membered heteroaryl, i.e., aryl, can contain 5-40 atoms (including carbon and heteroatoms) for forming a ring.

The term "azafused ring aryl" refers to a class of "azaaryl" groups in which two or more aromatic rings are fused together. Some examples of the azacondensed ring aromatic groups are listed in the above examples of the azaaryl groups, but not limited thereto.

The term "halo" or "halogen" refers to fluorine, chlorine, bromine and iodine, such as fluorine.

The term "hydrogen" means¹H (protium, H),²H (deuterium, D) or³H (tritium, T). In various embodiments, "hydrogen" may be¹H (protium, H).

Throughout this specification, substituents of compounds are disclosed in groups or ranges. It is expressly intended that such description include each individual sub-combination of members of these groups and ranges. For example, the term "C1-C6 alkyl" is expressly contemplated to disclose C1, C2, C3, C4, C5, C6, C1-C6, C1-C5, C1-C4, C1-C3, C1-C2, C2-C6, C2-C5, C2-C4, C2-C3, C3-C6, C3-C5, C3-C4, C4-C6, C4-C5, and C5-C6 alkyl, individually. As other examples, integers ranging from 5 to 40 are expressly contemplated to disclose individually 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, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, and 40; integers in the range of 1 to 20 are expressly contemplated to disclose 1,2,3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 and 20 individually. Accordingly, other groups or ranges are expressly contemplated.

Herein, the expression that a single bond crosses a single ring or multiple ring system means that a single bond may be attached at any accessible position of the single ring or multiple ring system.

In an embodiment of the first aspect, the present invention provides a compound having the structure shown in formula 1,

wherein the content of the first and second substances,

a represents a benzene ring or a 5-to 7-membered aromatic heterocycle,

to represent

Wherein Y independently represents O or S,

m₁、m₂and m₃Each independently is 0, 1,2 or 3, and m₁+m₂+

m

₃1,2 or 3.

In some embodiments, the compound may have a structure represented by formula 1-A, formula 1-B, or formula 1-C,

wherein R is¹、R²、R³、m₁、m₂And m₃Each as defined herein.

In any of the above embodiments, Y may represent O.

In any of the above embodiments, Y may also represent S.

In any of the above embodiments, a may be a phenyl ring.

In some embodiments, a is a phenyl ring and Y represents O. For example, the compound may have a structure represented by any one of formulas 1-1, 1-2, or 1-3.

In other embodiments, a is a phenyl ring and Y represents S. For example, the compound may have a structure represented by formula 1-4, formula 1-5, or formula 1-6.

In some embodiments, in one or more of formulas 1-1 to 1-6, m is₁Is 0 or 1. E.g. m₁Is 1.

In some embodimentsWherein, in one or more of the formulae 1-1 to 1-6, m₂Is 0 or 1. E.g. m₂Is 0.

In some embodiments, in one or more of formulas 1-1 to 1-6, m is₃Is 0 or 1. E.g. m₃Is 0.

Non-limiting examples of formulae 1-1 to 1-6 can be represented by formulae 1-1a to 1-6a, respectively.

In one or more of formulae 1-1a to 1-6a, m₂And may be 0 or 1. E.g. m₂Is 0.

In embodiments where a is a phenyl ring, optionally, m₁R is¹、m₂R is²And m₃R is³One or more of the substituted or unsubstituted 9-to 40-membered aza-condensed ring aryl groups. Further, m₁R is¹One or more of the substituted or unsubstituted 9-to 40-membered aza-condensed ring aryl groups. The substituted or unsubstituted 9-40 membered aza fused ring aryl can be any of the examples described herein. For example, the signal may be any one of T1 to T13, T17 to T19, or may be T1 (e.g., T1a, T1b), T2 (e.g., T2a, T2b), T6 (e.g., T6a, T6b, T6c, T6d), T7 (e.g., T7a, T7b, T7c, T7d), T8 (e.g., T8a, T8b, T8c), T9 (e.g., T9a, T9b, T9c), T17, T18, or T19 (e.g., T19a, T19b, T19 c).

In embodiments where a is a phenyl ring, optionally, m₁R is¹、m₂R is²And m₃R is³Represents- (R) - (R)⁴)_a—PO(X)₂Wherein R is⁴Represents phenyl, naphthyl or anthracenyl, a is 0 or 1 and X is as defined herein. Further, m₁R is¹Represents- (R) - (R)⁴)_a—PO(X)₂. Alternatively, X independently represents phenyl, biphenyl or pyridyl, for example phenyl. For example, - (R)⁴)_a—PO(X)₂May be T21 or T22.

In embodiments where a is a phenyl ring, optionally, m₁R is¹、m₂R is²And m₃R is³Represents- (R) - (R)⁴)_a—PS(X)₂Wherein R is⁴Represents phenyl, naphthyl or anthracenyl, a is 0 or 1 and X is as defined herein. Further, m₁R is¹Represents- (R) - (R)⁴)_a—PS(X)₂. Alternatively, X independently represents phenyl, biphenyl or pyridyl, for example phenyl. For example, - (R)⁴)_a—PS(X)₂May be T20 or T23.

In embodiments where a is a phenyl ring, optionally, m₁R is¹、m₂R is²And m₃R is³Represents (X)²)m₅-(X¹)m₄-, in which X¹Independently represent a 9-to 40-membered aza-fused ring aryl group, a triazolyl group (e.g., 1,2, 3-triazolyl group, 1,3, 4-triazolyl group, 1,2, 5-triazolyl group), an oxadiazolyl group (e.g., 1,2, 3-oxadiazolyl group, 1,3, 4-oxadiazolyl group, 1,2, 5-oxadiazolyl group), or a thiadiazolyl group (e.g., 1,2, 3-thiadiazolyl group, 1,3, 4-thiadiazolyl group, 1,2, 5-thiadiazolyl group), X²Independently represents a substituted or unsubstituted 5-to 30-membered nitrogen heteroaryl group, or a substituted or unsubstituted 6-to 40-membered aryl group, X, m₄And m₅Each as defined herein. Further, m₁R is¹Represents (X)²)m₅-(X¹)m₄-. Alternatively, X¹Independently represents phenanthrolinyl, benzimidazolyl, quinolyl, isoquinolyl, quinoxalinyl, 1, 5-naphthyridinyl, triazolyl (e.g., 1,2, 3-triazolyl, 1,3, 4-triazolyl, 1,2, 5-triazolyl) or oxadiazolyl (e.g., 1,2, 3-oxadiazolyl, 1,3, 4-oxadiazolyl, 1,2, 5-oxadiazolyl). Alternatively, X²Independently represents phenyl, biphenyl or pyridyl, such as phenyl. Alternatively, m₄Is 1 or 2. Alternatively, m₅Is 1 or 2. For example, (X)²)m₅-(X¹)m₄May be T2 (e.g. T2a, T2b, etc.), T14, T15. T16, T17, T18 or T19 (e.g., T19a, T19b, T19 c).

A specific example of T1 may be

A specific example of T2 may be

A specific example of T6 may be

A specific example of T7 may be

A specific example of T8 may be

A specific example of T9 may be

A specific example of T19 may be

# denotes the ligation site. The attachment position of other indefinite attachment groups can likewise be adjusted to give different compounds.

In various embodiments, m₁R is¹、m₂R is²And m₃R is³The remaining ones of which are each as defined herein. E.g. m₁R is¹、m₂R is²And m₃R is³The remaining ones of (a) may independently represent any one of the groups represented as T1 to T37. Further, m₁R is¹、m₂R is²And m₃R is³The remaining ones of which may independently represent any of the groups represented by T24 to T34, or such as T24, T25 (e.g., T25a, T25b, T25c, T25d), T26 (e.g., T26a, T26b, T26c, T26d), T27 (e.g., T27a, T27b, T27c, T27d), or T28 (e.g., T28a, T28b, T28 c).

Specific examples of T25 are

Specific examples of T26 are

Specific examples of T27 are

Specific examples of T28 are

In some embodiments, specific examples of the compound in which a is a benzene ring may include, but are not limited to, compounds shown as P1 to P19.

Other examples of the compound in which a is a benzene ring may include, but are not limited to, compounds shown in P24 to P42.

Other examples of the compound in which a is a benzene ring may include, but are not limited to, compounds shown in P47 to P65.

In some embodiments, specific examples of the compound in which a is a benzene ring may include, but are not limited to, compounds shown as H1 to H19.

Other examples of compounds in which a is a benzene ring may include, but are not limited to, compounds shown in H24 to H42.

Other examples of compounds in which a is a benzene ring may include, but are not limited to, compounds shown in H47 to H65.

In some embodiments, a is a phenyl ring, and m is₁And m₂Independently of one another is 1 or 2, m₃Is 0 or 1, m₁+m₂+

m

₃2 or 3, R¹、R²And R³Each as defined herein.

In these embodiments, the compound may alternatively have a structure represented by formula 1-1b, formula 1-2b, or formula 1-3b,

further, the compound may have a structure represented by formula 1-1b-1, formula 1-2b-1, or formula 1-3b-1,

alternatively, the compound may have a structure represented by formula 1-4b, formula 1-5b, or formula 1-6b,

further, the compound may have a structure represented by formula 1-4b-1, formula 1-5b-1, or formula 1-6b-1,

in which A is a benzene ring, and m is₁And m₂Independently of one another is 1 or 2, m₃In each embodiment where m is 0 or 1₁R is¹、m₂R is²And m₃R is³One or more of which may independently represent a substituted or unsubstituted 5-to 40-membered nitrogen heteroaryl group, -PO (X)₂、—PS(X)₂Or (X)²)m₅-(X¹)m₄-, wherein X¹Independently represent a 6-to 40-membered aryl group or a 5-to 40-membered heteroaryl groupBasic group, X, X²、m₄And m₅Each as defined herein. For example, in these embodiments, m₁R is¹、m₂R is²And m₃R is³May each independently represent any one of the groups represented by T1 to T28. As another example, m₁R is¹、m₂R is²And m₃R is³Can independently represent T24, T25 (e.g., T25a, T25b, T25c, T25d), T26 (e.g., T26a, T26b, T26c, T26d), T27 (e.g., T27a, T27b, T27c, T27d) or T28 (e.g., T28a, T28b, T28 c).

In some embodiments, a is a phenyl ring, and m is₁And m₂Independently of one another is 1 or 2, m₃Specific examples of the compound of 0 or 1 may include, but are not limited to, compounds represented by P18, P19, P20 to P23. Other examples may include, but are not limited to, compounds shown as P41-P46, P64-P69.

In some embodiments, specific examples of the compound in which a is a benzene ring may include, but are not limited to, compounds shown as H18 to H23. Other examples may include, but are not limited to, compounds shown in H41-H46, H64-H69.

In some embodiments, A is a 5-7 membered heteroaromatic ring. The hetero atom of the aromatic heterocyclic ring can be one or more selected from N, S and O. For example, A is a furan ring, a thiophene ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, an oxepine ring, a thieepine ring, or the like. As another example, A is a furan ring, a thiophene ring, a pyridine ring, a pyrazine ring, an oxepine ring, or a thiepin ring.

In some embodiments, the compound has a structure shown in any one of formula 2-1 to formula 2-11,

wherein, y¹And y²Each independently represents O or S, R¹、R²、R³、m₁、m₂、m₃Each as defined herein.

In some embodiments, in one or more of formulas 2-1 through 2-5, y¹And y²All represent O. In other embodiments, in one or more of formulas 2-1 through 2-5, y¹And y²Both represent S.

In some embodiments, in one or more of formulas 2-6 through 2-9, y¹Represents O. In other embodiments, in one or more of formulas 2-6 through 2-9, y¹Represents S.

In some embodiments, in one or more of formulas 2-10 through 2-11, y¹And y²All represent O. In other embodiments, in one or more of formulas 2-10 through 2-11, y¹And y²Both represent S. In other embodiments, in one or more of formulas 2-10 through 2-11, y¹Represents O, y²Represents S. In other embodiments, in one or more of formulas 2-10 through 2-11, y¹Denotes S, y²Represents O.

In some embodiments, m is in one or more of formulas 2-1 through 2-11₁ Is 0 or 1. E.g. m₁Is 1.

In some embodiments, m is in one or more of formulas 2-1 through 2-11₂ Is 0 or 1. E.g. m₂Is 0.

In some embodiments, m is in one or more of formulas 2-1 through 2-11₃ Is 0 or 1. E.g. m₃Is 0.

In some embodiments, the compound has a structure shown in any one of formula 2a to formula 2e,

wherein R is¹As defined herein.

In some embodiments, the compound has a structure shown in any one of formula 2f to formula 2j,

wherein R is¹As defined herein.

In some embodiments, the compound has a structure shown in any one of formula 2k to formula 2h,

wherein R is¹As defined herein.

In some embodiments, the compound has a structure shown in any one of formula 2o to formula 2r,

wherein R is¹As defined herein.

In some embodiments, the compound has a structure shown in any one of formula 2s to formula 2t,

wherein R is¹As defined herein.

In some embodiments, the compound has a structure represented by formula 2u,

wherein R is¹As defined herein.

In embodiments where A is a 5-7 membered heteroaromatic ring, optionally, m₁R is¹、m₂R is²And m₃R is³Represents- (R) - (R)⁴)_a—PO(X)₂Wherein R is⁴Represents phenyl, naphthyl or anthracenyl, a is 0 or 1 and X is as defined herein. Further, m₁R is¹Represents- (R) - (R)⁴)_a—PO(X)₂. Alternatively, X independently represents phenyl, biphenyl or pyridyl, for example phenyl. For example, - (R)⁴)_a—PO(X)₂May be T21 or T22.

In embodiments where A is a 5-7 membered heteroaromatic ring, optionally, m₁R is¹、m₂R is²And m₃R is³Represents- (R) - (R)⁴)_a—PS(X)₂Wherein R is⁴Represents phenyl, naphthyl or anthracenyl, a is 0 or 1 and X is as defined herein. Further, m₁R is¹Represents- (R) - (R)⁴)_a—PS(X)₂. Alternatively, X independently represents phenyl, biphenyl or pyridyl, for example phenyl. For example, - (R)⁴)_a—PS(X)₂May be T20 or T23.

In embodiments where A is a 5-7 membered heteroaromatic ring, optionally, m₁R is¹、m₂R is²And m₃R is³One or more of them represents a substituted or unsubstituted 5-to 40-membered nitrogen heteroaryl group. Further, m₁R is¹One or more of them represents a substituted or unsubstituted 5-to 40-membered nitrogen heteroaryl group. The 5-40 membered azaaryl group can be any of the examples described herein. For example, it may be any one of T1 to T19, T24 to T34, or may be T1 (e.g., T1a, T1b), T2 (e.g., T2a, T2b), T6 (e.g., T6a, T6b, T6c, T6d), T7 (e.g., T7a, T7b, T7c, T7d), T8 (e.g., T8a, T8b, T8)c) T9 (e.g. T9a, T9b, T9c), T14, T15, T16, T17, T18, T19 (e.g. T19a, T19b, T19c), T24, T25 (e.g. T25a, T25b, T25c, T25d), T26 (e.g. T26a, T26b, T26c, T26d), T27 (e.g. T27a, T27b, T27c, T27d) or T28 (e.g. T28a, T28b, T28 c).

In embodiments where A is a 5-7 membered heteroaromatic ring, optionally, m₁R is¹、m₂R is²And m₃R is³Represents (X)²)m₅-(X¹)m₄-, in which X¹、X²、m₄And m₅Each as defined herein. Further, m₁R is¹Represents (X)²)m₅-(X¹)m₄-。

Alternatively, X¹Independently represent 6-40 membered aryl or 5-40 membered azaaryl. Further, X¹Independently represents a phenyl group, a naphthyl group, an anthracenyl group or a 5-to 18-membered heteroaryl group having 1 to 3 ring-forming N atoms. For example, X¹Independently represent a phenyl group, an anthracenyl group, a pyridyl group, a pyrimidyl group, a triazinyl group, an phenanthrolinyl group, a benzimidazolyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a 1, 5-naphthyridine group, a triazolyl group (e.g., a 1,2, 3-triazolyl group, a 1,3, 4-triazolyl group, a 1,2, 5-triazolyl group), an oxadiazolyl group (e.g., a 1,2, 3-oxadiazolyl group, a 1,3, 4-oxadiazolyl group, a 1,2, 5-oxadiazolyl group) or a thiadiazolyl group (e.g., a 1,2, 3-thiadiazolyl group, a 1,3, 4-thiadiazolyl group, a 1,2, 5-thiadiazolyl group).

Alternatively, m₄Is 1 or 2.

Alternatively, X²Independently represent a substituted or unsubstituted 5-40 membered nitrogen heteroaryl group, or a substituted or unsubstituted 6-40 membered aryl group. Further, X²May independently represent any one of groups represented by T1 to T37. For example, X²Independently represents phenyl, biphenyl or pyridyl, such as phenyl.

Alternatively, m₅Is 1 or 2.

Alternatively, (X)²)m₅-(X¹)m₄May be T2 (e.g. T2a, T2b, etc.), T14 to T19, T24 toAny one of T27, T32 to T34. For example, (X)²)m₅-(X¹)m₄It may be a group represented by T2 (e.g. T2a, T2b, etc.), T14, T15, T16, T17, T18, T19 (e.g. T19a, T19b, T19c), T24, T25 (e.g. T25a, T25b, T25c, T25d), T26 (e.g. T26a, T26b, T26c, T26d) or T27 (e.g. T27a, T27b, T27c, T27 d).

In some embodiments, specific examples of the compound in which A is a 5-7-membered aromatic heterocycle may include, but are not limited to, compounds represented by L1 to L25. Other examples may include, but are not limited to, compounds shown as L26-L51, L52-L77, L78-L102.

In some embodiments, specific examples of the compound in which A is a 5-7-membered aromatic heterocycle may include, but are not limited to, compounds represented by M1 to M25. Other examples may include, but are not limited to, compounds shown as M26-M51, M52-M76.

In some embodiments, specific examples of the compound in which a is a 5-7-membered aromatic heterocyclic ring may include, but are not limited to, compounds represented by K1 to K22, K23 to K44. Other examples may include, but are not limited to, the compounds shown as K23 through K44.

In some embodiments, specific examples of the compound in which A is a 5-7-membered aromatic heterocyclic ring may include, but are not limited to, compounds represented by K45 to K66.

In some embodiments, specific examples of the compound in which A is a 5-7-membered aromatic heterocycle may include, but are not limited to, compounds represented by J1 to J22. Specific examples may include, but are not limited to, compounds shown in J23 through J44.

In some embodiments, specific examples of the compounds in which A is a 5-7 membered aromatic heterocycle may include, but are not limited to, the compounds shown in I1 to I22. Other examples may include, but are not limited to, the compounds shown in I23-I44.

In some embodiments, specific examples of the compound in which A is a 5-7-membered aromatic heterocyclic ring may include, but are not limited to, compounds shown as G1 to G22.

The compounds of the invention can be prepared, for example, according to the following exemplary scheme I. The specific methods for carrying out each synthetic step are readily available to those skilled in the art from the relevant scientific literature or standard textbooks in the art, according to this exemplary scheme I. Unless otherwise indicated, commercially available or literature-known compounds are used as starting materials for the synthesis.

It is to be understood that, unless otherwise indicated, when typical or preferred process conditions (i.e., reaction temperatures, times, molar ratios of reactants, solvents, pressures, etc.) are given, other process conditions may also be used. The optimum reaction conditions may vary with the particular reactants or solvents used, but these conditions can be determined by one skilled in the art by routine optimization procedures. One skilled in the art of organic synthesis will recognize that the nature and order of the synthetic steps presented may be varied for the purpose of optimizing the production of the compounds described herein.

Scheme I

Wherein Z is¹、Z²、Z³And Z⁴Each independently represents a halogen. For example, Z¹、Z²、Z³And Z⁴Each independently represents F, Cl or Br. Y, A and R¹Each as defined herein.

The processes described herein may be monitored according to any suitable method known in the art. For example, product formation can be by spectroscopic means such as nuclear magnetic resonance spectroscopy (NMR, e.g. of¹H or¹³C) Infrared spectroscopy (IR), spectrophotometry (e.g. UV visible), Mass Spectrometry (MS) or by chromatography such as High Performance Liquid Chromatography (HPLC), Gas Chromatography (GC), Gel Permeation Chromatography (GPC) or Thin Layer Chromatography (TLC).

The compound of the present invention is useful for display panels and display devices. In some embodiments, the compounds of the present invention may have high solubility in conventional solvents (such as dichloromethane, chloroform, toluene, dimethylformamide DMF, tetrahydrofuran THF, ethanol, etc.), have good easy-sublimation processability, facilitate the preparation of organic thin film layers, and achieve good film-forming uniformity, and reduce or avoid the occurrence of voids.

In an embodiment of another aspect, the present invention provides a display panel including an organic light emitting device including an anode, a cathode, and a multi-layered organic thin film layer between the anode and the cathode, the multi-layered organic thin film layer including at least an emission layer (EML) and an Electron Transport Layer (ETL); wherein the electron transport layer contains any one or more of the compounds of the present invention.

In some embodiments, the electron transport layer may also optionally include other electron transport materials known in the art, such as one or more of the following:

and the like.

In some embodiments, the light emitting layer may include a light emitting material as is known in the art. Further, the light emitting material may include a host material and a guest material. Wherein the host material can be selected from host luminescent materials known in the art and/or any one or more of the compounds described herein. The guest material may be selected from guest light emitting materials known in the art. The host (guest) light emitting material known in the art may be a fluorescent light emitting material, a phosphorescent light emitting material, or the like, and may be a blue light emitting material, a green light emitting material, a red light emitting material, or the like.

In some embodiments, the anode material may include a metal (e.g., copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, etc., and alloys thereof), a metal oxide (e.g., indium oxide, zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), etc.), a conductive polymer (e.g., polyaniline, polypyrrole, poly (3-methylthiophene), etc.). In addition to the above materials and combinations thereof that facilitate hole injection, other known materials suitable for use as anodes may be included.

In some embodiments, the cathode can include a metal layer (e.g., aluminum, magnesium, silver, indium, tin, titanium, and the like, and alloys thereof), a multi-layer cathode formed by compounding a metal layer and a layer comprising one or more of a metal oxide and a metal halide (e.g., LiF/Al, LiO)₂/Al、BaF₂Al, etc.). In addition to the above materials and combinations thereof that facilitate electron injection, other known materials suitable for use as cathodes are also included.

In the display panel of the present invention, the organic thin film layers may further include other functional layers. As an example, other functional layers may include a Hole Blocking Layer (HBL). In some embodiments, the Hole Blocking Material (HBM) of the Hole Blocking Layer (HBL) may be selected from HBM known in the art (e.g., BCP, TPBi, TmPyPB, DPEPO, PO-T2T, TAZ, etc.) and/or any one or more of the compounds described herein.

In some embodiments, the other functional layers may further include a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), an Electron Injection Layer (EIL). The materials of the layers (e.g. hole injection material HIM, hole transport material HTM, electron blocking material EBM, electron injection material EIM) may each be selected from the corresponding materials known in the art.

Fig. 1 shows an organic light emitting device as an example, which includes a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, an electron injection layer 7, a cathode 8, and a cap layer 9, which are sequentially stacked. The hole transport layer 4 in the drawing is a composite layer structure including a first hole transport layer 41 and a second hole transport layer 42. The arrows in the figure indicate the light direction.

The display panel may be fabricated using methods known in the art. An exemplary method of fabrication includes: an anode is formed on a transparent or opaque smooth substrate, a plurality of organic thin film layers are formed on the anode, and a cathode is formed on the organic thin film layers. The organic thin film layer can be formed by a known film formation method such as evaporation, sputtering, spin coating, dipping, ion plating, or the like.

In another embodiment, the present invention provides a display device including the display panel according to the present invention. Examples of the display device include, but are not limited to, a mobile phone (e.g., the mobile phone 100 shown in fig. 2), a computer, a television, a smart watch, a smart car, a VR or AR helmet, and the like, which are not particularly limited in this respect.

Examples

The present disclosure is more particularly described in the following examples that are intended as illustrations only, since various modifications and changes within the scope of the present disclosure will be apparent to those skilled in the art. Unless otherwise indicated, all parts, percentages, and ratios reported in the following examples are on a weight basis, and all reagents used in the examples are commercially available or synthesized according to conventional methods and can be used directly without further treatment, and the equipment used in the examples is commercially available.

Example 1: synthesis of Compound P2

(1)

In a 100mL round-bottom flask, 3, 4-dibromofuran (15mmol), 3-chloro-9H-carbazole (18mmol), and K₂CO₃(40mol)、CuSO₄.5H₂Adding O (3.0mol) into dry dimethyl formamide DMF (60mL), controlling the temperature at 150 ℃ under the nitrogen atmosphere, and stirring for reaction for 5 hours; the intermediate obtained was filtered through a pad of celite; extracting the filtrate with ethyl acetate; then washing with 50mL of water for three times, and drying by adopting anhydrous magnesium sulfate; after filtration and evaporation, an organic phase is taken out, the solvent is removed by rotary evaporation, and silica gel column chromatography is carried out by using a mixed solution of ethyl acetate and petroleum ether with the volume ratio of 1:5 as eluent to obtain a solid intermediate product P2-1.

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value was 345.0 and the test value was 345.4.

(2)

In a 100mL round-bottom flask, intermediate P2-1(15mmol), K₂CO₃(40mmol) and (NHC) Pd (allyl) Cl (1.50mmol) were mixed with dry dimethylacetamide DMAc (60mL) and stirred at 130 ℃ under nitrogen for 48 h. The obtained intermediate product was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and then the crude product was purified by silica gel column chromatography using an ethyl acetate/petroleum ether mixed solution at a volume ratio of 1:4 as a eluent, to obtain intermediate product P2-2.

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value is 265.0 and the test value is 265.3.

(3)

Intermediate P2-2(15mmol) and potassium acetate (40mmol) were mixed with dry 1, 4-dioxane (60mL), Pd (PPh) in a 100mL round bottom flask₃)₂Cl₂(0.40mmol) and pinacol diboron (25mmol) were mixed and stirred at 90 ℃ under nitrogen for 48 hours. The obtained intermediate was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain intermediate P2-3(12.5mmol, 83%).

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value is 357.2 and the test value is 357.3.

(4)

In a 100mL round-bottom flask, P2-3(10mmol), P2-4(12mmol) and Pd (PPh)₃)₄(03mmol) was added to a mixture of toluene (30mL), ethanol (20mL) and aqueous potassium carbonate (12mmol) (10mL) and the reaction was refluxed under nitrogen for 12 h. The resulting mixture was cooled to room temperature, added to water and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to give the final product P2.

Characterization of P2:

elemental analysis results: c₃₄H₁₉N₃O, theoretical value: c84.11, H3.94, N8.65, O3.30; test values are: c84.10, H3.95, N8.63, O3.32;

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value is 485.2 and the test value is 485.3.

Example 2: synthesis of Compound P15

Similar to the preparation process of example 1, except that, in step (4),

in a 100mL round-bottom flask, P2-3(10mmol), P15-1(12mmol), 10% NiCl₂And Cs₂CO₃(10mmol) was added to acetonitrile (50mL) and reacted under microwave at 155 ℃ under nitrogen atmosphere for 12 h. The resulting mixture was cooled to room temperature, added to water and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to give the final product P15.

Characterization of compound P15:

elemental analysis results: c₂₈H₁₈NO₂P, theoretical value: c77.95, H4.21, N3.25, O7.42, P7.18; test values are: c77.96, H4.22, N3.24, O7.40, P7.18;

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value was 431.1 and the test value was 431.2.

Example 3: synthesis of Compound P4

Similar to the preparation process of example 1, except that, in step (4),

in a 100mL round-bottom flask, P2-3(10mmol), P4-1(12mmol) and Pd (PPh)₃)₄(0.5mmol) was added to a mixture of toluene (30mL), ethanol (20mL) and aqueous potassium carbonate (12mmol) (10mL) and the reaction was refluxed for 12h under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to give the final product P4.

Characterization of compound P4:

elemental analysis results: c₃₀H₁₈N₄O, theoretical value: c79.98, H4.03, N12.44, O3.55; test values are: c79.99, H4.02, N12.46, O3.53;

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: theoretical value is 450.2 and test value is 450.1.

Example 4: synthesis of Compound P11

Similar to the preparation process of example 2, except that, in step (4),

in a 100mL round-bottom flask, P2-2(15mmol), P11-1(18mmol), Cs₂CO₃(30mol)、CuSO₄.5H₂Adding O (3.0mol) into dry dimethyl formamide DMF (60mL), controlling the temperature at 150 ℃ under the nitrogen atmosphere, and stirring for reacting for 4 hours; the intermediate obtained was filtered through a pad of celite; extracting the filtrate with ethyl acetate; then washing with 50mL of water for three times, and drying by adopting anhydrous magnesium sulfate; after filtration and evaporation, takeAnd (3) taking out an organic phase, removing the solvent by rotary evaporation, and performing silica gel column chromatography by using an ethyl acetate/petroleum ether mixed solution with the volume ratio of 1:5 as eluent to obtain a product P11.

Characterization of compound P11:

elemental analysis results: c₂₉H₁₇N₃O, theoretical value: c82.25, H4.05, N9.92, O3.78; test values are: c82.24, H4.05, N9.93, O3.78;

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value is 423.1 and the test value is 423.0.

Example 5: synthesis of Compound P16

Similar to the preparation process of example 1, except that, in step (4),

in a 100mL round-bottom flask, P2-3(10mmol), P16-1(12mmol) and Pd (PPh)₃)₄(0.4mmol) was added to a mixture of toluene (30mL), ethanol (20mL) and aqueous potassium carbonate (12mmol) (10mL) and the reaction was refluxed for 12h under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to give the final product P16.

Characterization of compound P16:

elemental analysis results: c₃₄H₂₂NO₂P, theoretical value: c80.46, H4.37, N2.76, O6.30, P6.10; test values are: c80.45, H4.36, N2.77, O6.30, P6.12;

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value is 507.1 and the test value is 507.2.

Example 6: synthesis of Compound P21

(1)

In a 100mL round-bottom flask, 3, 4-dibromofuran (15mmol), 3, 6-dichloro-9H-carbazole (18mmol), and K₂CO₃(45mol)、CuSO₄.5H₂Adding O (3.5mol) into dry dimethyl formamide DMF (60mL), controlling the temperature at 150 ℃ under the nitrogen atmosphere, and stirring for reacting for 6 hours; the intermediate obtained was filtered through a pad of celite; extracting the filtrate with ethyl acetate; then washing with 50mL of water for three times, and drying by adopting anhydrous magnesium sulfate; after filtration and evaporation, an organic phase is taken out, the solvent is removed by rotary evaporation, and silica gel column chromatography is carried out by using a mixed solution of ethyl acetate and petroleum ether with the volume ratio of 1:5 as eluent to obtain a solid intermediate product P21-1.

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value is 380.9 and the test value is 381.0.

(2)

In a 100mL round-bottom flask, intermediate P21-1(15mmol), K₂CO₃(40mmol) and (NHC) Pd (allyl) Cl (1.50mmol) were mixed with dry dimethylacetamide DMAc (60mL) and stirred at 130 ℃ under nitrogen for 48 h. The obtained intermediate product was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and then the crude product was purified by silica gel column chromatography using an ethyl acetate/petroleum ether mixed solution at a volume ratio of 1:4 as a eluent, to obtain intermediate product P21-2.

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value is 299.0 and the test value is 299.2.

(3)

Intermediate P21-2(15mmol) and potassium acetate (50mmol) were mixed with dry 1, 4-dioxane (70mL), Pd (PPh) in a 100mL round bottom flask₃)₂Cl₂(0.40mmol)And pinacol diboron (35mmol) were mixed and stirred at 90 ℃ under a nitrogen atmosphere for 48 hours. The resulting intermediate was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain intermediate P21-3.

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value is 483.2 and the test value is 483.3.

(4)

In a 100mL round-bottom flask, P21-3(10mmol), P21-4(26mmol) and Pd (PPh)₃)₄(0.8mmol) was added to a mixture of toluene (30mL), ethanol (30mL) and aqueous potassium carbonate (12mmol) (10mL) and the reaction was refluxed for 16h under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to give the final product P21.

Characterization of P21:

elemental analysis results: c₂₆H₁₅N₃O, theoretical value: c81.02, H3.92, N10.90, O4.15; test values are: c81.03, H3.92, N10.91, O4.14;

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value is 385.1 and the test value is 385.3.

Example 7: synthesis of Compound H16

Compound H16 was prepared according to the procedure of example 5. The synthesis of compound H16 may specifically comprise the following steps:

(1)

in a 100mL round-bottom flask, 3, 4-dibromothiophene (15mmol), 3-chloro-9H-carbazole (18mmol), and K₂CO₃(40mol)、CuSO₄.5H₂Adding O (3.0mol) into dry dimethyl formamide DMF (60mL), controlling the temperature at 150 ℃ under the nitrogen atmosphere, and stirring for reaction for 5 hours; the intermediate obtained was filtered through a pad of celite; extracting the filtrate with ethyl acetate; then washing with 50mL of water for three times, and drying by adopting anhydrous magnesium sulfate; after filtration and evaporation, an organic phase is taken out, the solvent is removed by rotary evaporation, and silica gel column chromatography is carried out by using a mixed solution of ethyl acetate and petroleum ether with the volume ratio of 1:5 as eluent to obtain a solid intermediate product H16-1.

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value is 360.9 and the test value is 360.7.

(2)

In a 100mL round-bottom flask, intermediate H16-1(15mmol), K₂CO₃(40mmol) and (NHC) Pd (allyl) Cl (1.50mmol) were mixed with dry dimethylacetamide DMAc (60mL) and stirred at 130 ℃ under nitrogen for 48 h. The obtained intermediate product was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and then the crude product was purified by silica gel column chromatography using an ethyl acetate/petroleum ether mixed solution at a volume ratio of 1:5 as a eluent, to obtain intermediate product H16-2.

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value was 281.0 and the test value was 281.3.

(3)

Intermediate H16-2(15mmol) and potassium acetate (40mmol) were mixed with dry 1, 4-dioxane (60mL), Pd (PPh) in a 100mL round bottom flask₃)₂Cl₂(0.40mmol) and pinacol diboron (25mmol) were mixed and stirred at 90 ℃ under nitrogen for 48 hours. The intermediate obtained is cooled to room temperature, added to water and thenFiltration through a celite pad, extraction of the filtrate with dichloromethane, followed by washing with water, drying over anhydrous magnesium sulfate, filtration and evaporation, followed by purification of the crude product by silica gel column chromatography gave intermediate H16-3.

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value is 373.1 and the test value is 373.2.

(4)

In a 100mL round-bottom flask, H16-3(10mmol), H16-4(12mmol) and Pd (PPh)₃)₄(0.5mmol) was added to a mixture of toluene (30mL), ethanol (20mL) and aqueous potassium carbonate (12mmol) (10mL) and the reaction was refluxed for 14h under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water, then filtered through a pad of celite, the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, after filtration and evaporation, the crude product was purified by silica gel column chromatography to give the final product H16.

Characterization of compound H16:

elemental analysis results: c₃₄H₂₂NOPS, theoretical value: c77.99, H4.24, N2.68, O3.06, P5.92, S6.12; test values are: c77.98, H4.24, N2.69, O3.06, P5.91, S6.12;

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value was 523.1 and the test value was 523.2.

Example 8: synthesis of Compound L3

(1)

In a 100mL round-bottom flask, L3-1(20mmol), [ CpRuL₂(CH₃CN)][PF₆](18mmol)、H₂O (110mol) was added to dry THF (50mL) and the reaction was stirred for 10h under nitrogen at 70 ℃. The resulting intermediate was filtered through a pad of celite, and the filtrate was extracted with ethyl acetate, and then washed three times with 50mL of water, and with anhydrous waterDrying with magnesium sulfate, filtering, evaporating, taking out organic phase, removing solvent by rotary evaporation, and performing silica gel column chromatography with ethyl acetate/petroleum ether mixed solution at volume ratio of 1:8 as eluent to obtain solid intermediate product L3-2.

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value is 255.0 and the test value is 255.1.

(2)

Intermediate L3-2(15mmol) and potassium acetate (40mmol) were mixed with dry 1, 4-dioxane (60mL), Pd (PPh) in a 100mL round bottom flask₃)₂Cl₂(0.40mmol) and pinacol diboron (20mmol) were mixed and stirred at 90 ℃ under nitrogen for 48 h. The resulting intermediate was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain intermediate L3-3.

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value was 347.1 and the test value was 347.0.

(3)

In a 100mL round-bottom flask, L3-3(10mmol), L3-4(12mmol) and Pd (PPh)₃)₄(0.4mmol) was added to a mixture of toluene (30mL), ethanol (20mL) and aqueous potassium carbonate (12mmol) (10mL) and the reaction was refluxed for 12h under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain a final product L3.

Characterization of compound L3:

elemental analysis results: c₂₅H₁₄N₂O₂The theoretical value is as follows: c80.20, H3.77, N7.48, O8.55; test values are: c80.21, H3.78, N7.46, O8.55;

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value is 374.1, and the test value is 374.2.

Example 9: synthesis of Compound K3

(1)

In a 100mL round-bottom flask, 3, 4-dibromofuran (15mmol) and 6-chloro-9H-pyridine [4,3-b ] were placed]Indole (18mmol), K₂CO₃(30mol)、CuSO₄.5H₂O (3.0mol) was added to dry DMF (60mL) and the reaction was stirred for 7.5h under nitrogen at 150 ℃. Filtering the obtained intermediate through a kieselguhr pad, extracting the filtrate with ethyl acetate, then washing with 50mL of water for three times, drying by adopting anhydrous magnesium sulfate, filtering and evaporating, taking out an organic phase, removing the solvent by rotary evaporation, and performing silica gel column chromatography by adopting an ethyl acetate/petroleum ether mixed solution with the volume ratio of 1:6 as eluent to obtain a solid intermediate K3-1.

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: theoretical value is 348.0, test value is 347.9.

(2)

In a 100mL round-bottom flask, intermediate K3-1(15mmol), K₂CO₃(40mmol) and (NHC) Pd (allyl) Cl (1.50mmol) were combined with dry DMAc (60mL) and stirred at 130 ℃ under nitrogen for 48 h. The obtained intermediate was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and then the crude product was purified by silica gel column chromatography using an ethyl acetate/petroleum ether mixed solution at a volume ratio of 1:5 as an eluent, to obtain intermediate K3-2.

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value is 266.0 and the test value is 266.1.

(3)

Intermediate K3-2(15mmol) and potassium acetate (40mmol) were mixed with dry 1, 4-dioxane (60mL), Pd (PPh) in a 100mL round bottom flask₃)₂Cl₂(0.40mmol) and pinacol diboron (20mmol) were mixed and stirred at 90 ℃ under nitrogen for 48 h. The resulting intermediate was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain intermediate K3-3.

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value is 358.2 and the test value is 358.1.

(4)

In a 100mL round-bottom flask, K3-3(10mmol), K3-4(12mmol) and Pd (PPh)₃)₄(0.4mmol) was added to a mixture of toluene (30mL), ethanol (20mL) and aqueous potassium carbonate (12mmol) (10mL) and the reaction was refluxed for 12h under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain the final product K3.

Characterization of compound K3:

elemental analysis results: c₃₂H₁₉N₃O, theoretical value: c83.28, H4.15, N9.10, O3.47; test values are: c83.29, H4.16, N9.10, O3.45;

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value is 461.2 and the test value is 461.3.

Example 10: synthesis of Compound J3

(1)

In a 100mL round-bottom flask, 3, 4-dibromothiophene (15mmol) and 6-chloro-9H-pyridine [4,3-b ] were placed]Indole (18mmol), K₂CO₃(30mol)、CuSO₄.5H₂O (3.0mol) was added to dry DMF (60mL) and the reaction was stirred for 6h under nitrogen at 150 ℃. Filtering the obtained intermediate through a kieselguhr pad, extracting the filtrate with ethyl acetate, then washing with 50mL of water for three times, drying by adopting anhydrous magnesium sulfate, filtering and evaporating, taking out an organic phase, removing the solvent by rotary evaporation, and performing silica gel column chromatography by adopting an ethyl acetate/petroleum ether mixed solution with the volume ratio of 1:6 as eluent to obtain a solid intermediate J3-1.

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value was 363.9 and the test value was 363.8.

(2)

In a 100mL round-bottom flask, intermediate J3-1(15mmol), K₂CO₃(40mmol) and (NHC) Pd (allyl) Cl (1.50mmol) were combined with dry DMAc (60mL) and stirred at 130 ℃ under nitrogen for 48 h. The resulting intermediate was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and then the crude product was purified by silica gel column chromatography using an ethyl acetate/petroleum ether mixed solution at a volume ratio of 1:5 as an eluent, to obtain intermediate J3-2.

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value is 282.0 and the test value is 282.2.

(3)

Intermediate J3-2(15mmol) and potassium acetate (40mmol) were reacted with dry 1, 4-dioxane (60 m) in a 100mL round bottom flaskL)、Pd(PPh₃)₂Cl₂(0.40mmol) and pinacol diboron (20mmol) were mixed and stirred at 90 ℃ under nitrogen for 48 h. The resulting intermediate was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain intermediate J3-3.

(4)

In a 100mL round-bottom flask, J3-3(10mmol), J3-4(12mmol) and Pd (PPh)₃)₄(0.4mmol) was added to a mixture of toluene (30mL), ethanol (20mL) and aqueous potassium carbonate (12mmol) (10mL) and the reaction was refluxed for 12h under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain a final product J3.

Characterization of compound J3:

elemental analysis results: c₃₂H₁₉N₃S, theoretical value: c80.48, H4.01, N8.80, S6.71; test values are: c80.47, H4.00, N8.82, S6.71;

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value is 477.1 and the test value is 477.3.

Example 11: synthesis of Compound I13

(1)

In a 100mL round-bottom flask, I13-1(20mmol), [ CpRuL₂(CH₃CN)][PF₆](18mmol)、H₂O (110mol) was added to dry THF (50mL) under a nitrogen atmosphereThe temperature is controlled at 70 ℃, and the reaction is stirred for 10 hours. Filtering the obtained intermediate through a kieselguhr pad, extracting the filtrate with ethyl acetate, then washing with 50mL of water for three times, drying by adopting anhydrous magnesium sulfate, filtering and evaporating, taking out an organic phase, removing the solvent by rotary evaporation, and performing silica gel column chromatography by adopting an ethyl acetate/petroleum ether mixed solution with the volume ratio of 1:7 as eluent to obtain a solid intermediate product I13-2.

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value was 281.0 and the test value was 281.1.

(2)

Intermediate I13-2(15mmol) and potassium acetate (40mmol) were mixed with dry 1, 4-dioxane (60mL), Pd (PPh) in a 100mL round bottom flask₃)₂Cl₂(0.40mmol) and pinacol diboron (20mmol) were mixed and stirred at 90 ℃ under nitrogen for 48 h. The resulting intermediate was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain intermediate I13-3.

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value is 373.2 and the test value is 373.0.

(3)

In a 100mL round-bottom flask, I13-3(10mmol), I13-4(12mmol) and Pd (PPh)₃)₄(0.4mmol) was added to a mixture of toluene (30mL), ethanol (20mL) and aqueous potassium carbonate (12mmol) (10mL) and the reaction was refluxed for 12h under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water and then filtered through a pad of celite, the filtrate was extracted with dichloromethane and then washed with water and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to give final product I13.

Characterization of compound I13:

elemental analysis results: c₂₄H₁₃N₃O₂The theoretical value is as follows: c76.79, H3.49, N11.19, O8.52; test values are: c76.78, H3.48, N11.19, O8.54;

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: theoretical 375.1, test 375.2.

Example 12: synthesis of Compound DI

Similar to the preparation process of example 1, except that, in step (4),

in a 100mL round-bottomed flask, P1-3(10mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (12mmol) and Pd (PPh)₃)₄(0.3mmol) was added to a mixture of toluene (30mL), ethanol (20mL) and aqueous potassium carbonate (12mmol) (10mL) and the reaction was refluxed for 12h under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water and then filtered through a pad of celite, the filtrate was extracted with dichloromethane and then washed with water and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to give the final product DI.

Characterization of compound DI:

elemental analysis results: c₃₁H₁₈N₄O, theoretical value: c80.50, H3.92, N12.11, O3.46; test values are: c80.52, H3.90, N12.11, O3.47;

ESI-MS (M/z) (M +) was obtained by liquid chromatography-mass spectrometry: the theoretical value was 462.2 and the test value was 462.5.

Comparative example 1: compound CI

Comparative example 2: compound CII

Reference is made to the above examples for the preparation of compounds CI and CII.

Simulated calculation of energy levels of compounds

The energy levels of the compounds of the examples and comparative examples were calculated by simulation using the Density Functional Theory (DFT). The distribution of molecular front line orbitals HOMO and LUMO is obtained through optimization and calculation under the calculation level of B3LYP/6-31G (d) by a Guassian 09 package (Guassian Inc.), and the lowest singlet state energy level E of the compound is calculated based on a time-containing density functional theory (TDDFT) simulation_S1And lowest triplet energy level E_T1. The results are shown in Table 1.

TABLE 1

Compound (I)	HOMO(eV)	LUMO(eV)	E_S1(eV)	E_T1(eV)
					P2	-5.56	-1.83	3.13	2.73
P15	-5.73	-1.79	3.32	2.93
					P4	-5.63	-1.81	3.34	2.95
P11	-5.48	-1.78	3.38	2.94
					P16	-5.83	-1.90	3.30	2.90
P21	-5.79	-1.89	3.35	2.96
					H16	-5.73	-1.80	3.13	2.93
L3	-5.69	-1.88	3.34	3.06
					K3	-5.86	-1.85	3.00	2.97
J3	-5.87	-1.83	3.01	2.99
					I13	-5.96	-1.87	3.30	2.94
DI	-5.53	-1.77	3.31	2.70
					CI	-5.45	-1.56	3.41	2.66
CII	-5.69	-2.12	3.06	1.95

As can be seen from Table 1, the compounds provided by the present invention can have both a deeper LUMO level (e.g., < -1.7eV) and a higher LUMO levelLowest triplet level E_T1(e.g., > 2.7eV), facilitates injection and transport of electrons, and facilitates blocking of excitons of the light emitting layer. The compound is suitable for being used as an electron transport material, and can improve the electron mobility and the luminous efficiency of an organic light-emitting device.

Application example 1

The present application example provides an OLED device (organic light emitting device), as shown in fig. 1, including a substrate 1, an anode (ITO)2, a hole injection layer 3, a first hole transport layer 41, a second hole transport layer 42, a light emitting layer 5, an electron transport layer 6, an electron injection layer 7, a cathode 8 (magnesium silver electrode, magnesium silver mass ratio 9:1), and a cap layer 9(CPL) which are sequentially stacked. The arrows in the figure indicate the light direction.

The specific preparation steps of the OLED device are as follows:

1) cutting a glass substrate with an Indium Tin Oxide (ITO) anode (thickness of 15nm) into sizes of 50mm × 50mm × 0.7mm, performing ultrasonic treatment in isopropanol and deionized water for 30 minutes respectively, and then exposing to ozone for about 10min for cleaning, and mounting the cleaned glass substrate on a vacuum deposition device;

2) on the ITO anode layer, a hole injection layer material (compound b) and a p-doped material (compound a) are evaporated together in a vacuum evaporation mode, and the doping proportion is 3% (mass ratio); 5nm in thickness as a hole injection layer;

3) vacuum evaporating a hole transport material (compound c) on the hole injection layer to a thickness of 100nm to form a first hole transport layer;

4) vacuum evaporating a hole transport material (compound d) with the thickness of 5nm on the first hole transport layer to form a second hole transport layer;

5) a luminescent main body material compound e and a doping material compound f are evaporated on the second hole transport layer in vacuum together, the doping proportion is 3 percent (mass ratio), the thickness is 30nm, and the luminescent main body material compound e and the doping material compound f are used as a luminescent layer;

6) vacuum evaporating compound P2 with a thickness of 30nm on the luminescent layer to form an electron transport layer;

7) compound g and n-doped material (compound h) are evaporated on the electron transport layer in vacuum at the doping mass ratio of 1: 1; the thickness is 5nm, and the film is used as an electron injection layer;

8) vacuum evaporating a magnesium-silver electrode on the electron injection layer, wherein the mass ratio of Mg to Ag is 1:9, the thickness is 10nm, and the magnesium-silver electrode is used as a cathode;

9) a compound i was vacuum-deposited on the cathode to a thickness of 100nm as a cap layer.

Application examples 2 to 12 and application comparative examples 1 to 2

Similar to application example 1, except that the compound P2 in step (6) was replaced with the compounds of examples 2 to 12 and comparative examples 1 to 2, respectively.

Testing the current of the OLED device under different voltages by using a Keithley 2365A digital nano-voltmeter, and then dividing the current by the light-emitting area to obtain the current density of the OLED device under different voltages; testing the brightness and radiant energy flux density of the OLED device under different voltages by using a Konicaminolta CS-2000 spectroradiometer; according to the current density and the brightness of the OLED device under different voltages, the same current density (10 mA/cm) is obtained²) Operating Voltage and Current efficiency CE_(10mA/cm ²)(cd/A)，V_onIs a luminance of 1cd/m²A lower turn-on voltage; the lifetime LT95 (at 50 mA/cm) was obtained by measuring the time when the luminance of the OLED device reached 95% of the initial luminance²Under test conditions); the test data are shown in table 2.

TABLE 2

As can be seen from table 2, the display panel provided by the present invention has a lower driving voltage, a higher light emitting efficiency and a longer service life because the compound of the present invention is used as an electron transport material. For example, the lighting voltage may be 3.95V or less, or 3.83V or less; current efficiency CE_(10mA/cm ² ₎Can be more than or equal to 48cd/A, or 5.2cd/A or greater; the life LT95 may be 62h or more. Compared with comparative examples 1-2, the organic light-emitting device provided by application examples 1-12, especially application examples 1-11, has the advantages that the above performances are obviously improved, the organic compound provided by the invention has a deeper HOMO energy level, a deeper LUMO energy level and a higher triplet state energy level, the electron injection capability and the electron mobility can be improved, and excitons can be effectively blocked in the light-emitting layer, so that the organic light-emitting device adopting the organic light-emitting device as an electron transport material obtains lower driving voltage and higher light-emitting efficiency; meanwhile, the organic compound provided by the invention has good thermal stability and film-forming property, is beneficial to the stability of devices, and prolongs the service life of the devices.

While the invention has been described with reference to specific embodiments, the invention is not limited thereto, and various equivalent modifications and substitutions can be easily made by those skilled in the art within the technical scope of the invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.

Claims

1. A compound having a structure represented by formula 1,

wherein A represents a benzene ring, the compound having a structure represented by any one of formulas 1-1b to 1-6b,

R¹and R²Each independently represents a substituted or unsubstituted 5-to 40-membered azaaryl group, -PO (X)₂、—PS(X)₂Or (X)²)m₅—(X¹)m₄—，

Wherein X independently represents a substituted or unsubstituted 6-to 40-membered aryl group, or a substituted or unsubstituted 5-to 40-membered heteroaryl group,

X¹independently represents a 6-to 40-membered aryl group or a 5-to 40-membered heteroaryl group,

m₄And m₅Independently of one another is 1,2 or 3,

m₁and m₂Each independently is 1 or 2, and m₁+m₂2 or 3; or

A represents a 5-to 7-membered aromatic heterocycle,

to represent

Wherein Y independently represents O or S,

R¹、R²and R³Each independently represents a substituted or unsubstituted 5-to 40-membered azaaryl group, -PO (X)₂、—PS(X)₂Or (X)²)m₅—(X¹)m₄—，

m₄And m₅Each independently is 1,2 or 3, and (X)²)m₅—(X¹)m₄Having nitrogen thereinHeteroaryl, — PO (X)₂and-PS (X)₂One or more of the above-mentioned (b) are,

m₁、m₂and m₃Each independently is 0, 1,2 or 3, and m₁+m₂+m₃1,2 or 3.

2. A compound according to claim 1, wherein A represents a benzene ring,

m₁r is¹、m₂R is²At least one of (A) and (B) represents a substituted or unsubstituted 9-to 40-membered aza-condensed ring aryl group, or (X)²)m₅—(X¹)m₄Wherein, wherein

X¹Independently represent a 9-to 40-membered aza-condensed ring aryl group, a triazolyl group, an oxadiazolyl group or a thiadiazolyl group,

X²independently represents a substituted or unsubstituted 5-to 30-membered nitrogen heteroaryl group or a substituted or unsubstituted 6-to 40-membered aryl group,

X、m₄and m₅Are each as defined in claim 1.

3. The compound of claim 2, wherein the compound has a structure represented by any one of formula 1-1a to formula 1-6a,

4. a compound according to claim 2 or 3, wherein R is¹Represents any one of groups represented by T1 to T23,

5. the compound of claim 1, wherein the compound has a structure represented by any one of formula 1-1b-1 to formula 1-6b-1,

6. a compound of claim 5, wherein R is¹And R²Each independently represents any one of groups represented by T1 to T28,

7. the compound of claim 1, wherein the compound has a structure represented by any one of formula 2-1 to formula 2-11,

wherein, y¹And y²Each independently represents O or S, R¹、R²、R³、m₁、m₂、m₃Are each as defined in claim 1.

8. The compound of claim 1, wherein the compound has a structure represented by any one of formula 2a to formula 2u,

wherein R is¹As claimed in claim1 is defined as follows.

9. A compound according to claim 8,

R¹independently represent a substituted or unsubstituted 5-to 40-membered nitrogen heteroaryl group; alternatively, the first and second electrodes may be,

R¹independently represent (X)²)m₅—(X¹)m₄Wherein, X¹、X²、m₄And m₅Are each as defined in claim 1.

10. A compound according to claim 9, characterised in that X¹Independently represents phenyl, naphthyl, anthryl or 5-18-membered heteroaryl containing 1-3 ring-forming N atoms; and/or the presence of a gas in the gas,

X²independently represent any one of groups represented by T1 to T37,

11. a compound of claim 8, wherein R is¹Independently represents any one of groups represented by T1 to T34,

12. the compound of claim 1, wherein the compound is selected from any one of the following,

13. a display panel includes an organic light emitting device including an anode, a cathode, and an organic thin film layer between the anode and the cathode, the organic thin film layer including a light emitting layer and an electron transport layer; the electron transport layer comprises at least one compound according to any of claims 1 to 12.

14. The display panel according to claim 13, wherein the organic thin film layer comprises a hole blocking layer comprising the compound according to any one of claims 1 to 12.

15. A display device comprising the display panel of claim 13 or 14.