阅读说明：本技术 化合物、显示面板及显示装置 (Compound, display panel and display device ) 是由 冉佺 高威 牛晶华 张磊 代文朋 于 2020-06-24 设计创作，主要内容包括：本发明公开了一种化合物、显示面板及显示装置。化合物具有式1所示的结构,其中X、a<Sub>1</Sub>、a<Sub>2</Sub>、b<Sup>1</Sup>～b<Sup>16</Sup>、L<Sup>1</Sup>、L<Sup>2</Sup>、Q<Sup>1</Sup>、Q<Sup>2</Sup>、n<Sub>1</Sub>和n<Sub>2</Sub>分别如本文所定义。本发明提供的化合物可用于显示面板和显示装置。<Image he="293" wi="700" file="DDA0002555563110000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(The invention discloses a compound, a display panel and a display device. The compound has a structure shown in formula 1, wherein X, a 1 、a 2 、b 1 ～b 16 、L 1 、L 2 、Q 1 、Q 2 、n 1 And n 2 Each as defined herein. The compound provided by the invention can be used for display panels and display devices.)

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

wherein the content of the first and second substances,

x represents C (Y)¹)₂、O、S、Si(Y²)₂、N(Y³) Or PO (Y)⁴) Wherein Y is¹、Y²、Y³And Y⁴Each independently represents a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C20 alkylthio group, a substituted or unsubstituted 3-to 20-membered cycloalkyl group, a substituted or unsubstituted 6-to 40-membered aryl group, or a substituted or unsubstituted 5-to 40-membered heteroaryl group,

a₁and a₂Are each independently 0 or 1, respectively,

b¹～b¹⁶each independently represents-C (Y)⁵) or-N wherein Y⁵Independently represents hydrogen or a covalent single bond,

L¹and L²Each independently represents hydrogen, a substituted or unsubstituted 3-to 20-membered heterocycloalkyl group, a substituted or unsubstituted 6-to 40-membered aryl group, a substituted or unsubstituted 5-to 40-membered heteroaryl group, -PO (R)₂、-PS(R)₂、-R¹S(＝O)₂(R²) Or a group as shown in 1a, 1b or 1c, and L¹And L²When the catalyst is not hydrogen at the same time,

R、R¹and R²Each independently represents a substituted or unsubstituted 6-to 40-membered aryl group, or a substituted or unsubstituted 5 ℃A 40-membered heteroaryl group, a heteroaryl group,

R³、R⁴and R⁵Each independently represents hydrogen, C1-C8 alkyl, substituted or unsubstituted 6-to 40-membered aryl, substituted or unsubstituted 5-to 40-membered heteroaryl, C1-C8 alkyl substituted with 1-4 substituted or unsubstituted 6-to 40-membered aryl and/or substituted or unsubstituted 5-to 40-membered heteroaryl, and R³、R⁴And R⁵At least one of which has an aryl and/or heteroaryl group,

R⁶represents a substituted or unsubstituted 6-to 40-membered aryl group, a substituted or unsubstituted 5-to 40-membered heteroaryl group, a C1-C8 alkyl group substituted with 1 to 4 substituted or unsubstituted 6-to 40-membered aryl groups and/or substituted or unsubstituted 5-to 40-membered heteroaryl groups,

R⁷represents a 6-to 40-membered aryl group or a 5-to 40-membered heteroaryl group,

R⁸independently represents cyano, -PO (R)₂、-PS(R)₂、-R¹S(＝O)₂(R²) A substituted or unsubstituted 6-to 40-membered aryl group, or a substituted or unsubstituted 5-to 40-membered heteroaryl group,

n₃is 1,2,3 or 4,

Q¹and Q²Each independently represents hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C20 alkylthio group, a substituted or unsubstituted 3-to 20-membered cycloalkyl group, a substituted or unsubstituted 6-to 40-membered aryl group, or a substituted or unsubstituted 5-to 40-membered heteroaryl group,

n₁and n₂Each independently is 1,2,3 or 4.

2. A compound according to claim 1, wherein X represents S.

3. A compound according to claim 1, wherein X represents O.

4. A compound according to any one of claims 1 to 3, characterised in that b is¹～b⁴0 to 2 of them are-N ═ N; and/or, b⁹～b¹²0 to 2 of these are-N ═ N.

5. A compound according to claim 4, characterized in that b is¹～b¹⁶Are all-C (Y)⁵)＝。

6. The compound of claim 1, wherein the compound has a structure represented by any one of formula 1-1 to formula 1-10,

wherein L is¹And L²Each independently represents a substituted or unsubstituted 6-to 40-membered aryl group, a substituted or unsubstituted 5-to 30-membered heteroaryl group, -PO (R)₂、-PS(R)₂、-R¹S(＝O)₂(R²) Or a group as shown in 1a, 1b or 1c,

L¹c, L connected to position t1 or t2²C attached to r1 or r 2.

7. The compound of claim 1, wherein L is¹And L²One or two of them represent a substituted or unsubstituted 5-to 30-membered heteroaryl group.

8. The compound of claim 1, wherein L is¹And L²One or both of them represent a group shown as 1 c.

9. A compound of claim 8, wherein R is⁸Independently represents a cyano group, a substituted or unsubstituted 6-to 40-membered aryl group, or a substituted or unsubstituted 5-to 40-membered heteroaryl group.

10. A compound of claim 8, wherein R is⁸Independently represents any one of cyano, phenyl, biphenyl, or a group represented by P1 to P82,

wherein M represents C (Y)⁶)₂S or O, Y⁶Independently represent a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C20 alkylthio group, a substituted or unsubstituted 3-to 20-membered cycloalkyl group, a substituted or unsubstituted 6-to 40-membered aryl group, or a substituted or unsubstituted 5-to 40-membered heteroaryl group,

# denotes the ligation site.

11. A compound of claim 8, wherein R is⁷Represents a phenyl group, a biphenyl group, or a 5-to 10-membered heteroaryl group containing 1 to 3 nitrogen atoms.

12. The compound of claim 1, wherein L is¹And L²Each independently represents hydrogen or any one of groups represented by P1 to P92, and L¹And L²When the catalyst is not hydrogen at the same time,

wherein M independently represents C (Y)⁶)₂S or O, Y⁶Independently represents a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C20 alkylthio group, a substituted or unsubstituted 3-20 membered cycloalkyl group, a substituted or unsubstituted 6-40 membered aryl group, or a substituted or unsubstituted 5-40 membered heteroaryl group, # represents a linking position.

13. A compound of claim 1, wherein Q is₁And/or Q₂Is hydrogen.

14. The compound of claim 1, wherein the compound is selected from any one of H-1 to H-240,

15. 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 14.

16. The display panel according to claim 15, wherein the organic thin film layer comprises a hole blocking layer comprising the compound according to any one of claims 1 to 14.

17. The display panel according to claim 15, wherein the light-emitting material of the light-emitting layer comprises a host material and a guest material, and the host material comprises the compound according to any one of claims 1 to 14.

18. A display device comprising the display panel of any one of claims 15-17.

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 entire device unbalanced, and greatly reduces exciton formation efficiency, affecting the light emission quantum efficiency of the OLED.

In addition, the glass transition temperature (Tg) of the currently used ETM is low (< 85 ℃), causing joule heat to be generated during operation of the OLED, resulting in molecular degradation and structural changes of the molecules, thereby reducing the efficiency and thermal stability of the assembly and also shortening the life of the assembly.

Disclosure of Invention

Accordingly, the present invention provides a compound having both high electron transport performance and glass transition temperature, and a display panel and a display device including the same.

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

wherein, X, a₁、a₂、b¹～b¹⁶、L¹、L²、Q¹、Q²、n₁And n₂Each as defined herein.

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 contains at least one compound according to the first aspect of the present invention.

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

It has been surprisingly found that the present invention is achieved by introducing a spiro group and L onto an aromatic fused cyclic quinone¹And/or L²A group such that the compound has a suitable HOMO level and a lower LUMO level, thereby increasing the electric potentialThe sub-injection and transmission capability can obtain lower working voltage and can effectively block holes; and the compound also has higher triplet state energy level, can block exciton diffusion of a light emitting layer, and achieves higher exciton utilization rate. Therefore, the organic light-emitting device can obtain higher luminous efficiency by adopting the compound of the invention. In addition, the spiro group is introduced to the aromatic fused ring quinone, so that the molecular effect is reduced, the aromatic fused ring quinone has proper space distortion, the intermolecular stacking can be reduced, the crystallization is prevented, and the film forming property and the film stability are good, so that the reduction of the electron transport property and the exciton formation efficiency caused by the material crystallization can be inhibited, and the luminous efficiency and the service life of the device can be improved. 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, unless otherwise specified, "above" and "below" are inclusive of the present numbers, and "one or more", "one or more" and "plural" mean two or more.

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 term "comprises" and its variants do not have a limiting meaning when presented in the description and claims.

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 claims.

When a compound or a chemical structural feature (e.g., aryl) is referred to as "substituted," the feature may have one or more substituents, unless otherwise specified. The term "substituent" has the most obvious meaning known to those of ordinary skill in the artBroad meaning 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 a common organic moiety known in the art, which may have a molecular weight (e.g., the sum of the atomic masses of the atoms of the substituent) of 15 to 50g/mol, 15 to 100g/mol, 15 to 200g/mol, or 15 to 500 g/mol. Some substituents include F, Cl, Br, I, NO₂、C_1-12H_3-25、C_{1- 12}H_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, can 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. In various embodiments, the 3-20 membered cycloalkyl group can contain 3-20 carbon atoms for forming a ring.

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 "heteroaryl" refers to an aryl group in which one or more of the atoms in the ring is an element other than carbon (e.g., N, O, S, etc.). In some embodiments, the 5-40 membered heteroaryl group, as a whole, can include 1-10 or 1-6 ring heteroatoms (e.g., N, O, S, etc.). Examples of heteroaryl groups include, but are not limited to, pyrrolyl, furanyl, thienyl, pyridyl, 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, isoxazolyl, oxazolyl, oxadiazolyl (e.g., 1,3, 4-oxadiazolyl, 1,2, 5-oxadiazolyl), indolyl, isoindolyl, carbazolyl, phenanthrolinyl, benzofuranyl, benzothienyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, acridinyl, benzotriazolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, tetrazolyl, pyrazinyl, pyrazyl, and the like, Benzoxadiazolyl, benzoxazolyl, cinnolinyl, 1H-indazolyl, 2H-indazolyl, indolizinyl, isobenzofuranyl, naphthyridinyl (e.g., 1, 8-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 aryl group, i.e., an aryl group, can contain 5-40 atoms (including carbon and heteroatoms) for forming a ring.

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 to C8 alkyl" is specifically contemplated to disclose C1, C2, C3, C4, C5, C6, C7, C8, C1 to C8, C1 to C7, C1 to C6, C1 to C5, C1 to C4, C1 to C3, C1 to C2, C2 to C8, C2 to C7, C2 to C6, C2 to C5, C2 to C4, C4 to C4, and C4 to C4. 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:

x represents C (Y)¹)₂、O、S、Si(Y²)₂、N(Y³) Or PO (Y)⁴) Wherein Y is¹、Y²、Y³And Y⁴Each independently represents a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C20 alkylthio group, a substituted or unsubstituted 3-to 20-membered cycloalkyl group, a substituted or unsubstituted 6-to 40-membered aryl group, or a substituted or unsubstituted 5-to 40-membered heteroaryl group;

a₁and a₂Each independently is 0 or 1;

b¹～b¹⁶each independently represents-C (Y)⁵) or-N wherein Y⁵Independently represents hydrogen or a covalent single bond, wherein when Y is⁵When represents a covalent single bond, it means L¹A group is attached to the C atom;

L¹and L²Each independently represents hydrogen, a substituted or unsubstituted 3-to 20-membered heterocycloalkyl group, a substituted or unsubstituted 6-to 40-membered aryl group, a substituted or unsubstituted 5-to 40-membered heteroaryl group, -PO (R)₂、-PS(R)₂、-R¹S(＝O)₂(R²) Or a group as shown in 1a, 1b or 1c, and L¹And L²When the catalyst is not hydrogen at the same time,

R、R¹and R²Each independently represents a substituted or unsubstituted 6-to 40-membered aryl group or a substituted or unsubstituted 5-to 40-membered heteroaryl group,

R³、R⁴and R⁵Each independently represents hydrogen, C1-C8 alkyl, substituted or unsubstituted 6-to 40-membered aryl, substituted or unsubstituted 5-to 40-membered heteroaryl, C1-C8 alkyl substituted with 1-4 substituted or unsubstituted 6-to 40-membered aryl and/or substituted or unsubstituted 5-to 40-membered heteroaryl, and R³、R⁴And R⁵At least one of which has an aryl and/or heteroaryl group,

R⁶represents a substituted or unsubstituted 6-to 40-membered aryl group, a substituted or unsubstituted 5-to 40-membered heteroaryl group, a C1-C8 alkyl group substituted with 1 to 4 substituted or unsubstituted 6-to 40-membered aryl groups and/or substituted or unsubstituted 5-to 40-membered heteroaryl groups,

R⁷represents a 6-to 40-membered aryl group or a 5-to 40-membered heteroaryl group,

R⁸independently represents cyano, -PO (R)₂、-PS(R)₂、-R¹S(＝O)₂(R²) A substituted or unsubstituted 6-to 40-membered aryl group, or a substituted or unsubstituted 5-to 40-membered heteroaryl group,

n₃is 1,2,3 or 4;

Q¹and Q²Each independently represents hydrogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylthio, substituted or unsubstituted 3-20 membered cycloalkyl, substituted or unsubstituted 6-40 membered aryl, or substituted or unsubstituted 5-40 membered heteroaryl;

n₁and n₂Each independently is 1,2,3 or 4.

In some embodiments, X represents S.

In other embodiments, X represents O.

In some embodiments, b¹～b⁸0 to 5 of these are-N ═ and/or, b⁹～b¹²0 to 5 of these are-N ═ N. E.g. b¹～b⁸0, 1 or 2 of which are-N ═ and/or, b⁹～b¹²0, 1 or 2 of which are-N ═ N. Further may be, b¹～b⁴0, 1 or 2 of which are-N ═ and/or, b⁹～b¹²0, 1 or 2 of which are-N ═ N.

In some embodiments, a₁And/or a₂Is 0. For example, a₁And a₂Is 0. In these embodiments, b may be¹～b⁴0, 1 or 2 of which are-N ═ and/or, b⁹～b¹²0, 1 or 2 of which are-N ═ N. When b is¹～b⁴When it contains-N, it may be b²、b³1 or 2 of is-N ═ e.g. b²Or b³is-N ═ N. When b is⁹～b¹²When it contains-N, it may be b¹⁰、b¹¹1 or 2 of is-N ═ e.g. b¹⁰Or b¹¹is-N ═ N.

In some embodiments, the compound can have a structure shown in formula 1-A,

in the formula 1-A, X, L¹、L²、Q¹、Q²、n₁And n₂Each as defined herein. Wherein L is¹When not hydrogen, b²And b³One of them is-C (Y)⁵) And Y⁵Represents a covalent single bond (i.e., L)¹To which C atom) the other represents-CH ═ or-N ═ or. L is¹When it is hydrogen, b²And b³Each independently represents-CH ═ or-N ═ or. L is²When not hydrogen, b¹⁰And b¹¹One of them is-C (Y)⁵) And Y⁵Represents a covalent single bond (i.e., L)²To which C atom) the other represents-CH ═ or-N ═ or. L is²When is hydrogen，b¹⁰And b¹¹Each independently represents-CH ═ or-N ═ or.

In some embodiments, the compound may have a structure shown in formula 1-1. Alternatively, the compound may have a structure represented by formula 1-2. Alternatively, the compounds may have the structures shown in formulas 1-3. Alternatively, the compounds may have the structures shown in formulas 1-4. Alternatively, the compounds may have the structures shown in formulas 1-5. Alternatively, the compounds may have the structures shown in formulas 1-6. Alternatively, the compounds may have the structures shown in formulas 1-7. Alternatively, the compounds may have the structures shown in formulas 1-8. Alternatively, the compounds may have the structures shown in formulas 1-9. Alternatively, the compounds may have the structures shown in formulas 1-10.

In formulae 1-1 to 1-10, L¹、L²、Q¹、Q²、n₁And n₂Respectively, when present, are as defined herein. Further, L¹And L²Independently at each occurrence, represents a substituted or unsubstituted 6-to 40-membered aryl group, a substituted or unsubstituted 5-to 30-membered heteroaryl group, -PO (R)₂、-PS(R)₂、-R¹S(＝O)₂(R²) Or a group as shown in 1a, 1b or 1 c. R, R therein¹、R²1a, 1b and 1c are each as defined herein. Further, L¹And L²Independently at each occurrence, represents a substituted or unsubstituted 6-40 membered aryl, substituted or unsubstituted 5-30 membered heteroaryl, or a group as shown in 1 c. Alternatively, in formulae 1-1 to 1-4, L¹Independently to the C at position t1 or t 2. Alternatively, in formulae 1-1, 1-3, 1-5, 1-6, 1-9, and 1-10, L²Independently to the C at position r1 or r 2.

In some embodiments, the compound can have a structure shown in formula 1-a. Alternatively, the compound may have a structure represented by formula 1-b. Alternatively, the compound may have a structure represented by formula 1-c. Alternatively, the compound may have a structure represented by formula 1-d. Alternatively, the compound may have a structure represented by formula 1-e. Alternatively, the compound may have a structure represented by formula 1-f.

In formulae 1-a to 1-f, L¹、L²、Q¹、Q²、n₁And n₂Respectively, when present, are as defined herein. Further, L¹And L²Independently at each occurrence, represents a substituted or unsubstituted 6-to 40-membered aryl group, a substituted or unsubstituted 5-to 30-membered heteroaryl group, -PO (R)₂、-PS(R)₂、-R¹S(＝O)₂(R²) Or a group as shown in 1a, 1b or 1 c. R, R therein¹、R²1a, 1b and 1c are each as defined herein. Further, L¹And L²Independently at each occurrence, represents a substituted or unsubstituted 6-40 membered aryl, substituted or unsubstituted 5-30 membered heteroaryl, or a group as shown in 1 c.

In any of the above embodiments, L¹And L²One or two of them may independently represent a substituted or unsubstituted 6-to 40-membered aryl group. The 6-to 40-membered aryl is as defined herein. In some embodiments, the 6-to 40-membered aryl group can include a 6-to 25-membered aryl group or a 6-to 14-membered aryl group. For example, examples of the 6-to 40-membered aryl group may include phenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, spirobifluorenyl.

In any of the above embodiments, L¹And L²One or two of them may independently represent a substituted or unsubstituted 5-to 40-membered heteroaryl group. The 5-to 40-membered heteroaryl is as defined herein. In some embodiments, the 5-40 membered heteroaryl group may include a 5-30 membered heteroaryl group, a 5-20 membered heteroaryl group, or a 5-14 membered heteroaryl group. For example, examples of 5-40 membered heteroaryl groups can be selected from the heteroaryl groups specifically described herein.

In any of the above embodiments, L¹And L²One or two of them may independently represent-PO (R)₂. R is as defined herein. Examples of R may be selected from aryl or heteroaryl groups as described herein. For example, R independently represents benzeneA naphthyl group, a hetero-benzene containing 1 to 3 nitrogen atoms or a hetero-naphthalene containing 1 to 3 nitrogen atoms. Or, R represents phenyl.

In any of the above embodiments, L¹And L²One or two of them may independently represent-PS (R)₂. R is as defined herein. Examples of R may be selected from aryl or heteroaryl groups as described herein. For example, R independently represents phenyl, naphthyl, a hetero-benzene containing 1 to 3 nitrogen atoms or a hetero-naphthalene containing 1 to 3 nitrogen atoms. Or, R represents phenyl.

In any of the above embodiments, L¹And L²One or two of which may independently represent-R¹S(＝O)₂(R²)。R¹And R²As defined herein. R¹And R²Examples of (a) may be independently selected from aryl or heteroaryl groups as described herein. For example, R¹And R²Independently represents phenyl, naphthyl, a hetero-benzene containing 1 to 3 nitrogen atoms or a hetero-naphthalene containing 1 to 3 nitrogen atoms. Or, R¹And R²Represents a phenyl group.

In any of the above embodiments, L¹And L²One or two of them may independently represent a group as shown in 1 c.

In any embodiment, R⁷Represents 6-40 membered aryl or 5-40 membered heteroaryl. R⁷Examples of (a) may be independently selected from aryl or heteroaryl groups as described herein. In some embodiments, R⁷Represents a phenyl group, a biphenyl group or a 5-to 10-membered heteroaryl group containing 1 to 3 nitrogen atoms. For example, R⁷Examples of (b) may include phenyl, pyrrolyl, furanyl, thienyl, pyridyl, pyridazinyl, pyrimidinyl, oxazolyl, oxadiazolyl (e.g., 1,3, 4-oxadiazolyl, 1,2, 5-oxadiazolyl), triazolyl (e.g., 1,2, 3-triazolyl, 1,3, 4-triazolyl, 1,2, 5-triazolyl), triazinyl (e.g., 1,3, 5-triazinyl), pyrazolyl, imidazolyl, isothiazolyl, thiazolyl, thiadiazolyl, isoxazolyl, oxazolyl, indolyl, isoindolyl, carbazolyl, phenanthrolinyl, benzofuranyl, benzothienyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzimidazolyl, benzothiazolylBenzisothiazolyl, benzisoxazolyl, benzoxadiazolyl, benzoxazolyl, cinnolinyl, naphthyridinyl (e.g. 1, 8-naphthyridinyl).

In any embodiment, R⁸Independently represents cyano, -PO (R)₂、-PS(R)₂、-R¹S(＝O)₂(R²) Substituted or unsubstituted 6-to 40-membered aryl, or substituted or unsubstituted 5-to 40-membered heteroaryl. For example, R⁸Independently represents a cyano group, a substituted or unsubstituted 6-to 40-membered aryl group, or a substituted or unsubstituted 5-to 40-membered heteroaryl group. The 6-to 40-membered aryl group can include the aryl groups described herein. The 5-40 membered heteroaryl group can include heteroaryl groups described herein.

In any embodiment, R⁸Independently represent any one of cyano, phenyl, biphenyl, or a group represented by P1 to P82,

wherein M represents C (Y)⁶)₂S or O, Y⁶Independently represents a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C20 alkylthio group, a substituted or unsubstituted 3-20 membered cycloalkyl group, a substituted or unsubstituted 6-40 membered aryl group, or a substituted or unsubstituted 5-40 membered heteroaryl group, # represents a linking position.

Examples of P1 at each occurrence can include, but are not limited to, P1a, P1b, P1 c. Examples of P6 at each occurrence can include, but are not limited to, P6a, P6b, P6 c. Examples of P12 at each occurrence may include, but are not limited to, P12a, P12 b. Examples of P13 at each occurrence can include, but are not limited to, P13a, P13 b. Examples of P14 at each occurrence may include, but are not limited to, P14a, P14 b. Examples of P42 at each occurrence may include, but are not limited to, P42a, P42 b. Examples of P43 at each occurrence may include, but are not limited to, P43a, P43 b. Examples of P44 at each occurrence may include, but are not limited to, P44a, P44 b. Examples of P45 at each occurrence can include, but are not limited to, P45a, P45 b. Examples of P46 at each occurrence may include, but are not limited to, P46a, P46 b. Examples of P47 at each occurrence can include, but are not limited to, P47a, P47 b. Examples of P48 at each occurrence may include, but are not limited to, P48a, P48 b. Examples of P49 at each occurrence may include, but are not limited to, P49a, P49 b. Examples of P50 at each occurrence can include, but are not limited to, P50a, P50 b. Examples of P51 at each occurrence can include, but are not limited to, P51a, P51 b. Examples of P55 at each occurrence may include, but are not limited to, P55a, P55 b. Examples of P62 at each occurrence may include, but are not limited to, P62a, P62 b. Examples of P66 at each occurrence may include, but are not limited to, P66a, P66 b. Examples of P67 at each occurrence may include, but are not limited to, P67a, P67 b. Examples of P68 at each occurrence may include, but are not limited to, P68a, P68 b. Examples of P69 at each occurrence can include, but are not limited to, P69a, P69 b. Examples of P70 at each occurrence may include, but are not limited to, P70a, P70 b. Examples of P71 at each occurrence can include, but are not limited to, P71a, P71 b. Examples of P72 at each occurrence can include, but are not limited to, P72a, P72 b. Examples of P73 at each occurrence can include, but are not limited to, P73a, P73 b. Examples of P74 at each occurrence may include, but are not limited to, P74a, P74 b. Examples of P81 at each occurrence can include, but are not limited to, P81a, P81 b. Examples of P82 at each occurrence may include, but are not limited to, P82a, P82 b.

The group shown as 1c may be any R described herein⁸Attached to any R described herein⁷Any accessible position of (a).In some embodiments, R⁷Can link 1 or 2R⁸. Examples of groups as shown in 1c may include, but are not limited to, P7 to P14, P24 to P50, P53, P63 to P80, P83 to P92.

In any embodiment, L¹And L²One or two of them may independently represent any one of phenyl, biphenyl, or a group shown as P1 to P92.

In any embodiment, when L¹And L²When none is hydrogen, L¹And L²May each independently represent any of the groups shown as P1 through P92, for example, any of the groups shown as P1 through P82.

In any embodiment, when L¹And L²When one of them is hydrogen, the other may represent any one of the groups shown as P1 to P92, for example, any one of the groups shown as P1, P63 to P92.

In any embodiment, 1 to 4Q¹Represents hydrogen, or 2 to 4Q¹Represents hydrogen, or 3 to 4Q¹Represents hydrogen, or Q¹All represent hydrogen.

In any embodiment, 1 to 4Q²Represents hydrogen, or 2 to 4Q²Represents hydrogen, or 3 to 4Q²Represents hydrogen, or Q²All represent hydrogen.

In some embodiments, Q¹All represent hydrogen and Q²All represent hydrogen.

The compounds of the present invention may include, but are not limited to, the compounds represented by H-1 through H-240.

In some embodiments, the compound is selected from any one of H-7 to H-21, H-25 to H-120, H127 to H-141, H-145 to H-240. Alternatively, the compound may be selected from any one of H-7 to H-21, H-25 to H-60, H101 to H120, H-127 to H-141, H-145 to H-180, H221 to H240. Alternatively, the compound may be selected from any one of H-7 to H-21, H-25 to H-60, H-127 to H-141, H-145 to H-180.

The compounds of the present invention may be prepared 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、Z²And Z³Are respectively and independentlyRepresents halogen. For example, Z¹、Z²And Z³Each independently represents F, Cl, Br or I. L is⁰Is L¹The precursor of (1). For example, L⁰May be L¹-B(OH)₂Or

Other symbols are as defined herein.

By way of example, compounds of some embodiments of the present invention may be prepared according to the following scheme. Other compounds can be prepared as well by reference to these schemes.

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 compound of the present invention may have higher solubility in conventional solvents (such as dichloromethane, chloroform, toluene, dimethylformamide DMF, tetrahydrofuran THF, ethanol, etc.), facilitate the preparation of organic thin film layers, and achieve better film formation 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 fluorescent light emitting materials, phosphorescent light emitting materials, Thermally Activated Delayed Fluorescence (TADF) light emitting materials, and the like, which are well known in the art, depending on the light emitting principle; the light emitting material may be selected from blue light emitting materials, green light emitting materials, red light emitting materials, and the like, which are well known in the art, according to the emission color. The host material known in the art can be selected according to the different luminescent principles and luminescent colors of the guest material; may be a fluorescent host material, a unipolar host material, a bipolar host material, etc., and may be a blue host material, a green host material, a red host material, etc.

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 metal layer, and a cathode comprising a metal oxideA multi-layer cathode formed by combining layers of one or more of a substance 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). For example, a hole blocking layer is laminated between the light emitting layer and the electron transport layer. 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, a hole blocking layer 6, an electron transport layer 7, an electron injection layer 8, a cathode 9, and a cap layer 10, 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 organic light emitting device 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.