Organic heterocyclic compound, display panel and display device

Abstract

The present application provides an organic heterocyclic compound, a display panel and a display device. The organic heterocyclic compound has a structure as shown in Formula I below, wherein R<supgt;1< / supgt>, R<supgt;2< / supgt>, R<supgt;3< / supgt>, R<supgt;4< / supgt>, R<supgt;5< / supgt> and Ar are as defined herein. The organic heterocyclic compound can improve the luminous efficiency and service life of an organic electroluminescent device and can reduce the driving voltage.

Description

Technical Field

[0001] The present application relates to the field of organic light-emitting technologies, and particularly relates to an organic heterocyclic compound, a display panel, and a display device. Background Art

[0002] As a new generation of display technology, an organic light-emitting device (OLED) has the advantages of being ultrathin, self-luminous, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, and low energy consumption, and has been widely used in industries such as flat panel display, flexible display, solid-state lighting, and vehicle-mounted display.

[0003] An OLED includes a cathode, an anode, and an organic thin film layer. Among them, the organic thin film layer contains a light-emitting material. The cathode and the anode inject electrons and holes into the organic thin film layer respectively. The electrons and holes combine within the light-emitting material to generate electron-hole pairs, that is, excitons. When the excitons return from the excited state to the stable ground state, they can release energy in the form of light, thereby emitting visible light. According to the light-emitting mechanism, it can be divided into two types: electrofluorescence and electrophosphorescence. Fluorescence is the radiative decay transition of singlet excitons, and phosphorescence is the light emitted when triplet excitons decay radiatively to the ground state.

[0004] Currently, osmium complexes and platinum complexes are used as dyes doped into the light-emitting layer, and the prepared phosphorescent materials are applied to electro-luminescent devices. The internal quantum efficiency and external quantum efficiency of the phosphorescent materials are much higher than those of fluorescent materials. However, the currently used phosphorescent light-emitting materials have problems of insufficient long life and low efficiency. Summary of the Invention

[0005] The present application provides an organic heterocyclic compound, a display panel, and a display device. The organic heterocyclic compound can improve the luminous efficiency and service life of an organic light-emitting device, and can reduce the driving voltage.

[0006] In a first aspect, an embodiment of the present application provides an organic heterocyclic compound having a structure shown in Formula I as follows:

[0007]

[0008] Wherein, R 1 is selected from a group represented by -NR a R b , -L a -N-R c R d or -L b -R e R f represents a group,

[0009] R a 、Rb Each independently selected from optionally substituted or unsubstituted 6- to 30-membered aryl, optionally substituted or unsubstituted 5- to 30-membered heteroaryl, arylalkyl containing 6 to 36 carbon atoms, heteroarylalkyl containing 2 to 35 carbon atoms. Optionally, R a , R b are connected to form a ring;

[0010] L a 、L b are each independently selected from optionally substituted or unsubstituted 6- to 30-membered arylene, optionally substituted or unsubstituted 5- to 30-membered heteroarylene;

[0011] R c 、R d are each independently selected from optionally substituted or unsubstituted 6- to 30-membered aryl, optionally substituted or unsubstituted 5- to 30-membered heteroaryl, arylalkyl containing 6 to 36 carbon atoms, heteroarylalkyl containing 2 to 35 carbon atoms. Optionally, R c 、R d are connected to form a ring;

[0012] R e 、R f are each independently selected from hydrogen, optionally substituted or unsubstituted 6- to 30-membered aryl, optionally substituted or unsubstituted 5- to 30-membered heteroaryl, arylalkyl containing 6 to 36 carbon atoms, heteroarylalkyl containing 2 to 35 carbon atoms. Optionally, R c 、R d are connected to form a ring;

[0013] R 2 、R 3 and R 4 each independently represent hydrogen, optionally substituted or unsubstituted 6- to 30-membered aryl;

[0014] The hydrogen on the C at the a1 and a2 positions is unsubstituted or substituted with Ar, and Ar has the structure shown in Formula II, where # respectively represents the connection sites to the C at the a1 and a2 positions;

[0015]

[0016] R 5 represents hydrogen, optionally substituted or unsubstituted 6- to 30-membered aryl.

[0017] According to an embodiment of one aspect of the present application, the organic heterocyclic compound has a structure shown in any one of Formula III, Formula IV, and Formula V:

[0018]

[0019] According to an embodiment of one aspect of the present application, the organic heterocyclic compound has the structure shown in Formula IIIa:

[0020]

[0021] R 1 C connected to any one of d1, d2, d3, and d4;

[0022] R 1 、R 2 、R 3 and R 4 are as defined above.

[0023] According to an embodiment of one aspect of the present application, the organic heterocyclic compound has the structure shown in Formula IVa or Formula Va:

[0024]

[0025] In Formula IVa or Formula Va, R 1 are each independently C connected to any one of d1, d2, d3, and d4;

[0026] R 1 、R 2 、R 3 、R 4 and R 5 are as defined above.

[0027] According to an embodiment of one aspect of the present application, R 1 is selected from the group represented by R 1 selected from -NR a R b 、-L a -N-R c R d or -L b -R e R f ;

[0028] R a 、R b 、R c 、R d 、R e 、R f are independently selected from optionally substituted or unsubstituted 6- to 12-membered aryl groups, optionally substituted or unsubstituted 5- to 11-membered heteroaryl groups, arylalkyl groups containing 6 to 36 carbon atoms, and heteroarylalkyl groups containing 2 to 35 carbon atoms; R c 、R d are connected to form a ring;

[0029] Among them, the arylalkyl group containing 6 to 36 carbon atoms is selected from arylalkyl groups containing 6 to 36 carbon atoms; the heteroarylalkyl group containing 2 to 35 carbon atoms is selected from heteroarylalkyl groups containing 2 to 35 carbon atoms.

[0030] According to an embodiment of one aspect of the present application, R 1 is a group represented by -NR a R b , and R a and R b are each independently selected from an optionally substituted or unsubstituted 6- to 30-membered aryl group, an arylalkyl group containing 6 to 36 carbon atoms, and R a , R b are connected to form a ring.

[0031] According to an embodiment of one aspect of the present application, R 1 is a group represented by -L a -N-R c R d or -L b -R e R f ,

[0032] L a , L b is selected from any one of the following: phenylene, biphenylene, terphenylenylene, quaterphenylenylene, p-phenylenediaminophenylene, naphthylene, phenanthrylene, anthrylene, trinaphthylene, pyrenylene, ylene, fluorenylene, anthroneylene, fluoranthenylene, spirobifluorenylene;

[0033] R c , R d , R e , R f are independently selected from an optionally substituted or unsubstituted 6- to 30-membered aryl group, an arylalkyl group containing 6 to 36 carbon atoms, and R c , R d are connected to form a ring.

[0034] According to an embodiment of one aspect of the present application, R 2 , R 3 , R 4 and R 5 each include a group represented by -NR a R b ,

[0035] R a , R b are selected from an optionally substituted or unsubstituted 6- to 30-membered aryl group, an arylalkyl group containing 6 to 36 carbon atoms. Optionally, R a , R b are connected to form a ring;

[0036] According to an embodiment of one aspect of the present application, R 1 , R 2 , R 3 , R 4 and R 5 at least one of them includes a group represented by -NR a R b .

[0037] R a , R b are selected from optionally substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, arylalkyl groups having 6 to 36 carbon atoms.

[0038] According to an embodiment of one aspect of the present application, R 5 is selected from any one of the following groups: phenyl, biphenyl, terphenyl, quaterphenyl, p-diphenylaminophenyl, naphthyl, phenanthryl, anthryl, triphenylene, pyrenyl, -yl, fluorenyl, anthroneyl, fluoranthenyl, spirobifluorenyl.

[0039] According to an embodiment of one aspect of the present application, the organic heterocyclic compound is selected from any one of the following H01 to H88:

[0040]

[0041]

[0042]

[0043]

[0044] In a second aspect, an embodiment of the present application provides a display panel, including an organic electroluminescent device. The organic electroluminescent device includes an anode, a cathode, and an organic thin film layer located between the anode and the cathode. The organic thin film layer includes a light-emitting layer, and the light-emitting layer includes one or more of the organic heterocyclic compounds of the first aspect.

[0045] According to an embodiment of one aspect of the present application, the organic thin film layer further includes an electron transport region and / or a hole transport region, wherein the electron transport region and the hole transport region include one or more of the organic heterocyclic compounds of the first aspect.

[0046] In a third aspect, an embodiment of the present application provides a display device, including the display panel of the second aspect.

[0047] For the display panel and the display device provided by the present application, due to the inclusion of the above-mentioned organic heterocyclic compound, therefore, the display panel and the display device of the present application have a lower driving voltage, a higher luminous efficiency, and a longer service life.

[0048] The above description is only an overview of the technical solution of the present application. In order to better understand the technical means of the present application, it can be implemented according to the content of the specification. In order to make the above and other purposes, features, and advantages of the present application more obvious and understandable, specific embodiments of the present application are hereinafter given. Description of the Drawings

[0049] In order to more clearly illustrate the technical solutions of the embodiments of the present application, the drawings required for use in the embodiments of the present application will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present application. For those of ordinary skill in the art, other drawings can be obtained according to the drawings without creative efforts.

[0050] Figure 1 It is a schematic structural diagram of an organic electroluminescent device provided in some embodiments of the present application.

[0051] Figure 2 It is a schematic diagram of a display device provided in some embodiments of the present application.

[0052] Description of the Reference Numerals:

[0053] Substrate 1, Anode 2, First Hole Transport Layer 3, Second Hole Transport Layer 4, Electron Blocking Layer 5, Light Emitting Layer 6, First Electron Transport Layer 7, Second Electron Transport Layer 8, Cathode 9, Covering Layer 10;

[0054] Mobile phone 100. Detailed Embodiments

[0055] In order to make the inventive purpose, technical solution, and beneficial technical effects of the present application clearer, the present application will be further described in detail below in conjunction with embodiments. It should be understood that the embodiments described in this specification are only for explaining the present application and not for limiting the present application.

[0056] The above inventive content of the present application does not intend to describe every disclosed embodiment or every implementation mode of the present application. The following description more specifically gives examples of exemplary embodiments. Throughout the application, guidance is provided through a series of embodiments, which can be used in various combinations. In each instance, the enumeration is only as a representative group and should not be construed as exhaustive.

[0057] In the description herein, unless otherwise specified, "above" and "below" include the number itself, and the meanings of "one or more" and "one or more" in "multiple" and "multiple" are more than two (pieces).

[0058] The terms "a" and "the" each refer to one or more molecules of the compound, and are not limited to a single molecule of the compound. In addition, the one or more molecules may be the same or may be different, so long as they fall within the scope of the chemical compound.

[0059] The term "comprising" and variations thereof as used in the specification and claims is not limiting.

[0060] The terms "preferred" and "preferably" refer to embodiments of the present application that in certain circumstances may provide certain benefits. However, in the same or other circumstances, other embodiments may also be preferred. In addition, 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 present disclosure.

[0061] The grouping of alternative elements or embodiments disclosed herein should not be construed as limiting. Each member of the group 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, for reasons of convenience and / or patentability, one or more members of the group may be included in or deleted from the group. When any such inclusion or deletion occurs, the specification is hereby regarded as containing the modified group, and thus meets the written description of all Markush groups used in the claims.

[0062] Unless otherwise indicated, when a compound or chemical structure feature (e.g., aryl) is referred to as "substituted", the feature may have one or more substituents. The term "substituent" has the broadest meaning known to those of ordinary skill in the art and includes such moieties that occupy positions normally occupied by one or more hydrogen atoms attached to the parent compound or chemical structure feature. In some embodiments, the substituent may be a common organic moiety known in the art, which may have a molecular weight of 15 - 50 g / mol, 15 - 100 g / mol, 15 - 200 g / mol, or 15 - 500 g / mol (e.g., the sum of the atomic masses of the atoms of the substituent). Some substituents include F, Cl, Br, I, NO2, C 1-12 H 3-25 、C 1- 12 H 1-25 O、C 1-12 H 1-25 O2、C 1-12 H 3-26 N、C 1-12 H 1-26 NO、C 1-12 H 3-27 N2、C 1-12 F3-25 A substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted C3-C10 heteroaryl group, etc.

[0063] The term "aryl (ring)" refers to a closed aromatic ring or ring system. Examples of aryl (ring) include, but are not limited to, phenyl (ring), naphthyl (ring), fluorenyl (ring), indenyl (ring), anthracenyl (ring), phenanthryl (ring), pyrenyl (ring), spirobifluorenyl (ring), and similar aryl (rings). In various embodiments, the 6-40 membered aryl (ring), i.e., the aryl (ring), may contain 6-40 carbon atoms for forming the ring.

[0064] The term "heteroaryl" means that one or more atoms in the ring of the aryl group are elements other than carbon. In some embodiments, as a whole, the C5-C30 heteroaryl may contain 5-25, 5-18, or 6-12 ring heteroatoms (such as N, O, P, S, halogen atoms, etc.). Examples of heteroaryl include, but are not limited to, pyrrolyl, furyl, oxazolyl, isoxazolyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, oxadiazolyl, imidazolyl, pyrazolyl, triazole, pyridazinyl, pyrazinyl, pyridyl, pyrimidinyl, triazinyl, indolyl, quinolinyl, isoquinolinyl, acridinyl, purinyl, pteridinyl, benzofuryl, benzothienyl, benzimidazolyl, benzothiazolyl, benzotriazolyl, benzoxadiazolyl, benzoxazolyl, cinnoline, quinoxalinyl, dibenzofuryl, dibenzothienyl, carbazolyl, phenanthrolinyl, indazinyl, naphthyridinyl, and phthalazinyl. In various embodiments, the C5-C30 heteroaryl, i.e., the heteroaryl, may contain 5-30 carbon atoms for forming the ring.

[0065] The term "alkyl" includes not only straight-chain or branched-chain saturated hydrocarbon groups, such as methyl, ethyl, propyl (such as n-propyl, isopropyl), butyl (such as n-butyl, isobutyl, sec-butyl, tert-butyl), pentyl (such as n-pentyl, isopentyl, neopentyl), and similar alkyl groups, but also alkyl substituents with other substituents known in the art, such as hydroxyl, alkylsulfonyl, halogen atoms, cyano, nitro, amino, carboxyl, etc. Therefore, "alkyl" includes ether groups, haloalkyls, nitroalkyls, carboxyalkyls, hydroxyalkyls, sulfoalkyls, etc. In various embodiments, the C1-C20 alkyl, i.e., the alkyl, may contain 1-20 carbon atoms.

[0066] The term "alkoxy" means -O-alkyl. Examples of alkoxy include, but are not limited to, methoxy, ethoxy, propoxy (such as n-propoxy, isopropoxy), butoxy (such as n-butoxy, isobutoxy, sec-butoxy, tert-butoxy), and similar alkoxy groups.

[0067] The term "cycloalkyl" refers to a non-aromatic carbocyclic group, including cyclized alkyl, alkenyl, and alkynyl groups. A cycloalkyl group can be monocyclic (such as cyclohexyl) or polycyclic (such as fused rings, bridged rings, and / or spiro rings). Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, and cyclohexenyl. In various embodiments, a 3- to 20-membered cycloalkyl group, i.e., a cycloalkyl group, may contain 3 to 20 carbon atoms for forming the ring.

[0068] The term "halo" or "halogen" refers to fluorine, chlorine, bromine, and iodine, such as fluorine.

[0069] The term "hydrogen" refers to 1 H (protium, H), 2 H (deuterium, D), or 3 H (tritium, T). In various embodiments, "hydrogen" may be 1 H (protium, H).

[0070] Throughout this specification, substituents of compounds are disclosed in groups or ranges. It is expressly contemplated that such descriptions include every individual sub-combination of the members of these combined ranges. For example, it is expressly contemplated that the term "C1-C6 alkyl" discloses 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 alkyls individually. As other examples, it is expressly contemplated that integers in the range of 5 to 40 disclose 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 individually; and it is expressly contemplated that integers in the range of 1 to 20 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.

[0071] In this document, the representation of a single bond passing through a ring or a ring system means that the single bond can be connected to any accessible position of the ring or the ring system.

[0072] Organic heterocyclic compounds

[0073] In a first aspect, an embodiment of the present application provides an organic heterocyclic compound having a structure represented by the following formula I:

[0074]

[0075] Wherein, R 1Selected from -NR a R b 、-L a -N-R c R d or -L b -R e R f a group represented by;

[0076] R a 、R b are each independently selected from an optionally substituted or unsubstituted 6- to 30-membered aryl group, an optionally substituted or unsubstituted 5- to 30-membered heteroaryl group, an arylhydrocarbyl group containing 6 to 36 carbon atoms, a heteroarylhydrocarbyl group containing 2 to 35 carbon atoms. Optionally, R a 、R b are connected to form a ring;

[0077] L a 、L b are selected from an optionally substituted or unsubstituted 6- to 30-membered arylene group, an optionally substituted or unsubstituted 5- to 30-membered heteroarylene group;

[0078] R c 、R d are each independently selected from an optionally substituted or unsubstituted 6- to 30-membered aryl group, an optionally substituted or unsubstituted 5- to 30-membered heteroaryl group, an arylhydrocarbyl group containing 6 to 36 carbon atoms, a heteroarylhydrocarbyl group containing 2 to 35 carbon atoms. Optionally, R c 、R d are connected to form a ring;

[0079] R e 、R f are independently selected from hydrogen, an optionally substituted or unsubstituted 6- to 30-membered aryl group, an optionally substituted or unsubstituted 5- to 30-membered heteroaryl group, an arylhydrocarbyl group containing 6 to 36 carbon atoms, a heteroarylhydrocarbyl group containing 2 to 35 carbon atoms. Optionally, R c 、R d are connected to form a ring;

[0080] R 2 、R 3 and R 4 each independently represent hydrogen, an optionally substituted or unsubstituted 6- to 30-membered aryl group;

[0081] The hydrogen on the C at the a1 and a2 positions is unsubstituted or substituted by Ar, and Ar has the structure shown in Formula II, where # respectively represents the connection sites to the C at the a1 and a2 positions;

[0082]

[0083] R 5represents hydrogen, an optionally substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0084] According to the technical solution of the embodiment of the present application, the sulfur-nitrogen heterocyclic structure of the above-mentioned organic heterocyclic compound is used as the central skeleton, which has an electron-donating ability, and a group with an electron-withdrawing ability is connected to the skeleton, so that the compound has a bipolar structure, which is conducive to the transmission and recombination of electrons and holes, thereby improving the luminous efficiency of the device having it.

[0085] At the same time, this structure can reduce the molecular force, reduce the intermolecular stacking, which is conducive to reducing concentration quenching and efficiency roll-off, and enables the device to have a long service life.

[0086] In addition, the organic heterocyclic compound of the present application can also reduce the driving voltage of the device.

[0087] The organic heterocyclic compound of the present application has good thermal stability and film-forming properties. The organic heterocyclic compound of the present application also has an appropriate glass transition temperature Tg, which is conducive to forming a stable and uniform thin film during the thermal vacuum evaporation process, while reducing phase separation and maintaining the stability of the device. It has a high carrier transport rate and balanced carrier transport performance, so as to facilitate the balance of hole and electron transport in the device and obtain a wider carrier recombination region, thereby improving the luminous efficiency. The organic heterocyclic compound of the present application has a suitable glass transition temperature Tg and thermal decomposition temperature, which can help improve the stability after film formation, thus reducing the influence of Joule heat generated during the operation of the organic electroluminescent device on the luminous efficiency and service life, and suppressing the reduction of electron transport performance and exciton formation efficiency caused by crystallization.

[0088] In addition, the organic heterocyclic compound of the present application has a high solubility in conventional solvents (such as dichloromethane, chloroform, toluene, dimethylformamide, tetrahydrofuran, ethanol, etc.), which is convenient for the preparation of the organic thin film layer, and obtains good film-forming uniformity, reducing or avoiding the appearance of holes.

[0089] In some embodiments of the present application, the organic heterocyclic compound has a structure shown in any one of the following formulas III, IV, and V:

[0090]

[0091] In some embodiments of the present application, the organic heterocyclic compound has a structure shown in formula IIIa:

[0092]

[0093] R 1 C connected to any one of d1, d2, d3, and d4;

[0094] R1 , R 2 , R 3 and R 4 are defined as above.

[0095] In some embodiments of the present application, the organic heterocyclic compound has the structure shown in Formula IVa or Formula Va:

[0096]

[0097] In Formula IVa or Formula Va, R 1 is independently connected to C at any one of d1, d2, d3, and d4;

[0098] R 1 , R 2 , R 3 , R 4 and R 5 are defined as above.

[0099] In some embodiments of the present application, R 1 is selected from R 1 is selected from -NR a R b , -L a -N-R c R d or -L b -R e R f represents a group,

[0100] R a , R b , R c , R d , R e , R f are independently selected from optionally substituted or unsubstituted 6- to 12-membered aryl groups, optionally substituted or unsubstituted 5- to 11-membered heteroaryl groups, arylalkyl groups containing 6 to 36 carbon atoms, and heteroarylalkyl groups containing 2 to 35 carbon atoms; R c , R d are connected to form a ring;

[0101] Among them, the arylalkyl groups containing 6 to 36 carbon atoms are selected from arylalkyl groups containing 6-36 carbon atoms; the heteroarylalkyl groups containing 2 to 35 carbon atoms are selected from heteroarylalkyl groups containing 2-35 carbon atoms.

[0102] In some embodiments of the present application, R 1 is a group represented by -NR a R b represents a group, R a and R bIndependently selected from optionally substituted or unsubstituted aryl groups having 6 to 30 carbon atoms or arylalkyl groups having 6 to 36 carbon atoms, R a and R b are connected to form a ring.

[0103] In some embodiments of the present application, R 1 is a group represented by -L a -N-R c R d or -L b -R e R f wherein

[0104] L a and L b are each independently selected from any one of the following: phenylene, biphenylene, terphenylenylene, quaterphenylenylene, p-phenylenediaminophenylene, naphthylene, phenanthrylene, anthrylene, triphenylene, pyrenylene, -yl, fluorenylene, anthroneylene, fluoranthenylene, spirobifluorenylene;

[0105] R c and R d and R e and R f are independently selected from optionally substituted or unsubstituted aryl groups having 6 to 30 carbon atoms or arylalkyl groups having 6 to 36 carbon atoms, and R c and R d are connected to form a ring.

[0106] In some embodiments of the present application, R 2 and R 3 and R 4 and R 5 each include a group represented by -NR a R b wherein

[0107] R a and R b are each independently selected from optionally substituted or unsubstituted aryl groups having 6 to 30 carbon atoms or arylalkyl groups having 6 to 36 carbon atoms, and optionally, R a and R b are connected to form a ring;

[0108] According to an embodiment of one aspect of the present application, at least one of R 1 and R 2 and R 3 and R 4 and R 5 includes a group represented by -NR a R b wherein

[0109] R a and Rb Independently selected from optionally substituted or unsubstituted aryl groups having 6 to 30 carbon atoms or arylalkyl groups having 6 to 36 carbon atoms.

[0110] In some embodiments of the present application, R 5 Selected from any of the following groups: phenyl, biphenyl, terphenyl, quaterphenyl, p-diphenylaminophenyl, naphthyl, phenanthryl, anthryl, triphenylene, pyrenyl, fluorenyl, anthrone, fluoranthene, spirobifluorenyl.

[0111] In some embodiments of the present application, the organic heterocyclic compound is selected from any one of the following H01 to H88:

[0112]

[0113]

[0114]

[0115]

[0116] display panel

[0117] In a second aspect, embodiments of the present application provide a display panel, including an organic electroluminescent device, the organic electroluminescent device including an anode, a cathode, and an organic thin film layer located between the anode and the cathode, the organic thin film layer including a light-emitting layer, and the light-emitting layer including one or more of the organic heterocyclic compounds of the first aspect.

[0118] In the embodiments of the present application, the organic electroluminescent device may be a bottom-emitting organic electroluminescent device, a top-emitting organic electroluminescent device, or a stacked organic electroluminescent device, and no specific limitation is imposed thereon.

[0119] In the organic electroluminescent device of the present application, the substrate used may be any substrate well known to those skilled in the art, such as a transparent substrate, an opaque substrate, or a flexible substrate. Exemplarily, the transparent substrate may be a transparent glass or a transparent plastic substrate, the opaque substrate may be a silicon substrate, and the flexible substrate may be a flexible polyimide film substrate.

[0120] In the embodiments of the present application, the anode may be made of a conductor, and the conductor has a relatively high work function to facilitate the injection of holes. Exemplarily, the conductor may be a metal, a metal oxide, and / or a conductive polymer.

[0121] In some embodiments of the present application, the anode can be made of a metal, such as nickel, platinum, vanadium, chromium, copper, zinc, gold, silver, or an alloy thereof. The anode can also be made of a metal oxide, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO). In addition to the above, a combination of a metal and a metal oxide can also be used to make the anode, such as ZnO and Al, or SnO2 and Sb, or ITO and Ag.

[0122] In some other embodiments of the present application, the anode can be made of a conductive polymer, such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline.

[0123] In embodiments of the present application, the cathode can also be made of a conductor having a low work function to facilitate electron injection. Exemplarily, the cathode can be made of magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, LiF / Al, Li2O / Al, LiF / Ca, BaF2 / Ca, and combinations thereof.

[0124] In embodiments of the present application, the light-emitting layer is disposed between the anode and the cathode and can include at least one host material and at least one guest material. Both the host material and the guest material in the light-emitting layer include one or more of the organic heterocyclic compounds in any of the above embodiments.

[0125] In some embodiments of the present application, the organic thin film layer further includes an electron transport region and / or a hole transport region, wherein the electron transport region and the hole transport region include one or more of the organic heterocyclic compounds in the first aspect.

[0126] In embodiments of the present application, the electron transport region refers to the region where electrons move between the cathode and the light-emitting layer. Exemplarily, the electron transport region can include at least one layer of an electron injection layer, an electron transport layer, and a hole blocking layer, and one or more of the organic heterocyclic compounds in any of the above embodiments are included in at least one layer.

[0127] Exemplarily, the electron transport region includes a first electron transport layer and a second electron transport layer stacked, and the materials of the first electron transport layer and the second electron transport layer include one or more of the organic heterocyclic compounds in any of the above embodiments.

[0128] The hole transport region refers to the region where holes move between the anode and the light-emitting layer. Exemplarily, the hole transport region can include at least one layer of a hole injection layer, a hole transport layer, and an electron blocking layer, and one or more of the organic heterocyclic compounds in any of the above embodiments are included in at least one layer.

[0129] Exemplarily, the hole transport region includes a first hole transport layer, a second hole transport layer, and an electron blocking layer which are stacked, and the materials of the first hole transport layer, the second hole transport layer, and the electron blocking layer include one or more of the organic heterocyclic compounds in any of the above embodiments.

[0130] Figure 1 An organic electroluminescent device is shown as an example, which includes a substrate 1, an anode 2, a first hole transport layer 3, a second hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a first electron transport layer 7, a second electron transport layer 8, a cathode 9, and a cover layer 10 which are stacked in sequence. Figure 1 The arrow in represents the light emitting direction of the device.

[0131] In the embodiments of the present application, an organic electroluminescent device can be fabricated by methods known in the art. Exemplarily, the fabrication method of the organic electroluminescent device can include: forming an anode on a transparent or opaque substrate, forming an organic thin film layer on the anode, and forming a cathode on the organic thin film layer. Among them, the formation of the organic thin film layer can adopt known film forming methods such as evaporation, sputtering, spin coating, dipping, ion plating, etc.

[0132] Display device

[0133] In a third aspect, an embodiment of the present application provides a display device, including the display panel of the second aspect.

[0134] In some embodiments of the present application, the display device can be but is not limited to a smart phone 100 (as Figure 2 shown), a smart watch, a tablet computer, a notebook computer, a PC, a TV, or a display device for a vehicle, a VR, an AR helmet, or a lighting device, etc., and the present application does not make specific limitations thereto.

[0135] The following embodiments more specifically describe the content disclosed in the present application. These embodiments are only for illustrative purposes, because various modifications and changes within the scope of the content disclosed in the present application are obvious to those skilled in the art. Unless otherwise stated, all parts, percentages, and ratios reported in the following embodiments are based on weight, and all reagents used in the embodiments are commercially available or can be synthesized according to conventional methods and can be used directly without further treatment, and the instruments used in the embodiments are all commercially available.

[0136] Synthesis of organic heterocyclic compounds

[0137] The present application exemplarily provides several preparation methods of organic heterocyclic compounds. Other compounds of the present application can be prepared with reference to this exemplary method. According to the exemplary compound preparation method, those skilled in the art can easily obtain the specific methods for implementing each synthesis step from relevant scientific literature or standard textbooks in the art. Unless otherwise specified, commercially available or compounds known in the literature are used as raw materials for synthesis. Those skilled in the art of organic synthesis will recognize that, for the purpose of optimizing the generation of the compounds described herein, the nature and order of the proposed synthesis steps can be changed.

[0138] The processes described herein can be monitored according to any suitable method known in the art. For example, product formation can be monitored by spectroscopic means such as nuclear magnetic resonance spectroscopy (NMR, e.g., 1H or 13C), 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).

[0139] Example 1

[0140] (1) Under a nitrogen atmosphere, add the reaction solvent 1,2-dichlorobenzene to a reaction flask, and successively add the reaction intermediate a1 (2.1 mmol), the reactant b1 (2.2 mmol), potassium carbonate (7 mmol), the catalyst CuI (0.5 mmol) and the ligand 18-crown-6 (0.5 mmol). Heat to 100 °C and react for 24 h. After the reaction is completed, cool to room temperature, filter by suction to collect the organic phase, extract with dichloromethane / H2O, dry the collected organic phase with anhydrous Na2SO4, filter by suction to collect the filtrate, remove the solvent by rotary evaporation and purify by column chromatography to obtain the intermediate c1. As follows:

[0141]

[0142] MALDI-TOF (m / z): C25H15N3OS, calculated value: 405.09, measured value: 405.15.

[0143] Compound elemental analysis results: calculated value: C, 74.05; H, 3.73; N, 10.36; O, 3.95; S, 7.91; measured value: C, 74.05; H, 3.74; N, 10.35; O, 3.95; S, 7.91.

[0144]

[0145] (2) In a three-necked flask, add intermediate d1 (50 mmol) and dry tetrahydrofuran (120 mL) successively. Cool to -70 °C under nitrogen protection, and slowly add 3.0 M n-butyllithium (20 mL). After the addition, react for 1 hour, then add a 70 mL tetrahydrofuran solution containing compound c1 (55 mmol). After the addition, slowly warm to room temperature and react for 3 h. Extract with dichloromethane and concentrate. Add acetic acid (120 mL) and concentrated hydrochloric acid (3 mL), heat under reflux for 8 h, cool, remove the solvent, wash the crude product with dichloromethane solvent and water, dry and concentrate the organic layer, and purify the crude product by column chromatography to obtain compound H17.

[0146] The compound obtained above was analyzed by matrix-assisted laser desorption ionization time-of-flight mass spectrometry MALDI-TOFMS (m / z), and the measurement was: C49H30N4S, calculated value: 706.22, measured value: 706.25.

[0147] The compound obtained above was analyzed for its elemental composition, and the results were as follows: calculated values: C, 83.26; H, 4.28; N, 7.93; S, 4.54; measured values: C, 83.25; H, 4.29; N, 7.93; S, 4.54.

[0148] Examples 2 to 8

[0149] The organic heterocyclic compounds of Examples 2 to 8 were synthesized by a method similar to that of Example 1, and the specific raw materials or intermediates used are shown in Table 1.

[0150] Comparative Example 1

[0151] Compound M1, the structural formula is:

[0152]

[0153] Table 1

[0154]

[0155]

[0156]

[0157] The following application examples provide exemplary embodiments for illustrating the practical application of the organic heterocyclic compounds of the present application in OLED devices.

[0158] Application Example 1

[0159] This application example provides an OLED device, which includes a substrate 1, an ITO anode 2, a first hole transport layer 3, a second hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a first electron transport layer 7, a second electron transport layer 8, a cathode 9, and a capping layer 10 that are stacked in sequence.

[0160] The preparation method of the OLED device is as follows:

[0161] 1) Cut the glass substrate 1 into a size of 50 mm × 50 mm × 0.7 mm, ultrasonically treat it in isopropyl alcohol and deionized water for 30 min respectively, and then expose it to ozone for about 10 min for cleaning; mount the obtained glass substrate with the ITO anode 2 on a vacuum deposition device;

[0162] 2) On the ITO anode 2, deposit the hole buffer layer material HT-1∶HAT-CN by vacuum evaporation. The mass ratio of the compound HT-1 to HAT-CN is 98:2 to obtain a layer with a thickness of 10 nm, and this layer serves as the first hole transport layer 3;

[0163] 3) Vacuum deposit the material HT-1 of the second hole transport layer 4 on the first hole transport layer 3 to obtain a layer with a thickness of 95 nm, and this layer serves as the second hole transport layer 4;

[0164] 4) Deposit the material Prime-1 on the second hole transport layer 4 to obtain a layer with a thickness of 30 nm, and this layer serves as the electron blocking layer 5;

[0165] 5) Co-deposit the light-emitting layer 6 on the electron blocking layer 5. Among them, use the organic compound H17 provided in Example 1 of this application as the host material and Ir(piq)2(acac) as the doping material. The mass ratio of the organic compound H01 to Ir(piq)2(acac) is 19:1, and the thickness is 30 nm;

[0166] 6) Vacuum deposit the compound ET-1 of the first electron transport layer 7 on the light-emitting layer 6 to obtain the first electron transport layer 7 with a thickness of 30 nm;

[0167] 7) Vacuum deposit the material LiF of the second electron transport layer 8 on the first electron transport layer 7 to obtain the second electron transport layer 8 with a thickness of 5 nm;

[0168] 8) Vacuum deposit magnesium silver on the second electron transport layer 8 to prepare a cathode 9 with a thickness of 15 nm, where the mass ratio of Mg:Ag is 9:1;

[0169] 9) Vacuum deposit a high-refractive-index hole-type material CPL-1 on the cathode 9 with a thickness of 100 nm for use as the cathode capping layer 10.

[0170] The structural formulas of the materials HAT-CN, HT-1, Prime-1, Ir(piq)2(acac), ET-1, and CPL-1 mentioned in the above steps are shown as follows:

[0171]

[0172] Application Example 2

[0173] The difference between this application example and Application Example 1 is only that the organic compound H17 in step (5) is replaced with an equal amount of the organic compound H18 provided in Example 2 of the present application; other preparation steps are the same.

[0174] Application Example 3

[0175] The difference between this application example and Application Example 1 is only that the organic compound H17 in step (5) is replaced with an equal amount of the organic compound H19 provided in Example 3 of the present application; other preparation steps are the same.

[0176] Application Example 4

[0177] The difference between this application example and Application Example 1 is only that the organic compound H17 in step (5) is replaced with an equal amount of the organic compound H20 provided in Example 4 of the present application; other preparation steps are the same.

[0178] Application Example 5

[0179] The difference between this application example and Application Example 1 is only that the organic compound H17 in step (5) is replaced with an equal amount of the organic compound H65 provided in Example 5 of the present application; other preparation steps are the same.

[0180] Application Example 6

[0181] The difference between this application example and Application Example 1 is only that the organic compound H17 in step (5) is replaced with an equal amount of the organic compound H66 provided in Example 6 of the present application; other preparation steps are the same.

[0182] Application Example 7

[0183] The difference between this application example and Application Example 1 is only that the organic compound H17 in step (5) is replaced with an equal amount of the organic compound H67 provided in Example 7 of the present application; other preparation steps are the same.

[0184] Application Example 8

[0185] The difference between this application example and Application Example 1 is only that the organic compound H17 in step (5) is replaced with an equal amount of the organic compound H68 provided in Example 8 of the present application; other preparation steps are the same.

[0186] ]>Application Comparative Example 1

[0187] The difference between this comparative example and Application Example 1 is only that the organic compound H17 in step (5) is replaced with an equal amount of comparative compound M1 (shown below); other preparation steps are the same.

[0188]

[0189] Performance Detection of OLED Devices

[0190] Use a Keithley 2365A digital nanovoltmeter to measure the current of the OLED device at different voltages, and then divide the current by the luminous area to obtain the current density of the OLED device at different voltages; use a Konica Minolta CS-2000 spectroradiance luminance meter to measure the luminance and radiant energy flux density of the OLED device at different voltages; according to the current density and luminance of the OLED device at different voltages, obtain the turn-on voltage and current efficiency (CE, Cd / A) at the same current density (10 mA / cm 2 ), V on is the turn-on voltage at a luminance of 1 Cd / m 2 ; the lifetime LT95 (under the test conditions of 50 mA / cm 2 ) is obtained by measuring the time when the luminance of the OLED device reaches 95% of the initial luminance; the specific data are shown in Table 2.

[0191] Table 2

[0192]

[0193] From the data in Table 2, it can be seen that compared with the device in Comparative Example 1, the organic heterocyclic compounds provided in Examples 1-8 of the present application can make the OLED device have higher current efficiency, which is about 6.7% - 7.5% higher than that in Comparative Example 1 (as the current efficiency in Table 1 above is the relative current efficiency obtained with the current efficiency of the device in Comparative Example 1 as 100%). Moreover, the organic heterocyclic compounds provided in the present application can also make the OLED device have a longer service life, which is extended by about 7.3% - 9.2% compared with the service life of the device in Comparative Example 1 (as LT95 in Table 1 above is the relative LT95 obtained with the LT95 of the device in Comparative Example 1 as 100%).

[0194] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present application, rather than to limit them; although the present application has been described in detail with reference to the foregoing embodiments, those of ordinary skill in the art should understand that they can still modify the technical solutions described in the foregoing embodiments, or perform equivalent replacements for some or all of the technical features; and these modifications or replacements do not cause the essence of the corresponding technical solutions to deviate from the scope of the technical solutions of the various embodiments of the present application, and they should all be covered within the scope of the claims and the description of the present application. In particular, as long as there is no structural conflict, the technical features mentioned in each embodiment can be combined in any way. The present application is not limited to the specific embodiments disclosed in the text, but includes all technical solutions falling within the scope of the claims.

Claims

1. An organic heterocyclic compound, characterized in that, The organic heterocyclic compound is selected from any one of the following H17 to H24 and H65 to H72:

2. A display panel, comprising an organic electroluminescent device, the organic electroluminescent device including an anode, a cathode, and an organic thin film layer located between the anode and the cathode, the organic thin film layer including a light-emitting layer, and the light-emitting layer including one or more of the organic heterocyclic compounds described in claim 1.

3. The display panel according to claim 2, characterized in that, The organic thin film layer further includes an electron transport region and / or a hole transport region, wherein the electron transport region and the hole transport region include one or more of the organic heterocyclic compounds described in claim 1.

4. A display device, comprising the display panel described in claim 2 or 3.

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