Heterocyclic compounds and organic electroluminescent devices and electronic devices

Abstract

The application relates to the technical field of organic electroluminescent materials, and provides a heterocyclic compound, an organic electroluminescent device containing the same and an electronic device. The heterocyclic compound contains a mother nucleus structure of an indole-fused phenothiazine / phenoxazine, and when the compound is used as a host material or a hole adjusting layer of an organic electroluminescent device, the luminous efficiency and the service life of the device can be significantly improved.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic electroluminescent materials, in particular to a heterocyclic compound, an organic electroluminescent device comprising the same and an electronic device. BACKGROUND

[0002] With the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is more and more extensive. An organic electroluminescent device (OLED) generally comprises a cathode and an anode arranged oppositely, and a functional layer arranged between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers, and generally comprises an organic light-emitting layer, a hole transport layer, an electron transport layer, etc. When a voltage is applied to the cathode and the anode, an electric field is generated between the two electrodes, under the action of the electric field, the electrons on the cathode side move to the electroluminescent layer, and the holes on the anode side also move to the electroluminescent layer, the electrons and the holes combine in the electroluminescent layer to form excitons, the excitons in the excited state release energy outward, and then the electroluminescent layer emits light.

[0003] The most important problems in the existing organic electroluminescent device are the service life and the efficiency. With the large-area display, the driving voltage is also increased, and the luminous efficiency and the current efficiency also need to be improved. Therefore, it is necessary to continue to develop new materials to further improve the performance of the organic electroluminescent device. SUMMARY

[0004] In view of the above problems existing in the prior art, the purpose of the present application is to provide a heterocyclic compound, an organic electroluminescent device comprising the same and an electronic device, which is used in an organic electroluminescent device and can improve the performance of the device.

[0005] According to a first aspect of the present application, a heterocyclic compound is provided, the heterocyclic compound has a structure represented by formula 1:

[0006]

[0007] wherein, is connected to any carbon or nitrogen atom in

[0008] X is selected from S or O;

[0009] L, L1 and L2 are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0010] Ar1 and Ar2 are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms.

[0011] Ar is selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, or Ar is a single bond;

[0012] the substituents in L, L1, L2, Ar1, Ar2, and Ar are the same or different, and each is independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triphenylsilyl group, an aryl group having 6 to 20 carbon atoms optionally substituted with 1 or more substituents selected from deuterium, fluorine, and a methyl group, a heteroaryl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, or an arylthio group having 6 to 20 carbon atoms; optionally, any two adjacent substituents in Ar1, Ar2, and Ar form a saturated or unsaturated 3 to 18-membered ring;

[0013] each R1, R2, and R3 is the same or different, and each is independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms, optionally, any two adjacent groups form a benzene ring;

[0014] n1 represents the number of R1, n1 is selected from 0, 1, 2, 3, or 4; n2 represents the number of R2, n2 is selected from 0, 1, 2, or 3; n3 represents the number of R3, n3 is selected from 0, 1, 2, 3, or 4.

[0015] According to a second aspect of the present application, there is provided an organic electroluminescent device, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the heterocyclic compound described above.

[0016] According to a third aspect of the present application, there is provided an electronic device comprising the organic electroluminescent device of the second aspect.

[0017] The structure of the compound of the present application comprises an indolophenothiazine / phenoxazine-arylamines structure, and the two pairs of lone pairs of electrons on the sulfur atom or oxygen atom of the indolophenothiazine / phenoxazine give the parent structure of the compound of the present application excellent hole transport ability. When the parent structure is connected to an arylamine, the hole transport ability can be further enhanced, so that the compound can be suitable for application in different functional layers. When the compound of the present application is used as a host material and a hole adjustment layer, the carrier balance in the light-emitting layer can be improved, the carrier recombination region can be widened, the efficiency of exciton generation and utilization can be improved, and the light-emitting efficiency and the service life of the device can be improved. BRIEF DESCRIPTION OF DRAWINGS

[0018] The accompanying drawings are included to provide a further understanding of the present application, and are incorporated in and constitute a part of this specification, illustrate embodiments of the present application and serve to explain the principles of the present application, but are not intended to limit the present application.

[0019] Figure 1 is a structural schematic diagram of an organic electroluminescent device according to an embodiment of the present application.

[0020] Figure 2 is a structural schematic diagram of an electronic device according to an embodiment of the present application.

[0021] REFERENCE NUMERALS

[0022] 100, anode 200, cathode 300, functional layer 310, hole injection layer

[0023] 321, hole transport layer 322, hole adjustment layer 330, organic light-emitting layer 340, electron transport layer

[0024] 350, electron injection layer 400, electronic device DETAILED DESCRIPTION

[0025] Exemplary embodiments now will be described more fully hereinafter with reference to the accompanying drawings; however, this application should not be construed as limited to the examples set forth herein. Rather, these example embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the application to those skilled in the art. Like reference numerals refer to like elements throughout.

[0026] In a first aspect, the present application provides a heterocyclic compound having a structure represented by formula 1:

[0027]

[0028] wherein, is connected to on any carbon or nitrogen atom;

[0029] X is selected from S or O;

[0030] L, L1and L2are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0031] Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0032] Ar is selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, or Ar is a single bond;

[0033] the substituents in L, L1, L2, Ar1, Ar2and Ar are the same or different, and each is independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triphenylsilyl group, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, or an arylthio group having 6 to 20 carbon atoms; optionally, in Ar1, Ar2and Ar, any two adjacent substituents form a saturated or unsaturated 3 to 18-membered ring;

[0034] each R1, R2and R3is the same or different, and each is independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms, optionally, any two adjacent groups form a benzene ring;

[0035] n1 represents the number of R1, n1 is selected from 0, 1, 2, 3 or 4; n2 represents the number of R2, n2 is selected from 0, 1, 2 or 3; n3 represents the number of R3, n3 is selected from 0, 1, 2, 3 or 4.

[0036] In the present application, the term "optionally" or "optionally" means that the event or circumstance described later can occur or not occur. For example, "optionally, any two adjacent substituents in Ar1, Ar2 and Ar form a saturated or unsaturated 3-18 membered ring" includes a case where any two adjacent substituents form a ring, and a case where any two adjacent substituents each independently exist without forming a ring. "Any two adjacent" can include a case where two substituents are on the same atom, and a case where one substituent is on each of two adjacent atoms. In the case where two substituents are on the same atom, the two substituents can form a saturated or unsaturated spiro ring with the atom to which they are commonly attached. In the case where one substituent is on each of two adjacent atoms, the two substituents can be fused into a ring. For another example, "aryl group having 6 to 20 carbon atoms, optionally substituted by 1 or more substituents selected from the group consisting of deuterium, fluorine, and methyl" includes an unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted aryl group having 6 to 20 carbon atoms, the number of substituents being 1 or more, and the substituents being selected from the group consisting of deuterium, fluorine, and methyl.

[0037] In the present application, the description "each of... is independently" used interchangeably with "each of... is independently" and "each of... is independently" should be interpreted broadly, and can mean that the specific options expressed by the same symbols in different groups do not affect each other, or that the specific options expressed by the same symbols in the same group do not affect each other. For example, wherein each q is independently 0, 1, 2, or 3, and each R" is independently selected from the group consisting of hydrogen, deuterium, fluorine, and chlorine, means that formula Q-1 represents a benzene ring having q substituents R", each of which can be the same or different, and the options for each R" do not affect each other; and formula Q-2 represents a biphenyl in which each benzene ring has q substituents R", the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options for each R" do not affect each other.

[0038] In the present application, the term "substituted or unsubstituted" means that the functional group described after the term can or can not have a substituent (hereinafter, the substituents will be collectively referred to as Rc for convenience of description). For example, "substituted or unsubstituted aryl group" means an aryl group having a substituent Rc or an aryl group without a substituent. The substituents Rc described above can be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a trialkylsilyl group, an alkyl group, a haloalkyl group, a cycloalkyl group, a deuterated phenyl group, or the like. The number of substituents can be 1 or more.

[0039] In the present application, "a plurality of" means 2 or more, for example, 2, 3, 4, 5, 6, and the like.

[0040] In the present application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the number of all carbon atoms.

[0041] The hydrogen atoms in the structures of the compounds of the present application include various isotope atoms of the hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).

[0042] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (such as phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl and a condensed ring aryl connected by carbon-carbon bond conjugation, two or more condensed ring aryl groups connected by carbon-carbon bond conjugation. That is, unless otherwise indicated, two or more aromatic groups connected by carbon-carbon bond conjugation can also be considered as aryl of the present application. Wherein, condensed ring aryl, for example, can include bicyclic condensed aryl (such as naphthyl), tricyclic condensed aryl (such as phenanthrenyl, fluorenyl, anthracenyl) etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se and Si. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, peryl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Ji et al.

[0043] In the present application, the arylene group refers to a divalent group formed by further losing one or more hydrogen atoms from an aryl group.

[0044] In this application, terphenyl includes

[0045] In the present application, the number of carbon atoms in the substituted or unsubstituted aryl (arylene) group may be 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

[0046] In the present application, the fluorenyl group may be substituted by one or more substituents. In the case where the fluorenyl group is substituted, the substituted fluorenyl group may be: etc., but not limited thereto.

[0047] In the present application, aryl as a substituent of L, L1, L2, Ar, Ar1and Ar2is exemplified by, but not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl and the like.

[0048] In the present application, heteroaryl refers to a monovalent aromatic ring or its derivative comprising 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatom can be one or more of B, O, N, P, Si, Se and S. The heteroaryl can be a monocyclic heteroaryl or a polycyclic heteroaryl, in other words, the heteroaryl can be a single aromatic ring system or a plurality of aromatic ring systems connected by a carbon-carbon bond in conjugation, and any of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Exemplarily, the heteroaryl can include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, but is not limited thereto.

[0049] In the present application, the term "heteroaryl" refers to a divalent or polyvalent group formed by further losing one or more hydrogen atoms from the heteroaryl.

[0050] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total number of carbon atoms of 3 to 30, in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total number of carbon atoms of 12 to 18, and in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total number of carbon atoms of 5 to 12.

[0051] In the present application, heteroaryl as a substituent of L, L1, L2, Ar, Ar1and Ar2is exemplified by, but not limited to, pyridyl, carbazolyl, dibenzothienyl, dibenzofuranyl, benzoxazolyl, benzothiazolyl, benzimidazolyl.

[0052] In the present application, the substituted heteroaryl group can be a heteroaryl group in which one or more hydrogen atoms is replaced with a group such as a deuterium atom, a halogen group, -CN, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, a haloalkyl group, or the like.

[0053] In the present application, the alkyl group having 1 to 10 carbon atoms can include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and the like.

[0054] In the present application, the halogen group can be, for example, fluorine, chlorine, bromine, or iodine.

[0055] In the present application, specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0056] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0057] In the present application, the cycloalkyl group having 3 to 10 carbon atoms can have, for example, 3, 4, 5, 6, 7, 8, or 10 carbon atoms. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, and the like.

[0058] In the present application, the deuterated alkyl group having 1 to 10 carbon atoms can have, for example, 1, 2, 3, 4, 5, 6, 7, 8, or 10 carbon atoms. Specific examples of the deuterated alkyl group include, but are not limited to, trideuteromethyl.

[0059] In the present application, the haloalkyl group having 1 to 10 carbon atoms can have, for example, 1, 2, 3, 4, 5, 6, 7, 8, or 10 carbon atoms. Specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0060] In the present application, the ring system formed by n atoms is an n-membered ring. For example, a phenyl group is a 6-membered ring. A 3- to 18-membered ring refers to a cyclic group having 3 to 18 ring atoms. Examples of the 3- to 18-membered ring include cyclopentane, cyclohexane, fluorene, benzene, and the like.

[0061] In the present application, refers to a chemical bond to which other groups are attached.

[0062] In the present application, the unpositioned linking bond refers to a single bond extending from the ring system which indicates that one end of the bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the remainder of the compound molecule. For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is attached to the remainder of the molecule through two indefinite bonds that extend through the bicyclic ring system, and the meaning represented thereby includes any of the possible attachment modes shown in formulae (f-1) to (f-10).

[0063]

[0064] For example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is attached to the remainder of the molecule through one indefinite bond that extends from the middle of one of the phenyl rings, and the meaning represented thereby includes any of the possible attachment modes shown in formulae (X'-1) to (X'-4).

[0065]

[0066] In the present application, an indefinite substituent refers to a substituent that is attached through a single bond extending from the center of a ring system, and indicates that the substituent can be attached to any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is attached to the quinoline ring through an indefinite bond, and the meaning represented thereby includes any of the possible attachment modes shown in formulae (Y-1) to (Y-7).

[0067]

[0068]

[0069] In some embodiments, the compound of formula 1 has a structure represented by formulae 1-1 to 1-4:

[0070]

[0071] In some embodiments, the compound of formula 1 has a structure represented by the following 2-1 to 2-8:

[0072]

[0073] In some embodiments, L, L1, and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms.

[0074] In some embodiments, L, L1and L2are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, or 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0075] Optionally, the substituents in L, L1and L2are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, a deuterium- substituted alkyl group having 1 to 4 carbon atoms, a phenyl group, or a naphthyl group.

[0076] In some embodiments, L, L1and L2are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzofurane group, a substituted or unsubstituted carbazolylene group.

[0077] Optionally, the substituents in L, L1and L2are each independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, t-butyl, trifluoromethyl, trideuteromethyl, a phenyl group, or a naphthyl group.

[0078] In some embodiments, L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted phenanthrylene group.

[0079] Optionally, the substituents in L are each independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, t-butyl, trifluoromethyl, trideuteromethyl, or a phenyl group.

[0080] In some embodiments, L is selected from a single bond or the following groups:

[0081]

[0082] In some embodiments, L1and L2are the same or different, and each is independently selected from a single bond or the following groups:

[0083]

[0084] In some embodiments, Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 18 carbon atoms;

[0085] Ar is selected from a single bond, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 18 carbon atoms.

[0086] In some embodiments, Ar1and Ar2are each independently selected from a substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18 carbon atoms.

[0087] In some embodiments, Ar is selected from a substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18 carbon atoms, or Ar is a single bond. When When attached to Ar, Ar is a single bond, i.e., Formula 1 in this case is

[0088] In some embodiments, the substituents in Ar, Ar1and Ar2are the same or different, and each is independently selected from deuterium, halogen, cyano, haloalkyl having 1 to 4 carbon atoms, deuterated alkyl having 1 to 4 carbon atoms, alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 15 carbon atoms optionally substituted with 1 or more substituents selected from deuterium, fluorine or methyl, heteroaryl having 5 to 12 carbon atoms, trialkylsilyl having 3 to 8 carbon atoms, and optionally, any two adjacent substituents in Ar, Ar1and Ar2form a saturated or unsaturated 5 to 13-membered ring.

[0089] In some embodiments, Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted spirobifluorene group.

[0090] In some embodiments, Ar is selected from a single bond, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthrene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted carbazole, substituted or unsubstituted spirobifluorene, substituted or unsubstituted group:

[0091]

[0092] Optionally, the substituents in Ar, Ar1and Ar2are the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, t-butyl, trifluoromethyl, trideuteromethyl, phenyl, naphthyl, dibenzothiophenyl, dibenzofuranyl, phenanthrenyl, dimethylfluorenyl, pentadeuteriophenyl, carbazolyl, cyclohexyl, cyclopentyl; optionally, in Ar, Ar1and Ar2, any two adjacent substituents form a benzene ring or a fluorene ring

[0093] In some embodiments, Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted group Y; Ar is selected from a substituted or unsubstituted group Y or Ar is a single bond; wherein the unsubstituted group Y is selected from the following groups:

[0094]

[0095] wherein, represents a chemical bond; when the group Y is substituted with one or more substituents, each of the substituents is independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, t-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl, dibenzothiophenyl, dibenzofuranyl, carbazolyl, dimethylfluorenyl, pentadeuteriophenyl or phenanthrenyl.

[0096] In some embodiments, the Ar1and Ar2are the same or different, and each is independently selected from the group consisting of:

[0097]

[0098]

[0099] In some embodiments, Ar is selected from a single bond or the group consisting of:

[0100]

[0101]

[0102] In some embodiments, is selected from the group consisting of:

[0103]

[0104] Optionally, each R1, R2, R3is independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclohexyl, phenyl, or naphthyl; or,

[0105] Optionally, any two adjacent R1form a benzene ring; optionally, any two adjacent R2form a benzene ring; optionally, any two adjacent R3form a benzene ring.

[0106] In some embodiments, the heterocyclic compound is selected from the group consisting of:

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122] In a second aspect, the present application provides an organic electroluminescent device comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the heterocyclic compound of the first aspect of the present application.

[0123] The heterocyclic compound provided by the present application can be used to form at least one organic film layer in the functional layer, so as to improve the luminous efficiency and lifetime of the organic electroluminescent device.

[0124] Optionally, the functional layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises the heterocyclic compound. The organic light-emitting layer can be composed of the heterocyclic compound provided by the present application, or composed of the heterocyclic compound provided by the present application and other materials.

[0125] Optionally, the functional layer further comprises a hole transport layer and a hole adjustment layer, the hole transport layer is located between the anode and the organic light-emitting layer, and the hole adjustment layer is located between the hole transport layer and the organic light-emitting layer. In some embodiments, the hole adjustment layer is composed of the heterocyclic compound provided by the present application, or composed of the heterocyclic compound provided by the present application and other materials.

[0126] According to a specific embodiment, the organic electroluminescent device comprises, as shown in the following figure, an anode 100, a hole injection layer 310, a hole transport layer 321, a hole adjustment layer (also referred to as a hole auxiliary layer) 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350, and a cathode 200, which are sequentially stacked. Figure 1

[0127] In the present application, the anode 100 comprises an anode material, which is preferably a material with large work function that is helpful for hole injection into the functional layer. Specific examples of the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combined metal and oxide such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole, and polyaniline, but not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.

[0128] In the present application, the hole transport layer or the hole adjustment layer can each comprise one or more hole transport materials, and the hole transport material can be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, and can be selected from the following compounds or any combination thereof: ​

[0129]

[0130] In an embodiment, the hole transport layer 321 can be composed of α-NPD.

[0131] In an embodiment, the hole adjustment layer 322 is composed of HT-1.

[0132] In an embodiment of the present application, the hole adjustment layer 322 is composed of the heterocyclic compound of the present application.

[0133] Optionally, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to enhance the ability of injecting holes into the hole transport layer 321. The hole injection layer 310 can be selected from diphenylamine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in the present application. The material of the hole injection layer 310 can be selected from the following compounds or any combination thereof, for example:

[0134]

[0135]

[0136] In an embodiment of the present application, the hole injection layer 310 is composed of PD.

[0137] Optionally, the organic light-emitting layer 330 can be composed of a single light-emitting material, or can include a host material and a guest material. Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material, the holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine to form excitons in the organic light-emitting layer 330, the excitons transfer energy to the host material, the host material transfers energy to the guest material, and then the guest material emits light.

[0138] The host material of the organic light-emitting layer 330 can include metal chelate compounds, bisstyryl derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials. The host material of the organic light-emitting layer 330 can be a compound, a combination of two or more compounds. Optionally, the host material includes the heterocyclic compound of the present application.

[0139] The guest material of the organic light-emitting layer 330 can be a compound or derivative thereof having condensed aryl rings, a compound or derivative thereof having heteroaryl rings, aromatic amine derivatives or other materials, which are not particularly limited in the present application. The guest material is also known as a doping material or dopant. According to the type of light emission, it can be divided into fluorescent dopants and phosphorescent dopants. For example, specific examples of the phosphorescent dopant include, but are not limited to,

[0140] In one embodiment of the present application, the organic electroluminescent device is a red organic electroluminescent device. In a more particular embodiment, the host material of the organic light-emitting layer 330 comprises the heterocyclic compound of the present application. The guest material can be, for example, Ir(Mphq)3.

[0141] In another embodiment, the organic electroluminescent device is a green organic electroluminescent device. In a more particular embodiment, the host material of the organic light-emitting layer 330 comprises the heterocyclic compound of the present application. The guest material can be, for example, fac-Ir(ppy)3.

[0142] The electron transport layer 340 can be a single layer structure or a multi-layer structure, which can comprise one or more electron transport materials selected from, but not limited to, ET-1, BmPyPhB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, which are not particularly limited in the present application. The material of the electron transport layer 340 comprises, but is not limited to, the following compounds:

[0143]

[0144] In one embodiment of the present application, the electron transport layer 340 can be composed of BmPyPhB and LiQ, or composed of ET-1 and LiQ.

[0145] In the present application, the cathode 200 comprises a cathode material, which is a material with small work function that helps to inject electrons into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multi-layer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al and BaF2 / Ca. Alternatively, a metal electrode comprising magnesium and silver is included as the cathode.

[0146] Alternatively, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 can comprise inorganic materials such as alkali metal sulfides, alkali metal halides, etc., or can comprise complexes of alkali metals with organic substances. In one embodiment of the present application, the electron injection layer 350 comprises ytterbium (Yb).

[0147] The third aspect of the present application provides an electronic device comprising the organic electroluminescent device of the second aspect of the present application.

[0148] According to one embodiment, as Figure 2As shown, the provided electronic device is electronic device 400, which comprises the organic electroluminescent device described above. The electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, for example, but not limited to, a computer screen, a cell phone screen, a television, an electronic paper, an emergency lighting, an optical module, etc.

[0149] The synthesis of the heterocyclic compounds of the present application will be described in detail below in connection with the synthesis examples, but the present disclosure is not limited thereto.

[0150] Synthesis Examples

[0151] It will be recognized by those skilled in the art that the chemical reactions described herein can be used to prepare a number of the heterocyclic compounds of the application, and that other methods for preparing the compounds of the application are also within the scope of the present application. For example, the synthesis of those compounds of the application which are not exemplified herein can be successfully performed by a skilled artisan by applying the methods described herein to the synthesis of the known compounds using appropriate reagents, according to the procedures described herein, or by making routine modifications to such procedures. The compounds of the present application for which no synthetic methods are described in the present application are commercially available starting materials.

[0152] Synthesis of Sub-a1:

[0153]

[0154] Into a 250 mL three-necked flask, M1 (CAS: 3377-71-7, 10.36 g, 50 mmol), 2- chlorocyclohexanone (6.60 g, 50 mmol), anhydrous sodium carbonate (6.36 g, 60 mmol) and 2,2,2-trifluoroacetic acid (75 mL) were added under nitrogen atmosphere. The reaction was stirred at room temperature for 48 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain Sub-a1 (11.68 g, yield 77%) as a white solid.

[0155] Referring to the synthesis of Sub-a1, Sub-a2 to Sub-a4 were synthesized by using the reactant A shown in Table 1 instead of M1.

[0156] Table 1: Synthesis of Sub-a2 to Sub-a4

[0157]

[0158] Synthesis of Sub-b1:

[0159]

[0160] Sub-b1 (8.49 g, yield 42%) was obtained as a white solid. Sub-b2 to Sub-b7 were synthesized according to the procedure described for Sub-b1 by using the reactants B shown in Table 2 instead of Sub-a1 and the reactants C instead of 2-aminobenzenethiol.

[0161] Sub-b1 (8.49 g, yield 42%) was obtained as a white solid. Sub-b2 to Sub-b7 were synthesized according to the procedure described for Sub-b1 by using the reactants B shown in Table 2 instead of Sub-a1 and the reactants C instead of 2-aminobenzenethiol.

[0162] Table 2: Synthesis of Sub-b2 to Sub-b7

[0163]

[0164]

[0165] Synthesis of Sub-c1:

[0166]

[0167] Sub-b1 (8.49 g, yield 42%) was obtained as a white solid. Sub-b2 to Sub-b7 were synthesized according to the procedure described for Sub-b1 by using the reactants B shown in Table 2 instead of Sub-a1 and the reactants C instead of 2-aminobenzenethiol.

[0168] Sub-b1 (8.49 g, yield 42%) was obtained as a white solid. Sub-b2 to Sub-b7 were synthesized according to the procedure described for Sub-b1 by using the reactants B shown in Table 2 instead of Sub-a1 and the reactants C instead of 2-aminobenzenethiol.

[0169] Table 3: Synthesis of Sub-c2 to Sub-c7

[0170]

[0171]

[0172] Synthesis of Sub-d1

[0173]

[0174] Sub-c1 (20.11 g, 50 mmol), potassium tert-butoxide (56.10 g, 500 mmol) and DMSO (300 mL) were sequentially added into a 500 mL three-necked flask under nitrogen atmosphere, and then stirring and heating were started. The temperature was raised to 50-60 °C and the reaction was carried out for 4 h. After the system was cooled to room temperature, the reaction solution was poured into 500 mL deionized water, and a precipitate was separated out. The filter cake was collected by suction filtration, and then the filter cake was dissolved in 200 mL dichloromethane and dried over anhydrous sodium sulfate. After filtration, the solvent was removed from the filtrate by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain white solid compound Sub-d1 (13.11 g, yield 84%).

[0175] Referring to the synthesis of Sub-d1, Sub-d2 to Sub-d7 were synthesized by using the reactants E shown in Table 4 instead of Sub-c1.

[0176] Table 4: Synthesis of Sub-d2 to Sub-d7

[0177]

[0178] Synthesis of Sub-e1

[0179]

[0180] Sub-d1 (15.62 g, 50 mmol), m-chlorobromobenzene (10.53 g, 55 mmol), tris(dibenzylideneacetone)dipalladium (0.916 g, 1 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.95 g, 2 mmol), sodium tert-butoxide (t-BuONa, 9.61 g, 100 mmol) and toluene (160 mmol) were sequentially added into a 250 mL three-necked flask under nitrogen atmosphere, and then the temperature was raised to reflux and the reaction was carried out overnight with stirring. After the system was cooled to room temperature, the reaction solution was poured into 500 mL deionized water, and then stirred for 30 min. The filter cake was collected by suction filtration, and then washed with deionized water until neutral and then washed with 200 mL anhydrous ethanol. The filter cake was collected to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain white solid Sub-e1 (16.70 g, yield 79%).

[0181] Referring to the synthesis of Sub-e1, Sub-e2 to Sub-e13 were synthesized by using the reactants F shown in Table 5 instead of Sub-d1 and the reactant G instead of m-chlorobromobenzene.

[0182] Table 5: Synthesis of Sub-e2 to Sub-e13

[0183]

[0184]

[0185] Synthesis of Sub-f1 :

[0186]

[0187] Into a 500 mL three-necked flask, Sub-e5 (21.10 g, 50 mmol), 3-chlorobenzeneboronic acid (8.58 g, 55 mmol), palladium acetate (0.22 g, 1.0 mmol), 2-dicyclohexylphosphino-2',4',6' triisopropyl biphenyl (0.95 g, 2 mmol), anhydrous potassium carbonate (13.82 g, 100 mmol), toluene (220 mL), tetrahydrofuran (55 mL) and deionized water (55 mL) were added successively under nitrogen atmosphere. The stirring and heating were started and the temperature was raised to reflux. The reaction was continued for 16 h. After the system was cooled to room temperature, dichloromethane (100 mL x 3) was used to extract the product. The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure to give a crude product. Silica gel column chromatography was used to purify the crude product with n-heptane as the mobile phase. Sub-f1 (15.47 g, yield 62%) was obtained as a white solid.

[0188] Referring to the synthesis of Sub-f1, Sub-e5 was replaced by reactant H and 3-chlorobenzeneboronic acid was replaced by reactant J in Table 6 to synthesize Sub-f2 to Sub-f10.

[0189] Table 6: Synthesis of Sub-f2 to Sub-f10

[0190]

[0191]

[0192] Synthesis of compound 6:

[0193]

[0194] Into a 250 mL three-necked flask, Sub-e1 (10.57 g, 25 mmol), RA-1 (8.12 g, 27.5 mmol), tris(dibenzylideneacetone)dipalladium (0.46 g, 0.5 mmol), 2-biscyclohexylphosphino-2',6'-dimethoxybiphenyl (0.41 g, 1 mmol), sodium tert-butoxide (4.80 g, 50 mmol) and xylene (100 mmol) were added successively under nitrogen atmosphere. The reaction was heated to reflux and stirred overnight. After the system was cooled to room temperature, the reaction was poured into 250 mL of deionized water, stirred thoroughly for 30 min, suction filtered, and the filter cake was washed with deionized water until neutral, then washed with absolute ethanol (100 mL). The filter cake was collected to give the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to give compound 6 as a white solid (10.91 g, 64% yield). Mass: m / z = 682.2 [M+H] + .

[0195] Referring to the synthesis of compound 6, using reactant K shown in Table 7 to replace Sub-e1, and reactant L to replace raw material RA-1, the compounds of the application in Table 7 were synthesized.

[0196] Table 7

[0197]

[0198]

[0199]

[0200]

[0201]

[0202] NMR of compound 13: 1 H-NMR (400 MHz, CD2Cl2) δ ppm 7.94 (d, 1H), 7.90-7.82 (m, 3H), 7.77 (d, 1H), 7.74 (d, 1H), 7.56-7.44 (m, 8H), 7.42-7.33 (m, 6H), 7.30-7.24 (m, 3H), 7.18 (d, 1H), 7.06 (t, 1H), 6.96-6.88 (m, 5H), 6.79 (d, 1H), 6.76 (d, 2H), 6.49 (d, 2H);

[0203] NMR of compound 105: 1H-NMR(400MHz,CD2Cl2)δppm 8.01-7.96(m,2H),7.87(d,1H),7.58(t,2H),7.54-7.49(m,3H),7.48-7.32(m,9H),7.30-7.22(m,3H),7.1 8(d,1H),7.07(d,1H),7.04(s,1H),7.02(s,1H),6.94(t,1H),6.79(d,1H),6.68-6.60(m,4H),6.38(d,1H).

[0204] Preparation and evaluation of organic electroluminescent devices:

[0205] Example 1: Preparation of red organic electroluminescent device

[0206] First, the anode pretreatment is carried out through the following process: On the ITO / Ag / ITO substrate, the surface treatment was performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode, and the surface of the ITO substrate was cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0207] PD was vacuum-deposited on the experimental substrate (anode) to form a Then, α-NPD was vacuum-deposited on the hole injection layer to form a hole injection layer with a thickness of hole transport layer.

[0208] Compound HT-1 is vacuum-deposited on the hole transport layer to form a layer with a thickness of Hole Adjustment Layer.

[0209] Next, RH-N: compound 6: Ir(Mphq)3 were co-deposited on the hole adjustment layer at a deposition rate ratio of 49%:49%:2% to form a layer with a thickness of A red organic light-emitting layer (EML) is provided.

[0210] On the organic light-emitting layer, the compound BmPyPhB and LiQ were mixed in a weight ratio of 1:1 and evaporated to form Yb is evaporated on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a 1:9 evaporation rate and vacuum evaporated on the electron injection layer to form a layer with a thickness of cathode.

[0211] In addition, the thickness of the vacuum evaporation layer on the cathode is CP-1, thereby completing the fabrication of a red organic electroluminescent device.

[0212] Examples 2 to 27

[0213] An organic electroluminescent device was prepared by the same method as in Example 1, except that the compound shown in Table 8 below was used instead of Compound 6 in Example 1 when preparing the organic light-emitting layer.

[0214] Comparative Examples 1 to 3

[0215] An organic electroluminescent device was prepared using the same method as in Example 1, except that Compound A, Compound B, and Compound C were used to replace Compound 6 in Example 1 when preparing the organic light-emitting layer.

[0216] In the preparation of Examples 1 to 27 and Comparative Examples 1 to 3, the compound structures used are as follows:

[0217]

[0218] The performance of the red organic electroluminescent devices prepared in Examples 1 to 27 and Comparative Examples 1 to 3 was tested. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of T95 device life at 20mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 8.

[0219] Table 8

[0220]

[0221]

[0222] As can be seen from Table 8 above, when the compound of the present invention is used as the host material of a red organic electroluminescent device, the device efficiency is increased by at least 16.4%, and the T95 lifespan is increased by at least 16.9%.

[0223] Example 28: Red organic electroluminescent device

[0224] First, the anode pretreatment is carried out through the following process: On the ITO / Ag / ITO substrate, the surface treatment was performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode, and the surface of the ITO substrate was cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0225] PD was vacuum-deposited on the experimental substrate (anode) to form a Then, α-NPD was vacuum-deposited on the hole injection layer to form a hole injection layer with a thickness of hole transport layer.

[0226] Compound 90 is vacuum evaporated on the hole transport layer to form a layer with a thickness of Hole Adjustment Layer.

[0227] Next, RH-N:PR-P:Ir(Mphq)3 was co-deposited on the hole adjustment layer at a deposition rate ratio of 49%:49%:2% to form a layer with a thickness of red light emitting layer (EML).

[0228] On the light-emitting layer, the compound BmPyPhB and LiQ were mixed in a weight ratio of 1:1 and evaporated to form Yb is evaporated on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a 1:9 evaporation rate and vacuum-deposited on the electron injection layer to form a layer with a thickness of cathode.

[0229] In addition, CP-1 is vacuum-deposited on the cathode to form a layer with a thickness of The covering layer is formed, thereby completing the manufacture of the red organic electroluminescent device.

[0230] Examples 28 to 41

[0231] An organic electroluminescent device was prepared by the same method as in Example 28, except that the compound shown in Table 9 below was used instead of Compound 90 in Example 28 when preparing the hole adjustment layer.

[0232] Comparative Examples 4-5

[0233] An organic electroluminescent device was prepared by the same method as in Example 26, except that Compound D and Compound E were used instead of Compound 90 in Example 28 when preparing the hole adjustment layer.

[0234] Among them, when preparing each of Examples 28 to 41 and Comparative Examples 4 to 5, the main compound structures used are as follows:

[0235]

[0236] The green organic electroluminescent devices prepared in Examples 28 to 41 and Comparative Examples 4 to 5 were tested for their performance. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of T95 device life at 20mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 9.

[0237] Table 9

[0238]

[0239] As can be seen from Table 9, when the compound of the present application is used as a hole adjusting layer of a red organic electroluminescent device, the efficiency of the device is increased by at least 16.9%, and the T95 lifetime is increased by at least 18.5%.

[0240] The compound of the present application comprises an indolophenothiazine / phenoxazine- arylamine structure in the structure of the compound. The two pairs of lone pair electrons on the sulfur atom or oxygen atom of the indolophenothiazine / phenoxazine endow the parent structure of the compound of the present application with excellent hole transport capacity. When the parent structure is connected with arylamine, the hole transport capacity can be further adjusted, so that the compound can be suitable for application in different functional layers. When the compound of the present application is used as a host material and a hole adjusting layer, the carrier balance in the light-emitting layer can be improved, the carrier recombination region can be widened, the efficiency of exciton generation and utilization can be improved, and the luminous efficiency and lifetime of the device can be improved.

[0241] The preferred embodiments of the present application are described in detail above with reference to the drawings, but the present application is not limited to the specific details of the above-described embodiments. Within the technical concept of the present application, various simple modifications can be made to the technical solutions of the present application, and these simple modifications all belong to the protection scope of the present application.

Claims

1. A heterocyclic compound, characterized in that The heterocyclic compound has a structure shown in Formula 1: in, Connect to On any carbon or nitrogen atom; X is selected from S or O; L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolylene group; The substituents in L, L1 and L2 are each independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl or naphthyl; Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted group Y; Ar is selected from a substituted or unsubstituted group Y or Ar is a single bond; wherein the unsubstituted group Y is selected from the following groups: in, represents a chemical bond; when the group Y is substituted by one or more substituents, the substituents are each independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl, dibenzothienyl, dibenzofuranyl, carbazolyl, dimethylfluorenyl, pentadeuterophenyl or phenanthrenyl; each R1, R2 and R3 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclohexyl, phenyl or naphthyl; or, optionally, any two adjacent R1s form a benzene ring, optionally, any two adjacent R2s form a benzene ring, optionally, any two adjacent R3s form a benzene ring; n1 represents the number of R1, n1 is selected from 0, 1, 2, 3 or 4; n2 represents the number of R2, n2 is selected from 0, 1, 2 or 3; n3 represents the number of R3, n3 is selected from 0, 1, 2, 3 or 4.

2. The heterocyclic compound according to claim 1, wherein The compound represented by Formula 1 has the structures represented by Formulas 1-1 to 1-4:

3. The heterocyclic compound according to claim 1, wherein L is selected from a single bond or the following groups:

4. The heterocyclic compound according to claim 3, wherein L1 and L2 are the same or different and are each independently selected from the group consisting of a single bond or the following groups:

5. The heterocyclic compound according to claim 1, wherein Ar1 and Ar2 are the same or different and are each independently selected from the group consisting of: The heterocyclic compound according to claim 5, wherein Ar is a single bond or a group consisting of:

7. Heterocyclic compounds, wherein The heterocyclic compound is selected from the group consisting of the following compounds:

8. An organic electroluminescent device comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; characterized in that: The functional layer comprises an organic light-emitting layer, wherein the organic light-emitting layer comprises the heterocyclic compound according to any one of claims 1 to 7; and / or The functional layer includes a hole adjustment layer, and the hole adjustment layer comprises the heterocyclic compound according to any one of claims 1 to 7.

9. An electronic device, characterized in that The organic electroluminescent device according to claim 8 is included.

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