Organic compound for luminescent device, application of organic compound and organic electroluminescent device

Abstract

The invention provides a multi-heteroaryl substituted fused ring compound which is characterized in that the compound is of a structure shown in a formula (1), a group A represents an aromatic group containing a dibenzo five-membered heterocyclic ring, and when the compound is applied to an organic electroluminescent device, the voltage and efficiency of the device can be effectively improved. The invention further provides an organic light-emitting device and a display device.

Description

Technical Field

[0001] The invention relates to an organic compound, belonging to the technical field of organic luminescent materials, and also relates to the application of the compound and an organic electroluminescent device containing the compound. Background Art

[0002] In recent years, optoelectronic devices based on organic materials have developed rapidly and become a research hotspot in the field. Examples of organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic photovoltaic cells, organic sensors, etc. Among them, OLED has developed particularly rapidly and has achieved commercial success in the field of information display. OLED can provide highly saturated red, green, and blue colors. Full-color display devices made of OLED do not require additional backlight sources and have the advantages of bright colors, lightness, thinness, and softness.

[0003] The core of OLED devices is a multilayer thin film structure containing a variety of functionalized organic materials. Common functionalized organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, luminescent host materials and luminescent guest materials (dyes), etc. When power is turned on, electrons and holes are injected and transported to the luminescent area respectively and recombine there, thereby generating excitons and emitting light.

[0004] According to the luminescence mechanism, the current OLED can be divided into fluorescent luminescence, phosphorescent luminescence, thermally excited delayed fluorescence and thermally excited sensitized fluorescence. Common fluorescent luminescent bodies mainly use singlet excitons generated when electrons and holes combine to emit light, and are still widely used in various OLED products. Some metal complexes (such as iridium complexes and platinum complexes) can simultaneously use triplet excitons and singlet excitons for luminescence, and are called phosphorescent luminescent bodies. Their energy conversion efficiency can be increased by up to four times that of traditional fluorescent luminescent bodies. Thermally excited delayed fluorescence (TADF) promotes the transformation of triplet excitons to singlet excitons. Without the use of metal complexes, triplet excitons can still be effectively utilized to achieve higher luminescence efficiency. Thermally excited sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize the luminescent body through energy transfer, which can also achieve higher luminescence efficiency.

[0005] Although products using OLED technology have been commercialized, the voltage, lifespan, efficiency and other performance of the device still need to be continuously improved to meet people's pursuit of high-quality display effects. Therefore, the field is in urgent need of developing more types of higher-performance organic materials, which can be applied to organic electroluminescent devices to make the devices have better luminous effects. Summary of the invention

[0006] In view of the shortcomings of the prior art, one of the purposes of the present invention is to provide a polyheteroaryl-substituted fused ring compound with benzoxazole as a parent core and triazine and dibenzo five-membered heterocyclic ring as substituents, which has good photoelectric properties when applied to OLED devices. Specifically, the first aspect of the present invention provides a compound, specifically a polyheteroaryl-substituted fused ring compound, characterized in that it is a structure shown in formula (1):

[0007]

[0008] In formula (1), Y is O, S; Z is O, S or NR 5 , R 5 One selected from substituted or unsubstituted C1-C20 straight or branched alkyl, C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0009] Group A is a group of formula (a-1);

[0010] Ar 1 ,Ar 2 is one of a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C3-C60 heteroaryl group;

[0011] L 1 , L 2 , L 3 , L 4 Each independently represents a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C6-C60 fused ring arylene group, a substituted or unsubstituted C3-C60 heteroarylene group, or a substituted or unsubstituted C3-C60 fused ring heteroarylene group; Ar is a C6-C24 aryl group. It should be noted that the meaning of aryl means that Ar does not contain a heteroatom;

[0012] R 1 , R 2 , R 3 represents one or more substituents, each independently selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl, when R 1 and R 2 When there are multiple R, they can be connected to each other to form a ring, or fused with adjacent benzene rings to form a ring. 3When there are multiple rings, they may form a ring with each other or be fused with adjacent benzene rings to form a ring.

[0013] The substitution in the above “substituted or unsubstituted” refers to substitution by any one or a combination of at least two selected from halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl, each independently selected from the group consisting of:

[0014] “*” indicates the connection site, and “—” crosses the ring structure, indicating that the connection site is at any position on the ring structure that can form a bond.

[0015] In the mother core structure of the present invention, the introduction of a dibenzo five-membered heterocycle (furan, thiophene, etc.) in benzoxazole deepens the LUMO energy level of the material, which is more conducive to the transmission of electrons, and its operating voltage is further reduced. After containing heteroatom substituents such as dibenzofuran or thiophene, the S1 state of such groups belongs to the n,π* type, and the n-π* transition is a spin-forbidden transition. The corresponding fluorescence intensity is very weak or does not fluoresce. Therefore, it has a higher energy transfer efficiency in the phosphorescent system, and the efficiency is improved. The inventors also found that the triazine group and the oxazole group have a synergistic effect and show higher efficiency.

[0016] It should be noted that, unless otherwise defined below, the meanings of all technical terms and scientific terms used herein are intended to be the same as those generally understood by those skilled in the art. Reference to the technology used herein is intended to refer to the technology generally understood in the art, including those changes in technology or replacement of equivalent technology that are obvious to those skilled in the art. Although it is believed that the following terms are well understood by those skilled in the art, the following definitions are still set forth to better explain the present invention.

[0017] In this specification, the expression of Ca to Cb represents that the number of carbon atoms in the group is a to b. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms in the substituent. When describing C1 to 30, it includes but is not limited to C1, C2, C3, C4, C3, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C22, C24, C26, C28, etc., and other numerical ranges are not repeated.

[0018] The terms "comprises," "comprising," "having," "containing," or "involving" and other variations thereof herein are inclusive or open-ended and do not exclude additional unrecited elements or method steps.

[0019] In the present invention, the expression of chemical elements, unless otherwise specified, generally includes the concept of isotopes with the same chemical properties. For example, the expression "hydrogen" also includes the concepts of "deuterium" and "tritium" with the same chemical properties, and carbon (C) includes 12 C. 13 C, etc., no further details.

[0020] The heteroatom in the present invention is generally selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

[0021] As used herein, the terms "heterocyclyl" and "heterocycle" refer to a saturated (i.e., heterocycloalkyl) or partially unsaturated (i.e., having one or more double and / or triple bonds within the ring) cyclic group having at least one ring atom that is a heteroatom selected from N, O and S and the remaining ring atoms being C.

[0022] As used herein, the terms "(ylidene)aryl" and "aromatic ring" refer to an all-carbon monocyclic or fused-ring polycyclic aromatic group having a conjugated π electron system. As used herein, the terms "(ylidene)heteroaryl" and "heteroaromatic ring" refer to a monocyclic, bicyclic or tricyclic aromatic ring system. As used herein, the term "aralkyl" preferably refers to an alkyl substituted with an aryl or heteroaryl group, wherein the aryl, heteroaryl and alkyl groups are as defined herein.

[0023] As used herein, the term "halo" or "halogen" group is defined to include F, Cl, Br, or I.

[0024] The term "substituted" means that one or more (e.g., one, two, three, or four) hydrogens on the designated atom are replaced by a selection from the indicated group, provided that the normal valence of the designated atom in the present context is not exceeded and the substitution forms a stable compound. Combinations of substituents and / or variables are permitted only if such combinations form stable compounds.

[0025] If substituents are described as being "independently selected" from a group, each substituent is selected independently of the other. Thus, each substituent may be the same as or different from another (other) substituent.

[0026] As used herein, the term "one or more" means 1 or more than 1, such as 2, 3, 4, 5 or 10, where reasonable.

[0027] Unless otherwise indicated, as used herein, the point of attachment of a substituent may be from any suitable position of the substituent.

[0028] When a bond to a substituent is shown to pass through a bond connecting two atoms in a ring, then such substituent may be bonded to any ring atom in the substitutable ring.

[0029] The term "about" means within ±10% of the stated numerical value, preferably within ±5%, more preferably within ±2%.

[0030] In the structural formula disclosed in this specification, the expression of “—” crossing over a ring structure indicates that the connection site is at any position on the ring structure that can form a bond.

[0031] The above-mentioned C6-C60 aromatic ring and C3-C60 heteroaromatic ring in the present invention, unless otherwise specified, are aromatic groups satisfying the π conjugated system, including both monocyclic residues and condensed ring residues. The so-called monocyclic residue refers to a molecule containing at least one phenyl group. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, such as phenyl, biphenyl, terphenyl, etc.; a fused ring residue refers to a molecule containing at least two benzene rings, but the benzene rings are not independent of each other, but are fused to each other by sharing the ring edge, such as naphthyl, anthracenyl, phenanthryl, etc.; a monocyclic heteroaryl refers to a molecule containing at least one heteroaryl group. When the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and connected by a single bond, such as pyridine, furan, thiophene, etc.; a fused heteroaryl refers to a molecule composed of at least one phenyl group and at least one heteroaryl group fused together, or composed of at least two heteroaryl rings fused together, such as quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, etc.

[0032] In the present specification, the substituted or unsubstituted C6-C60 aromatic ring is preferably a C6-C30 aromatic ring, and more preferably an aromatic ring in the group consisting of phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrene, chrysene, peryl, fluoranthene, naphthyl, pentacene, benzopyrene, biphenyl, isophenyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, and spiroisotrimerized indenyl. Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetraphenyl group is selected from 1-tetraphenyl, 2-tetraphenyl and 9-tetraphenyl. Preferred examples of the aromatic ring in the present invention include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives, fluoranthenyl, triphenylene, pyrenyl, peryl, The biphenyl group is selected from the group consisting of 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl. The fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9,9-dimethylfluorene, 9,9-spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the naphthyl group is selected from the group consisting of 1-naphthyl, 2-naphthyl and 9-naphthyl.

[0033] In the present specification, the substituted or unsubstituted C6-C60 aromatic group is preferably a C6-C30 aromatic group, and more preferably a group selected from the group consisting of phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrene, chrysene, peryl, fluoranthene, naphthyl, pentacene, benzopyrene, biphenyl, isophenyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, and spiroisotrimerized indenyl. Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetraphenyl group is selected from 1-tetraphenyl, 2-tetraphenyl and 9-tetraphenyl. Preferred examples of the aryl group in the present invention include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives, fluoranthenyl, triphenylene, pyrenyl, peryl, The biphenyl group is selected from the group consisting of 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl. The fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9,9-dimethylfluorene, 9,9-spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the naphthyl group is selected from the group consisting of 1-naphthyl, 2-naphthyl and 9-naphthyl. The C6-C60 aryl group of the present invention can also be a group formed by combining the above groups by single bond connection or / and fusion.

[0034] In the present specification, the substituted or unsubstituted C3-C60 heteroaromatic ring is preferably a C3-C30 heteroaromatic ring, which can be a nitrogen-containing heteroaromatic group, an oxygen-containing heteroaromatic group, a sulfur-containing heteroaromatic group, etc. Specific examples include: furyl, thienyl, pyrrolyl, pyridyl, benzofuranyl, benzothienyl, isobenzofuranyl, isobenzothienyl, indolyl, isoindolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and its derivatives, quinolyl, isoquinolyl, acridinyl, phenanthridinyl , benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1, 1,2,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazolyl, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purinyl, pteridinyl, indolizine, benzothiadiazole and the like. Preferred examples of heteroaromatic rings in the present invention include heteroaromatic rings of furyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazolebenzocarbazole, dibenzocarbazole or indolecarbazole.

[0035] In the present specification, the substituted or unsubstituted C3-C60 heteroaryl group is preferably a C3-C30 heteroaryl group, more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, etc. Specific examples include: furyl, thienyl, pyrrolyl, pyridyl, benzofuranyl, benzothienyl, isobenzofuranyl, isobenzothienyl, indolyl, isoindolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and its derivatives, quinolyl, isoquinolyl, acridinyl, phenanthridine yl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidazinyl, pyridinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazolyl, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purinyl, pteridinyl, indolizine, benzothiadiazole and the like. Preferred examples of heteroaryl groups in the present invention include furanyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazolebenzocarbazole, dibenzocarbazole or indolecarbazole. The C3-C60 heteroaryl group of the present invention may also be a group formed by combining the above groups by single bond connection or / and fusion.

[0036] In the present invention, the aryl ether group and heteroaryl ether group include groups formed by the above-mentioned aryl group and heteroaryl group and oxygen. In the present invention, the aryl amino group and heteroaryl amino group include groups formed by replacing one or two H in the -NH2 group with the above-mentioned aryl group and heteroaryl group.

[0037] In this specification, the chain alkyl group includes both straight-chain and branched alkyl groups. Examples of the C1-C20 alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl neohexyl, n-heptyl, n-octyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, and 2,2,2-trifluoroethyl.

[0038] In the present specification, the C3-C20 cycloalkyl group includes a monocyclic alkyl group and a polycyclic alkyl group, and specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl and the like.

[0039] The number of carbon atoms of the C2-C20 straight-chain or cyclic alkenyl group is preferably 2 to 10. Specific examples include vinyl, 1-propenyl, 2-propenyl, 2-butenyl, 3-butenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 5-hexenyl, 7-octenyl, and groups in which these groups have substituents such as alkyl and alkoxy groups.

[0040] The number of carbon atoms in the C2-C20 straight-chain or cyclic alkynyl group is preferably 2 to 10. Specific examples of the alkynyl group include ethynyl, 1-propynyl, 2-propynyl, 2-butynyl, 3-butynyl, 3-pentynyl, 4-pentynyl, 1-hexynyl, 5-hexynyl, and groups in which these groups have substituents such as alkyl and alkoxy groups.

[0041] In the present specification, an alkoxy group refers to a group consisting of the above-mentioned chain alkyl group and oxygen, or a group consisting of the above-mentioned cycloalkyl group and oxygen.

[0042] Examples of C1-C20 alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like, among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy and isopentyloxy are preferred, and methoxy is more preferred.

[0043] In the present specification, examples of C1-C20 silyl groups include silyl groups substituted with the groups listed above for the C1-C20 alkyl groups, i.e., groups formed by replacing one, two or three hydrogen atoms on the silyl group with the above-mentioned chain alkyl or cycloalkyl groups. Specifically, groups include methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl and the like.

[0044] As a preferred embodiment of the present invention, in formula (1), L3 and L 4 The substitution site on the parent benzene ring to which it is connected is at the meta or para position of the benzene ring.

[0045] Z is O, S,

[0046] Ar is a substituted or unsubstituted group selected from the following groups,

[0047]

[0048]

[0049] The term "substituted or unsubstituted" as used herein means substitution with at least one selected from the group consisting of halogen, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclohexyl and adamantane.

[0050] In a preferred embodiment of the present invention, the compound may have the following structure,

[0051]

[0052] Ar 1 ,Ar 2 , L 1 , L 2 , L 3 , L 4 , R 1 , R 2 , Y, Z, and A have the same meanings as in formula (1).

[0053] In a preferred embodiment of the present invention, L 1 , L 2 Each is independently selected from a single bond or a substituted or unsubstituted C6-C12 arylene group, or a substituted or unsubstituted C3-C12 heteroarylene group,

[0054] L 3 , L 4 Each is independently selected from a single bond or a substituted or unsubstituted C6-C12 arylene group;

[0055] The substituents mentioned above are each independently selected from any one or a combination of at least two of a C1-C20 chain alkyl group, a C3-C20 cycloalkyl group, a C1-C20 alkoxy group, or a C6-C30 aryl group.

[0056] In a preferred embodiment of the present invention, L 1 , L 2 Each is independently selected from a single bond or a substituted or unsubstituted one or a combination of at least two of the following groups:

[0057]

[0058] Y 1 Each independently selected from O, S, NR 11 or CR 12 R 13 ; R 11 , R 12 , R 13 Each is independently selected from one of hydrogen, C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, halogen, cyano, nitro, hydroxyl, ester, amino, C6-C30 aryl, and C3-C30 heteroaryl;

[0059] L 3 , L 4 Each is independently selected from a single bond or a substituted or unsubstituted one of the following groups:

[0060]

[0061]

[0062] The expression of "—" crossing the ring structure indicates that the connection site is any position on the ring structure that can form a bond, and the wavy line indicates the connection site. The substitution in the above "substituted or unsubstituted" refers to substitution with at least one selected from halogen, phenyl, cyano, methyl, cyclohexane, cyclopentane, and fluorenyl.

[0063] Preferably, L 1 , L 2 , L 3 , L 4 All are selected from one of the following groups:

[0064]

[0065] In a preferred embodiment of the present invention, group A is selected from the following substituted or unsubstituted groups,

[0066]

[0067]

[0068]

[0069] The wavy line indicates the connection site. The substitution in the above “substituted or unsubstituted” refers to substitution with at least one selected from halogen, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclohexane, and adamantane.

[0070] In a preferred embodiment of the present invention, Ar 1 and Ar 2 Each is independently selected from one of the following substituted or unsubstituted groups:

[0071]

[0072] The term "substituted or unsubstituted" as used herein means substituted by at least one selected from the group consisting of halogen, phenyl, cyano, methyl, ethyl, isopropyl, cyclohexyl, and cyclopentyl.

[0073] Preferably, Ar 1 and Ar 2 Each is independently selected from one of the following groups:

[0074]

[0075] Wavy lines indicate junction sites.

[0076] In a preferred embodiment of the present invention, R 1 , R 2 , R 3 Each is independently selected from H, methyl, ethyl, isopropyl, tert-butyl, phenyl, and cyano.

[0077] Furthermore, the general formula compound of the present invention is preferably the following specific compound, but the present invention is not limited to the specific compounds shown below:

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095] It should be noted that, for the sake of convenience, the possible effects of each group / feature are described separately in this application, but this does not mean that these groups / features act in isolation. In fact, the reason for obtaining good performance is essentially the optimized combination of the entire molecule, which is the result of the synergistic effect between the various groups, rather than the effect of a single group.

[0096] In a second aspect, the present invention provides a use of the compound as described in the first aspect, wherein the compound is used in an organic electronic device.

[0097] Preferably, the organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a sheet-type scanner or electronic paper.

[0098] Preferably, the compound is used in an organic electroluminescent device. Preferably, the compound is used in a red light organic electroluminescent device.

[0099] Preferably, the compound is used as a light-emitting layer material in an organic electroluminescent device. Preferably, the compound is used as a light-emitting layer host material in an organic electroluminescent device.

[0100] In a third aspect, the present invention provides an organic electroluminescent device, comprising a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode; the organic layer comprises at least one compound as described in the first aspect.

[0101] Preferably, the organic layer comprises at least one compound having the structure as described in the first aspect.

[0102] Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one compound as described in the first aspect.

[0103] Preferably, the light-emitting layer comprises a host material and a doping material, and the host material comprises at least one compound as described in the first aspect.

[0104] As a preferred technical solution of the present invention, the compound is used as the main material of the light-emitting layer, which is an electronic main material with low triplet energy difference, and is particularly suitable as the main material of the red light-emitting layer, and can improve the service life of the organic electroluminescent device.

[0105] Preferably, the host material comprises a combination of a first host material and a second host material, and the first host material comprises at least one compound as described in the first aspect.

[0106] Preferably, the second host material is the following compound.

[0107]

[0108] Wherein, Ar3, Ar4, and Ar5 are each independently selected from any one of substituted or unsubstituted C6-C60 aryl groups, substituted or unsubstituted C3-C60 heteroaryl groups, and the substituted substituents are each independently selected from one or a combination of at least two of deuterium, halogen, C1-C20 chain alkyl groups, C2-C10 alkenyl groups, C3-C20 cycloalkyl groups, C2-C20 heterocycloalkyl groups, C1-C10 alkoxy groups, carboxyl groups, nitro groups, cyano groups, amino groups, hydroxyl groups, mercapto groups, C1-C20 alkylsilyl groups, C1-C20 alkylamino groups, C6-C30 arylamino groups, C3-C30 heteroarylamino groups, C6-C30 aryloxy groups, C3-C30 heteroaryloxy groups, C6-C60 aryl groups, and C3-C60 heteroaryl groups.

[0109] Preferably, the compound is used as the first host material in a dual host device, which has excellent electron transport properties and is compounded with the second host material to effectively regulate and achieve the transport balance of holes and electrons, thereby further improving the efficiency and life of the device and improving the overall performance of the device.

[0110] Preferably, the mass ratio of the first host material to the second host material is (0.1-2):1, for example, it can be 0.2:1, 0.3:1, 0.4:1, 0.5:1, 0.6:1, 0.7:1, 0.8:1, 0.9:1, 1:1, 1.1:1, 1.2:1, 1.3:1, 1.4:1, 1.5:1, 1.6:1, 1.7:1, 1.8:1 or 1.9:1, and is further preferably (0.5-1.5):1.

[0111] Preferably, the organic layer further comprises a hole transport region and an electron transport region. Preferably, the hole transport region comprises any one of a hole injection layer, a hole transport layer or an electron blocking layer, or a combination of at least two thereof. Preferably, the electron transport region comprises any one of an electron injection layer, an electron transport layer or a hole blocking layer, or a combination of at least two thereof.

[0112] The present invention also protects an electronic device having a display screen or a display panel, wherein the display screen or the display panel adopts the above-mentioned organic electroluminescent device. DETAILED DESCRIPTION

[0113] The technical solution of the present invention is further described in more detail below. It should be understood by those skilled in the art that the specific implementation methods and examples are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0114] The process of obtaining the compound of the present invention is as follows:

[0115] The compound represented by formula (1) of the present invention can be obtained by a known method, for example, by a known organic synthesis method. An exemplary synthesis route is given below, but those skilled in the art can also obtain it by other known methods. For example, the intermediate benzoxazole or benzothiazole derivatives that can be purchased in the present invention are as follows:

[0116]

[0117] Those that cannot be purchased directly can be prepared by the method in Journal of Combinatorial Chemistry, 2009 Vol. 11, No. 2 199:

[0118]

[0119] R 5 -R 8 It can be taken from halogen or the general formula R 3 definition.

[0120] Aldehyde (1.0 mmol), amine (1.0 mmol) and poly [4-diacetoxyiodostyrene] PDAIS (1.5 mmol) were dissolved in CH2Cl2 (50 mL). The reaction mixture was stirred at room temperature for 5-10 min. After completion, the reaction mixture was diluted with methanol and the precipitate was filtered off. The filtrate was concentrated and purified by silica gel column chromatography to obtain pure benzoxazole / benzothiazole.

[0121] According to the above method: benzaldehyde (1.0mmol), 2-amino-3-bromo-5-chlorothiophenol (1.0mmol) and poly [4-diacetoxyiodophenyl] PDAIS (1.5mmol) were dissolved in CH2Cl2 (50mL). The reaction mixture was stirred at room temperature for 5-10min, and after completion, the reaction mixture was diluted with methanol and the precipitate was filtered out. The filtrate was concentrated and purified by silica gel column chromatography to give S3, 4-bromo-6-chloro-2-phenylbenzothiazole (MS, 324.712).

[0122] Replacing 2-amino-3-bromo-5-chlorothiophenol with an equivalent of 2-amino-6-bromo-4-chlorothiophenol gave S4 (MS, 324.713).

[0123]

[0124] The substituents are then replaced by various coupling reactions. For details, please refer to the specific synthesis examples below.

[0125] Description of organic EL elements

[0126] The OLED device structure of the present invention may be an existing device structure, generally comprising a first electrode, a second electrode, and an organic material layer between the electrodes. The organic material layer may be divided into multiple regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.

[0127] In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a thin film transistor (TFT) may also be provided on the substrate used as a display.

[0128] The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO) and any combination thereof can be used. When the first electrode is used as a cathode, a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and any combination thereof can be used.

[0129] The organic material layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic material layer can be organic small molecules, organic macromolecules and polymers, and combinations thereof.

[0130] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer.

[0131] The material of the hole transport layer can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives such as the compounds shown in HT-1 to HT-51 below, or any combination thereof.

[0132]

[0133]

[0134]

[0135] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can use one or more compounds of HT-1 to HT-51 above, or one or more compounds of HI-1 to HI-3 below; or one or more compounds of HT-1 to HT-51 can be doped with one or more compounds of HI-1 to HI-3 below.

[0136]

[0137] The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit light of different wavelength spectra, and may also include a host material (Host). The light-emitting layer may be a monochrome light-emitting layer that emits a single color such as red, green, and blue. A plurality of monochrome light-emitting layers of different colors may be arranged in a plane according to a pixel pattern, or may be stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they may be separated from each other or may be connected to each other. The light-emitting layer may also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

[0138] According to different technologies, the light-emitting layer material can be made of different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescent materials. In an OLED device, a single light-emitting technology can be used, or a combination of multiple different light-emitting technologies can be used. These different light-emitting materials classified by technology can emit light of the same color or different colors.

[0139] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. The main material of the light-emitting layer includes a combination of a first main material and a second main material, wherein the first main material includes at least one compound described in Formula I.

[0140] The second main material has Specifically, the second host material can be selected from, but not limited to, one or more combinations of the following specific compounds H1 to H28.

[0141]

[0142]

[0143] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of RPD-1 to RPD-28 listed below.

[0144]

[0145] In one aspect of the present invention, an electron blocking layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may be one or more compounds of HT-1 to HT-51, but is not limited thereto.

[0146] The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region may also be a multilayer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0147] In one aspect of the present invention, the electron transport layer material can be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0148]

[0149]

[0150]

[0151] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may be one or more compounds of the above ET-1 to ET-73, but is not limited thereto.

[0152] The device may also include an electron injection layer located between the electron transport layer and the cathode, and the electron injection layer material includes but is not limited to one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, and Yb.

[0153] Example

[0154] The organic compounds of the present invention were synthesized representatively, and applied together with corresponding comparative compounds in organic electroluminescent devices to test the device performance under the same conditions.

[0155] Synthesis Example

[0156] The specific preparation method of the above-mentioned new compound of the present invention will be described in detail below by taking a plurality of synthesis examples as examples, but the preparation method of the present invention is not limited to these synthesis examples. It should be noted that obtaining the compound is not limited to the synthesis method and raw materials used in the present invention, and those skilled in the art may also select other methods or routes to obtain the compound proposed by the present invention. The compounds of the synthesis method not mentioned in the present invention are raw materials obtained from commercial channels, or are made by themselves according to known methods through these raw materials. The solvents and reagents used in the present invention, such as dichloromethane, petroleum ether, ethanol, tert-butylbenzene, boron tribromide, carbazole, diphenylamine, and other chemical reagents, can all be purchased from the domestic chemical product market, such as purchased from Sinopharm Group Reagent Company, TCI Company, Shanghai Bid Pharmaceutical Company, Bailingwei Reagent Company, etc. The analysis and detection of the intermediates and compounds in the present invention uses an ABSCIEX mass spectrometer (4000QTRAP).

[0157] Synthesis example 1

[0158] The synthesis route of compound N1 is as follows:

[0159]

[0160] The intermediate S1 (0.3 mol), pinacol borate (0.4 mol), potassium acetate (0.5 mol), 1,1-bis(diphenylphosphine)diferronichloridopalladium (0.005 mol) and dioxane (1500 mL) were added to a reaction flask, heated to 90 ° C for 6 h, and the reaction was completed by monitoring by thin layer chromatography (TLC). Water and dichloromethane were added for extraction, and the organic phase was separated and concentrated to obtain the intermediate N1-1.

[0161] N1-1 (0.1 mol), 2-chloro-4,6-diphenyl-1,3,5-triazine (0.1 mol), potassium carbonate (0.12 mol), tetrakis(triphenylphosphine)palladium (0.001 mol), water (50 mL) and dioxane (500 mL) were added to a reaction bottle, heated to 100 °C for 4 h, and the reaction was complete under the monitoring of TLC. After cooling, the mixture was extracted with dichloromethane and concentrated. The concentrate was recrystallized from toluene to obtain the target product N1-2.

[0162] N1-2 (0.05 mol), N1-S (0.05 mol), potassium carbonate (0.0.07 mol), tris(dibenzylideneacetone)dipalladium (0.0005 mol), 2-dicyclohexylphosphine-2′,6′-dimethoxy-biphenyl, water (30 mL) and dioxane (300 mL) were added to a reaction bottle and heated to 100°C for 4 h. The reaction was complete under TLC monitoring. After cooling, a large amount of solid was washed out. The filter cake was washed once with water and once with ethanol. After drying, it was recrystallized from xylene to obtain the target product N1 (MS, 643.212).

[0163] Synthesis example 2

[0164] The synthesis route of compound N39 is as follows:

[0165]

[0166] The intermediate dibenzofuran-4-boric acid (0.1 mol), S1 (0.1 mol), potassium carbonate (0.12 mol), tetrakis(triphenylphosphine)palladium (0.0001 mol), water (30 mL) and dioxane (300 mL) were added to a reaction bottle and heated to 100 °C for 4 h. The reaction was completed under the control of TLC. After cooling, the mixture was extracted with dichloromethane and concentrated. The concentrate was recrystallized from toluene to obtain the target product N39-1.

[0167] The intermediate N39-1 (0.07 mol), pinacol borate (0.1 mol), potassium acetate (0.12 mol), 1,1-bis(diphenylphosphine)diferronichloridopalladium (0.0007 mol) and dioxane (300 mL) were added to a reaction flask, heated to 110°C for 6 h, and the reaction was completed by monitoring by thin layer chromatography (TLC). Water and dichloromethane were added for extraction, and the organic phase was separated and concentrated to obtain a brown viscous liquid, which was heated with ethanol, boiled and washed, and then filtered to obtain the intermediate N39-2.

[0168] N39-2 (0.05 mol), 2-chloro-4,6-diphenyl-1,3,5-triazine (0.06 mol), potassium carbonate (0.0.07 mol), tetrakis(triphenylphosphine)palladium (0.0005 mol), water (30 mL) and dioxane (300 mL) were added to a reaction bottle and heated to 100 °C for 4 h. The reaction was complete under TLC monitoring. After cooling, a large amount of solid was washed out. The filter cake was washed once with water and once with ethanol. After drying, it was recrystallized from xylene to obtain the target product N39 (MS, 593.194).

[0169] Synthesis example 3

[0170] The synthesis route of compound N196 is as follows:

[0171]

[0172] The intermediate dibenzothiophene-1-boric acid (0.1 mol), S1 (0.1 mol), potassium carbonate (0.12 mol), tetrakis(triphenylphosphine)palladium (0.0001 mol), water (30 mL) and dioxane (300 mL) were added to a reaction bottle and heated to 100 °C for 4 h. The reaction was completed under the control of TLC. After cooling, the mixture was extracted with dichloromethane and concentrated. The concentrate was recrystallized from toluene to obtain the target product N196-1.

[0173] N39-2 (0.05 mol), 2,4-diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine (0.06 mol), potassium carbonate (0.0.07 mol), tetrakis(triphenylphosphine)palladium (0.0005 mol), water (30 mL) and dioxane (300 mL) were added to a reaction bottle, heated to 100 ° C for 4 h, and the reaction was completed under TLC monitoring. After cooling, a large amount of solid was washed out, and the filter cake was washed once with water and once with ethanol. After drying, it was recrystallized from xylene to obtain the target product N196 (MS, 701.183).

[0174] The present invention exemplarily provides a specific synthesis method for all intermediate parent core compounds, as well as an example of synthesizing the compounds of the present invention by Suzuki reaction of some parent cores with triazine raw materials. For other compounds for which no specific synthesis method is provided, they are also prepared by similar methods, and only the raw materials need to be replaced, which will not be described in detail here, or those skilled in the art can also prepare them by other methods in the prior art.

[0175] Device Embodiment

[0176] The preparation process of the organic electroluminescent device in this embodiment is as follows:

[0177] Example 1

[0178] The embodiments and comparative examples respectively provide organic electroluminescent devices, specifically,

[0179] Example 1 includes an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode (Al) arranged in sequence; the specific preparation method is as follows:

[0180] (1) a glass plate coated with an ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone / ethanol, baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0181] (2) Place the glass plate with the ITO anode in a vacuum chamber and evacuate the chamber to a vacuum of less than 1×10 -5 Pa, vacuum evaporating a mixture of compound HT-29:HI-1 (97 / 3, w / w) on the above anode layer as a hole injection layer, the evaporation rate is 0.1 nm / s, and the evaporation film thickness is 10 nm;

[0182] (3) Vacuum evaporation of compound HT-29 on the hole injection layer as a hole transport layer, with an evaporation rate of 0.1 nm / s and a film thickness of 60 nm;

[0183] (4) vacuum evaporating compound HT-37 on the hole transport layer as an electron blocking layer, with an evaporation rate of 0.1 nm / s and a film thickness of 60 nm;

[0184] (5) vacuum evaporating a light-emitting layer on the electron blocking layer, wherein the light-emitting layer includes a main material and a doping material (dye, RPD-18), and the mass ratio (w / w) of the main material to the doping material is 100:3; the main material is a mixture of a first main material (compound N1 provided by the present invention) and a second main material (compound H25) (the mass ratio of N1 to H25 is 1:1); the evaporation is carried out by a dual-source co-evaporation method, the evaporation rate is 0.1 nm / s, and the total evaporation film thickness is 40 nm;

[0185] (6) vacuum evaporating compound ET-17 on the light-emitting layer as a hole blocking layer at a rate of 0.1 nm / s and a film thickness of 5 nm;

[0186] (7) vacuum evaporating a mixture of compounds ET-66:ET-57 (50 / 50, w / w) on the hole blocking layer as an electron transport layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 25 nm;

[0187] (8) vacuum evaporating a compound LiF on the electron transport layer as an electron injection layer at a rate of 0.1 nm / s and a thickness of 1 nm;

[0188] (9) Vacuum-evaporating metal aluminum with a thickness of 150 nm on the electron injection layer as a cathode at a deposition rate of 1 nm / s to obtain the organic electroluminescent device.

[0189] Examples 2-16, Comparative Examples 1-3

[0190] The implementation method is basically the same as Example 1, except that the host material of the light-emitting layer is replaced with the material in the table, and the mass ratio of the first host material to the second host material is 1:1.

[0191] The structure of the main material in the comparative example is as follows:

[0192]

[0193] The host materials used for comparison are known host materials, and these compounds are synthesized by referring to relevant literature.

[0194] Performance test of organic electroluminescent devices:

[0195] At the same brightness of 3000cd / m 2 Under these conditions, the voltage and current density of the organic electroluminescent device are measured, and the ratio of brightness to current density is the current efficiency.

[0196] In Table 1, the life test value of Comparative Example 1 is recorded as 1, and the values ​​of other embodiments are all ratios to the test value of Comparative Example 1.

[0197] Table 1:

[0198]

[0199]

[0200] From the above data, it can be seen that the material of the present invention is superior to the comparative compound in terms of voltage and efficiency. The only difference between N224 and Ref-1 is the difference between phenyl and dibenzofuran on the oxazole ring. The introduction of dibenzofuran in the present invention makes the LUMO energy level of the material deeper, which is more conducive to the transmission of electrons, and its working voltage is further reduced. After containing heteroatom substituents such as dibenzofuran or thiophene, the S1 state of such groups belongs to the n, π* type, and the n-π* transition belongs to the spin-forbidden transition. The corresponding fluorescence intensity is very weak or does not emit fluorescence, so it has a higher energy transfer efficiency in the phosphorescent system, and the efficiency is improved. Compared with the present invention, the synergistic effect of the heteroatom substituent and the triazine group of Ref-2 is interrupted by the oxazole group. Although the voltage is lower than that of Ref-1, the fluorescence intensity of such heteroatom substituents is very weak or does not emit fluorescence, which is only applicable in conjugated aromatic systems, and the heteroatom substituent of dibenzothiophene in Ref-2 is blocked by the oxazole group, so it does not show a higher efficiency. The difference between Ref-3 and the present invention lies in the different bridging bonds. The electron mobility of the aromatic bridge is significantly lower than that of the heterocyclic bridge compound of the present invention, which makes electron injection and transmission difficult and presents a significantly high voltage.

[0201] The present invention illustrates the detailed method of the present invention through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned detailed method, that is, it does not mean that the present invention must rely on the above-mentioned detailed method to be implemented. Although the present invention is described in conjunction with the embodiments, the present invention is not limited to the above-mentioned embodiments. It should be understood that under the guidance of the concept of the present invention, those skilled in the art can make various modifications and improvements. The attached claims summarize the scope of the present invention. The equivalent replacement of the raw materials of the product of the present invention, the addition of auxiliary components, the selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A polyheteroaryl-substituted fused ring compound, characterized in that: It is a structure shown in formula (1): In formula (1), Y is O or S; Group A is a group represented by formula (a-1); Z is O, S or NR 5 , R 5 One selected from substituted or unsubstituted C1-C20 straight or branched alkyl, C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; Ar 1 ,Ar 2 is one of a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C3-C60 heteroaryl group; L 1 , L 2 , L 3 , L 4 Each independently represents a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C6-C60 fused ring arylene group, a substituted or unsubstituted C3-C60 heteroarylene group, or a substituted or unsubstituted C3-C60 fused ring heteroarylene group; Ar is a C6-C24 aryl group; R 1 , R 2 , R 3 is represented by one or more substituents, each independently selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl, when R 1 and R 2 When there are multiple R, they can be connected to each other to form a ring, or fused with adjacent benzene rings to form a ring. 3 When there are multiple rings, they form a ring with each other or condense with adjacent benzene rings to form a ring or are not connected; The term "substituted or unsubstituted" as used herein means substituted by any one or a combination of at least two of a group independently selected from halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; "*" indicates the connection site, and "—" crosses the ring structure, indicating that the connection site is at any position on the ring structure that can form a bond.

2. The polyheteroaryl-substituted fused ring compound according to claim 1, characterized in that: L 3 and L 4 The substitution site on the parent benzene ring to which it is connected is at the meta position of the benzene ring; Z is O, S; Ar is a substituted or unsubstituted group selected from the following groups, The substitution in the above-mentioned "substituted or unsubstituted" means substitution by at least one selected from halogen, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclohexyl and adamantane.

3. The polyheteroaryl-substituted fused ring compound according to claim 1, characterized in that: The structure represented by formula (1) is a structure represented by the following formula (1-1), formula (1-2) or (1-3), Ar 1 ,Ar 2 , L 1 , L 2 , L 3 , L 4 , R 1 , R 2 , Y, Z, and A have the same meanings as in formula (1).

4. The polyheteroaryl-substituted fused ring compound according to claim 1 or 3, wherein: L 1 , L 2 Each is independently selected from a single bond or a substituted or unsubstituted C6-C12 arylene group, or a substituted or unsubstituted C3-C12 heteroarylene group; L 3 , L 4 Each is independently selected from a single bond or a substituted or unsubstituted C6-C12 arylene group; The above-mentioned substituents are each independently selected from any one or a combination of at least two of a C1-C20 chain alkyl group, a C3-C20 cycloalkyl group, a C1-C20 alkoxy group, or a C6-C30 aryl group; Preferably, L 1 , L 2 Each is independently selected from a single bond or a substituted or unsubstituted one of the following groups; Y 1 Each independently selected from O, S, NR 11 or CR 12 R 13 ; R 11 is selected from one of hydrogen, C1-C20 linear alkyl, C1-C20 linear halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl; R 12 , R 13 Each is independently selected from one of hydrogen, C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, halogen, cyano, nitro, hydroxyl, ester, amino, C6-C30 aryl, and C3-C30 heteroaryl; L 3 , L 4 Each is independently selected from a single bond or a substituted or unsubstituted one of the following groups: The expression of "—" crossing the ring structure indicates that the connection site is any position on the ring structure that can form a bond, and the wavy line indicates the connection site. The substitution in the above "substituted or unsubstituted" refers to substitution with at least one selected from halogen, phenyl, cyano, methyl, cyclohexane, cyclopentane, and fluorenyl. Preferably, L 1 , L 2 , L 3 , L 4 All are selected from one of the following groups: 。 5. The polyheteroaryl-substituted fused ring compound according to claim 1 or 3, wherein: The group A is selected from the following substituted or unsubstituted groups, The wavy line indicates the connection site. The substitution in the above "substituted or unsubstituted" refers to substitution with at least one selected from halogen, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclohexane, and adamantane.

6. The polyheteroaryl-substituted fused ring compound according to claim 1 or 3, wherein: Ar 1 and Ar 2 Each is independently selected from one of the following substituted or unsubstituted groups: The term "substituted or unsubstituted" as used herein means substituted by at least one selected from the group consisting of halogen, phenyl, cyano, methyl, ethyl, isopropyl, cyclohexyl, and cyclopentyl. Preferably, Ar 1 and Ar 2 Each is independently selected from one of the following groups: Wavy lines indicate junction sites.

7. The polyheteroaryl-substituted fused ring compound according to claim 1 or 3, characterized in that: R 1 , R 2 , R 3 Each is independently selected from H, methyl, ethyl, isopropyl, tert-butyl, phenyl, and cyano.

8. The polyheteroaryl-substituted fused ring compound according to claim 1, characterized in that: It is the following compound 9. Use of the organic compound according to any one of claims 1 to 8 in an organic electronic device; Preferably, the organic electronic device comprises an organic electroluminescent device; Preferably, the application is application as a light-emitting layer material in an organic electroluminescent device.

10. An organic electroluminescent device comprising a first electrode, a second electrode and an organic layer inserted between the first electrode and the second electrode, characterized in that: The organic layer contains the organic compound according to any one of claims 1 to 8; Preferably, at least one of the organic layers is a light-emitting layer, and the light-emitting layer contains the organic compound according to any one of claims 1 to 8.

11. The organic electroluminescent device according to claim 10, wherein the light-emitting layer comprises a host material and a dye, and the host material comprises at least one organic compound according to any one of claims 1 to 8; Preferably, the host material comprises a combination of a first host material and a second host material, and the first host material comprises at least one organic compound according to any one of claims 1 to 8.

12. The organic electroluminescent device according to claim 11, wherein the second host material is a compound represented by the following general formula (3): in, The Ar 3 ,Ar 4 ,Ar 5 Each is independently selected from any one of a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C3-C60 heteroaryl group, The substituted substituents are each independently selected from one or a combination of at least two of halogen, C1-C20 chain alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl. 13 . The organic electroluminescent device according to claim 12 , wherein the mass ratio of the first host material to the second host material is 0.1-2:1, and more preferably 0.5-1.5:

1.

14. A display device, characterized in that: The display device comprises the organic electroluminescent device according to claim 10.

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