CN117126149B - Heterocyclic compound and organic electroluminescent device thereof - Google Patents

Heterocyclic compound and organic electroluminescent device thereof

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Publication number
CN117126149B
CN117126149B CN202311092184.4A CN202311092184A CN117126149B CN 117126149 B CN117126149 B CN 117126149B CN 202311092184 A CN202311092184 A CN 202311092184A CN 117126149 B CN117126149 B CN 117126149B
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deuterium
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CN117126149A (en
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郭建华
苗玉鹤
刘喜庆
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Changchun Hyperions Technology Co Ltd
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    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
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  • Optics & Photonics (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

本发明提供了一种杂环化合物及其有机电致发光器件，涉及有机电致发光材料技术领域。本发明的杂环化合物具有良好的稳定性和成膜性，应用于有机电致发光器件中时具有合适的三线态能级，能够有效降低驱动电压、提高器件的发光效率，延长器件的使用寿命，同时该化合物的制备方法简单，原料易得，能够满足工业化需求，在平板显示和固态照明等领域具有良好的产业化前景。This invention provides a heterocyclic compound and its organic electroluminescent device, relating to the field of organic electroluminescent materials technology. The heterocyclic compound of this invention exhibits good stability and film-forming properties. When applied to organic electroluminescent devices, it possesses suitable triplet energy levels, effectively reducing driving voltage, improving device luminous efficiency, and extending device lifespan. Furthermore, the compound's preparation method is simple, and the raw materials are readily available, meeting industrialization requirements and demonstrating promising industrialization prospects in fields such as flat panel displays and solid-state lighting.

Description

Heterocyclic compound and organic electroluminescent device thereof
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a heterocyclic compound and an organic electroluminescent device thereof.
Background
With the continuous updating of electronic devices such as mobile phones and computers in recent years, the requirements and the dependence of people on display are increasing. And organic photoelectric functional materials are attracting attention in the display field because of their excellent properties. The organic light-EmittingDiode, OLED has the advantages of higher response speed, wider color gamut, lower power consumption and other excellent characteristics compared with the LCD, so that the organic light-emitting device has larger advantages and wide application prospect.
The organic electroluminescent device is a multilayer thin film structure belonging to the sandwich type. The most typical organic electroluminescent device generally comprises three organic layers, a hole transport layer HIL, a light emitting layer ELL, and an electron transport layer ETL. In order to further improve the performance parameters such as luminous efficiency, luminous brightness and the like of the device, people continuously perfects the structure of the device and increase material layers with independent functions. I.e. a buffer layer such as an electron injection layer, a hole injection layer, an electron blocking layer, a hole blocking layer, etc. is added inside the electrode.
The electron transport material has poor stability because the electron mobility is far smaller than the hole mobility of the hole transport material, so that electrons and holes cannot be effectively transported to the light-emitting layer, and in addition, because of energy level mismatch, a part of electrons and holes escape to the outside of the light-emitting layer, thereby reducing the light-emitting efficiency of the organic electroluminescent device and increasing the driving voltage. The light-emitting layer is unbalanced in electron and hole migration due to the fact that triplet energy levels of the host and guest materials are not matched, and the efficiency of finally combining to form excitons is low, so that the light-emitting efficiency of the organic electroluminescent device is reduced.
Therefore, development of a host material of a light emitting layer which has high mobility and good stability, a hole blocking material capable of effectively blocking hole emission, and a light emitting layer which makes exciton utilization efficiency higher, so that improvement of various properties of an organic electroluminescent device is a direction that we should study.
Disclosure of Invention
In order to solve the problems, the invention provides a heterocyclic compound and an organic electroluminescent device thereof, and the application of the heterocyclic compound in the organic luminescent device can effectively improve the luminous efficiency of the device and prolong the service life of the device.
Specifically, the invention provides a heterocyclic compound, which has a structure represented by a formula I:
Group 1:
wherein Ar 1 is selected from any one of a formula II and a formula III;
The ring A is selected from any one of the structures in the group 1;
the ring B is selected from any one of C6-C18 aryl;
x is selected from any one of CH and N, and at least one of X is selected from N;
The Y is selected from any one of O, S, N (R d);
Y 1、Y2 is independently selected from any one of O, S, C (R aRb)、N(Rc);
the V is selected from any one of CH and N;
Ar 2 is selected from any one of aryl of a formula II, a formula III, substituted or unsubstituted C6-C30, heteroaryl of a substituted or unsubstituted C2-C30, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused ring groups of substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic rings, fused ring groups of substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings;
the L is selected from any one of single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C2-C30, substituted or unsubstituted alicyclic of C3-C30 and sub-condensed cyclic group of aromatic ring of C6-C30, substituted or unsubstituted alicyclic of C3-C25 and sub-condensed cyclic group of heteroaromatic ring of C2-C30, and Ar 1、Ar2、L、R2 contains at least one or more deuterium;
R 0、R1、R2、R3、R4 is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups;
The a 0 is selected from 0, 1,2, 3, 4, 5, 6, 7, 8, 9 or 10, when two or more R 0 are present, two or more R 0 are the same or different from each other;
The a 1 is selected from 0 or 1;
wherein a 2 is selected from 0, 1 or 2, when two R 2 are present, the two R 2 are the same or different from each other;
Wherein a 3 is selected from 0, 1, 2, 3 or 4, when two or more R 3 are present, two or more R 3 are the same or different from each other, or two adjacent R 3 are linked to each other to form a substituted or unsubstituted ring;
The a 4 is selected from 0,1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14, when two or more R 4 are present, two or more R 4 are the same or different from each other, or two adjacent R 4 are connected with each other to form a substituted or unsubstituted ring;
R a、Rb is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups, or R a、Rb;
The R c is selected from any one of substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups.
The invention also provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer positioned between the anode and the cathode, wherein the organic layer comprises at least one heterocyclic compound.
The beneficial effects are that:
The invention provides a heterocyclic compound which has higher electron mobility and triplet state energy level, and has good film forming property and thermal stability when being applied to an organic electroluminescent device. When the light-emitting layer is used as a main material of the light-emitting layer, the distribution of electrons and holes in the light-emitting layer is balanced, the exciton recombination area is wider, the utilization rate of excitons is improved, the light-emitting efficiency of the device is improved, and the service life is prolonged. Meanwhile, the preparation method of the compound is simple, raw materials are easy to obtain, the industrial requirement can be met, and the compound has good industrialization prospect.
Detailed Description
The following description of embodiments of the present invention will be made clearly and fully with reference to the accompanying drawings, in which it is shown, however, only some, but not all embodiments of the invention are shown. Modifications of the invention which are obvious to those skilled in the art are intended to fall within the scope of the invention.
In the present specification, "-" means a moiety attached to another substituent. "-" may be attached at any optional position of the attached group/fragment.
In this specification, when a substituent or linkage site is located across two or more rings, it is meant that it may be attached to either of the two or two rings, in particular to either of the respective selectable sites of the rings. For example, the number of the cells to be processed,Can represent Can representAnd so on.
In this specification, when the position of a substituent or attachment site on a ring is not fixed, it means that it can be attached to any of the optional sites of the ring.
For example, the number of the cells to be processed,Can represent Can represent Can representAnd so on.
Examples of halogens described herein may include fluorine, chlorine, bromine and iodine.
The term "link-forming ring" as used herein means that two groups are linked to each other by a chemical bond and optionally aromatized. As exemplified below:
In the present invention, the ring formed by the connection may be an aromatic ring system, an aliphatic ring system or a ring system formed by fusing both, and the ring formed by the connection may be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentaacene, cyclohexene, cyclohexane acene, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.
"Substituted or unsubstituted" as used herein, such as "substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted silyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene" means that at least one hydrogen atom on the group is replaced with a substituent. When a plurality of hydrogens are replaced with a plurality of substituents, the plurality of substituents may be the same or different. The substituents represented by the above "substituted or unsubstituted" may be independently selected from deuterium, tritium, cyano, nitro, amino, halogen atom, substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C3 to C30 silyl, substituted or unsubstituted C3 to C12 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heteroaryl, substituted or unsubstituted C1 to C12 alkoxy, substituted or unsubstituted C1 to C6 alkylthio, substituted or unsubstituted C1 to C12 alkylamino, substituted or unsubstituted C6 to C30 aryloxy, substituted or unsubstituted C6 to C30 arylamino, and the like, but are not limited thereto, and two adjacent substituents may be linked to form a ring. Preferably deuterium, tritium, cyano, nitro, amino, halogen atoms, C1-C12 alkyl, C3-C15 silyl, C3-C12 cycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, C1-C12 alkoxy, specific examples may include deuterium, tritium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, trimethylsilyl, triethylsilyl, tri-t-butylsilyl, triphenylsilyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, trifluoromethyl, trifluoroethyl, tridecylmethyl, methoxy, ethoxy, phenyl, tolyl, mesityl, pentadeuterophenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, perylene, pyrenyl, fluoranthenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl benzocyclohexenyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, 9-phenylcarbazolyl, 9' -spirobifluorenyl, carbazoloindolyl, pyrrolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzotriazolyl, benzimidazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenothiazinyl, phenoxazinyl, acridinyl, and the like, but is not limited thereto. Or when the substituent is plural, plural substituents may be the same or different from each other, or adjacent substituents may be linked to form a ring.
The alkyl group according to the present invention is a generic term for monovalent groups obtained by removing one hydrogen atom from an alkane molecule, and may be a straight chain alkyl group or a branched chain alkyl group, preferably having 1 to 25 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. Specific examples may include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, and the like, but are not limited thereto.
Cycloalkyl according to the invention is a generic term for monovalent radicals obtained by removing one hydrogen atom from a cyclic alkane molecule, preferably having 3 to 25 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 5 to 10 carbon atoms, most preferably 5 to 7 carbon atoms. Specific examples may include adamantyl, norbornyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like, but are not limited thereto.
The silyl group according to the present invention may be represented by a group according to-SiH 3, the substituted silyl group according to the present invention may be represented by a group according to-Si (Rs) (Rs) (Rs), and the Rs are hydrogen, deuterium, tritium, the substituted or unsubstituted alkyl group described above, substituted or unsubstituted alkoxy group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, etc., but not simultaneously hydrogen, deuterium, tritium, and the plurality of Rs in-Si (Rs) (Rs) (Rs) may be the same or different, preferably have 1 to 30 carbon atoms, preferably 1 to 25 carbon atoms, more preferably 3 to 22 carbon atoms, most preferably 3 to 18 carbon atoms, and examples may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyl-t-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, terphenylsilyl, tripropylsilyl, etc., but are not limited thereto.
The alicyclic group according to the present invention means a generic term of monovalent groups obtained by removing one hydrogen atom from an alicyclic hydrocarbon molecule, and may be cycloalkyl, cycloalkenyl, etc., preferably having 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, preferably 5 to 10 carbon atoms, most preferably 5 to 7 carbon atoms, and specific examples may include adamantyl, norbornyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto.
The heterocycloalkyl group according to the present invention refers to a generic term for groups obtained by substituting one or more carbon atoms in the heterocycloalkyl group with hetero atoms including, but not limited to, oxygen, sulfur, nitrogen, silicon or phosphorus atoms, preferably having 1 to 15 carbon atoms, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 6 carbon atoms. Specific examples may include, but are not limited to, tetrahydropyrrolyl, piperidinyl, and the like.
Aryl in the present invention refers to the generic term for monovalent radicals obtained by removing one hydrogen atom from the aromatic nucleus carbon of an aromatic compound molecule, which may be a monocyclic aryl, polycyclic aryl or fused ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl group refers to an aryl group having only one aromatic ring in the molecule, such as, but not limited to, phenyl, etc., the polycyclic aryl group refers to an aryl group having two or more independent aromatic rings in the molecule, and specific examples thereof may include, but are not limited to, biphenyl, terphenyl, tetrabiphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, etc., and the fused ring aryl group refers to an aryl group having two or more aromatic rings in the molecule and condensed by sharing two adjacent carbon atoms with each other, and specific examples thereof may include, but are not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylene, fluorenyl, benzofluorenyl, triphenylenyl, fluoranthryl, spirofluorenyl, spirobifluorenyl, etc.
Heteroaryl according to the present invention refers to the generic term for groups obtained after substitution of one or more aromatic nucleus carbon atoms in the aryl group with heteroatoms including, but not limited to, oxygen, sulfur, nitrogen, silicon or phosphorus atoms, preferably having 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, particularly preferably 2 to 15 carbon atoms, most preferably 2 to 12 carbon atoms. The attachment site of the heteroaryl group may be on a ring-forming carbon atom or on a ring-forming heteroatom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a fused ring heteroaryl group. The monocyclic heteroaryl specific examples may include, but are not limited to, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, etc., the polycyclic heteroaryl specific examples may include, but are not limited to, bipyridyl, phenylpyridyl, phenylpyrimidinyl, etc., and the fused ring heteroaryl specific examples may include, but are not limited to, quinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, quinoxalinyl, benzoquinazolinyl, benzoquinoxalinyl, phenanthroline, naphthyridinyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, benzodibenzothienyl, dibenzothienyl, dibenzooxazolyl, dibenzothienyl, carbazolyl, 9, 10-dihydroacridinyl, phenoxazinyl, phenothiazine, spirofluorenyl, thiofluorenyl, etc.
The fused ring group of the alicyclic ring and the aromatic ring refers to the generic term of monovalent groups obtained by removing one hydrogen atom after the alicyclic ring and the aromatic ring are fused together. Preferably having 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms, specific examples may include benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, and the like, but are not limited thereto.
The fused ring group of the heterocycloalkyl ring and the aromatic ring in the present invention refers to a generic term for monovalent groups obtained by fusing the heterocycloalkyl ring and the aromatic ring together and then removing one hydrogen atom. Preferably having 6 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms, specific examples may include benzoazetidinyl, benzotetrahydropyranyl, benzopiperidinyl, benzoazepanyl, naphthasprings tetrahydropyranyl, naphthasprings piperidinyl, phenanthrlocks piperidinyl, and the like, but are not limited thereto.
The fused ring group of the alicyclic ring and the heteroaromatic ring refers to the generic term of monovalent groups obtained by fusing the alicyclic ring and the heteroaromatic ring together and removing one hydrogen atom. Preferably having 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms, specific examples may include pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridocycloheptyl, pyrimidocyclopropyl, pyrimidocyclobutyl, pyrimidocyclopentyl, pyrimidocyclohexyl, pyrimidobenzcycloheptyl, dibenzofuran-cyclopropyl, dibenzofuran-cyclobutyl, dibenzofuran-cyclopentyl, dibenzofuran-cyclohexyl, dibenzofuran-cycloheptyl, dibenzothiophene-cyclopropyl, dibenzothiophene-cyclobutyl, dibenzothiophene-cyclopentyl, dibenzothiophene-cyclohexyl, dibenzothiophene-cycloheptyl, carbazolocyclopropyl, carbazolocyclobutyl, carbazolocyclopentyl, carbazolocyclohexyl, carbazolocycloheptyl, and the like, but are not limited thereto.
The alicyclic group according to the present invention means a generic term for divalent groups obtained by removing two hydrogen atoms from an alicyclic hydrocarbon molecule, and may be a cycloalkylene group, a cycloalkenylene group, or the like, preferably having 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, preferably 5 to 10 carbon atoms, and most preferably 5 to 7 carbon atoms, and specific examples may include, but are not limited to, a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, a cycloheptylene group, an adamantylene group, a norbornylene group, a cyclopropylene group, a cyclobutenyl group, a cyclopentylene group, a cyclohexenylene group, a cycloheptylene group, or the like.
The arylene group according to the present invention means a generic term for divalent groups obtained by removing two hydrogen atoms from an aromatic nucleus of an aromatic hydrocarbon molecule, and may be a monocyclic arylene group, a polycyclic arylene group or a condensed ring arylene group, preferably having 6 to 30 carbon atoms, preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms, and specific examples may include phenylene, biphenylene, terphenylene, naphthylene, anthrylene, phenanthrylene, pyrenylene, triphenylene, perylene, fluorenylene, fluoranthrylene, phenylenedenyl, and the like, but are not limited thereto.
Heteroaryl, as used herein, refers to the generic term for groups obtained after substitution of one or more of the aromatic nucleus carbons in the arylene group with heteroatoms, including but not limited to oxygen, sulfur, nitrogen, or phosphorus atoms. Preferably having 2 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, the heteroarylene group may be attached to a ring-forming carbon atom or to a ring-forming nitrogen atom, and the heteroarylene group may be a monocyclic heteroarylene group, a polycyclic heteroarylene group or a condensed ring heteroarylene group. The monocyclic and condensed ring heteroarylene specific examples may include, but are not limited to, a pyridylene group, a pyrimidinylene group, a triazinylene group, a furanylene group, a thiophenylene group, a carbazolylene group, a benzofuranylene group, a benzothiophenylene group, a benzofuranylene group, a dibenzofuranylene group, a dibenzocarbazolylene group, etc., and the polycyclic heteroarylene specific examples may include, but are not limited to, a bipyridylene group, a bipyrimidiylene group, a phenylpyridylene group, etc.
The term "fused ring-sub group" of an alicyclic ring and an aromatic ring as used herein refers to a generic term for divalent groups obtained by fusing an alicyclic ring and an aromatic ring together and then removing two hydrogen atoms. Preferably having 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms, specific examples may include benzobicyclopropyl, benzobicyclobutyl, benzocyclopentylene, benzocyclohexylene, benzocycloheptylene, benzocyclopentylene, benzocyclohexenylene, benzocycloheptylene, naphthocyclopropyl, naphthocyclobutylene, naphthocyclopentyl, naphthocyclohexyl, and the like, but are not limited thereto.
The term "fused ring-sub-group" as used herein refers to a generic term for divalent radicals obtained by fusing an alicyclic ring to a heteroaromatic ring and then removing two hydrogen atoms. Preferably having 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms, specific examples may include pyrido-cyclopropyl-, pyrido-cyclobutyl-, pyrido-cyclopentyl-, pyrido-cyclohexyl-, pyrido-benzoheptyl-, pyrimido-cyclopropyl-, pyrimido-cyclobutyl-, pyrimido-cyclopentyl-, pyrimido-cyclohexyl-, pyrimido-benzocycloheptyl-, dibenzofuran-cyclopropyl-, dibenzofuran-cyclobutyl-, dibenzofuran-benzocyclopentyl-, dibenzofuran-benzocyclohexyl-, dibenzofuran-benzocycloheptyl-, dibenzothiophene-benzocyclohexyl-, dibenzothiophene-benzocycloheptyl-, carbazolo-cyclopropyl-, carbazolo-and carbazolo-cycloheptyl-, and the like, but are not limited thereto.
The term "at least one", "one or more" as used herein includes one, two, three, four, five, six, seven, eight or more, where permitted.
The invention provides a heterocyclic compound, which has a structure represented by a formula I:
Group 1:
wherein Ar 1 is selected from any one of a formula II and a formula III;
The ring A is selected from any one of the structures in the group 1;
the ring B is selected from any one of C6-C18 aryl;
x is selected from any one of CH and N, and at least one of X is selected from N;
The Y is selected from any one of O, S, N (R d);
Y 1、Y2 is independently selected from any one of O, S, C (R aRb)、N(Rc);
the V is selected from any one of CH and N;
Ar 2 is selected from any one of aryl of a formula II, a formula III, substituted or unsubstituted C6-C30, heteroaryl of a substituted or unsubstituted C2-C30, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused ring groups of substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic rings, fused ring groups of substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings;
the L is selected from any one of single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C2-C30, substituted or unsubstituted alicyclic of C3-C30 and sub-condensed cyclic group of aromatic ring of C6-C30, substituted or unsubstituted alicyclic of C3-C25 and sub-condensed cyclic group of heteroaromatic ring of C2-C30, and Ar 1、Ar2、L、R2 contains at least one or more deuterium;
R 0、R1、R2、R3、R4 is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups;
The a 0 is selected from 0, 1,2, 3, 4, 5, 6, 7, 8, 9 or 10, when two or more R 0 are present, two or more R 0 are the same or different from each other;
The a 1 is selected from 0 or 1;
wherein a 2 is selected from 0, 1 or 2, when two R 2 are present, the two R 2 are the same or different from each other;
Wherein a 3 is selected from 0, 1, 2, 3 or 4, when two or more R 3 are present, two or more R 3 are the same or different from each other, or two adjacent R 3 are linked to each other to form a substituted or unsubstituted ring;
The a 4 is selected from 0,1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14, when two or more R 4 are present, two or more R 4 are the same or different from each other, or two adjacent R 4 are connected with each other to form a substituted or unsubstituted ring;
R a、Rb is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups, or R a、Rb;
The R c is selected from any one of substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups.
Preferably, the R 0、R1 is independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, Substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthocyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted tetrahydropyrrole, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tri-tert-butylsilyl, Substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furanyl, Substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thienyl substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl substituted or unsubstituted benzodibenzothienyl, substituted or unsubstituted carbazolyl substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted dibenzooxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted benzoxazolyl, Substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted bisbenzimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted indolyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, Any one of substituted or unsubstituted spirofluorene-thioxanthoyl and substituted or unsubstituted spirofluorene-thioxanthoyl.
Preferably, the heterocyclic compound is selected from any one of the following structures:
R p、Rq、Rr is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups;
The g 1 is selected from 0, 1,2,3, 4,5 or 6, the g 2 is selected from 0, 1,2,3, 4,5, 6, 7 or 8, the g 3 is selected from 0, 1,2,3, 4 or 5, the g 4 is selected from 0, 1,2,3, 4,5, 6 or 7, when two or more R q are present, two or more R q are the same or different from each other, or two adjacent R q are connected to each other to form a substituted or unsubstituted ring;
The h 1 is selected from 0, 1, 2, 3 or 4, when two or more R r are present, two or more R r are the same or different from each other, or two adjacent R r are connected to each other to form a substituted or unsubstituted ring.
Preferably, each R p、Rq、Rr is independently selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, substituted or unsubstituted, Substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthocyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted tetrahydropyrrole, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tri-tert-butylsilyl, Substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furanyl, Substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thienyl substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl substituted or unsubstituted benzodibenzothienyl, substituted or unsubstituted carbazolyl substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted dibenzooxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted benzoxazolyl, Substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted bisbenzimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted indolyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, Any one of substituted or unsubstituted spirofluorene-thioxanthoyl and substituted or unsubstituted spirofluorene-thioxanthoyl.
More preferably, the heterocyclic compound is selected from any one of the following structures:
Preferably, 0V in each structure of said group 1 and derived from group 1 is selected from the group consisting of N atoms, or 1V in each structure of said group 1 and derived from group 1 is selected from the group consisting of N atoms, or two V in each structure of said group 1 and derived from group 1 is selected from the group consisting of N atoms.
Preferably, the saidSelected from any one of the following structures:
preferably, the formula II is selected from any one of the following structures:
The R 9 is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups;
The f 1 is selected from 1,2,3, 4 or 5, the f 2 is selected from 1,2,3, 4,5, 6 or 7, the f 3 is selected from 1,2,3, 4,5, 6, 7, 8 or 9, the f 4 is selected from 1 or 2, the f 5 is selected from 1,2,3, 4,5, 6, 7 or 8, the f 6 is selected from 1,2,3 or 4, the f 7 is selected from 1,2 or 3, when two or more R 9 are present, two or more R 9 are the same or different from each other, or two adjacent R 9 are connected with each other to form a substituted or unsubstituted ring.
Preferably, the R 9 is selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, Substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthocyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted tetrahydropyrrole, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tri-tert-butylsilyl, Substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furanyl, Substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thienyl substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl substituted or unsubstituted benzodibenzothienyl, substituted or unsubstituted carbazolyl substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted dibenzooxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted benzoxazolyl, Substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted bisbenzimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted indolyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, Any one of substituted or unsubstituted spirofluorene-thioxanthoyl and substituted or unsubstituted spirofluorene-thioxanthoyl.
In one embodiment, one, two or more of R 9 in each structure are selected from deuterium.
Preferably, R 9 in each structure is not hydrogen.
Preferably, R 9 in each structure is selected from deuterium.
Preferably, the formula III is selected from any one of the following structures:
The R 5 is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups;
The b 1 is selected from 1,2, 3, 4 or 5, the b 2 is selected from 1,2, 3, 4, 5, 6 or 7, the b 3 is selected from 1,2, 3, 4, 5, 6, 7, 8 or 9, the b 4 is selected from 1 or 2, the b 5 is selected from 1,2, 3, 4, 5, 6, 7 or 8, the b 6 is selected from 1,2, 3 or 4, the b 7 is selected from 1,2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, the b 8 is selected from 1,2, 3, 4, 5 or 6, the b 9 is selected from 1,2 or 3, when two or more R 5 are present, two or more R 5 are the same or different from each other, or two adjacent R 5 are connected to each other to form a substituted or unsubstituted ring.
Preferably, the R 5, ra, rb are independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, substituted or unsubstituted, Substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthocyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted tetrahydropyrrole, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tri-tert-butylsilyl, Substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furanyl, Substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thienyl substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl substituted or unsubstituted benzodibenzothienyl, substituted or unsubstituted carbazolyl substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted dibenzooxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted benzoxazolyl, Substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted bisbenzimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted indolyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, Any one of substituted or unsubstituted spirofluorene-thioxanthoyl and substituted or unsubstituted spirofluorene-thioxanthoyl.
Preferably, the R c is selected from the group consisting of substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted t-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, substituted or unsubstituted cyclopentyl, Substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthocyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted tetrahydropyrrole, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tri-tert-butylsilyl, substituted or unsubstituted triphenylsilyl, Substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl substituted or unsubstituted dibenzothienyl, substituted or unsubstituted benzodibenzothienyl a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocarbazolyl group substituted or unsubstituted pyrrolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted dibenzooxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted dibenzooxazolyl, Substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted phenanthroline yl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted indolyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted spirofluorene oxazinyl, any one of substituted or unsubstituted spirofluorene thiaanthryl.
In one embodiment, one, two or more of R 5 in each structure are selected from deuterium.
Preferably, R 5 in each structure is not hydrogen.
Preferably, R 5 in each structure is selected from deuterium.
Preferably, when Ar 2 is not formula II or formula III, it is selected from any one of the following structures:
The R 6 is the same or different and is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups;
The c 1 is selected from 0, 1, 2,3, 4 or 5, the c 2 is selected from 0, 1, 2,3 or 4, the c 3 is selected from 0, 1, 2,3, 4, 5, 6 or 7, the c 4 is selected from 0, 1, 2,3, 4, 5, 6, 7, 8 or 9, the c 5 is selected from 0, 1 or 2, the c 6 is selected from 0, 1, 2,3, 4, 5, 6, 7, 8, 9, 10 or 11, the c 7 is selected from 0, 1, 2 or 3, when two or more R 6 are present, two or more R 6 are the same or different from each other, or two adjacent R 6 are connected with each other to form a substituted or unsubstituted ring;
R d is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
Z is selected from any one of CH and N;
Each Y 4、Y5 is independently selected from any one of O, S, C (R eRf)、N(Rg);
R e、Rf is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups, or R e、Rf;
The R g is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups.
Still preferably, when Ar 2 is not represented by formula II or formula III, it is selected from any one of the structures shown below:
The R 8 is the same or different and is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups;
The e 1 is selected from 0, 1,2,3,4 or 5, the e 2 is selected from 0, 1,2,3 or 4, the e 3 is selected from 0, 1,2 or 3, the e 4 is selected from 0, 1 or 2, said e 5 is selected from 0 or 1, said e 6 is selected from 0, 1, 2, 3,4, 5, 6 or 7, said e 7 is selected from 0, 1, 2, 3,4, 5 or 6, said e 8 is selected from 0, 1. 2, 3,4, 5, 6, 7, 8 or 9, said e 9 is selected from 0, 1,2, 3,4, 5, 6, 7 or 8, said e 10 is selected from 0, 1,2, 3,4, 5, 6, 7, 8, 9, 10 or 11, said e 11 is selected from 0, 0, 1.2, 3,4, 5, 6, 7, 8, 9 or 10, said e 12 being selected from 0,1, 2, 3,4, 5, 6, 7, 8, 9, 10, 11, 12 or 13, said e 13 being selected from 0,1, 2, 3,4, 5, 6, 7, 8, 9, 10, 11 or 12, said e 14 being selected from 0, 0, 1. 2,3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15, wherein e 15 is selected from 0, 1,2, 3,4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14, when two or more R 8 are present, two or more R 8 are the same or different from each other, or two adjacent R 8 are linked to each other to form a substituted or unsubstituted ring;
R m、Rn is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups.
Preferably, the R 8 is selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, Substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthocyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted tetrahydropyrrole, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tri-tert-butylsilyl, Substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furanyl, Substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thienyl substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl substituted or unsubstituted benzodibenzothienyl, substituted or unsubstituted carbazolyl substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted dibenzooxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted benzoxazolyl, Substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted bisbenzimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted indolyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, Any one of substituted or unsubstituted spirofluorene-thioxanthoyl and substituted or unsubstituted spirofluorene-thioxanthoyl.
In one embodiment, one, two or more of R 8 in each structure are selected from deuterium.
Preferably, R 8 in each structure is not hydrogen.
Preferably, R 8 in each structure is selected from deuterium.
Preferably, L is selected from a single bond or from any one of the following structures:
R 7 is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups;
the d 1 is selected from 0, 1,2,3 or 4, the d 2 is selected from 0, 1,2,3,4, 5 or 6, the d 3 is selected from 0, 1,2,3,4, 5, 6, 7 or 8, the d 4 is selected from 0, 1 or 2, the d 5 is selected from 0, 1,2,3,4, 5, 6 or 7, when two or more R 7 are present, two or more R 7 are the same or different from each other or two adjacent R 7 are connected with each other to form a substituted or unsubstituted ring;
the L 1 is selected from any one of single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C2-C30, substituted or unsubstituted alicyclic of C3-C30 and fused ring group of aromatic ring of C6-C30, substituted or unsubstituted alicyclic of C3-C25 and fused ring group of heteroaromatic ring of C2-C30;
the J is selected from any one of CH and N;
R h is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
the Y 6、Y7、Y8 is independently selected from any one of O, S, C (R iRj)、N(Rk);
R i、Rj is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups, or R i、Rj;
The R k is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups.
Still more preferably, L is selected from a single bond or from any one of the following structures:
Preferably, at least one of Ar 1、Ar2, L is selected from those containing deuterium in the foregoing groups.
More preferably, ar 1 is selected from those containing deuterium in the foregoing groups.
More preferably, ar 2 is selected from those containing deuterium in the foregoing groups.
More preferably, L is selected from those containing deuterium in the aforementioned groups.
Preferably, R 2 is each selected from deuterium.
Preferably, the compounds of the present invention contain at least one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty-one, twenty-two, twenty-three, twenty-four or twenty-five deuterium atoms.
Preferably, at least one of Ar 1、Ar2, L is substituted with one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty-one, twenty-two, twenty-three, twenty-four or twenty-five deuterium atoms.
Preferably, ar 1 is substituted with one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty-one, twenty-two, twenty-three, twenty-four or twenty-five deuterium atoms.
Preferably, ar 2 is substituted with one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty-one, twenty-two, twenty-three, twenty-four or twenty-five deuterium atoms.
Preferably, said L is substituted with one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty-one, twenty-two, twenty-three, twenty-four or twenty-five deuterium atoms.
Most preferably, the compound of formula I is selected from any one of the following structures:
the heterocyclic compounds of formula I of the present invention are shown in the above list of specific structural forms, but the present invention is not limited to the listed chemical structures, and substituents are included in the structures of formula I.
The invention also provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer positioned between the anode and the cathode, wherein the organic layer comprises at least one heterocyclic compound.
Preferably, the organic layer comprises at least one of an electron transport layer and a hole blocking layer, and at least one of the electron transport layer and the hole blocking layer comprises at least one of the heterocyclic compounds according to the present invention.
Preferably, the organic layer comprises a light-emitting layer comprising at least one of the heterocyclic compounds described in the present invention.
Still preferably, the organic layer comprises an electron transport layer comprising at least one of the heterocyclic compounds described herein.
Still preferably, the organic layer comprises a hole blocking layer comprising at least one of the heterocyclic compounds described herein.
The material of each layer of thin film in the organic electroluminescent device is not particularly limited, and materials known in the art can be used. The following describes each organic functional layer of the above-mentioned organic electroluminescent device and the electrodes on both sides of the device, respectively:
The anode material of the present invention is preferably a material having a high work function in order to improve hole injection efficiency. The anode may be a transmissive electrode, a reflective electrode, or a semi-transmissive electrode. When the anode is a transmissive electrode, the material used to form the anode may be selected from Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO), or any combination thereof, and when the anode is a semi-transmissive electrode or a reflective electrode, the material used to form the anode may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof. The anode may have a single-layer structure or a multi-layer structure including two or more layers, for example, the anode may have a single-layer structure of Al or a three-layer structure of ITO/Ag/ITO, but the structure of the anode is not limited thereto.
The cathode material according to the present invention, preferably a material having a low work function, is to improve electron injection efficiency, and the cathode may be selected from Ag, mg, cu, al, pt, pd, au, ni, nd, ir, cr, li, ca, liF/Ca, liF/Al, mo, ti, a compound including the same, or a mixture thereof (e.g., a mixture of Ag and Mg), but is not limited thereto.
The hole injection layer material disclosed by the invention is preferably a material with better hole injection capability and has more proper HOMO energy level so as to reduce the interface potential barrier between the anode and the hole transport layer and improve the hole injection capability. The hole injection layer material may include metalloporphyrin, oligothiophene, anthraquinone-based compounds, arylamine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene-based compounds, quinacridone-based compounds, anthraquinone-based compounds, and polyaniline-based and polythiophene-based conductive polymers, etc., but is not limited thereto.
The hole transport layer material according to the present invention is preferably a material having high hole mobility for hole injection, and may include, but is not limited to, biphenyldiamine derivatives, triarylamine derivatives, carbazole derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, anthraquinone compounds, quinacridone compounds, hexanitrile hexaazabenzophenanthrene compounds, polythiophene, polyaniline, polyvinylcarbazole, and the like.
The electron blocking layer material of the present invention is preferably a material having a good hole transporting ability and an electron blocking ability so as to efficiently transport holes and limit the escape of electrons to the light emitting layer interface. The electron blocking layer material can be selected from aromatic amine derivatives, carbazole derivatives, etc. Specific examples may include N, N-bis ([ 1,1' -biphenyl ] -4-yl) - (9H-carbazol-9-yl) - [1,1' -biphenyl ] -4-amine, N- (4 ' - (9H-carbazol-9-yl) - [1,1' -biphenyl ] -4-N- ([ 1,1' -biphenyl ] -4-yl) -9, 9-dimethyl-9H-fluoren-2-amine, N ' -bis (naphthalen-1-yl) -N, N ' -diphenyl-benzidine (NPD), and the like, but are not limited thereto.
The light-emitting layer material of the present invention may use red, green or blue light-emitting materials, and generally comprises a host material (also referred to as a host material) and a doped material (also referred to as a guest material), and the light-emitting layer material may comprise a plurality of host materials and a plurality of doped materials, and the guest material may be a simple fluorescent material or a phosphorescent material, or may be formed by combining fluorescent and phosphorescent materials. The host material of the light-emitting layer is required to have a bipolar charge transport property and an appropriate energy level to efficiently transfer excitation energy to the guest light-emitting material, and may contain anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene derivatives, fluoranthene derivatives, and the like, and heterocyclic ring-containing compounds including carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, distyrylaryl derivatives, stilbene derivatives, and the like, in addition to the heterocyclic compounds provided by the present invention, but is not limited thereto. The guest material may include, but is not limited to, a metal complex (e.g., iridium complex, platinum complex, osmium complex, rhodium complex, terbium complex, europium complex, etc.), anthracene derivative, pyrene derivative, perylene derivative, pyrrole derivative, indole derivative, carbazole derivative, etc.
The hole blocking layer of the present invention is preferably a material having a good electron transporting ability and a hole blocking ability so as to efficiently transport electrons and limit the escape of holes to the light emitting layer interface. The hole blocking layer material can be selected from metal complexes, quinoline derivatives, imidazole derivatives, phenanthrene derivatives, triazole derivatives, azabenzene derivatives and the like, and preferably at least one of the heterocyclic compounds according to the invention. Specific examples may include bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1, 1' -biphenyl-4-hydroxy) aluminum (BAlq), 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 3' - [5' - [3- (3-pyridyl) phenyl ] [1,1':3',1 "-terphenyl ] -3,3" -diyl ] bipyridine (TmPyPB), and the like, but are not limited thereto.
The electron transport layer material according to the present invention is preferably a material having high electron mobility for electron injection, and may include any one or more of the heterocyclic compounds according to the present invention or the following structures, thiazole derivatives, quinoline derivatives, benzimidazole derivatives, oxaoxazole derivatives, azabenzene derivatives, diazene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, phenanthroline derivatives, metal chelates, and the like, but is not limited thereto.
The electron injection layer material of the present invention is preferably a material having a good electron injection capability and a suitable LUMO energy level so as to reduce an interface barrier between the cathode and the electron transport layer and improve the electron injection capability, and may include metals, alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, metal complexes, metal oxides, and other substances having high electron injection capability. Specific examples may include, but are not limited to, ：Li、Ca、Sr、LiF、CsF、CaF2、BaO、Li2CO3、CaCO3、Li2C2O4、Cs2C2O4、CsAlF4、Al2O3、MoO3、MgF2、LiOx、Yb、Tb、8- cesium hydroxyquinoline, aluminum tris (8-hydroxyquinoline), and the like.
The cladding material of the present invention is preferably a material having a high refractive index in order to improve light extraction efficiency, and may include tris (8-hydroxyquinoline) aluminum (Alq 3), N '-bis (naphthalen-1-yl) -N, N' -bis (phenyl) -2,2 '-dimethylbenzidine (NPD), 4' -bis (9-Carbazole) Biphenyl (CBP), etc., but is not limited thereto.
The method for producing the thin films of each layer in the organic electroluminescent device of the present invention is not particularly limited, and vacuum deposition, sputtering, spin coating, spray coating, screen printing, laser transfer, etc. may be used, but are not limited thereto.
The organic electroluminescent device is mainly applied to the technical field of information display and the field of illumination, and is widely applied to various information displays in the aspect of information display, such as mobile phones, tablet computers, flat televisions, smart watches, VR, vehicle-mounted systems, digital cameras, wearable devices and the like.
The following is one preparation method of the compound represented by the formula I of the present invention, but the preparation method of the present invention is not limited thereto. The core structure of the compound of formula I may be prepared by the reaction scheme shown below, substituents may be bonded through methods known in the art, and the kind and position of substituents or the number of substituents may be changed according to techniques known in the art.
[ Synthetic route ]
Preparation of the compound of formula I:
The source of the raw materials used in the present invention is not particularly limited and may be commercially available products or prepared by a preparation method well known to those skilled in the art, for example, the intermediate d may be prepared by the following synthetic route:
preparation of intermediate d:
Xa, xb, xc, xd, xe, xf are each independently selected from any one of Cl, br, I, and the definition of the ring A, ar 1、Ar2、L、X、Y、R0、R1、R2、a0、a1、a2 is the same as that described above.
Description of the starting materials, reagents and characterization equipment:
the raw materials and reagent sources used in the following examples are not particularly limited, and may be commercially available products or prepared by methods well known to those skilled in the art.
The mass spectrum uses a Wotes G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer in UK, chloroform as a solvent;
the elemental analysis uses VarioELcube type organic elemental analyzer of Elementar company, germany, and the sample mass is 5-10 mg.
Synthesis example 1 preparation of Compound 3
Preparation of A-3:
To magnesium (4.08 g,168 mmol) was added two pieces of iodine under nitrogen protection, 50mL of anhydrous tetrahydrofuran solvent was further added, then a tetrahydrofuran solution (100 mL) of b-3 (31.52 g,160 mmol) was slowly added dropwise, the reaction was initiated in a format, after the completion of the dropwise addition, the reaction was carried out at room temperature for 7 hours, and after the completion of the reaction, the mixture was cooled to room temperature.
Under the protection of nitrogen, a-3 (29.50 g,160 mmol) is added into a reaction bottle, then 200mL of tetrahydrofuran solvent is added, the system temperature is reduced to-5 ℃, then the format reagent prepared in the step 1 is slowly dripped for 2-3 hours, the reaction is carried out for 6 hours under the condition of-5 ℃ after the dripping is finished, after the reaction is finished, the reaction liquid is poured into 12% dilute hydrochloric acid, after the reaction is fully stirred for 30 minutes, dichloromethane is used for extraction (300 mL multiplied by 3 times), the organic phase is separated, the organic phase is dried by anhydrous magnesium sulfate, the solvent is concentrated by reduced pressure distillation, and the solvent is recrystallized by tetrahydrofuran after suction filtration, thus obtaining an intermediate A-3 (33.21 g, yield 78%) with the HPLC purity of more than or equal to 99.75 percent. Mass spectrum m/z 264.9828 (theory: 264.9810).
Preparation of B-3:
To the reaction flask was added intermediate A-3 (23.42 g,88 mmol), c-3 (10.16 g,80 mmol), anhydrous potassium carbonate (22.11 g,160 mmol) under nitrogen protection, then 200mL of toluene solution was added, and after 3 times of air replacement with nitrogen, tetrakis (triphenylphosphine) palladium (0.92 g,0.8 mmol) was added and the reaction was stirred and heated for 8 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, the solvent was concentrated by distillation under reduced pressure, the filter cake was then washed with ethanol, and the obtained filter cake was recrystallized from toluene to give intermediate B-3 (18.77 g, yield 75%) with HPLC purity ≡ 99.85%. Mass spectrum m/z 312.0839 (theory: 312.0826).
Preparation of compound 3:
b-3 (12.51 g,40 mmol), d-3 (13.57 g,40 mmol), potassium carbonate (11.06 g,80 mmol) and then 150mL of toluene/ethanol/water mixed solvent (toluene: ethanol: water volume ratio=2:1:1) were added under nitrogen protection, palladium acetate (0.18 g,0.8 mmol) was then added after 3 times of nitrogen replacement, xphos (0.76 g,1.6 mmol) was added after the reaction was completed, the reaction was cooled to room temperature, distilled water was added, the mixture was left to stand for separation, the separated organic phase was concentrated by distillation under reduced pressure, the filter cake was washed with ethanol and distilled water, and the obtained filter cake was recrystallized with toluene to give compound 3 (16.46 g, 72%) with HPLC purity > 99.99%, mass spectrum m/z:571.2043 (theoretical value: 571.2057). Theoretical element content (%) C 38H17D5N4O2:C, 79.84, H,4.76, N,9.80. Measured element contents (%) are C,79.87; H,4.74; N,9.82.
Synthesis example 2 preparation of Compound 4
According to the same production method as that of Compound 3 in Synthesis example 1, d-3 was replaced with equimolar d-4, and the other steps were the same, to obtain Compound 4 (16.69 g), and the purity of the solid was not less than 99.98% as measured by HPLC. Mass spectrum m/z 571.2041 (theory: 571.2057). Theoretical element content (%) C 38H17D5N4O2:C, 79.84, H,4.76, N,9.80. The measured element contents (%) were C,79.85, H,4.73, N,9.84.
Synthesis example 3 preparation of Compound 10
According to the same production method as that of Compound 3 in Synthesis example 1, c-3 was replaced with equimolar c-10, and the other steps were the same, to obtain Compound 10 (17.99 g), and the purity of the solid was not less than 99.96% as measured by HPLC. Mass spectrum m/z 651.2635 (theory: 651.2621). Theoretical element content (%) C 44H17D9N4O2:C, 81.08, H,5.41, N,8.60. Measured element contents (%) were C,81.05; H,5.42; N,8.63.
Synthesis example 4 preparation of Compound 28
According to the same production method as that of Compound 3 in Synthesis example 1, c-3 and d-3 were replaced with equimolar amounts of c-28 and d-28, respectively, and the other steps were the same, to give Compound 28 (18.41 g), and the purity of the solid as measured by HPLC was not less than 99.95%. Mass spectrum m/z 676.2586 (theory: 676.2573). Theoretical element content (%) C 45H16D9N5O2:C 79.86, H5.06, N10.35. Measured element contents (%) were C,79.82; H,5.05; N,10.37.
Synthesis example 5 preparation of Compound 93
According to the same production method as that of Compound 3 in Synthesis example 1, b-3 was replaced with equimolar b-93, and the other steps were the same, to obtain Compound 93 (16.93 g), and the purity of the solid was not less than 99.99% as measured by HPLC. Mass spectrum m/z 587.1811 (theory: 587.1828). Theoretical element content (%) C 38H17D5N4 OS: C,77.66; H,4.63; N,9.53. The measured element contents (%) are C,77.68, H,4.64, N,9.52.
Synthesis example 6 preparation of Compound 100
According to the same manner as in Compound 3 of Synthesis example 1, A-3, c-3 and d-3 were replaced with equimolar amounts of A-93, c-100 and d-4, respectively, and the other steps were the same, to obtain Compound 100 (19.10 g), and the purity of the solid was not less than 99.94% as measured by HPLC. Mass spectrum m/z 712.2249 (theory: 712.2235). Theoretical element content (%) C 48H24D4N4 OS: C,80.87; H,4.52; N,7.86. The measured element contents (%) were C,80.85; H,4.53; N,7.83.
Synthesis example 7 preparation of Compound 102
According to the same manner as in Compound 3 of Synthesis example 1 except that b-3, c-3 and d-3 were replaced with equimolar amounts of b-102, c-102 and d-4, respectively, compound 102 (18.82 g) was obtained, and the purity of the solid was not less than 99.95% as measured by HPLC. Mass spectrum m/z 691.2381 (theory: 691.2392). Theoretical element content (%) C 46H17D9N4 OS: C,79.86; H,5.10; N,8.10. The measured element contents (%) were C,79.85; H,5.13; N,8.13.
Synthesis example 8 preparation of Compound 138
According to the same production method as that of Compound 3 in Synthesis example 1, b-3 was replaced with b-138 in equimolar amounts, and the other steps were the same, to obtain Compound 138 (17.66 g), and the purity of the solid was not less than 99.98% as measured by HPLC. Mass spectrum m/z 621.2226 (theory: 621.2213). Theoretical element content (%) C 42H19D5N4O2:C, 81.14, H,4.70, N,9.01. Measured element contents (%) were C,81.11; H,4.74; N,9.02.
Synthesis example 9 preparation of Compound 144
According to the same manner as in Compound 3 of Synthesis example 1 except that b-3 and c-3 were replaced with b-144 and c-144, respectively, the procedure was otherwise the same, to give Compound 144 (17.49 g), and the purity of the solid as measured by HPLC was not less than 99.96%. Mass spectrum m/z 633.2232 (theory: 633.2244). Theoretical element content (%) C 43H23D3N4O2:C, 81.50, H,4.61, N,8.84. Measured element contents (%) are C,81.53, H,4.62, N,8.82.
Synthesis example 10 preparation of Compound 147
According to the same manner as in Compound 3 of Synthesis example 1 except that b-3 was replaced with b-147 in equimolar amounts, compound 147 (17.41 g) was obtained in the same manner as in the other steps, and the purity of the solid was not less than 99.97% as measured by HPLC. Mass spectrum m/z 621.2227 (theory: 621.2213). Theoretical element content (%) C 42H19D5N4O2:C, 81.14, H,4.70, N,9.01. Measured element contents (%) were C,81.16; H,4.73; N,9.02.
Synthesis example 11 preparation of Compound 151
According to the same manner as in Compound 3 of Synthesis example 1 except that b-3 was replaced with b-151 in equimolar amounts, compound 151 (17.66 g) was obtained in the same manner as in the other steps, and the purity of the solid was not less than 99.98% as measured by HPLC. Mass spectrum m/z 621.2229 (theory: 621.2213). Theoretical element content (%) C 42H19D5N4O2:C, 81.14, H,4.70, N,9.01. The measured element contents (%) were C,81.16; H,4.71; N,9.02.
Synthesis example 12 preparation of Compound 155
According to the same manner as in Compound 3 of Synthesis example 1, A-3 and c-3 were replaced with equimolar A-151 and c-155, respectively, and the other steps were the same, to obtain Compound 155 (18.95 g), and the purity of the solid was not less than 99.95% as measured by HPLC. Mass spectrum m/z 696.2474 (theory: 696.2463). Theoretical element content (%) C 48H24D4N4O2:C, 82.74, H,4.63, N,8.04. Measured element contents (%) were C,82.75; H,4.66; N,8.03.
Synthesis example 13 preparation of Compound 159
According to the same production method as that of Compound 3 in Synthesis example 1, b-3 and c-3 were replaced with b-159 and c-159 in equimolar amounts, respectively, and the other steps were the same, to obtain Compound 159 (17.21 g), and the purity of the solid was not less than 99.96% as measured by HPLC. Mass spectrum m/z 623.2325 (theory: 623.2339). Theoretical element content (%) C 42H17D7N4O2:C, 80.88, H,5.01, N,8.98. The measured element contents (%) are C,80.85, H,5.03, N,8.96.
Synthesis example 14 preparation of Compound 161
According to the same manner as in Compound 3 of Synthesis example 1, A-3 and c-3 were replaced with equimolar amounts of A-159 and c-161, respectively, and the other steps were the same, to obtain Compound 161 (20.01 g), and the purity of the solid was not less than 99.93% as measured by HPLC. Mass spectrum m/z 757.3448 (theory: 757.3434). Theoretical element content (%) C 52H31D7N4O2:C, 82.40, H,5.98, N,7.39. Measured element contents (%) were C,82.42; H,5.95; N,7.38.
Synthesis example 15 preparation of Compound 164
According to the same manner as in Compound 3 of Synthesis example 1, A-3 and c-3 were replaced with equimolar A-159 and c-164, respectively, and the other steps were the same, to obtain Compound 164 (18.49 g), and the purity of the solid was not less than 99.95% as measured by HPLC. Mass spectrum m/z 679.2977 (theory: 679.2965). Theoretical element content (%) C 46H25D7N4O2:C, 81.27, H,5.78, N,8.24. Measured element contents (%) were C,81.28; H,5.76; N,8.28.
Synthesis example 16 preparation of Compound 165
According to the same production method as that of Compound 3 in Synthesis example 1, b-3 and c-3 were replaced with equimolar amounts of b-165 and c-165, respectively, and the other steps were the same, to obtain Compound 165 (17.91 g), and the purity of the solid as measured by HPLC was not less than 99.96%. Mass spectrum m/z 648.2282 (theory: 648.2291). Theoretical element content (%) C 43H16D7N5O2:C, 79.61, H,4.66, N,10.80. Measured element contents (%) are C,79.62; H,4.63; N,10.84.
Synthesis example 17 preparation of Compound 173
According to the same manner as in Compound 3 of Synthesis example 1 except that A-3 was replaced with equimolar A-159, compound 173 (17.86 g) was obtained in the same manner as in the other steps, and the purity of the solid was not less than 99.98% as measured by HPLC. Mass spectrum m/z 628.2663 (theory: 628.2652). Theoretical element content (%) C 42H12D12N4O2:C, 80.23, H,5.77, N,8.91. Measured element contents (%) are C,80.25, H,5.75, N,8.94.
Synthesis example 18 preparation of Compound 174
According to the same manner as in Compound 3 of Synthesis example 1 except that A-3 and c-3 were replaced with equimolar amounts of A-159 and c-174, respectively, the other steps were the same, to obtain Compound 174 (19.32 g), and the purity of the solid as measured by HPLC was not less than 99.94%. Mass spectrum m/z 720.2871 (theory: 720.2884). Theoretical element content (%) C 48H12D14N4O3:C, 79.98; H,5.59; N,7.77. The measured element contents (%) are C,79.95, H,5.57, N,7.78.
Synthesis example 19 preparation of Compound 175
According to the same manner as in Compound 3 of Synthesis example 1 except that b-3 was replaced with b-175 in equimolar amounts, compound 175 (18.11 g) was obtained in the same manner as in other steps, and the purity of the solid was not less than 99.98% as measured by HPLC. Mass spectrum m/z 637.1971 (theory: 637.1985). Theoretical element content (%) C 42H19D5N4 OS: C,79.10; H,4.58; N,8.78. The measured element contents (%) are C,79.12, H,4.55, N,8.76.
Synthesis example 20 preparation of Compound 188
According to the same production method as that of Compound 3 in Synthesis example 1, b-3 and c-3 were replaced with equimolar amounts of b-188 and c-188, respectively, and the other steps were the same, to obtain Compound 188 (20.48 g), and the purity of the solid was not less than 99.91% as measured by HPLC. Mass spectrum m/z 799.3346 (theory: 799.3359). Theoretical element content (%) C 57H33D5N4 O: C,85.58; H,5.42; N,7.00. The measured element contents (%) are C,85.56; H,5.45; N,7.03.
Synthesis example 21 preparation of Compound 199
Preparation of d-199:
To the reaction flask was added e-199 (29.70 g,70 mmol), pinacol ester of diboronic acid (18.66 g,73.5 mmol), KOAc (20.61 g,210 mmol), then 300mL1, 4-dioxane, 3 times replaced with nitrogen, pd (dppf) Cl 2 (0.59 g,0.8 mmol), stirred at 90℃for 5 hours, cooled to room temperature after completion of the reaction, distilled water was added, extracted with ethyl acetate (500 mL. Times.3), the organic phase was separated, dried over anhydrous magnesium sulfate, and the resulting solid was purified with hexane: EA=7:1 (v/v) to give d-199 (27.06 g, 82%), HPLC purity +.99.84%, mass spectrum m/z:471.2017 (theoretical value: 471.2006).
According to the same manner as in Compound 3 of Synthesis example 1 except that b-3 and d-3 were replaced with equimolar amounts of b-199 and d-199, respectively, the other steps were the same, to give Compound 199 (19.72 g), and the purity of the solid as measured by HPLC was not less than 99.93%. Mass spectrum m/z 746.2859 (theory: 746.2842). Theoretical element content (%) C 52H26D5N5 O: C,83.62; H,4.86; N,9.38. Measured element contents (%) are C,83.63; H,4.84; N,9.36.
Synthesis example 22 preparation of Compound 207
According to the same manner as that of Compound 3 in Synthesis example 1 except that b-3 was replaced with b-207 in equimolar amounts, compound 207 (18.54 g) was obtained in the same manner, and the purity of the solid was not less than 99.96% as measured by HPLC. Mass spectrum m/z 671.2385 (theory: 671.2370). Theoretical element content (%) C 46H21D5N4O2:C, 82.25, H,4.65, N,8.34. Measured element contents (%) are C,82.23, H,4.66, N,8.32.
Synthesis example 23 preparation of Compound 216
Preparation of e-216:
To the reaction flask, f-216 (28.69 g,100 mmol), d-3 (33.92 g,100 mmol), potassium carbonate (27.64 g,200 mmol) and then 350mL of toluene/ethanol/water mixed solvent (toluene: ethanol: water volume ratio=2:1:1) were added under nitrogen protection, then tetrakis (triphenylphosphine) palladium (0.12 g,0.10 mmol) was added to react for 4 hours under stirring and refluxing, after completion of the reaction, the reaction was cooled to room temperature, distilled water was added, and the mixture was left to stand for separation, the separated organic phase was concentrated by distillation under reduced pressure, the solvent was suction filtered, the filter cake was washed with ethanol, and the obtained filter cake was recrystallized with toluene to give e-216 (38.62 g, 85%), HPLC purity of > 99.81%, mass spectrum m/z:453.0651 (theoretical value: 453.0666).
Preparation d-216:
To the reaction flask was added e-216 (31.81 g,70 mmol), pinacol ester of diboronic acid (18.66 g,73.5 mmol), KOAc (20.61 g,210 mmol), then 300mL1, 4-dioxane, 3 times replaced by nitrogen, pd (dppf) Cl 2 (0.59 g,0.8 mmol), stirred at 90℃for 6 hours, cooled to room temperature after the end of the reaction, distilled water was added, extracted with ethyl acetate (500 mL. Times.3), the organic phase was separated, dried over anhydrous magnesium sulfate and the resulting solid was purified with hexane: EA=7:1 (v/v) to give d-216 (29.13 g, 83%), HPLC purity +.99.84%, mass spectrum m/z:501.2427 (theoretical value: 501.2413).
According to the same manner as in Compound 3 of Synthesis example 1, c-3 and d-3 were replaced with equimolar amounts of c-159 and d-216, respectively, and the other steps were the same, to obtain Compound 216 (18.37 g), and the purity of the solid was not less than 99.98% as measured by HPLC. Mass spectrum m/z 646.2323 (theory: 646.2307). Theoretical element content (%) C 44H22D4N4O2:C, 81.71, H,4.67, N,8.66. Measured element contents (%) were C,81.74; H,4.65; N,8.67.
Synthesis example 24 preparation of Compound 229
According to the same manner as that of compound 216 in Synthesis example 23, f-216 and d-216 were replaced with equimolar amounts of f-229 and d-229, respectively, and the other steps were the same, to obtain compound 229 (19.01 g), and the purity of the solid was not less than 99.95% as measured by HPLC. Mass spectrum m/z 698.2577 (theory: 698.2589). Theoretical element content (%) C 48H22D6N4O2:C, 82.50, H,4.90, N,8.02. The measured element contents (%) were C,82.52; H,4.93; N,8.01.
Synthesis example 25 preparation of Compound 237
According to the same manner as that of compound 216 in Synthesis example 23 except that f-216, B-216 and d-216 were replaced with equimolar amounts of f-237, B-3 and d-237, respectively, the other steps were the same, compound 237 (18.25 g) was obtained, and the purity of the solid as measured by HPLC was not less than 99.97%. Mass spectrum m/z 651.2638 (theory: 651.2621). Theoretical element content (%) C 44H17D9N4O2:C, 81.08, H,5.41, N,8.60. Measured element contents (%) are C,81.06; H,5.45; N,8.63.
Synthesis example 26 preparation of Compound 290
According to the same manner as in Compound 3 of Synthesis example 1, A-3, c-3 and d-3 were replaced with equimolar amounts of A-151, c-290 and d-290, respectively, and the other steps were the same, to give Compound 290 (19.80 g), and the purity of the solid was not less than 99.93% as measured by HPLC. Mass spectrum m/z 749.2822 (theory: 749.2808). Theoretical element content (%) C 52H23D7N4O2:C, 83.29, H,4.97, N,7.47. The measured element contents (%) were C,83.28; H,4.95; N,7.46.
Synthesis example 27 preparation of Compound 295
Preparation of g-295:
H-295 (52.39 g,140 mmol), pinacol ester of diboronic acid (37.33 g,147 mmol), KOAc (41.22 g,420 mmol) and then 600mL1, 4-dioxane were added under nitrogen, after 3 air substitutions, pd (dppf) Cl 2 (1.17 g,1.6 mmol) was added, the reaction was stirred at 90℃for 6.5 hours, after the end of the reaction was cooled to room temperature, distilled water was added, then extracted with ethyl acetate (500 mL. Times.3), the organic phase was separated, dried over anhydrous magnesium sulfate and the resulting solid was purified with hexane: EA=7:1 (v/v) to give g-295 (50.72 g, 86%), HPLC purity.
According to the same manner as that for the preparation of compound 216 in Synthesis example 23, f-216, d-3, A-3 and d-216 were replaced with equimolar amounts of f-237, g-295, A-175 and d-295, respectively, and the other steps were the same, to obtain compound 295 (19.10 g), and the purity of the solid as measured by HPLC was not less than 99.94%. Mass spectrum m/z 712.2247 (theory: 712.2235). Theoretical element content (%) C 48H24D4N4 OS: C,80.87; H,4.52; N,7.86. Measured element contents (%) are C,80.86, H,4.54, N,7.88.
Synthesis example 28 preparation of Compound 311
According to the same manner as in Compound 3 of Synthesis example 1 except that d-3 was replaced with d-311 in equimolar amounts, compound 311 (16.93 g) was obtained in the same manner as in other steps, and the purity of the solid was not less than 99.99% as measured by HPLC. Mass spectrum m/z 587.1815 (theory: 587.1828). Theoretical element content (%) C 38H17D5N4 OS: C,77.66; H,4.63; N,9.53. The measured element contents (%) are C,77.68, H,4.64, N,9.55.
Synthesis example 29 preparation of Compound 334
According to the same manner as in Compound 3 of Synthesis example 1 except that b-3 and d-3 were replaced with equimolar amounts of b-334 and d-311, respectively, the other steps were the same, to give Compound 334 (18.11 g), and the purity of the solid as measured by HPLC was not less than 99.98%. Mass spectrum m/z 637.1974 (theory: 637.1985). Theoretical element content (%) C 42H19D5N4 OS: C,79.10; H,4.58; N,8.78. The measured element contents (%) are C,79.12, H,4.55, N,8.76.
Synthesis example 30 preparation of Compound 394
According to the same manner as in Compound 3 of Synthesis example 1, A-3, c-3 and d-3 were replaced with equimolar amounts of A-147, c-394 and d-311, respectively, and the other steps were the same, to give Compound 394 (19.10 g), the purity of the solid was not less than 99.94% as measured by HPLC. Mass spectrum m/z 712.2223 (theory: 712.2235). Theoretical element content (%) C 48H24D4N4 OS: C,80.87; H,4.52; N,7.86. The measured element contents (%) are C,80.86, H,4.54, N,7.87.
Synthesis example 31 preparation of Compound 405
According to the same manner as in Compound 3 of Synthesis example 1 except that B-3 and d-3 were replaced with equimolar amounts of B-175 and d-311, respectively, the other steps were the same, to give Compound 405 (18.05 g), and the purity of the solid as measured by HPLC was not less than 99.96%. Mass spectrum m/z 653.1742 (theory: 653.1756). Theoretical element content (%) C 42H19D5N4S2:C, 77.15, H,4.47, N,8.57. The measured element contents (%) are C,77.16, H,4.49 and N,8.55.
Synthesis example 32 preparation of Compound 429
According to the same manner as that of compound 216 in Synthesis example 23 except that f-216, d-3, b-3, c-159 and d-216 were replaced with equimolar amounts of f-429, d-311, b-429, c-429 and d-429 respectively, the other steps were the same, to obtain compound 429 (20.36 g), and the purity of the solid as measured by HPLC was not less than 99.92%. Mass spectrum m/z 782.2968 (theory: 782.2955). Theoretical element content (%) C 53H26D8N4 OS: C,81.30; H,5.41; N,7.16. The measured element contents (%) were C,81.33, H,5.42, N,7.15.
Synthesis example 33 preparation of Compound 454
According to the same manner as that of compound 216 in Synthesis example 23, f-216, d-3, B-216 and d-216 were replaced with equimolar amounts of f-237, d-311, B-295 and d-454, respectively, and the other steps were the same, to obtain compound 454 (19.54 g), and the purity of the solid as measured by HPLC was not less than 99.94%. Mass spectrum m/z 728.2021 (theory: 728.2006). Theoretical element content (%) C 48H24D4N4S2:C, 79.09; H,4.42; N,7.69. Measured element contents (%) are C,79.08; H,4.45; N,7.65.
Synthesis example 34 preparation of Compound 461
According to the same manner as that of Compound 216 in Synthesis example 23 except that e-216, B-216 and d-216 were replaced with equimolar amounts of e-461, B-3 and d-461, respectively, compound 461 (17.19 g) was obtained, and the purity of the solid was not less than 99.99% as measured by HPLC. Mass spectrum m/z 596.2361 (theory: 596.2373). Theoretical element content (%) C 40H20D5N5 O: C,80.52; H,5.07; N,11.74. The measured element contents (%) are C,80.54, H,5.04, N,11.72.
Synthesis example 35 preparation of Compound 510
According to the same manner as that of compound 216 in Synthesis example 23 except that e-216, a-3, b-3, c-159 and d-216 were replaced with equimolar amounts of e-510, a-510, b-510, c-3 and d-510, respectively, the other steps were the same, to obtain compound 510 (17.12 g), and the purity of the solid as measured by HPLC was not less than 99.98%. Mass spectrum m/z 602.1633 (theory: 602.1647). Theoretical element content (%) C 39H18D5N3S2:C, 77.71, H,4.68, N,6.97. Measured element contents (%) are C,77.72; H,4.65; N,6.96.
Synthesis example 36 preparation of Compound 531
According to the same manner as in Compound 3 of Synthesis example 1 except that a-3, b-3 and d-3 were replaced with equimolar amounts of a-531, b-531 and d-311, respectively, the other steps were the same, compound 531 (17.55 g) was obtained, and the purity of the solid was not less than 99.96% as measured by HPLC. Mass spectrum m/z 635.2096 (theory: 635.2080). Theoretical element content (%) C 44H21D5N2 OS: C,83.12; H,4.91; N,4.41. Measured element contents (%) are C,83.15, H,4.92, N,4.43.
Device example 1
The glass substrate was washed with distilled water and ultrasonic waves. After the distilled water washing is completed, ultrasonic washing is performed with a solvent such as isopropyl alcohol, acetone, methanol, etc., and drying is performed. An anode is formed of Indium Tin Oxide (ITO) on the substrate on which the reflective layer is formed. Vacuum evaporating compound HI on anode to obtain a film with a thickness ofA Hole Injection Layer (HIL). Evaporating a compound HT on the hole injection layer to form a film with a thickness ofIs provided. Evaporating compound EB on the hole transport layer to form a film with a thickness ofIs a barrier to electrons. On the electron blocking layer, the compound 3 and the compound H-1 are mixed in a weight ratio of 60 percent to 40 percent to form a mixed body, and the mixed body and the dopant Ir (piq) 2 (acac) are formed into a thickness by co-vacuum evaporation according to an evaporation rate ratio of 94 percent to 6 percentIs an emission layer (EML). Evaporating a compound HB on the light-emitting layer to form a film having a thickness ofIs a hole blocking layer of (a). On the hole blocking layer, the compounds ET and LiQ are mixed in a weight ratio of 50% to 50% and evaporated to a thicknessElectron Transport Layer (ETL). Vapor deposition of LiF on electron transport layer to a thickness ofElectron Injection Layer (EIL). Mixing magnesium (Mg) and silver (Ag) on the electron injection layer at a vapor deposition rate of 1:9, and vacuum evaporating to obtain a film with a thickness ofIs provided. Evaporating CP on cathode to form a film with a thickness ofIs an organic Coating (CPL). Thereby completing the manufacture of the organic light emitting device.
Device examples 2 to 36
An organic electroluminescent device was produced by the same production method as in device example 1, except that compound 3 in device example 1 was replaced with compound 4, compound 10, compound 28, compound 93, compound 100, compound 102, compound 138, compound 144, compound 147, compound 151, compound 155, compound 159, compound 161, compound 164, compound 165, compound 173, compound 174, compound 175, compound 188, compound 199, compound 207, compound 216, compound 229, compound 237, compound 290, compound 295, compound 311, compound 334, compound 394, compound 405, compound 429, compound 454, compound 461, compound 510 and compound 531, respectively, as a host material for the light-emitting layer.
Comparative device examples 1 to 5
An organic electroluminescent device was produced by the same production method as in device example 1, except that compound H-2, compound H-3, compound H-4, compound H-5, and compound H-6 were used as the host material of the light-emitting layer in place of compound 3 in device example 1, respectively.
Test software, a computer, a K2400 digital source list manufactured by Keithley company, U.S. and a PR788 spectral scanning luminance meter manufactured by PhotoResearch company, U.S. are combined into a combined IVL test system to test the luminous efficiency of the organic electroluminescent device. Life testing an M6000OLED life test system from MCSCIENCE was used.
The environment tested was atmospheric and the temperature was room temperature. The results of testing the light emitting characteristics of the devices 1 to 36 in the device examples according to the present invention and the organic electroluminescent devices obtained in the comparative examples 1 to 5 are shown in the following table 1.
Table 1:
As can be seen from the results in Table 1, when the heterocyclic compound of the present invention is applied to the host material of the light-emitting layer of the organic electroluminescent device, the device has higher light-emitting efficiency and longer service life, and the compound of the present invention is a host material of the light-emitting layer with good performance.
Device example 37
The glass substrate was washed with distilled water and ultrasonic waves. After the distilled water washing is completed, ultrasonic washing is performed with a solvent such as isopropyl alcohol, acetone, methanol, etc., and drying is performed. An anode is formed of Indium Tin Oxide (ITO) on the substrate on which the reflective layer is formed. Vacuum evaporating HI-2 on anode to obtain a film with a thickness ofA Hole Injection Layer (HIL). Evaporating compound HT-2 on the hole injection layer to form a film with a thickness ofIs provided. Evaporating compound EB on the hole transport layer to form a film with a thickness ofIs a barrier to electrons. On the electron blocking layer, the compound H-7 and the dopant Ir (ppy) 2 (acac) are formed into a thickness by co-vacuum evaporation according to the evaporation rate ratio of 95 percent to 5 percentIs an emission layer (EML). Evaporating compound HB-2 on the light-emitting layer to form a film with a thickness ofIs a hole blocking layer of (a). Evaporating the compound 3 of the present invention on the hole blocking layer to form a film of a thickness ofElectron Transport Layer (ETL). Vapor deposition of LiF on electron transport layer to a thickness ofElectron Injection Layer (EIL). Mixing magnesium (Mg) and silver (Ag) on the electron injection layer at a vapor deposition rate of 1:9, and vacuum evaporating to obtain a film with a thickness ofIs provided. Thereby completing the manufacture of the organic light emitting device.
Device examples 38 to 72
An organic electroluminescent device was produced by the same production method as in device example 37, except that compound 3 in device example 37 was replaced with compound 4, compound 10, compound 28, compound 93, compound 100, compound 102, compound 138, compound 144, compound 147, compound 151, compound 155, compound 159, compound 161, compound 164, compound 165, compound 173, compound 174, compound 175, compound 188, compound 199, compound 207, compound 216, compound 229, compound 237, compound 290, compound 295, compound 311, compound 334, compound 394, compound 405, compound 429, compound 454, compound 461, compound 510 and compound 531, respectively, as an electron transporting material.
Comparative device examples 6 to 10
An organic electroluminescent device was produced by the same production method as in device example 37, except that compound H-2, compound H-3, compound H-4, compound H-5 and compound H-6 were used as electron transporting materials in place of compound 3 in device example 37, respectively.
Test software, a computer, a K2400 digital source list manufactured by Keithley company, U.S. and a PR788 spectral scanning luminance meter manufactured by PhotoResearch company, U.S. are combined into a combined IVL test system to test the luminous efficiency of the organic electroluminescent device. Life testing an M6000OLED life test system from MCSCIENCE was used.
The environment tested was atmospheric and the temperature was room temperature. The results of testing the light emitting characteristics of the devices 37 to 72 in the device examples according to the present invention and the organic electroluminescent devices obtained in comparative examples 6 to 10 are shown in table 2 below.
Table 2:
As can be seen from the results of table 2, when the heterocyclic compound of the present invention is applied to the electron transport layer material of the organic electroluminescent device, the device has higher luminous efficiency and longer service life, and the compound of the present invention is an electron transport layer material with good performance.
Device example 73]
The glass substrate was washed with distilled water and ultrasonic waves. After the distilled water washing is completed, ultrasonic washing is performed with a solvent such as isopropyl alcohol, acetone, methanol, etc., and drying is performed. An anode is formed of Indium Tin Oxide (ITO) on the substrate on which the reflective layer is formed. Vacuum evaporating HI-3 on anode to form a film with a thickness ofA Hole Injection Layer (HIL). Evaporating compound HT-3 on the hole injection layer to form a film with a thickness ofIs provided. Evaporating compound EB on the hole transport layer to form a film with a thickness ofIs a barrier to electrons. On the electron blocking layer, the compound H-8 and the dopant Ir (ppy) 3 are formed into a thickness by co-vacuum evaporation according to the evaporation rate ratio of 93 percent to 7 percentIs an emission layer (EML). Evaporating the compound 3 of the present invention on the light-emitting layer to form a film having a thickness ofIs a hole blocking layer of (a). On the hole blocking layer, the compounds ET and LiQ are mixed in a weight ratio of 50% to 50% and evaporated to a thicknessElectron Transport Layer (ETL). Vapor deposition of LiF on electron transport layer to a thickness ofElectron Injection Layer (EIL). Mixing magnesium (Mg) and silver (Ag) on the electron injection layer at a vapor deposition rate of 1:9, and vacuum evaporating to obtain a film with a thickness ofIs provided. Thereby completing the manufacture of the organic light emitting device.
Device examples 74 to 108
An organic electroluminescent device was produced by the same production method as in device example 73, except that compound 3 in device example 73 was replaced with compound 4, compound 10, compound 28, compound 93, compound 100, compound 102, compound 138, compound 144, compound 147, compound 151, compound 155, compound 159, compound 161, compound 164, compound 165, compound 173, compound 174, compound 175, compound 188, compound 199, compound 207, compound 216, compound 229, compound 237, compound 290, compound 295, compound 311, compound 334, compound 394, compound 405, compound 429, compound 454, compound 461, compound 510 and compound 531, respectively, as a hole blocking material.
Comparative device examples 11 to 15
An organic electroluminescent device was produced by the same production method as in device example 73, except that compound H-2, compound H-3, compound H-4, compound H-5 and compound H-6 were used as hole blocking materials in place of compound 3 in device example 73, respectively.
Test software, a computer, a K2400 digital source list manufactured by Keithley company, U.S. and a PR788 spectral scanning luminance meter manufactured by PhotoResearch company, U.S. are combined into a combined IVL test system to test the luminous efficiency of the organic electroluminescent device. Life testing an M6000OLED life test system from MCSCIENCE was used.
The environment tested was atmospheric and the temperature was room temperature. The results of the light emitting characteristics of devices 73 to 108 in the device examples of the present invention and the organic electroluminescent devices obtained in comparative examples 11 to 15 are shown in the following table 3.
Table 3:
As can be seen from the results in Table 3, when the heterocyclic compound of the present invention is applied to a hole blocking layer material of an organic electroluminescent device, the device has higher luminous efficiency and longer service life, and the compound of the present invention is a hole blocking layer material with good performance.
It should be noted that while the present invention has been specifically described with reference to individual embodiments, it will be apparent to those skilled in the art that numerous modifications and variations can be made without departing from the principles of the present invention, and such modifications and variations fall within the scope of the present invention.

Claims (9)

1. A heterocyclic compound, wherein the heterocyclic compound is selected from any one of the following structures:
Wherein, each structure has 0V selected from N atoms or 1V selected from N atoms;
Y is selected from any one of O, S;
R p is independently selected from any one of unsubstituted C6-C12 aryl;
Said R q、Rr is independently selected from hydrogen;
The g 2 is selected from 0,1, 2,3, 4, 5, 6, 7 or 8, the g 3 is selected from 0,1, 2,3, 4 or 5, and the g 4 is selected from 0,1, 2,3, 4, 5, 6 or 7;
The h 1 is selected from 0, 1, 2, 3, or 4;
The said Selected from any one of the following structures:
the R 2 is selected from hydrogen;
Said a 21 is selected from 1, said a 2 is selected from 2;
Ar 1 is selected from any one of the formulas II and III;
The formula II is selected from any one of the following structures:
The R 9 is selected from hydrogen;
The f 1 is selected from 1, 2, 3, 4 or 5, the f 2 is selected from 1, 2, 3, 4, 5, 6 or 7, and the formula III is selected from any one of the following structures:
R 5 is selected from any one of hydrogen and deuterium;
R a、Rb is independently selected from any one of unsubstituted C1-C6 alkyl and unsubstituted phenyl;
R c is selected from any one of unsubstituted C6-C12 aryl;
Said b 1 is selected from 5, said b 2 is selected from 7, said b 3 is selected from 9, said b 6 is selected from 4, said b 8 is selected from 6, said b 9 is selected from 3, when two or more R 5 are present, two or more R 5 are identical to each other;
Ar 2 is selected from any one of a formula II, a formula III and a structure shown as the following:
R 8 is the same and is selected from any one of hydrogen and deuterium;
R 8a is the same or different and is selected from any one of hydrogen, cyano, unsubstituted C1-C6 alkyl and unsubstituted C3-C10 cycloalkyl;
the R 8b is selected from deuterium;
the R 8c is selected from hydrogen;
Said e 1 is selected from 5, said e 2 is selected from 4, said e 6 is selected from 7, said e 8 is selected from 9, said e 10 is selected from 11, said e 12 is selected from 13, and when two or more R 8 are present, two or more R 8 are identical to each other;
The e 1a is selected from 0, 1,2,3, 4 or 5, when two or more R 8a are present, two or more R 8a are the same or different from each other;
the L is selected from a single bond or any one of the following structures:
;
provided that at least one of Ar 1、Ar2, L is selected from those containing deuterium in the foregoing groups.
2. The heterocyclic compound according to claim 1, wherein the heterocyclic compound is selected from any one of the following structures:
And V is selected from any one of CH and N.
3. The heterocyclic compound according to claim 1, wherein said formula II is selected from any one of the following structures:
。
4. The heterocyclic compound according to claim 1, wherein the formula III is selected from any one of the following structures:
r a、Rb is independently selected from any one of unsubstituted C1-C6 alkyl.
5. The heterocyclic compound according to claim 1, wherein L is selected from a single bond or from any one of the following structures:
。
6. The heterocyclic compound according to claim 1, wherein when Ar 2 is not represented by formula II or formula III, it is selected from any one of the following structures:
R 8 is the same and is selected from any one of hydrogen and deuterium;
the R 8a is selected from hydrogen;
the R 8b is selected from deuterium.
7. A heterocyclic compound, characterized in that the compound is selected from any one of the following structures:
。
8. An organic electroluminescent device comprising an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer comprises at least one of the heterocyclic compounds according to any one of claims 1 to 7.
9. The organic electroluminescent device according to claim 8, wherein the organic layer comprises at least one of an electron transport layer and a hole blocking layer, and wherein the at least one of an electron transport layer and a hole blocking layer comprises at least one of the heterocyclic compounds according to any one of claims 1 to 7.
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