CN117164567A - Carbazole-containing triarylamine compound and organic electroluminescent device thereof - Google Patents

Carbazole-containing triarylamine compound and organic electroluminescent device thereof Download PDF

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CN117164567A
CN117164567A CN202311118192.1A CN202311118192A CN117164567A CN 117164567 A CN117164567 A CN 117164567A CN 202311118192 A CN202311118192 A CN 202311118192A CN 117164567 A CN117164567 A CN 117164567A
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ring
integer selected
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孙敬
韩春雪
杜明珠
周雯庭
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Changchun Hyperions Technology Co Ltd
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Changchun Hyperions Technology Co Ltd
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Abstract

The invention provides a carbazole-containing triarylamine compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The carbazole-containing triarylamine compound shown in the formula 1 has good hole mobility, good stability and matched energy level, is used as a hole transport material in an organic electroluminescent device, has excellent performance, particularly has low driving voltage, high luminous efficiency and long service life, and is an organic electroluminescent material with good performance.

Description

Carbazole-containing triarylamine compound and organic electroluminescent device thereof
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a carbazole-containing triarylamine compound and an organic electroluminescent device thereof.
Background
Organic electroluminescent diodes (Organic Light Emitting Diode, OLEDs), also known as organic electroluminescent devices, have more excellent characteristics than other display technologies, such as self-luminescence, fast response speed, low power consumption, wide viewing angle, high resolution, high contrast ratio, ultra thin and ultra light, flexible display, etc. Based on the above advantages, OLEDs are widely used in cell phones, computers, televisions, smart wearable devices, virtual Reality (VR), vehicle displays, and the like.
The OLED mostly adopts a sandwich structure of a sandwich type, that is, an organic functional layer is sandwiched between an anode and a cathode at both sides of the device. OLED structures range from initial single-layer device structures to multi-layer device structures, from simple host-to-host-guest light-emitting structures, and OLED structures, although becoming more complex, the function of each layer is becoming more and more well defined. When a current is applied, the cathode injects electrons and the anode injects holes. The electrons and holes will move toward each other through the layers and eventually meet and combine at the light emitting layer, releasing energy in the form of photons.
The organic functional layers in an OLED mainly include: a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a capping layer, and the like. Among them, the hole transport layer occupies an important position in the OLED, and its basic role is to improve the hole transport efficiency in the device.
However, most of the hole transport materials currently used have large defects, which cause problems of increased driving voltage, reduced luminous efficiency, reduced service life and the like of the OLED. Therefore, the development of a hole transport material with better performance is an important point of research.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a triarylamine compound containing carbazole and an organic electroluminescent device thereof.
The invention provides a carbazole-containing triarylamine compound represented by the following formula 1,
ar is selected from the group represented by formula 1-a,
said X is selected from O, S, N (R) x ) Or C (R) x ) 2 The R is x The same or different one selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring condensed ring groups;
the ring A is selected from one of a substituted or unsubstituted 6-30 membered aromatic ring and a substituted or unsubstituted 6-30 membered nitrogen-containing heteroaromatic ring, and the ring A is not substituted or unsubstituted
The m is 1 An integer selected from 0 to 2, said R 1 The same or different radicals are selected from hydrogen, deuterium, tritium, cyano, F, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and are taken One of substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring condensed ring group, or two adjacent R 1 Bonded to each other to form a substituted or unsubstituted ring;
the Ar is as follows 1 、Ar 2 Independently selected from one or a combination of the groups shown in the formula 1-a,
said e 1 An integer selected from 0 to 5, said e 2 An integer selected from 0 to 4, each R 2 、R 20 The same or different is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and condensed ring group of C6-C30 aromatic ring, or adjacent two R 2 Two adjacent R 20 Bonded to each other to form a substituted or unsubstituted ring;
the R is 0 The same or different is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and condensed ring group of C6-C30 aromatic ring, or adjacent two R 0 Bonded to each other to form a substituted or unsubstituted ring;
the E is selected from N or CH and at least contains one N;
the L is 1 、L 2 、L 3 、L 4 Independently selected from one of single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C2-C30, substituted or unsubstituted alicyclic of C3-C20 and condensed ring group of arylene of C6-C30;
said n 1 An integer selected from 0 to 3, said n 2 An integer selected from 0 to 4, wherein R is the same or different and is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring condensed ring groups, or two adjacent R are bonded with each other to form a substituted or unsubstituted ring.
In addition, the invention also provides an organic electroluminescent device, which contains the carbazole-containing triarylamine compound.
The beneficial effects are that: the carbazole-containing triarylamine compound shown in the formula 1 has good hole mobility, good stability and matched energy level, is used as a hole transport material in an organic electroluminescent device, has excellent performance, particularly has low driving voltage, high luminous efficiency and long service life, and is an organic electroluminescent material with good performance.
Detailed Description
The present application is further illustrated below in conjunction with specific embodiments, it being understood that these embodiments are meant to be illustrative of the application and not limiting the scope of the application, and that modifications of the application, which are all equivalent to those skilled in the art to which the application pertains, are within the scope of the application as claimed.
In the compounds of the present specification, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes atoms in both its natural isotopic abundance and non-natural abundance. In the present application, "H", "hydrogen" and "hydrogen atom" refer to isotopes having different neutron numbers, including protium, deuterium and tritium.
In the present specification, the halogen includes fluorine, chlorine, bromine and iodine.
In the present specification, when the position of the substituent on the ring is not fixed,meaning that it can be attached to any of the corresponding selectable positions of the loop. For example, the number of the cells to be processed,can indicate->Can representCan represent And so on.
In this specification, "adjacent two groups are bonded to form a ring" means that a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring is formed by adjacent groups binding to each other and optionally aromatizing. The hydrocarbon ring may be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle may include aliphatic or aromatic heterocycles. The aliphatic hydrocarbon ring may be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocyclic ring may be a saturated aliphatic heterocyclic ring or an unsaturated aliphatic heterocyclic ring. The hydrocarbon ring and the heterocyclic ring may be a single ring or a polycyclic group. In addition, a ring formed by bonding adjacent groups may be linked to another ring to form a spiro structure. As exemplified below:
In the present specification, the ring formed by the connection may be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, an eight-membered ring, a condensed ring, or the like, for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornane, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, or the like, but is not limited thereto.
In the present specification, the term "integer selected from 0 to M" means any one of the integers selected from 0 to M, and includes 0,1,2 … M-2, M-1, M. For example, the term "n1 is an integer of 0 to 3" means that n1 is 0,1,2 or 3. And so on.
In the present specification, "unsubstituted ZZ group" in the "substituted or unsubstituted ZZ group" means that a hydrogen atom of the "ZZ group" is not substituted with a substituent. For example, "unsubstituted aryl" in "substituted or unsubstituted C6-C60 aryl" means that the hydrogen atom of the "aryl" is not replaced by a substituent. And so on.
In the present specification, "CXX to CYY" in the "substituted or unsubstituted CXX to CYY ZZ group" means the number of carbon atoms in the unsubstituted "ZZ group", and when the "ZZ group" has a substituent, the number of carbon atoms of the substituent is not included. For example, "C6 to C60" in the "substituted or unsubstituted C6 to C60 aryl" represents the number of carbon atoms in the unsubstituted "aryl", and when the "aryl" has a substituent, the number of carbon atoms in the substituent is not included. And so on.
In the present specification, "substitution" in the "substituted or unsubstituted" means that at least one hydrogen atom on a 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 position of the hydrogen substituted with the substituent may be any position. The substituents represented by "substitution" in the above "substituted or unsubstituted" include the following groups, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted heterocyclic group of C3 to C15, substituted or unsubstituted alkyl group of C1 to C15, substituted or unsubstituted cycloalkyl group of C3 to C15, substituted or unsubstituted aryl group of C6 to C20, substituted or unsubstituted heteroaryl group of C2 to C20, fused ring group of substituted or unsubstituted alicyclic ring of C3 to C15 and aromatic ring of C6 to C20, fused ring group of substituted or unsubstituted alicyclic ring of C3 to C15 and heteroaromatic ring of C2 to C20, and the like. The following groups are preferred:deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, camphene, isobornyl, fenchyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylyl, anthracenyl, pyrenyl, A group, a fluoranthenyl group, a benzocyclopropanyl group, a benzocyclobutanyl group, a indanyl group, a tetrahydronaphthyl group, a benzocycloheptanyl group, a benzocyclobutenyl group, an indenyl group, a dihydronaphthyl group, a fluorenyl group, a benzofluorenyl group, a spirobifluorenyl group, a benzofuranyl group, a pyridofuranyl group, a naphthofuranyl group, a dibenzofuranyl group, a benzothienyl group, a pyridothienyl group, a naphthothienyl group, a dibenzothienyl group, an indolyl group, a carbazolyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and the like. Further, each of the above substituents may be substituted or unsubstituted. Two adjacent substituents may be bonded to form a ring.
In the present specification, the "silyl group" means-Si (R g ) 3 A group wherein each R g The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic rings. Preferably, each R g The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstitutedCyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocyclopropanyl, and the like. Examples may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethylt-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, terphenylsilyl, tripyridylsilyl, and the like, but are not limited thereto.
In the present specification, the alkyl group refers to a hydrocarbon group in which one hydrogen atom is omitted from an alkane molecule, and the alkyl group includes a linear alkyl group and a branched alkyl group. Chain alkyl groups containing three or more carbon atoms include isomers thereof, such as propyl groups including n-propyl, isopropyl, butyl groups including n-butyl, sec-butyl, isobutyl, and tert-butyl, and so forth. Examples of the alkyl group may include, but are not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, and the like. The number of carbon atoms of the alkyl group is 1 to 20, preferably 1 to 15, and more preferably 1 to 10.
In the present specification, the cycloalkyl group refers to a hydrocarbon group in which one hydrogen atom is omitted from a cycloparaffin molecule, and the cycloalkyl group includes a monocyclic cycloalkyl group, a polycyclic cycloalkyl group, and a bridged cycloalkyl group. Examples of the cycloalkyl group may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, camphenethyl, and the like. The cycloalkyl group has 3 to 20 carbon atoms, preferably 3 to 15 carbon atoms, more preferably 3 to 10 carbon atoms.
In the present specification, whatThe aryl group refers to the generic term for monovalent groups remaining after removal of a hydrogen atom from the aromatic nucleus carbon of an aromatic compound molecule. The aryl group comprises a monocyclic aryl group, a polycyclic aryl group, a fused ring aryl group, or a combination thereof. Examples of the aryl group may include phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthryl, triphenylenyl, anthracenyl, pyrenyl, perylenyl, Radicals, fluoranthenyl, fluorenyl, benzofluorenyl, spirobifluorenyl, benzospirobifluorenyl, and the like, but are not limited thereto. The number of carbon atoms of the aryl group is 6 to 30, preferably 6 to 25, preferably 6 to 18, and more preferably 6 to 12.
In the present specification, the heteroaryl group refers to a generic term for a group in which one or more carbon atoms in the aryl group are replaced with a heteroatom including, but not limited to, oxygen, sulfur, nitrogen, phosphorus, boron, silicon, and the like. The heteroaryl comprises a monocyclic heteroaryl, a fused ring heteroaryl, or a combination thereof. Examples of the heteroaryl group may include benzofuranyl, naphthofuranyl, phenanthrofuranyl, triphenylfuranyl, anthracofuranyl, pyridofuranyl, pyrimidofuranyl, pyrazinofuranyl, pyridazinofuranyl, triazinofuranyl, quinolinofuranyl, isoquinolinofuranyl, quinazolinofuranyl, quinoxalinofuranyl, azaphenanthrofuranyl, azaanthracofuranyl, azatriphenylfuranyl, dibenzofuranyl, benzothienyl, naphthothienyl, phenanthrothienyl, triphenylene thienyl, anthracenothienyl, pyridothienyl, pyrimidothienyl, pyrazinothienyl, pyridazinothienyl, quinophtheneyl, isoquinolothienyl, quinazolinothienyl, quinoxalinothienyl, azaphenanthrothienyl, azaanthracenothienyl, azatriphenylene thienyl, dibenzothienyl, indolyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolinyl, quinazolinyl, etc., but are not limited thereto. The number of carbon atoms of the heteroaryl group may be 2 to 30, preferably 2 to 25, and more preferably 3 to 18.
In the present specification, the condensed cyclic group of the alicyclic ring and the aromatic ring means a generic term for a monovalent group which is left after the alicyclic ring and the aromatic ring are condensed together to remove one hydrogen atom. Examples of the condensed cyclic groups of the alicyclic and aromatic rings may include, but are not limited to, benzocyclopropane group, benzocyclobutane group, benzocyclobutene group, benzocycloheptane group, benzocycloheptene group, indanyl group, indenyl group, tetrahydronaphthyl group, dihydronaphthyl group, and the like. The alicyclic has 3 to 20 carbon atoms, preferably 3 to 15 carbon atoms, and more preferably 3 to 10 carbon atoms. The number of carbon atoms of the aromatic ring is 6 to 30, preferably 6 to 25, preferably 6 to 18, still preferably 6 to 12, more preferably 6 to 10.
In the present specification, the arylene group refers to a generic term for a divalent group remaining after two hydrogen atoms are removed from the aromatic nucleus carbon of an aromatic compound molecule. The arylene group includes a monocyclic arylene group, a polycyclic arylene group, a fused ring arylene group, or a combination thereof. Examples of the arylene group may include phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, fluorenylene, benzofluorenylene, spirobifluorenylene, and the like, but are not limited thereto. The arylene group has 6 to 30 carbon atoms, preferably 6 to 25 carbon atoms, preferably 6 to 18 carbon atoms, more preferably 6 to 10 carbon atoms.
In the present specification, the heteroarylene group means a divalent group in which at least one carbon atom in the arylene group is substituted with a heteroatom. The hetero atom is selected from oxygen, sulfur, nitrogen, phosphorus, boron, silicon, and the like, but is not limited thereto. The heteroarylene includes a monocyclic heteroarylene, a polycyclic heteroarylene, a fused ring heteroarylene, or a combination thereof. Examples of the heteroarylene group may include, but are not limited to, a pyridylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolylene group, a quinoxalinylene group, a benzofuranylene group, a benzothienyl group, and the like. The heteroarylene group has 2 to 30 carbon atoms, preferably 2 to 25 carbon atoms, and more preferably 3 to 18 carbon atoms.
In the present specification, the term "fused ring-sub group" of an alicyclic ring and an aromatic ring means a generic term for a divalent group which is obtained by fusing an alicyclic ring and an aromatic ring together and then removing two hydrogen atoms. Examples of the fused-back cyclic group of the alicyclic ring and the aromatic ring may include, but are not limited to, indanylene, indenylene, tetrahydronaphthalene, dihydronaphthalene, benzocyclopropylene, benzocyclobutylene, benzocyclobutene, and the like. The alicyclic has 3 to 20 carbon atoms, preferably 3 to 15 carbon atoms, preferably 3 to 10 carbon atoms. The number of carbon atoms of the aromatic ring is 6 to 30, preferably 6 to 25, preferably 6 to 18, preferably 6 to 12, more preferably 6 to 10.
The invention provides a carbazole-containing triarylamine compound represented by the following formula 1,
ar is selected from the group represented by formula 1-a,
said X is selected from O, S, N (R) x ) Or C (R) x ) 2 The R is x The same or different one selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring condensed ring groups;
the ring A is selected from one of a substituted or unsubstituted 6-30 membered aromatic ring and a substituted or unsubstituted 6-30 membered nitrogen-containing heteroaromatic ring, and the ring A is not substituted or unsubstituted
The m is 1 An integer selected from 0 to 2, said R 1 The same or different is selected from one of hydrogen, deuterium, tritium, cyano, F, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and condensed ring group of C6-C30 aromatic ring, or adjacent two R 1 Are bonded to each other to form a substituted or unsubstitutedIs a ring of (2);
the Ar is as follows 1 、Ar 2 Independently selected from one or a combination of the groups shown in the formula 1-a,
said e 1 An integer selected from 0 to 5, said e 2 An integer selected from 0 to 4, each R 2 、R 20 The same or different is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and condensed ring group of C6-C30 aromatic ring, or adjacent two R 2 Two adjacent R 20 Bonded to each other to form a substituted or unsubstituted ring;
the R is 0 The same or different is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and condensed ring group of C6-C30 aromatic ring, or adjacent two R 0 Bonded to each other to form a substituted or unsubstituted ring;
The E is selected from N or CH and at least contains one N;
the L is 1 、L 2 、L 3 、L 4 Independently selected from one of single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C2-C30, substituted or unsubstituted alicyclic of C3-C20 and condensed ring group of arylene of C6-C30;
said n 1 An integer selected from 0 to 3, said n 2 An integer selected from 0 to 4, said R's being the same or different and selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstitutedSubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, one of the fused ring groups of the substituted or unsubstituted C3-C20 alicyclic ring and the C6-C30 aromatic ring, or adjacent two R groups are bonded to each other to form a substituted or unsubstituted ring.
Preferably, said R 1 The substituents on the aryl groups in (a) are selected from the following groups: hydrogen, deuterium, tritium, cyano, F, substituted or unsubstituted silyl, substituted or unsubstituted C1 to C15 alkyl, substituted or unsubstituted C3 to C15 cycloalkyl, substituted or unsubstituted C6 to C25 aryl, substituted or unsubstituted C2 to C25 heteroaryl, substituted or unsubstituted C3 to C15 alicyclic and fused ring groups of the aromatic ring of C6 to C25.
Preferably, the saidRing A of (a) is selected from one of the groups shown below,
the Y's are identical or different and are selected from N or C (R y ) The R is y One selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring condensed ring groups, or two adjacent R y Bonded to each other to form a substituted or unsubstituted ring;
and ring A is not substituted or unsubstituted
Preferably, the saidRing A of (a) is selected from one of the groups shown below,
said f 1 An integer selected from 0 to 4, said f 2 An integer selected from 0 to 3, said f 3 An integer selected from 0 to 2, said f 4 An integer selected from 0 to 6, said f 5 An integer selected from 0 to 5, said f 6 An integer selected from 0 to 8, said f 7 An integer selected from 0 to 7;
the R is y The same or different is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclic and condensed ring group of C6-C25 aromatic ring, or adjacent two R y Are bonded to each other to form a substituted or unsubstituted ring.
Preferably, said R x The same or different is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutylalkyl, substituted or unsubstituted cyclopentylalkyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstitutedOr unsubstituted triphenylene, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzocyclopropenyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted benzospirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted isoquinolyl, or an unsubstituted or unsubstituted one of the substituents;
The R is 1 The same or different is selected from hydrogen, deuterium, tritium, cyano, F, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropanyl, substituted or unsubstituted cyclobutanyl, substituted or unsubstituted cyclopentylalkyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted tetrahydroindenyl, unsubstituted naphtylOr one of unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl;
The R is y The same or different is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentylalkyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl substituted or unsubstituted triphenylene, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutene, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted benzospirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl And one of a benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, and a substituted or unsubstituted isoquinolinyl group.
Preferably, the Ar 1 、Ar 2 Independently selected from one or a combination of the groups shown in the formula 1-a,
said e 1 An integer selected from 0 to 5, said e 2 An integer selected from 0 to 4, said e 3 An integer selected from 0 to 7, said e 4 An integer selected from 0 to 9, said e 5 An integer selected from 0 to 3, said e 6 An integer selected from 0 to 2, said e 7 An integer selected from 0 to 6, said e 8 An integer selected from 0 to 8, said e 9 An integer selected from 0 to 10;
said each R 2 、R 20 The same or different is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclic and condensed ring group of C6-C25 aromatic ring, or adjacent two R 2 Two adjacent R 20 Bonded to each other to form a substituted or unsubstituted ring;
the R is i The same or different is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic ringOne of the fused ring groups of (2), or two adjacent R i Are bonded to each other to form a substituted or unsubstituted ring.
Preferably, each R 2 、R 20 The same or different is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropanyl, substituted or unsubstituted cyclobutylalkyl, substituted or unsubstituted cyclopentylalkyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzocyclopropanyl substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, and, one of a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, or two adjacent R' s 2 Two adjacent R 20 Bonded to each other to form a substituted or unsubstituted ring;
the R is i Identical or differentSelected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropanyl, substituted or unsubstituted cyclobutylalkyl, substituted or unsubstituted cyclopentanyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronapthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted benzofluorenyl, unsubstituted benzofuranyl, substituted or unsubstituted benzofuranyl, or adjacent two R i Are bonded to each other to form a substituted or unsubstituted ring.
Preferably, the L 1 、L 2 、L 3 、L 4 Independently selected from a single bond or one or a combination of the groups shown below,
the k is 1 An integer selected from 0 to 4;
the R is 3 The same or different alkanes selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkaneA group, a substituted or unsubstituted C3-C15 cycloalkyl group, a substituted or unsubstituted C6-C25 aryl group, a substituted or unsubstituted C2-C25 heteroaryl group, one of a substituted or unsubstituted C3-C15 alicyclic ring and a C6-C25 aromatic ring condensed ring group, or two adjacent R' s 3 Bonded to each other to form a substituted or unsubstituted ring;
the Z is the same or different and is selected from N or CH, and at least contains one N.
Preferably, the L 1 、L 2 、L 3 、L 4 Independently selected from a single bond or one or a combination of the groups shown below,
the k is 1 An integer selected from 0 to 4, said k 2 An integer selected from 0 to 3, said k 3 An integer selected from 0 to 2, said k 4 An integer selected from 0 to 6, said k 5 An integer selected from 0 to 8, said k 6 An integer selected from 0 to 10;
the R is 3 The same or different one selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic ring condensed ring groups;
The R is j The same or different is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclic and C6-C25 arylOne of the condensed ring groups of the ring, or two adjacent R' s j Are bonded to each other to form a substituted or unsubstituted ring.
Preferably, said R 3 The same or different is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropanyl, substituted or unsubstituted cyclobutylalkyl, substituted or unsubstituted cyclopentylalkyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzocyclopropanyl substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, and, one of a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group;
The R is j The same or different radicals are selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstitutedSubstituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted benzobisfluorenyl, substituted or unsubstituted benzobisspirofluorenyl, substituted or unsubstituted benzofuranyl, or adjacent two R j Are bonded to each other to form a substituted or unsubstituted ring.
Preferably, the method comprises the steps of, the R groups are the same or different and are selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutanyl, substituted or unsubstituted cyclopentylalkyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl substituted or unsubstituted benzocyclopropane group, substituted or unsubstituted benzocyclobutane group, substituted or unsubstituted benzocyclobutene group, substituted or unsubstituted indanyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted tetrahydronaphthyl group, substituted or unsubstituted dihydronaphthyl group, substituted or unsubstituted benzocycloheptane group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted benzofluorenyl group, substituted or unsubstituted spirobifluorenyl group, substituted or unsubstituted benzospirobifluorenyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted benzothienyl group, substituted or unsubstituted dibenzothienyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, one of a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, or adjacent two R groups are bonded to each other to form a substituted or unsubstituted ring.
Preferably, the carbazole-containing triarylamine compound of formula I is selected from at least one of the structures shown below,
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the specific chemical structures of the carbazole-containing triarylamine compound shown in formula 1 of the present invention are listed above, but the present invention is not limited to these chemical structures, and substituents are included in the structures shown in formula 1.
In addition, the invention also provides an organic electroluminescent device, which contains the carbazole-containing triarylamine compound.
Preferably, the organic electroluminescent device comprises an anode, a cathode, and an organic layer between the anode and the cathode, the organic layer containing the carbazole-containing triarylamine compound of the present invention.
Preferably, the organic layer comprises a hole transport region containing the carbazole-containing triarylamine compound of the present invention.
Preferably, the hole transport region comprises a hole transport layer comprising the carbazole-containing triarylamine compound of the present invention.
The functional layer of the organic electroluminescent device of the present invention may contain at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a capping layer, and the like. Any functional layer having hole injection and/or transport properties, electron injection and/or transport properties, light emitting properties or light extraction properties should be included. Each functional layer may be formed of a single film or a plurality of films, and each film may be formed of only one material or a plurality of materials.
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:
anode: the anode material of the present invention requires a material having a high work function in order to inject holes into the organic layer. The anode includes, but is not limited to, materials, metals or alloys thereof, metal oxides, laminates, and the like as described below. Specific examples may include silver (Ag), gold (Au), copper (Cu), nickel (Ni), indium Tin Oxide (ITO), zinc aluminum oxide (Al: znO), indium tin oxide/silver/indium tin oxide (ITO/Ag/ITO), and the like, but are not limited thereto.
And (3) cathode: the cathode material of the present invention needs to have a low work function in order to inject electrons into the organic layer. The cathode includes, but is not limited to, materials, metals or alloys thereof, laminates, and the like as described below. Specific examples may include aluminum (Al), silver (Ag), lead (Pb), tin (Sn), strontium (Sr), samarium (Sm), magnesium: silver (Mg: ag), ytterbium gold (Yb: au), and the like, but are not limited thereto.
Hole injection layer: the hole injection material has the effects of reducing the surface roughness of ITO, reducing the internal defects of devices, reducing hole injection potential barriers and the like. The hole injection material includes, but is not limited to, materials such as metal oxides and phthalocyanines Low molecular organic compounds such as aromatic amine compounds, polycyano-containing conjugated organic materials, and high molecular materials, and specific examples thereof may include silver oxide (AgO), vanadium pentoxide (V 2 O 5 ) Copper phthalocyanine (CuPc), 4' -tris (N- (naphthalen-1-yl) -N-phenyl-amino) triphenylamine (1-TNATA), 4', 4' -tris [ 2-naphthylphenylamino ]]Triphenylamine (2-TNATA), 1,4,5,8,9,11-hexaazabenzonitrile (HAT-CN), poly (3, 4-ethylenedioxythiophene)/poly (styrenesulfonic acid) (PEDOT/PSS), and the like, but are not limited thereto,
hole transport layer: the hole transport material of the present invention has the effect of improving the transport efficiency of holes in the device and blocking electrons in the light emitting layer. The hole transport layer includes, but is not limited to, materials such as aromatic amine derivatives, carbazole derivatives, polymers, and the like. Specific examples may include N, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine (NPB), N '-bis (naphthalen-2-yl) -N, N' -bis (phenyl) biphenyl-4, 4 '-diamine (β -NPB), 4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline ] (TAPC), N '-diphenyl-N, N' -bis (3-methylphenyl) -1,1 '-biphenyl-4, 4' -diamine (TPD), 2, 7-tetrakis (diphenylamino) -9, 9-spirobifluorene (Spiro-TAD), and the like. The carbazole derivatives include, but are not limited to, 1,3, 5-tris (9-carbazolyl) benzene (TCB), 4',4 "-tris (carbazol-9-yl) triphenylamine (TCTA), poly (4-vinyl triphenylamine) (PVTPA), and the like. Preferred are carbazole-containing triarylamine compounds of formula 1 of the present invention.
Light emitting layer: the luminescent layer of the invention comprises a host material and a doping material, and the luminescent material can be a red luminescent material, a green luminescent material, a blue luminescent material or a combination thereof. The doping ratio of the host material and the doping material may vary depending on the material used, and the doping ratio of the doping material is usually 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%.
The host material of the light emitting layer needs to have bipolar charge transport properties and also needs to have an appropriate energy level to efficiently transfer excitation energy to the guest light emitting material. The main material may be one material or two or more materials. Host materials include, but are not limited to, materials such as heterocyclic compounds, aromatic amine compounds,fused aromatic ring derivatives, metal complexes, siliceous compounds and the like, specific examples of which may include 2- (10-phenylanthracen-9-yl) dibenzo [ b, d ]]Furan, 2, 7-bis (9H-carbazol-9-yl) -9, 9-dimethylfluorene (DMFL-CBP), 2, 7-bis (diphenylphosphate) -9,9' -spirobifluorene (SPPO 13), 2, 7-bis (carbazol-9-yl) -9, 9-spirobifluorene (Spiro-2 CBP), 3, 5-bis (3- (9H-carbazol-9-yl) phenyl) pyridine (35 DCzPPy), 3' -bis (dibenzothiophen-4-yl) -1,1' -biphenyl (m-BPDBT), 3' - (dibenzothiophen-4-yl) -10-phenyl-10H-Spiro [ acridine-9, 9' -fluorene ](STDBT-4), 1, 4-bis (9-phenyl-9H-fluoren-9-yl) benzene (pDPPB), tris (8-hydroxyquinoline) aluminum (Alq) 3 ) 9- (4-tert-butylphenyl) -3, 6-bis (triphenylsilyl) -9H carbazole (CzSi), etc., but is not limited thereto.
The doping material may be a fluorescent material, a phosphorescent material, a TADF material, or a combination thereof. Doping materials include, but are not limited to, materials such as metal complexes, aromatic amine derivatives, styrylamine compounds, fused aromatic compounds, heterocyclic compounds, and the like. Specific examples may include tris [2- (2, 4-difluorophenyl) pyridine]Ir (Fppy) 3 ) Bis (3, 5-difluoro-2- (2-pyridinyl) phenyl- (2-carboxypyridinyl) iridium (FIrPic), bis (2-phenylpyridine) iridium acetylacetonate (Ir (ppy)) 2 (acac)), tris (2-phenylpyridine) iridium (Ir (ppy) 3 ) Tris [ 2-phenyl-4-methylquinoline)]Ir (Mphq) 3 ) Tris [2- (4-n-hexylphenyl) quinoline ] iridium (Hex-Ir (phq) 3 ) Ir (piq) iridium bis (1-phenyl-isoquinoline) (acetylacetonate) 2 (acac)), tris (1-phenyl-isoquinoline) iridium (Ir (piq) 3 ) N1, N6-bis (6- (tert-butyl) dibenzo [ b, d)]Furan-4-yl) -N1, N6-diorthotoluene-1, 6-diamine, 1, 4-bis (4- (9H-carbazol-9-yl) styryl) benzene (BCzSB), 2,5,8, 11-tetra-tert-butylperylene (TBPe), 9, 10-bis [ N, N-di (p-tolyl) amino group ]Anthracene (TTPA), 9, 10-bis [ N- (m-tolyl) phenylamino ]]Anthracene (TPA), 4- (dicyanomethylene) -2-tert-butyl-6- (1, 7-tetramethyl julolidine-9-enyl) -4H-pyran (DCJTB), 4- (dicyanomethylene) -2-methyl-6- (4-dimethylaminostyryl) -4H-pyran (DCM), and the like, but are not limited thereto.
Hole blocking layer: the hole blocking layer can block holes in the light-emitting layer, and the combination rate of electrons and holes is improved. The hole blocking layer material may include imidazole derivatives, phenanthroline derivatives, triazole derivatives, rare earth complexes, oxazole derivatives, triazine derivatives, etc., such as 4, 7-diphenyl-1, 10-phenanthroline (Bphen), 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1, 1' -biphenyl-4-hydroxy) aluminum (BAlq), etc., but is not limited thereto.
Electron transport layer: the electron transport material of the present invention has the effect of improving the transport efficiency of electrons in the device and blocking holes in the light emitting layer. The electron transport layer includes, but is not limited to, materials, metal complexes, heteroaromatic compounds, and the like as described below. Specific examples may include aluminum 8-hydroxyquinoline (Alq 3 ) Tris (4-methyl-8-hydroxyquinoline) aluminum (Almq), 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3, 4-oxadiazole (PBD), 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), 3- (biphenyl-4-yl) -5- (4-tert-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ), 1,3, 5-tris [ (3-pyridinyl) -phenyl ]]Benzene (TmPyPB), etc., but is not limited thereto.
Electron injection layer: the electron injection material of the invention plays a role in reducing the electron injection barrier between the cathode and the organic layer and effectively injecting electrons into the organic layer. The electron injection layer material includes, but is not limited to, materials as described below, metals, metal compounds, metal oxides, and the like. Specific examples may include lithium (Li), lithium fluoride (LiF), cesium fluoride (CsF), lithium oxide (Li) 2 O), lithium boron oxide (LiBO) 2 ) Cesium carbonate (Cs) 2 CO 3 ) 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.
Synthetic examples
Raw materials and reagents: the starting materials or reagents used in the following synthetic examples are not particularly limited and may be commercially available products or prepared by methods well known to those skilled in the art. The raw materials and the reagents used in the invention are all reagent pure.
Instrument: g2—si quadrupole tandem time-of-flight high resolution mass spectrometer (waters, uk); vario EL cube organic element analyzer (Elementar, germany).
The method for producing the carbazole-containing triarylamine compound shown in formula 1 of the present invention is not particularly limited, and conventional methods known to those skilled in the art can be employed. For example, the carbazole-containing triarylamine compound represented by formula 1 of the present invention can be produced by the synthetic route shown below.
The Xn is halogen, for example, xn is the same or different and is selected from Cl, br and I.
Synthesis example 1 Synthesis of Compound 7
Preparation of A-7: a-7 (24.20 g,120.00 mmol), b-7 (23.64 g,120.00 mmol), copper powder (11.44 g,180.00 mmol), potassium carbonate (49.76 g,360.00 mmol), 18-crown-6 (2.54 g,9.60 mmol) and 1, 2-dichlorobenzene (1.5L) were added to the flask under nitrogen and stirred under reflux for 10 hours. After the reaction was completed, distilled water was added, followed by extraction with ethyl acetate, and the organic phase was dried over anhydrous magnesium sulfate, filtered, concentrated by distillation under reduced pressure, and recrystallized from toluene to give A-7 (27.84 g, 73%); the purity of the solid detected by HPLC is not less than 99.79%.
Preparation of B-7: to the reaction flask were added A-7 (25.42 g,80.00 mmol), pinacol biborate (20.32 g,80.00 mmol), (1, 1' -bis (diphenylphosphino) ferrocene) palladium dichloride (0.18 g,0.24 mmol), potassium acetate (15.70 g,160.00 mmol), DMF (400 ml) under reflux and stirred for 9 hours. After the reaction was completed, cooled to room temperature, water was added, extracted with dichloromethane, the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and recrystallized with toluene: methanol=5:1 to give B-7 (26.52 g, 81%); HPLC detection of solid purity ∈ 99.85%.
Preparation of C-7: to the reaction flask were added B-7 (24.56 g,60.00 mmol), c-7 (11.49 g,60.00 mmol), tetrakis triphenylphosphine palladium (0.69 g,0.60 mmol), potassium carbonate (12.44 g,90.00 mmol), tetrahydrofuran (250 ml), water (100 ml) under nitrogen, and stirred under reflux for 7 hours. After the reaction was completed, cooled to room temperature, water was added, extracted with dichloromethane, the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and toluene was used: n-hexane=4:1 recrystallisation to give C-7 (17.02 g, 72%); HPLC detection of solid purity ∈ 99.80%.
Preparation of D-7: to a reaction flask was added C-7 (15.75 g,40.00 mmol), D-7 (3.80 g,40.80 mmol), palladium acetate (0.07 g,0.32 mmol), tri-tert-butylphosphine (0.13 g,0.64 mmol), sodium tert-butoxide (4.61 g,48.00 mmol) and toluene (400 ml) under nitrogen protection, stirred under reflux for 11 hours, cooled to room temperature, added with water, extracted with ethyl acetate, combined organic phases, dried over anhydrous magnesium sulfate, the solvent removed under reduced pressure, recrystallized from ethyl acetate/petroleum ether (4:1) to give D-7 (13.52 g, 75%); the HPLC purity is more than or equal to 99.87 percent.
Preparation of compound 7: to the reaction flask were added D-7 (9.01 g,20.00 mmol), e-7 (4.66 g,20.00 mmol), sodium t-butoxide (2.31 g,24.00 mmol), dibenzylideneacetone dipalladium (0.18 g,0.20 mmol), tri-t-butylphosphine (0.08 g,0.40 mmol), toluene (150 ml) under nitrogen protection, and the reaction was carried out under reflux for 5 hours. After the reaction was completed, cooled to room temperature, water was added, the organic phase was separated, dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the crude product was recrystallized from toluene/ethanol (3:1) to give compound 7 (10.01 g, 83%); HPLC purity is more than or equal to 99.94%. Mass spectrum m/z:602.2342 (theory of the following)Value: 602.2358). Theoretical element content (%) C 44 H 30 N 2 O: c,87.68; h,5.02; n,4.65. Measured element content (%): c,87.65; h,5.04; n,4.64.
Synthesis example 2 Synthesis of Compound 20
According to the production method of synthetic example 1, equimolar a-7, b-7, d-7 were replaced with equimolar a-20, b-20, d-20, respectively, to give compound 20 (11.65 g); HPLC purity is more than or equal to 99.94%. Mass spectrum m/z:736.3467 (theory: 736.3454). Theoretical element content (%) C 54 H 44 N 2 O: c,88.01; h,6.02; n,3.80. Measured element content (%): c,88.04; h,6.01; n,3.83.
Synthesis example 3 Synthesis of Compound 66
According to the production method of Synthesis example 1, equimolar C-7, d-7, e-7 were replaced with equimolar C-20, d-66, e-66, respectively, to give Compound 66 (11.61 g); HPLC purity is more than or equal to 99.92%. Mass spectrum m/z:734.2381 (theory: 734.2392). Theoretical element content (%) C 52 H 34 N 2 OS: c,84.99; h,4.66; n,3.81. Measured element content (%): c,84.96; h,4.68; n,3.84.
Synthesis example 4 Synthesis of Compound 77
According to the production method of synthetic example 1, equimolar a-7, b-7, d-7 were replaced with equimolar a-20, b-77, d-66, respectively, to give compound 77 (11.38 g); HPLC purity is more than or equal to 99.96%. Mass spectrum m/z:678.2679 (theory: 678.2671). Theoretical element content (%) C 50 H 34 N 2 O: c,88.47; h,5.05; n,4.13. Measured element content (%): c,88.43; h,5.03; n,4.15.
Synthesis example 5 Synthesis of Compound 85
According to the production method of synthetic example 1, equimolar a-7, b-7, d-7 were replaced with equimolar a-85, b-85, d-66, respectively, to give compound 85 (12.17 g); HPLC purity is more than or equal to 99.92%. Mass spectrum m/z:810.3625 (theory: 810.3610). Theoretical element content (%) C 60 H 46 N 2 O: c,88.86; h,5.72; n,3.45. Measured element content (%): c,88.83; h,5.71; n,3.47.
Synthesis example 6 Synthesis of Compound 88
According to the production method of Synthesis example 1, equimolar amounts of a-7, b-7, d-7, e-7 were replaced with equimolar amounts of a-20, b-88, d-66, e-88, respectively, to give Compound 88 (11.16 g); the HPLC purity is more than or equal to 99.97 percent. Mass spectrum m/z:688.3281 (theory: 688.3299). Theoretical element content (%) C 50 H 24 D 10 N 2 O: c,87.18; h,6.44; n,4.07. Measured element content (%): c,87.19; h,6.42; n,4.05.
Synthesis example 7 Synthesis of Compound 91
According to the production method of synthetic example 1, equimolar amounts of a-7, c-7, d-7 were replaced with equimolar amounts of a-91, c-91, d-66, respectively, to give compound 91 (11.04 g); HPLC purity is more than or equal to 99.96%. Mass spectrum m/z:689.3377 (theory: 689.3362). Theoretical element content (%) C 50 H 23 D 11 N 2 O: c,87.05; h,6.57; n,4.06. Measured element content (%): c,87.08; h,6.56; n,4.08.
Synthesis example 8 Synthesis of Compound 95
According to the production method of synthetic example 1, equimolar b-7, d-7 were replaced with equimolar b-20, d-66, respectively, to give compound 95 (11.13 g); HPLC purity is more than or equal to 99.94%. Mass spectrum m/z:678.2685 (theory: 678.2671). Theoretical element content (%) C 50 H 34 N 2 O: c,88.47; h,5.05; n,4.13. Measured element content (%): c,88.48; h,5.08; n,4.11.
Synthesis example 9 Synthesis of Compound 101
According to the production method of synthetic example 1, equimolar amounts of a-7, b-7, c-7, d-7 were replaced with equimolar amounts of a-20, b-101, c-101, d-66, respectively, to give compound 101 (12.30 g); HPLC purity is more than or equal to 99.92%. Mass spectrum m/z:830.3285 (theory: 830.3297). Theoretical element content (%) C 62 H 42 N 2 O: c,89.61; h,5.09; n,3.37. Measured element content (%): c,89.63; h,5.05; n,3.36.
Synthesis example 10 Synthesis of Compound 108
According to the production method of synthetic example 1, equimolar b-7, d-7 were replaced with equimolar b-108, d-66, respectively, to give compound 108 (11.52 g); HPLC purity is more than or equal to 99.91%. Mass spectrum m/z:728.2842 (theory: 728.2828). Theoretical element content (%) C 54 H 36 N 2 O：C,88.98；H,4.98；N,3.84。Measured element content (%): c,88.94; h,4.95; n,3.86.
Synthesis example 11 Synthesis of Compound 117
According to the production method of Synthesis example 1, equimolar D-7, e-7 were replaced with equimolar D-66, e-117, respectively, to give Compound 117 (12.02 g); HPLC purity is more than or equal to 99.95%. Mass spectrum m/z:750.3053 (theory: 750.3066). Theoretical element content (%) C 53 H 42 N 2 OSi: c,84.76; h,5.64; n,3.73. Measured element content (%): c,84.77; h,5.62; n,3.71.
Synthesis example 12 Synthesis of Compound 133
According to the production method of synthetic example 1, equimolar D-7, e-7 were replaced with equimolar D-95, e-133, respectively, to give compound 133 (11.00 g); the HPLC purity is more than or equal to 99.97 percent. Mass spectrum m/z:678.2686 (theory: 678.2671). Theoretical element content (%) C 50 H 34 N 2 O: c,88.47; h,5.05; n,4.13. Measured element content (%): c,88.45; h,5.08; n,4.15.
Synthesis example 13 Synthesis of Compound 135
According to the production method of synthetic example 1, equimolar a-7, b-7, d-7 were replaced with equimolar a-135, b-135, d-66, respectively, to give compound 135 (11.13 g); HPLC purity is more than or equal to 99.95%. Mass spectrum m/z:678.2687 (theory: 678.2671). Theoretical element content (%) C 50 H 34 N 2 O: c,88.47; h,5.05; n,4.13. Measured element content (%): c,88.45; h,5.08; n,4.16.
Synthesis example 14 Synthesis of Compound 136
According to the production method of synthetic example 1, equimolar amounts of a-7, b-7, d-7, e-7 were replaced with equimolar amounts of a-136, b-20, d-136, e-133, respectively, to give compound 136 (11.78 g); HPLC purity is more than or equal to 99.92%. Mass spectrum m/z:754.2971 (theory: 754.2984). Theoretical element content (%) C 56 H 38 N 2 O: c,89.10; h,5.07; n,3.71. Measured element content (%): c,89.13; h,5.06; n,3.73.
Synthesis example 15 Synthesis of Compound 156
According to the production method of Synthesis example 1, equimolar D-7, e-7 were replaced with equimolar D-77, e-156, respectively, to give Compound 156 (11.36 g); the HPLC purity is more than or equal to 99.93 percent. Mass spectrum m/z:718.2973 (theory: 718.2984). Theoretical element content (%) C 53 H 38 N 2 O: c,88.55; h,5.33; n,3.90. Measured element content (%): c,88.58; h,5.32; n,3.93.
Synthesis example 16 Synthesis of Compound 168
According to the production method of synthetic example 1, equimolar D-7, e-7 were replaced with equimolar D-77, e-168, respectively, to give compound 168 (13.74 g); HPLC purity is more than or equal to 99.92%. Mass spectrum m/z:860.3235 (theory: 860.3223). Theoretical element content (%) C 62 H 44 N 2 OSi: c,86.48; h,5.15; n,3.25. Measured element content (%): c,86.45; h,5.16; n,3.23.
Synthesis example 17 Synthesis of Compound 188
According to the production method of synthetic example 1, equimolar a-7, d-7, e-7 were replaced with equimolar a-20, d-188, e-188, respectively, to give compound 188 (12.77 g); the HPLC purity is more than or equal to 99.93 percent. Mass spectrum m/z:810.3623 (theory: 810.3610). Theoretical element content (%) C 60 H 46 N 2 O: c,88.86; h,5.72; n,3.45. Measured element content (%): c,88.88; h,5.75; n,3.44.
Synthesis example 18 Synthesis of Compound 203
According to the production method of synthetic example 1, equimolar amounts of a-7, b-7, c-7, d-7 were replaced with equimolar amounts of a-203, b-203, c-203, d-66, respectively, to give compound 203 (12.07 g); HPLC purity is more than or equal to 99.94%. Mass spectrum m/z:793.3075 (theory: 793.3093). Theoretical element content (%) C 58 H 39 N 3 O: c,87.74; h,4.95; n,5.29. Measured element content (%): c,87.75; h,4.93; n,5.26.
Synthesis example 19 Synthesis of Compound 229
According to the production method of synthetic example 1, equimolar B-7, c-7, d-7 were replaced with equimolar B-188, c-229, d-66, respectively, to give compound 229 (12.78 g); HPLC purity is more than or equal to 99.95%. Mass spectrum m/z:754.2995 (theory: 754.2984). Theoretical element content (%) C 56 H 38 N 2 O: c,89.10; h,5.07; n,3.71. Measured element content (%): c,89.14; h,5.05; n,3.72.
Synthesis example 20 Synthesis of Compound 271
According to the production method of synthetic example 1, equimolar amounts of a-7, b-7, d-7 were replaced with equimolar amounts of a-135, b-271, d-66, respectively, to give compound 271 (9.39 g); HPLC purity is more than or equal to 99.99%. Mass spectrum m/z:618.2141 (theory: 618.2130). Theoretical element content (%) C 44 H 30 N 2 S: c,85.40; h,4.89; n,4.53. Measured element content (%): c,85.42; h,4.85; n,4.51.
Synthesis example 21 Synthesis of Compound 282
According to the production method of synthetic example 1, equimolar amounts of a-7, b-7, d-7 were replaced with equimolar amounts of a-20, b-271, d-66, respectively, to give compound 282 (11.56 g); the HPLC purity is more than or equal to 99.97 percent. Mass spectrum m/z:694.2460 (theory: 694.2443). Theoretical element content (%) C 50 H 34 N 2 S: c,86.42; h,4.93; n,4.03. Measured element content (%): c,86.43; h,4.96; n,4.01.
Synthesis example 22 Synthesis of Compound 302
According to the preparation method of synthetic example 1, equimolar a-7, b-7, d-7 were replaced with equimolar respectivelya-20, b-302, d-66 to give compound 302 (12.63 g); HPLC purity is more than or equal to 99.94%. Mass spectrum m/z:770.2742 (theory: 770.2756). Theoretical element content (%) C 56 H 38 N 2 S: c,87.24; h,4.97; n,3.63. Measured element content (%): c,87.26; h,4.98; n,3.65.
Synthesis example 23 Synthesis of Compound 305
According to the production method of synthetic example 1, equimolar a-7, b-7, d-7 were replaced with equimolar a-20, b-305, d-66, respectively, to give compound 305 (11.56 g); HPLC purity is more than or equal to 99.90%. Mass spectrum m/z:740.2675 (theory: 740.2661). Theoretical element content (%) C 52 H 37 FN 2 S: c,84.29; h,5.03; n,3.78. Measured element content (%): c,84.27; h,5.04; n,3.75.
Synthesis example 24 Synthesis of Compound 311
According to the production method of synthetic example 1, equimolar a-7, b-7, d-7 were replaced with equimolar a-20, b-311, d-66, respectively, to give compound 311 (12.72 g); HPLC purity is more than or equal to 99.91%. Mass spectrum m/z:870.3051 (theory: 870.3069). Theoretical element content (%) C 64 H 42 N 2 S: c,88.24; h,4.86; n,3.22. Measured element content (%): c,88.26; h,4.83; n,3.26.
Synthesis example 25 Synthesis of Compound 318
According to the preparation method of synthetic example 1, equimolar C-7, d-7 and e-7 are replaced by equimolar C-282, d-318 and e-318 respectively to obtain the compound318 (11.16 g); the HPLC purity is more than or equal to 99.97 percent. Mass spectrum m/z:694.2456 (theory: 694.2443). Theoretical element content (%) C 50 H 34 N 2 S: c,86.42; h,4.93; n,4.03. Measured element content (%): c,86.43; h,4.96; n,4.02.
Synthesis example 26 Synthesis of Compound 341
According to the production method of synthetic example 1, equimolar a-7, b-7, d-7 were replaced with equimolar a-20, b-341, d-66, respectively, to give compound 341 (12.36 g); the HPLC purity is more than or equal to 99.89 percent. Mass spectrum m/z:834.3057 (theory: 834.3069). Theoretical element content (%) C 61 H 42 N 2 S: c,87.74; h,5.07; n,3.35. Measured element content (%): c,87.76; h,5.04; n,3.38.
Synthesis example 27 Synthesis of Compound 342
According to the production method of synthetic example 1, equimolar amounts of a-7, b-7, d-7 were replaced with equimolar amounts of a-342, b-342, d-66, respectively, to give compound 342 (11.84 g); HPLC purity is more than or equal to 99.91%. Mass spectrum m/z:758.2768 (theory: 758.2756). Theoretical element content (%) C 55 H 38 N 2 S: c,87.04; h,5.05; n,3.69. Measured element content (%): c,87.05; h,5.02; n,3.66.
Synthesis example 28 Synthesis of Compound 358
According to the production method of synthetic example 1, equimolar amounts of a-7, b-7, c-7, d-7 were replaced with equimolar amounts of a-20, b-358, c-101, d-66, respectively, to give compound 358 (11.26 g); HPLC purity99.97%. Mass spectrum m/z:694.2455 (theory: 694.2443). Theoretical element content (%) C 50 H 34 N 2 S: c,86.42; h,4.93; n,4.03. Measured element content (%): c,86.43; h,4.95; n,4.04.
Synthesis example 29 Synthesis of Compound 369
According to the production method of synthetic example 1, equimolar amounts of a-7, b-7, c-7, d-7 were replaced with equimolar amounts of a-20, b-369, c-369, d-66, respectively, to give compound 369 (11.12 g); the HPLC purity is more than or equal to 99.93 percent. Mass spectrum m/z:694.2459 (theory: 694.2443). Theoretical element content (%) C 50 H 34 N 2 S: c,86.42; h,4.93; n,4.03. Measured element content (%): c,86.45; h,4.92; n,4.06.
Synthesis example 30 Synthesis of Compound 383
According to the production method of synthetic example 1, equimolar B-7, c-7, d-7 were replaced with equimolar B-282, c-383, d-66, respectively, to give compound 383 (12.32 g); HPLC purity is more than or equal to 99.92%. Mass spectrum m/z:820.2928 (theory: 820.2912). Theoretical element content (%) C 60 H 40 N 2 S: c,87.77; h,4.91; n,3.41. Measured element content (%): c,87.73; h,4.93; n,3.45.
Synthesis example 31 Synthesis of Compound 392
According to the production method of synthetic example 1, equimolar a-7, b-7, d-7 were replaced with equimolar a-20, b-392, d-66, respectively, to give compound 392 (12.03 g); HPLC purity is more than or equal to 99.88%. Mass spectrum m/z:780.3517 (theory: 780.3504). Theoretical element content (%) C 59 H 44 N 2 : c,90.73; h,5.68; n,3.59. Measured element content (%): c,90.76; h,5.67; n,3.54.
Synthesis example 32 Synthesis of Compound 406
According to the production method of synthetic example 1, equimolar a-7, b-7, d-7 were replaced with equimolar a-20, b-406, d-66, respectively, to give compound 406 (12.28 g); the HPLC purity is more than or equal to 99.89 percent. Mass spectrum m/z:829.3443 (theory: 829.3457). Theoretical element content (%) C 62 H 43 N 3 : c,89.72; h,5.22; n,5.06. Measured element content (%): c,89.73; h,5.25; n,5.04.
Synthesis example 33 Synthesis of Compound 422
According to the production method of synthetic example 1, equimolar a-7, b-7, d-7, e-7 were replaced with equimolar a-20, b-77, d-66, e-422, respectively, to give compound 422 (11.37 g); HPLC purity is more than or equal to 99.92%. Mass spectrum m/z:728.2840 (theory: 728.2828). Theoretical element content (%) C 54 H 36 N 2 O: c,88.98; h,4.98; n,3.84. Measured element content (%): c,88.96; h,4.95; n,3.87.
Synthesis example 34 Synthesis of Compound 436
According to synthesis implementationThe preparation method of example 1, wherein equimolar D-7 and e-7 were replaced with equimolar D-66 and e-436, respectively, gave compound 436 (11.11 g); HPLC purity is more than or equal to 99.94%. Mass spectrum m/z:702.2689 (theory: 702.2671). Theoretical element content (%) C 52 H 34 N 2 O: c,88.86; h,4.88; n,3.99. Measured element content (%): c,88.89; h,4.86; n,3.95.
Synthesis example 35 Synthesis of Compound 451
According to the production method of synthetic example 1, equimolar amounts of a-7, b-7, d-7, e-7 were replaced with equimolar amounts of a-20, b-451, d-66, e-451, respectively, to give compound 451 (12.15 g); HPLC purity is more than or equal to 99.92%. Mass spectrum m/z:820.2926 (theory: 820.2912). Theoretical element content (%) C 60 H 40 N 2 S: c,87.77; h,4.91; n,3.41. Measured element content (%): c,87.74; h,4.92; n,3.45.
Synthesis example 36 Synthesis of Compound 458
According to the production method of synthetic example 1, equimolar B-7, d-7, e-7 were replaced with equimolar B-369, d-66, e-458, respectively, to give compound 458 (11.84 g); HPLC purity is more than or equal to 99.91%. Mass spectrum m/z:768.2586 (theory: 768.2599). Theoretical element content (%) C 56 H 36 N 2 S: c,87.47; h,4.72; n,3.64. Measured element content (%): c,87.48; h,4.76; n,3.62.
Synthesis example 37 Synthesis of Compound 500
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According to the preparation method of synthetic example 1, equimolarD-7 and e-7 are replaced by equimolar D-66 and e-500 respectively, so as to obtain a compound 500 (12.26 g); HPLC purity is more than or equal to 99.96%. Mass spectrum m/z:718.2995 (theory: 718.2984). Theoretical element content (%) C 53 H 38 N 2 O: c,88.55; h,5.33; n,3.90. Measured element content (%): c,88.59; h,5.31; n,3.93.
Synthesis example 38 Synthesis of Compound 537
According to the production method of synthetic example 1, equimolar b-7, d-7, e-7 were replaced with equimolar b-203, d-66, e-537, respectively, to give compound 537 (13.02 g); HPLC purity is more than or equal to 99.94%. Mass spectrum m/z:794.3283 (theory: 794.3297). Theoretical element content (%) C 59 H 42 N 2 O: c,89.14; h,5.33; n,3.52. Measured element content (%): c,89.12; h,5.36; n,3.55.
Synthesis example 39 Synthesis of Compound 551
According to the production method of synthetic example 1, equimolar C-7, d-7, e-7 were replaced with equimolar C-188, d-551, e-551, respectively, to give compound 551 (12.12 g); the HPLC purity is more than or equal to 99.89 percent. Mass spectrum m/z:786.2844 (theory: 786.2858). Theoretical element content (%) C 54 H 37 F 3 N 2 O: c,82.42; h,4.74; n,3.56. Measured element content (%): c,82.46; h,4.72; n,3.57.
Synthesis example 40 Synthesis of Compound 552
According to the preparation method of synthetic example 1, equimolar D-7 and e-7 were replaced with equimolar D-7 and e-7 respectivelyD-77, e-552 to give compound 552 (14.16 g); the HPLC purity is more than or equal to 99.93 percent. Mass spectrum m/z:852.4093 (theory: 852.4080). Theoretical element content (%) C 63 H 52 N 2 O: c,88.70; h,6.14; n,3.28. Measured element content (%): c,88.72; h,6.11; n,3.26.
Synthesis example 41 Synthesis of Compound 596
According to the production method of synthetic example 1, equimolar amounts of a-7, b-7, c-7, d-7, e-7 were replaced with equimolar amounts of a-20, b-596, c-596, d-66, e-596, respectively, to give compound 596 (12.69 g); HPLC purity is more than or equal to 99.91%. Mass spectrum m/z:845.3421 (theory: 845.3406). Theoretical element content (%) C 62 H 43 N 3 O: c,88.02; h,5.12; n,4.97. Measured element content (%): c,88.03; h,5.14; n,4.96.
Synthesis example 42 Synthesis of Compound 650
According to the production method of synthetic example 1, equimolar C-7, d-7, e-7 were replaced with equimolar C-188, d-66, e-650, respectively, to give compound 650 (13.64 g); HPLC purity is more than or equal to 99.92%. Mass spectrum m/z:842.3282 (theory: 842.3297). Theoretical element content (%) C 63 H 42 N 2 O: c,89.76; h,5.02; n,3.32. Measured element content (%): c,89.75; h,5.03; n,3.35.
Synthesis example 43 Synthesis of Compound 690
According to the preparation method of synthetic example 1, equimolar C-7, d-7, e-7 were replaced with equimolar C-20, d-136, e-690, respectively, to give compound 690 (13.42 g); the HPLC purity is more than or equal to 99.93 percent. Mass spectrum m/z:840.3155 (theory: 840.3141). Theoretical element content (%) C 63 H 40 N 2 O: c,89.97; h,4.79; n,3.33. Measured element content (%): c,89.95; h,4.76; n,3.34.
Synthesis example 44 Synthesis of Compound 696
According to the production method of Synthesis example 1, equimolar amounts of a-7, b-7, d-7, e-7 were replaced with equimolar amounts of a-20, b-696, d-696, e-690, respectively, to give Compound 696 (12.77 g); the HPLC purity is more than or equal to 99.89 percent. Mass spectrum m/z:839.2923 (theory: 839.2937). Theoretical element content (%) C 62 H 37 N 3 O: c,88.65; h,4.44; n,5.00. Measured element content (%): c,88.63; h,4.45; n,5.02.
Synthesis example 45 Synthesis of Compound 704
According to the production method of Synthesis example 1, equimolar C-7, e-7 were replaced with equimolar C-95, e-704, respectively, to give Compound 704 (11.96 g); HPLC purity is more than or equal to 99.90%. Mass spectrum m/z:766.2971 (theory: 766.2984). Theoretical element content (%) C 57 H 38 N 2 O: c,89.27; h,4.99; n,3.65. Measured element content (%): c,89.26; h,4.95; n,3.67.
Synthesis example 46 Synthesis of Compound 750
According to the production method of synthetic example 1, equimolar C-7, d-7, e-7 were replaced with equimolar C-188, d-66, e-750, respectively, to give compound 750 (12.17 g); the HPLC purity is more than or equal to 99.93 percent. Mass spectrum m/z:810.3628 (theory: 810.3610). Theoretical element content (%) C 60 H 46 N 2 O: c,88.86; h,5.72; n,3.45. Measured element content (%): c,88.85; h,5.74; n,3.48.
Synthesis example 47 Synthesis of Compound 773
According to the production method of synthetic example 1, equimolar amounts of b-7, d-7, e-7 were replaced with equimolar amounts of b-773, d-66, e-773, respectively, to give compound 773 (12.07 g); HPLC purity is more than or equal to 99.91%. Mass spectrum m/z:783.2722 (theory: 783.2708). Theoretical element content (%) C 56 H 37 N 3 S: c,85.79; h,4.76; n,5.36. Measured element content (%): c,85.75; h,4.73; n,5.38.
Synthesis example 48 Synthesis of Compound 792
According to the production method of synthetic example 1, equimolar b-7, d-7, e-7 were replaced with equimolar b-792, d-66, e-500, respectively, to give compound 792 (12.87 g); the HPLC purity is more than or equal to 99.93 percent. Mass spectrum m/z:810.3054 (theory: 810.3069). Theoretical element content (%) C 59 H 42 N 2 S: c,87.37; h,5.22; n,3.45. Measured element content (%): c,87.33; h,5.25; n,3.48.
Synthesis example 49 Synthesis of Compound 798
According to the production method of synthetic example 1, equimolar C-7, d-7, e-7 were replaced with equimolar C-282, d-798, e-500, respectively, to give compound 798 (12.09 g); HPLC purity is more than or equal to 99.90%. Mass spectrum m/z:774.2724 (theory: 774.2705). Theoretical element content (%) C 55 H 38 N 2 OS: c,85.24; h,4.94; n,3.61. Measured element content (%): c,85.25; h,4.91; n,3.66.
Synthesis example 50 Synthesis of Compound 816
According to the production method of synthetic example 1, equimolar B-7, d-7, e-7 were replaced with equimolar B-369, d-66, e-816, respectively, to give compound 816 (13.17 g); the HPLC purity is more than or equal to 99.93 percent. Mass spectrum m/z:810.3051 (theory: 810.3069). Theoretical element content (%) C 59 H 42 N 2 S: c,87.37; h,5.22; n,3.45. Measured element content (%): c,87.36; h,5.24; n,3.48.
Synthesis example 51 Synthesis of Compound 832
According to the production method of synthetic example 1, equimolar amounts of a-7, b-7, c-7, d-7, e-7 were replaced with equimolar amounts of a-20, b-832, c-596, d-136, e-500, respectively, to give compound 832 (12.03 g); HPLC purity is more than or equal to 99.92%. Mass spectrum m/z:812.2986 (theory: 812.2974). Theoretical element content (%) C 57 H 40 N 4 S: c,84.21; h,4.96; n,6.89. Measured element content (%): c,84.22; h,4.98; n,6.87.
Synthesis example 52 Synthesis of Compound 842
According to the production method of synthetic example 1, equimolar amounts of a-7, b-7, c-7, d-7, e-7 were replaced with equimolar amounts of a-842, b-842, c-842, d-842, e-500, respectively, to give compound 842 (12.59 g); HPLC purity is more than or equal to 99.91%. Mass spectrum m/z:873.3165 (theory: 873.3178). Theoretical element content (%) C 63 H 43 N 3 S: c,86.57; h,4.96; n,4.81. Measured element content (%): c,86.58; h,4.93; n,4.85.
Synthesis example 53 Synthesis of Compound 850
According to the production method of synthetic example 1, equimolar a-7, b-7, d-7, e-7 were replaced with equimolar a-20, b-850, d-66, e-500, respectively, to give compound 850 (12.23 g); the HPLC purity is more than or equal to 99.89 percent. Mass spectrum m/z:793.3469 (theory: 793.3457). Theoretical element content (%) C 59 H 43 N 3 : c,89.25; h,5.46; n,5.29. Measured element content (%): c,89.24; h,5.43; n,5.28.
Synthesis example 54 Synthesis of Compound 861
According to the production method of synthetic example 1, equimolar C-7, e-7 were replaced with equimolar C-282, e-861, respectively, to give compound 861 (12.50 g); the HPLC purity is more than or equal to 99.93 percent. Mass spectrum m/z:832.2923 (theory: 832.2912). Theoretical element content (%) C 61 H 40 N 2 S: c,87.95; h,4.84; n,3.36. Measured element content (%): c,87.97; h,4.85; n,3.34.
Synthesis example 55 Synthesis of Compound 872
According to the production method of Synthesis example 1, equimolar amounts of a-7, b-7, d-7, e-7 were replaced with equimolar amounts of a-872, b-358, d-66, e-773, respectively, to give Compound 872 (13.73 g); HPLC purity is more than or equal to 99.94%. Mass spectrum m/z:858.3055 (theory: 858.3069). Theoretical element content (%) C 63 H 42 N 2 S: c,88.08; h,4.93; n,3.26. Measured element content (%): c,88.05; h,4.94; n,3.23.
Synthesis example 56 Synthesis of Compound 888
According to the production method of synthetic example 1, equimolar B-7, e-7 were replaced with equimolar B-358, e-888, respectively, to give compound 888 (14.25 g); HPLC purity is more than or equal to 99.91%. Mass spectrum m/z:892.3867 (theory: 892.3851). Theoretical element content (%) C 65 H 52 N 2 S: c,87.41; h,5.87; n,3.14. Measured element content (%): c,87.43; h,5.86; n,3.17.
Synthesis example 57 Synthesis of Compound 895
According to the production method of synthetic example 1, equimolar B-7, c-7, d-7, e-7 were replaced with equimolar B-369, c-101, d-895, e-895, respectively, to give compound 895 (12.67 g%); HPLC purity is more than or equal to 99.90%. Mass spectrum m/z:855.2722 (theory: 855.2708). Theoretical element content (%) C 62 H 37 N 3 S: c,86.99; h,4.36; n,4.91. Measured element content (%): c,86.95; h,4.38; n,4.94.
Synthesis example 58 Synthesis of Compound 927
According to the production method of synthetic example 1, equimolar B-7, c-7, d-7, e-7 were replaced with equimolar B-282, c-101, d-66, e-927, respectively, to give compound 927 (13.69 g); the HPLC purity is more than or equal to 99.93 percent. Mass spectrum m/z:858.3056 (theory: 858.3069). Theoretical element content (%) C 63 H 42 N 2 S: c,88.08; h,4.93; n,3.26. Measured element content (%): c,88.05; h,4.94; n,3.23.
Synthesis example 59 Synthesis of Compound 946
According to the production method of synthetic example 1, equimolar D-7, e-7 were replaced with equimolar D-927, e-946, respectively, to give compound 946 (11.94 g); HPLC purity is more than or equal to 99.91%. Mass spectrum m/z:774.3057 (theory: 774.3069). Theoretical element content (%) C 56 H 42 N 2 S: c,86.79; h,5.46; n,3.61. Measured element content (%): c,86.78; h,5.44; n,3.62.
Synthesis example 60 Synthesis of Compound 982
According to the production method of synthetic example 1, equimolar B-7, c-7, d-7, e-7 were replaced with equimolar B-358, c-982, d-66, e-982, respectively, to give compound 982 (10.44 g); HPLC purity is more than or equal to 99.90%. Mass spectrum m/z:696.2333 (theory: 696.2348). Theoretical element content (%) C 48 H 32 N 4 S: c,82.73; h,4.63; n,8.04. Measured element content (%): c,82.76; h,4.62; n,8.05.
Synthesis example 61 Synthesis of Compound 1002
According to the production method of synthetic example 1, equimolar a-7, b-7, d-7 were replaced with equimolar a-20, b-1002, d-66, respectively, to give compound 1002 (13.76 g); HPLC purity is more than or equal to 99.91%. Mass spectrum m/z:870.3257 (theory: 870.3246). Theoretical element content (%) C 64 H 42 N 2 O 2 : c,88.25; h,4.86; n,3.22. Measured element content (%): c,88.27; h,4.84; n,3.25.
Device embodiment
In the invention, an ITO glass substrate is ultrasonically cleaned by 5% glass cleaning liquid for 2 times each for 20 minutes, and then ultrasonically cleaned by deionized water for 2 times each for 10 minutes. Sequentially ultrasonic cleaning with acetone and isopropanol for 20 min, and drying at 120deg.C. The organic materials are sublimated, and the purity is over 99.99 percent.
Test software, a computer, a K2400 digital source list manufactured by Keithley company in U.S. and a PR788 spectrum scanning luminance meter manufactured by Photo Research company in U.S. are combined into a combined IVL test system to test the driving voltage, luminous efficiency and CIE color coordinates of the organic electroluminescent device. Life testing an M6000 OLED life test system from McScience was used. The environment tested was atmospheric and the temperature was room temperature.
Example 1: preparation of organic electroluminescent device 1
Vacuum evaporating 1-TNATA on the ITO anode as a hole injection layer with the thickness of 55nm; vacuum evaporating the compound 7 as a hole transport layer, wherein the thickness of the hole transport layer is 50nm; vacuum vapor deposition of DMFL-CBP: ir (Mphq) on hole transport layer 3 =92:8 (wt%), forming a light emitting layer with a thickness of 33nm; vacuum evaporating BAlq on the light-emitting layer as a hole blocking layer, wherein the thickness is 8nm; vacuum evaporating Almq on the hole blocking layer as an electron transport layer, wherein the thickness is 44nm; vacuum evaporating Liq on the electron transport layer as an electron injection layer, wherein the evaporating thickness is 1.1nm; al is evaporated on the electron injection layer in vacuum as cathode with thickness of 140nm.
Examples 2 to 30: preparation of organic electroluminescent devices 2 to 30
The hole transport layer of example 1 was changed to compound 66, compound 77, compound 88, compound 91, compound 101, compound 135, compound 136, compound 188, compound 229, compound 302, compound 311, compound 318, compound 341, compound 369, compound 392, compound 422, compound 458, compound 500, compound 552, compound 650, compound 696, compound 704, compound 773, compound 816, compound 832, compound 850, compound 861, compound 946, compound 982, respectively, and the other steps were the same, to obtain organic electroluminescent devices 2 to 30.
Comparative examples 1 to 2: preparation of contrast organic electroluminescent devices 1-2
The compound 7 in the hole transport layer of example 1 was changed to R-1 and R-2, respectively, and the other steps were the same, to obtain comparative organic electroluminescent devices 1 to 2.
The results of the light emitting characteristics test of the organic electroluminescent devices prepared in examples 1 to 30 of the present invention and comparative examples 1 to 2 are shown in table 1.
Table 1 light emission characteristic test data of organic electroluminescent device
Example 31: preparation of organic electroluminescent device 31
Vacuum evaporating 2-TNATA on the ITO anode as a hole injection layer, wherein the thickness is 50nm; vacuum evaporating beta-NPB on the hole injection layer to be used as a first hole transport layer, wherein the thickness of the first hole transport layer is 35nm; vacuum evaporation of the present invention on the first hole transport layer The bright compound 7 is used as a second hole transport layer, and the thickness is 14nm; vacuum evaporating BH-1:BD-1=96:4 (wt%) on the second hole transport layer to form a light emitting layer with a thickness of 30nm; vacuum evaporating BCP on the light-emitting layer as a hole blocking layer, wherein the thickness is 10nm; vacuum evaporation of Alq on hole blocking layer 3 As an electron transport layer, the thickness was 25nm; vacuum evaporating LiF on the electron transport layer as an electron injection layer, wherein the evaporating thickness is 1.0nm; al is evaporated on the electron injection layer in vacuum as cathode with thickness of 140nm.
Examples 32 to 62: preparation of organic electroluminescent devices 32-62
The organic electroluminescent devices 32 to 62 were obtained by replacing the compound 7 in the second hole-transporting layer of example 31 with the compound 20, the compound 85, the compound 95, the compound 108, the compound 117, the compound 133, the compound 156, the compound 168, the compound 203, the compound 271, the compound 282, the compound 305, the compound 342, the compound 358, the compound 383, the compound 406, the compound 436, the compound 451, the compound 537, the compound 551, the compound 596, the compound 690, the compound 750, the compound 792, the compound 798, the compound 842, the compound 872, the compound 888, the compound 895, the compound 927, the compound 1002, respectively.
Comparative examples 3 to 4: preparation of contrast organic electroluminescent devices 3 to 4
The compound 7 in the second hole transport layer of example 31 was changed to R-1 and R-2, respectively, and the other steps were the same, to obtain comparative organic electroluminescent devices 3 to 4.
The results of the light emitting characteristics test of the organic electroluminescent devices prepared in examples 31 to 62 of the present invention and comparative examples 3 to 4 are shown in table 2.
Table 2 light emission characteristic test data of organic electroluminescent device
As can be seen from tables 1 and 2, the carbazole-containing triarylamine compound of formula 1 of the present invention is a hole transport material with good performance, and is used in organic electroluminescent devices, which have low driving voltage, high luminous efficiency, and long service life.
It should be noted that while the invention has been particularly described with reference to individual embodiments, those skilled in the art may make various modifications in form or detail without departing from the principles of the invention, which modifications are also within the scope of the invention.

Claims (10)

1. A carbazole-containing triarylamine compound is represented by the following formula 1,
ar is selected from the group represented by formula 1-a,
said X is selected from O, S, N (R) x ) Or C (R) x ) 2 The R is x The same or different one selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring condensed ring groups;
the ring A is selected from one of a substituted or unsubstituted 6-30 membered aromatic ring and a substituted or unsubstituted 6-30 membered nitrogen-containing heteroaromatic ring, and the ring A is not substituted or unsubstituted
The m is 1 An integer selected from 0 to 2, said R 1 The same or different is selected from one of hydrogen, deuterium, tritium, cyano, F, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and condensed ring group of C6-C30 aromatic ring, or adjacent two R 1 Bonded to each other to form a substituted or unsubstituted ring;
the Ar is as follows 1 、Ar 2 Independently selected from one or a combination of the groups shown in the formula 1-a,
Said e 1 An integer selected from 0 to 5, said e 2 An integer selected from 0 to 4, each R 2 、R 20 The same or different is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and condensed ring group of C6-C30 aromatic ring, or adjacent two R 2 Two adjacent R 20 Bonded to each other to form a substituted or unsubstituted ring;
the R is 0 The same or different is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and condensed ring group of C6-C30 aromatic ring, or adjacent two R 0 Bonded to each other to form a substituted or unsubstituted ring;
the E is selected from N or CH and at least contains one N;
the L is 1 、L 2 、L 3 、L 4 Independently selected from one of single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C2-C30, substituted or unsubstituted alicyclic of C3-C20 and condensed ring group of arylene of C6-C30;
Said n 1 An integer selected from 0 to 3, said n 2 An integer selected from 0 to 4, wherein R is the same or different and is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring condensed ring groups, or two adjacent R are bonded with each other to form a substituted or unsubstituted ring.
2. The carbazole-containing triarylamine compound of claim 1 wherein theRing A of (a) is selected from one of the groups shown below,
the Y's are identical or different and are selected from N or C (R y ) The R is y One selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring condensed ring groups, or two adjacent R y Bonded to each other to form a substituted or unsubstituted ring;
and ring A is not substituted or unsubstituted
3. The carbazole-containing triarylamine compound of claim 1 wherein theRing A of (a) is selected from one of the groups shown below,
said f 1 An integer selected from 0 to 4, said f 2 An integer selected from 0 to 3, said f 3 An integer selected from 0 to 2, said f 4 An integer selected from 0 to 6, said f 5 An integer selected from 0 to 5, said f 6 An integer selected from 0 to 8, said f 7 An integer selected from 0 to 7;
the R is y The same or different is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclic and condensed ring group of C6-C25 aromatic ring, or adjacent two R y Are bonded to each other to form a substituted or unsubstituted ring.
4. The carbazole-containing triarylamine compound according to claim 1, wherein Ar 1 、Ar 2 Independently selected from one or a combination of the groups shown in the formula 1-a,
Said e 1 An integer selected from 0 to 5, said e 2 An integer selected from 0 to 4, said e 3 An integer selected from 0 to 7, said e 4 An integer selected from 0 to 9, said e 5 An integer selected from 0 to 3, said e 6 An integer selected from 0 to 2, said e 7 An integer selected from 0 to 6, said e 8 An integer selected from 0 to 8, said e 9 An integer selected from 0 to 10;
said each R 2 、R 20 The same or different is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclic and condensed ring group of C6-C25 aromatic ring, or adjacent two R 2 Two adjacent R 20 Bonded to each other to form a substituted or unsubstituted ring;
the R is i The same or different is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclic and condensed ring group of C6-C25 aromatic ring, or adjacent two R i Are bonded to each other to form a substituted or unsubstituted ring.
5. The carbazole-containing triarylamine compound according to claim 1, wherein L 1 、L 2 、L 3 、L 4 Independently selected from a single bond or one or a combination of the groups shown below,
the k is 1 An integer selected from 0 to 4;
the R is 3 The same or different is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclic and condensed ring group of C6-C25 aromatic ring, or adjacent two R 3 Bonded to each other to form a substituted or unsubstituted ring;
the Z is the same or different and is selected from N or CH, and at least contains one N.
6. The carbazole-containing triarylamine compound according to claim 1, wherein L 1 、L 2 、L 3 、L 4 Independently selected from a single bond or one or a combination of the groups shown below,
the k is 1 An integer selected from 0 to 4, said k 2 An integer selected from 0 to 3, said k 3 An integer selected from 0 to 2, said k 4 An integer selected from 0 to 6, said k 5 An integer selected from 0 to 8, said k 6 An integer selected from 0 to 10;
the R is 3 The same or different radicals are selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstitutedOne of substituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic ring condensed ring groups;
the R is j The same or different is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclic and condensed ring group of C6-C25 aromatic ring, or adjacent two R j Are bonded to each other to form a substituted or unsubstituted ring.
7. The carbazole-containing triarylamine compound according to claim 1, wherein, the R groups are the same or different and are selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutanyl, substituted or unsubstituted cyclopentylalkyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl substituted or unsubstituted benzocyclopropane group, substituted or unsubstituted benzocyclobutane group, substituted or unsubstituted benzocyclobutene group, substituted or unsubstituted indanyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted tetrahydronaphthyl group, substituted or unsubstituted dihydronaphthyl group, substituted or unsubstituted benzocycloheptane group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted benzofluorenyl group, substituted or unsubstituted spirobifluorenyl group, substituted or unsubstituted benzospirobifluorenyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted benzothienyl group, substituted or unsubstituted dibenzothienyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted pyridyl group, one of a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, or adjacent two R groups are bonded to each other to form a substituted or unsubstituted ring.
8. The carbazole-containing triarylamine compound according to claim 1, wherein the carbazole-containing triarylamine compound of formula I is selected from at least one of the structures shown below,
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9. an organic electroluminescent device comprising the carbazole-containing triarylamine compound according to any one of claims 1 to 8.
10. The organic electroluminescent device according to claim 9, wherein the organic electroluminescent device comprises an anode, a cathode, and an organic layer between the anode and the cathode, the organic layer containing the carbazole-containing triarylamine compound according to any one of claims 1 to 8.
CN202311118192.1A 2023-08-31 2023-08-31 Carbazole-containing triarylamine compound and organic electroluminescent device thereof Pending CN117164567A (en)

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