CN114773353A - Carbazole-containing eight-membered ring compound and application thereof - Google Patents

Carbazole-containing eight-membered ring compound and application thereof Download PDF

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CN114773353A
CN114773353A CN202210390906.3A CN202210390906A CN114773353A CN 114773353 A CN114773353 A CN 114773353A CN 202210390906 A CN202210390906 A CN 202210390906A CN 114773353 A CN114773353 A CN 114773353A
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carbazole
membered ring
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谢佩
张海威
徐先锋
王振宇
李利铮
李程辉
张昊
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Beijing Bayi Space LCD Technology Co Ltd
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Abstract

The present invention relates to an eight-membered ring compound containing carbazole, an organic electroluminescent element, a display device, and a lighting device. The carbazole-containing eight-membered ring compound has higher triplet energy level and high glass transition temperature, and is suitable for being used as a material for an organic electroluminescent element. The material for organic electroluminescent elements, which contains the carbazole-containing eight-membered ring compound, has the characteristics of low starting voltage, high luminous efficiency and high brightness. The compound of the present invention has excellent thermal stability and film-forming properties, and can be used for materials for organic electroluminescent elements, display devices, and lighting devices, and can prolong the service life thereof, thereby reducing the production costs of the materials for organic electroluminescent elements, the display devices, and the lighting devices.

Description

Carbazole-containing eight-membered ring compound and application thereof
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to an eight-membered ring compound containing carbazole, an organic electroluminescent element, a display device and a lighting device.
Background
In recent years, the organic electroluminescent display technology has become mature, some products have entered the market, but in the process of industrialization, many problems still need to be solved. In particular, various organic materials used for manufacturing elements have many problems that are not solved, such as carrier injection and transport properties, electroluminescent properties of the materials, service life, color purity, matching between various materials and between various electrodes, and the like. Especially, the light emitting device has not yet achieved practical requirements in terms of luminous efficiency and lifetime, which greatly limits the development of OLED technology.
Organic electroluminescence is largely divided into fluorescence and phosphorescence, but according to the spin quantum statistics theory, the probability of singlet excitons and triplet excitons is 1:3, i.e., the theoretical limit of fluorescence from radiative transition of singlet excitons is 25%, and the theoretical limit of fluorescence from radiative transition of triplet excitons is 75%. It is urgent to use 75% of the energy of the triplet excitons. Forrest et al in 1997 discovered that the phosphorescence electroluminescence phenomenon breaks through the limitation of 25% efficiency of the quantum efficiency of the organic electroluminescence material, and arouses people to pay extensive attention to the metal complex phosphorescence material. Since then, much research has been conducted on phosphorescent materials.
The present invention has been made in view of the above circumstances.
Disclosure of Invention
In order to solve the above problems of the prior art, the present invention provides a carbazole-containing eight-membered ring compound, an organic electroluminescent element, a display device, and a lighting device. The compound of the present invention is useful as a raw material for an organic electroluminescent element, and can provide a material for an organic electroluminescent element and an organic electroluminescent element which have a reduced activation voltage, a high luminous efficiency, and an improved luminance.
In order to achieve the purpose, the invention adopts the following technical scheme:
a carbazole-containing eight-membered ring compound having a structure represented by formula (I):
Figure BDA0003596893870000011
wherein R isa、Rb、Rc、Rd、R1、R2、R3、R4、R5、R6、R7、R8、R9The same or different, each independently selected from the group consisting of: hydrogen, deuterium, having C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (C)3～C40A branched or cyclic alkyl group of (2), having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40Any adjacent two or more substituents are optionally joined or fused to form a monocyclic or polycyclic ring, with or without C, N, O or S in the ring so formed;
and R isaAnd RbOr R iscAnd RdAt least one group is substituted by a group shown in a formula (II);
Figure BDA0003596893870000021
ring A represents R9A substituted or unsubstituted five-membered heterocyclic ring, wherein the heteroatom is selected from O, S or one or more of N, and the atoms on the five-membered heterocyclic ring are independently selected from heteroatoms;
Ar1selected from the group consisting of: substituted or unsubstituted C6～C60Aryl, substituted or unsubstituted C2～C60Heteroaryl, substituted or unsubstituted C6～C60Arylamino, substituted or unsubstituted C2～C60A heteroaryl amino group;
l represents a single bond, substituted or unsubstituted C6～C60Arylene, substituted or unsubstituted C2～C60A heteroarylene group;
-represents the bond connecting the substituent to N.
An aryl or aromatic group in the sense of the present invention contains 5 to 60 carbon atoms and a heteroaryl group in the sense of the present invention contains 2 to 60 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O or S. Aryl or heteroaryl here embraces monocyclic radicals and polycyclic systems. Polycyclic rings can have two carbons that are two contiguous rings or two or more rings in common, referred to as "fused," where at least one of the rings is aromatic, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryls, heterocyclics, and/or heteroaryls. In addition, multiple aryl or heteroaryl groups may also be connected by non-aromatic units such as C, N, O or S atoms, for example, as with systems in which two or more aryl groups are connected by, for example, a short alkyl group, such as fluorene, 9' -spirobifluorene, 9-diarylfluorene, triarylamine, diarylether, dibenzofuran, or dibenzothiophene, and the like.
The alkyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. As non-limiting examples thereof, there are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, and the like. Heteroalkyl means a hydrogen atom or-CH on an alkyl group2-substituted by at least one heteroatom selected from halogen, halogen substituted by a halogen atom, or a halogen atom,Nitrile group N, O, S or silicon, as non-limiting examples, difluoromethyl, trifluoromethyl, trifluoroethyl, pentafluoroethyl, nitrile, acetonitrile, methoxymethyl, methoxyethyl, trimethylsilyl, triisopropylsilyl and the like.
The alkenyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. As non-limiting examples thereof, there are vinyl, allyl, isopropenyl, 2-butenyl, and the like.
The alkynyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. As non-limiting examples thereof, there are ethynyl, 2-propynyl and the like.
In general, the cycloalkyl group, cycloalkenyl group according to the present invention means a monovalent functional group obtained by removing one hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. As non-limiting examples thereof, there may be mentioned cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, and the like, wherein one or more-CH groups2The radicals may be replaced by the radicals mentioned above; furthermore, one or more hydrogen atoms may also be replaced by deuterium atoms, halogen atoms or nitrile groups.
The heterocycloalkyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a non-aromatic hydrocarbon having an atomic number of 3 to 40. In this case, more than one carbon, preferably 1 to 3 carbons, in the ring is substituted with a heteroatom such as N, O or S. As non-limiting examples thereof, there are tetrahydrofuran, tetrahydrothiophene, morpholine, piperazine and the like.
The aryloxy group or heteroaryloxy group used in the present invention means a monovalent functional group represented by RO-, and R mentioned above is an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 5 to 60 carbon atoms. As non-limiting examples of such aryloxy or heteroaryloxy groups, there are phenoxy, naphthoxy, biphenyloxy, 2-pyridyloxy, 3-pyridyloxy, 4-pyridyloxy and the like.
The aryl or heteroaryl radicals according to the invention are, in particular, radicals derived from: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene,
Figure BDA0003596893870000032
Perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, terphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis-or trans-indenofluorene, cis-or trans-indenocarbazole, cis-or trans-indolocarbazole, triindene, isotridendene, spirotriindene, spiroisotridendene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo [5,6 ] indole, perylene, anthracene, phenanthrene, perylene]Quinoline, benzo [6,7 ]]Quinoline, benzo [7,8 ]]Quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxaloimidazole, oxazole, benzoxazole, naphthooxazole, anthraoxazole, phenanthroixazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, hexaazatriphenylene, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1, 5-diaza-thracene, 2, 7-diaza, 2, 3-diaza-pyrene, 1, 6-diaza-pyrene, 1, 8-diaza-pyrene, 4,5,9, 10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorescent red ring, naphthyridine, azacarbazole, benzocarbazine, carboline, phenanthroline, 1,2, 3-triazole, 1,2, 4-triazole, benzotriazole, 1,2, 3-oxadiazole, 1,2, 4-oxadiazole, 1,2, 5-oxadiazole, 1,3, 4-oxadiazole, 1,2, 3-thiadiazole, 1,2, 4-thiadiazole, 1,2, 5-thiadiazole, 1,3, 4-thiadiazole, 1,3, 5-triazine, 1,2, 4-triazine, 1,2, 3-triazine, tetrazole, 1,2,4, 5-tetrazine, 1,2,3, 4-tetrazine, 1,2,3, 5-tetrazine, purine, pteridine, indolizine, and benzothiadiazole, or a group derived from a combination of these systems.
As used herein, "a combination thereof" or "group" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can envision from the applicable list. For example, alkyl and deuterium can be combined to form a partially or fully deuterated alkyl; halogen and alkyl may combine to form haloalkyl substituents such as trifluoromethyl and the like; and halogen, alkyl, and aryl groups may be combined to form haloaralkyl groups.
Further, the carbazole-containing eight-membered ring compound is one of formula (I) -1 to formula (I) -6:
Figure BDA0003596893870000031
Figure BDA0003596893870000041
g is selected from O, S or NAr2；
Ar2Selected from the group consisting of: substituted or unsubstituted C6～C60Aryl, substituted or unsubstituted C2～C60Heteroaryl, substituted or unsubstituted C6～C60Arylamine, substituted or unsubstituted C2～C60A heteroaryl amine group.
Further, the carbazole-containing eight-membered ring compound is selected from the group consisting of the structures shown below:
Figure BDA0003596893870000042
Figure BDA0003596893870000051
the symbols used are as defined above.
According to an embodiment of the present invention, further, the Ra、Rb、Rc、Rd、R1、R2、R3、R4、R5、R6、R7、R8、R9Each independently of each otherIndependently selected from hydrogen or deuterium; ar (Ar)1Is substituted or unsubstituted C2～C60A heteroaryl group, said heteroaryl group containing at least one nitrogen atom.
Further, the heteroaryl is selected from the group consisting of the following groups II-1 to II-17:
Figure BDA0003596893870000052
Figure BDA0003596893870000061
wherein the content of the first and second substances,
Z1、Z2each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxy or carboxylate thereof, sulfonic or sulfonate thereof, phosphoric or phosphate thereof, C1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, C1-C60Alkoxy radical, C3-C60Cycloalkyl radical, C3-C60Cycloalkenyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Aryloxy, substituted or unsubstituted C6-C60An arylsulfonyl ether group, or a substituted or unsubstituted C2-C60Heterocyclic aryl groups;
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
T1representation O, S, CR’R' or NAr’；
R’R' are each independently selected from hydrogen, deuterium, C1～C60Alkyl of (C)1～C60With heteroalkyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Arylamino, or substituted or unsubstituted C2-C60Group consisting of heterocyclic aryl radicals, R’And R "may optionally be joined or fused to form one or more additional substituted or unsubstituted rings, with or without one or more heteroatoms N, P, B, O or S in the formed ring; preferably, R’R' is methyl, phenyl or fluorenyl;
Ar’is selected from the group consisting of C1～C60Alkyl of (C)1～C60Heteroalkyl group of (C)3～C60Cycloalkyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Condensed ring aryl, substituted or unsubstituted C6-C60Arylamino, or substituted or unsubstituted C2-C60Heterocyclic aryl groups; preferably, Ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;
Figure BDA0003596893870000062
represents a bond connecting the substituent and N.
Further, the carbazole-containing eight-membered ring compound is selected from one of the following structures represented by D253 to D438:
Figure BDA0003596893870000063
Figure BDA0003596893870000071
Figure BDA0003596893870000081
Figure BDA0003596893870000091
Figure BDA0003596893870000101
Figure BDA0003596893870000111
Figure BDA0003596893870000121
Figure BDA0003596893870000131
Figure BDA0003596893870000141
Figure BDA0003596893870000151
wherein each G-is independently selected from O-, S-, or one of the following structures:
Figure BDA0003596893870000152
and represents a bond.
The carbazole-containing eight-membered ring compound is used in a material for an organic electroluminescent element.
Further, the carbazole-containing eight-membered ring compound is applied to a light-emitting layer material, a hole transporting/hole blocking layer material or a capping layer material.
An organic electroluminescent element comprising a first electrode, a second electrode, a capping layer and at least one organic layer interposed between the first electrode and the second electrode, at least one of the organic layer or the capping layer comprising the carbazole-containing eight-membered ring compound.
The organic electroluminescent element includes a cathode, an anode, and at least one light-emitting layer. In addition to these layers, it may also comprise further layers, for example in each case one or more hole-injecting layers, hole-transporting layers, hole-blocking layers, electron-transporting layers, electron-injecting layers, exciton-blocking layers, electron-blocking layers and/or charge-generating layers. An intermediate layer having, for example, exciton blocking function can likewise be introduced between the two light-emitting layers. However, it should be noted that each of these layers need not be present. The organic electroluminescent device described herein may include one light emitting layer, or it may include a plurality of light emitting layers. That is, a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer. Particularly preferred are systems with three light-emitting layers, wherein the three layers can exhibit blue, green and red light emission. If more than one light-emitting layer is present, at least one of these layers comprises the carbazole-containing eight-membered ring compound of the invention according to the invention.
In the other layers of the organic electroluminescent element according to the invention, in particular in the hole transport layer and in the hole blocking layer and the thin-film encapsulation layer, all materials can be used in the manner generally used according to the prior art. A person skilled in the art will thus be able to use all materials known for organic electroluminescent elements in combination with the luminescent layer according to the invention without inventive effort.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are applied by means of a sublimation process in which the temperature in a vacuum sublimation apparatus is below 10-5Pa, preferably less than 10-6Pa is applied by vapor deposition. However, the initial pressure may also be even lower, e.g. below 10-7Pa。
Preference is likewise given to organic electroluminescent elements in which one or more layers are applied by means of an organic vapor deposition method or by means of carrier gas sublimation, where 10-5The material is applied under a pressure between Pa and 1 Pa. A particular example of such a process is the organic vapor jet printing processWherein the material is applied directly through a nozzle and is thus structured.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are produced from solution, for example by spin coating, or by means of any desired printing method, for example screen printing, flexographic printing, offset printing, photoinitiated thermal imaging, thermal transfer, ink-jet printing or nozzle printing. Soluble compounds, for example, are obtained by appropriate substitution of a compound of formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are possible, in which one or more layers are applied, for example, from solution and one or more further layers are applied by vapor deposition.
Further, the organic layer may further include one or more selected from an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer, a light emitting layer, and a light refraction layer.
The organic electroluminescent element of the present invention may be either a top-emitting or bottom-emitting element. The structure and the production method of the organic electroluminescent element of the present invention are not limited. The organic electroluminescent element prepared by the compound can reduce the starting voltage and improve the luminous efficiency and brightness.
A display device includes the organic electroluminescent element.
An illumination device comprising the organic electroluminescent element.
The material for organic devices of the present invention contains the carbazole-containing eight-membered ring compound of the present invention. The material for organic devices may be composed of the compound of the present invention alone or may contain other compounds.
The compound of the present invention contained in the material for an organic electroluminescent element of the present invention can be used as a host material. In this case, the material for an organic electroluminescent element of the present invention may contain another compound as a dopant.
The material for an organic electroluminescent element of the present invention can also be used as a material for a hole transport layer, an enhancement layer, a light-emitting layer, an electron transport layer, a charge generation layer, an electron blocking layer, a capping layer, or a photorefractive layer.
Compared with the prior art, the invention has the beneficial effects that:
the carbazole-containing eight-membered ring compound of the present invention is a novel carbazole structure having an eight-membered ring, and has a bipolar property of transporting electrons and holes. The carbazole-containing eight-membered ring compound is suitable for use as a material for an organic electroluminescent element, and the material for an organic electroluminescent element containing the carbazole-containing eight-membered ring compound has the characteristics of low starting voltage, high luminous efficiency and high brightness. In addition, the compound of the present invention has good thermal stability and film-forming properties, and can be used in materials for organic electroluminescent elements, display devices, and lighting devices to prolong the service life thereof, thereby reducing power consumption and manufacturing cost.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
Fig. 1 shows a schematic diagram of an organic light emitting device 100. The illustrations are not necessarily drawn to scale. The device 100 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, an emissive layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. The device 100 may be fabricated by sequentially depositing the described layers.
Fig. 2 shows a schematic view of an inverted organic light emitting device 200. The device comprises a substrate 201, a cathode 202, an emissive layer 203, a hole transport layer 204, and an anode 205. The device 200 may be prepared by sequentially depositing the described layers. Because the most common OLED devices have a cathode disposed over an anode, while device 200 has a cathode 202 disposed under an anode 205, device 200 may be referred to as an "inverted" organic light emitting device. In corresponding layers of the device 200, materials similar to those described with respect to the device 100 may be used. Fig. 2 provides one example of how some layers may be omitted from the structure of device 100.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the examples given herein without any inventive step, are within the scope of the present invention.
The following examples illustrate the performance of OLED materials and devices as follows:
OLED element performance detection conditions:
luminance and chromaticity coordinates: testing with a photosresearch PR-715 spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: tested using NEWPORT 1931-C;
and (3) life test: an LTS-1004AC life test apparatus was used.
Example 1
A process for the preparation of compound D254 comprising the steps of:
the first step is as follows: preparation of intermediate Int-1
Figure BDA0003596893870000171
22.0mmol of 2- (2-phenylboronic acid pinacol ester) indole, 20.0mmol of 4, 5-dibromocarbazole-9-carboxylic acid tert-butyl ester, 40.0mmol of anhydrous sodium carbonate, and 0.1mmol of Pd (PPh)3)4Adding catalyst, adding 80mL of toluene, 40mL of ethanol and 40mL of water, heating, refluxing and stirring for reaction for 8 hours under the protection of nitrogen, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain the catalystInt-1 as a yellow solid, yield: 77 percent.
The second step: preparation of intermediate Int-2
Figure BDA0003596893870000172
20.0mmol of Int-1 are dissolved in 120mL of toluene and 40.0mmol of sodium tert-butoxide and 0.1mmol of Pd are added under nitrogen protection2(dba)3And 0.2mmol of Xphos, heating to 100 ℃, stirring for reaction for 12 hours, cooling to room temperature, adding 50mL of 3N dilute hydrochloric acid aqueous solution, extracting with toluene, drying an organic phase, filtering, concentrating under reduced pressure to dryness, passing through a silica gel short column, eluting with toluene, and concentrating under reduced pressure to dryness to obtain a yellow solid, wherein the yield is as follows: 60 percent.
The third step: preparation of Compound D254
Figure BDA0003596893870000181
Dissolving 10.0mmol of intermediate Int-2 in 50mL of dry DMF, cooling to 0 ℃ with ice water bath under the protection of nitrogen, adding 12.0mmol of 65% sodium hydride solid in batches, stirring for reaction for 1 hour, adding 12.0mmol of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine, heating to 45 ℃, stirring for reaction for 12 hours, pouring the reaction solution into 250mL of ice water, filtering, washing a filter cake with water and ethanol, and separating and purifying by using a silica gel column to obtain a compound D254, a yellow solid, and the yield: 84%, MS (MALDI-TOF): m/z 588.2194[ M + H ]]+。
Example 2
A process for the preparation of compound D309 comprising the steps of:
the first step is as follows: preparation of intermediate Int-3
Figure BDA0003596893870000182
Referring to the first step synthesis of example 1, only the 2- (2-phenylboronic acid pinacol ester) indole of the first step of example 1 was replaced with 1- (2-phenylboronic acid pinacol ester) benzo [ d ] imidazole to obtain compound Int-3 as a yellow solid, yield: 82 percent.
The second step: preparation of intermediate Int-4
Figure BDA0003596893870000183
20.0mmol of Int-3 was dissolved in 120mL of toluene and 30.0mmol of sodium tert-butoxide and 0.1mmol of Pd were added under nitrogen2(dba)3And 0.4mL of 10% tri-tert-butylphosphine toluene solution, heating to 100 ℃, stirring for reaction for 12 hours, cooling to room temperature, adding 50mL of 3N dilute hydrochloric acid aqueous solution, extracting with toluene, drying the organic phase, filtering, concentrating under reduced pressure to dryness, passing through a short column of silica gel, eluting with toluene, concentrating under reduced pressure to dryness to obtain a yellow solid, and obtaining the yield: 74 percent.
With reference to the analogous synthetic methods described above, the following compounds were prepared:
Figure BDA0003596893870000191
Figure BDA0003596893870000201
the third step: preparation of Compound D309
Figure BDA0003596893870000202
Referring to the synthesis procedure of the third step of example 1, substituting only Int-2 of the third step of example 1 with Int-4, compound D309 was prepared as a yellow solid in yield: 86%, MS (MALDI-TOF): m/z 589.2154[ M + H ]]+。
With reference to the analogous synthetic procedures described above, the following compounds were prepared:
Figure BDA0003596893870000203
Figure BDA0003596893870000211
Figure BDA0003596893870000221
Figure BDA0003596893870000231
Figure BDA0003596893870000241
Figure BDA0003596893870000251
Figure BDA0003596893870000261
Figure BDA0003596893870000271
Figure BDA0003596893870000281
Figure BDA0003596893870000291
wherein each G is independently selected from O, S or NPh.
Example 3
Preparation of compound D388:
Figure BDA0003596893870000301
20.0mmol of Int-2 are dissolved in 60mL of toluene and 30.0mmol of sodium tert-butoxide, 24.0mmol of 2- (2-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine and 0.2mmol of Pd are added under nitrogen2(dba)3And 0.5mL of 10% tri-tert-butylphosphine toluene solution, heating to 100 ℃, stirring for reaction for 12 hours, cooling to room temperature, adding 20mL of water, extracting with toluene, drying the organic phase, filtering, concentrating under reduced pressure to dryness, passing through a silica gel short column, eluting with toluene-dichloromethane, and concentrating under reduced pressure to dryness to obtain a yellow solid, wherein the yield is as follows: 85 percent. MS (MALDI-TOF): m/z 664.2509[ M + H ]]+。
With reference to a similar synthetic procedure as in example 3 above, the following compounds were prepared:
Figure BDA0003596893870000302
Figure BDA0003596893870000311
Figure BDA0003596893870000321
Figure BDA0003596893870000331
Figure BDA0003596893870000341
wherein each G is independently selected from O, S or NPh.
Preparation of organic electroluminescent element
Comparative example 1
The following compound C was used as a hole injection material, compound D as a hole transport material, compound E as a red host material, compound F as a red dopant material, compound G as an electron transport dopant material, and LiQ as an electron transport host material.
Figure BDA0003596893870000342
The compound
Figure BDA0003596893870000343
Figure BDA0003596893870000344
The OLED comparative element 1 was prepared by sequentially depositing ITO glass by an EL deposition machine manufactured by DOV corporation.
Comparative example 2
The compound
Figure BDA0003596893870000345
Figure BDA0003596893870000346
An EL evaporator manufactured by DOV company is sequentially adopted to evaporate and plate on the ITO glass to manufacture an OLED contrast element 2;
the structure of B as the red light main body material is as follows:
Figure BDA0003596893870000351
test example 1
An OLED element was prepared in accordance with the procedure of comparative example 1, wherein the aforementioned Compound E was replaced with any one or more of the compounds D253 to D438 of the present invention, to prepare an organic electroluminescent element,
the element structure is as follows:
Figure BDA0003596893870000352
Figure BDA0003596893870000353
the organic electroluminescent element prepared by the above process was subjected to the following performance tests:
the driving voltage and current efficiency of the organic electroluminescent elements prepared in test example 1 and comparative examples 1 to 3 and the lifetime of the elements were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent element reached 1000cd/m2The current voltage is the driving voltage, and the current density at the moment is measured; the ratio of the brightness to the current density is the current efficiency; the LT 98% lifetime test is as follows: using a luminance meter at 1000cd/m2The luminance degradation of the organic electroluminescent element was measured to be 980cd/m by maintaining a constant current at luminance2Time in hours. The results are shown in Table 1.
TABLE 1 test results of the performance of each element
Figure BDA0003596893870000354
Figure BDA0003596893870000361
As is clear from table 1, when the carbazole-containing eight-membered ring compound of the present invention is used as a host material for an organic electroluminescent device, the current efficiency is improved, the lifetime is greatly improved, and the carbazole-containing eight-membered ring compound is a phosphorescent host material having excellent performance.
The compound B in comparative example 2 is different from the compound of the present invention in that the compound B does not contain a heterocyclic ring represented by ring a and has a weak conjugation ability as compared with a five-membered heterocyclic ring containing an unpaired electron, so that the compound of the present invention is superior to the compound B in both molecular film formation and charge transport, and therefore, charge transport in the element is more balanced and element performance is improved.
The properties of only some of the compounds in D253-D438 are listed in Table 1, and the properties of other compounds are substantially consistent with the data of the compounds listed in Table 1, and are not listed any more due to space limitation.
The above description is only for the specific embodiments of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention, and all the changes or substitutions should be covered within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the appended claims.

Claims (10)

1. A carbazole-containing eight-membered ring compound, characterized in that the carbazole-containing eight-membered ring compound has a structure represented by formula (I):
Figure FDA0003596893860000011
wherein R isa、Rb、Rc、Rd、R1、R2、R3、R4、R5、R6、R7、R8、R9The same or different, each independently selected from the group consisting of: hydrogen, deuterium, having C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group of (2), having C3～C40A branched or cyclic heteroalkyl group of (2), having C2～C40Any adjacent two or more substituents are optionally joined or fused to form a monocyclic or polycyclic ring, with or without C, N, O or S in the ring so formed;
and R isaAnd RbOr R iscAnd RdAt least one group is substituted by a group shown in a formula (II);
Figure FDA0003596893860000012
ring A represents R9A substituted or unsubstituted five-membered heterocyclic ring, wherein the heteroatom is selected from one or more of O, S or N, and the atoms on the five-membered heterocyclic ring are independently selected from heteroatoms;
Ar1selected from the group consisting of: substituted or unsubstituted C6～C60Aryl, substituted or unsubstituted C2～C60Heteroaryl, substituted or unsubstituted C6～C60Arylamine, substituted or unsubstituted C2～C60A heteroaryl amino group;
l represents a single bond, substituted or unsubstituted C6～C60Arylene, substituted or unsubstituted C2～C60A heteroarylene group;
-represents the bond of the substituent to N.
2. The carbazole-containing eight-membered ring compound according to claim 1, wherein the compound is selected from one or more of the group consisting of formula (I) -1 to formula (I) -6:
Figure FDA0003596893860000021
g is selected from O, S or NAr2；
Ar2Selected from the group consisting of: substituted or unsubstituted C6～C60Aryl, substituted or unsubstituted C2～C60Heteroaryl, substituted or unsubstituted C6～C60Arylamine, substituted or unsubstituted C2～C60A heteroaryl amino group;
Ra、Rb、Rc、Rd、R1、R2、R3、R4、R5、R6、R7、R8、R9has the same meaning as defined in claim 1.
3. The carbazole-containing eight-membered ring compound according to claim 1 or 2, wherein the compound is selected from the group consisting of the structures shown below:
Figure FDA0003596893860000031
Figure FDA0003596893860000041
g is selected from O, S or NAr2；
Ar2Selected from the group consisting of: substituted or unsubstituted C6～C60Aryl, substituted or unsubstituted C2～C60Heteroaryl, substituted or unsubstituted C6～C60Arylamine, substituted or unsubstituted C2～C60A heteroaryl amino group;
Ra、Rb、Rc、Rd、R1、R2、R3、R4、R5、R6、R7、R8、R9、L、Ar1has the same meaning as defined in claim 1.
4. The carbazole-containing eight-membered ring compound according to any one of claims 1 to 3, wherein R isa、Rb、Rc、Rd、R1、R2、R3、R4、R5、R6、R7、R8、R9Each independently selected from hydrogen or deuterium; ar (Ar)1Is substituted or unsubstituted C2～C60A heteroaryl group containing at least one nitrogen atom.
5. The carbazole-containing eight-membered ring compound according to any one of claims 1 to 4, wherein the heteroaryl group is selected from the group consisting of the following groups II-1 to II-17:
Figure FDA0003596893860000042
wherein, the first and the second end of the pipe are connected with each other,
Z1、Z2each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxy or carboxylate thereof, sulfonic or sulfonate thereof, phosphoric or phosphate thereof, C1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, C1-C60Alkoxy radical, C3-C60Cycloalkyl radical, C3-C60Cycloalkenyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Aryloxy, substituted or unsubstituted C6-C60An arylthioether group, or a substituted or unsubstituted C2-C60Heterocyclic aryl groups;
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
T1o, S, CR 'R "or NAr';
r 'and R' are each independently selected from hydrogen, deuterium, C1～C60Alkyl of (C)1～C60With heteroalkyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Arylamino, or substituted or unsubstituted C2-C60Heterocyclic aryl, R 'and R' may optionally be joined or fused to form one or more additional substituted or unsubstituted rings, with or without one or more heteroatoms N, P, B, O or S in the ring so formed; preferably, R', R "are methyl, phenyl or fluorenyl;
ar' is selected from C1～C60Alkyl of (C)1～C60Heteroalkyl of (a), C3～C60Cycloalkyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Condensed ring aryl, substituted or unsubstituted C6-C60Arylamino, or substituted or unsubstituted C2-C60Heterocyclic aryl groups; preferably, Ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;
Figure FDA0003596893860000051
represents a bond connecting the substituent and N.
6. A carbazole-containing eight-membered ring compound according to any one of claims 1 to 5, which is selected from one of the following structures:
Figure FDA0003596893860000052
Figure FDA0003596893860000061
Figure FDA0003596893860000071
Figure FDA0003596893860000081
Figure FDA0003596893860000091
Figure FDA0003596893860000101
Figure FDA0003596893860000111
Figure FDA0003596893860000121
Figure FDA0003596893860000131
Figure FDA0003596893860000141
wherein, G is selected from O, S or one of the following structures:
Figure FDA0003596893860000142
and represents a bond.
7. Use of the carbazole-containing eight-membered ring compound according to any one of claims 1 to 6 in a material for an organic element, wherein the carbazole-containing eight-membered ring compound is used in a material for an organic electroluminescent element.
8. An organic electroluminescent element comprising a first electrode, a second electrode, a capping layer and at least one organic layer interposed between the first electrode and the second electrode, wherein at least one of the organic layer or the capping layer comprises the carbazole-containing eight-membered ring compound according to any one of claims 1 to 6.
9. A display device comprising the organic electroluminescent element according to claim 8.
10. A lighting device comprising the organic electroluminescent element according to claim 8.
CN202210390906.3A 2022-04-14 2022-04-14 Carbazole-containing eight-membered ring compound and application thereof Pending CN114773353A (en)

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US20180309067A1 (en) * 2017-04-21 2018-10-25 Universal Display Corporation Organic electroluminescent materials and devices
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