CN112898323A - Compound, application thereof and organic electroluminescent device comprising compound - Google Patents

Compound, application thereof and organic electroluminescent device comprising compound Download PDF

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CN112898323A
CN112898323A CN201911222145.5A CN201911222145A CN112898323A CN 112898323 A CN112898323 A CN 112898323A CN 201911222145 A CN201911222145 A CN 201911222145A CN 112898323 A CN112898323 A CN 112898323A
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魏金贝
李国孟
曾礼昌
李熠烺
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Beijing Eternal Material Technology Co Ltd
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Abstract

The invention provides a compound, application thereof and an organic electroluminescent device comprising the compound, wherein the compound has a structure shown in a formula (I), and is used as a material of a light-emitting layer in the organic electroluminescent device; the organic electroluminescent device comprises a first electrode, a second electrode and an organic layer between the first electrode and the second electrode, wherein the organic layer contains any one or at least two of the compounds. The compound provided by the invention can further reduce the efficiency roll-off of the device and prolong the service life of the device on the premise of ensuring proper driving voltage.

Description

Compound, application thereof and organic electroluminescent device comprising compound
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a compound, application thereof and an organic electroluminescent device comprising the compound.
Background
Organic electroluminescent diodes (OLEDs) based on display and illumination have attracted much attention because of their advantages of self-luminescence, wide viewing angle, fast response time, low power consumption, large size, and flexibility. The device structure of OLEDs is often composed of various functional layers such as a transport layer, a barrier layer, and a light emitting layer, wherein a dye used for light emission directly determines the color purity of the device.
Although fluorescent materials have low luminous efficiency and high power consumption compared to phosphorescent materials, they have a long lifetime and good color purity. At present, the blue light device is still mainly a fluorescent device. The phosphorescent material contains heavy metals (e.g., iridium, platinum, etc.), and can emit light using triplet excitons, thereby having high efficiency and low power consumption. But it is expensive and not conducive to further development of industrialization. In the structure of the current commercial organic electroluminescent device, blue fluorescence is generally adopted together with red and green phosphorescent materials.
Recently, researchers at the university of Guanxi, Japan reported that a TADF (Thermally Activated Delayed Fluorescence) resonance type organic material DABNA-1(Adv. Mater.2016,28, 2777-2781J. Mater.chem.C,2019,7,3082-3089) containing no metal has a large aromatic skeleton and thus has a high Fluorescence quantum yield. Meanwhile, the compound has a certain resonance effect due to the B and N atoms. The compounds have the advantages of narrow spectrum, high color purity and the like. However, the reverse system crossing is slow due to the large difference between the singlet state energy level and the triplet state energy level, and in addition, the lowest unoccupied orbital level is deep, excitons are easy to be directly compounded on the dye, so that the efficiency roll-off is serious, and the service life of the device is short.
Figure BDA0002301147180000011
The existing organic electroluminescent materials still have a lot of room for improvement in luminescent properties, and there is a need to develop new luminescent material systems to meet the commercialization requirements, so that a wider variety of luminescent materials with higher performance are in need of development.
Disclosure of Invention
In view of the deficiencies of the prior art, it is an object of the present invention to provide a compound having the structure of formula (I):
Figure BDA0002301147180000021
in formula (I), A, B and C each independently represent an aromatic or heteroaromatic ring;
in the formula (I), Ra、RbAnd RnEach independently represents one of monosubstitution to maximum permissible substituent, and each independently is selected from deuterated or non-deuterated hydrogen, deuterated or non-deuterated C1-C12 alkyl, deuterated or non-deuterated C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silane group, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
in the formula (I), Ar1And Ar2Each independently selected from one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
in the formula (I), Ar1And RaOr the ring A is connected into a ring or not connected into a ring;
in the formula (I), Ar2And RbOr the ring B is connected into a ring or not connected into a ring;
in the formula (I), Ra、Rb、Rn、Ar1And Ar2At least one term of the formula (A) is a structure shown in the formula (A):
Figure BDA0002301147180000022
in the formula (A), R1And R2Each independently selected from deuterium atoms, chain alkyls of C1-C12, naphthenic bases of C3-C12, substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted heteroaryl of C3-C30,
in the formula (A), X is CR3R4Any one of O or S, the R3And R4Each independently selected from one of C1-C12 chain alkyl, C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl,
in the formula (A), n is 0 or 1; when n is 0, the meaning of R is1And R2Do not form a ring with each other; when n is 1, the meaning of R is1And R2Forming rings mutually;
the substituted substituent is any one of deuterium, halogen, C1-C10 alkyl, C2-C10 alkenyl, C1-C6 alkoxy, C6-C30 monocyclic aromatic hydrocarbon or fused ring aromatic hydrocarbon group, and C3-C30 monocyclic heteroaromatic hydrocarbon or fused ring heteroaromatic hydrocarbon group.
The C5-C20 may be C5, C6, C7, C8, C9, C10, C11, C12, C14, C16, C18, C20, etc.
The C4 to C20 may be C4, C5, C6, C7, C8, C9, C10, C11, C12, C14, C16, C18, C20, or the like.
The C1-C10 may be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.
The C2-C10 may be C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.
The C1-C6 may be C1, C2, C3, C4, C5, C6, etc.
The C1-C12 may be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, etc.
The C3-C10 may be C3, C4, C5, C6, C7, C8, C9, C10, etc.
The C6 to C30 may be C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, or the like.
The C9-C30 may be C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, etc.
The C3 to C30 may be C3, C4, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, or the like.
The C5 to C30 may be C5, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, or the like.
In the present invention, the maximum permissible substituent means that the number of the substituent is the maximum number of substitutions provided that the substituted group satisfies the chemical bond requirement, and illustratively, R to which the ring 1 can be bondedaNumber of (2)Can be one or more, and if ring A is selected from benzene rings, the maximum permissible substituents (namely 4) can be reached.
When the compound is designed, the B-N resonance type compound is used as a mother ring structure, and at least one structure in the compound is shown as the formula A, so that when the compound is used as a luminescent material and applied to an organic electroluminescent device, the efficiency roll-off of the device can be further reduced on the premise of ensuring proper driving voltage, and the service life of the device is prolonged.
The B-N resonance type compound has a strong rigid structure, and effectively reduces non-radiative transition energy loss caused by molecular vibration, rotation and the like, so that the compound has high fluorescence quantum yield. In addition, the resonance effect enables the HOMO and LUMO orbitals of the whole molecule to be separated obviously, and the characteristic of thermal activation delayed fluorescence is presented; in addition, at least one structure of formula A in the compound is substituted by alkyl, so that the molecular distance is further increased, quenching caused by molecular accumulation is reduced, the introduction of heavy atoms can further reduce the non-radiative transition of molecules, the efficiency roll-off is further reduced, and the service life of a device is further prolonged.
The compound has longer service life on the premise of ensuring that the device has proper driving voltage and efficiency, is suitable for being used as a luminescent material in an organic electroluminescent device, and can also be applied to the technical fields of optical sensors, solar cells, lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information labels and the like.
Preferably, each of A, B and C independently represents any one of monocyclic aromatic ring or fused aromatic ring of C5-C10, monocyclic heterocyclic ring or fused heterocyclic ring of C4-C10;
preferably, each of A, B and C is independently selected from any one of benzene ring, naphthalene ring or fluorene ring.
Preferably, the compound has the structure of formula (II):
Figure BDA0002301147180000041
in the formula (II), Ra、Rb、Rn、Ar1And Ar2Each independently having the same limitations as described above;
in the formula (II), Ar1Is connected with the ring 1 to form a ring or is not connected with the ring;
in the formula (II), Ar2Is connected with the ring 2 to form a ring or is not connected with the ring;
in the formula (II), Ra、Rb、Rn、Ar1And Ar2At least one term in the formula A is a structure shown in the formula A.
Preferably, the compound has any one of the structures of formulae (3-1) - (3-3):
Figure BDA0002301147180000042
in the formulae (3-1) to (3-3), the Ra、RbAnd RnEach independently having the same limitations as described above;
in the formulae (3-1) to (3-3), Rd、Rc、Rd’And Rc’Each independently represents a single substituent to the maximum permissible substituent, and each independently is selected from one of hydrogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
the substituted substituent is selected from any one of halogen, chain alkyl of C1-C12, C3-C12 cycloalkyl, alkoxy or thioalkoxy of C1-C6, aryl amino of C6-C30, heteroaryl amino of C3-C30, monocyclic aromatic hydrocarbon or fused ring aromatic hydrocarbon group of C6-C30, and monocyclic heteroaromatic hydrocarbon or fused ring heteroaromatic hydrocarbon group of C3-C30;
in the formula (3-1), Rd、Rc、Ra、RbAnd RnAt least one item in the structure is shown as formula A;
in the formula (3-2), Rd’、Rc、Ra、RbAnd RnAt least one item in the structure is shown as formula A;
in the formula (3-3), Rd’、Rc’、Ra、RbAnd RnAt least one term in the formula A is a structure shown in the formula A.
Preferably, said R isa、Rb、Rn、RdAnd RcEach independently selected from any one of hydrogen, C1-C12 chain alkyl and C3-C12 cycloalkyl.
Preferably, said R isa、RbAnd RnEach independently selected from any one of hydrogen, C1-C12 chain alkyl and C3-C12 naphthenic base.
Preferably, the C1-C12 chain alkyl and the C3-C12 cycloalkyl are selected from any one of the following groups:
Figure BDA0002301147180000051
preferably, n is 0.
Preferably, said R is1And R2Each independently selected from any one of C1-C12 chain alkyl or C3-C12 cycloalkyl.
Preferably, said R is1And R2Each independently selected from any one of C1-C8 chain alkyl or C3-C8 cycloalkyl.
Preferably, said R is1And R2Each independently selected from any one of a deuterium atom, a methyl group or an ethyl group, preferably a methyl group.
Preferably, the compound is selected from any one of the following M1-M140 structures:
Figure BDA0002301147180000052
Figure BDA0002301147180000061
Figure BDA0002301147180000071
Figure BDA0002301147180000081
Figure BDA0002301147180000091
Figure BDA0002301147180000101
Figure BDA0002301147180000111
the second purpose of the invention is to provide an application of the compound, which is used as a material of a light-emitting layer in an organic electroluminescent device.
It is a further object of the present invention to provide an organic electroluminescent device comprising a first electrode, a second electrode and an organic layer between the first electrode and the second electrode, the organic layer comprising any one of the compounds described in one of the objects or a combination of at least two of the compounds.
The organic electroluminescent device provided by the invention comprises a first electrode, a second electrode and an organic material layer positioned between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO) may be used2) And transparent conductive oxide materials such as zinc oxide (ZnO), and any combination thereof. When the first electrode is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and a combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as compounds shown below in HT-1 to HT-34; or any combination thereof.
Figure BDA0002301147180000121
Figure BDA0002301147180000131
Figure BDA0002301147180000141
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-34 described above, or one or more compounds of HI-1-HI-3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI-1-HI-3 described below.
Figure BDA0002301147180000142
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
According to different technologies, the luminescent layer material can be different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescent luminescent material, and the like. In an OLED device, a single light emitting technology may be used, or a combination of a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent host material may be selected from, but not limited to, the combination of one or more of BFH-1 through BFH-17 listed below.
Figure BDA0002301147180000143
Figure BDA0002301147180000151
The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may have a multilayer structure including at least one of an electron injection layer ((EIL)), an electron transport layer ((ETL)), and a hole blocking layer ((HBL)).
In a specific example, the electron transport layer material may be selected from, but is not limited to, a combination of one or more of ET-1 through ET-57 listed below.
Figure BDA0002301147180000152
Figure BDA0002301147180000161
Figure BDA0002301147180000171
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, a combination of one or more of the following compounds:
LiQ、LiF、NaCl、CsF、Li2O、Cs2CO3、BaO、Na、Li、Ca。
compared with the prior art, the invention has the technical progress that:
the compound provided by the invention takes a B-N resonance type compound as a mother ring structure, wherein the B-N resonance type compound has a stronger rigid structure, and the non-radiative transition energy loss caused by molecular vibration, rotation and the like is effectively reduced, so that the compound has higher fluorescence quantum yield. In addition, the resonance effect enables the HOMO and LUMO orbitals of the whole molecule to be separated obviously, and the characteristic of thermal activation delayed fluorescence is presented; in addition, at least one structure of formula A is adopted in the compound, the substitution of alkyl enables the molecular distance to be further increased, quenching caused by molecular accumulation is reduced, the introduction of heavy atoms can further reduce the non-radiative transition of molecules, the efficiency roll-off is further reduced, and the service life of a device is further prolonged; when the compound is used as a luminescent material for an organic electroluminescent device, the efficiency roll-off of the device can be further reduced and the service life of the device can be prolonged on the premise of ensuring proper driving voltage.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Compounds of synthetic methods not mentioned in the present invention are all starting products obtained commercially. Solvents and reagents used in the present invention, such as methylene chloride, petroleum ether, ethanol, tetrahydrofuran, N-dimethylacetamide, anhydrous magnesium sulfate, carbazole, benzimidazole and the like, can be purchased from domestic chemical product markets, such as reagents from national drug group, TCI, shanghai Bidi medicine, carbofuran, and the like.
The present invention will be described in detail by taking a plurality of specific examples as examples, and the compounds of the examples of the present invention can be synthesized by referring to the specific synthetic examples shown below, but it should be noted that the obtaining of the compounds is not limited to the synthetic methods and raw materials used in the present invention, and those skilled in the art can also select other methods or routes to obtain the novel compounds proposed in the present invention. The compounds of the present invention, for which no synthetic method is mentioned, are commercially available starting products or are prepared by the starting products according to known methods.
Analytical testing of intermediates and compounds in the present invention uses an abciex mass spectrometer (4000 QTRAP).
Preparation formula can be any one of the following three formulas:
Figure BDA0002301147180000181
Figure BDA0002301147180000191
in a specific embodiment, the synthesis can be prepared according to one of the above routes, and a person skilled in the art can select a specific route according to actual needs, which is not specifically limited herein; wherein R isa、Rb、Rc、RdAnd RnWith the same selection ranges as described above.
Preparation example 1
Synthesis of compound M1:
Figure BDA0002301147180000192
(1) preparation of Compound M1-1:
1, 3-dibromo-5 (isopropyl-2-d) benzene (27.7g, 100mmol), diphenylamine (41.7g, 250mmol), tris (dibenzylidene-BASE acetone) dipalladium (Pd) was added at room temperature2(dba)3) (0.92g, 1mmol), 2-dicyclohexylphosphine-2, 6-dimethoxybiphenyl (s-Phos) (0.82g, 2mmol), sodium tert-butoxide (24g, 250mmol), xylene (500ml) were charged in a 1L one-necked flask, replaced with nitrogen three times, and heated to 130 ℃ for reaction overnight. The reaction solution was cooled to room temperature, extracted with ethyl acetate, washed with a large amount of water, the organic phase was dried and concentrated to perform column chromatography (PE: DCM ═ 25:1) to obtain 38g of crude product, and heated and washed with n-hexane to obtain 36.4g of white solid with a yield of 79.9%. Mass spectrometric analysis determined molecular ion mass: 455.28 (theoretical value: 455.25).
(2) Preparation of Compound M1
M1-1(4.6g, 10mmol) was added to a 250ml three-necked flask, p-tert-butylbenzene (80ml) was added, the reaction system was cooled to-20 ℃ after stirring for 20 minutes, 15mmol of tert-butyllithium was added, and stirring was continued for 30 minutes while maintaining the low temperature. Then gradually heating to 90 ℃ and continuously heating for 3 h. Finally, the temperature of the reaction system is reduced to-20 ℃ again, boron tribromide (5.1g, 20mmol) is added under the protection of nitrogen, and diisopropylethylamine (13g, 80mmol) is added after stirring for 30 minutes. Finally, the reaction system is heated to 110 ℃ and reacted for 12 h. After the reaction was cooled to room temperature, the organic phase was spin-dried under reduced pressure. Ethyl acetate (200ml) was extracted three times, and the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase is concentrated with silica gel and subjected to column chromatography (PE: DCM 100:1) to give 1.3g of crude product, which is recrystallized from toluene/n-hexane to give 0.66g of yellow solid with a yield of 14.2%. Mass spectrometric analysis determined molecular ion mass: 463.20 (theoretical value: 463.23).
Preparation example 2
The only difference from preparation example 1 was that diphenylamine was replaced with an equimolar amount of bis (4- (methyl-d 3)) aniline to give product M3. Mass spectrometric analysis determined molecular ion mass: 531.35 (theoretical value: 531.37).
Preparation example 3
Product M11.
The only difference from preparation 1 is that diphenylamine is replaced by an equimolar amount of diphenylamine to give the product M11. Mass spectrometric analysis determined molecular ion mass: 767.35 (theoretical value: 767.36).
Preparation example 4
Synthesis of compound M53:
Figure BDA0002301147180000201
(1) preparation of Compound M53-1:
at room temperature, sym-tribromobenzene (31.2g, 100mmol), bis (4- (isopropyl-2-d) benzene) amine (81.7g, 320mmol), Pd2(dba)3(2.8g, 3mmol), s-Phos (1.2g, 3mmol), sodium tert-butoxide (33.6g, 350mmol), xylene (1200ml) were addedIn a 2L single-necked flask, nitrogen was replaced three times, and the mixture was heated to 130 ℃ to react overnight. The reaction was cooled to room temperature, extracted with ethyl acetate, washed with copious amounts of water, the organic phase dried and concentrated for column chromatography (PE: DCM ═ 30:1) to afford 56.2g of a white solid in 67.1% yield. Mass spectrometric analysis determined molecular ion mass: 837.58 (theoretical value: 837.59).
(2) Preparation of Compound M53
M53-1(8.4g, 10mmol) was added to a 500ml three-necked flask, p-tert-butylbenzene (150ml) was added, the reaction system was cooled to-20 ℃ after stirring for 20 minutes, 15mmol of tert-butyllithium was added, and stirring was continued for 30 minutes while maintaining the low temperature. Then gradually heating to 90 ℃ and continuously heating for 3 h. Finally, the temperature of the reaction system is reduced to-20 ℃ again, boron tribromide (5.1g, 20mmol) is added under the protection of nitrogen, and diisopropylethylamine (13g, 80mmol) is added after stirring for 30 minutes. Finally, the reaction system is heated to 110 ℃ and reacted for 12 h. After the reaction was cooled to room temperature, the organic phase was spin-dried under reduced pressure. Ethyl acetate (200ml) was extracted three times, and the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase is concentrated with silica gel and chromatographed (PE: DCM 40:1) to give 2.3g of crude product, which is recrystallized from toluene/n-hexane to give 1.1g of yellow solid with a yield of 13.0%. Mass spectrometric analysis determined molecular ion mass: 845.57 (theoretical value: 845.57).
Preparation example 5
Synthesis of compound M69:
Figure BDA0002301147180000202
(1) preparation of Compound M69-1:
to a 500mL single-necked flask, 3, 6-bis (isopropyl-2-d) carbazole (21.5g, 85mmol), 2-bromo-1, 3-difluorobenzene (7.7g, 40mmol), cesium carbonate (32.6g, 100mmol), N, N-dimethylformamide (350mL) were added at room temperature, and after 3 times of nitrogen substitution, the mixture was heated at 130 ℃ for reaction overnight. After the reaction is stopped, after the reaction product is cooled to room temperature, 500ml of water is added and stirred for 10min, a large amount of white solid is separated out, the filtration is carried out, the filter cake is boiled and washed by ethanol for 2h, the temperature is reduced, the filtration is carried out, 21.8g of white solid product is obtained, and the yield is 82.8%. Mass spectrometric analysis determined molecular ion mass: 658.27 (theoretical value: 658.29).
(2) Preparation of Compound M69
M69-1(6.6g, 10mmol) was added to a 500ml three-necked flask, p-tert-butylbenzene (100ml) was added, the reaction system was cooled to-20 ℃ after stirring for 20 minutes, 15mmol of tert-butyllithium was added, and stirring was continued for 30 minutes while maintaining the low temperature. Then gradually heating to 90 ℃ and continuously heating for 3 h. Finally, the temperature of the reaction system is reduced to-20 ℃ again, boron tribromide (5.1g, 20mmol) is added under the protection of nitrogen, and diisopropylethylamine (13g, 80mmol) is added after stirring for 30 minutes. Finally, the reaction system is heated to 110 ℃ and reacted for 12 h. After the reaction was cooled to room temperature, the organic phase was spin-dried under reduced pressure. Ethyl acetate (200ml) was extracted three times, and the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase is concentrated with silica gel and chromatographed (PE: DCM ═ 40:1) to give 2.4g of crude product, which is recrystallized from toluene/n-hexane to give 0.8g of yellow solid, 16.5% yield. Mass spectrometric analysis determined molecular ion mass: 588.37 (theoretical value: 588.36).
Preparation example 6
The only difference from preparation 5 was that 2-bromo-1, 3-difluorobenzene was replaced by an equimolar amount of 3, 5-dibromotert-butylbenzene to give product M76. Mass spectrometric analysis determined molecular ion mass: 644.43 (theoretical value: 644.42).
Preparation example 7
Figure BDA0002301147180000211
(1) Preparation of Compound M97-1:
to a 500mL single-necked flask were added 3, 6-bis (isopropyl-2-d) carbazole (21.5g, 85mmol), 5-bromo-2-chloro-1, 3-difluorobenzene (9.0g, 40mmol), cesium carbonate (32.6g, 100mmol), N, N-dimethylformamide (350mL) at room temperature, and after 3 times of replacement with nitrogen, the mixture was heated at 130 ℃ for reaction overnight. After the reaction is stopped, after the reaction product is cooled to room temperature, 500ml of water is added and stirred for 10min, a large amount of white solid is separated out, the filtration is carried out, the filter cake is boiled and washed by ethanol for 2h, the temperature is reduced, the filtration is carried out, 25.6g of white solid product is obtained, and the yield is 92.4%. Mass spectrometric analysis determined molecular ion mass: 692.23 (theoretical value: 692.25).
(2) Preparation of Compound M97-2:
m97-1(13.8g, 20mmol) o-fluorobenzeneboronic acid (3.1g, 22mmol), anhydrous potassium carbonate (4.14g, 30mmol), 15mL of water and 1, 4-dioxane (350mL) were sequentially added to a 500mL single-neck flask at room temperature, and after 3 times of nitrogen substitution, 800mg of palladium tetratriphenylphosphine was added and the reaction was heated at 120 ℃ overnight. After the reaction is stopped, cooling to room temperature, spin-drying the organic solvent of the reaction system, extracting with dichloromethane, and washing with a large amount of water. The organic phases were combined, dried and concentrated and then subjected to column chromatography to give 11.2g of a white solid product with a yield of 79.0%. Mass spectrometric analysis determined molecular ion mass: 708.32 (theoretical value: 708.36).
(3) Preparation of Compound M97
M97(7.1g, 10mmol) was added to a 500ml three-necked flask, p-tert-butylbenzene (100ml) was added, the reaction system was cooled to-20 ℃ after stirring for 20 minutes, 15mmol of tert-butyllithium was added, and stirring was continued for 30 minutes while maintaining the low temperature. Then gradually heating to 90 ℃ and continuously heating for 3 h. Finally, the temperature of the reaction system is reduced to-20 ℃ again, boron tribromide (5.1g, 20mmol) is added under the protection of nitrogen, and diisopropylethylamine (13g, 80mmol) is added after stirring for 30 minutes. Finally, the reaction system is heated to 110 ℃ and reacted for 12 h. After the reaction was cooled to room temperature, the organic phase was spin-dried under reduced pressure. Ethyl acetate (200ml) was extracted three times, and the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase is concentrated with silica gel and subjected to column chromatography (PE: DCM 40:1) to give 4.1g of crude product, which is recrystallized from toluene/n-hexane to give 2.3g of yellow solid, yield 33.7%. Mass spectrometric analysis determined molecular ion mass: 682.37 (theoretical value: 682.38).
Preparation example 8
The only difference from preparation example 7 was that o-fluorobenzeneboronic acid was replaced with an equimolar amount of 2, 6-difluorophenylboronic acid to give product M99. Mass spectrometric analysis determined molecular ion mass: 700.35 (theoretical value: 700.37).
Example 1
This example provides an organic electroluminescent device, which is prepared as follows:
ultrasonically treating a glass plate coated with an ITO (indium tin oxide) (thickness of 150nm) transparent conductive layer in a commercial cleaning agent, washing in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using a low-energy cationic beam;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to less than 1 × 10-5Pa, performing vacuum evaporation on the anode layer film to obtain HI-2 and HT-4 which are respectively used as a hole injection layer and a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is respectively 10nm and 40 nm;
vacuum evaporating BFH-4: M1(30nm, 5% wt) on the hole transport layer to form a luminescent layer of the organic electroluminescent device, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 30 nm; wherein, the '5% wt' refers to the doping proportion of the dye, namely the mass part ratio of the host material BFH-4 to M1 is 95: 5;
vacuum evaporating an electron transport layer material ET-34 of the device on the light emitting layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 30 nm;
LiF with the thickness of 0.5nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 150nm is used as a cathode of the device.
So that it has the following structure:
ITO(150nm)/HI-2(10nm)/HT-4(40nm)/BFH-4:M1(30nm,5wt％)/ET-34(30nm)/LiF(1nm)/Al(150nm)。
example 2
The difference from example 1 is that M1 was replaced with M3.
Example 3
The difference from example 1 is that M1 was replaced with M11.
Example 4
The difference from example 1 is that M1 was replaced with M53.
Example 5
The difference from example 1 is that M1 was replaced with M69.
Example 6
The difference from example 1 is that M1 was replaced with M76.
Example 7
The difference from example 1 is that M1 was replaced with M97.
Example 8
The difference from example 1 is that M1 was replaced with M99.
Example 9
The difference from embodiment 1 is that M1 is replaced with M111.
Example 10
The difference from embodiment 1 is that M1 is replaced with M114.
Comparative example 1
The difference from example 1 is that M1 is replaced by tBuDABNA.
Comparative example 2
The difference from example 1 is that M1 is replaced by R-1.
Figure BDA0002301147180000221
And (3) performance testing:
the driving voltage and current efficiency of the organic electroluminescent devices prepared in examples and comparative examples and the lifetime of the devices 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 device reached 1000cd/m2The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency; the life test of LT95 is as follows: using a luminance meter at 1000cd/m2The luminance drop of the organic electroluminescent device was measured to 950cd/m by maintaining a constant current at luminance2Time in hours.
The performance test results are shown in table 1:
TABLE 1
Figure BDA0002301147180000231
As can be seen from Table 1, the maximum current efficiency of the organic electroluminescent device in the examples is not less than 8.9cd/A and 1000cd/m2Powering offPressure less than or equal to 5.6V and 1000cd/m2Lower efficiency is more than or equal to 8.0cd/A and 1000cd/m2The lower service life is more than or equal to 56 h;
replacement of the luminescent material for the device of comparative example 1 with DABNA-1, maximum current efficiency and 1000cd/m2The lower efficiency and the service life are obviously deteriorated because the molecules have obvious nonradiative transitions such as vibration, rotation and the like;
the luminescent material of the device of comparative example 2 was changed to R-1, 1000cd/m2The lower efficiency and lifetime are significantly deteriorated because deuteration on the alkyl group is more advantageous to decrease non-radiative transition and improve the stability of the molecule.
The above results prove that when the compound provided by the invention is used as a luminescent layer material of an organic electroluminescent device, the efficiency and the service life of the device are improved, and excellent device performance is shown, because the compound provided by the invention takes a B-N conjugated system as a parent nucleus, and at least one structure shown as formula A in the compound is adopted, the stability of the device is obviously improved, which is beneficial to the practical application of the compound provided by the invention.
The applicant declares that the above description is only a specific embodiment of the present invention, but the scope of the present invention is not limited thereto, and it should be understood by those skilled in the art that any changes or substitutions that can be easily conceived by those skilled in the art within the technical scope of the present invention are within the scope and disclosure of the present invention.

Claims (12)

1. A compound having the structure of formula (I):
Figure FDA0002301147170000011
in the formula (I), ring A, ring B and ring C each independently represent an aromatic ring or a heteroaromatic ring;
in the formula (I), Ra、RbAnd RnEach independently represents a single substituent up to the maximum permissible substituent and each is independently selected from deuterated or non-deuterated hydrogen, deuterated or non-deuteratedOne of substituted C1-C12 chain alkyl, deuterated or non-deuterated C3-C12 cycloalkyl, deuterated or non-deuterated C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
in the formula (I), Ar1And Ar2Each independently selected from one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
in the formula (I), Ar1And RaAnd/or ring A is connected to form a ring or not connected to form a ring;
in the formula (I), Ar2And RbAnd/or ring B is connected to form a ring or not connected to form a ring;
in the formula (I), Ra、Rb、Rn、Ar1And Ar2At least one term of the formula (A) is a structure shown in the formula (A):
Figure FDA0002301147170000012
in the formula (A), R1And R2Each independently selected from deuterium atoms, chain alkyls of C1-C12, naphthenic bases of C3-C12, substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted heteroaryl of C3-C30,
in the formula (A), X is CR3R4Any one of O or S, the R3And R4Each independently selected from one of C1-C12 chain alkyl, C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl,
in the formula (A), n is 0 or 1;
the substituted substituent is selected from any one of halogen, chain alkyl of C1-C12, C3-C12 cycloalkyl, alkoxy or thioalkoxy of C1-C6, aryl amino of C6-C30, heteroaryl amino of C3-C30, monocyclic aromatic hydrocarbon or fused ring aromatic hydrocarbon group of C6-C30, and monocyclic heteroaromatic hydrocarbon or fused ring heteroaromatic hydrocarbon group of C3-C30.
2. The compound of claim 1, wherein each of A, B and C independently represents any one of a monocyclic aromatic ring or a fused aromatic ring of C5-C20, a monocyclic heterocyclic ring or a fused heterocyclic ring of C4-C20;
preferably, each of A, B and C independently represents any one of monocyclic aromatic ring or fused aromatic ring of C5-C10, monocyclic heterocyclic ring or fused heterocyclic ring of C4-C10;
preferably, each of A, B and C is independently selected from any one of benzene ring, naphthalene ring or fluorene ring.
3. The compound of claim 2, wherein the compound has the structure of formula (II):
Figure FDA0002301147170000021
in the formula (II), Ra、Rb、Rn、Ar1And Ar2Each independently having the same limitations as claim 1;
in the formula (II), Ar1And RaAnd/or ring 1 is connected to form a ring or not connected to form a ring;
in the formula (II), Ar2And RbAnd/or ring 2 is connected to form a ring or not connected to form a ring;
in the formula (II), Ra、Rb、Rn、Ar1And Ar2At least one term in the formula A is a structure shown in the formula A.
4. The compound of claim 3, wherein the compound has any one of the structures of formulas (3-1) - (3-3):
Figure FDA0002301147170000022
in the formulae (3-1) to (3-3), the Ra、RbAnd RnEach independently having the same limitations as claim 3;
in the formulae (3-1) to (3-3), Rd、Rc、Rd’And Rc’Each independently represents a single substituent to the maximum permissible substituent, and each independently is selected from one of hydrogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
the substituted substituent is selected from any one of halogen, chain alkyl of C1-C12, C3-C12 cycloalkyl, alkoxy or thioalkoxy of C1-C6, aryl amino of C6-C30, heteroaryl amino of C3-C30, monocyclic aromatic hydrocarbon or fused ring aromatic hydrocarbon group of C6-C30, and monocyclic heteroaromatic hydrocarbon or fused ring heteroaromatic hydrocarbon group of C3-C30;
in the formula (3-1), Rd、Rc、Ra、RbAnd RnAt least one item in the structure is shown as formula A;
in the formula (3-2), Rd’、Rc、Ra、RbAnd RnAt least one item in the structure is shown as formula A;
in the formula (3-3), Rd’、Rc’、Ra、RbAnd RnAt least one term in the formula A is a structure shown in the formula A.
5. A compound of claim 4, wherein R isa、Rb、Rn、Rd、Rc、Rd’And Rc’Each independently selected from any one of hydrogen, C1-C12 chain alkyl and C3-C12 cycloalkyl.
6. A compound according to claim 1 or 3, wherein R isa、RbAnd RnEach independently selected from any one of hydrogen, C1-C12 chain alkyl and C3-C12 naphthenic base.
7. The compound of claim 1,4, 5 or 6, wherein the C1-C12 chain alkyl group and the C3-C12 cycloalkyl group are selected from any one of the following groups:
Figure FDA0002301147170000031
8. a compound according to any one of claims 1,3 or 4, wherein n is 0.
9. A compound according to any one of claims 1,3 or 4, wherein R is1And R2Each independently selected from any one of C1-C12 chain alkyl or C3-C12 cycloalkyl;
preferably, said R is1And R2Each independently selected from any one of C1-C8 chain alkyl or C3-C8 cycloalkyl;
preferably, said R is1And R2Each independently selected from any one of a deuterium atom, a methyl group or an ethyl group;
preferably, said R is1And R2Is methyl.
10. The compound of claim 1, wherein the compound comprises any one of the following M1-M140 structures:
Figure FDA0002301147170000032
Figure FDA0002301147170000041
Figure FDA0002301147170000051
Figure FDA0002301147170000061
Figure FDA0002301147170000071
Figure FDA0002301147170000081
Figure FDA0002301147170000091
11. use of a compound according to any of claims 1-10 as a material for a light-emitting layer in an organic electroluminescent device.
12. An organic electroluminescent device comprising a first electrode, a second electrode and an organic layer between the first electrode and the second electrode, wherein the organic layer contains the compound according to any one of claims 1 to 10.
CN201911222145.5A 2019-12-03 2019-12-03 Compound, application thereof and organic electroluminescent device comprising compound Pending CN112898323A (en)

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