CN112442046B - Naphthalene bridged carbazole derivative and application thereof - Google Patents
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Abstract
The invention relates to the technical field of materials for organic electroluminescent elements, in particular to a naphthalene bridged carbazole derivative and application thereof. The structure of the naphthalene bridged carbazole derivative is shown as a formula (I), and the naphthalene bridged carbazole derivative has higher glass transition temperature and triplet energy level, is suitable for being used as a material for an organic electroluminescent element, and has the characteristics of low starting voltage, high luminous efficiency and high brightness.
Description
Technical Field
The invention relates to the technical field of materials for organic electroluminescent elements, in particular to a naphthalene bridged carbazole derivative and application thereof.
Background
In recent years, organic electroluminescent display technology has tended to mature, some products have been brought into the market, but in the industrialized time, there are still many problems to be solved, especially, various organic materials for manufacturing elements, such as carrier injection and transmission performance, electroluminescent performance, service life, color purity, matching between various materials and various electrodes, and the like, have not been solved. Especially, the light emitting element has not reached practical requirements in light emitting efficiency and service life, which greatly limits the development of OLED technology.
Organic electroluminescence is mainly classified into fluorescence and phosphorescence, but according to spin quantum statistics theory, the probability of singlet excitons and triplet excitons is 1:3, that is, the theoretical limit of fluorescence of radiative transition of singlet excitons is 25% and the theoretical limit of fluorescence of radiative transition of triplet excitons is 75%. How to use the energy of 75% of triplet excitons becomes urgent. The fact that the phosphorescence electroluminescence phenomenon breaks through the limit of 25% efficiency of the quantum efficiency of the organic electroluminescence material in 1997 is found by Forrest and the like, and the wide attention of people on the metal complex phosphorescence material is brought. Since then, a great deal of research has been conducted on phosphorescent materials.
The present invention has been made in view of the above-mentioned circumstances.
Disclosure of Invention
In order to solve the above problems in the prior art, the present invention provides a naphthalene bridged carbazole derivative, which is capable of providing a material for an organic electroluminescent element having a low starting voltage and a high luminous efficiency, and an organic electroluminescent element, as a raw material for the material for an organic electroluminescent element.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
a naphthalene bridged carbazole derivative, wherein the structural formula of the naphthalene bridged carbazole derivative is shown as formula (I):
wherein R is 1 ～R 13 The same or a different one of the above,selected from hydrogen, deuterium, and C 1 ～C 40 Straight chain alkyl of (C) 1 ～C 40 Straight chain heteroalkyl of (C) 3 ～C 40 Branched or cyclic alkyl of (C) 3 ～C 40 Branched or cyclic heteroalkyl having C 2 ～C 40 Alkenyl or alkynyl, aromatic or heteroaromatic ring systems having 5 to 60 carbon atoms, R 1 ～R 13 May be substituted with one or more groups R, and wherein two or more adjacent substituent groups may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system;
Z 1 selected from oxygen, sulfur or CR 14 R 15 ；
The R is 14 、R 15 Identical or different, selected from hydrogen, deuterium, having C 1 ～C 40 Straight chain alkyl of (C) 1 ～C 40 Straight chain heteroalkyl of (C) 3 ～C 40 Branched or cyclic alkyl of (C) 3 ～C 40 Branched or cyclic heteroalkyl having C 2 ～C 40 Alkenyl or alkynyl, aromatic or heteroaromatic ring systems having 5 to 60 carbon atoms, R 14 、R 15 May be substituted by one or more radicals R, and R 14 And R is 15 Aliphatic, aromatic or heteroaromatic ring systems which may optionally be joined or fused to form single or multiple rings;
the R is the same or different at each occurrence and is selected from hydrogen atom, deuterium atom, halogen atom, nitrile group, nitro group, N (Ar) 1 ) 2 、N(R 16 ) 2 、C(＝O)Ar 1 、C(＝O)R 16 、P(＝O)(Ar 1 ) 2 With C 1 ～C 40 Straight chain alkyl of (C) 1 ～C 40 Straight chain heteroalkyl of (C) 3 ～C 40 Branched or cyclic alkyl of (C) 3 ～C 40 Branched or cyclic heteroalkyl having C 2 ～C 40 Alkenyl or alkynyl of (a) having from 5 to 80 carbon atoms, an aromatic or heteroaromatic ring system,One of the aryloxy or heteroaryloxy groups having 5 to 60 carbon atoms, each of the R groups being optionally substituted by one or more radicals R 16 Substituted, or combinations of these systems, wherein one or more non-adjacent-CH' s 2 The radicals may be substituted by R 16 C＝CR 16 、C≡C、Si(R 16 ) 2 、Ge(R 16 ) 2 、Sn(R 16 ) 2 、C＝O、C＝S、C＝Se、C＝NR 16 、P(＝O)(R 16 )、SO、SO 2 、NR 16 O, S or CONR 16 Instead, and wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, wherein two or more adjacent substituents R may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more radicals R 16 Substitution;
R 16 is the same or different at each occurrence and is selected from hydrogen atom, deuterium atom, halogen atom, nitrile group, nitro group, N (Ar) 1 ) 2 、N(R 17 ) 2 、C(＝O)Ar 1 、C(＝O)R 17 、P(＝O)(Ar 1 ) 2 With C 1 ～C 40 Straight chain alkyl of (C) 1 ～C 40 Straight chain heteroalkyl of (C) 3 ～C 40 Branched or cyclic alkyl of (C) 3 ～C 40 Branched or cyclic heteroalkyl having C 2 ～C 40 Alkenyl or alkynyl, aromatic or heteroaromatic ring systems having 5 to 60 carbon atoms, aryloxy or heteroaryloxy having 5 to 60 carbon atoms, R 16 Each of which may be substituted by one or more radicals R 17 Substituted, or combinations of these systems, wherein one or more non-adjacent-CH' s 2 The radicals may be substituted by R 17 C＝CR 17 、C≡C、Si(R 17 ) 2 、Ge(R 17 ) 2 、Sn(R 17 ) 2 、C＝O、C＝S、C＝Se、C＝NR 17 、P(＝O)(R 17 )、SO、SO 2 、NR 17 O, S or CONR 17 Instead, and wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogenSubstituted by atoms, nitrile groups, or nitro groups, where two or more adjacent substituents R 16 Can optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system which can be substituted by one or more radicals R 17 Substitution;
Ar 1 and is identical or different on each occurrence and is selected from aromatic or heteroaromatic ring systems having from 5 to 30 carbon atoms, which may be substituted by one or more non-aromatic radicals R 17 Substitution; two radicals Ar bound to the same nitrogen or phosphorus atom 1 Or by single bond or selected from N (R) 17 )、C(R 17 ) 2 Bridging groups of oxygen or sulfur are bridged to each other;
R 17 selected from hydrogen atom, deuterium atom, fluorine atom, nitrile group, and C 1 ～C 20 An aliphatic hydrocarbon radical having from 5 to 30 carbon atoms, an aromatic or heteroaromatic ring system in which R 17 May be replaced by deuterium atoms, halogen atoms, or nitrile groups, wherein two or more adjacent substituents R 17 Aliphatic, aromatic or heteroaromatic ring systems which may be mono-or polycyclic with respect to one another.
An aromatic or heteroaromatic ring system in the sense of the present invention is intended to be understood as meaning a system which does not necessarily contain only aryl or heteroaryl groups, but in which a plurality of aryl or heteroaryl groups may also be linked by non-aromatic units, for example C, N, O or S atoms. Thus, for example, as well as systems in which two or more aryl groups are linked by, for example, a short alkyl group, systems such as fluorene, 9' -spirobifluorene, 9-diarylfluorene, triarylamine, diaryl ether, etc., are also considered to refer to aromatic ring systems in the sense of the present invention.
Aryl groups in the sense of the present invention contain 5 to 60 carbon atoms, heteroaryl groups in the sense of the present invention contain 5 to 60 carbon atoms and at least one heteroatom, provided 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 is herein considered to mean a simple aromatic ring, i.e. benzene, naphthalene, etc., or a simple heteroaromatic ring, such as pyridine, pyrimidine, thiophene, etc., or a fused aryl or heteroaryl, such as anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatic rings, for example biphenyls, which are linked to one another by single bonds are conversely not referred to as aryl or heteroaryl groups, but rather as aromatic ring systems.
Containing 1 to 40 carbon atoms and in which the hydrogen atoms or-CH are individually used in the sense of the invention 2 An aliphatic hydrocarbon radical, or an alkyl or alkenyl or alkynyl radical, the radicals of which may also be substituted by the radicals mentioned above, is preferably taken to mean the following radicals: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. Alkoxy is preferably an alkoxy group having 1 to 40 carbon atoms, which is taken to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octoxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2, 2-trifluoroethoxy. Heteroalkyl is preferably alkyl having from 1 to 40 carbon atoms, meaning a radical in which the individual hydrogen atoms or-CH 2-groups may be replaced by oxygen, sulfur, halogen atoms, is considered to mean alkoxy, alkylthio, fluoroalkoxy, fluoroalkylthio, in particular methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2-trifluoroethoxy 2, 2-trifluoroethylthio, ethyleneoxy, ethylenethio, propyleneoxy, propylenethio, butyleneoxy, pentyleneoxy, pentylenethio, cyclopentyleneoxy, cyclopentylenethio, hexyleneoxy, hexylenethio, cyclohexenyloxy, cyclohexenylthio, acetyleneoxy, acetylenethio, propynyloxy, propynylthioButynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, hexynylthio.
In general, cycloalkyl, cycloalkenyl groups according to the invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, wherein one or more-CH 2 The groups may be replaced by the groups described above; in addition, one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups.
The aromatic or heteroaromatic ring atoms according to the invention can in each case also be replaced by the abovementioned radicals R 17 Substituted aromatic or heteroaromatic ring systems, in particular groups derived from: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene,
Perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, benzine, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis-or trans-indenofluorene, cis-or trans-indenocarbazole, cis-or trans-indolocarbazole, triindene, isopolyindene, spiropolyindene, spiroisopolyindene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo [5,6 ]]Quinoline, benzo [6,7]Quinoline, benzo [7,8]Quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole, benzoxazole, naphthazole, anthracenoxazole, phenanthrooxazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, hexaazabenzophenanthrene, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1, 5-diazaanthracene, 2, 7-diazapyrene, 2, 3-diazapyrene, 1, 6-diazapyrene, 1, 8-diazapyrene, 4,5,9, 10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorored, naphthyridine, azacarboline, benzocarboline, carboline, phenanthroline, 1,2, 3-triazole, 1,2, 4-triazosinOxazole, 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 groups derived from combinations of these systems.
Further, the R 1 ～R 13 Identical or different, from the group consisting of hydrogen, deuterium, an aromatic or heteroaromatic ring system having from 5 to 60 carbon atoms, which ring system may be substituted by one or more groups R;
further, the Z 1 Selected from any one of the following structures:
wherein-and-represent a bond;
further, the structure of the naphthalene bridged carbazole derivative mainly comprises the following CJHK195-CJHK 341:
the T is 1 Each independently selected from-O-, S-, or any one of the following structures:
Z 1 each independently selected from-O-, S-, or any one of the following structures:
wherein-and-represent a bond.
The invention provides application of the naphthalene bridged carbazole derivative in materials for organic elements.
Meanwhile, the invention also provides application of the carbazole derivative in an organic element as a luminescent layer material, a hole transport layer material, a hole blocking layer material or an encapsulation layer material.
Further, the organic element is an organic electroluminescent element, an organic field effect transistor or an organic thin film solar cell.
An organic electroluminescent element comprising a first electrode, a second electrode, and a plurality of organic layers between the first electrode and the second electrode, at least one of the organic layers comprising the naphthalene-bridged carbazole derivative.
The organic electroluminescent element comprises 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-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, exciton-blocking layers, electron-blocking layers and/or charge-generating layers. An intermediate layer having, for example, an exciton blocking function can likewise be introduced between the two light-emitting layers. It should be noted, however, that not every one of these layers need be present. The organic electroluminescent element 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 is a system with three light-emitting layers, wherein the three layers can display blue, green and red light emission. If more than one light emitting layer is present, at least one of these layers comprises a naphthalene bridged carbazole derivative according to the present invention, according to the present 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 of ordinary skill in the art will thus be able to use all materials known in relation to organic electroluminescent elements in combination with the light-emitting layer according to the invention without inventive effort.
Furthermore, preference is given to organic electroluminescent elements in which one or more layers are applied by means of a sublimation process, wherein the sublimation process is carried out in a vacuum at a temperature of less than 10 -5 Pa, preferably below 10 -6 The material is applied by vapor deposition at an initial pressure of Pa. However, the initial pressure may also be even lower, for example below 10 -7 Pa。
Also preferred are 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 sublimationWherein at 10 -5 The material is applied at a pressure between Pa and 1 Pa. A particular example of this method is an organic vapor jet printing method, wherein the material is applied directly through a nozzle and is thus structured.
Furthermore, organic electroluminescent elements are preferred, from which one or more layers are produced, for example by spin coating, or by means of any desired printing method, for example screen printing, flexography, lithography, photoinitiated thermal imaging, thermal transfer, inkjet printing or nozzle printing. Soluble compounds, for example, are obtained by appropriate substitution. These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, a hybrid method is possible, in which one or more layers are applied, for example from a solution, and one or more further layers are applied by vapor deposition.
Further, the organic layer further comprises at least one 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 photorefractive layer.
The organic electroluminescent element of the present invention may be either a top-emission light element or a bottom-emission light element. The structure and the manufacturing 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.
A lighting device includes the organic electroluminescent element.
The material for organic elements of the present invention contains the naphthalene-bridged carbazole derivative of the present invention. The material for an organic element may be constituted by using the compound of the present invention alone or may contain other compounds together.
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 other compounds as doping materials.
The material for an organic electroluminescent element of the present invention may be used as a material for a hole transporting layer, an enhancement layer, a light emitting layer, an electron transporting layer, a charge generating layer, an electron blocking layer, an encapsulation layer, or a light refracting layer.
Compared with the prior art, the invention has the beneficial effects that: the naphthalene-bridged carbazole derivative has higher triplet energy level and high carrier mobility, is suitable for being used as a material for an organic electroluminescent element, and has the characteristics of low starting voltage, high luminous efficiency and high brightness. In addition, the compound of the invention has good thermal stability and film forming performance, and can prolong the service life when being applied to materials for organic electroluminescent elements, display devices and lighting devices, thereby reducing the manufacturing cost of the materials for organic electroluminescent elements, the display devices and the lighting devices.
Drawings
Fig. 1 is a schematic view of one bottom emission example of an organic electroluminescent device of the present invention;
fig. 2 is a schematic view of a top emission example of the organic electroluminescent device of the present invention;
in the figure: 1. a substrate; 2. an anode; 3. a hole injection layer; 4. a hole transport/electron blocking layer; 5. a light emitting layer; 6. a hole blocking/electron transport layer; 7. an electron injection layer; 8. and a cathode.
Detailed Description
The following examples are illustrative of the invention and are not intended to limit the scope of the invention.
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 will be apparent that the described embodiments are only some, but not all, embodiments of the invention. All other embodiments, based on the examples herein, which are within the scope of the invention as defined by the claims, will be within the scope of the invention as defined by the claims.
The test apparatus and method for testing performance of the OLED materials and devices in the following examples are as follows:
OLED element performance detection conditions:
luminance and chromaticity coordinates: photoresearch PR-715 was tested using a spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: using the NEWPORT 1931-C test;
life test: device for testing service life of AC (alternating current) by using LTS-1004
Example 1
The preparation method of the compound CJHK204 comprises the following steps:
Z 1 is oxygen or sulfur, T 1 Selected as C (CH) 3 ) 2 For example, CJHK 204-1:
the first step: preparation of Compound Int-1
20.0mmol of 2-bromo-6-methoxyaniline, 24.0mmol of m-chlorobenzeneboronic acid, 50.0mmol of anhydrous potassium carbonate and 0.2mmol of PdCl 2 (PPh) 2 Mixing, adding 75mL of N, N-dimethylformamide and 15mL of water, heating to 80 ℃ under the protection of nitrogen, stirring and reacting for 24 hours, cooling to room temperature, adding 200mL of water for dilution, filtering, washing a filter cake with water, and recrystallizing with ethanol to obtain the compound Int-1 with the yield of 94%.
And a second step of: preparation of Compound Int-1
20.0mmol of intermediate Int-1 and 22.0mmol of diphenyl sulfide are dissolved in 120mL of dichloromethane, the temperature is reduced to minus 15 ℃ by dry ice, 22.0mmol of NCS is added in batches, stirring reaction is carried out for 1 hour, stirring reaction is carried out for 2 hours at room temperature, 50mL of 25% sodium methoxide methanol solution is added, stirring reaction is carried out for 30 minutes, 50mL of water is added, stirring reaction is carried out at room temperature for 10 hours, an organic phase is separated, the aqueous phase is extracted by dichloromethane, the organic phase is collected, dried, filtered, the filtrate is concentrated to dryness under reduced pressure, and ethanol is used for recrystallization, thus obtaining the compound Int-2, and the yield is 86%.
And a third step of: preparation of Compound Int-3
15.0mmol of intermediate Int-2 is dissolved in 100mL of 1, 2-dichloroethane, 0.75mmol of rhodium acetate is added, the temperature is raised to 70 ℃ and the mixture is stirred for reaction for 5 hours, the mixture is cooled to room temperature, the mixture is filtered, a filter cake is collected, the filtrate is concentrated to dryness under reduced pressure, and the compound Int-3 is obtained by separating and purifying by a silica gel column, wherein the yield is 92%.
Fourth step: preparation of Compound Int-4
24.0mmol of 1-bromo-8-fluoronaphthalene, 20.0mmol of intermediate Int-3, 30.0mmol of sodium tert-butoxide and 0.2mmol of Pd 2 (dba) 3 And 0.4mmol of Xanphos are mixed, 80mL of toluene is added, the temperature is raised to 100 ℃ under the protection of nitrogen, stirring reaction is carried out for 12 hours, cooling is carried out to room temperature, 300mL of water is added for dilution, ethyl acetate is used for extraction, an organic phase is collected, drying, filtration and decompression concentration of filtrate are carried out, and purification is carried out by using a silica gel column, thus obtaining the compound Int-4 with 86 percent of yield.
Fifth step: preparation of Compound Int-5
20.0mmol of the intermediate Int-4 prepared in the previous step is dissolved in 120mL of dichloromethane, the temperature is reduced to minus 10 ℃ by using an ice salt bath under the protection of nitrogen, 22.0mmol of boron tribromide solution dissolved in the dichloromethane is dropwise added, stirring is carried out for 2 hours, 100mL of frozen dilute hydrochloric acid aqueous solution is added, an organic phase is collected, dried, filtered, the filtrate is concentrated under reduced pressure to dryness, and then the yellow solid compound Int-5 is obtained by separation and purification by using a silica gel column, wherein the yield is 95%.
Sixth step: preparation of Compound Int-6
20.0mmol of the intermediate Int-5 prepared in the previous step is dissolved in 100mL of N, N' -dimethylformamide, 40.0mmol of anhydrous potassium carbonate and 2.0mmol of copper powder are added under the protection of nitrogen, the temperature is raised to 130 ℃ and the mixture is stirred for reaction for 6 hours, the mixture is cooled to room temperature and filtered, the filtrate is poured into 500mL of ice water solution and filtered, a filter cake is washed with water and ethanol, and a silica gel column is used for separation and purification to obtain a yellow solid compound Int-6, and the yield is 84%.
Seventh step: preparation of Compound Int-7
10.0mmol of the intermediate Int-6 prepared in the previous step is dissolved in 50mL of dry THF, the temperature is reduced to-80 ℃ by liquid nitrogen under the protection of nitrogen, 4.8mL of 2.5M N-butyllithium N-hexane solution is added dropwise, stirring is carried out for 30 minutes, 15.0mmol of trimethyl borate solution dissolved in THF is added dropwise, stirring is carried out for 1 hour, the temperature is raised to room temperature, 20mL of 3N diluted hydrochloric acid aqueous solution is added, stirring is carried out for 30 minutes, ethyl acetate is used for extraction, an organic phase is collected, drying and filtration are carried out, the filtrate is concentrated to dryness under reduced pressure, petroleum ether is added for dispersion and filtration is carried out, thus obtaining the intermediate Int-7, white solid with the yield of 67%.
Eighth step: compound CJHK204-1 (Z) 1 Is oxygen, T 1 Is C (CH) 3 ) 2 ) Is prepared from
10.0mmol intermediate of the preparation from the previous stepBody Int-7 was dissolved in 60mL of toluene, and under nitrogen protection, 8.3mmol of N- (4-bromophenyl) -9, 9-dimethylfluorene-N-phenyl-2-amine, 20.0mmol of anhydrous potassium carbonate and 0.01mmol of Pd (PPh 3 ) 4 The catalyst, 30mL of ethanol and 30mL of water are added, the mixture is heated, refluxed and stirred for reaction for 8 hours, cooled to room temperature, 50mL of water is added for dilution, dichloromethane is used for extraction, the lower organic phase is collected, dried, filtered, the filtrate is concentrated to dryness under reduced pressure, and the solid is separated and purified by a silica gel column, so that the compound CJHK204-1 is obtained as a yellow solid with the yield of 82%.
MS and MS of Compound CJHK204-1 1 HNMR test results were as follows:
MS(MALDI-TOF)：m/z 667.2767[M+H] + ； 1 HNMR(δ、CDCl 3 )：8.29～8.27(1H,d)；8.03～7.98(4H,m)；7.92～7.86(4H,m)；7.59～7.47(6H,m)；7.41～7.31(5H,m)；7.25～7.04(7H,m)；6.45～6.43(1H,m)；1.68(6H,s)。
example 2
Z in the compounds CJHK195-CJHK 320, CJHK 331-CJHK 341 1 For the preparation of oxygen or sulfur compounds, referring to the preparation method of the compound CJHK204-1 in example 1, only the different halogenides were substituted for N- (4-bromophenyl) -9, 9-dimethylfluorene-N-phenyl-2-amine in the eighth step of example 1, and other experimental parameters were routinely adjusted to prepare the compounds CJHK195 to CJHK320, CJHK331 to CJHK341, wherein Z 1 A compound which is oxygen or sulfur.
Example 3
The preparation of compound CJHK219 comprises the steps of:
in Z 1 Selected as C (CH) 3 ) 2 For example, CJHK 219-1:
the first step: preparation of Compound Int-8
11.0mmol of ethyl 8-bromo-1-naphthoate is dissolved in 80mL of dry xylene, 10.0mmol of 3-chlorocarbazole and 20.0mmol of anhydrous potassium carbonate are added under the protection of nitrogen, 1.0mmol of cuprous iodide and 2.0mmol of N, N' -dimethylethylenediamine are added, the temperature is raised to 120 ℃ and stirred for reaction for 12 hours, the mixture is cooled to room temperature, filtered, the filtrate is concentrated to dryness under reduced pressure, and the intermediate Int-8 is obtained by separating and purifying by a silica gel column, and is yellow solid, and the yield is 92%.
And a second step of: preparation of intermediate Int-9
10.0mmol of intermediate Int-8 is dissolved in 80mL of dry THF, the temperature is reduced to 0 ℃ by an ice-water bath under the protection of nitrogen, 1.0mmol of anhydrous cerium trichloride is added, 30.0mmol of methyl magnesium bromide THF solution is added dropwise, the mixture is stirred and reacted for 1 hour, the mixture is cooled to room temperature and reacted for 12 hours, 50mL of 1N diluted hydrochloric acid aqueous solution is added dropwise, the mixture is extracted by ethyl acetate, an organic phase is collected, dried, filtered, the filtrate is concentrated to dryness under reduced pressure, and the intermediate Int-9 is obtained by separating and purifying by a silica gel column, and yellow solid is obtained with the yield of 90 percent.
And a third step of: preparation of intermediate Int-10
Under the protection of nitrogen, 10.0mmol of intermediate Int-9 is dissolved in 150mL of dichloromethane, the temperature is reduced to 0 ℃ by using an ice-water bath, 20.0mmol of boron trifluoride diethyl ether is added dropwise to the solution, the solution is stirred and reacted for 1 hour, the temperature is raised to room temperature, the reaction is stirred for 12 hours, 50mL of 10% sodium hydroxide aqueous solution is added dropwise, an organic phase is separated, the aqueous phase is extracted by dichloromethane, the organic phase is collected, dried, filtered, the filtrate is concentrated to dryness under reduced pressure, and the intermediate Int-10 is obtained by separating and purifying by using a silica gel column as yellow solid, and the yield is 96%.
Fourth step: preparation of intermediate Int-9
Referring to the preparation method of the seventh step of example 1, only intermediate Int-6 in the seventh step of example 1 was replaced with intermediate Int-10 to prepare intermediate Int-11 as a yellow solid in a yield of 76%.
Fifth step: compound CJHK219-1 (Z) 1 Is C (CH) 3 ) 2 ) Is prepared from
Referring to the preparation method of the eighth step of example 1, only the intermediate Int-7 of the eighth step of example 1 was replaced with the intermediate Int-11, and N- (4-bromophenyl) -9, 9-dimethylfluorene-N-phenyl-2-amine was replaced with N- ([ 1,1 '-biphenyl ] -4-yl) -N- (4-bromophenyl) - [1,1' -biphenyl ] -2-amine to prepare compound CJHK219-1 as a pale yellow solid in 83% yield.
MS and MS of Compound CJHK219-1 1 HNMR test results were as follows:
MS(MALDI-TOF)：m/z 729.3285[M+H] + ； 1 HNMR(δ、CDCl 3 )：8.27～8.24(2H,m)；7.95～7.93(2H,d)；7.72～7.65(4H,m)；7.62～7.51(5H,m)；7.48～7.42(3H,m)；7.36～7.30(6H,m)；7.26～7.16(5H,m)；6.96～6.94(2H,m)；6.90～6.86(5H,m)；1.76(3H,s)；1.64(3H,s)。
example 4
Z in the compounds CJHK195-CJHK 320, CJHK 331-CJHK 341 1 Is C (R) 14 R 15 ) With reference to the preparation of compound CJHK219-1 of example 3, only the different halogenides were substituted for N- ([ 1,1' -biphenyl) of the fifth step of example 3]-4-yl) -N- (4-bromophenyl) - [1,1' -biphenyl]2-amine, other experimental parameters were routinely adjusted to prepare the compounds CJHK195-CJHK 320, CJHK 331-CJHK 341, wherein Z 1 Is C (R) 14 R 15 ) Is a compound of (a).
Example 5
The preparation method of the compound CJHK322 comprises the following steps:
by T 1 And Z 1 The compound CJHK322-1 selected as oxygen is exemplified:
the first step: preparation of Compound Int-12
10.0mmol of 6-bromo-2-chlorodibenzo [ b, d ]]Furan was dissolved in 60mL of toluene, and under nitrogen protection, 11.0mmol of 3-methoxy-2-nitrobenzoic acid pinacol ester, 25.0mmol of anhydrous sodium carbonate and 0.01mmol of Pd (PPh) 3 ) 4 Adding 30mL of ethanol and 30mL of water into the catalyst, heating, refluxing, stirring, reacting for 8 hours, cooling to room temperature, adding 50mL of water for dilution, extracting with ethyl acetate, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying the solid by a silica gel column to obtain an intermediate Int-12, yellow solid, wherein the yield is 72%.
And a second step of: preparation of intermediate Int-13
8.0mmol of the intermediate Int-12 prepared in the first step is dissolved in 80mL of dimethylbenzene, 24.0mmol of tri (2, 4-di-tert-butylphenyl) phosphite is added under the protection of nitrogen, the mixture is heated and refluxed for 24 hours, cooled to room temperature, concentrated to dryness under reduced pressure, and separated and purified by a silica gel column to obtain the intermediate Int-13 as a yellow solid with the yield of 82%.
And a third step of: preparation of intermediate Int-14
Referring to the preparation method of the fourth step of example 1, the intermediate Int-14 was prepared by substituting Int-3 in the fourth step of example 1 with intermediate Int-13 in 83% yield as yellow solid.
Fourth step: preparation of intermediate Int-15
Referring to the preparation method of the fifth step of example 1, the intermediate Int-15 was prepared by substituting Int-4 in the fifth step of example 1 with intermediate Int-14 in 92% yield as yellow solid.
Fifth step: preparation of intermediate Int-16
Referring to the preparation method of the sixth step of example 1, the intermediate Int-16 was prepared by substituting the Int-5 of the sixth step of example 1 with the intermediate Int-15 in 89% yield as a yellow solid.
Sixth step: preparation of intermediate Int-17
Referring to the preparation method of the seventh step of example 1, the intermediate Int-17 was prepared by substituting Int-6 in the seventh step of example 1 with intermediate Int-16 in a yellow solid with a yield of 64%.
Fourth step: compound CJHK322-1 (T) 1 ＝Z 1 Preparation of =o)
Referring to the preparation method of the eighth step of example 1, only the intermediate Int-7 of the eighth step of example 1 was replaced with the intermediate Int-17, and N- (4-bromophenyl) -9, 9-dimethylfluorene-N-phenyl-2-amine was replaced with 2-chloro-4, 6-diphenyl-1, 3, 5-triazine, and other experimental parameters were routinely adjusted to prepare compound CJHK322-1 as a pale yellow solid in 85% yield.
MS and MS of Compound CJHK322-1 1 HNMR test results were as follows:
MS(MALDI-TOF)：m/z 629.1993[M+H] + ； 1 HNMR(δ、CDCl 3 )：9.28(1H,s)；8.35～8.32(4H,m)；7.87～7.85(3H,m)；7.77～7.75(2H,d)；7.67～7.52(7H,m)；7.45～7.41(2H,m)；7.20～7.16(2H,m)；7.08～7.04(2H,m)；6.89～6.86(1H,m)。
example 6
Preparation of Compounds CJHK321 to CJHK330 referring to the preparation method of example 5, different halides were substituted for the fourth step of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine of example 5, and other experimental parameters were routinely adjusted to prepare Compounds CJHK321 to CJHK330 of formula I.
Preparation of organic electroluminescent element
Comparative example 1
The following compound a was used as a green host material, the following compound B was used as a green dopant material, the following compound C was used as a hole injection material, the following compound D was used as a hole transport material, the following compound G was used as an electron transport dopant material, and LiQ was used as an electron transport host material.
Compound C
/D/>
/A+B(5％)/>
/LiQ+G(50％)/>
/LiF/>
Al (2 nm) was sequentially deposited on ITO glass using an EL evaporator manufactured by SNU corporation to prepare a green light element, and an organic electroluminescent element was prepared as green light.
Test example 1
An organic electroluminescent element was prepared in the same manner as in comparative example 1 except that compound A in comparative example 1 was replaced with the compounds CJHK195-CJHK341 of the present invention.
The results of performance measurements of the obtained organic electroluminescent elements are shown in Table 1, in which the driving voltage (V), current efficiency (LE), color Coordinates (CIE), full width at half maximum (FWHM) are shown at a current density of 10mA/cm 2 The conditions were found and the voltages, LE, FWHM and LT90% were data normalized to the reference element.
TABLE 1 results of component Performance test
As can be seen from Table 1, the organic material of the present invention produced a device having substantially the same driving voltage as that of the device produced in comparative example 1, but at 2000cd/cm 2 The device LT90% life under the initial condition is greatly improved, and particularly CJHK322-1 has good performance in terms of current efficiency and device life.
Only some of the properties of the compounds of CJHK195-CJHK341 are shown in Table 1, and other properties of the compounds are substantially identical to those of the structures of the compounds shown in the tables, and are not shown in one-to-one because of limited space.
Test example 2
An organic electroluminescent element was prepared in the same manner as in comparative example 1 except that compound D in comparative example 1 was replaced with the compounds CJHK195-CJHK341 of the present invention.
The results of the performance measurements of the resulting devices are shown in Table 2, wherein the driving voltage (V), current efficiency (LE), color Coordinates (CIE), full width at half maximum (FWHM) are shown at a current density of 10mA/cm for the devices 2 The conditions were found and the voltages, LE, FWHM and LT90% were data normalized to the reference element.
TABLE 2 results of component Performance test
As can be seen from the results of the device performance test in Table 2, the device prepared from the organic material of the present invention has significantly reduced driving voltage, high current efficiency, and significantly improved LT90% lifetime under the condition that the initial luminance of the device is 2000cd/cm2 as the initial, compared with the device prepared in comparative example 1, particularly CJHK 219-1.
Only the properties of some of the compounds CJHK195-CJHK341 are shown in Table 2, and the properties of other compounds are substantially identical to those of the structures of the compounds shown in the tables, and are not shown in one-to-one because of limited space.
As shown in fig. 1 and 2, which are respectively a schematic view of one bottom emission example of the organic electroluminescent device and a schematic view of one top emission example of the organic electroluminescent device of the present invention, the organic compound prepared according to the present invention is contained in the light emitting layer 5 or the hole transporting layer 4 or the hole blocking layer 6.
While the invention has been described in detail in the foregoing general description, embodiments and experiments, it will be apparent to those skilled in the art that modifications and improvements can be made thereto. Accordingly, such modifications or improvements may be made without departing from the spirit of the invention and are intended to be within the scope of the invention as claimed.
Claims (7)
1. A naphthalene bridged carbazole derivative, wherein the naphthalene bridged carbazole derivative has a structure selected from the group consisting of CJHK195-CJHK341 shown below:
the T is 1 Each independently selected from-O-, S-, or any one of the following structures:
Z 1 each independently selected from the group consisting of
Wherein-and-represent a bond.
2. Use of a naphthalene bridged carbazole derivative as claimed in claim 1 in organic elements.
3. Use of the carbazole derivative as claimed in claim 1 as light-emitting layer material, hole-transporting layer material, hole-blocking layer material or encapsulating layer material in organic components.
4. Use according to claim 2 or 3, characterized in that the organic element is an organic electroluminescent element, an organic field effect transistor or an organic thin film solar cell.
5. An organic electroluminescent element comprising a first electrode, a second electrode, and a plurality of organic layers between the first electrode and the second electrode, at least one of the organic layers comprising the naphthalene-bridged carbazole derivative according to claim 1.
6. A display device comprising the organic electroluminescent element as claimed in claim 5.
7. A lighting device comprising the organic electroluminescent element as claimed in claim 5.
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