CN112480136B - Heteroatom-bridged carbazole derivatives and uses thereof - Google Patents
Heteroatom-bridged carbazole derivatives and uses thereof Download PDFInfo
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Abstract
The invention relates to the technical field of materials for organic electroluminescent elements, in particular to heteroatom-bridged carbazole derivatives and application thereof; the structure of the heteroatom-bridged carbazole derivative is shown as the formula (I): the heteroatom-bridged carbazole derivative has higher triplet state energy level and high glass transition temperature, is suitable for being used as a material for an organic electroluminescent element, and the material for the organic electroluminescent element containing the heteroatom-bridged carbazole derivative has the characteristics of low starting voltage, high luminous efficiency and high brightness. In addition, the heteroatom-bridged carbazole derivative has good thermal stability and film-forming property, can prolong the service life when being applied to materials for organic electroluminescent elements, display devices and lighting devices, and can reduce the manufacturing cost of the materials for the organic electroluminescent elements, the display devices and the lighting devices.
Description
Technical Field
The invention relates to the technical field of materials for organic electroluminescent elements, in particular to a heteroatom-bridged carbazole derivative and application thereof.
Background
In recent years, organic electroluminescent display technologies have become mature, and some products have already entered the market, but in the course of industrialization, many problems still need to be solved, especially for various organic materials used for manufacturing devices, there are many problems that are still unsolved, such as carrier injection and transport properties, electroluminescent properties of materials, service life, color purity, matching between various materials and between various electrodes, and the like. Especially, the light emitting element has not yet achieved practical requirements in terms of luminous efficiency and service life, which greatly limits the development of OLED technology.
Organic electroluminescence is largely divided into fluorescence and phosphorescence, but according to the spin quantum statistical theory, the probability of singlet excitons and triplet excitons is 1. 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 in the prior art, the present invention provides a novel heteroatom-bridged carbazole derivative, which is used as a raw material for an organic electroluminescent element material and can provide an organic electroluminescent element material and an organic electroluminescent element having a reduced starting voltage, a high light-emitting efficiency, and an improved luminance.
In order to achieve the purpose, the invention adopts the following technical scheme:
a heteroatom-bridged carbazole derivative having the structure of formula (I):
wherein, X 1 ～X 4 Each is independently selected from N or CR;
R 1 ～R 9 the same or differentSelected from hydrogen, deuterium, having C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (A) having C 3 ～C 40 A branched or cyclic alkyl group having C 3 ～C 40 A branched or cyclic heteroalkyl group of (A) having C 2 ～C 40 Alkenyl or alkynyl group of (A), one of an aromatic ring system or a heteroaromatic ring system having 5 to 60 carbon atoms, R 1 ～R 9 Each of which may be substituted by 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 is selected from oxygen or sulfur;
each occurrence of R is the same or different and is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar) 1 ) 2 、N(R 10 ) 2 、C(＝O)Ar 1 、C(＝O)R 10 、P(＝O)(Ar 1 ) 2 Having a structure of C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (A) having C 3 ～C 40 A branched or cyclic alkyl group of (2), having C 3 ～C 40 A branched or cyclic heteroalkyl group of (2), having C 2 ～C 40 Or alkenyl or alkynyl, an aromatic or heteroaromatic ring system having from 5 to 80 carbon atoms, or an aryloxy or heteroaryloxy group having from 5 to 60 carbon atoms, each of the R groups being optionally substituted by one or more radicals R 10 Substituted, or combinations of these systems, wherein one or more non-adjacent-CH 2 The radicals may be substituted by R 10 C＝CR 10 、C≡C、Si(R 10 ) 2 、Ge(R 10 ) 2 、Sn(R 10 ) 2 、C＝O、C＝S、C＝Se、C＝NR 10 、P(＝O)(R 10 )、SO、SO 2 、NR 10 O, S or CONR 10 And wherein one or more hydrogen atoms are 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 ringOr a heteroaromatic ring system which may be substituted by one or more radicals R 10 Substitution;
R 10 each occurrence of the same or different is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar) 1 ) 2 、N(R 11 ) 2 、C(＝O)Ar 1 、C(＝O)R 11 、P(＝O)(Ar 1 ) 2 Having a structure of C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (A) having C 3 ～C 40 A branched or cyclic alkyl group having C 3 ～C 40 A branched or cyclic heteroalkyl group of (2), having C 2 ～C 40 Alkenyl or alkynyl, an aromatic or heteroaromatic ring system having from 5 to 60 carbon atoms, an aryloxy or heteroaryloxy group having from 5 to 60 carbon atoms, R 10 Each radical in (a) may be substituted by one or more radicals R 11 Substituted, or combinations of these systems, wherein one or more non-adjacent-CH 2 The radicals may be substituted by R 11 C＝CR 11 、C≡C、Si(R 11 ) 2 、Ge(R 11 ) 2 、Sn(R 11 ) 2 、C＝O、C＝S、C＝Se、C＝NR 11 、P(＝O)(R 11 )、SO、SO 2 、NR 11 O, S or CONR 11 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 10 Aliphatic, aromatic or heteroaromatic ring systems which may optionally be joined or fused to form a single ring or multiple rings and which may be interrupted by one or more radicals R 11 Substitution;
Ar 1 identical or different at each occurrence, from aromatic or heteroaromatic ring systems having from 5 to 30 carbon atoms which may be interrupted by one or more nonaromatic radicals R 11 Substitution; two groups Ar here bonded to the same nitrogen or phosphorus atom 1 Can also be selected from N (R) through a single bond 11 )、C(R 11 ) 2 Oxygen or sulfur bridging groups;
R 11 selected from the group consisting of hydrogen atoms, deuterium atoms,Fluorine atom, nitrile group, having C 1 ～C 20 An aromatic or heteroaromatic ring system having from 5 to 30 carbon atoms, wherein R 11 Wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups, wherein two or more adjacent substituents R 11 They can form mono-or polycyclic aliphatic, aromatic or heteroaromatic ring systems with one another.
An aromatic or heteroaromatic ring system in the sense of the present invention is intended to be taken to mean 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 with 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, and the like are also considered to refer to aromatic ring systems in the sense of the present invention.
Aryl in the sense of the present invention contains from 5 to 60 carbon atoms and heteroaryl in the sense of the present invention contains from 5 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 herein is 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 group, such as anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatic rings, such as biphenyl, which are connected to one another by single bonds, are, in contrast, not referred to as aryl or heteroaryl groups, but rather as aromatic ring systems.
Containing 1 to 40 carbon atoms and in which a single hydrogen atom or-CH 2 The aliphatic hydrocarbon radicals or alkyl or alkenyl or alkynyl radicals which may also be substituted by the abovementioned radicals are preferably to be understood as meaning 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, cyclohexyl, cycloheptyl, and the like,Butynyl, pentynyl, hexynyl, heptynyl or octynyl. Alkoxy, preferably alkoxy having from 1 to 40 carbon atoms, is to be understood as meaning methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptoxy, n-octoxy, cyclooctoxy, 2-ethylhexoxy, pentafluoroethoxy and 2, 2-trifluoroethoxy. Heteroalkyl is preferably alkyl having 1 to 40 carbon atoms, meaning that the individual hydrogen atoms or-CH 2 The radicals which may be substituted by oxygen, sulfur, halogen atoms, are understood to mean alkoxy, alkylthio, fluorinated alkoxy, fluorinated alkylthio, 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-trifluoroethylthio, vinyloxy, vinylthio, propenyloxy, propenylthio, butenylthio, butenyloxy, pentenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, 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 may be present 2 The 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 aromatic or heteroaromatic ring atoms according to the invention may in each case also be substituted by the abovementioned radicals R 11 Substituted aromatic or heteroaromatic ring systems, in particular radicals derived from: benzene, naphthalene, anthracene, benzanthracene, phenanthrenePyrene, pyrene,
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, isoindole, spirotriindene, spiroisotridenzene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo [5,6,6 ] indole]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, benzopyrazine, pyrimidine, benzopyrimidine, quinoxaline, 1, 5-diazaanthracene, 2, 7-diaza pyrene, 2, 3-diaza pyrene, 1, 6-diaza pyrene, 1, 8-diaza pyrene, 4, 5-diaza pyrene, 4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorrubine, 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.
Further, said X 1 ～X 4 Each independently selected from N or CR, and any two or more adjacent X 1 ～X 4 Not N at the same time; r 1 ～R 9 The same or different, selected from one of hydrogen, deuterium, aromatic ring system or heteroaromatic ring system with 5-60 carbon atoms, and the R is 1 ～R 9 Each of which may be substituted by 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.
Further, the heteroatom-bridged carbazole derivative mainly comprises the following structures CJHK 717-CJHK 860:
wherein, T is 1 Selected from-O-, -S-, or any of the following structures:
* -and-represent a bond.
Further, said X 1 ～X 4 Each independently selected from N or CR, and any two or more adjacent X 1 ～X 4 Not N at the same time; r 1 ～R 9 The same or different, selected from hydrogen, deuterium, an aromatic ring system or a heteroaromatic ring system having 5 to 60 carbon atoms; z is selected from oxygen or sulfur.
The invention provides the application of the heteroatom-bridged carbazole derivative in organic elements.
Meanwhile, the invention also provides application of the heteroatom bridged carbazole derivative in serving as a light-emitting layer material, a hole transport layer material, a hole blocking layer material or an encapsulation layer material in an organic element.
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 located between the first electrode and the second electrode, at least one of the organic layers comprising the heteroatom-bridged carbazole derivative described above.
An organic electroluminescent element comprising a first electrode, a second electrode and a plurality of organic layers between the first and second electrodes, at least one of the organic layers comprising the heteroatom-bridged carbazole derivative.
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 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. Particular preference is given to systems having three light-emitting layers, where the three layers can exhibit blue, green and red emission. If more than one light-emitting layer is present, at least one of these layers comprises, according to the invention, a heteroatom-bridged carbazole derivative as described in 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 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 -5 Pa, preferably less than 10 -6 Pa is applied by vapor deposition. However, the initial pressure may also be even lower, e.g. below 10 -7 Pa。
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 is -5 The material is applied under a pressure between Pa and 1 Pa. A particular example of this method is the organic vapour jet printing method, in which the material is applied directly through a nozzle and is therefore 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 obtained by appropriate substitution. These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are possible, in which, for example, one or more layers are applied 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 emission light element or a bottom emission light 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 elements of the present invention contains the heteroatom-bridged carbazole derivative 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 heteroatom-bridged carbazole derivative 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, an encapsulation layer, or a photorefractive layer.
Compared with the prior art, the invention has the beneficial effects that: the heteroatom-bridged carbazole derivative has higher triplet state energy level and high glass transition temperature, is suitable for being used as a material for an organic electroluminescent element, and the material for the organic electroluminescent element containing the heteroatom-bridged carbazole derivative has the characteristics of low starting voltage, high luminous efficiency and high brightness. In addition, the heteroatom-bridged carbazole derivative has good thermal stability and film-forming property, can prolong the service life when being applied to materials for organic electroluminescent elements, display devices and lighting devices, and can reduce the manufacturing cost of the materials for the organic electroluminescent elements, the display devices and the lighting devices.
Drawings
FIG. 1 is a schematic view of a bottom emission example of an organic electroluminescent device of the present invention;
FIG. 2 is a schematic view showing an example of top emission of an organic electroluminescent device of the present invention;
in the figure: 1. a substrate; 2. an anode; 3. a hole injection layer; 4. a hole transporting/electron blocking layer; 5. a light emitting layer; 6. a hole blocking/electron transporting layer; 7. an electron injection layer; 8. and a cathode.
Detailed Description
The following examples are intended to illustrate the invention but 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 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 test instruments and methods for performance testing of OLED materials and devices in the examples are as follows:
OLED element performance detection conditions:
luminance and chromaticity coordinates: testing by using a spectrum scanner Photoresearch PR-715;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: tested using NEWPORT 1931-C;
and (3) testing the service life: LTS-1004AC life test equipment was used.
Example 1
The preparation method of the compound CJHK739, for example, Z = O, comprises the following steps:
the first step is as follows: preparation of Compound Int-1
0.9mol of 8-fluoro-3, 4-dihydronaphthalene-1 (2H) -ketone, 1.0mol of p-chlorophenylhydrazine hydrochloride and 2000mL of absolute ethanol are heated, refluxed, stirred and reacted for 12 hours, cooled to room temperature, concentrated under reduced pressure and dried, added with 300mL of water for dilution, extracted by ethyl acetate, an organic phase is collected, dried, filtered, concentrated under reduced pressure and dried, and separated and purified by a silica gel column to obtain a compound Int-1 with the yield of 82%.
The second step: preparation of Compound Int-2
0.5mol of the intermediate Int-1 prepared in the first step is dispersed in 2000mL of xylene, heated to 100 ℃, 1.5mol of solid manganese dioxide is added in portions, stirred for reaction for 16 hours, cooled to room temperature, filtered, concentrated to dryness in filtrate, and then separated and purified by a silica gel column to obtain the intermediate Int-2 as a yellow solid with a yield of 90%.
The third step: preparation of Compound Int-3
50.0mmol of the intermediate Int-2 prepared in the second step is dissolved in 200mL of xylene, under the protection of nitrogen, 55.0mmol of o-methoxy bromobenzene, 0.5mmol of cuprous iodide and 120.0mmol of sodium tert-butoxide are added, and 0.2mmol of Pd is added 2 (dba) 3 And 1.0mL of a 10% tri-tert-butylphosphine toluene solution, heating to 110 ℃, stirring for reaction for 16 hours, cooling to room temperature, adding 50mL of water for dilution, extracting with dichloromethane, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a yellow solid intermediate Int-3 with the yield of 78%.
The fourth step: preparation of Compound Int-4
50.0mmol of the intermediate Int-3 prepared in the third step is dissolved in 200mL of dichloromethane, the temperature is reduced to 0 ℃ by using an ice salt bath under the protection of nitrogen, 55.0mmol of boron tribromide solution dissolved in dichloromethane is dropwise added, the mixture is stirred and reacted for 2 hours, the temperature is raised to room temperature, 50mL of saturated sodium bicarbonate aqueous solution is added, the mixture is extracted by dichloromethane, an organic phase is collected, the organic phase is dried and filtered, the filtrate is concentrated under reduced pressure to be dried, and then the mixture is separated and purified by using a silica gel column to obtain a yellow solid intermediate Int-4, wherein the yield is 96%.
The fifth step: preparation of Compound Int-5
50.0mmol of the intermediate Int-4 prepared in the fourth step is dissolved in 120mL of N, N-dimethylformamide, 0.1mol of anhydrous potassium carbonate and 1.0g of tetrabutylammonium chloride are added under the protection of nitrogen, the mixture is heated to 110 ℃ in an oil bath and stirred to react for 12 hours, the reaction solution is cooled to room temperature, the reaction solution is poured into 250mL of ice water solution, the filtration is carried out, a filter cake is washed by water, and the product is separated and purified by a silica gel column to obtain a yellow solid intermediate Int-5 with the yield of 85%.
And a sixth step: preparation of compound CJHK739 (Z = O)
10.0mmol of the intermediate Int-5 prepared in the above step was dissolved in 60mL of THF, 12.0mmol of (4- (4- (9-carbazole) -6-phenyl-1, 3, 5-triazin-2-yl) phenyl) boronic acid and 0.2mg of Pd132 catalyst were added, 25.0mmol of anhydrous potassium carbonate and 20mL of water were added, the mixture was stirred and refluxed for 12 hours, diluted with 50mL of water, extracted with dichloromethane, the organic phase was collected, dried, filtered, the filtrate was concentrated under reduced pressure to dryness, and then separated and purified by silica gel column to obtain CJHK739 (Z = O) as a yellow solid with a yield of 65%.
MS and of compound CJHK739 (Z = O) 1 The HNMR test results are as follows:
MS(MALDI-TOF)：m/z 704.2468[M+H] + ； 1 HNMR(δ、CDCl3)：8.53～8.51(2H,d)；8.35～8.31(2H,m)；8.26～8.22(4H,m)；8.10～8.08(2H,d)；7.96～7.92(3H,m)；7.66～7.62(3H,m)；7.55～7.48(3H,m)；7.45～7.37(7H,m)；7.07～7.05(1H,m)；6.82～6.78(2H,m)。
example 2
Preparation method of compound CJHK760 with Z = S, T 1 By way of example, = N-phenyl, comprising the steps of:
the first step is as follows: preparation of Compound Int-6
10.0mmol of intermediate Int-30 (prepared by replacing p-chlorophenylhydrazine hydrochloride in the first step with o-bromophenylhydrazine hydrochloride and o-methoxybromobenzene in the third step with o-bromophenylmethyl sulfide) was dissolved in 60mL of dry THF, and the solution was cooled to 0 ℃ in a liquid nitrogen bath under the protection of nitrogen, 12.0mmol of a 65% sodium hydride solid was added in portions, stirred for 1 hour, 12.0mmol of ethyl 3-bromopropionate was added dropwise, stirred for 1 hour, warmed to room temperature and reacted for 2 hours, 50mL of a dilute aqueous hydrochloric acid solution was added dropwise, stirred for 30 minutes, extracted with ethyl acetate, the organic phase was collected, dried, filtered, and the filtrate was concentrated under reduced pressure to dryness, separated and purified by a silica gel column to obtain intermediate Int-6, a yellow solid, and a yield of 92%.
The second step is that: preparation of Compound Int-7
10.0mmol of intermediate Int-6 is dissolved in 80mL of dry N, N-dimethylformamide, 20.0mmol of anhydrous potassium carbonate solid and 1.0mmol of potassium tert-butoxide are added under the protection of nitrogen, the temperature is raised to 120 ℃, the mixture is stirred and reacted for 6 hours, the reaction solution is cooled to room temperature, the reaction solution is poured into 200mL of water and stirred and reacted for 30 minutes, the reaction solution is filtered, a filter cake is washed by water and is separated and purified by a silica gel column, and the intermediate Int-7 is obtained as yellow solid with the yield of 87%.
The third step: compound CJHK760 (Z = S, T) 1 Preparation of = N-phenyl)
10.0mmol of the intermediate Int-7 prepared in the previous step was dissolved in 60mL of toluene, and 12.0mmol of (3- (9-phenylcarbazol-3-yl) phenyl) boronic acid, 20.0mmol of anhydrous potassium carbonate and 0.02mmol of Pd (PPh) were added under nitrogen protection 3 ) 4 Adding catalyst, adding 30mL ethanol and 30mL water, heating, refluxing, stirring, reacting for 8 hr, cooling to room temperature, adding 50mL water for dilution, extracting with dichloromethane, collecting lower organic phase, drying, filtering, concentrating the filtrate under reduced pressure, and separating and purifying the solid with silica gel column to obtain CJHK760 (Z = S, T = S, and K is C-H760) 1 = N-phenyl), yellow solid, yield 76%.
Compound CJHK760 (Z = S, T) 1 = N-phenyl) MS and 1 the HNMR test results are as follows:
MS(MALDI-TOF)：m/z 641.2067[M+H] + ； 1 HNMR(δ、CDCl3)：8.37～8.35(1H,d)；8.21～8.18(5H,m)；7.98～7.91(3H,m)；7.95～7.77(4H,m)；7.67～7.64(1H,d)；7.50～7.46(5H,m)；7.39～7.28(6H,m)；7.24～7.21(1H,m)；7.10～7.08(2H,m)。
example 3
Preparation of Compounds CJHK 717-CJHK 768 referring to the preparation methods of example 1 and example 2, compounds CJHK 717-CJHK 768 were prepared by replacing only the (4- (4- (9-carbazole) -6-phenyl-1, 3, 5-triazin-2-yl) phenyl) boronic acid of the sixth step in example 1 with a different boronic acid compound or replacing the (3- (9-phenylcarbazol-3-yl) phenyl) boronic acid of the third step in example 2 with a different boronic acid compound, with other experimental parameters being routinely adjusted.
Example 4
Preparation method of compound CJHK776, for example Z = O:
10.0mmol of intermediate Int-31 (prepared by replacing only p-chlorophenylhydrazine hydrochloride in the first step with phenylhydrazine hydrochloride and o-bromoanisole in the third step with 2, 6-dibromoanisole, see the preparation method of example 1) was dissolved in 60mL of toluene, and 12.0mmol of (3- (9-carbazolyl) phenyl) boronic acid, 25.0mmol of anhydrous sodium carbonate, 0.01mmol of Pd (PPh) were added under nitrogen protection 4 The catalyst, 30mL of ethanol and 20mL of water were heated, refluxed, stirred, reacted for 6 hours, cooled to room temperature, diluted with 50mL of water, extracted with toluene, the organic phase was collected, dried, filtered, the filtrate was concentrated under reduced pressure to dryness, and then separated and purified by a silica gel column to obtain CJHK776 (Z = O) as a yellow solid with a yield of 77%.
MS of compound CJHK776 (Z = O) and 1 the HNMR test results are as follows:
MS(MALDI-TOF)：m/z 549.1983[M+H] + ； 1 HNMR(δ、CDCl 3 )：8.24～8.21(2H,m)；8.12～8.10(2H,d)；7.94～7.92(1H,d)；7.76～7.74(1H,d)；7.62～7.60(1H,d)；7.53～7.48(2H,m)；7.40～7.33(6H,m)；7.31～7.24(5H,m)；7.12～7.06(3H,m)；6.96(1H,s)。
example 5
Preparation of the compounds CJHK769 to CJHK800 with reference to the preparation method of example 4, the compounds Z being oxygen were prepared by merely substituting the (3- (9-carbazolyl) phenyl) boronic acid in example 4 with a different boronic acid compound, or the compounds Z being sulfur were prepared by referring to the preparation method of example 2, and other experimental parameters were routinely adjusted to prepare the compounds CJHK769 to CJHK800.
Example 6
Preparation method of compound CJHK819 with Z = O and T 1 For example, = N-phenyl, comprising the steps of:
the first step is as follows: preparation of intermediate Int-8
10.0mmol of 9-phenyl-9H, 9'H-3,3' -bicarbazole is dissolved in 80mL of dry THF, the temperature is reduced to 0 ℃ by a liquid nitrogen bath under the protection of nitrogen, 12.0mmol of 65% sodium hydride solid is added in portions, the mixture is stirred and reacted for 1 hour, 12.0mmol of 2,4, 6-trichloro-5-methoxypyrimidine is added, the mixture is stirred and reacted for 1 hour after the temperature is raised to the room temperature and is reacted for 10 hours, 50mL of dilute hydrochloric acid aqueous solution is added dropwise, the mixture is stirred and reacted for 30 minutes, ethyl acetate is used for extraction, an organic phase is collected, dried and filtered, filtrate is concentrated under reduced pressure and dried, and is separated and purified by a silica gel column, and an intermediate Int-8, yellow solid is obtained, and the yield is 82%.
The second step is that: preparation of intermediate Int-9
10.0mmol of intermediate Int-8 was dissolved in 80mL of dry N-methylpyrrolidin-2-one, 15.0mmol of anhydrous potassium carbonate, 12.0mmol of intermediate 1-fluoro-11H-benzo [ a ] carbazole (prepared by the synthesis method of example 1), 1.0mmol of cuprous iodide and 10.0mmol of copper powder were added under nitrogen protection, the temperature was raised to 110 ℃ and the reaction was stirred for 8 hours, the mixture was cooled to room temperature, the reaction mixture was poured into 150mL of water, the reaction was stirred for 30 minutes, the mixture was filtered, the filter cake was washed with water and ethanol, and the mixture was separated and purified by a silica gel column to obtain intermediate Int-9 as a yellow solid with a yield of 68%.
The third step: preparation of intermediate Int-10
Dissolving 10.0mmol of intermediate Int-9 in 60mL of dry toluene, adding 20.0mmol of anhydrous potassium carbonate, 12.0mmol of phenylboronic acid, 0.01mmol of Pd132 catalyst, 30mL of ethanol and 20mL of water under the protection of nitrogen, heating to reflux, stirring, reacting for 12 hours, cooling to room temperature, filtering, washing a filter cake with water and ethanol, and separating and purifying by using a silica gel column to obtain intermediate Int-10 which is a yellow solid with the yield of 85%.
The fourth step: preparation of intermediate Int-11
Dissolving 10.0mmol of intermediate Int-10 in 80mL of dry dichloromethane, cooling to 0 ℃ with ice water bath under the protection of nitrogen, dropwise adding a solution of 15.0mmol of boron tribromide dissolved in dichloromethane, stirring for reaction for 2 hours, heating to room temperature, stirring for reaction for 2 hours, adding 50mL of saturated aqueous sodium bicarbonate solution, extracting with dichloromethane, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain intermediate Int-11 as a yellow solid with the yield of 92%.
The fifth step: compound CJHK819 (Z = O, T) 1 Preparation of = N-phenyl)
Dissolving 5.0mmol of intermediate Int-11 in 20mL of dry N, N-dimethylformamide, adding 10.0mmol of anhydrous potassium carbonate under the protection of nitrogen, heating to 120 ℃, stirring for reaction for 10 hours, pouring the reaction solution into 100mL of water, stirring for 30 minutes, filtering, washing a filter cake with water and ethanol, and separating and purifying by using a silica gel column to obtain a compound CJHK819 (Z = O, T) 1 = N-phenyl), yellow solid, yield 85%.
Compound CJHK819 (Z = O, T) 1 = N-phenyl) and 1 the HNMR test results are as follows:
MS(MALDI-TOF)：m/z 792.2781[M+H] + ； 1 HNMR(δ、CDCl 3 )：8.52～8.50(1H,d)；8.48(1H,s)；8.31～8.25(5H,m)；8.06～7.98(6H,m)；7.90～7.88(1H,d)；7.82～7.77(2H,m)；7.67～7.62(2H,m)；7.53～7.44(4H,m)；7.41～7.29(8H,m)；7.18～7.13(3H,m)。
example 7
Preparation of the compounds CJHK801 to CJHK860 referring to the preparation method of example 6, the compounds CJHK801 to CJHK860 of the formula I were prepared by substituting 2,4, 6-trichloro-5-methoxypyrimidine of the first step in example 6 with different halogeno-pyrimidines or pyrazines and routinely adjusting other experimental parameters.
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 compound C was used as a hole injection material, the compound D was used as a hole transport material, the compound G was used as an electron transport dopant material, and LiQ was used as an electron transport host material.
The compound
An organic electroluminescent element as a green light was produced by sequentially depositing an EL deposition machine manufactured by SNU corporation on ITO glass to produce a green light element.
Comparative example 2
The following compound E was used as a red host material, the following compound F was used as a red dopant material, the compound C was used as a hole injection material, the compound H was used as a hole transport material, the compound G was used as an electron transport dopant material, and LiQ was used as an electron transport host material.
The compound is
Red light elements were sequentially formed on ITO glass by evaporation using an EL evaporator manufactured by SNU corporation, and organic electroluminescent elements were formed as red light.
Test example 1
An organic electroluminescent element was prepared according to the method of comparative example 1 by replacing compound a in comparative example 1 with the compounds CJHK717 to CJHK860 of the present invention.
The results of measuring the properties of the obtained organic electroluminescent element are shown in Table 1, wherein the driving voltage (V), the current efficiency (LE), the color Coordinate (CIE), and the full width at half maximum (FWHM) were measured at a current density of 10mA/cm 2 The conditions were obtained and the voltage, LE, FWHM and LT90% were normalized to the reference.
TABLE 1 test results of device Properties
As can be seen from table 1, the driving voltage of the device prepared from the compound of the present invention is substantially equal to that of the device prepared from comparative example 1, but the current efficiency and LT90% lifetime performance of the device are significantly improved, especially the lifetime of the green device using CJHK739 as the host material is 2.4 times longer than that of the comparative device.
The properties of only some of the compounds in CJHK717 through CJHK860 are listed in Table 1, and the properties of other compounds are substantially identical to the structures of the compounds listed in the Table, and are not listed any more due to space limitations.
Test example 2
The organic electroluminescent element was prepared according to the method of comparative example 2 by replacing compound E in comparative example 2 with the compounds CJHK717 through CJHK860 of the invention.
The results of measuring the properties of the obtained element are shown in Table 2, in which the driving voltage (V), the current efficiency (LE), the color Coordinate (CIE), and the full width at half maximum (FWHM) were measured at a current density of 10mA/cm 2 The conditions were obtained and the voltage, LE, FWHM and LT90% were normalized to the reference.
TABLE 2 test results of device performance
As can be seen from the results of the device performance test in Table 2, the device fabricated by the compound of the present invention has a significantly reduced driving voltage, an improved current efficiency, and an initial luminance of 2000cd/cm at the device, compared to the device fabricated by the comparative example 2, especially CJHK853 2 The LT90% lifetime in the initial condition is 1.2 times that of the comparative element.
The properties of only some of the compounds in CJHK 717-CJHK 860 are listed in Table 2, and the properties of other compounds are substantially identical to the structures of the compounds listed in the Table, and are not listed due to space limitation.
As shown in fig. 1 and fig. 2, which are a schematic view of a bottom emission example of the organic electroluminescent device of the present invention and a schematic view of a top emission example of the organic electroluminescent device, respectively, the organic compound prepared by the present invention is contained in the light-emitting layer 5 or the hole transport layer 4.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that modifications and improvements can be made thereto without departing from the scope of the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (7)
1. A heteroatom-bridged carbazole derivative is characterized in that the heteroatom-bridged carbazole derivative is selected from one of the following structures CJHK 717-CJHK 860:
* -and-represent a connecting bond.
2. Use of a heteroatom-bridged carbazole derivative according to claim 1 in organic elements.
3. Use of a heteroatom-bridged carbazole derivative according to claim 1 as a light-emitting layer material, hole transport layer material, hole blocking layer material or encapsulation layer material in organic devices.
4. Use according to claim 2 or 3, wherein 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, wherein at least one of the organic layers comprises the heteroatom-bridged carbazole derivative of claim 1.
6. A display device comprising the organic electroluminescent element according to claim 5.
7. An illumination device comprising the organic electroluminescent element according to claim 5.
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