CN111662317B - Organic compound and organic electroluminescent device - Google Patents
Organic compound and organic electroluminescent device Download PDFInfo
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Abstract
The disclosure provides an organic compound and an organic electroluminescent device, and belongs to the technical field of organic materials. The structure of the organic compound is shown as a formula I, and the organic compound can improve the performance of an organic electroluminescent device.
Description
Technical Field
The present disclosure relates to the field of organic materials, and in particular, to an organic compound and an organic electroluminescent device.
Background
An organic electroluminescent device generally includes an anode, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer, and a cathode, which are sequentially stacked. When voltage is applied to the anode and the cathode, the two electrodes generate an electric field, electrons on the cathode side move to the electroluminescent layer under the action of the electric field, holes on the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state and release energy outwards, so that the electroluminescent layer emits light outwards. .
The traditional electron transport material has low performance and is not very excellent in the application of organic electroluminescent devices. Therefore, development of materials with higher performance is required.
The above information disclosed in this background section is only for enhancement of understanding of the background of the disclosure and therefore it may contain information that does not form the prior art that is already known to a person of ordinary skill in the art.
Disclosure of Invention
An object of the present disclosure is to provide an organic compound and an organic electroluminescent device to improve the performance of the organic electroluminescent device.
In order to achieve the purpose, the technical scheme adopted by the disclosure is as follows:
according to a first aspect of the present disclosure, there is provided an organic compound having a structure represented by formula 1:
wherein, Y 1 、Y 2 、Y 3 Each independently selected from CH or N, and Y 1 、Y 2 、Y 3 At least one of which is N;
L 1 selected from single bond, n-carba-closo dodecaborane subunit;
Ar 1 、Ar 2 each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having a total number of carbon atoms of 6 to 20, a substituted or unsubstituted heteroarylene group having a total number of carbon atoms of 5 to 20;
R 1 to R 5 Each independently selected from hydrogen, deuterium, halogen, n-C-closed dodecaboryl, substituted or unsubstituted alkyl having from 1 to 20 total carbon atoms, substituted or unsubstituted cycloalkyl having from 3 to 20 total carbon atoms, substituted or unsubstituted heteroalkyl having from 2 to 20 total carbon atoms, substituted or unsubstituted alkenyl having from 2 to 20 total carbon atoms, substituted or unsubstituted aryl having from 6 to 30 total carbon atoms, substituted or unsubstituted heteroaryl having from 5 to 30 total carbon atoms, or R 1 And R 2 Atoms that are linked to each other to be commonly linked therewith form a ring;
Ar 1 、Ar 2 、R 1 to R 5 The substituents on the above groups are the same or different and are each independently selected from deuterium, halogen, n-substituted-closed dodecaboryl, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 6 carbon atoms, aryloxy having 6 to 12 carbon atoms, and silyl having 3 to 7 carbon atoms;
the structure of the organic compound shown in the formula 1 contains an n-substituted-closed dodecaborane group;
n in the n-carbon-closed dodecaborane subunit and the n-carbon-closed dodecaborane group is the number of boron atoms replaced by carbon atoms, and n is selected from any integer of 0-12.
According to a first aspect of the present disclosure, there is provided an organic electroluminescent device comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the organic compound of the first aspect.
The organic compound provided by the present disclosure connects a substituted fluorene group and a nitrogen-containing heterocycle, wherein C sp3 at position 9 of the substituted fluorene group is hybridized, which can increase the twist degree by connecting a ligand, thereby leading to increase of triplet excited state (T1). The higher T1 can limit excitons in the light-emitting layer, prevent energy from being transmitted to a surrounding functional layer, further promote a triplet-triplet fusion (TTF) effect, and improve the exciton utilization rate and the light-emitting efficiency. The lone pair electrons of the nitrogen atom in the nitrogen-containing heterocyclic ring do not participate in ring pi conjugation, and the electron-withdrawing ability is strong. And the nitrogen-containing heterocycle disclosed by the invention is in a planar configuration, and can form intermolecular or intramolecular hydrogen bonds under a specific condition, so that charge transfer can be effectively carried out, and the electron mobility is increased. In addition, the organic compound structure provided by the disclosure contains carbon-substituted closed dodecaborane, has a large three-dimensional structure and a large molecular weight, and can effectively improve the glass transition temperature of the material. In addition, the structure has large steric hindrance, so that the material is not easy to crystallize or gather, the material has a longer service life in the organic electroluminescent device, and the structure has a firm condensed ring structure, is not easy to lose electrons, has good chemical stability, is not easy to decompose in the long-time evaporation process of the material, and can further enhance the performance of the device.
Drawings
The above and other features and advantages of the present disclosure will become more apparent by describing in detail exemplary embodiments thereof with reference to the attached drawings.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present disclosure.
The reference numerals of the main elements in the figures are explained as follows:
100. an anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 321. a hole transport layer; 322. an electron blocking layer; 330. an organic electroluminescent layer; 340. a hole blocking layer; 350. an electron transport layer; 360. an electron injection layer.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying drawings. Example embodiments may, however, be embodied in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of example embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the disclosure.
In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals denote the same or similar structures in the drawings, and thus detailed descriptions thereof will be omitted.
The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the disclosure. One skilled in the relevant art will recognize, however, that the embodiments of the disclosure can be practiced without one or more of the specific details, or with other methods, components, materials, and so forth. In other instances, well-known structures, materials, or operations are not shown or described in detail to avoid obscuring the primary technical ideas of the disclosure.
The present disclosure provides an organic compound, the structure of which is shown in formula 1:
Y 1 、Y 2 、Y 3 each independently selected from CH or N, and Y 1 、Y 2 、Y 3 At least one of which is N;
L 1 selected from single bond, n-carba-closo dodecaborane subunit;
Ar 1 、Ar 2 each independently selected from a single bond, a substituted or unsubstituted arylene group having a total of 6 to 20 carbon atoms, a substituted or unsubstituted arylene group, aA heteroarylene group having 5 to 20 carbon atoms;
R 1 to R 5 Each independently selected from hydrogen, deuterium, halogen, n-substituted-closed dodecaboryl, substituted or unsubstituted alkyl of 1 to 20 total carbon atoms, substituted or unsubstituted cycloalkyl of 3 to 20 total carbon atoms, substituted or unsubstituted heteroalkyl of 2 to 20 total carbon atoms, substituted or unsubstituted alkenyl of 2 to 20 total carbon atoms, substituted or unsubstituted aryl of 6 to 30 total carbon atoms, substituted or unsubstituted heteroaryl of 5 to 30 total carbon atoms, or R 1 And R 2 Atoms that are linked to each other to be commonly linked therewith form a ring;
Ar 1 、Ar 2 、R 1 to R 5 The substituents on the above groups are the same or different and each is independently selected from deuterium, halogen, n-carbon-closed dodecaboryl, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 6 carbon atoms, aryloxy having 6 to 12 carbon atoms, and silyl having 3 to 7 carbon atoms;
the organic compound structure shown in the formula 1 contains an n-substituted-closed dodecaborane group;
n in the n-carba-closed dodecaborane subunit and the n-carba-closed dodecaborane group is the number of boron atoms replaced by carbon atoms, and n is selected from any integer of 0-12.
In the present disclosure, the n-carba-closed dodecaborane group includes n-carba-closed dodecaborane and n-carba-closed dodecaborane, and the structure of the organic compound shown in formula 1 includes one n-carba-closed dodecaborane group, which means that when L is L 1 In the case of n-carba-clododecenyl group, ar 1 、Ar 2 、R 1 To R 5 No n-substituted-closed dodecaboryl is contained in the structure of (A); when L is 1 When not n-substituted-closed dodecaborane units, ar 1 、Ar 2 、R 1 To R 5 Of which only one contains an n-carbon-closed dodecaborane group.
In the present disclosure, n in the n-carba-closo dodecaborane group, the n in the n-carba-closo dodecaborane group is the number of boron atoms replaced by carbon atoms, n is selected from any integer of 0 to 12, for example, n may be 0, 1,2, 3,4, 5, 6, 7, 8, 9,10, 11 and 12, preferably, n is selected from 1 or 2.
The organic compound of the present disclosure, which connects a substituted fluorene group and a nitrogen-containing heterocycle, wherein C sp3 at position 9 of the substituted fluorene group is hybridized, can increase the degree of torsion by connecting a ligand, thereby resulting in an increase in triplet excited state (T1). The higher T1 can limit excitons in the light-emitting layer, prevent energy from being transmitted to a surrounding functional layer, further promote a triplet-triplet fusion (TTF) effect, and improve the exciton utilization rate and the light-emitting efficiency. The lone pair electrons of the nitrogen atom in the nitrogen-containing heterocyclic ring do not participate in ring pi conjugation, and the electron-withdrawing ability is strong. And the nitrogen-containing heterocycle disclosed by the invention is in a planar configuration, and can form intermolecular or intramolecular hydrogen bonds under a specific condition, so that charge transfer can be effectively carried out, and the electron mobility is increased. In addition, the organic compound structure provided by the disclosure contains carbon-substituted closed dodecaborane, has a large three-dimensional structure and a large molecular weight, and can effectively improve the glass transition temperature of the material. In addition, the structure has large steric hindrance, so that the material is not easy to crystallize or gather, the material has a longer service life in the organic electroluminescent device, and the structure has a firm condensed ring structure, is not easy to lose electrons, has good chemical stability, is not easy to decompose in the long-time evaporation process of the material, and can further enhance the performance of the device.
In this disclosure Ar 1 、Ar 2 、R 1 To R 5 The total number of carbon atoms of (A) refers to all carbon atoms, for example, if L 1 The term "arylene group having 12 total carbon atoms" means that the number of all carbon atoms in the arylene group and the substituents thereon is 12.
N-substituted-closed dodecaboryl groups in the present disclosure may be represented by
Wherein X 1 To X 12 The same or different, each independently selected from C or B, when n =2, represents X 1 To X 12 Only two of them are C, the others are B. For example, when n =2,the n-substituted-closed dodecaborane group in the present disclosure is a dicarbo-closed dodecaborane group, and specifically may be
Where the unlabeled vertex is a BH. The same applies to the n-carba-closo dodecaborane subunit, which in the present disclosure is a dicarba-closo dodecaborane subunit, in particular £ er, when n =2>
Wherein, the marked vertexes are all BH.
In the present disclosure, aryl refers to an optional functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl group and a fused ring aryl group connected by carbon-carbon bond conjugation, two or more fused ring aryl groups connected by carbon-carbon bond conjugation. That is, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered an aryl group of the present disclosure. Wherein the aryl group does not contain a hetero atom such as B, N, O, S or P. For example, biphenyl, terphenyl, and the like are aryl groups in the present disclosure. Examples of the aryl group may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl a benzofluoranthenyl group,
A phenyl group, a fluorenyl group, and the like, without being limited thereto.
In the present disclosure, in the substituted or unsubstituted alkyl group having 1 to 20 total carbon atoms, the total carbon atoms of the alkyl group and the substituent thereon may be 1,2, 3,4, 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20. Preferably, the alkyl group is selected from alkyl groups having 1 to 6 carbon atoms, including, but not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, and hexyl.
In the present disclosure, in the substituted or unsubstituted cycloalkyl group having a total number of carbon atoms of 3 to 20, the total number of carbon atoms of the cycloalkyl group and the substituents thereon may be 3,4, 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20. The cycloalkyl group is selected from cycloalkyl groups having 3 to 10 carbon atoms, and specific examples include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, and the like.
In the present disclosure, in the substituted or unsubstituted alkenyl group having 2 to 20 total carbon atoms, the total carbon atoms of the alkenyl group and the substituents thereon are 2, 3,4, 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20. The alkenyl group may be vinyl, butadiene, etc.
In the present disclosure, substituted aryl refers to an aryl in which one or more hydrogen atoms are replaced with another group. For example, at least one hydrogen atom is substituted with a deuterium atom, F, cl, I, CN, hydroxyl, amino, branched alkyl, linear alkyl, cycloalkyl, alkoxy, amine, or other group. It is understood that a substituted aryl group having 18 carbon atoms refers to an aryl group and the total number of carbon atoms in the substituents on the aryl group being 18.
In the present disclosure, a substituted or unsubstituted aryl group having 6 to 30 total carbon atoms, wherein the total number of carbon atoms of the aryl group and substituents thereon may be 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30.
In the disclosure, the heteroaryl group may be a heteroaryl group including at least one of B, O, N, P, si and S as a heteroatom. The heteroaryl group can be monocyclic heteroaryl or polycyclic heteroaryl, in other words, the heteroaryl group can be a single aromatic ring system or a plurality of aromatic ring systems which are connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Exemplary heteroaryl groups may include, but are not limited to, thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzosilyl, dibenzofuranyl, phenyl-substituted dibenzofuranyl, dibenzofuranyl-substituted phenyl, and the like. Wherein, thienyl, furyl, phenanthroline and the like are heteroaryl of a single aromatic ring system, and N-aryl carbazolyl, N-heteroaryl carbazolyl, phenyl-substituted dibenzofuryl and the like are heteroaryl of a plurality of aromatic ring systems connected by carbon-carbon bond conjugation.
In the present disclosure, a substituted or unsubstituted heteroaryl group having a total number of carbon atoms of 5 to 30, wherein the total number of carbon atoms of the heteroaryl group and the substituents thereon may be 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30.
In the present disclosure, the explanation for aryl applies to arylene, and the explanation for heteroaryl applies equally to heteroarylene.
In the present disclosure, the halogen may be a fluorine atom, a chlorine atom, a bromine atom, an iodine atom.
In exemplary embodiments of the present disclosure, ar 1 、Ar 2 Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, and a substituted or unsubstituted terphenylene group.
In exemplary embodiments of the present disclosure, R 1 To R 5 Each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted aryl groups having a total number of carbon atoms from 6 to 20, substituted or unsubstituted heteroaryl groups having a total number of carbon atoms from 5 to 20.
Preferably, R 1 To R 5 Each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted phenyl group having a total number of carbon atoms from 6 to 20, a biphenylyl group having a total number of carbon atoms from 6 to 20, a terphenylyl group having a total number of carbon atoms from 6 to 20, a naphthyl group having a total number of carbon atoms from 6 to 20, a substituted or unsubstituted furyl group having a total number of carbon atoms from 5 to 20, a substituted or unsubstituted pyrrolyl group having a total number of carbon atoms from 5 to 20, and a substituted or unsubstituted imidazolyl group having a total number of carbon atoms from 5 to 20.
In exemplary embodiments of the present disclosure, R 1 、R 2 Each independently selected from hydrogen, n-substituted-closed dodecaboryl, substituted or unsubstituted aryl having a total number of carbon atoms of from 6 to 20, substituted or unsubstituted heteroaryl having a total number of carbon atoms of from 5 to 20, or R 1 Aromatic ring in the structure and R 2 The aromatic rings in the structure being linked to each other to form R 1 、R 2 The atoms that are commonly attached form a ring.
In exemplary embodiments of the present disclosure, ar 1 、Ar 2 Each independently selected from the group consisting of a single bond or:
wherein the content of the first and second substances,
represents a chemical bond.
In exemplary embodiments of the present disclosure, L 1 Selected from the group consisting of single bonds or the following groups:
wherein, the first and the second end of the pipe are connected with each other,
represents a chemical bond;
the vertices in the group labeled are all BH.
In this disclosureIn the first exemplary embodiment, R 1 To R 5 Each independently selected from hydrogen or a group consisting of:
wherein, the first and the second end of the pipe are connected with each other,
represents a chemical bond;
In exemplary embodiments of the present disclosure, the organic compound is selected from the group consisting of:
wherein the content of the first and second substances,
the unlabeled vertex in (1) is a BH.
The present disclosure also provides an organic electroluminescent device, including an anode and a cathode oppositely disposed, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises an organic compound of the present disclosure.
In exemplary embodiments of the present disclosure, the functional layer 300 includes an electron transport layer 350, and the electron transport layer 350 includes an organic compound provided by the present disclosure. The electron transport layer 350 may be composed of the organic compound provided in the present disclosure, or may be composed of the organic compound provided in the present disclosure and other materials.
In one embodiment of the present disclosure, the organic electroluminescent device may include an anode 100, a hole transport layer 321, an electron blocking layer 322, an organic electroluminescent layer 330 as an energy conversion layer, a hole blocking layer 340, an electron transport layer 350, and a cathode 200, which are sequentially stacked. The organic compound provided by the disclosure can be applied to the hole blocking layer 340 of the organic electroluminescent device, can effectively improve the luminous efficiency and the service life of the organic electroluminescent device, and reduces the driving voltage of the organic electroluminescent device.
In the disclosed exemplary embodiment, the anode 100 includes an anode material, which is preferably a material having a large work function (work function) that facilitates hole injection into the functional layer. Specific examples of the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metals and oxides, e.g. ZnO: al or SnO 2 Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole and polyaniline, but are not limited thereto. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.
Alternatively, the hole transport layer 321 may include one or more hole transport materials, and the hole transport material may be selected from carbazole multimers, carbazole-linked triarylamine-based compounds, or other types of compounds, which are not specifically limited by the present disclosure. For example, in one embodiment of the present disclosure, the hole transport layer 321 is composed of the compound NPB.
Alternatively, the organic light emitting layer 330 may be composed of a single light emitting material, and may also include a host material and a guest material. Alternatively, the organic light emitting layer 330 is composed of a host material and a guest material, and a hole injected into the organic light emitting layer 330 and an electron injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form an exciton, which transfers energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
The host material of the organic light emitting layer 330 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, and the disclosure is not particularly limited thereto. In one embodiment of the present disclosure, the host material of the organic light emitting layer 330 is compound 2.
The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, and the disclosure is not particularly limited thereto. In one embodiment of the present disclosure, the guest material of the organic light emitting layer 330 is compound 1.
Optionally, the cathode 200 comprises a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multilayer material such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 But not limited thereto,/Ca. Preferably, a metal electrode comprising aluminum is included as a cathode.
Optionally, as shown in fig. 1, a hole injection layer 310 may be further disposed between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which is not limited in this disclosure. In one embodiment of the present disclosure, the hole injection layer 310 may be composed of HAT-CN.
Optionally, as shown in fig. 1, an electron injection layer 360 may be further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic material. In one embodiment of the present disclosure, the electron injection layer 360 may include LiF.
Optionally, an electron blocking layer 322 may be further disposed between the organic electroluminescent layer 330 and the hole transport layer 321.
Hereinafter, the present disclosure will be described in further detail by examples. However, the following examples are merely illustrative of the present disclosure and do not limit the present disclosure.
Synthesis of compounds
Synthesis of Compound A-2 and Compound B-1
Adding o-carborane into a three-neck flask, introducing nitrogen, adding a certain amount of tetrahydrofuran, cooling to-80 ℃, slowly dropping n-butyl lithium ethane solution, and stirring. Subsequently, a cuprous chloride solution, and a certain amount of palladium acetate, trimethoxy triphenylphosphine (L2), and intermediate 1-1 dissolved in tetrahydrofuran were added, and stirring was performed at room temperature, followed by addition of water and chloroform for extraction. The separated organic layer was dried and subjected to column chromatography, and recrystallization was performed to obtain the product intermediate 1-2. And (3) putting the intermediate 1-2, the bis-diboron and the potassium acetate into 1, 4-dioxane, adding palladium dibenzylidene acetone and tricyclohexyl phosphine under the condition of refluxing and stirring, and stirring until the reaction is finished. Water and chloroform were added at room temperature for extraction, and after separation, drying and distillation were performed, and recrystallization was performed to obtain intermediate 2-2. Then, the intermediate 2-2 and the intermediate 2-3 are dissolved in a certain amount of tetrahydrofuran solution, and potassium carbonate aqueous solution and tetrakis (triphenylphosphine) palladium are added, heated and stirred until the reaction is finished, and after the solvent is removed, recrystallization is performed to obtain the compound a-2.
Compound B-1 was synthesized in the same manner as Compound A-1 except that intermediate 3-1 was used instead of intermediate 1-1.
Synthesis of Compound D-2 and Compound D-5
Adding m-carborane into a three-neck flask, introducing nitrogen, adding a certain amount of tetrahydrofuran, cooling to-80 ℃, slowly dropping n-butyl lithium ethane solution, and stirring. Subsequently, a cuprous chloride solution, and a certain amount of palladium acetate, trimethoxy triphenylphosphine (L2), and intermediate 4-1 dissolved in tetrahydrofuran were added, and stirring was performed at room temperature, followed by addition of water and chloroform for extraction. The separated organic layer was dried and subjected to column chromatography, and recrystallization was performed to obtain the simplified 4-2 in the product. Subsequently, the subsequent reaction was continued in the same manner to obtain compound D-2.
Compound D-5 was synthesized in the same manner as compound D-2 except that intermediate 5-1 was used instead of intermediate 4-1.
Preparation and evaluation of organic electroluminescent device
Example 1
Under vacuum of 1X 10 -5 Pa was deposited on a glass substrate containing Indium Tin Oxide (ITO) as an anode (film thickness: 100 nm) by vacuum evaporation.
The compound HAT-CN was vapor-deposited on the substrate to form a Hole Injection Layer (HIL) having a film thickness of 60 nm.
A Hole Transport Layer (HTL) having a thickness of 20nm was formed on the Hole Injection Layer (HIL) by vapor deposition of NPB compound.
The compound 1 and the compound 2 were co-deposited on the Hole Transport Layer (HTL) to form an emission layer (EML) having a thickness of 35 nm. The concentration of compound 2 in the light-emitting layer (EML) was 97%, and the concentration of compound B was 3%.
The compound A-2 and LiQ were co-evaporated on the light-emitting layer (EML) to vaporize the two materials at the same rate, thereby forming an Electron Transport Layer (ETL) having a thickness of 35 nm.
LiF was deposited on the Electron Transport Layer (ETL) by evaporation to form an Electron Injection Layer (EIL) having a thickness of 1 nm.
Metal Al was evaporated on the Electron Injection Layer (EIL) to form a metal cathode having a thickness of 80 nm.
Examples 2 to 3
An organic electroluminescent device was produced in the same manner as in example 1, using the compounds in Table 1 in place of Compound A-2.
Comparative example 1
An organic electroluminescent device was produced in the same manner as in example 1, except that the compound ET-01 was used instead of the compound a-2.
For the organic electroluminescent device prepared as above, 700cd/m 2 The driving voltage, the luminous efficiency, the color coordinate and the service life were measured and evaluated under the luminance of light emitted.
TABLE 1
As can be seen from table 1, the organic compound provided by the present disclosure, in the organic electroluminescent device as an electron transport layer, can effectively reduce the driving voltage, improve the luminous efficiency and prolong the lifetime, compared to the comparative example.
Simulation comparisons of the electron cloud distribution and the lowest unoccupied orbital (LUMO) of ET01, compound A-2, compound B-1, and Compound D-5 were performed at the level of B3LYP/6-31G using quantum chemical simulation software, and the results are shown in Table 2.
TABLE 2
As can be seen from the HOMO/LUMO distribution of the compounds in table 2, the presence of carborane does not change the electron cloud distribution characteristics of the material itself, and the larger volume thereof is beneficial to improving the crystallinity of the material; and the carborane has a certain degree of electron-withdrawing property, so that electrons have higher mobility and the device has higher luminous efficiency.
Claims (4)
1. An organic compound, wherein the structure of the organic compound is represented by formula 1:
wherein, Y 1 、Y 2 、Y 3 Each independently selected from N;
L 1 selected from single bonds;
Ar 1 、Ar 2 selected from single bonds;
R 1 、R 2 each independently selected from hydrogen or a group consisting of:
R 3 、R 4 each independently selected from the group consisting of:
R 5 each independently selected from the group consisting of:
2. An organic compound selected from the group consisting of:
wherein the content of the first and second substances,
the unmarked vertex in (1) is BH.
3. An organic electroluminescent device is characterized by comprising an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode; wherein the functional layer comprises the organic compound of any one of claims 1-2.
4. The organic electroluminescent device according to claim 3, wherein the functional layer comprises an electron transport layer or a hole blocking layer, and the organic compound is contained in the electron transport layer or the hole blocking layer.
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