CN110746325A - N-type doped compound based on guanidine framework and application thereof - Google Patents
N-type doped compound based on guanidine framework and application thereof Download PDFInfo
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- CN110746325A CN110746325A CN201810817932.3A CN201810817932A CN110746325A CN 110746325 A CN110746325 A CN 110746325A CN 201810817932 A CN201810817932 A CN 201810817932A CN 110746325 A CN110746325 A CN 110746325A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/16—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of rings other than six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/18—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
- H10K50/165—Electron transporting layers comprising dopants
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
Abstract
An n-type doped compound based on a guanidine skeleton and application thereof. The invention provides an n-type dopant based on a guanidine framework and application thereof, which ensure that the dopant not only has high-efficiency conductivity, but also has good thermal stability when being used as a dopant of an electron transport layer through reasonable molecular structure design.
Description
Technical Field
The invention belongs to the field of photoelectric materials, and relates to an n-type doped compound based on a guanidine framework and application thereof.
Background
With the development of organic electroluminescent devices, how to improve the efficiency of the devices becomes a goal pursued by researchers, and the key point for realizing the efficiency improvement is to increase the carrier mobility and the carrier density of the organic electron transport layer.
To increase the conductivity, the solution can be made by two methods. Firstly, an intermediate dielectric layer is added between the cathode layer and the electron transport layer to improve the carrier injection efficiency. Secondly, doping the organic host material with suitable electron donating groups can increase the density of charge carriers, in which case the organic host material needs to be co-sublimed for deposition with a guest material.
For the former method, LiF, CsF and CsCO3Often used, the addition of these substances can effectively reduce the work function of electrons, and an intermediate layer composed of these substances can significantly promote electron transport, but this method does not appear significantly to the realization of high-efficiency devices.
For the dopant of the electron transport layer, it is required that the HOMO level of the dopant is above the LUMO level of the host material, which is a prerequisite for electron transfer from the dopant to the host material, so that the conductivity can be increased. In addition, the valence electrons of the dopant preferably have a very low work function or ion energy, which may enhance the electron release of the dopant, thereby promoting the conductivity of the layer. The n-type dopant itself is a very strong donor and reacts very easily with oxygen in the air.
Disclosure of Invention
In order to solve the technical problems, the invention provides an n-type dopant based on a guanidine skeleton and application thereof, and through reasonable molecular structure design, the n-type dopant is ensured to have high-efficiency conductivity and good thermal stability when used as a dopant of an electron transport layer.
In order to achieve the technical effect, the invention adopts the following technical scheme:
one of the purposes of the invention is to provide an n-type doped compound based on a guanidine framework, which is characterized in that the structure of the compound is shown as a formula I or a formula II:
wherein R is11～R15And R22～R29Any one of the groups is independently any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group or a substituted or unsubstituted dialkylamine, R21To satisfy the requirements of its chemical environmentMeaning a group.
As a preferred embodiment of the present invention, R is21May be a substituted or unsubstituted straight or branched alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, a substituted or unsubstituted,
Any one of them.
Preferably, the R or R' are each independently any one of-O-, a substituted or unsubstituted imino group, a substituted or unsubstituted straight or branched alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
In the present invention, the substituted or unsubstituted linear alkylene group is preferably a linear alkylene group having from C1 to C12 (for example, C2, C3, C4, C5, C6, C7, C8, C9, C10, or C11).
The substituted or unsubstituted branched alkylene group is preferably a branched alkylene group having from C1 to C12 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, or C11).
The substituted or unsubstituted cycloalkylene group is preferably a substituted or unsubstituted cycloalkylene group of C3 to C12 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, or C11).
The substituted or unsubstituted arylene group is preferably an arylene group having from C6 to C13 (e.g., C7, C8, C9, C10, C11, or C12).
The substituted or unsubstituted heteroarylene is preferably a C5-C13 (e.g., C6, C7, C8, C9, C10, C11, or C12) substituted or unsubstituted heteroarylene.
As a preferred embodiment of the present invention, R is11～R15And R22～R29Any one of the groups is any one of hydrogen atom, deuterium atom, alkyl of C1-C12, alkoxy of C1-C6, cycloalkyl of C3-C12, aryl of C6-C15, 5-or 6-membered heteroaryl of C5-C15, aryloxy of C6-C15 or dialkylamine of C2-C12.
In a preferred embodiment of the present invention, the alkyl group having 1 to 12 includes any one of a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, an n-hexyl group, a 3-hexyl group, an n-heptyl group, a 2-heptyl group, an n-octyl group, a 2-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, and an n-dodecyl group.
Preferably, the C1-C6 alkoxy group includes any one of methoxy, ethoxy, n-propoxy, isopropoxy or tert-butoxy.
In a preferred embodiment of the present invention, the cycloalkyl group having 3 to 12 includes any one of cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl groups, which are optionally substituted with a substituent having 1 to 9.
In a preferred embodiment of the present invention, the aryl group having C6 to C15 includes any one of a phenyl group, a phenyl group substituted with at least one substituent having C1 to C9, a naphthyl group, and a naphthyl group substituted with at least one substituent having C1 to C5.
Preferably, the aryloxy group of C6-C15 is the aryl group of C6-C15 connected to the compound body through an oxygen atom.
In a preferred embodiment of the present invention, the 5-or 6-membered heteroaryl group having C5 to C15 is substituted or unsubstituted with a substituent having C1 to C9, and the 5-or 6-membered heteroaryl group is any one of pyrazolyl, furyl, thiazolyl, oxazolyl, isoxazolyl, imidazolyl, triazolyl, thienyl, thiadiazolyl, pyridyl, pyrimidinyl, pyrazinyl, and pyridazinyl.
In a preferred embodiment of the present invention, the dialkylamine having at least one carbon atom selected from the group consisting of 2 to 12 is an amino group substituted with two alkyl groups having at least one carbon atom selected from the group consisting of 1 to 11, wherein the alkyl group having at least one carbon atom selected from the group consisting of 1 to 11 comprises a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a n-pentyl group, an isopentyl group, a n-hexyl group, a 3-hexyl group, a n-heptyl group, a 2-heptyl group, a n-octyl group, a.
In a preferred embodiment of the present invention, the substituent of C1 to C9 includes any one of an alkyl group of C1 to C9, a cycloalkyl group of C3 to C9, an alkenyl group of C2 to C9, or an alkynyl group of C2 to C9.
The meanings of the C1-C9 alkyl group and the C3-C9 cycloalkyl group are similar to those of the C1-C12 alkyl group and the C3-C12 cycloalkyl group, and are different only in the number of carbon atoms, and thus the description thereof is omitted. The alkenyl group of C2 to C9 may be understood as any one of a vinyl group substituted or unsubstituted with at least one alkyl group of C1 to C7. The alkynyl group having C2 to C9 is understood to be any of ethynyl groups which are substituted or unsubstituted with an alkyl group having C1 to C7.
The n-type doped compound based on the guanidine framework provided by the invention is preferably as follows:
The other purpose of the invention is to provide an organic electroluminescent device, wherein an electron transport layer of the organic electroluminescent device is doped with the n-type doped compound based on the guanidine framework.
Compared with the prior art, the invention has at least the following beneficial effects:
the invention provides an n-type dopant based on a guanidine skeleton and application thereof, and through reasonable molecular structure design, the n-type dopant is ensured to have high-efficiency conductivity and good thermal stability when used as a dopant of an electron transport layer.
Detailed Description
For the purpose of facilitating an understanding of the present invention, the present invention will now be described by way of examples. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
The invention provides a synthesis method of compounds shown in formula I and formula II, which comprises the following steps:
the synthesis method of the monoguanidine comprises the following steps:
the method for synthesizing the biguanide comprises the following steps:
wherein the synthetic method of the biguanide takes R21 as
For example.
Example 1
The invention provides an n-type doped compound based on a guanidine framework, which has a structure shown in a formula III:
the synthesis method of the compound shown in the formula III comprises the following steps:
1mol
reacting under DIAP catalysis to obtain intermediate
And then with 1.2mol
And reacting to obtain the compound shown in the formula III.
Process for preparing compounds of formula III1H NMR:(9H,1.00),(12H,1.44),(8H,1.66),(2H,2.00),(2H,2.57)。
Example 2
The invention provides an n-type doped compound based on a guanidine framework, which has a structure shown in a formula IV:
the synthesis method of the compound shown in the formula IV comprises the following steps:
1mol
reacting under DIAP catalysis to obtain intermediate
And then with 1.2mol
And reacting to obtain the compound shown in the formula IV.
Process for preparing compounds of formula IV1H NMR:(12H,1.44),(8H,1.66),(2H,2.00),(9H,2.35),(2H,2.57),(2H,6.70)。
Example 3
The invention provides an n-type doped compound based on a guanidine framework, which has a structure shown in a formula V:
the synthesis method of the compound shown in the formula V comprises the following steps:
1.2mol
with 1mol of
And carrying out reflux reaction in methanol by using sodium methoxide as a catalyst for 24h to obtain the compound shown in the formula V.
Process for preparing compounds of formula V1H NMR:(18H,1.00),(24H,1.44),(16H,1.66),(2H,2.00),(4H,2.57)。
Example 4
The invention provides an n-type doped compound based on a guanidine framework, which has a structure shown in a formula VI:
the preparation method of the compound shown in the formula VI comprises the following steps:
1.2mol
with 1mol of
And carrying out reflux reaction in methanol by using sodium methoxide as a catalyst for 24h to obtain the compound shown in the formula VI.
Process for preparing compounds of formula VI1H NMR:(24H,1.44),(16H,1.66),(4H,2.00),(18H,2.35),(4H,2.57),(4H,6.70)。
Example 5
The invention provides an n-type doped compound based on a guanidine framework, which has a structure shown in a formula VII:
1.2mol
with 1mol of
And carrying out reflux reaction in methanol by using sodium methoxide as a catalyst for 24h to obtain the compound shown in the formula VII.
Of compounds of formula VII1H NMR:(4H,7.46),(2H,7.12),(8H,7.03),(4H,6.82),(4H,6.65),(8H,6.52),(2H,4.12)。
Comparative application
The transparent anode electrode ITO substrate was ultrasonically cleaned in isopropanol for 10 minutes and exposed to uv light for 30 minutes, followed by plasma treatment for 10 minutes. And then putting the processed ITO substrate into evaporation equipment. First a 40nm layer of NPB was evaporated as a hole transport layer, followed by evaporation of the light emitting layer, hybrid evaporation, CBP, and 5% (piq)2Iracac, followed by evaporation of 30nm of Alq3 as an electron transport layer, followed by evaporation of 1nm LiF, followed by evaporation of 150nm of metallic Al.
Application examples
The transparent anode electrode ITO substrate was ultrasonically cleaned in isopropanol for 10 minutes and exposed to uv light for 30 minutes, followed by plasma treatment for 10 minutes. And then putting the processed ITO substrate into evaporation equipment. First a 40nm layer of NPB was evaporated as hole transport layer, followed by evaporation of the light emitting layer, mixed evaporation, CBP, and 5% (piq)2Iracac, followed by evaporation of 30nm of Alq 3/synthetic compound (60:40) (formula III, formula IV, formula V, formula VI, and formula VII) as electron transport layer, followed by evaporation of 1nm LiF, followed by evaporation of 150nm of metallic Al.
And (3) detecting the performance of the device:
the performance test results of the OLED devices at 1000nits are shown in table 1:
TABLE 1
| Device with a metal layer | Cd/A | Driver Voltage | CIEx | CIEy |
| Comparative application | 8 | 4.3 | 0.66 | 0.32 |
| Application example 1 | 9.1 | 4.1 | 0.66 | 0.32 |
| Application implementationExample 2 | 9.2 | 4.0 | 0.66 | 0.32 |
| Application example 3 | 10.0 | 4.0 | 0.66 | 0.32 |
| Application example 4 | 9.9 | 4.2 | 0.66 | 0.32 |
| Application example 5 | 9.5 | 4.0 | 0.66 | 0.32 |
As can be seen from the test results of table 1, the current efficiency of the organic electroluminescent device was significantly improved after the n-type dopant was added, and the driving voltage was also slightly decreased with substantially unchanged color coordinates.
The applicant states that the present invention is illustrated by the above examples to show the detailed process equipment and process flow of the present invention, but the present invention is not limited to the above detailed process equipment and process flow, i.e. it does not mean that the present invention must rely on the above detailed process equipment and process flow to be implemented. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (10)
1. An n-type doped compound based on a guanidine framework, wherein the structure of the compound is shown as formula I or formula II:
wherein R is11～R15And R22～R29Any one of the groups is independently any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group or a substituted or unsubstituted dialkylamine, R21Any group that satisfies its chemical environment.
2. A compound of claim 1, wherein R is21May be a substituted or unsubstituted straight or branched alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, a substituted or unsubstituted,
Any one of them.
Preferably, the R and R' are each independently any one of-O-, a substituted or unsubstituted imino group, a substituted or unsubstituted straight or branched alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
3. A compound according to claim 1 or 2, wherein R is11～R15And any one of R22-R29 is independently a hydrogen atom, a deuterium atom, an alkyl group having C1-C12, an alkoxy group having C1-C6, a cycloalkyl group having C3-C12, an aryl group having C6-C15, or a 5-or 5-membered group having C5-C15Any one of 6-membered heteroaryl, C6-C15 aryloxy or C2-C12 dialkylamine.
4. The compound of claim 3, wherein the C1-C12 alkyl group comprises any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, 3-hexyl, n-heptyl, 2-heptyl, n-octyl, 2-octyl, n-nonyl, n-decyl, n-undecyl, or n-dodecyl.
Preferably, the C1-C6 alkoxy group includes any one of methoxy, ethoxy, n-propoxy, isopropoxy or tert-butoxy.
5. The compound of claim 3, wherein the C3-C12 cycloalkyl group comprises any one of cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by C1-C9 substituents.
6. The compound of claim 3, wherein the aryl group of C6-C15 comprises any one of a phenyl group, a phenyl group substituted with at least one substituent of C1-C9, a naphthyl group, or a naphthyl group substituted with at least one substituent of C1-C5;
preferably, the aryloxy group of C6-C15 is the aryl group of C6-C15 connected to the compound body through an oxygen atom.
7. The compound of claim 3, wherein the 5-or 6-membered heteroaryl group having C5-C15 is substituted or unsubstituted with a C1-C9 substituent, and is any one of pyrazolyl, furyl, thiazolyl, oxazolyl, isoxazolyl, imidazolyl, triazolyl, thienyl, thiadiazolyl, pyridyl, pyrimidinyl, pyrazinyl or pyridazinyl.
8. A compound according to claim 3, wherein the C2-C12 dialkylamine is an amino group substituted with two C1-C11 alkyl groups, and wherein the C1-C11 alkyl groups comprise any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, 3-hexyl, n-heptyl, 2-heptyl, n-octyl, 2-octyl, n-nonyl, n-decyl, or n-undecyl.
9. The compound of any one of claims 5 to 8, wherein the substituent of C1 to C9 comprises any one of an alkyl group of C1 to C9, a cycloalkyl group of C3 to C9, an alkenyl group of C2 to C9, or an alkynyl group of C2 to C9.
10. An organic electroluminescent device, characterized in that the electron transport layer of the organic electroluminescent device is doped with a compound according to any one of claims 1 to 9.
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