CN112724158B - Compound for organic luminescence and application thereof - Google Patents

Compound for organic luminescence and application thereof Download PDF

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CN112724158B
CN112724158B CN202011530406.2A CN202011530406A CN112724158B CN 112724158 B CN112724158 B CN 112724158B CN 202011530406 A CN202011530406 A CN 202011530406A CN 112724158 B CN112724158 B CN 112724158B
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俞云海
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EverDisplay Optronics Shanghai Co Ltd
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Abstract

The invention relates to a compound for organic luminescence, which has a structure shown in a formula (I):
Figure DDA0002851884450000011
wherein X is selected from an oxygen atom, a sulfur atom or a selenium atom; l is1Selected from directly bonded, substituted or unsubstituted (hetero) arylene; r1Selected from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted silane, substituted or unsubstituted amine, substituted or unsubstituted alkylamino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted heteroaryl, and substituted or unsubstituted heteroarylamine. The invention provides a aza-condensed ring compound as a phosphorescent main body material, which has higher quantum yield, and simultaneously the planar structure of the material enables the material to have higher carrier mobility, and the more rigid structure enables the material to have good heat-resistant stability.

Description

Compound for organic luminescence and application thereof
Technical Field
The invention relates to the field of photoelectric materials, in particular to a compound for organic luminescence and application thereof.
Background
In general, the design principle of phosphorescent host materials includes the following points: 1) has a higher triplet energy level than the guest dopant; 2) the energy levels of HOMO and LUMO need to be well matched with the energy levels of adjacent active layers, so that the injection energy barrier of holes and electrons is reduced; 3) the carrier mobility is good, and the recombination probability of holes and electrons is further improved; 4) good thermal stability and film forming property.
Based on these principles, a series of hole-transporting phosphorescent materials have been developed, such as carbazole compounds, triphenylamine compounds, and other materials; meanwhile, some electron-transporting phosphorescent materials have attracted attention, such as oxadiazole compounds, diphenylphosphine oxide derivatives, triazines, pyridine/pyrimidines, phenanthroimidazole compounds, and the like. If the two materials are combined, a bipolar phosphorescent host material having both hole transporting performance and electron transporting performance and matching hole and electron mobilities can be developed.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provides a compound for organic light emitting and application thereof.
In order to achieve the purpose, the invention adopts the technical scheme that:
the first aspect of the present invention provides a compound for organic light emission, the compound having a structure represented by formula (I):
Figure BDA0002851884440000011
wherein X is selected from an oxygen atom, a sulfur atom or a selenium atom; l is1Selected from directly bonded, substituted or unsubstituted (hetero) arylene; r1Selected from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted silane, substituted or unsubstituted amine, substituted or unsubstituted alkylamino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted heteroaryl, and substituted or unsubstituted heteroarylamine.
Preferably, L1Selected from direct bonding or phenylene.
Preferably, R1The structure of (II) is shown as the formula:
Figure BDA0002851884440000021
preferably, R2And R3Each independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkylUnsubstituted alkoxy, substituted or unsubstituted silane groups, substituted or unsubstituted amine groups, substituted or unsubstituted alkylamino groups, substituted or unsubstituted aryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted arylamine groups, substituted or unsubstituted heteroaryl groups, and substituted or unsubstituted heteroarylamine groups.
Preferably, R1The structure of (A) is shown as formula (III):
Figure BDA0002851884440000022
preferably, R4Selected from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted silane, substituted or unsubstituted amine, substituted or unsubstituted alkylamino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted heteroaryl, and substituted or unsubstituted heteroarylamine.
Preferably, the compound is selected from:
Figure BDA0002851884440000031
a second aspect of the present invention provides an organic light-emitting material comprising a compound as described above.
A third aspect of the invention provides a light-emitting layer comprising an organic light-emitting material as described above.
A fourth aspect of the invention provides an OLED device comprising a light-emitting layer as described above.
By adopting the technical scheme, compared with the prior art, the invention has the following technical effects:
the invention provides a aza-condensed ring compound as a phosphorescent main body material, which has higher quantum yield, and simultaneously the planar structure of the material enables the material to have higher carrier mobility, and the more rigid structure enables the material to have good heat-resistant stability.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be obtained by a person skilled in the art without any inventive step based on the embodiments of the present invention, are within the scope of the present invention.
It should be noted that the embodiments and features of the embodiments may be combined with each other without conflict.
The present invention is further illustrated by the following examples, which are not to be construed as limiting the invention.
Example 1
Figure BDA0002851884440000041
Tetratriphenylphosphine palladium (1.15g, 1mmol), tri-tert-butylphosphine (0.20g, 1mmol), potassium carbonate (13.82g, 100mmol) and 100mL degassed toluene were added to a nitrogen-protected reaction flask, then A1(30.66g, 70mmol) and B1(19.39g, 70mmol) were added and the mixture was refluxed for 24 hours. After the reaction is finished, the reaction mixture is cooled to room temperature, filtered, concentrated and dried, and then passes through a silica gel column to be recrystallized in isopropanol to obtain the compound 1.
The characterization results for compound 1 are as follows:
mass spectrum: 591.17 (molecular weight).
Nuclear magnetism: 1H NMR (400MHz, CDCl)3)：(3H，7.04)；(3H，7.05)；(1H，7.37)； (6H，7.50)；(1H，7.60)；(3H，7.80)；(4H，8.36)。
Example 2
Figure BDA0002851884440000042
Tetratriphenylphosphine palladium (1.15g, 1mmol), tri-tert-butylphosphine (0.20g, 1mmol), potassium carbonate (13.82g, 100mmol) and 100mL degassed toluene were added to a nitrogen-protected reaction flask, then A2(32.90g, 70mmol) and B2(19.39g, 70mmol) were added and the mixture was refluxed for 24 hours. After the reaction is finished, the reaction mixture is cooled to room temperature, filtered, concentrated and dried, and then passes through a silica gel column to be recrystallized in isopropanol to obtain the compound 2.
The characterization results for compound 2 are as follows:
mass spectrum: 623.12 (molecular weight).
Nuclear magnetism: 1H NMR (400MHz, CDCl)3)：(3H，7.16)；(3H，7.26)；(3H，7.33)； (1H，7.35)；(6H，7.50)；(1H，7.67)；(4H，8.36)。
Example 3
Figure BDA0002851884440000051
Tetratriphenylphosphine palladium (1.15g, 1mmol), tri-tert-butylphosphine (0.20g, 1mmol), potassium carbonate (13.82g, 100mmol) and 100mL degassed toluene were added to a nitrogen-protected reaction flask, then A3(39.61g, 70mmol) and B3(19.39g, 70mmol) were added and the mixture was refluxed for 24 hours. After the reaction is finished, the reaction mixture is cooled to room temperature, filtered, concentrated and dried, and then passes through a silica gel column to be recrystallized in isopropanol to obtain the compound 3.
The characterization of compound 3 is as follows:
mass spectrum: 719.01 (molecular weight).
Nuclear magnetism: 1H NMR (400MHz, CDCl)3)：(3H，7.19)；(3H，7.37)；(6H，7.50)； (1H，7.71)；(1H，7.95)；(3H，8.08)；(4H，8.36)。
Example 4
Figure BDA0002851884440000052
Tetratriphenylphosphine palladium (1.15g, 1mmol), tri-tert-butylphosphine (0.20g, 1mmol), potassium carbonate (13.82g, 100mmol) and 100mL degassed toluene were added to a nitrogen-protected reaction flask, then A4(30.66g, 70mmol) and B4(24.72g, 70mmol) were added and the mixture was refluxed for 24 hours. After the reaction is finished, the reaction mixture is cooled to room temperature, filtered, concentrated and dried, and then passes through a silica gel column to be recrystallized in isopropanol to obtain the compound 4.
The characterization of compound 4 is as follows:
mass spectrum: 667.20 (molecular weight).
Nuclear magnetism: 1H NMR (400MHz, CDCl)3)：(3H，7.04)；(3H，7.05)；(2H，7.25) (1H，7.37)；(6H，7.50)；(1H，7.60)；(3H，7.80)；(2H，7.96)；(4H，8.36)。
Example 5
Figure BDA0002851884440000061
Tetratriphenylphosphine palladium (1.15g, 1mmol), tri-tert-butylphosphine (0.20g, 1mmol), potassium carbonate (13.82g, 100mmol) and 100mL degassed toluene were added to a nitrogen-protected reaction flask, then A5(30.66g, 70mmol) and B5(19.39g, 70mmol) were added and the mixture was refluxed for 24 hours. After the reaction is finished, the reaction mixture is cooled to room temperature, filtered, concentrated and dried, and then passes through a silica gel column to be recrystallized in isopropanol to obtain the compound 5.
The characterization of compound 5 is as follows:
mass spectrum: 591.17 (molecular weight).
Nuclear magnetism: 1H NMR (400MHz, CDCl)3)：(3H，7.04)；(3H，7.05)；(6H，7.50)； (1H，7.57)；(1H，7.62)；(3H，7.80)；(4H，8.36)。
Example 6
Figure BDA0002851884440000062
Tetratriphenylphosphine palladium (1.15g, 1mmol), tri-tert-butylphosphine (0.20g, 1mmol), potassium carbonate (13.82g, 100mmol) and 100mL degassed toluene were added to a nitrogen-protected reaction flask, then A6(30.66g, 70mmol) and B6(17.51g, 70mmol) were added and the mixture was refluxed for 24 hours. After the reaction is finished, the reaction mixture is cooled to room temperature, filtered, concentrated and dried, and then passes through a silica gel column to be recrystallized in isopropanol to obtain the compound 6.
The characterization of compound 6 is as follows:
mass spectrum: 564.16 (molecular weight).
Nuclear magnetism: 1H NMR (400MHz, CDCl)3)：(3H，7.04)；(3H，7.05)；(2H，7.32)； (1H，7.59)；(2H，7.67)；(5H，7.80)；(1H，7.93)；(2H，8.03)；(1H，8.16)。
Example 7
Figure BDA0002851884440000071
Tetratriphenylphosphine palladium (1.15g, 1mmol), tri-tert-butylphosphine (0.20g, 1mmol), potassium carbonate (13.82g, 100mmol) and 100mL degassed toluene were added to a nitrogen-protected reaction flask, then A7(30.66g, 70mmol) and B7(17.99g, 70mmol) were added and the mixture was refluxed for 24 hours. After the reaction is finished, the reaction mixture is cooled to room temperature, filtered, concentrated and dried, and then passes through a silica gel column to be recrystallized in isopropanol to obtain the compound 7.
The characterization of compound 7 resulted in the following:
mass spectrum: 571.20 (molecular weight).
Nuclear magnetism: 1H NMR (400MHz, CDCl 3): (9H, 1.35); (3H, 7.04); (3H, 7.05); (3H, 7.50); (1H, 7.57); (1H, 7.62); (3H, 7.80); (2H, 8.36).
Example 8
Figure BDA0002851884440000072
Tetratriphenylphosphine palladium (1.15g, 1mmol), tri-tert-butylphosphine (0.20g, 1mmol), potassium carbonate (13.82g, 100mmol) and 100mL degassed toluene were added to a nitrogen-protected reaction flask, then A8(30.66g, 70mmol) and B8(25.70g, 70mmol) were added and the mixture was refluxed for 24 hours. After the reaction is finished, the reaction mixture is cooled to room temperature, filtered, concentrated and dried, and then passes through a silica gel column to be recrystallized in isopropanol to obtain the compound 8.
The characterization of compound 8 is as follows:
mass spectrum: 682.19 (molecular weight).
Nuclear magnetism: 1H NMR (400MHz, CDCl)3)：(3H，7.04)；(3H，7.05)；(1H，7.22)； (2H，7.48)；(4H，7.50)；(2H，7.52)；(1H，7.57)；(1H，7.62)；(3H，7.80)； (1H，8.14)；(2H，8.36)。
Application examples
An OLED device is prepared by the following steps:
ultrasonically cleaning a transparent anode electrode ITO substrate in isopropanol for 10min, exposing the transparent anode electrode ITO substrate to ultraviolet light for 30min, and then treating the transparent anode electrode ITO substrate with plasma for 10 min; then putting the processed ITO substrate into evaporation equipment; first, a layer of NPB and F4TCNQ of 50nm was mixed and evaporated, then NPB of 150nm was evaporated on the mixed layer, and then a mixture of an evaporated compound and 2% (piq) was mixed and evaporated2Iracac, film thickness 40nm, followed by evaporation of 30nm Alq3Then, 2nm LiF is evaporated, and finally 150nm metal Al is evaporated to form a metal cathode, so that the organic light-emitting element is manufactured.
That is, the structure of the organic light emitting element prepared in this application example is:
ITO/NPB F4 TCNQ/NPB/synthetic Compound (piq)2Iracac/Alq3/LiF/Al。
The specific structural formulas corresponding to the abbreviations of the above materials are as follows:
Figure BDA0002851884440000081
comparative example
The difference from the above application embodiment is that: and (piq)2The compound mixed and evaporated by Iracac is CBP:
Figure BDA0002851884440000091
that is, the structure of the organic light-emitting element prepared in this comparative example was:
ITO/NPB:F4TCNQ/NPB/CBP:(piq)2Iracac/Alq3/LiF/Al。
detection examples
The above application examples and comparative examples were subjected to performance tests, and the results were as follows:
TABLE 1
Serial number Phosphorescent host materials Current efficiency (Cd/A) Driving voltage (V)
Application example 1 Compound 1 17 3.9
Application example 2 Compound 2 16 4.1
Application example 3 Compound 3 18 4.1
Application example 4 Compound 4 17 4.2
Application example 5 Compound 5 19 4.0
Application example 6 Compound 6 15 3.8
Application example 7 Compound 7 16 3.9
Application example 8 Compound 8 22 3.7
Comparative example 1 CBP 8 4.3
Wherein, the ratio of the brightness to the current density at 1000nits is the current efficiency; when the brightness of the OLED device is maintained at 1000nits, the measured potential difference of the light emitting layer is the driving voltage.
In conclusion, the invention provides a aza-condensed ring compound as a phosphorescent main body material, which has higher quantum yield, and simultaneously the planar structure of the material enables the material to have higher carrier mobility, and the rigid structure enables the material to have good heat-resistant stability.
While the invention has been described with reference to a preferred embodiment, it will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the spirit and scope of the invention.

Claims (4)

1. A compound for use in organic light emission, wherein the compound is selected from the group consisting of:
Figure FDA0003496679940000011
2. an organic light-emitting material comprising the compound according to claim 1.
3. A light-emitting layer comprising the organic light-emitting material according to claim 2.
4. An OLED device comprising the light-emitting layer of claim 3.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111423390A (en) * 2020-03-30 2020-07-17 北京燕化集联光电技术有限公司 Novel structural compound and application thereof
CN111689985A (en) * 2020-07-10 2020-09-22 北京燕化集联光电技术有限公司 Containing SO2Compound with multi-heterocyclic structure and application thereof
CN112079867A (en) * 2020-09-27 2020-12-15 北京燕化集联光电技术有限公司 P-containing multi-heterocyclic structure compound and application thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111423390A (en) * 2020-03-30 2020-07-17 北京燕化集联光电技术有限公司 Novel structural compound and application thereof
CN111689985A (en) * 2020-07-10 2020-09-22 北京燕化集联光电技术有限公司 Containing SO2Compound with multi-heterocyclic structure and application thereof
CN112079867A (en) * 2020-09-27 2020-12-15 北京燕化集联光电技术有限公司 P-containing multi-heterocyclic structure compound and application thereof

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Condensed Phenoxazine Dimer and Its Radical Cation;Takayuki Miyamae et al.;《Org. Lett.》;20200819;第 6790-6793页 *
Synthesis and Properties of Hydrazine-Embedded Biphenothiazinesand Application of Hydrazine-Embedded Heterocyclic Compoundsto Fluorescence Cell Imaging;Yuri Shindo et al.;《Asian J. Org. Chem.》;20180810;第1-6页 *
Synthesis of Three-Dimensional Butterfly Slit- Cyclobisazaanthracenes and Hydrazinobisanthenes through One- Step Cyclodimerization and Their Properties;Koji Yamamoto et al.;《Chem. Eur. J.》;20151130;第663-671页 *

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