CN112812051A - Organic luminescent material containing spirofluorene as center - Google Patents
Organic luminescent material containing spirofluorene as center Download PDFInfo
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- CN112812051A CN112812051A CN201911115761.0A CN201911115761A CN112812051A CN 112812051 A CN112812051 A CN 112812051A CN 201911115761 A CN201911115761 A CN 201911115761A CN 112812051 A CN112812051 A CN 112812051A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
- H10K50/121—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants for assisting energy transfer, e.g. sensitization
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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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
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C09K2211/1011—Condensed systems
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- C—CHEMISTRY; METALLURGY
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- Engineering & Computer Science (AREA)
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- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention develops an organic luminescent material with spirofluorene as a center. The spirofluorene molecule has simple structure and is convenient for chemical modification and functionalization. The invention constructs a material with high solid-state luminous efficiency by using spirofluorene. The spirofluorene is connected with a group with both hole transmission capability and electron transmission capability, so that the luminescent material with high solid-state luminous efficiency and double-stage transmission characteristic can be obtained. In particular to a preparation method of the organic luminescent material containing spirofluorene. In addition, the application of the organic luminescent material containing spirofluorene in an organic electroluminescent device is provided. An organic luminescent material containing spirofluorene has a structural formula shown in formula (1):
Description
Technical Field
The invention relates to the field of organic electroluminescent materials, in particular to a synthesis method of a spirofluorene derivative and application of the spirofluorene derivative as an electrophosphorescent main material in the field of organic electroluminescence.
Technical Field
The application of the organic electroluminescent (OLED) material in the fields of information display materials, organic optoelectronic materials and the like has great research value and good application prospect. With the development of multimedia information technology, the requirements for the performance of flat panel display devices are higher and higher. The main display technologies at present are plasma display devices, field emission display devices, and organic electroluminescent display devices (OLEDs). The OLED has a series of advantages of self luminescence, low-voltage direct current driving, full curing, wide viewing angle, rich colors and the like, and compared with a liquid crystal display device, the OLED does not need a backlight source, has wider viewing angle and low power consumption, has the response speed 1000 times that of the liquid crystal display device, has wider application prospect and is a rapidly growing field in material science at present. The research and development of organic luminescent materials with better performance, high luminous efficiency and adjustable emission wavelength are the problems which are urgently needed to be solved by scientific researchers. However, the development of efficient luminescent materials is rather difficult because conventional materials in the aggregate state cause their luminescence to be quenched.
Disclosure of Invention
Aiming at the defects and shortcomings of the prior art, the invention mainly aims to provide an organic luminescent material containing spirofluorene as a center. The spirofluorene molecule has simple structure and is convenient for chemical modification and functionalization. The invention constructs a material with high solid-state luminous efficiency by using spirofluorene. The spirofluorene is connected with a group with both hole transmission capability and electron transmission capability, so that the luminescent material with high solid-state luminous efficiency and double-stage transmission characteristic can be obtained. The materials show excellent performance in the field of organic photoelectricity. In general, spirofluorene is a functional group with aggregation-induced emission characteristics, which has a simple structure and excellent performance, and has a wide application prospect in the construction of organic photoelectric materials.
Another object of the present invention is to provide a method for preparing the above organic light emitting material containing spirofluorene.
The invention also aims to provide application of the organic luminescent material containing spirofluorene in an organic electroluminescent device.
The purpose of the invention is realized by the following technical scheme:
an organic luminescent material containing spirofluorene has a structural formula shown in formula I:
the preparation method of the organic luminescent material containing spirofluorene comprises the following steps:
the organic luminescent material containing spirofluorene is applied to an organic electroluminescent device.
According to the invention, the spirofluorene is connected with the electron withdrawing group and the electron donating group, so that the carrier transmission performance of the spirofluorene derivative is well adjusted. The obtained structure is distorted, and strong pi-pi interaction is not easy to generate in an aggregation state; in addition, the twisted molecular structure is beneficial to improving the triplet state energy level of the material, so that the obtained material can be used as a luminescent host material with different light colors. The characterization data of the organic electroluminescent device can show that the organic luminescent material containing spirofluorene can be used as a luminescent layer and also can be used as a phosphorescent main material, so that the electroluminescent device with good photoelectric performance, simple structure and low cost is prepared, has wide application prospect in the field of organic electroluminescence, and is expected to be widely applied in the fields of panel display, solid-state lighting and the like.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) the organic luminescent main body material containing spirofluorene has the advantages of simple synthesis method, easily obtained raw materials, higher yield, stable structure of the obtained material and simple storage;
(2) the organic luminescent main body material containing spirofluorene has excellent electroluminescent performance and can be widely applied to the fields of organic electroluminescence and the like.
Drawings
In the attached drawings of the specification, FIG. 1 is a schematic view of a device structure, and the device structure is MoO3(1)/NPB(2)/TCTA (3)/-:Firpic(4)/TmPyPb(5)/CsCO3(6)/Al(7)。
Table 1 shows the device data of I, the device structure is MoO3(5nm)/NPB(60nm)/TCTA(5 nm)/-:Firpic(13％,10nm)/TmPyPb(35nm)/CsCO3(2nm)/Al(100nm)。
Detailed Description
For better understanding of the present invention, the technical solution of the present invention will be specifically described below by way of specific examples.
Example 1: the organic electroluminescent material containing spirofluorene of the present example has the formula (1): preparation of 4 CzODF.
4-fluorobenzophenone boric acid (24.5g,100mmol), carbazole (16.7g,100mmol), potassium carbonate (2.8g), DMSO 80ml, heating and refluxing at 150 ℃ for 12H to obtain the products of 4-carbazole benzophenone boric acid (35g), tetrabromo spirofluorene (14g,20mmol), THF 200ml,75 ℃, H2O(10mL)，Pd(PPh3)4(4.6g, 4mmol)，K2CO3(0.27g,2mmol) is refluxed for 12 hours, cooled to room temperature, poured into 200ml to precipitate a large amount of solid, stirred for 0.5 hour, filtered to obtain white solid, and purified by column chromatography to obtain 1.2g of white solid with yield of 84 percent.
Elemental analysis: theoretical value (C125H76N4O 4): c, 88.42; h, 4.51; n, 3.30; o, 3.77; measured value: c, 88.39; h, 4.57; n, 3.31; o,3.73, HRMS (ESI) M/z (M +): theoretical value: 1696.58, respectively; measured value: 1696.62.
example 2:
this example tests the blue OLEDs device performance of organic electroluminescent materials containing spirofluorene (4 CzODF): blue-light-doped devices (a-C) were prepared using the organic electroluminescent material containing spirofluorene prepared in example 1 as the host, and the device performance was characterized by the test results shown in table 1.
The device structure is as follows: ITO (150nm)/MoO3(5nm)/NPB (60nm)/TCTA (5nm)/4CzODF Firpic (13% -15%, 10nm)/TmPyPb (35nm)/CsCO3(2nm)/Al(100nm)。
Table 1 performance parameters of devices a-C.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (5)
1. A spirofluorene compound has the following chemical structural formula:
2. an organic electroluminescent device, characterized in that at least one functional layer of the organic electroluminescent device contains the spirofluorene compound according to claim 1.
3. The organic electroluminescent device according to claim 2, wherein the functional layer is a light-emitting layer.
4. The organic electroluminescent device according to claim 3, wherein the light-emitting layer material comprises a host material and a guest light-emitting dye, and the host light-emitting material is the spirofluorene compound of claim 1.
5. The host luminescent material according to claim 4, wherein the dopant proportion in the luminescent layer is 1 to 99 wt%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911115761.0A CN112812051A (en) | 2019-11-15 | 2019-11-15 | Organic luminescent material containing spirofluorene as center |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911115761.0A CN112812051A (en) | 2019-11-15 | 2019-11-15 | Organic luminescent material containing spirofluorene as center |
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| Publication Number | Publication Date |
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| CN112812051A true CN112812051A (en) | 2021-05-18 |
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| CN201911115761.0A Pending CN112812051A (en) | 2019-11-15 | 2019-11-15 | Organic luminescent material containing spirofluorene as center |
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2019
- 2019-11-15 CN CN201911115761.0A patent/CN112812051A/en active Pending
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