CN111217740A - Bipolar organic photoelectric material based on N-C = O resonance structure and preparation method and application thereof - Google Patents

Bipolar organic photoelectric material based on N-C = O resonance structure and preparation method and application thereof Download PDF

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CN111217740A
CN111217740A CN202010119982.1A CN202010119982A CN111217740A CN 111217740 A CN111217740 A CN 111217740A CN 202010119982 A CN202010119982 A CN 202010119982A CN 111217740 A CN111217740 A CN 111217740A
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organic photoelectric
photoelectric material
resonance structure
bipolar organic
bipolar
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陈润锋
姜贺
靳继彪
黄维
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Nanjing University of Posts and Telecommunications
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    • C07D209/80—[b, c]- or [b, d]-condensed
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    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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    • C07D209/80—[b, c]- or [b, d]-condensed
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Abstract

The invention discloses a bipolar organic photoelectric material based on an N-C ═ O resonance structure, a preparation method and application thereof.
Figure DDA0002392662060000011

Description

Bipolar organic photoelectric material based on N-C ═ O resonance structure, preparation method and application
Technical Field
The invention relates to a bipolar organic photoelectric material, a preparation method and application thereof, in particular to a bipolar organic photoelectric material based on an N-C ═ O resonance structure, a preparation method and application thereof.
Background
The organic photoelectric material is an organic material with photoelectric activity, has low preparation cost, small processing difficulty, easy industrial production and quick photoelectric response, and is widely applied to the fields of organic light-emitting diodes, organic solar cells, organic thin-film transistors, organic memories, sensors and the like. The organic photoelectric material with the bipolar transmission characteristic can simultaneously and efficiently transmit electrons and holes, and plays an important role in preparing high-performance organic photoelectric devices. At present, the types of bipolar organic photoelectric materials constructed are single, and most of the bipolar organic photoelectric materials are based on a Donor (Donor) -Acceptor (Acceptor) structure or a Donor-bridging unit (pi bridge) Acceptor structure, and a Donor unit for transmitting holes and an Acceptor unit for transmitting electrons are introduced into the same molecule at the same time, so that bipolar transmission of the holes and the electrons is realized. However, in such a Donor-Acceptor structure, there is generally a strong intramolecular interaction between the Donor and Acceptor units, and the conjugated system is extended, so that the band gap of the molecule is narrower, the luminescence is red-shifted, and the triplet level is reduced. Therefore, developing blue light host materials with wider band gap and higher triplet state energy level based on Donor-Acceptor structure design becomes a challenge of current research.
Disclosure of Invention
The purpose of the invention is as follows: the invention aims to provide a bipolar organic photoelectric material based on an N-C ═ O resonance structure.
The invention also aims to provide a preparation method of the bipolar organic photoelectric material based on the N-C ═ O resonance structure.
The last purpose of the invention is to provide the application of the bipolar organic photoelectric material based on the N-C ═ O resonance structure.
The technical scheme is as follows: the invention provides a bipolar organic photoelectric material based on an N-C ═ O resonance structure, which has a molecular structure general formula shown in the specification:
Figure BDA0002392662040000011
in the formula, R1And R2The same or different, each is a hydrogen atom, a bromine atom or a tert-butyl group.
The bipolar organic photoelectric material based on the N-C ═ O resonance structure is any one of the following materials:
Figure BDA0002392662040000021
the preparation method of the bipolar organic photoelectric material based on the N-C ═ O resonance structure comprises the steps of taking carbazole or bromocarbazole or tert-butylcarbazole and N, N-carbonyldiimidazole as raw materials, adding an organic solvent under the protection of inert gas, heating and stirring for 4-10 hours, cooling to room temperature after the reaction is finished, adding deionized water to separate out a white precipitate, carrying out suction filtration, collecting a white solid, dissolving, drying, filtering, concentrating a filtrate, and purifying by column chromatography.
The synthetic route is as follows:
Figure BDA0002392662040000022
further, the molar ratio of carbazole or bromocarbazole or tert-butylcarbazole to N, N-carbonyldiimidazole is 1-1.2: 1. the organic solvent is dimethyl sulfoxide. The reaction temperature is 100-120 ℃.
The bipolar organic photoelectric material based on the N-C ═ O resonance structure is applied to an organic electroluminescent device.
The material directly connects a carbazole unit with a hole transmission performance with an N-C-O resonance structure, and enables one carbazole to transmit holes and the other carbazole to transmit electrons in molecules through the dynamic self-adaptability of the N-C-O resonance structure, so that the transmission balance of the holes and the electrons is realized, and the acceptor-free bipolar organic photoelectric material is prepared. The organic electroluminescent devices of different types are prepared by utilizing the acceptor-free bipolar organic photoelectric material, and the prepared electroluminescent devices prove to be a material with application potential and provide a new molecular strategy for designing a novel bipolar organic photoelectric material.
Has the advantages that: the material synthesis steps are simple and easy to operate, the raw materials are easy to obtain, and the industrial requirements can be met. The bipolar organic photoelectric material has good solubility and thermal stability, high triplet state energy level and very balanced carrier transport capability, thereby being beneficial to the injection and the transport of holes and electrons. The material disclosed by the invention is applied to an organic electroluminescent device and can be used as a blue light main body material, and the blue light electroluminescent device prepared by using the bipolar organic photoelectric material based on the N-C ═ O resonance structure disclosed by the invention has excellent device performance.
Drawings
FIG. 1 is an ultraviolet absorption (UV) and fluorescence emission (PL) spectra of an organic photoelectric material 1 of the present invention in methylene chloride;
FIG. 2 shows a UV spectrum and a PL spectrum of the organic photoelectric material 1 of the present invention in a thin film state;
FIG. 3 is a thermogravimetric plot of the organic photovoltaic material 1 of the present invention;
FIG. 4 is a current density-voltage-luminance curve of a phosphorescent organic electroluminescent device (PhOLEDs) of the organic photoelectric material 1 of the present invention;
FIG. 5 is a graph of the efficiency of PhOLEDs of the organic photovoltaic material 1 according to the invention;
fig. 6 is a current density-voltage-luminance curve of a thermally activated delayed fluorescence type organic electroluminescent device (TADF OLED) of the organic photoelectric material 1 of the present invention;
fig. 7 is a graph of the efficiency of TADF OLEDs of the compounds of the present invention.
Detailed Description
Example 1: method for producing organic photoelectric material 1
Taking a two-mouth reaction bottle, adding 0.50g of carbazole and 0.24g of N, N-carbonyl diimidazole, vacuumizing, blowing argon gas for three times, adding 10mL of ultra-dry dimethyl sulfoxide under the protection of nitrogen gas to dissolve a substrate, heating and stirring at 100-120 ℃ for 6 hours, cooling to room temperature after the reaction is finished, adding deionized water to separate out a white precipitate, performing suction filtration, collecting a white solid, dissolving the white solid in dichloromethane, drying anhydrous sodium sulfate, filtering, concentrating the filtrate, and performing column chromatography purification to obtain a white solid. Yield: 44 percent.1HNMR(DMSO-d6,400MHz)δ(ppm):8.30(d,J＝8Hz,4H),7.44-7.37(m,8H),7.43(d,J＝8Hz,4H).13C NMR(CDCl3,100MHz)δ(ppm):149.53,137.95,127.24,125.91,123.57120.20,114.58.HRMS(EI):m/zcalcdforC25H16N2O[M]+:361.1347；found:361.1341.。
The structure is as follows:
Figure BDA0002392662040000031
example 2: performance characterization of phosphorescent organic electroluminescent devices (PhOLEDs)
The device using the complex as the light emitting layer in this embodiment may include: 1. a conductive glass layer (ITO); 2. PSS as a hole injection layer PEDOT; 3. a hole transport layer (TAPC); 4. exciton blocking layer (mCP); 5. a light emitting layer; 6. an electron transport layer (TmPyPB); 7. an electron injection Layer (LiF); 8. and a cathode Al.
The manufacturing method of PhOLEDs comprises the following steps: firstly, a PEDOT (PSS) hole injection layer is spin-coated on a cleaned glass substrate (ITO), and then evaporation is carried out in sequence. ITO/PEDOT PSS (30nm)/1,3,5-Triazo-2,4,6-triphosphorine-2,2,4,4,6, 6-Tetrachlororide (TAPC) (20nm)/N, N' -dicarbazolyl-3, 5-bezene (mCP) (8nm)/host:18 wt% FIrpic (22nm)/1,3,5-tri (m-pyridine-3-yl-phenyl) bezene (TmPyPB) (35nm)/LiF (1nm)/Al (100 nm). Wherein the host material in the light emitting layer is material 1 prepared in the above example. The current density-voltage-luminance curves of PhOLEDs are shown in figure 4. The efficiency curves of the PhOLEDs provided in this example are shown in figure 5.
Example 3: performance characterization of thermally activated delayed fluorescence organic electroluminescent devices (TADF OLEDs)
The device using the organic small molecule as the light emitting layer in this embodiment may include: 1. a conductive glass layer (ITO); 2. PSS as a hole injection layer PEDOT; 3. a light emitting layer; 4. an exciton blocking layer (TSPO 1); 5. an electron transport layer (TPBi); 6. an electron injection layer (Liq); 7. and a cathode Al.
The manufacturing method of the TADFOLES comprises the following steps: firstly, spin-coating a PEDOT (PSS) hole injection layer on cleaned ITO, and then sequentially evaporating. ITO/PEDOT PSS (30nm)/TAPC (20nm)/mCP (8nm)/host 30 wt% bis- [4- (9,9-dimethyl-9,10-dihydroacridine) -phenyl ] -sulfo (DMAC-DPS) (20 nm)/diphenylphosphinoxide-4- (triphenylsilylphenyl) phenyl (TSPO1) (5nm)/1,3,5-tris (N-phenylbenzimidazol-2-yl) benzene (TPBi) (35nm)/LiF (1nm)/Al (100 nm). Wherein the host material in the light emitting layer is material 1 prepared in the above example. The current density-voltage-luminance curves of the TADF OLEDs are shown in fig. 6. The efficiency curves of the TADF OLEDs provided by the present invention are shown in fig. 7.
The results of the tests of examples 2 and 3 are shown in the following table:
Figure BDA0002392662040000041

Claims (7)

1. a bipolar organic photoelectric material based on an N-C ═ O resonance structure is disclosed, and the molecular structure general formula is shown as I:
Figure FDA0002392662030000011
in the formula, R1And R2The same or different, each is a hydrogen atom, a bromine atom or a tert-butyl group.
2. The bipolar organic photoelectric material based on an N-C ═ O resonance structure according to claim 1, which is any one of:
Figure FDA0002392662030000012
3. the method for preparing an N-C ═ O resonance structure-based bipolar organic photoelectric material according to claim 1, wherein: carbazole or bromocarbazole or tert-butylcarbazole and N, N-carbonyldiimidazole are used as raw materials, an organic solvent is added under the protection of inert gas, heating and stirring are carried out, after the reaction is finished, the reaction product is cooled to room temperature, deionized water is added to the reaction product to separate out white precipitate, suction filtration is carried out, white solid is collected and dissolved, after drying, filtration is carried out, filtrate is concentrated and purified by column chromatography,
the synthetic route is as follows:
Figure FDA0002392662030000013
4. the method for preparing an N-C ═ O resonance structure-based bipolar organic photoelectric material according to claim 3, wherein: the molar ratio of carbazole or bromocarbazole or tert-butylcarbazole to N, N-carbonyldiimidazole is 1-1.2: 1.
5. the method for preparing an N-C ═ O resonance structure-based bipolar organic photoelectric material according to claim 3, wherein: the organic solvent is dimethyl sulfoxide.
6. The method for preparing an N-C ═ O resonance structure-based bipolar organic photoelectric material according to claim 3, wherein: the reaction temperature is 100-120 ℃.
7. Use of the ambipolar organic optoelectronic material based on N-C ═ O resonant structure according to claim 1 in organic electroluminescent devices.
CN202010119982.1A 2020-02-26 2020-02-26 Bipolar organic photoelectric material based on N-C = O resonance structure and preparation method and application thereof Pending CN111217740A (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104212439A (en) * 2014-08-15 2014-12-17 南京邮电大学 Photoelectric function material with N-P=S resonant structure, preparation method and application
KR20160069021A (en) * 2014-12-05 2016-06-16 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
CN109651435A (en) * 2018-12-20 2019-04-19 南京邮电大学 A kind of bipolarity organic photoelectric functional material and preparation method
CN110511177A (en) * 2019-09-16 2019-11-29 南京邮电大学 A kind of D-A type TADF material and its preparation method and application

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104212439A (en) * 2014-08-15 2014-12-17 南京邮电大学 Photoelectric function material with N-P=S resonant structure, preparation method and application
KR20160069021A (en) * 2014-12-05 2016-06-16 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
CN109651435A (en) * 2018-12-20 2019-04-19 南京邮电大学 A kind of bipolarity organic photoelectric functional material and preparation method
CN110511177A (en) * 2019-09-16 2019-11-29 南京邮电大学 A kind of D-A type TADF material and its preparation method and application

Non-Patent Citations (3)

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Title
ANNA M.WAGNER ET AL.: "A copper(II)-catalyzed, sequential Michael-aldol reaction for the preparation of 1,2-dihydroquinolines", 《TETRAHEDRON LETTERS》 *
CRAIG A. MERLIC ET AL.: "Benzannulation reactions of Fischer carbene complexes for the synthesis of indolocarbazoles", 《TETRAHEDRON》 *
JAN BERGMAN ET AL.: "The reaction of indole and the indole Grignard reagent with phosgene. A facile synthesis of indole-3-carboxylic acid derivatives", 《JOURNAL OF HETEROCYCLIC CHEMISTRY》 *

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