CN112778081B - Compound for organic luminescence and application thereof - Google Patents

Compound for organic luminescence and application thereof Download PDF

Info

Publication number
CN112778081B
CN112778081B CN202011588581.7A CN202011588581A CN112778081B CN 112778081 B CN112778081 B CN 112778081B CN 202011588581 A CN202011588581 A CN 202011588581A CN 112778081 B CN112778081 B CN 112778081B
Authority
CN
China
Prior art keywords
compound
cyano
hole injection
fluoro
groups
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN202011588581.7A
Other languages
Chinese (zh)
Other versions
CN112778081A (en
Inventor
张双
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EverDisplay Optronics Shanghai Co Ltd
Original Assignee
EverDisplay Optronics Shanghai Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EverDisplay Optronics Shanghai Co Ltd filed Critical EverDisplay Optronics Shanghai Co Ltd
Priority to CN202011588581.7A priority Critical patent/CN112778081B/en
Publication of CN112778081A publication Critical patent/CN112778081A/en
Application granted granted Critical
Publication of CN112778081B publication Critical patent/CN112778081B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/18—Polycyclic aromatic halogenated hydrocarbons
    • C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/35—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C255/47—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of rings being part of condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C43/192—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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]
    • H10K50/17—Carrier injection layers
    • 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
    • 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
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • 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
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems

Abstract

The first aspect of the present invention provides a compound for organic light emission, the compound having a structure represented by formula (I):
Figure DDA0002866480910000011
wherein R is 1 ‑R 16 Each independently selected from fluoro, cyano, trifluoromethyl, dicyanovinyl, or alkyl, alkoxy, aryl or heteroaryl substituted with fluoro, cyano or trifluoromethyl. The compound has good cross super-conjugated characteristic, and strong electron-withdrawing groups such as fluorine groups, cyano groups and the like combined on the compound can endow molecules with stronger reduction potential, so that the compound assists a hole transport layer to efficiently inject holes, and is suitable for a hole injection auxiliary material of an organic electroluminescent device.

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
Energy level matching is crucial for organic electroluminescent devices, and a stack structure of the organic electroluminescent device, such as a classical organic electroluminescent device, includes: the cathode, the electron transport layer, the light emitting layer, the hole transport layer and the anode are made of ITO, but the work function is high, and the energy level difference from most hole transport materials is about 0.4 eV. Therefore, if a hole injection layer is added between the anode and the hole transport layer, on one hand, the injection of charges can be increased, and on the other hand, the overall efficiency and the service life of the device can be improved.
Of course, doping some strong oxidant into the hole transport layer as a hole injection layer is also another way to improve the hole injection efficiency of the organic electroluminescent device. However, this method requires energy levels of a host material and a dopant material, and generally, the HOMO level of the host material needs to be close to the LUMO level of the guest material, so that electrons at the HOMO level can jump to the LUMO level of the dopant, and thus, a free hole is formed in a hole transport layer, and the conductivity of the device is improved. Meanwhile, the doping can bend the interface energy band, and holes can be injected in a tunneling mode. As for the selection of the dopant, lewis acid type metal complexes, halogens, limonene and quinones are common, and the metal complexes and halogens have the defects of instability during device processing and the like. The allyl compounds have more steps in the synthesis and higher cost.
Therefore, a compound for organic light emission and its application are needed.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provide a compound for organic light emission and application thereof.
In order to realize the purpose, the invention adopts the technical scheme that:
in a first aspect of the present invention, there is provided a compound for organic light emission, the compound having a structure represented by formula (I):
Figure BDA0002866480900000021
wherein R is 1 -R 16 Each independently selected from fluoro, cyano, trifluoromethyl, dicyanovinyl, or alkyl, alkoxy, aryl or heteroaryl substituted with fluoro, cyano or trifluoromethyl.
Preferably, R2 to R5 and R8 to R15 are fluoro groups.
Preferably, R1, R6, R7 and R16 are selected from fluoro, cyano, trifluoromethyl, trifluoroethyl, trifluoromethoxy, dicyanovinyl.
Preferably, the compound is selected from:
Figure BDA0002866480900000022
a second aspect of the present invention provides a hole injecting material comprising the compound as described above.
A third aspect of the invention is to provide a hole injection layer comprising a hole injection material as described above.
A fourth aspect of the invention provides an OLED device comprising a hole injection layer as described above.
By adopting the technical scheme, compared with the prior art, the invention has the following technical effects:
the compound has good cross super-conjugated characteristic, and strong electron-withdrawing groups such as fluorine groups, cyano groups and the like combined on the compound can endow molecules with stronger reduction potential, so that the compound assists a hole transport layer to efficiently inject holes, and is suitable for a hole injection auxiliary material of an organic electroluminescent device.
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 derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection 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 BDA0002866480900000031
To a reaction flask was added Cu powder (1.00g, 15.63mmol), reactant A1 (1.00g, 2.35mmol), reactant A2 (1.00g, 4.00mmol) and 10mL toluene, heated at 130 ℃ under reflux for 72 hours, cooled, toluene removed, dichloromethane added, washed with water, dried, the crude product was passed through a column using hexane/ethyl acetate (10) as eluent, and finally purified to give compound 1.
By measurement, MS:615.97;
13C-NMR：(2C，108.1)，(2C，109.2)，(2C，119.6)，(2C，120.1)，(4C，123.0)，(4C，136.5)，(2C，137.4)，(2C，144.5)，(2C，145.1)，(2C，146.3)，(2C，150.3)。
example 2
Figure BDA0002866480900000041
To a reaction flask was added Cu powder (1.00, 15.63 mmol), reactant B1 (1.00g, 2.27mmol), reactant B2 (1.00g, 3.79mmol) and 10mL toluene, heated at 130 ℃ under reflux for 72 hours, cooled, toluene removed, dichloromethane added, washed with water, dried, the crude product was passed through a column using hexane/ethyl acetate (10) as eluent, and finally purified to give compound 2.
By measurement, MS:643.99;
13C-NMR：(2C，101.8)，(2C，105.8)，(4C，117.2)，(2C，119.6)，(2C，120.1)，(4C，123.0)，(4C，136.5)，(2C，137.4)，(2C，144.5)，(2C，145.1)，(2C，156.6)，(2C，157.7)。
example 3
Figure BDA0002866480900000042
To a reaction flask was added Cu powder (1.00, 15.63 mmol), reactant C1 (1.00g, 1.90mmol), reactant C2 (1.00g, 2.86mmol) and 10mL toluene, heated at 130 ℃ to reflux for 72 hours, cooled, toluene removed, dichloromethane added, washed with water, dried, the crude product was passed to a column, using hexane/ethyl acetate (10) as eluent, and finally purified to give compound 3.
By measurement, MS:815.96;
13C-NMR：(2C，116.1)，(2C，116.7)，(2C，119.6)，(2C，120.1)，(4C，123.0)，(2C，128.3)，(2C，132.3)，(2C，135.0)，(2C，136.1)，(4C，136.5)，(2C，137.4)，(2C，144.5)，(2C，145.1)。
example 4
Figure BDA0002866480900000051
To a reaction flask was added Cu powder (1.00, 15.63 mmol), reactant D1 (1.00g, 1.81mmol), reactant D2 (1.00g, 2.65mmol) and 10mL toluene, heated at 130 ℃ under reflux for 72 hours, cooled, toluene removed, dichloromethane added, washed with water, dried, the crude product was passed through a column, using hexane/ethyl acetate (10) as eluent, and finally purified to give compound 4.
By measurement, MS:872.02;
13C-NMR：(2C，42.8)，(2C，43.4)，(2C，111.6)，(2C，111.7)，(2C，119.6)，(2C，120.1)，(4C，123.0)，(2C，132.9)，(2C，134.2)，(2C，135.3)，(4C，136.5)，(2C，136.9)，(2C，137.4)，(2C，144.5)，(2C，145.1)。
example 5
Figure BDA0002866480900000061
To a reaction flask was added Cu powder (1.00, 15.63 mmol), reactant E1 (1.00g, 1.79mmol), reactant E2 (1.00g, 2.62mmol) and 10mL toluene, heated at 130 ℃ under reflux for 72 hours, cooled, toluene removed, dichloromethane added, washed with water, dried, the crude product was passed to a column, using hexane/ethyl acetate (10) as eluent, and finally purified to give compound 5.
By measurement, MS:879.94;
13C-NMR：(2C，103.5)，(2C，104.6)，(2C，118.5)，(2C，118.6)，(2C，119.6)，(2C，120.1)，(4C，123.0)，(4C，136.5)，(2C，137.4)，(2C，144.5)，(2C，145.1)，(2C，148.3)，(2C，152.3)。
example 6
Figure BDA0002866480900000062
To a reaction flask was added Cu powder (1.00, 15.63 mmol), reactant F1 (1.00g, 1.85mmol), reactant F2 (1.00g, 2.73mmol) and 10mL toluene, heated at 130 ℃ under reflux for 72 hours, cooled, toluene removed, dichloromethane added, washed with water, dried, the crude product was passed through a column using hexane/ethyl acetate (10) as eluent, and finally purified to give compound 6.
By measurement, MS:848.04;
13C-NMR：(4C，82.1)，(8C，117.2)，(2C，119.6)，(2C，120.1)，(4C，123.0)，(2C，132.5)，(2C，135.4)，(8C，136.5)，(2C，137.4)，(2C，144.5)，(2C，145.1)，(4C，165.3)。
detection examples
The hole injection performance of the above examples and comparative example 1 was characterized by the LUMO level by the following specific method: the energy gap Eg of the material was obtained by UV visible tester (Perking-Elemer 750) (Eg = 1240/band edge absorption); obtaining the HOMO energy level of the material through an ultraviolet-visible photon Spectroscopy (Ultra-Violet photon Spectroscopy); calculating the LUMO value according to the relationship among HOMO, LUMO and Eg, specifically: LUMO = HOMO + Eg).
Comparative example 1 is:
Figure BDA0002866480900000071
the specific detection data are as follows:
TABLE 1
Examples LUMO energy level (eV)
Example 1 -5.1
Example 2 -5.3
Example 3 -5.2
Example 4 -5.2
Example 5 -5.2
Example 6 -5.3
Comparative example 1 -5.1
In summary, the compound of the present invention has good cross-over super-conjugation property, and the strong electron-withdrawing groups such as fluoro group and cyano group combined on the compound can provide a strong reduction potential to the molecule, thereby assisting the hole transport layer to perform hole injection efficiently, and being suitable for the hole injection auxiliary material of the organic electroluminescent device.
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 FDA0003765814630000011
2. a hole injecting material comprising the compound according to claim 1.
3. A hole injection layer comprising the hole injection material according to claim 2.
4. An OLED device comprising the hole injection layer of claim 3.
CN202011588581.7A 2020-12-28 2020-12-28 Compound for organic luminescence and application thereof Active CN112778081B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202011588581.7A CN112778081B (en) 2020-12-28 2020-12-28 Compound for organic luminescence and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202011588581.7A CN112778081B (en) 2020-12-28 2020-12-28 Compound for organic luminescence and application thereof

Publications (2)

Publication Number Publication Date
CN112778081A CN112778081A (en) 2021-05-11
CN112778081B true CN112778081B (en) 2022-11-25

Family

ID=75753122

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202011588581.7A Active CN112778081B (en) 2020-12-28 2020-12-28 Compound for organic luminescence and application thereof

Country Status (1)

Country Link
CN (1) CN112778081B (en)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3870102B2 (en) * 2001-02-22 2007-01-17 キヤノン株式会社 Organic light emitting device
KR101950855B1 (en) * 2015-09-22 2019-02-22 주식회사 엘지화학 New compound and organic light emitting device comprising the same
US10953369B2 (en) * 2018-03-08 2021-03-23 Georgia Tech Research Corporation Spirocentric compounds and polymers thereof

Also Published As

Publication number Publication date
CN112778081A (en) 2021-05-11

Similar Documents

Publication Publication Date Title
EP2273512B1 (en) Conjugated polymers comprising triarylamine-arylenevinylene units, synthesis and use of the same
Huang et al. Construction of efficient blue AIE emitters with triphenylamine and TPE moieties for non-doped OLEDs
EP1761962B1 (en) Organic electroluminescent device
EP3042943B1 (en) Composition for organic optoelectronic device, organic optoelectronic device, and display device
EP2838930B1 (en) Polymers containing substituted oligo-triarylamine units and electroluminescence devices containing such polymers
EP1663919B1 (en) Compounds based on fluoranthene and use thereof
EP2315792B1 (en) Electroluminescent polymers, method for the production thereof, and use thereof
EP2998301A1 (en) Organic compound, organic optoelectronic element, and display device
KR20160060572A (en) Organic electroluminescent compound, ink composition, organic electroluminescent device and electric apparatus
DE102009005288A1 (en) Materials for organic electroluminescent devices
WO2018234220A1 (en) Materials for electronic devices
WO2012089294A1 (en) Materials for organic electroluminescence devices
CN102276525B (en) Triphenylamine-substituted pyridine derivatives and preparation method and application thereof
CN113087711B (en) Organic electroluminescent materials and devices
KR101781114B1 (en) Organic electronic materials
EP3686186A1 (en) Compound, coating composition comprising same, and organic light emitting diode
CN112778081B (en) Compound for organic luminescence and application thereof
KR101691713B1 (en) Organic solar cell and method for preparing the same
KR101739831B1 (en) Organic electroluminescent compound, ink composition, organic electroluminescent device and electric apparatus
Chuang et al. Synthesis and characterization of fluorene-derived PU as a thermo cross-linked hole-transporting layer for PLED
CN111148791B (en) Novel polymer and organic light emitting device comprising the same
Laurinaviciute et al. Hole-transporting phenothiazine-based hydrazones with reactive vinylbenzyl groups
CN111848624A (en) Benzodiimidazole compound, hole injection material, OLED device and preparation method and application thereof
CN110938085A (en) Axis compound and preparation method and application thereof
CN113620842A (en) Hole injection material

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant