CN118084953A - Organic compound, light-emitting element, and display panel - Google Patents

Organic compound, light-emitting element, and display panel Download PDF

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Publication number
CN118084953A
CN118084953A CN202410199970.2A CN202410199970A CN118084953A CN 118084953 A CN118084953 A CN 118084953A CN 202410199970 A CN202410199970 A CN 202410199970A CN 118084953 A CN118084953 A CN 118084953A
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compound
substituted
carbon atoms
organic compound
unsubstituted
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何锐锋
吴灿洁
何科威
宋晶尧
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TCL China Star Optoelectronics Technology Co Ltd
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TCL China Star Optoelectronics Technology Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • 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
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • H10K85/658—Organoboranes

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  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Organic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The embodiment of the invention discloses an organic compound, a light-emitting element and a display panel, wherein the organic compound has a structure shown as a general formula (1): according to the general formula (1), the organic compound with the structure shown in the general formula (1) has a cyclopentyl structure, so that the hole transmission performance and resonance performance of the organic compound are enhanced, the intermolecular distance is effectively increased, exciton quenching caused by intermolecular accumulation is inhibited, the luminous efficiency of a luminous element is improved, and the service life of the luminous element is prolonged.

Description

Organic compound, light-emitting element, and display panel
Technical Field
The invention relates to the field of display, in particular to an organic compound, a light-emitting element and a display panel.
Background
At present, an organic electroluminescent element generally has a positive electrode, a negative electrode, and an organic layer therebetween, and organic substances of the organic layer are used to convert electric energy into light energy, thereby realizing organic electroluminescence. A voltage is applied between the positive electrode and the negative electrode of the organic electroluminescent element, the positive electrode injects holes into the organic layer, the negative electrode injects electrons into the organic layer, the injected holes meet the electrons to form excitons, and the excitons emit light when transiting to the ground state, thereby realizing the light emission of the organic electroluminescent element. The organic electroluminescent element has the characteristics of self-luminescence, high brightness, high efficiency, low-voltage driving, wide viewing angle, high contrast, high response and the like, so that the organic electroluminescent device has wide application prospect.
In order to improve the luminous efficiency of the organic electroluminescent element, various luminescent material systems based on fluorescence and phosphorescence have been developed. However, the organic electroluminescent element using an organic compound (e.g., an organic compound as a light-emitting material, etc.) has limited improvement in performance both in terms of efficiency and lifetime, resulting in that the organic electroluminescent element using an organic compound still has room for improvement in light-emitting efficiency and lifetime.
Accordingly, there is a need for an organic compound, a light emitting element, and a display panel to solve the above-mentioned problems.
Disclosure of Invention
The invention provides an organic compound, a light-emitting element and a display panel, which can relieve the technical problems that the light-emitting efficiency and the service life of the current organic electroluminescent element are difficult to improve.
The present invention provides an organic compound having a structure represented by the general formula (1):
Wherein Z is selected from CR 1R2、NR3, O or S;
X, Y are each independently selected from O or NR 4;
Each occurrence of R 1、R2、R3、R4 is independently selected from: substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 5 to 30 carbon atoms, R 1 and R 2 are cyclic or acyclic;
Ar 1 is selected from: H. d, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aromatic group of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic group of 5 to 30 carbon atoms;
Ar 2 is selected from: a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms.
Preferably, the organic compound has a structure as shown in any one of the general formulae (2-1) to (2-6):
preferably, at least one of X and Y is selected from NR 4.
Preferably, each occurrence of R 4 is independently selected from: a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 carbon atoms.
Preferably, each occurrence of R 1、R2、R3 is independently selected from: substituted or unsubstituted alkyl having 1 to 12 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 5 to 20 carbon atoms, R 1 and R 2 are cyclic or acyclic.
Preferably, ar 1 is selected from: H. d, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 carbon atoms;
ar 2 is selected from: a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 carbon atoms.
Preferably, the organic compound is selected from the following compounds:
the present invention also provides a light emitting element including:
a pair of electrodes including a first electrode and a second electrode;
an organic functional layer located between the first electrode and the second electrode;
wherein the material of the organic functional layer comprises at least one organic compound as described above.
Preferably, the organic functional layer comprises at least a light emitting layer comprising at least one organic compound as described above.
The invention also provides a display panel comprising the light-emitting element.
The organic compound with the structure shown in the general formula (1) has a cyclopentyl structure, so that the hole transmission performance and resonance performance of the organic compound are enhanced, and meanwhile, the intermolecular distance is effectively increased, thus the exciton quenching caused by intermolecular accumulation is inhibited, the luminous efficiency of a luminous element is improved, and the service life of the luminous element is prolonged.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings required for the description of the embodiments will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
Fig. 1 is a schematic structural diagram of a light emitting device according to an embodiment of the present invention.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to fall within the scope of the invention. Furthermore, it should be understood that the detailed description is presented herein for purposes of illustration and description only, and is not intended to limit the invention. In the present invention, unless otherwise indicated, terms of orientation such as "upper" and "lower" are used to generally refer to the upper and lower positions of the device in actual use or operation, and specifically the orientation of the drawing figures; while "inner" and "outer" are for the outline of the device. In the present invention, "optional" and "optional" refer to the existence or nonexistence of the solution, that is, any one of the two parallel solutions "existence" or "nonexistence" is selected, if multiple "optional" solutions occur in one solution, if no special description exists, and no contradiction or mutual constraint relation exists, each "optional" is independent. In the invention, the technical characteristics described in an open mode comprise a closed technical scheme composed of the listed characteristics and also comprise an open technical scheme comprising the listed characteristics.
In the present invention, the aromatic groups, aromatic groups and aromatic ring systems have the same meaning and can be interchanged.
In the present invention, the heteroaromatic groups, heteroaromatic groups and heteroaromatic ring systems have the same meaning and can be interchanged.
In the present invention, "substituted" means that a hydrogen atom in a substituent is replaced with a substituent.
In the present invention, the same substituent may be independently selected from different groups when it appears multiple times. If the general formula contains a plurality of R, R can be independently selected from different groups.
In the present invention, "substituted or unsubstituted" means that the defined group may or may not be substituted. "unsubstituted" means that H in the defined group is not replaced by another atom or group. When a defined group is substituted, it is understood that the defined group may be substituted with one or more substituents R selected from, but not limited to: deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1 to 20 carbon atoms, heterocyclyl containing 3 to 20 ring atoms, aromatic containing 6 to 20 ring atoms, heteroaromatic containing 5 to 20 ring atoms, -NR' R ", silane, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and which may be further substituted with substituents acceptable in the art; it is understood that R 'and R "in-NR' R" are each independently selected from, but not limited to: H. deuterium atoms, cyano groups, isocyano groups, nitro groups or halogen groups, alkyl groups containing 1 to 10 carbon atoms, heterocyclic groups containing 3 to 20 ring atoms, aromatic groups containing 6 to 20 ring atoms, heteroaromatic groups containing 5 to 20 ring atoms. Preferably, R is selected from, but not limited to: deuterium atoms, cyano groups, isocyano groups, nitro groups or halogen groups, alkyl groups having 1 to 10 carbon atoms, heterocyclic groups having 3 to 10 ring atoms, aromatic groups having 6 to 20 ring atoms, heteroaromatic groups having 5 to 20 ring atoms, silane groups, carbonyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, carbamoyl groups, haloformyl groups, formyl groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups, trifluoromethyl groups, and the above groups may be further substituted with substituents acceptable in the art.
In the present invention, the "number of ring atoms" means the number of atoms among atoms constituting the ring itself of a structural compound (for example, a monocyclic compound, a condensed cyclic compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound) in which atoms are bonded to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below, unless otherwise specified. For example, the number of ring atoms of the benzene ring is 6, the number of ring atoms of the naphthalene ring is 10, and the number of ring atoms of the thienyl group is 5.
In the present invention, the term "aryl group or aromatic group" means an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, and may be a monocyclic aryl group, a condensed ring aryl group, or a polycyclic aryl group, at least one of which is an aromatic ring system. For example, "substituted or unsubstituted aryl group having 6 to 40 ring atoms" means an aryl group having 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluoranthryl, triphenylenyl, pyrenyl, perylenyl, tetracenyl, fluorenyl, perylenyl, acenaphthylenyl and derivatives thereof. It will be appreciated that a plurality of aryl groups may also be interrupted by short non-aromatic units (e.g. <10% of non-H atoms, such as C, N or O atoms), such as acenaphthene, fluorene, or 9, 9-diaryl fluorene, triarylamine, diaryl ether systems in particular should also be included in the definition of aryl groups.
In the present invention, "heteroaryl or heteroaromatic group" means that at least one carbon atom is replaced by a non-carbon atom on the basis of an aryl group, and the non-carbon atom may be an N atom, an O atom, an S atom, or the like. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" refers to heteroaryl having 5 to 40 ring atoms, preferably substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, particularly preferably substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl is optionally further substituted, suitable examples include, but are not limited to: thienyl, furyl, pyrrolyl, imidazolyl, diazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, phthalazinyl, phenanthridinyl, primary pyridyl, quinazolinone, dibenzothienyl, dibenzofuranyl, carbazolyl, and derivatives thereof.
In the present invention, "alkyl" may mean a straight chain, branched and/or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. The phrase containing the term, for example, "C 1-9 alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, which at each occurrence may be, independently of one another, C 1 alkyl, C 2 alkyl, C 3 alkyl, C 4 alkyl, C 5 alkyl, C 6 alkyl, C 7 alkyl, C 8 alkyl, or C 9 alkyl. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3, 7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyl eicosanyl, 2-butyl eicosanyl, 2-hexyl eicosanyl, 2-octyl eicosanyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, adamantyl, and the like.
In the present invention, "amine group" refers to derivatives of amines having the structural features of formula-N (X) 2, wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, or the like. Non-limiting types of amine groups include-NH 2, -N (alkyl) 2, -NH (alkyl), -N (cycloalkyl) 2 -NH (cycloalkyl), -N (heterocyclyl) 2, -NH (heterocyclyl), -N (aryl) 2 -NH (aryl), -N (alkyl) (heterocyclyl), -N (cycloalkyl) (heterocyclyl), -N (aryl) (heteroaryl), -N (alkyl) (heteroaryl), and the like.
In the present invention, as defined herein, hydroxyl means-OH, carboxyl means-COOH, carbonyl means-C (=o) -, amino means-NH 2, formyl means-C (=o) H, haloformyl means-C (=o) Z (wherein Z represents halogen), carbamoyl means-C (=o) NH 2, isocyanate means-NCO, isothiocyanate means-NCS.
In the present invention, "halogen" or "halo" means F, cl, br or I.
In the present invention, the term "alkoxy" refers to a group of the structure "-O-alkyl", i.e. an alkyl group as defined above is attached to other groups via an oxygen atom. Phrases containing this term, suitable examples include, but are not limited to: methoxy (-O-CH 3 or-OMe), ethoxy (-O-CH 2CH3 or-OEt), and t-butoxy (-O-C (CH 3)3 or-OtBu).
In the present invention "×" attached to a single bond represents a linking or fusing site.
In the present invention, the abbreviations of the substituents correspond to: n represents positive, sec represents secondary, i represents different, t represents tertiary, o represents adjacent, m represents intermediate, p represents pair, me represents methyl, et represents ethyl, pr represents propyl, bu represents butyl, am represents pentyl, hx represents hexyl, and Cy represents cyclohexyl.
In the present invention, when no attachment site is specified in a group, an optionally attachable site in the group is represented as an attachment site.
In the present invention, when no condensed site is specified in the group, it means that an optionally condensed site in the group is used as a condensed site, and preferably two or more sites in the group in the ortho position are condensed sites.
In the present invention, when the same group contains a plurality of substituents of the same symbol, each substituent may be the same or different from each other, for exampleThe 6R groups on the benzene ring may be the same or different from each other.
In the present invention, a single bond to which a substituent is attached extends through the corresponding ring, meaning that the substituent may be attached to an optional position on the ring, e.gR in (2) is connected with any substitutable site of benzene ring; such as/>Representation/>Can be associated with/>Optionally forming a fused ring at an optional position on the benzene ring.
The cyclic alkyl or cycloalkyl groups according to the invention have the same meaning and are interchangeable.
In the present invention, "adjacent group" means that there is no substitutable site between two substituents.
In the present invention, "adjacent two R 1 or R 3 or R 5 are each cyclic" means a ring system formed by connecting two adjacent R 1 or R 3 or R 5 to each other, and the ring system may be selected from an aliphatic hydrocarbon ring, an aliphatic heterocyclic ring, an aromatic hydrocarbon ring or an aromatic heterocyclic ring. Preferably, can be formed into
At present, since the performance of the organic compound is to be improved, there is a problem that the luminous efficiency and the lifetime of the organic electroluminescent element having the organic compound still have room for improvement.
The embodiment of the invention provides an organic compound, which has a structure shown as a general formula (1):
Wherein Z is selected from CR 1R2、NR3, O or S;
X, Y are each independently selected from O or NR 4;
Each occurrence of R 1、R2、R3、R4 is independently selected from: substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 5 to 30 carbon atoms, R 1 and R 2 are cyclic or acyclic;
Ar 1 is selected from: H. d, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms;
Ar 2 is selected from: a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms.
The organic compound with the structure shown in the general formula (1) has a cyclopentyl structure, so that the hole transmission performance and resonance performance of the organic compound are enhanced, and meanwhile, the intermolecular distance is effectively increased, thus the exciton quenching caused by intermolecular accumulation is inhibited, the luminous efficiency of a luminous element is improved, and the service life of the luminous element is prolonged.
In some embodiments, the organic compound has a structure as shown in any one of formulas (2-1) to (2-6):
In some embodiments, at least one of X and Y is selected from NR 4. For example, X and Y are both selected from NR 4; or X is selected from NR 4 and Y is selected from O; or X is selected from O and Y is selected from NR 4.
In some embodiments, each occurrence of R 4 is independently selected from: a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 22 carbon atoms.
In some embodiments, each occurrence of R 4 is independently selected from: a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 carbon atoms.
In some embodiments, each occurrence of R 4 is independently selected from: a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 15 carbon atoms.
In some embodiments, each occurrence of R 4 is independently selected from: unsubstituted methyl, unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, or a combination of at least two of the foregoing.
In some embodiments, R 4 is selected from the following structures:
wherein "×" denotes the site of attachment to N.
In some embodiments, each occurrence of R 1、R2 is independently selected from: substituted or unsubstituted alkyl having 1 to 12 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 5 to 20 carbon atoms, R 1 and R 2 are cyclic or acyclic.
In some embodiments, each occurrence of R 1、R2 is independently selected from: a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 15 carbon atoms.
In some embodiments, each occurrence of R 1、R2 is independently selected from: a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 15 carbon atoms.
In some embodiments, each occurrence of R 1、R2 is independently selected from: substituted or unsubstituted methyl, substituted or unsubstituted phenyl.
In some embodiments, when Z is selected from CR 1R2, R 1 is cyclic with R 2 and R 1 is linked to R 2 to form a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms.
In some embodiments, when Z is selected from CR 1R2, R 1 is cyclic with R 2 and R 1 is linked to R 2 to form a substituted or unsubstituted aromatic group having 6 to 15 carbon atoms.
In some embodiments, when Z is selected from CR 1R2, R 1 is cyclic with R 2 and R 1 is linked to R 2 to form a substituted or unsubstituted aromatic group having 6 to 13 carbon atoms.
In some embodiments, when Z is selected from CR 1R2, R 1 is linked to R 2 to form the following structure:
wherein "×" denotes the attachment site to which C is attached.
In some embodiments, each occurrence of R 3 is independently selected from: a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 carbon atoms.
In some embodiments, each occurrence of R 3 is independently selected from: a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 15 carbon atoms.
In some embodiments, each occurrence of R 3 is independently selected from: substituted or unsubstituted chain alkyl groups having 1 to 4 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 14 carbon atoms.
In some embodiments, R 3 is selected from unsubstituted methyl, unsubstituted t-butyl, or the following structure:
wherein "×" denotes a ligation site.
In some embodiments, ar 1 is selected from: H. d, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 26 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 26 carbon atoms.
In some embodiments, ar 1 is selected from: H. d, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 carbon atoms.
In some embodiments, ar 1 is selected from: H. d, a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 15 carbon atoms.
In some embodiments, ar 1 is selected from substituted or unsubstituted alkyl groups having 1 to 8 carbon atoms, preferably from substituted or unsubstituted chain alkyl groups having 1 to 4 carbon atoms.
In some embodiments, ar 1 is selected from H, D, substituted or unsubstituted methyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted tert-pentyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted amine.
In some embodiments, ar 1 is selected from: H. d, unsubstituted methyl, unsubstituted t-butyl, or the structure:
wherein "×" denotes a ligation site.
In some embodiments, ar 2 is selected from: a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 carbon atoms.
In some embodiments, ar 2 is selected from: a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 15 carbon atoms.
In some embodiments, ar 2 is selected from: a substituted or unsubstituted chain alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 10 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 carbon atoms, or a combination of at least two of the foregoing.
In some embodiments, ar 2 is selected from the following structures:
in some embodiments, the organic compound is selected from the following compounds:
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According to the organic compound provided by the embodiment of the invention, the cyclopentyl structure is introduced into the organic compound molecule, so that the hole transmission performance and the resonance performance of the organic compound are enhanced, and meanwhile, the intermolecular distance is effectively increased, so that exciton quenching caused by intermolecular accumulation is inhibited, the luminous efficiency of a luminous element is improved, and the service life of the luminous element is prolonged.
The present invention also provides a mixture comprising at least one organic compound according to any one of the above and an organic functional material selected from at least one of a hole transporting material, a hole injecting material, a hole blocking material, an electron injecting material, an electron transporting material, a host material, or a guest material.
Referring to fig. 1, the present invention further provides a light emitting device, including: a pair of electrodes including a first electrode 101 and a second electrode 102; an organic functional layer 103 located between the first electrode 101 and the second electrode 102; wherein the material of the organic functional layer 103 includes one or more of the organic compounds as described above. The first electrode 101 may be an anode and the second electrode 102 may be a cathode.
In some embodiments, the light emitting element may be used in an organic light emitting diode, an organic photovoltaic cell, an organic light emitting battery, an organic field effect transistor, an organic light emitting field effect transistor, an organic laser, an organic spintronic device, an organic sensor, an organic plasmon emitting diode, and the like, and is preferably an organic light emitting diode, an organic light emitting battery, or an organic light emitting field effect transistor.
In some embodiments, the light emitting element may be applied to a variety of electronic devices, such as: display panels, lighting devices, light sources, etc.
In some embodiments, the organic functional layer 103 may be a single layer, and in this case, the organic functional layer 103 is a mixture layer, and the mixture layer includes a first compound and a second compound, where the first compound is one or more of the organic compounds as described above, and the second compound is one or more of the hole injecting material, the hole transporting material, the electron injecting material, the electron transporting material, the hole blocking material, the light emitting guest material, the light emitting host material, and the organic dye.
In some embodiments, the organic functional layer 103 may include multiple layers. When the organic functional layer 103 is a multilayer, the organic functional layer 103 includes at least a light emitting layer 106; preferably, the organic functional layer 103 includes a hole injection layer 104, a hole transport layer 105, a light emitting layer 106, and an electron transport layer 107.
In some embodiments, the organic functional layer 103 further includes an electron blocking layer between the hole transport layer 105 and the light emitting layer 106; the organic functional layer 103 further includes a hole blocking layer between the light emitting layer 106 and the electron transport layer 107; the organic functional layer 103 further includes an electron injection layer between the electron transport layer 107 and the cathode.
In some embodiments, the hole transport layer 105 is located between the light emitting layer 106 and the first electrode 101, the hole injection layer 104 is located between the hole transport layer 105 and the first electrode 101, and the electron transport layer 107 is located between the light emitting layer 106 and the second electrode 102.
In some embodiments, the light emitting element may be a blue light emitting element, a green light emitting element, or a red light emitting element, and the light emitting layer 106 may include at least one organic compound as described above.
In some embodiments, the light emitting layer 106 may include a host material including a fused aromatic derivative or heteroaromatic compound and a guest material that is one or more of the organic compounds described above.
In some embodiments, the organic compound is used in a light emitting layer of a blue light emitting element.
In some embodiments, the light emitting element emits light at a wavelength between 300 and 1000 nm; further, the light emitting element has a light emitting wavelength of 350 to 900nm; still further, the light emitting element has a light emitting wavelength between 400 and 800 nm; further, the light emitting element emits light in a wavelength range of red light, a wavelength range of green light, or a wavelength range of blue light.
In some embodiments, the host material includes fused aromatic ring derivatives, heterocyclic ring-containing compounds, and the like, such as: at least one of anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives. The host material may be a host material applied to a red light emitting element, a host material applied to a green light emitting element, or a host material applied to a blue light emitting element. Preferably, the host material is a host material applied to a blue light emitting element; when the host material is a host material applied to a blue light-emitting element, the host material is preferably an anthracene-based organic compound.
In some embodiments, the mass ratio of the host material to the guest material is from 99:1 to 70:30, such as: 90:10, 85:15, 80:20, 75:25, etc.; preferably 99:1 to 90:10, such as: 97:3, 96:4, 95:5, 93:7, 92:8, etc. The guest material is dispersed in the host material, and the mass ratio of the host material to the guest material is 99:1 to 70:30, which is advantageous in suppressing crystallization of the light emitting layer 106 and suppressing concentration quenching of the guest material due to high concentration, thereby improving light emitting efficiency of the light emitting element.
In some embodiments, the anode is an electrode that injects holes, and the anode may inject holes into the organic functional layer 103, such as: the anode injects holes into the hole injection layer, the hole transport layer, or the light emitting layer. The anode may include at least one of a conductive metal, a conductive metal oxide, or a conductive polymer. Preferably, the absolute value of the difference in HOMO (highest occupied molecular orbital ) energy levels or valence band energy levels of the light-emitting material in the work function and light-emitting layer of the anode, or of the p-type semiconductor material in the hole injection layer or the hole transport layer or electron blocking layer, is less than 0.5eV, preferably less than 0.3eV, more preferably less than 0.2eV. Materials of the anode include, but are not limited to: al, cu, au, ag, mg, fe, co, ni, mn, pd, pt, ITO (Indium Tin Oxide), aluminum doped zinc Oxide (AZO), or the like, or other suitable and known anode materials, can be readily selected for use by one of ordinary skill in the art. The material of the anode may be deposited using any suitable technique, such as a suitable physical vapor deposition method including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like. In some embodiments, the anode is patternable, such as: patterned ITO conductive substrates are commercially available and can be used to make the light emitting elements of the present invention.
In some embodiments, the cathode is an electron-injecting electrode, and the cathode may inject electrons into the organic functional layer, such as: the cathode injects electrons into the electron injection layer, the electron transport layer, or the light emitting layer. The cathode may include at least one of a conductive metal or a conductive metal oxide. Preferably, the absolute value of the difference between the work function of the cathode and the LUMO (lowest unoccupied molecular orbital ) level or conduction band level of the light-emitting material in the light-emitting layer, or the n-type semiconductor material as an electron injection layer or electron transport layer or hole blocking layer, is less than 0.5eV, preferably less than 0.3eV, more preferably less than 0.2eV. All materials that can be used as cathodes for the organic electronic devices are possible as cathode materials for the devices of the present invention, including but not limited to: al, au, ag, ca, ba, mg, liF/Al, mgAg alloy, baF 2/Al, cu, fe, co, ni, mn, pd, pt, ITO, etc. The material of the cathode may be deposited using any suitable technique, such as a suitable physical vapor deposition method including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.
In some embodiments, the hole injection layer 104 is used to facilitate injection of holes from the anode to the light emitting layer 106, and the hole injection layer 104 includes a hole injection material that is a material that can receive holes injected from the positive electrode at a low voltage, and preferably, the Highest Occupied Molecular Orbital (HOMO) of the hole injection material is between the work function of the material of the anode and the HOMO of the hole injection functional material of the film layer on the side away from the anode (e.g., the hole transport material of the hole transport layer). The hole injection material includes, but is not limited to, at least one of metalloporphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazabenzophenanthrene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, polyaniline-based and polythiophene-based conductive polymer, and the like.
In some embodiments, the hole transport layer 105 may be used to transport holes to the light emitting layer 106, the hole transport layer 105 including a hole transport material that receives holes transported from the anode or the hole injection layer and transfers holes to the light emitting layer. The hole transport material is a material known in the art to have high hole mobility, and may include, but is not limited to, at least one of an arylamine-based organic material, a conductive polymer, a block copolymer having both conjugated and non-conjugated portions, and the like.
In some embodiments, the electron transport layer 107 is configured to transport electrons, and the electron transport layer 107 includes an electron transport material that receives electrons injected from the negative electrode and transfers the electrons to the light emitting layer 106. The electron transport material is a material known in the art having high electron mobility, which may include, but is not limited to: at least one of Al complexes of 8-hydroxyquinoline, complexes comprising Alq3, organic radical compounds, hydroxyflavone-metal complexes, lithium 8-hydroxyquinoline (LiQ), and benzimidazole-based compounds.
In some embodiments, the electron injection layer is used to inject electrons, and the electron injection layer includes an electron injection material, preferably a material having an ability to transport electrons, having an effect of injecting electrons from a negative electrode, having an excellent effect of injecting electrons into the light emitting layer 106 or the light emitting material, and having an ability to prevent excitons generated by the light emitting layer 106 from moving to the hole injection layer, and also having an excellent ability to form a thin film. The electron injection material includes, but is not limited to, at least one of lithium 8-hydroxyquinoline (LiQ), fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxazole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylene methane, anthrone, etc. and derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc.
In some embodiments, the hole blocking layer is used to block holes from reaching the negative electrode, and may generally be formed under the same conditions as the hole injection layer 104. The hole blocking layer includes a hole blocking material including, but not limited to, at least one of an diazole derivative or triazole derivative, a phenanthroline derivative, BCP, an aluminum complex, and the like.
In some embodiments, the light emitting element further includes a substrate 108, and the first electrode 101, the hole injection layer 104, the hole transport layer 105, the light emitting layer 106, the electron transport layer 107, and the second electrode 102 are sequentially stacked on the substrate 108.
In some embodiments, the substrate 108 may be a transparent substrate or an opaque substrate, and when the substrate 108 is a transparent substrate, a transparent light emitting element may be fabricated; the substrate 108 may be a rigid substrate or a flexible substrate having elasticity, and the material of the substrate 108 may include, but is not limited to, plastic, polymer, metal, semiconductor wafer, glass, or the like. Preferably, the substrate 108 includes at least one smooth surface for forming the anode thereon. More preferably, the surface is free of surface defects. Preferably, the material of the substrate 108 is a polymer film or plastic, including but not limited to polyethylene terephthalate (PET material) and polyethylene glycol (2, 6-naphthalene) (PEN material), and the glass transition temperature of the substrate 108 is greater than or equal to 150 ℃, preferably greater than or equal to 200 ℃, more preferably greater than or equal to 250 ℃, and most preferably greater than or equal to 300 ℃.
In some embodiments, the light emitting element may be a solution-type light emitting element, i.e., at least one of the organic functional layers is prepared by printing (e.g., ink-jet printing).
In some embodiments, the material of the organic functional layer, the material of the mixture layer, or the material of the light emitting layer may be prepared by a composition, and the preparation process may be a printing or coating process. Printing or coating processes include ink jet Printing, jet Printing (stencil Printing), screen Printing, dip coating, spin coating, doctor blade coating, roll Printing, twist roller Printing, offset Printing, flexography, rotary Printing, spray coating, brush or pad Printing, slot die coating, and the like. Preferably, gravure printing, inkjet printing and inkjet printing.
The composition may be a solution or suspension, and the composition may include a dispersoid and a dispersing agent. Wherein the dispersoid is one or more than one of the organic compounds as described above, and the dispersing agent is used for dispersing the dispersoid.
In the composition, the mass fraction of the organic compound as described above may be 0.3% to 30%, preferably 0.5% to 20%, more preferably 0.5% to 15%, still more preferably 0.5% to 10%, most preferably 1% to 5%.
When the composition is used in a printing process, the composition may be an ink, the viscosity and surface tension of which are important parameters, and the surface tension parameters of a suitable ink are suitable for a particular substrate and a particular printing method. In some embodiments, the ink has a surface tension in the range of 19dyne/cm to 50dyne/cm at an operating temperature or at 25 ℃; preferably 22dyne/cm to 35dyne/cm; more preferably 25dyne/cm to 33dyne/cm, which is advantageous for use in an inkjet printing process. In some embodiments, the ink has a viscosity in the range of 1cps to 100cps at operating temperature or 25 ℃; preferably 1cps to 50cps; more preferably 1.5cps to 20cps; most preferably from 4.0cps to 20cps, which is advantageous for use in inkjet printing processes.
In some embodiments, the Hansen (Hansen) solubility parameters of the dispersant are within the following ranges: the dispersion agent has a δd (dispersion force) in the range of 17.0 to 23.2MPa 1/2, preferably 18.5 to 21.0MPa 1/2; δp (polar force) is in the range of 0.2 to 12.5MPa 1/2, preferably in the range of 2.0 to 6.0MPa 1/2; δh (hydrogen bonding force) is in the range of 0.9 to 14.2MPa 1/2, preferably in the range of 2.0 to 6.0MPa 1/2.
In some embodiments, the dispersant has a boiling point greater than or equal to 150 ℃; preferably greater than or equal to 180 ℃; and more preferably 200 ℃ or higher; more preferably 250 ℃ or higher; further preferably 275℃or higher, and most preferably 300℃or higher. The dispersant has a boiling point of at least 150 ℃ or more, which is advantageous in preventing clogging of nozzles of an inkjet printhead during inkjet printing, and a higher boiling point is advantageous in preventing clogging.
The dispersant may include at least one organic solvent that is vaporizable from a solvent system to form a film comprising a functional material. The organic solvent may comprise at least one first organic solvent, which may be selected from aromatic or heteroaromatic. Specifically, the first organic solvent may be selected from p-diisopropylbenzene, pentylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1, 4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluenes, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3, 4-tetramethylbenzene, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2, 4-trichlorobenzene, 4-difluorodiphenyl methane, 1, 2-dimethoxy-4- (1-propenyl) benzene, diphenyl methane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α -dichlorodiphenyl methane, 4- (3-phenylpropyl) pyridine, benzyl benzoate, 1, 4-bis (3, 4-dimethylquinoline), ethyl-benzonate, 2-dimethylfuran, and the like.
The first organic solvent may be selected from aromatic ketone solvents. Specifically, the first organic solvent may be selected from 1-tetralone, 2- (phenylepoxy) tetralone, 6- (methoxy) tetralone, acetophenone, propiophenone, benzophenone, and derivatives thereof, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylacetophenone, 3-methylacetone, 2-methylacetone, and the like.
The first organic solvent may be selected from aromatic ether solvents. Specifically, the first organic solvent may be selected from 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1, 2-dimethoxy-4- (1-propenyl) benzene, 1, 4-benzodioxane, 1, 3-dipropylbenzene, 2, 5-dimethoxytoluene, 4-ethylben-ther, 1, 3-dipropoxybenzene, 1,2, 4-trimethoxybenzene, 4- (1-propenyl) -1, 2-dimethoxybenzene, 1, 3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-t-butyl anisole, trans-p-propenyl anisole, 1, 2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, and the like.
The first organic solvent may be selected from aliphatic ketones. Specifically, the first organic solvent may be selected from aliphatic ketones such as 2-nonene, 3-nonene, 5-nonene, 2-decanone, 2, 5-adipone, 2,6, 8-trimethyl-4-nonene, fenchyl ketone, phorone, isophorone, di-n-amyl ketone, and the like; or aliphatic ethers such as amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, and the like.
The first organic solvent may be selected from organic ester solvents. Specifically, the first solvent may be selected from alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkyl lactones, alkyl oleates, and the like. Particular preference is given to octyl octanoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate and the like.
The organic solvent may further include a second organic solvent, and the second organic solvent may be one or more solvents selected from methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1, 4-dioxane, acetone, methyl ethyl ketone, 1,2 dichloroethane, 3-phenoxytoluene, 1-trichloroethane, 1, 2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethylsulfoxide, tetrahydronaphthalene, decalin, indene, and the like.
The composition may include one or more components such as a surface active compound, a lubricant, a wetting agent, a dispersing agent, a hydrophobing agent, an adhesive, etc., in addition to the dispersoid and the dispersing agent, for adjusting viscosity, film forming properties, improving adhesion, etc.
Exemplary methods for preparing the organic compounds provided by the present invention are shown in the following exemplary examples 1 to 18.
Example 1
Organic compoundIs synthesized by (a)
The synthetic route for the organic compound M1 is as follows:
The specific synthetic procedure for the organic compound M1 is as follows:
synthesis of intermediate M1-3:
a solution of (16.2 g,100 mmol) compound M1-1, (31.7 g,100 mmol) compound M1-2, (3.3 g,3 mmol) tetrakis (triphenylphosphine) palladium, (20.6 g,150 mmol) potassium carbonate in 40mL of water and 200mL of toluene under nitrogen was added to a 500mL three-necked flask, and the mixture was heated and stirred to 110℃for reaction for 12 hours; ending the reaction, cooling to room temperature, carrying out suction filtration on the filtrate, and collecting the filtrate; the majority of the solvent in the filtrate was removed by rotary evaporation, the resulting crude product was dissolved with dichloromethane, washed 3 times with water, and the organic phase was collected for column chromatography purification to afford intermediate M1-3 in 73% yield.
Synthesis of intermediate M1-5:
Under the nitrogen environment, adding (18.5 g,60 mmol) compound M1-3 and 150mL anhydrous tetrahydrofuran into a500 mL three-port bottle, cooling to-78 ℃, slowly dropwise adding 65mmol of n-butyllithium, and reacting for 1 hour; the reaction solution was slowly added into a500 mL reaction flask containing (10.8 g,60 mmol) of Compound M1-4 and 100mL of anhydrous tetrahydrofuran, and the reaction was allowed to naturally warm to room temperature, and continued for 6 hours; adding dilute hydrochloric acid aqueous solution into the reaction solution, and continuously stirring to react for 0.5 hour; the reaction solution is subjected to rotary evaporation to remove most of the solvent, the obtained mixture is extracted by using dichloromethane and is washed with water for 3 times, an organic phase is collected, and the obtained mixture is directly used as a raw material for the next reaction without further purification after rotary evaporation.
Synthesis of intermediate M1-6:
Adding the compound M1-5, (80 mmol) acetic acid and 15mL hydrochloric acid obtained in the previous step into a 250mL three-necked flask, heating and stirring to 110 ℃ for reaction for 5 hours; after finishing the reaction, cooling to room temperature, placing the reaction solution in 500mL of purified water, stirring until the product is separated out, and carrying out suction filtration; washing with purified water and ethanol sequentially, collecting residue, and recrystallizing and purifying with a yield of 65%.
Synthesis of intermediate M1-8:
Under nitrogen atmosphere, (11.7 g,30 mmol) of compound M1-6, (16.6 g,30 mmol) of compound M1-7, (0.55 g,0.6 mmol) of compound Pd 2(dba)3, (0.24 g,1.2 mmol) of compound tri-tert-butylphosphine, (4.1 g,45 mmol) of compound sodium tert-butoxide and 100mL of anhydrous toluene solvent were added to a 300mL two-necked flask, heated at 60℃and stirred for reaction for 6 hours; cooling to room temperature, and adding water for quenching; the reaction solution was subjected to rotary evaporation to remove most of the solvent, and the obtained crude product was dissolved in methylene chloride and washed with water for 3 times, and the organic phase was collected for column chromatography purification to obtain intermediate M1-8 in a yield of 72%.
Synthesis of organic compound M1:
Under the nitrogen environment, adding (18.2 g,20 mmol) compound M1-8 and 100mL anhydrous tetrahydrofuran into a 500mL three-port bottle, cooling to-30 ℃, slowly dropwise adding 25mmol of tert-butyllithium solution, and after the dropwise adding is finished, heating to 60 ℃ and stirring for reaction for 2 hours; cooling to-30 ℃, adding 30mmol of boron tribromide at one time, naturally heating to room temperature, and reacting for 1 hour; adding 40mmol of N, N-diisopropylethylamine, slowly heating to 100 ℃ for reaction for 3 hours; ending the reaction, cooling to room temperature, adding sodium acetate water solution to quench the reaction; rotary evaporation is carried out to remove most of the solvent, and the obtained crude product is dissolved by using dichloromethane and washed 3 times; the organic phase is collected, rotary evaporated and purified by column chromatography, and the organic compound M1 is obtained after purification, the yield is 25%, and the results of an atmospheric pressure solid phase analysis probe mass spectrum (ASAP-MS): MS (ASAP) =933.
Example 2
Organic compoundIs synthesized by (a)
The synthetic route for the organic compound M2 is as follows:
the specific synthetic procedure for the organic compound M2 is as follows:
synthesis of intermediate M2-3:
The same or similar synthesis method as that of the compound M1-3, except that: compounds M2-1 and M2-2 replaced compounds M1-1 and M1-2, respectively, in 77% yield.
Synthesis of intermediate M2-5:
Under the nitrogen environment, adding (17.2 g,60 mmol) compound M2-3 and 150mL anhydrous tetrahydrofuran into a 500mL three-port bottle, slowly dropwise adding 130 mmolM-4 under the ice bath condition, naturally heating the reaction to room temperature, and continuing the reaction for 12 hours; adding aqueous hydrochloric acid solution into the reaction solution, and continuously stirring to react for 0.5 hour; the reaction liquid is subjected to rotary evaporation to remove most of the solvent, the obtained crude product is extracted by using dichloromethane and is washed with water for 3 times, an organic phase is collected, and the obtained product is directly used as a raw material for the next reaction without further purification after rotary evaporation.
Synthesis of intermediate M2-6:
The same or similar synthesis method as the compounds M1-6, except that: compound M2-5 was substituted for compound M1-5 in 63% two-step yield.
Synthesis of intermediate M2-9:
the same or similar synthesis method as that of the compound M1-3, except that: compounds M2-7 and M2-8 replaced compounds M1-1 and M1-2, respectively, in 72% yield.
Synthesis of intermediate M2-11:
Under nitrogen atmosphere, (20.7 g,50 mmol) of intermediate M2-9, (14.1 g,50 mmol) of compound M2-10, (1.38 g,1.5 mmol) of compound Pd 2(dba)3, (0.6 g,3 mmol) of compound tri-tert-butylphosphine, (9.1 g,100 mmol) of compound sodium tert-butoxide and 150mL of anhydrous toluene solvent were added to a 500mL two-necked flask, heated at 60℃and stirred for reaction for 6 hours; cooling to room temperature, and adding water for quenching; rotary evaporating the reaction solution to remove most of the solvent, dissolving the obtained crude product by using dichloromethane and washing with water for 3 times; the organic phase was collected for column chromatography purification in 74% yield.
Synthesis of intermediate M2-13:
Under nitrogen atmosphere, (18.5 g,30 mmol) of intermediate M2-11, (4.5 g,30 mmol) of compound M2-12, (0.83 g,0.9 mmol) of compound Pd 2(dba)3, (0.36 g,1.8 mmol) of compound tri-tert-butylphosphine, (5.5 g,60 mmol) of compound sodium tert-butoxide and 150mL of anhydrous toluene solvent are added into a 500mL two-necked flask, heated to 90 ℃ and stirred for reaction for 6 hours; cooling to room temperature, and adding water for quenching; rotary evaporating the reaction solution to remove most of the solvent, dissolving the obtained crude product by using dichloromethane and washing with water for 3 times; the organic phase was collected for column chromatography purification in 70% yield.
Synthesis of intermediate M2-14:
The same or similar synthesis method as the compounds M1-8, except that: compounds M2-6 and 2-13 replaced compounds M1-6 and 1-7 in 72% yield.
Synthesis of organic compound M2:
The same or similar to the synthesis of compound M1, except that: compound M2-14 replaced compound M1-8, and the product obtained after purification was organic compound M2 in 26% yield, MS (ASAP) =624.
Example 3
Organic compoundIs synthesized by (a)
The synthetic route for the organic compound M3 is as follows:
the specific synthetic procedure for the organic compound M3 is as follows:
synthesis of intermediate M3-2:
the synthesis method is the same as or similar to that of the compound M2-13, except that: compound M3-1 replaced compound M2-11 in 70% yield.
Synthesis of intermediate M3-4:
the same or similar synthesis method as that of the compound M1-3, except that: compound M3-3 replaced compound M1-2 in 72% yield.
Synthesis of intermediate M3-5:
Under nitrogen atmosphere, add (16.4 g,60 mmol) of compound M3-4 and (60.6 g,150 mmol) of triethylphosphorus into a 250mL two-necked flask, heat 190 ℃ and stir for reaction for 12 hours; after the completion of the reaction, most of the solvent was distilled off under reduced pressure, and the obtained crude product was dissolved with methylene chloride and washed with water for 3 times, and the organic phase was collected for column chromatography purification in 75% yield.
Synthesis of intermediate M3-7:
Under nitrogen atmosphere, (9.7 g,40 mmol) of compound M3-5, (3.2 g,80 mmol) NaOH and 80mL dimethylformamide were added to a 250mL two-necked flask, and the mixture was stirred and reacted for 1 hour; (11 g,40 mmol) of compound M3-6 was added at a time and reacted for 4 hours with stirring; after the reaction is finished, the reaction solution is placed in 300mL of purified water, the solid obtained by suction filtration after stirring is recrystallized and purified by using a mixed solution of ethanol and dichloromethane, and the yield is 82%.
Synthesis of intermediate M3-8:
The same or similar synthesis method as the compounds M1-8, except that: compounds M3-2 and M3-7 replaced compounds M1-7 and M1-6, respectively, in 74% yield.
Synthesis of organic compound M3:
The same or similar to the synthesis of compound M1, except that: compound M3-8 replaced compound M1-8, and the product obtained after purification was organic compound M3 in 25% yield, MS (ASAP) =774.
Example 4
Organic compoundIs synthesized by (a)
The synthetic route for the organic compound M4 is as follows:
the specific synthetic procedure for the organic compound M4 is as follows:
synthesis of intermediate M4-2:
The same or similar synthesis method as that of the compound M1-3, except that: compounds M2-1 and M4-1 replaced compounds M1-1 and M1-2, respectively, in 71% yield.
Synthesis of intermediate M4-3:
The synthesis method is the same as or similar to that of the compound M3-5, except that: compound M4-2 replaced compound M3-4 in 76% yield.
Synthesis of intermediate M4-4:
The synthesis method is the same as or similar to that of the compound M3-7, except that: compound M4-3 replaces compound M3-5 in 80% yield.
Synthesis of intermediate M4-7:
the synthesis method is the same as or similar to that of the compound M2-11, except that: compounds M4-5 and M4-6 replaced compounds M2-10 and M2-9, respectively, in 78% yield.
Synthesis of intermediate M4-9:
the synthesis method is the same as or similar to that of the compound M2-11, except that: compounds M4-7 and M4-8 replaced compounds M2-10 and M2-9, respectively, in 75% yield.
Synthesis of intermediate M4-10:
the synthesis method is the same as or similar to that of the compound M2-13, except that: compound M4-9 replaces compound M2-11 in 75% yield.
Synthesis of intermediate M4-11:
The same or similar synthesis method as the compounds M1-8, except that: compounds M4-10 and M4-4 replaced compounds M1-7 and M1-6, respectively, in 73% yield.
Synthesis of organic compound M4:
the same or similar to the synthesis of compound M1, except that: compound M4-11 replaced compound M1-8, and the product obtained after purification was organic compound M4 in 26% yield, MS (ASAP) =980.
Example 5
Organic compoundIs synthesized by (a)
The synthetic route for the organic compound M5 is as follows:
the specific synthetic procedure for the organic compound M5 is as follows:
synthesis of intermediate M5-3:
Under nitrogen atmosphere, (24.4 g,100 mmol) of compound M5-1, (20.8 g,100 mmol) of compound M5-2, (1.14 g,6 mmol) of CuI, (13.8 g,100 mmol) of potassium carbonate and 250mL of dimethylformamide are added into a 500mL two-necked flask, heated to 110 ℃ and stirred for reaction for 12 hours; the reaction solution was cooled to room temperature, most of the solvent was removed by rotary evaporation, and the obtained crude product was dissolved with methylene chloride and washed with water for 3 times, and the organic phase was collected for column chromatography purification in 62% yield.
Synthesis of intermediate M5-4:
Under nitrogen atmosphere, (19.4 g,60 mmol) of compound M5-3, (1.14 g,3 mmol) palladium acetate, (10.6 g,60 mmol) sodium carbonate and 150mL dimethylacetamide were added into a 500mL two-necked flask, heated to 170℃and stirred for reaction for 6 hours; the reaction solution was cooled to room temperature, most of the solvent was removed by distillation under reduced pressure, and the obtained crude product was dissolved with methylene chloride and washed with water for 3 times, and the organic phase was collected for column chromatography purification in a yield of 70%.
Synthesis of intermediate M5-5:
the same or similar synthesis method as the compounds M1-8, except that: compounds M3-2 and M5-4 replaced compounds M1-7 and M1-6, respectively, in 72% yield.
Synthesis of organic compound M5:
The same or similar to the synthesis of compound M1, except that: compound M5-5 replaced compound M1-8, and the product obtained after purification was organic compound M5 in 28% yield, MS (ASAP) =718.
Example 6
Organic compoundIs synthesized by (a)
The synthetic route for the organic compound M6 is as follows:
the specific synthetic procedure for the organic compound M6 is as follows:
Synthesis of intermediate M6-3:
The synthesis method is the same as or similar to that of the compound M2-11, except that: compounds M6-1 and M6-2 replaced compounds M2-10 and M2-9, respectively, in 72% yield.
Synthesis of intermediate M6-4:
the synthesis method is the same as or similar to that of the compound M2-13, except that: compound M6-3 replaces compound M2-11 in 68% yield.
Synthesis of intermediate M6-7:
The synthesis method is the same as or similar to that of the compound M5-3, except that: compounds M6-5 and M6-6 replace compounds M5-1 and M5-2, respectively, in 64% yield.
Synthesis of intermediate M6-8:
The same or similar synthesis method as that of the compound M5-4 is different in that: compound M6-7 replaced compound M5-3 in 71% yield.
Synthesis of intermediate M6-9:
the same or similar synthesis method as the compounds M1-8, except that: compounds M6-8 and M6-4 replaced compounds M1-6 and M1-7, respectively, in 68% yield.
Synthesis of organic compound M6:
The same or similar to the synthesis of compound M1, except that: compound M6-9 replaced compound M1-8, and the product obtained after purification was organic compound M6 in 25% yield, MS (ASAP) =963.
Example 7
Organic compoundIs synthesized by (a)
The synthetic route for the organic compound M7 is as follows:
the specific synthetic procedure for the organic compound M7 is as follows:
Synthesis of intermediate M7-2:
the synthesis method is the same as or similar to that of the compound M2-11, except that: compounds M7-1 and M4-6 replaced compounds M2-10 and M2-9, respectively, in 75% yield.
Synthesis of intermediate M7-3:
the synthesis method is the same as or similar to that of the compound M5-3, except that: compound M6-6 replaces compound M5-2 in 62% yield.
Synthesis of intermediate M7-4:
the same or similar synthesis method as that of the compound M5-4 is different in that: compound M7-3 was substituted for compound M5-3 in 74% yield.
Synthesis of intermediate M7-5:
The synthesis method is the same as or similar to that of the compound M2-11, except that: compounds M7-4 and M2-12 replaced compounds M2-9 and 2-10, respectively, in 77% yield.
Synthesis of intermediate M7-6:
the synthesis method is the same as or similar to that of the compound M2-11, except that: compounds M7-5 and M4-8 replaced compounds M2-10 and M2-9, respectively, in 73% yield.
Synthesis of intermediate M7-7:
The same or similar synthesis method as the compounds M1-8, except that: compounds M7-6 and M7-2 replaced compounds M1-6 and M1-7, respectively, in 65% yield.
Synthesis of organic compound M7:
The same or similar to the synthesis of compound M1, except that: compound M7-7 replaced compound M1-8, and the product obtained after purification was organic compound M7 in 27% yield, MS (ASAP) =865.
Example 8
Organic compoundIs synthesized by (a)
The synthetic route for the organic compound M8 is as follows:
The specific synthetic procedure for the organic compound M8 is as follows:
Synthesis of intermediate M8-3:
The synthesis method is the same as or similar to that of the compound M2-11, except that: compound M8-2 and twice the molar amount of M8-1 replaced compounds M2-9 and M2-10, respectively, in 70% yield.
Synthesis of intermediate M8-5:
the synthesis method is the same as or similar to that of the compound M2-13, except that: compounds M8-3 and 8-4 replaced compounds M2-11 and M2-12, respectively, in 74% yield.
Synthesis of intermediate M8-7:
The synthesis method is the same as or similar to that of the compound M5-3, except that: compound M8-6 replaces compound M5-2 in 66% yield.
Synthesis of intermediate M8-8:
The same or similar synthesis method as that of the compound M5-4 is different in that: compound M8-7 replaced compound M5-3 in 76% yield.
Synthesis of intermediate M8-9:
The same or similar synthesis method as the compounds M1-8, except that: compounds M8-8 and M8-5 replaced compounds M1-6 and M1-7, respectively, in 62% yield.
Synthesis of organic compound M8:
Under nitrogen, (23.9 g,30 mmol) of Compound M8-9 and 50mL of o-dichlorobenzene are charged into a 150mL three-necked flask. Slowly dripping 35mmol of boron tribromide under stirring, and reacting for 12 hours at 180 ℃; cooling to room temperature, adding 60mmol of diisopropylethylamine, and reacting at room temperature for 1 hour; the reaction was quenched with water, extracted with dichloromethane and washed three times, and the organic phase was collected for column chromatography purification, and the product obtained after purification was organic compound M8 in 28% yield, MS (ASAP) =804.
Example 9
Organic compoundIs synthesized by (a)
The synthetic route for the organic compound M9 is as follows:
the specific synthetic procedure for the organic compound M9 is as follows:
synthesis of intermediate M9-2:
The synthesis method is the same as or similar to that of the compound M5-3, except that: compounds M6-5 and M9-1 replaced compounds M5-1 and M5-2, respectively, in 64% yield.
Synthesis of intermediate M9-3:
The same or similar synthesis method as that of the compound M5-4 is different in that: compound M9-2 was substituted for compound M5-3 in 73% yield.
Synthesis of intermediate M9-4:
The same or similar synthesis method as the compounds M1-8, except that: compounds M9-3 and M6-4 replaced compounds M1-6 and M1-7, respectively, in 65% yield.
Synthesis of organic compound M9:
The same or similar to the synthesis of compound M1, except that: compound M9-4 replaced compound M1-8, and the product obtained after purification was organic compound M9 in 25% yield, MS (ASAP) =979.
Example 10
Organic compoundIs synthesized by (a)
The synthetic route for the organic compound M10 is as follows:
The specific synthetic procedure for the organic compound M10 is as follows:
synthesis of intermediate M10-2:
the synthesis method is the same as or similar to that of the compound M5-3, except that: compound M10-1 replaced compound M5-2 in 62% yield.
Synthesis of intermediate M10-3:
The same or similar synthesis method as that of the compound M5-4 is different in that: compound M10-2 replaces compound M5-3 in 75% yield.
Synthesis of intermediate M10-5:
The synthesis method is the same as or similar to that of the compound M2-11, except that: compound M10-4 replaced compound M2-9 in 75% yield.
Synthesis of intermediate M10-6:
the synthesis method is the same as or similar to that of the compound M2-13, except that: compound M10-5 replaces compound M2-11 in 70% yield.
Synthesis of intermediate M10-7:
the same or similar synthesis method as the compounds M1-8, except that: compounds M10-3 and M10-6 replaced compounds M1-6 and M1-7, respectively, in 66% yield.
Synthesis of organic compound M10:
The same or similar to the synthesis of compound M1, except that: compound M10-7 replaced compound M1-8, and the product obtained after purification was organic compound M10 in 23% yield, MS (ASAP) =736.
Example 11
Organic compoundIs synthesized by (a)
The synthetic route for the organic compound M11 is as follows:
The specific synthetic procedure for the organic compound M11 is as follows:
Synthesis of intermediate M11-2:
The same or similar synthesis method as that of the compound M1-3, except that: compound M11-1 replaces compound M1-2 in 70% yield.
Synthesis of intermediate M11-3:
the synthesis method is the same as or similar to that of the compound M2-5, except that: compound M11-2 replaces compound M2-3.
Synthesis of intermediate M11-4:
the same or similar synthesis method as the compounds M1-6, except that: compound M11-3 was substituted for compound M1-5 in 61% two-step yield.
Synthesis of intermediate M11-6:
the synthesis method is the same as or similar to that of the compound M8-3, except that: compounds M11-5 and M2-10 replaced compounds M8-2 and M8-1, respectively, in 75% yield.
Synthesis of intermediate M11-7:
Under a nitrogen atmosphere, adding (40 g,60 mmol) of compound M11-6 and 100mL of dichloromethane into a 350mL three-necked flask, slowly adding 100mmol of boron tribromide dichloromethane solution under an ice bath, slowly heating the reaction to room temperature, and continuously stirring the reaction at the room temperature for 24 hours; the reaction was quenched with water, extracted with dichloromethane and washed three times and the organic phase was collected for column chromatography purification in 85% yield.
Synthesis of intermediate M11-8:
The synthesis method is the same as or similar to that of the compound M5-3, except that: compounds M11-4 and M11-7 replaced compounds M5-1 and M5-2, respectively, in 55% yield.
Synthesis of organic compound M11:
the same or similar synthetic method as the compound M8, except that: compound M11-8 replaced compound M8-9, and the product obtained after purification was organic compound M11 in 24% yield, MS (ASAP) =893.
Example 12
Organic compoundIs synthesized by (a)
The synthetic route for the organic compound M12 is as follows:
The specific synthetic procedure for the organic compound M12 is as follows:
Synthesis of intermediate M12-2:
the same or similar synthesis method as that of the compound M1-3, except that: compound M12-1 replaced compound M1-2 in 65% yield.
Synthesis of intermediate M12-3:
the synthesis method is the same as or similar to that of the compound M3-5, except that: compound M12-2 replaces compound M3-4 in 67% yield.
Synthesis of intermediate M12-5:
Under nitrogen atmosphere, (9.7 g,40 mmol) of compound M12-3, (10.8 g,40 mmol) of compound M12-3, (1.1 g,2 mmol) of bis (dibenzylideneacetone) palladium, (0.8 g,4 mmol) of tri-tert-butylphosphine, (7.7 g,80 mmol) of sodium tert-butoxide and 100mL of toluene were added to a 250mL three-necked flask, and reflux reaction was carried out for 12 hours; the reaction solution was cooled to room temperature, most of the solvent was removed by rotary evaporation, and the obtained crude product was extracted with methylene chloride and washed three times with water, and the organic phase was collected for column chromatography purification in 82% yield.
Synthesis of intermediate M12-7:
The synthesis method is the same as or similar to that of the compound M5-3, except that: compounds M4-8 and M12-5 replaced compounds M5-1 and M5-2, respectively, in 58% yield.
Synthesis of intermediate M12-8:
the synthesis method is the same as or similar to that of the compound M2-13, except that: compound M12-7 replaces compound M2-11 in 72% yield.
Synthesis of intermediate M12-9:
The same or similar synthesis method as the compounds M1-8, except that: compounds M12-5 and M12-8 replaced compounds M1-6 and M1-7, respectively, in 67% yield.
Synthesis of organic compound M12:
the same or similar to the synthesis of compound M1, except that: compound M12-9 replaced compound M1-8, and the product obtained after purification was organic compound M12 in 27% yield, MS (ASAP) =789.
Example 13
Organic compoundIs synthesized by (a)
The synthetic route for the organic compound M13 is as follows:
the specific synthetic procedure for the organic compound M13 is as follows:
synthesis of intermediate M13-2:
The synthesis method is the same as or similar to that of the compound M5-3, except that: compound M13-1 replaces compound M5-2 in 68% yield.
Synthesis of intermediate M13-3:
The same or similar synthesis method as that of the compound M5-4 is different in that: compound M13-2 was substituted for compound M5-3 in 74% yield.
Synthesis of intermediate M13-4:
under the nitrogen environment, adding (8.3 g,40 mmol) compound M13-3 and 80mL anhydrous tetrahydrofuran into a 250mL three-port bottle, cooling to-78 ℃, slowly dropwise adding 45mmol of n-butyllithium solution, stirring at the maintained temperature for reaction for 2 hours, adding 50mmol of trimethyl borate at one time, slowly heating to room temperature, and continuously stirring for reaction for 4 hours; after the reaction is finished, adding water to quench the reaction, and removing most of the solvent by rotary evaporation; the obtained crude product is extracted by methylene dichloride and washed by water for three times, an organic phase is collected and the solvent is removed by rotary evaporation, the obtained product is added with 60mL of methylene dichloride for dissolution and then is transferred to a 250mL three-mouth bottle, 100mmol of hydrogen peroxide solution is slowly added in an ice bath, and the reaction is stirred for 2 hours at room temperature after the addition is finished; slowly dropwise adding 10mL of hydrochloric acid, and stirring for reaction for 1 hour; after the reaction, water is added to quench the reaction, the reaction solution is neutralized by using sodium bisulphite aqueous solution, dichloromethane is used for extraction, water is used for three times, and the organic phase is collected for column chromatography purification, and the yield is 65%.
Synthesis of intermediate M13-5:
The synthesis method is the same as or similar to that of the compound M5-3, except that: compounds M6-3 and M13-4 replaced compounds M5-1 and M5-2, respectively, in 52% yield.
Synthesis of organic compound M13:
The same or similar to the synthesis of compound M1, except that: compound M13-5 replaced compound M1-8, and the product obtained after purification was organic compound M13 in 24% yield, MS (ASAP) =832.
Example 14
Organic compoundIs synthesized by (a)
The synthetic route for the organic compound M14 is as follows:
The specific synthetic procedure for the organic compound M14 is as follows:
synthesis of intermediate M14-1:
The synthesis method is the same as or similar to that of the compound M8-3, except that: compound M11-5 replaced compound M8-2 in 78% yield.
Synthesis of intermediate M14-2:
the synthesis method is the same as or similar to that of the compound M11-7, except that: compound M14-1 was substituted for compound M11-6 in 82% yield.
Synthesis of intermediate M14-3:
the synthesis method is the same as or similar to that of the compound M5-3, except that: compounds M10-3 and M14-2 replaced compounds M5-1 and M5-2, respectively, in 57% yield.
Synthesis of organic compound M14:
The same or similar synthetic method as the compound M8, except that: compound M14-3 replaced compound M8-9, and the product obtained after purification was organic compound M14 in 26% yield, MS (ASAP) =715.
Example 15
Organic compoundIs synthesized by (a)
The synthetic route for the organic compound M15 is as follows:
the specific synthetic procedure for the organic compound M15 is as follows:
Synthesis of intermediate M15-2:
The same or similar synthesis method as that of the compound M1-3, except that: compound M15-1 was substituted for compound M1-2 in 72% yield.
Synthesis of intermediate M15-3:
the synthesis method is the same as or similar to that of the compound M2-5, except that: compound M15-2 replaces compound M2-3.
Synthesis of intermediate M15-4:
The same or similar synthesis method as the compounds M1-6, except that: compound M15-3 was substituted for compound M1-5 in 56% two-step yield.
Synthesis of intermediate M15-5:
the synthesis method is the same as or similar to that of the compound M11-7, except that: compound M15-4 replaced compound M11-6 in 80% yield.
Synthesis of intermediate M15-8:
Under nitrogen atmosphere, adding (14.4 g,100 mmol) compound M15-6, (20.5 g,100 mmol) compound M15-7, (65.2 g,200 mmol) cesium carbonate and 150mL dimethylformamide into a 500mL three-necked flask, and adding reflux reaction for 12 hours; after the reaction was completed, the reaction solution was cooled to room temperature, most of the solvent was removed by rotary evaporation, and the obtained crude product was extracted with methylene chloride and washed three times with water, and the organic phase was collected for column chromatography purification in a yield of 64%.
Synthesis of intermediate M15-9:
the synthesis method is the same as or similar to that of the compound M15-8, except that: compounds M15-5 and M15-8 replaced compounds M15-6 and M15-7, respectively, in 69% yield.
Synthesis of organic compound M15:
The same or similar to the synthesis of compound M1, except that: compound M15-9 replaced compound M1-8, and the product obtained after purification was organic compound M15 in 36% yield, MS (ASAP) =532.
Example 16
Organic compoundIs synthesized by (a)
The synthetic route for the organic compound M16 is as follows:
the specific synthetic procedure for the organic compound M16 is as follows:
Synthesis of intermediate M16-2:
The same or similar synthesis method as that of the compound M1-3, except that: compound M16-1 replaces compound M1-2 in a two-step yield of 63%.
Synthesis of intermediate M16-3:
The synthesis method is the same as or similar to that of the compound M3-5, except that: compound M16-2 replaced compound M3-4 in 65% yield.
Synthesis of intermediate M16-5:
The synthesis method is the same as or similar to that of the compound M3-7, except that: compounds M16-3 and M16-4 replaced compounds M3-5 and M3-6, respectively, in 84% yield.
Synthesis of intermediate M16-6:
the synthesis method is the same as or similar to that of the compound M11-7, except that: compound M16-5 replaces compound M11-6 in 75% yield.
Synthesis of intermediate M16-9:
the synthesis method is the same as or similar to that of the compound M15-8, except that: compounds M16-7 and M16-8 replaced compounds M15-6 and M15-7, respectively, in 73% yield.
Synthesis of intermediate M16-10:
The synthesis method is the same as or similar to that of the compound M15-8, except that: compounds M16-6 and M16-9 replaced compounds M15-6 and M15-7, respectively, in 70% yield.
Synthesis of organic compound M16:
The same or similar to the synthesis of compound M1, except that: compound M16-10 replaced compound M1-8, and the product obtained after purification was organic compound M16 in 34% yield, MS (ASAP) =623.
Example 17
Organic compoundIs synthesized by (a)
The synthetic route for the organic compound M17 is as follows:
The specific synthetic procedure for the organic compound M17 is as follows:
synthesis of intermediate M17-2:
the synthesis method is the same as or similar to that of the compound M5-3, except that: compounds M4-6 and M17-1 replaced compounds M5-1 and M5-2, respectively, in 63% yield.
Synthesis of intermediate M17-3:
The synthesis method is the same as or similar to that of the compound M5-3, except that: compounds M7-4 and M17-2 replaced compounds M5-1 and M5-2, respectively, in 53% yield.
Synthesis of organic compound M17:
the same or similar to the synthesis of compound M1, except that: compound M17-3 replaced compound M1-8, and the product obtained after purification was organic compound M17 in 36% yield, MS (ASAP) =526.
Example 18
Organic compoundIs synthesized by (a)
The synthetic route for the organic compound M18 is as follows:
the specific synthetic procedure for the organic compound M18 is as follows:
Synthesis of intermediate M18-2:
The synthesis method is the same as or similar to that of the compound M5-3, except that: compounds M6-5 and M18-1 replaced compounds M5-1 and M5-2, respectively, in 60% yield.
Synthesis of intermediate M18-3:
The same or similar synthesis method as that of the compound M5-4 is different in that: compound M18-2 was substituted for compound M5-3 in 78% yield.
Synthesis of intermediate M18-4:
The synthesis method is the same as or similar to that of the compound M11-7, except that: compound M18-3 replaced compound M11-6 in 72% yield.
Synthesis of intermediate M18-6:
the synthesis method is the same as or similar to that of the compound M15-8, except that: compound M18-5 replaces compound M15-6 in 68% yield.
Synthesis of intermediate M18-7:
The synthesis method is the same as or similar to that of the compound M15-8, except that: compounds M18-4 and M18-6 replaced compounds M15-6 and M15-7, respectively, in 75% yield.
Synthesis of organic compound M18:
The same or similar to the synthesis of compound M1, except that: compound M18-7 replaced compound M1-8, and the product obtained after purification was organic compound M18 in 32% yield, MS (ASAP) =579.
Exemplary steps for fabricating the light emitting element provided by the present invention are shown in the following exemplary embodiment 19.
Example 19
The light-emitting element provided in this embodiment includes an anode layer, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode layer sequentially formed on a substrate. Wherein, ITO is used as anode material, HIM is used as hole injection layer material, HTM is used as hole transport layer material, host is used as main material of luminescent layer, ET1 is used as electron transport layer material, liQ and Al are used as cathode materials. The preparation method comprises the following specific steps:
a. Cleaning an ITO anode: providing an ITO conductive glass substrate, cleaning the substrate by adopting one or more of cleaning agents such as deionized water, acetone, isopropanol, chloroform, acetone or isopropanol, and then performing ultraviolet ozone treatment;
b. Forming an organic functional layer: a hole injection layer with a thickness of 40nm, a hole transport layer with a thickness of 100nm, a light-emitting layer with a thickness of 50nm (mass ratio of host material to guest material in the light-emitting layer: 97:3) and an electron transport layer with a thickness of 25nm were formed in this order on the anode by thermal evaporation under high vacuum (1×10 -6 mbar);
c. Forming a cathode layer: liQ with a thickness of 1nm and Al with a thickness of 150nm are formed on the electron transport layer by thermal evaporation under high vacuum (1X 10 -6 mbar);
g. And (3) packaging: the device was encapsulated with an ultraviolet curable resin in a nitrogen glove box.
Specifically, in the present embodiment, the light-emitting elements 1 to 18, and the comparative element 1 are obtained through the above steps. Wherein the guest materials in the light-emitting layers of the light-emitting elements 1 to 18 are the organic compounds M1 to M18, respectively, and the guest materials in the light-emitting layers of the comparative element 1 are the comparative compounds 1, respectively (see patent CN111647010 a).
Specifically, HIM, HTM, ET, liQ, host, comparative compound 1 (Ref-1) are commercially available or obtained by known synthetic methods, and the chemical structural formula of the above compounds is as follows:
In this example, the current-voltage (J-V) characteristics of the light emitting elements 1 to 18 and the comparative element 1 were tested, and the relative values of the External Quantum Efficiency (EQE) of each light emitting element and the comparative element 1 and the relative values of the time (lt90@1000nits) taken for each light emitting element and the comparative element 1 to decrease to 90% of the initial luminance at the same initial luminance (1000 nits) were obtained under the same test conditions, and the specific results are shown in table 1.
Table 1: performance data of light emitting element 1 to light emitting element 18 and comparative element 1
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As can be seen from table 1, by introducing a cycloalkyl structure into the molecule, the hole transport property and resonance property of the organic compound molecule are enhanced, the interval between the molecules is increased, luminescence quenching caused by pi-pi stacking between the molecules is prevented, the luminescence efficiency of the light emitting element is effectively improved, and the lifetime of the light emitting element is prolonged.
According to the light-emitting element disclosed by the embodiment of the invention, the organic compound has the cyclopentyl structure, so that the hole transmission performance and the resonance performance of the organic compound are enhanced, and meanwhile, the intermolecular distance is effectively increased, so that exciton quenching caused by intermolecular accumulation is inhibited, the light-emitting efficiency of the light-emitting element is improved, and the service life of the light-emitting element is prolonged.
The embodiment of the invention also discloses a display panel which comprises any one of the light-emitting elements.
In some embodiments, the display panel further includes an array substrate at a side of the light emitting element, and an encapsulation layer at a side of the light emitting element away from the array substrate and covering the light emitting element. The display panel further comprises a polaroid layer positioned on one side of the packaging layer far away from the light-emitting element, and a cover plate layer positioned on one side of the polaroid layer far away from the light-emitting element. The polarizer layer can be replaced by a color film layer, and the color film layer can comprise a plurality of color resistors and black matrixes positioned on two sides of the color resistors.
According to the display panel disclosed by the embodiment of the invention, the organic compound with the structure shown in the general formula (1) is used in the light-emitting element, and the cyclopentyl structure of the organic compound enhances the hole transmission performance and resonance performance of the organic compound, and meanwhile, the intermolecular distance is effectively increased, so that exciton quenching caused by intermolecular accumulation is inhibited, the light-emitting efficiency of the light-emitting element is improved, and the service life of the light-emitting element is prolonged.
The embodiment of the invention discloses an organic compound, a light-emitting element and a display panel, wherein the organic compound has a structure shown as a general formula (1): The organic compound with the structure shown in the general formula (1) has a cyclopentyl structure, so that the hole transmission performance and resonance performance of the organic compound are enhanced, and meanwhile, the intermolecular distance is effectively increased, thus the exciton quenching caused by intermolecular accumulation is inhibited, the luminous efficiency of a luminous element is improved, and the service life of the luminous element is prolonged.
The organic compound, the light-emitting element and the display panel provided by the embodiments of the present invention are described in detail, and specific examples are applied to illustrate the principles and embodiments of the present invention, and the description of the above examples is only for helping to understand the method and core ideas of the present invention; meanwhile, as those skilled in the art will have variations in the specific embodiments and application scope in light of the ideas of the present invention, the present description should not be construed as limiting the present invention.

Claims (10)

1. An organic compound, characterized in that the organic compound has a structure represented by the general formula (1):
Wherein Z is selected from CR 1R2、NR3, O or S;
X, Y are each independently selected from O or NR 4;
Each occurrence of R 1、R2、R3、R4 is independently selected from: substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 5 to 30 carbon atoms, R 1 and R 2 are cyclic or acyclic;
Ar 1 is selected from: H. d, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aromatic group of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic group of 5 to 30 carbon atoms;
Ar 2 is selected from: a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms.
2. The organic compound according to claim 1, wherein the organic compound has a structure represented by any one of the general formulae (2-1) to (2-6):
3. The organic compound according to claim 1, wherein at least one of X and Y is selected from NR 4.
4. An organic compound according to claim 3, wherein R 4 is independently selected for each occurrence from the group consisting of: a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 carbon atoms.
5. The organic compound according to claim 1, wherein R 1、R2、R3 is independently selected for each occurrence from the group consisting of: substituted or unsubstituted alkyl having 1 to 12 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 5 to 20 carbon atoms, R 1 and R 2 are cyclic or acyclic.
6. The organic compound according to any one of claims 1 to 5, wherein Ar 1 is selected from: H. d, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 carbon atoms;
ar 2 is selected from: a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 carbon atoms.
7. The organic compound according to claim 1, characterized in that the organic compound is selected from the following compounds:
8. a light-emitting element, comprising:
a pair of electrodes including a first electrode and a second electrode;
an organic functional layer located between the first electrode and the second electrode;
Wherein the material of the organic functional layer comprises at least one organic compound according to any one of claims 1 to 7.
9. The light-emitting element according to claim 8, wherein the organic functional layer comprises a light-emitting layer comprising at least one organic compound according to any one of claims 1 to 7.
10. A display panel comprising the light-emitting element according to any one of claims 8 to 9.
CN202410199970.2A 2024-02-22 2024-02-22 Organic compound, light-emitting element, and display panel Pending CN118084953A (en)

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