CN117865944A

CN117865944A - Organic compound, light-emitting element, and display panel

Info

Publication number: CN117865944A
Application number: CN202311816349.8A
Authority: CN
Inventors: 邹源佐; 周世豪; 宋鑫龙; 何锐锋; 宋晶尧
Original assignee: Shenzhen China Star Optoelectronics Semiconductor Display Technology Co Ltd
Current assignee: Shenzhen China Star Optoelectronics Semiconductor Display Technology Co Ltd
Priority date: 2023-12-26
Filing date: 2023-12-26
Publication date: 2024-04-12

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):the invention has the general formula (1), and the carbazolyl and the arylamine in the organic compound are connected on the same side of naphthobenzofuran or naphthobenzothiophene to obtain higher molecular torsion degree, so that better film forming effect and more stable hole transmission performance are easily obtained when the organic compound is applied to a light-emitting element, and meanwhile, the carbazolyl is connected with the phenyl at the 9-position of the carbazolyl to be connected with the naphthobenzoThe furan or naphthothiophene ensures that the electron cloud of the organic compound is distributed more uniformly, and can obtain more balanced hole transmission capability and more proper electron blocking capability when being applied to the light-emitting element, thereby improving the light-emitting efficiency of the light-emitting element and prolonging the service life of the light-emitting element.

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 and prolong the service life of the organic electroluminescent element, a luminescent auxiliary material is used in an organic functional layer of the organic electroluminescent element, and the conventional luminescent auxiliary material still has the defects in the performances of carrier transmission, charge balance adjustment and the like, so that the luminous efficiency and the service life of the organic electroluminescent element still have room for improvement.

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 solve the technical problems that the light-emitting efficiency and the service life of an organic electroluminescent element are difficult to improve due to the defects of the current light-emitting auxiliary material in the performances of carrier transmission, charge balance adjustment and the like.

The present invention provides an organic compound having a structure represented by the general formula (1):

wherein X is selected from O or S;

Ar ¹ selected from naphthyl;

Ar ² 、Ar ³ each independently selected from substituted or unsubstituted aromatic groups having 6 to 60 ring atoms;

R ¹ 、R ² each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms;

L ¹ Selected from substituted or unsubstituted phenylene;

L ² selected from single bond, substituted or unsubstituted phenylene;

m is selected from any integer from 1 to 3, and n is selected from any integer from 0 to 3;

a is selected from any integer from 0 to 2, and b is selected from any integer from 0 to 6.

Preferably, the organic compound has a structure as shown in any one of the general formulae (1-1) to (1-3):

preferably Ar ² 、Ar ³ Each independently selected from the following groups:

wherein R is ₃ 、R ₄ 、R ₅ Each occurrence is independently selected from deuterium, a substituted or unsubstituted straight chain alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted branched alkyl or cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms; or, adjacent R ₄ 、R ₅ The connection being formed with 3 to 10 carbonsCycloalkyl of atoms;

c is selected from any integer from 0 to 7;

* Representing the ligation site.

Preferably, R ₃ 、R ₄ 、R ₅ Each occurrence is independently selected from deuterium, a substituted or unsubstituted straight chain alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted branched alkyl or cycloalkyl group having 3 to 10 carbon atoms, and a substituted or unsubstituted aromatic group having 6 to 18 ring atoms.

Preferably, R ₄ 、R ₅ Selected from methyl, ar ² 、Ar ³ Each independently selected from the following groups:

preferably, R ¹ 、R ² Each independently selected from deuterium or methyl.

Preferably, the organic compound is selected from the following compounds:

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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 includes a light emitting layer, a hole transporting layer between the light emitting layer and the first electrode, a light emitting auxiliary layer between the hole transporting layer and the light emitting layer, a hole injecting layer between the hole transporting layer and the first electrode, an electron transporting layer between the light emitting layer and the second electrode, and an electron injecting layer between the electron transporting layer and the second electrode;

wherein the light-emitting auxiliary layer comprises at least one organic compound as described above.

The present invention also provides a display panel comprising a light emitting element as claimed in any one of the above.

According to the invention, through using the organic compound with the structure shown in the general formula (1), the carbazolyl and the arylamine in the organic compound are connected to the same side of the naphthobenzofuran or the naphthobenzothiophene, so that higher molecular torsion degree is obtained, better film forming effect and more stable hole transmission performance are easily obtained when the organic compound is applied to a light-emitting element, and meanwhile, the 9-position of the carbazolyl is connected with the phenyl so as to be connected to the naphthobenzofuran or the naphthobenzothiophene, so that the electron cloud distribution of the organic compound is more uniform, more balanced hole transmission capability and more suitable electron blocking capability can be obtained when the organic compound is applied to the light-emitting element, the light-emitting efficiency of the light-emitting element is improved, and the service life of the light-emitting 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. 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. Phrases containing this term, e.g., "C _1-9 Alkyl "means an alkyl group containing 1 to 9 carbon atoms, and each occurrence may be, independently of the other, 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 An alkyl group. 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-hexyloctyl, 3, 7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-hexyldodecyl, n-dodecyldodecyl, n-tridecyl A group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-eicosyl group, 2-ethyleicosyl group, 2-butyleicosyl group, 2-hexyleicosyl group, 2-octyleicosyl group, n-heneicosyl group, n-docosyl group, n-tricosyl group, n-tetracosyl group, n-pentacosyl group, n-hexacosyl group, n-heptacosyl group, n-octacosyl group, n-nonacosyl group, n-triacontyl group, and the like.

In the present invention, the abbreviations of the substituents correspond to: n-n, sec-sec, i-iso, t-tert, o-o, m-m, p-pair, memethyl, et ethyl, pr propyl, bu butyl, am pentyl, hx hexyl, cy cyclohexyl.

In the present invention, "amine group" means a derivative of an amine having the 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, hydroxyl means-OH, carboxyl means-COOH, carbonyl means-C (=O) -, and amino means-NH, unless otherwise specified ₂ Formyl means-C (=o) H, haloformyl means-C (=o) Z (wherein Z represents halogen), carbamoyl means-C (=o) NH ₂ Isocyanate groups refer to-NCO and isothiocyanate groups refer to-NCS.

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 ₂ CH ₃ 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, 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; for example->Representation->Can be combined 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, "two adjacent R' s ₁ Or R is ₃ Or R is ₅ Mutually cyclic "means by two adjacent R ₁ Or R is ₃ Or R is ₅ And a ring system formed by interconnecting, wherein the ring system can be selected from aliphatic hydrocarbon ring, aliphatic heterocycle, aromatic hydrocarbon ring or aromatic heterocycle. Preferably, can be formed into

At present, due to the defects of the luminescent auxiliary material in the performances of carrier transmission, charge balance adjustment and the like, the problem that the luminous efficiency and the service life of the organic electroluminescent element still have room for improvement exists.

The embodiment of the invention provides an organic compound, which has a structure shown as a general formula (1):

Wherein X is selected from O or S;

Ar ¹ selected from naphthyl;

L ¹ selected from substituted or unsubstituted phenylene;

L ² selected from single bond, substituted or unsubstituted phenylene;

According to the invention, the carbazolyl and the arylamine in the organic compound are connected to the same side of the naphthobenzofuran or the naphthobenzothiophene through the organic compound with the structure shown in the general formula (1), so that higher molecular torsion degree is obtained, better film forming effect and more stable hole transmission performance are easily obtained when the organic compound is applied to a light-emitting element, and meanwhile, the 9-position of the carbazolyl is connected with the phenyl so as to be connected to the naphthobenzofuran or the naphthobenzothiophene, so that the electron cloud distribution of the organic compound is more uniform, more balanced hole transmission capability and more suitable electron blocking capability can be obtained when the organic compound is applied to the light-emitting element, the light-emitting efficiency of the light-emitting element is improved, and the service life of the light-emitting element is prolonged.

In some embodiments, the organic compound has a structure as shown in any one of formulas (1-1) to (1-3):

in some embodiments, ar ² 、Ar ³ Each independently selected from substituted or unsubstituted aromatic groups having 6 to 40 ring atoms.

In some embodiments, ar ² 、Ar ³ Each independently selected from substituted or unsubstituted aromatic groups having 6 to 30 ring atoms.

In some embodiments, ar ² 、Ar ³ Each independently selected from substituted or unsubstituted aromatic groups having 6 to 20 ring atoms.

In some embodiments, ar ² 、Ar ³ Each independently selected from substituted or unsubstituted aromatic groups having 6 to 16 ring atoms.

In some embodiments, ar ² 、Ar ³ Each independently selected from substituted or unsubstituted aromatic groups having 6 to 13 ring atoms.

In some embodiments, ar ² 、Ar ³ Each independently selected from substituted or unsubstituted aromatic groups having 6 to 12 ring atoms.

In some embodiments, ar ² 、Ar ³ Each independently selected from substituted or unsubstituted aromatic groups having 6 to 10 ring atoms.

In some embodiments, ar ² 、Ar ³ Each independently selected from the following groups:

wherein R is ₃ 、R ₄ 、R ₅ Each occurrence is independently selected from deuterium, a substituted or unsubstituted straight chain alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted branched alkyl or cycloalkyl group having 3 to 20 carbon atoms, and a substituted or unsubstituted aromatic group having 6 to 60 ring atoms. R is R ₄ 、R ₅ Can be linked to each other to form a ring, or R ₄ 、R ₅ May not be interconnected in a ring.

c is selected from any integer from 0 to 7.

* Representing the ligation site.

In some embodiments, R ₃ 、R ₄ 、R ₅ Each occurrence is independently selected from deuterium, a substituted or unsubstituted straight chain alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted branched alkyl or cycloalkyl group having 3 to 10 carbon atoms, and a substituted or unsubstituted aromatic group having 6 to 30 ring atoms.

In some embodiments, R ₃ 、R ₄ 、R ₅ Each occurrence is independently selected from deuterium, a substituted or unsubstituted straight chain alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted branched alkyl or cycloalkyl group having 3 to 10 carbon atoms, and a substituted or unsubstituted aromatic group having 6 to 18 ring atoms.

In some embodiments, R ₃ 、R ₄ 、R ₅ Each occurrence is independently selected from deuterium, a substituted or unsubstituted straight chain alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted branched alkyl or cycloalkyl group having 3 to 10 carbon atoms, and a substituted or unsubstituted aromatic group having 6 to 10 ring atoms.

In some embodiments, R ₃ Each occurrence is independently selected from deuterium, methyl, ethyl, isopropyl, n-butyl, t-butyl, cyclohexyl, adamantyl, phenyl, naphthyl, biphenyl, triphenylene. Wherein, the biphenyl can be represented by the following structure: d represents any one integer from 0 to 3.

In some embodiments, R ₄ 、R ₅ Each occurrence is independently selected from methyl, ethyl, isopropyl, n-butyl, t-butyl.

In some embodiments, adjacent R' s ₄ 、R ₅ May be linked to each other to form a cycloalkyl group having 3 to 10 carbon atoms, for example: cyclopentyl, cyclohexyl, adamantyl, and the like.

In some embodiments, R ₄ 、R ₅ Are all methyl, ar ² 、Ar ³ Each independently selected from the following groups:

in some embodiments, R ¹ 、R ² Each independently selected from deuterium, a substituted or unsubstituted straight chain alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted branched alkyl or cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 ring atoms substituted or unsubstituted, and a heteroaryl group having 6 to 14 ring atoms substituted or unsubstituted.

In some embodiments, R ¹ 、R ² Each independently selected from deuterium, substituted or unsubstituted straight chain alkyl groups having 1 to 3 carbon atoms, substituted or unsubstituted tertiary butyl groups, substituted or unsubstituted cycloalkyl groups having 5 to 10 carbon atoms, substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted dibenzofuranyl groups.

In some embodiments, c is selected from any integer from 0 to 7, i.e., c may be selected from any integer from 0, 1, 2, 3, 4, 5, 6, 7.

In some embodiments, R ¹ 、R ² Are each independently selected from deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstitutedSubstituted tert-butyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl.

In some embodiments, the substituted methyl, substituted ethyl, substituted isopropyl, substituted tert-butyl, substituted cyclopentyl, substituted cyclohexyl, substituted adamantyl satisfy the following conditions: at least one H in the group is replaced by deuterium.

In some embodiments, L ¹ Each occurrence is independently selected from the following groups:

in some embodiments, L ² Each occurrence is independently selected from a single bond or the following groups:

in some embodiments, m is selected from any integer from 1 to 3, and m may be any integer from 1, 2, 3.

In some embodiments, n is selected from any integer from 0 to 3, and n may be any integer from 0, 1, 2, 3.

In some embodiments, a is selected from any integer from 0 to 2, and a may be any integer from 0, 1, 2.

In some embodiments, b is selected from any integer from 0 to 6, and b may be any integer from 0, 1, 2, 3, 4, 5, 6.

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 carbazolyl and the arylamine are connected to the same side of the naphthobenzofuran or the naphthobenzothiophene, so that higher molecular torsion degree is obtained, better film forming effect and more stable hole transmission performance are easily obtained when the organic compound is applied to a light-emitting element, meanwhile, the 9-position of the carbazolyl is connected with the phenyl so as to be connected to the naphthobenzofuran or the naphthobenzothiophene, so that the electron cloud of the organic compound is distributed more uniformly, more uniform hole transmission capability and more suitable electron blocking capability can be obtained when the organic compound is applied to the light-emitting element, the light-emitting efficiency of the light-emitting element is improved, and the service life of the light-emitting 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. Detailed descriptions of various organic functional materials included in the organic functional layer 103 are provided in WO2010135519A1, US20090134784A1 and WO2011110277A1, the entire contents of which are hereby incorporated by reference.

In some embodiments, the emissive guest material is selected from the group consisting of singlet emitters (fluorescent emitters), triplet emitters (phosphorescent emitters), and TADF materials.

In some embodiments, the luminescent guest material is selected from inorganic quantum dots.

The organic compound can be used as a light-emitting auxiliary material.

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 107; preferably, the organic functional layer 103 includes a hole injection layer 104, a hole transport layer 105, a light emitting auxiliary layer 106, a light emitting layer 107, an electron injection layer 109, an electron transport layer 108, or a hole blocking layer.

In some embodiments, the hole transport layer 105 is located between the light emitting layer 107 and the first electrode 101, the light emitting auxiliary layer 106 is located between the hole transport layer 105 and the light emitting layer 107, the hole injection layer 104 is located between the hole transport layer 105 and the first electrode 101, the electron transport layer 108 is located between the light emitting layer 107 and the second electrode 102, and the electron injection layer 109 is located between the electron transport layer 108 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 107 may include a host material including a fused aromatic derivative or a heteroaromatic compound, and a guest material that is one or more of the light emitting guest materials described above.

The light emitting element has a light emitting wavelength of 300 to 1000 nm; further, the light emitting element has a light emitting wavelength of 350 to 900 nm; 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 107 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 energy levels of the work function of the anode and the light emitting material in the light emitting layer, or HOMO (highest occupied molecular orbital ) or valence band energy level as the p-type semiconductor material in the hole injection layer or 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, which may 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 and BaF ₂ At least one of/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 107, 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 107, 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 108 is configured to transport electrons, and the electron transport layer 108 includes an electron transport material that receives electrons injected from the negative electrode and transfers the electrons to the light emitting layer 107. 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 109 is used to inject electrons, and the electron injection layer 109 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 107 or the light emitting material, and having a capability of preventing excitons generated by the light emitting layer 107 from moving to the hole injection layer, and also having an excellent capability of forming 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 110, and the first electrode 101, the hole injection layer 104, the hole transport layer 105, the electron blocking layer 106, the light emitting layer 107, the electron transport layer 108, the electron injection layer 109, and the second electrode 102 are sequentially stacked on the substrate 110. The substrate 110 may be a transparent substrate or an opaque substrate, and when the substrate 110 is a transparent substrate, a transparent light emitting element may be fabricated; the substrate 110 may be a rigid substrate or a flexible substrate having elasticity, and the material of the substrate 110 may include, but is not limited to, plastic, polymer, metal, semiconductor wafer, glass, or the like. Preferably, the substrate 110 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 110 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 110 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 delta d (dispersion force) of the dispersing agent is 17.0-23.2 MPa ^1/2 Preferably in the range of 18.5 to 21.0MPa ^1/2 Is defined by the range of (2); δp (polar force) is 0.2-12.5 MPa ^1/2 Is preferably in the range of 2.0 to 6.0MPa ^1/2 Is defined by the range of (2); δh (hydrogen bond force) is 0.9-14.2 MPa ^1/2 Is preferably in the range of 2.0 to 6.0MPa ^1/2 Is not limited in terms of the range of (a).

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 24.

Example 1

Organic Compound P1Is synthesized by (a)

The synthetic route for the organic compound P1 is as follows:

/>

the specific synthetic procedure for organic compound P1 is as follows:

synthesis of intermediate P1-3:

p1-1 (90 mmol,29.8 g) and P1-2 (90 mmol,25.8 g) were weighed into a clean three-neck flask, and tetrakis triphenylphosphine palladium (2%, 2.1 g), potassium carbonate (270 mmol,37.3 g), 1, 4-dioxane (400 mL) and deionized water (100 mL) were added, replaced with nitrogen three times, and heated to 80℃for reflux reaction for 12h; quenching with water after natural cooling, removing the solvent by rotary evaporation, extracting with dichloromethane three times, washing the separated liquid with water, drying with anhydrous sodium sulfate, and rotary drying, wherein the column chromatography is performed to obtain an intermediate P1-3, the yield is 77.8%, and the result of an atmospheric pressure solid phase analysis probe mass spectrum (ASAP-MS) of the intermediate P1-3 is as follows: MS (ASAP) =494.

Synthesis of organic compound P1:

p1-3 (70 mmol,34.6 g) and P1-4 (80 mmol,13.5 g) were weighed into a clean three-necked flask and Pd was added ₂ (dba) ₃ (1%, 0.6 g), X-Phos (1.4 mmol,0.7 g), sodium t-butoxide (140 mmol,13.5 g), and anhydrous toluene (400 mL), nitrogen was replaced three times, and the temperature was raised to 90℃and the reaction was refluxed for 12 hours; after natural cooling, washing the separated liquid, drying the organic phase, spin-drying, and performing column chromatography to obtain the organic compound P1, wherein the yield is 84.1%, and MS (ASAP) =627.

Example 2

Organic Compound P2Is synthesized by (a)

The synthetic route for the organic compound P2 is as follows:

the specific synthetic procedure for organic compound P2 is as follows:

synthesis of organic compound P2:

referring to the synthetic method of the organic compound P1 in example 1, P1-4 was replaced with P2-1 to obtain the organic compound P2 in a yield of 70.4%, MS (ASAP) =703.

Example 3

Organic Compound P3Is synthesized by (a)

The synthetic route for organic compound P3 is as follows:

the specific synthetic procedure for organic compound P3 is as follows:

synthesis of organic compound P3:

referring to the synthetic method of the organic compound P1 in example 1, P1-4 was replaced with P3-1 to obtain the organic compound P3 in a yield of 74.2%, MS (ASAP) =779.

Example 4

Organic Compound P4 Is synthesized by (a)

The synthetic route for organic compound P4 is as follows:

the specific synthetic procedure for organic compound P4 is as follows:

synthesis of organic compound P4:

referring to the synthetic method of the organic compound P1 in example 1, P1-4 was replaced with P4-1, to obtain the organic compound P4 in a yield of 62.2%, MS (ASAP) =753.

Example 5

Organic Compound P5Is synthesized by (a)

The synthetic route for organic compound P5 is as follows:

the specific synthetic procedure for organic compound P5 is as follows:

synthesis of organic compound P5:

referring to the synthetic method of the organic compound P1 in example 1, P1-4 was replaced with P5-1 to obtain the organic compound P5 in a yield of 70.1%, MS (ASAP) =743.

Example 6

Organic Compound P6Is synthesized by (a)

The synthetic route for organic compound P6 is as follows:

the specific synthetic procedure for organic compound P6 is as follows:

synthesis of intermediate P6-2:

referring to the synthesis of intermediate P1-3 of example 1, substitution of P1-2 with P6-1 provided intermediate P6-2 in 76.9% yield, MS (ASAP) =494.

Synthesis of organic compound P6:

referring to the synthesis method of the organic compound P1 in example 1, substitution of P1-3 with P6-2 and P1-4 with P6-3 gave the organic compound P6 in a yield of 78.0%, MS (ASAP) =703.

Example 7

Organic Compound P7Is synthesized by (a)

The synthetic route for organic compound P7 is as follows:

the specific synthetic procedure for organic compound P7 is as follows:

synthesis of organic compound P7:

referring to the synthesis of organic compound P6 in example 6, P6-3 was replaced with P7-1 to give organic compound P7 in a yield of 70.4%, MS (ASAP) =859.

Example 8

Organic Compound P8Is synthesized by (a)

The synthetic route for organic compound P8 is as follows:

the specific synthetic procedure for organic compound P8 is as follows:

synthesis of intermediate P8-2:

referring to the synthesis of intermediate P1-3 of example 1, substitution of P1-2 with P8-1 afforded intermediate P8-2 in 82.8% yield, MS (ASAP) =494.

Synthesis of organic compound P8:

referring to the synthetic method of the organic compound P1 in example 1, P1-3 was replaced with P8-2 to obtain the organic compound P8 in a yield of 76.9%, MS (ASAP) =627.

Example 9

Organic Compound P9Is synthesized by (a)

The synthetic route for organic compound P9 is as follows:

the specific synthetic procedure for organic compound P9 is as follows:

synthesis of organic compound P9:

referring to the synthesis method of organic compound P8 in example 8, P1-4 was replaced with P9-1 to obtain organic compound P9 in a yield of 56.0%, MS (ASAP) =779.

Example 10

Organic Compound P10Is synthesized by (a)

The synthetic route for organic compound P10 is as follows:

the specific synthetic procedure for organic compound P10 is as follows:

synthesis of organic compound P10: referring to the synthesis method of organic compound P8 in example 8, P1-4 was replaced with P10-1 to obtain organic compound P10 in a yield of 74.2%, MS (ASAP) =753.

Example 11

Organic Compound P11Is synthesized by (a)

The synthetic route for organic compound P11 is as follows:

the specific synthetic procedure for organic compound P11 is as follows:

synthesis of intermediate P11-2:

weigh P1-1 (80 mmol,26.5 g) and P11-1 (80 mmol,22.8 g) into a clean three-neck flask and add Pd ₂ (dba) ₃ (1%, 0.7 g), sodium t-butoxide (160 mmol,15.4 g) and anhydrous toluene (240 mL), replaced with nitrogen three times, injected with anaerobic tri-t-butylphosphine (1.6 mmol,0.3 g), and heated to 80 ℃ for reflux reaction for 6h; after natural cooling, the organic phase was dried and spin-dried, and column chromatography gave intermediate P11-2 in 69.5% yield, MS (ASAP) =536.

Synthesis of organic compound P11:

p11-2 (50 mmol,26.8 g) and P1-2 (50 mmol,14.4 g) were weighed into a clean three-neck flask, and tetrakis triphenylphosphine palladium (2%, 1.2 g), potassium carbonate (150 mmol,20.7 g), 1, 4-dioxane (300 mL) and deionized water (75 mL) were added, replaced with nitrogen three times, and heated to 90℃for reflux reaction for 12h; quenching with water after natural cooling, spin-evaporating to remove solvent, extracting with dichloromethane three times, washing with water, drying with anhydrous sodium sulfate, spin-drying, and column chromatography to obtain organic compound P11 with yield of 72.8%, MS (ASAP) =743.

Example 12

Organic Compound P12Is synthesized by (a)

The synthetic route for organic compound P12 is as follows:

the specific synthetic procedure for organic compound P12 is as follows:

synthesis of intermediate P12-1:

referring to the method for synthesizing intermediate P11-2 of example 11, substituting P11-1 with P2-1, intermediate P12-1 was obtained in a yield of 60.5%, MS (ASAP) =496.

Synthesis of organic compound P12:

referring to the synthesis method of organic compound P11 in example 11, substitution of P11-2 with P12-1 and P1-2 with P6-1 gave organic compound P12 in 77.3% yield, MS (ASAP) =703.

Example 13

Organic Compound P13Synthesis of->

The synthetic route for organic compound P13 is as follows:

the specific synthetic procedure for organic compound P13 is as follows:

synthesis of intermediate P13-2:

referring to the synthesis of intermediate P11-2 of example 11, substitution of P1-1 for P13-1 and P11-1 for P6-3 gave intermediate P13-2 in 80.6% yield, MS (ASAP) =496.

Synthesis of organic compound P13:

referring to the synthesis method of organic compound P11 in example 11, P11-2 was replaced with P13-2 to obtain organic compound P13 in a yield of 63.3%, MS (ASAP) =703.

Example 14

Organic Compound P14Is synthesized by (a)

The synthetic route for organic compound P14 is as follows:

The specific synthetic procedure for organic compound P14 is as follows:

synthesis of intermediate P14-2:

referring to the synthesis of intermediate P1-3 of example 1, substitution of P1-2 with P14-1 yielded intermediate P14-2 in 71.1% yield, MS (ASAP) =508.

Synthesis of organic compound P14:

referring to the synthesis of organic compound P1 in example 1, substitution of P1-3 with P14-2 and P1-4 with P6-3 gave organic compound P14 in 78.4% yield, MS (ASAP) =717.

Example 15

Organic Compound P15Is synthesized by (a)

The synthetic route for organic compound P15 is as follows:

the specific synthetic procedure for organic compound P15 is as follows:

synthesis of intermediate P15-2:

referring to the synthesis of intermediate P1-3 of example 1, substitution of P1-1 for P15-1 and P1-2 for P6-1 gave intermediate P15-2 in 77.8% yield, MS (ASAP) =508.

Synthesis of organic compound P15:

referring to the synthesis method of the organic compound P1 in example 1, substitution of P1-3 with P15-2 and P1-4 with P5-1 gave the organic compound P15 in a yield of 64.5% and MS (ASAP) =757.

Example 16

Organic Compound P16Is synthesized by (a)

The synthetic route for organic compound P16 is as follows:

the specific synthetic procedure for organic compound P16 is as follows:

Synthesis of intermediate P16-2:

referring to the synthesis of intermediate P1-3 of example 1, substitution of P1-1 for P16-1 and P1-2 for P6-1 gave intermediate P16-2 in 84.9% yield, MS (ASAP) =510.

Synthesis of organic compound P16:

referring to the synthesis method of the organic compound P1 in example 1, substitution of P1-3 with P16-2 and P1-4 with P6-3 gave the organic compound P16 in a yield of 78.6%, MS (ASAP) =719.

Example 17

Organic Compound P17Is synthesized by (a)

The synthetic route for organic compound P17 is as follows:

the specific synthetic procedure for organic compound P17 is as follows:

synthesis of intermediate P17-2:

referring to the synthesis of intermediate P1-3 of example 1, substitution of P1-1 with P17-1 yielded intermediate P17-2 in 60.0% yield, MS (ASAP) =494.

Synthesis of organic compound P17:

referring to the synthesis method of the organic compound P1 in example 1, substitution of P1-3 with P17-2 and P1-4 with P11-1 gave the organic compound P17 in a yield of 64.9% and MS (ASAP) =743.

Example 18

Organic Compound P18Is synthesized by (a)

The synthetic route for organic compound P18 is as follows:

the specific synthetic procedure for organic compound P18 is as follows:

synthesis of intermediate P18-2:

referring to the synthesis of intermediate P1-3 of example 1, substitution of P1-1 with P18-1 afforded intermediate P18-2 in 55.9% yield, MS (ASAP) =494.

Synthesis of organic compound P18:

referring to the synthesis method of the organic compound P1 in example 1, substitution of P1-3 with P18-2 and P1-4 with P3-1 gave the organic compound P18 in 59.4% yield, MS (ASAP) =779.

Example 19

Organic Compound P19Is synthesized by (a)

The synthetic route for organic compound P19 is as follows:

the specific synthetic procedure for organic compound P19 is as follows:

synthesis of intermediate P19-2:

referring to the synthesis of intermediate P1-3 of example 1, substitution of P1-1 with P19-1 afforded intermediate P19-2 in 57.8% yield, MS (ASAP) =494.

Synthesis of organic compound P19:

referring to the synthesis of organic compound P1 in example 1, substitution of P1-3 with P19-2 and P1-4 with P19-3 gave organic compound P19 in 57.1% yield, MS (ASAP) =717.

Example 20

Organic chemicalCompound P20Is synthesized by (a)

The synthetic route for organic compound P20 is as follows:

the specific synthetic procedure for organic compound P20 is as follows:

synthesis of intermediate P20-1:

referring to the synthesis of intermediate P1-3 of example 1, substitution of P1-1 for P17-1 and P1-2 for P6-1 gave intermediate P20-1 in 79.2% yield, MS (ASAP) =494.

Synthesis of organic compound P20:

referring to the synthesis method of the organic compound P1 in example 1, substitution of P1-3 with P20-1 and P1-4 with P20-2 gave the organic compound P20 in a yield of 75.9%, MS (ASAP) =753.

Example 21

Organic Compound P21Is synthesized by (a)

The synthetic route for organic compound P21 is as follows:

the specific synthetic procedure for organic compound P21 is as follows:

synthesis of intermediate P21-1:

referring to the synthesis of intermediate P1-3 of example 1, substitution of P1-2 with P6-1 afforded intermediate P21-1 in 78.9% yield, MS (ASAP) =494.

Synthesis of organic compound P21:

referring to the synthesis method of the organic compound P1 in example 1, substitution of P1-3 with P21-1 and P1-4 with P21-2 gave the organic compound P21 in 73.6% yield, MS (ASAP) =709.

Example 22

Organic Compound P22Is synthesized by (a)

The synthetic route for organic compound P22 is as follows:

the specific synthetic procedure for organic compound P22 is as follows:

synthesis of intermediate P22-2:

referring to the synthesis of intermediate P1-3 of example 1, substitution of P1-1 for P22-1 and P1-2 for P6-1 gave intermediate P22-2 in 79.2% yield, MS (ASAP) =502.

Synthesis of organic compound P22:

referring to the synthetic method of the organic compound P1 in example 1, P1-3 was replaced with P22-2 to obtain the organic compound P22 in a yield of 75.1%, MS (ASAP) =635.

Example 23

Organic Compound P23Synthesis of->

The synthetic route for organic compound P23 is as follows:

The specific synthetic procedure for organic compound P23 is as follows:

synthesis of intermediate P23-1:

referring to the synthesis of intermediate P1-3 of example 1, substitution of P1-1 for P19-1 and P1-2 for P6-1 gave intermediate P23-1 in 80.3% yield, MS (ASAP) =494.

Synthesis of organic compound P23:

referring to the synthesis method of the organic compound P1 in example 1, substitution of P1-3 with P23-1 and P1-4 with P23-2 gave the organic compound P23 in 73.3% yield, MS (ASAP) =739.

Example 24

Organic Compound P24Is synthesized by (a)

The synthetic route for organic compound P24 is as follows:

the specific synthetic procedure for organic compound P24 is as follows:

synthesis of organic compound P24:

referring to the synthesis method of the organic compound P1 in example 1, substitution of P1-3 with P23-1 and P1-4 with P24-1 gave the organic compound P24 in a yield of 70.0%, MS (ASAP) =761.

Exemplary fabrication steps of the light emitting element provided by the present invention are shown in the following exemplary embodiment 25.

Example 25

The light-emitting element provided in this embodiment includes an anode layer, a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an organic light-emitting layer, an electron transport layer, an electron injection layer, and a cathode layer sequentially formed on a substrate, and the specific preparation steps are as follows:

a. Cleaning an ITO anode: ultrasonic cleaning with deionized water, acetone and isopropanol for 15 minutes, and then treating in a plasma cleaner for 5 minutes to improve the work function of the electrode;

b. forming a hole injection layer: evaporating a hole injection material HATCN on the ITO anode in a vacuum evaporation mode to form a hole injection layer, wherein the thickness of the hole injection layer is 10nm;

c. forming a hole transport layer: evaporating a hole transport material HT on the hole injection layer in a vacuum evaporation mode to form a hole transport layer, wherein the thickness of the hole transport layer is 60nm;

d. forming a light emitting auxiliary layer: evaporating a light-emitting auxiliary material on the hole transport layer to form a light-emitting auxiliary layer, wherein the thickness of the light-emitting auxiliary layer is 10nm;

e. forming a light emitting layer: evaporating a light-emitting layer on the light-emitting auxiliary layer, wherein Host is used as a main material, dopant is used as a doping material, the mass ratio of Host to Dopant is 98:2, and the thickness of the light-emitting layer is 25nm;

f. forming an electron transport layer: evaporating electron transport materials ET and Liq (the mass ratio of the ET to the Liq is 5:5) on the organic light-emitting layer by a vacuum evaporation mode to form an electron transport layer, wherein the thickness of the electron transport layer is 30nm;

g. forming an electron injection layer: forming an electron injection layer on the electron transport layer by vacuum evaporation of an electron injection material Liq, wherein the thickness of the electron injection layer is 1nm;

h. forming a cathode layer: depositing Al on the electron injection layer by vacuum evaporation to obtain an Al cathode with the thickness of 100 nm;

i. 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 24, and the contrast elements 1 to 3 are obtained through the above steps. The light-emitting auxiliary materials used in the light-emitting elements 1 to 24 are organic compounds P1 to P24, and the light-emitting auxiliary materials used in the contrast elements 1 to 3 are Ref1, ref2, and Ref3, respectively.

Specifically, HATCN, HT, host, dopant, ET, liq, ref, ref2, ref3 and Ref4 are all commercially available or are synthesized from known materials by known synthetic methods, and the chemical structural formula of the above compound is as follows:

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in the present embodiment, the light emitting elements 1 to 24 are each configured toThe comparative elements 1 to 4 were subjected to a current-voltage (J-V) characteristic test, and each of the light-emitting elements and the comparative element was obtained at a current density of 10mA/cm ² The relative luminous efficiency, relative driving voltage, and time (relative lifetime) required for the luminance to drop to 95% of the initial luminance @1000nits are shown in table 2.

Table 1: performance data of light emitting elements 1 to 24 and comparison elements 1 to 4

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As can be seen from table 1, the light-emitting devices 1 to 24 obtained by using the organic compounds P1 to P24 as the light-emitting auxiliary materials in the light-emitting auxiliary layers according to the present invention have significantly improved light-emitting efficiency and lifetime compared to the comparative devices 1 to 4.

When the organic compounds P1 to P24 are used as the light-emitting auxiliary materials, compared with Ref1 or Ref4, the organic compounds P1 to P24 have better film-forming effect and more stable hole-transporting capability when forming the light-emitting auxiliary layer by vapor deposition, and are favorable for improving the light-emitting efficiency and service life of the light-emitting element, compared with the carbazole group, the diarylamine group and the connection site of the benzonaphthofuran which are arranged on the same side of the benzonaphthofuran.

When the organic compounds P1 to P24 are used as the light-emitting auxiliary materials, compared with Ref2 and Ref3 which are used as the light-emitting auxiliary materials, the organic compounds P1 to P24 are connected with the benzonaphthofuran through phenyl (such as the organic compound P2) on 9-phenylcarbazole, so that the electron cloud distribution is more uniform, the hole transmission capability is more uniform, the electron blocking capability is more suitable, and the light-emitting efficiency and the service life of the light-emitting element are improved.

In addition, compared with the comparative elements 1 to 4, which are the light-emitting auxiliary materials of Ref1 to Ref4, the organic compounds P1 to P24 have better thermal stability than the organic compounds with larger molecular weight of Ref1 to Ref4, which is also beneficial to improving the light-emitting efficiency and the service life of the light-emitting element.

According to the light-emitting element disclosed by the embodiment of the invention, the organic compound has the structure shown in the general formula (1), the carbazolyl and the arylamine in the organic compound are connected to the same side of naphthobenzofuran or naphthobenzothiophene, so that higher molecular torsion degree is obtained, better film forming effect and more stable hole transmission performance are easily obtained when the organic compound is applied to the light-emitting element, and meanwhile, the phenyl is connected to the 9 # position of the carbazolyl so as to be connected to the naphthobenzofuran or the naphthobenzothiophene, so that the electron cloud distribution of the organic compound is more uniform, more balanced hole transmission capability and more suitable electron blocking capability can be obtained when the organic compound is applied to the light-emitting element, 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.

The display panel also comprises an array substrate positioned at one side of the light-emitting element and a packaging layer which is positioned at one side of the light-emitting element away from the array substrate and covers 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, the carbazolyl and the arylamine in the organic compound are connected to the same side of the naphthobenzofuran or naphthobenzothiophene, so that higher molecular torsion degree is obtained, better film forming effect and more stable hole transmission performance are easily obtained when the organic compound is applied to the light-emitting element, and meanwhile, the phenyl is connected to the 9 # position of the carbazolyl so as to be connected to the naphthobenzofuran or the naphthobenzothiophene, so that the electron cloud distribution of the organic compound is more uniform, more balanced hole transmission capability and more suitable electron blocking capability can be obtained when the organic compound is applied to the light-emitting element, 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):according to the invention, through using the organic compound with the structure shown in the general formula (1), the carbazolyl and the arylamine in the organic compound are connected to the same side of the naphthobenzofuran or the naphthobenzothiophene, so that higher molecular torsion degree is obtained, better film forming effect and more stable hole transmission performance are easily obtained when the organic compound is applied to a light-emitting element, and meanwhile, the 9-position of the carbazolyl is connected with the phenyl so as to be connected to the naphthobenzofuran or the naphthobenzothiophene, so that the electron cloud distribution of the organic compound is more uniform, more balanced hole transmission capability and more suitable electron blocking capability can be obtained when the organic compound is applied to the light-emitting element, the light-emitting efficiency of the light-emitting element is improved, and the service life of the light-emitting 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

1. An organic compound, characterized in that the organic compound has a structure represented by the general formula (1):

wherein X is selected from O or S;

Ar ¹ selected from naphthyl;

L ¹ selected from substituted or unsubstituted phenylene;

L ² selected from single bond, substituted or unsubstituted phenylene;

2. The organic compound according to claim 1, wherein the organic compound has a structure represented by any one of the general formulae (1-1) to (1-3):

3. the organic compound according to claim 1, wherein Ar ² 、Ar ³ Each independently selected from the following groups:

wherein the method comprises the steps of，R ₃ 、R ₄ 、R ₅ Each occurrence is independently selected from deuterium, a substituted or unsubstituted straight chain alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted branched alkyl or cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms; or, adjacent R ₄ 、R ₅ To form cycloalkyl groups having 3 to 10 carbon atoms;

c is selected from any integer from 0 to 7;

* Representing the ligation site.

4. An organic compound according to claim 3, wherein R ₃ 、R ₄ 、R ₅ Each occurrence is independently selected from deuterium, a substituted or unsubstituted straight chain alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted branched alkyl or cycloalkyl group having 3 to 10 carbon atoms, and a substituted or unsubstituted aromatic group having 6 to 18 ring atoms.

5. The organic compound according to claim 4, wherein R ₄ 、R ₅ Selected from methyl, ar ² 、Ar ³ Each independently selected from the following groups:

6. the organic compound according to any one of claims 1 to 5, wherein R ¹ 、R ² Each independently selected from deuterium or methyl.

7. The organic compound according to claim 1, characterized in that the organic compound is selected from the following compounds:

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8. a light-emitting element, comprising:

a pair of electrodes including a first electrode and a 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, a hole-transporting layer between the light-emitting layer and the first electrode, a light-emitting auxiliary layer between the hole-transporting layer and the light-emitting layer, a hole-injecting layer between the hole-transporting layer and the first electrode, an electron-transporting layer between the light-emitting layer and the second electrode, and an electron-injecting layer between the electron-transporting layer and the second electrode;

wherein the light-emitting auxiliary layer comprises 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.