CN117843502A - Organic compound, light-emitting element, and display panel - Google Patents

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

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CN117843502A
CN117843502A CN202311730725.1A CN202311730725A CN117843502A CN 117843502 A CN117843502 A CN 117843502A CN 202311730725 A CN202311730725 A CN 202311730725A CN 117843502 A CN117843502 A CN 117843502A
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substituted
organic compound
unsubstituted
group
layer
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邹源佐
周世豪
何锐锋
宋晶尧
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Shenzhen China Star Optoelectronics Semiconductor Display Technology Co Ltd
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Shenzhen China Star Optoelectronics Semiconductor Display Technology Co Ltd
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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 invention, the organic compound with the structure shown in the general formula (1) is used, the aromatic amine group is connected to the No. 2 position of the fluorenyl, and the highly twisted large steric hindrance group is introduced to the No. 9 position of the fluorenyl, so that the hole transmission performance is effectively improved, the thermal stability is better, the luminous efficiency of the 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 light-emitting efficiency of the organic electroluminescent element and to extend the service life of the organic electroluminescent element, a suitable hole-transporting material or the like is used in the organic functional layer of the organic electroluminescent element, so that electrons and holes are recombined in the central region of the light-emitting layer, and exciton quenching is reduced. The existing hole transport materials still have defects in performances such as carrier transport, 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 defect of the current hole transport material in the performances of carrier transport and the like.
The present invention provides an organic compound having a structure represented by the general formula (1):
wherein Ar is 1 、Ar 2 Each independently selected from the group consisting of a substituted or unsubstituted cyclic alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a combination thereof;
R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from hydrogen, deuterium, a substituted or unsubstituted straight chain alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cyclic alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 60 ring atoms;
L 1 and L 2 Each independently selected from a single bond or an arylene group having 6 to 30 carbon atoms;
a is selected from any integer from 0 to 4;
b is selected from any integer from 0 to 8;
c is selected from any integer from 0 to 7.
Preferably, the organic compound has a structure as shown in any one of the general formulae (1-1) to (1-2):
preferably Ar 1 、Ar 2 Each independently selected from the following groups:
wherein X is selected from N, C or CR 6 ；
Y is selected from O, S, NR 7 Or CR (CR) 8 R 9 ；
R 6 、R 7 、R 8 、R 9 Each occurrence is independently selected from hydrogen, deuterium, a substituted or unsubstituted straight chain alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cyclic alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group having 6 to 60 ring atoms.
Preferably, R 6 、R 7 、R 8 、R 9 Each occurrence is independently selected from hydrogen, methyl, ethyl, isopropyl, t-butyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl.
Preferably, R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from hydrogen, 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, a substituted or unsubstituted aryl group having 6 to 10 ring atoms, and a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms.
Preferably, R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from hydrogen, 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.
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 hole transport 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, the organic compound with the structure shown in the general formula (1) is used, the aromatic amine group is connected to the No. 2 position of the fluorenyl, and the highly twisted large steric hindrance group is introduced to the No. 9 position of the fluorenyl, so that the hole transmission performance is effectively improved, the thermal stability is better, the luminous efficiency of the 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. 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-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-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, N-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc.
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 hole transport material in the performances of carrier transport, 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 Ar is 1 、Ar 2 Each independently selected from the group consisting of a substituted or unsubstituted cyclic alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a combination thereof;
R 1 、R 2 、R 3 、R 4 、R 5 each independently selected from hydrogen, deuterium, a substituted or unsubstituted straight chain alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cyclic alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 60 ring atoms;
L 1 And L 2 Each independently selected from a single bond or an arylene group having 6 to 30 carbon atoms;
a is selected from any integer from 0 to 4;
b is selected from any integer from 0 to 8;
c is selected from any integer from 0 to 7.
According to the invention, the organic compound with the structure shown in the general formula (1) is used, the aromatic amine group is connected to the No. 2 position of the fluorenyl, and the highly twisted large steric hindrance group is introduced to the No. 9 position of the fluorenyl, so that the hole transmission performance is effectively improved, the thermal stability is better, the luminous efficiency of the 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 (1-1) to (1-2):
in some embodiments, ar 1 、Ar 2 Each independently selected from a cyclic alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 30 ring atoms, or a combination thereof.
In some embodiments, ar 1 、Ar 2 Each independently selected from the group consisting of a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 20 ring atoms, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, and a cyclic alkyl group having 3 to 10 carbon atoms.
In some embodiments, ar 1 、Ar 2 Each independently selected from the group consisting of a substituted or unsubstituted aromatic group having 6 to 15 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 12 ring atoms, a substituted or unsubstituted aromatic group having 6 to 15 ring atoms, and a cyclic alkyl group having 3 to 10 carbon atoms.
In some embodiments, ar 1 、Ar 2 Each independently selected from the following groups:
wherein X is selected from N, C or CR 6 X linked to the adjacent group is selected from C.
Y is selected from O, S, NR 7 Or CR (CR) 8 R 9 ；
R 6 、R 7 、R 8 、R 9 Each occurrence is independently selected from hydrogen, deuterium, substituted or unsubstituted straight chain alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted straight chain alkyl groups having 3 to 20 carbon atomsBranched alkyl group having carbon atoms, substituted or unsubstituted cyclic alkyl group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic group having 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic group having 6 to 60 ring atoms.
In some embodiments, R 6 、R 7 、R 8 、R 9 Each occurrence is independently selected from hydrogen, 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, a substituted or unsubstituted aryl group having 6 to 10 ring atoms, and a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms.
In some embodiments, R 6 、R 7 、R 8 、R 9 Each occurrence is independently selected from methyl, ethyl, isopropyl, t-butyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl.
In some embodiments, R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from the group consisting of 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, a substituted or unsubstituted aryl group having 6 to 10 ring atoms, and a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms.
In some embodiments, R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from the group consisting of 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, and substituted or unsubstituted dibenzofuranyl groups.
In some embodiments, R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from the group consisting of substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted t-butyl, substituted or unsubstituted cyclopentA group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group.
In some embodiments, substituted methyl, substituted ethyl, substituted isopropyl, substituted tert-butyl, substituted cyclopentyl, substituted cyclohexyl, substituted adamantyl, substituted phenyl, substituted naphthyl, substituted dibenzofuranyl satisfy the following conditions: at least one H in the group is replaced by deuterium.
In some embodiments, L 1 、L 2 Each independently selected from a single bond, phenyl, naphthyl, phenanthryl, carbazolyl, and the like.
In some embodiments, a may be selected from 0, 1, 2, 3, or 4 when a is selected from any one integer from 0 to 4.
In some embodiments, b may be selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8 when b is selected from any one integer from 0 to 8.
In some embodiments, when c is selected from any one integer from 0 to 7, c may be selected from 0, 1, 2, 3, 4, 5, 6, or 7.
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 connection site of the arylamine group is fixed at the number 2 position of the fluorenyl group, so that the potential barrier of hole transmission is reduced, the more proper carrier transmission rate is obtained, the hole transmission capacity is enhanced, the film forming property of the organic compound is improved, the higher thermal stability is obtained, the luminous efficiency of a luminous element is facilitated, 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. 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.
The luminescent guest material is selected from singlet state luminophores (fluorescent luminophores), triplet state luminophores (phosphorescent luminophores) and TADF materials.
The organic compound may be used as a hole transport 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 condensed aromatic derivative or a heteroaromatic compound, and a guest material that is one or more of the organic compounds 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 may be selected from organic compounds as described previously.
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 25.
Synthesis of intermediates I-1 to I-12
The synthetic route of intermediate I-1 is as follows:
synthesis of intermediate I-1:
synthesis of intermediate I-1-2: i-1-1 (29.9 g,0.15 mol) and p-chlorophenylboronic acid (23.5 g,0.15 mol) were weighed into a clean three-necked flask, and Pd (PPh) was added 3 ) 4 (1%, 1.7 g), potassium carbonate (41.5 g,0.30 mol), 1, 4-dioxane (400 mL) and deionized water (100 mL), replacing nitrogen three times, heating to 80 ℃ and carrying out reflux reaction for 6h; naturally cooling, washing and separating liquid, drying an organic phase, spin-drying, and performing column chromatography to obtain an intermediate I-1-2, wherein the yield is 89.8%, and the result of an atmospheric pressure solid phase analysis probe mass spectrum (ASAP-MS) of the intermediate I-1-2 is as follows: MS (ASAP) =231.
Synthesis of intermediate I-1: weighing I-1-3 (43.6 g,0.13 mol) and placing the mixture into a clean double-neck flask, adding 360mL of tetrahydrofuran for full dissolution, sealing, replacing nitrogen for deoxidization, cooling the system to the temperature of minus 78 ℃, slowly dripping n-butyl lithium solution (56 mL,0.14 mol), keeping stirring at low temperature for 2h, then adding 120mL of tetrahydrofuran solution dissolved with I-1-2 (27.7 g,0.12 mol), naturally heating to room temperature, and continuing stirring for 3h to obtain a crude product I-1-4; adding saturated ammonium chloride solution, mixing, separating, taking an organic phase, spin-drying the solvent, adding 20mL of hydrochloric acid and 120mL of glacial acetic acid, heating at 100 ℃ for reaction for 4 hours, cooling to room temperature after the reaction is finished, adding ice water to precipitate solid, filtering to obtain a crude I-1 solid, and purifying by column chromatography to obtain an intermediate I-1, wherein the yield is 65.6%, and MS (ASAP) =469.
The synthetic route of intermediate I-2 is as follows:
synthesis of intermediate I-2:
referring to the synthesis of I-1, replacement of I-1-3 with I-2-1 gives intermediate I-2 in 54.6% yield, MS (ASAP) =469.
The synthetic route of intermediate I-3 is as follows:
synthesis of intermediate I-3:
synthesis of intermediate I-3-2: referring to the synthesis of I-1-2 in the synthesis of intermediate I-1, replacement of I-1-1 with I-3-1 gives intermediate I-3-2 in 79.6% yield, MS (ASAP) =234.
Synthesis of intermediate I-3: referring to the synthesis of intermediate I-1, replacement of I-1-2 with I-3-2 gives intermediate I-3 in 56.7% yield, MS (ASAP) =472.
The synthetic route for intermediate I-4 is as follows:
synthesis of intermediate I-4:
referring to the synthesis of intermediate I-1, replacement of I-1-2 with I-3-2 and I-1-3 with I-4-1 gave intermediate I-4 in 50.3% yield, MS (ASAP) =475.
The synthetic route of intermediate I-5 is as follows:
synthesis of intermediate I-5:
synthesis of intermediate I-5-2: referring to the synthesis method of I-1-2 in the synthesis of intermediate I-1, I-1-1 was replaced with I-5-1, to obtain intermediate I-5-2 in 73.3% yield, MS (ASAP) =245.
Synthesis of intermediate I-5: referring to the synthesis of intermediate I-1, replacement of I-1-2 with I-5-2 gives intermediate I-5 in 43.1% yield, MS (ASAP) =483.
The synthetic route of intermediate I-6 is as follows:
synthesis of intermediate I-6:
synthesis of intermediate I-6-2: referring to the synthesis method of I-1-2 in the synthesis of intermediate I-1, I-1-1 was replaced with I-6-1 to obtain intermediate I-6-2 in a yield of 71.8%, MS (ASAP) =259.
Synthesis of intermediate I-6: referring to the synthesis of intermediate I-1, replacement of I-1-2 with I-6-2 gives intermediate I-6 in 41.5% yield, MS (ASAP) =497.
The synthetic route of intermediate I-7 is as follows:
synthesis of intermediate I-7:
synthesis of intermediate I-7-2: referring to the synthesis method of I-1-2 in the synthesis of intermediate I-1, I-1-1 was replaced with I-7-1, to obtain intermediate I-7-2 in a yield of 76.2%, MS (ASAP) =273.
Synthesis of intermediate I-7: referring to the synthesis of intermediate I-1, replacement of I-1-2 with I-7-2 gives intermediate I-7 in 40.3% yield, MS (ASAP) =511.
The synthetic route of intermediate I-8 is as follows:
synthesis of intermediate I-8:
referring to the synthesis of intermediate I-1, replacement of I-1-2 with I-7-2 and I-1-3 with I-2-1 gave intermediate I-8 in 46.7% yield, MS (ASAP) =511.
The synthetic route of intermediate I-9 is as follows:
synthesis of intermediate I-9:
referring to the synthesis of intermediate I-1, replacement of I-1-3 with I-9-1 gives intermediate I-9 in 63.5% yield, MS (ASAP) =497.
The synthetic route of intermediate I-10 is as follows:
synthesis of intermediate I-10:
synthesis of intermediate I-10-2: referring to the synthesis of I-1-2 in the synthesis of intermediate I-1, replacement of I-1-1 with I-10-1 gives intermediate I-10-2 in 66.7% yield, MS (ASAP) =307.
Synthesis of intermediate I-10: referring to the synthesis of intermediate I-1, replacement of I-1-2 with I-10-2 gave intermediate I-10 in 61.0% yield, MS (ASAP) =545.
The synthetic route of intermediate I-11 is as follows:
synthesis of intermediate I-11:
synthesis of intermediate I-11-2: referring to the synthesis method of I-1-2 in the synthesis of intermediate I-1, p-chlorobenzoic acid was replaced with I-11-1 to obtain intermediate I-11-2 in a yield of 70.1%, MS (ASAP) =397.
Synthesis of intermediate I-11: referring to the synthesis of intermediate I-1, replacement of I-1-2 with I-11-2 gives intermediate I-11 in 52.8% yield, MS (ASAP) =635.
The synthetic route of intermediate I-12 is as follows:
synthesis of intermediate I-12:
referring to the synthesis of intermediate I-1, replacement of I-1-3 with I-12-1 gave intermediate I-12 in 66.7% yield, MS (ASAP) =468.
Example 1
Organic compound P1%) Is 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:
weighing I-1 (18.8 g,40 mmol) and P1-1 (12.9 g,40 mmol) into a clean three-neck flask and adding Pd (dba) 2 (1%, 0.23 g), X-Phos (0.38 g,0.8 mmol), sodium t-butoxide (7.7 g,80 mmol), and anhydrous toluene (400 mL), nitrogen was replaced three times, and the temperature was raised to 110℃for 3 hours; naturally cooling, washing, separating, drying the organic phase, spin drying, and performing column chromatography to obtain the organic compound P1, wherein the yield is 81.0%, and MS (ASAP) =754.
Example 2
Organic compound P2# -) Is 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:
referring to the synthesis method of organic compound P1, P1-1 was replaced with P2-1, yielding organic compound P2 in a yield of 72.2%, MS (ASAP) =718.
Example 3
Organic compound P3# -) Is synthesized by (a)
The synthetic route for organic compound P3 is as follows:
/>
the specific synthetic procedure for organic compound P3 is as follows:
referring to the synthesis method of organic compound P1, P1-1 was replaced with P3-1, yielding organic compound P3 in 79.5% yield, MS (ASAP) =794.
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:
Referring to the synthesis method of organic compound P1, P1-1 was replaced with P4-1, yielding organic compound P4 in a yield of 81.3%, MS (ASAP) =728.
Example 5
Organic compound P5# -) Is synthesized by (a)
The synthetic route for organic compound P5 is as follows:
the specific synthetic procedure for organic compound P5 is as follows:
referring to the synthesis method of organic compound P1, P1-1 was replaced with P5-1, yielding organic compound P5 in a yield of 68.7%, MS (ASAP) =734.
Example 6
Organic compound P6# -) Is synthesized by (a)
The synthetic route for organic compound P6 is as follows:
the specific synthetic procedure for organic compound P6 is as follows:
referring to the synthesis method of organic compound P1, P1-1 was replaced with P6-1, to obtain organic compound P6 in 73.0% yield, MS (ASAP) =754.
Example 7
Organic compound P7%) Is synthesized by (a)
The synthetic route for organic compound P7 is as follows:
the specific synthetic procedure for organic compound P7 is as follows:
referring to the synthesis method of organic compound P1, P1-1 was replaced with P7-1, to obtain organic compound P7 in a yield of 62.9%, MS (ASAP) =778.
Example 8
Organic compound P8# -) Is synthesized by (a)
The synthetic route for organic compound P8 is as follows:
the specific synthetic procedure for organic compound P8 is as follows:
Referring to the synthesis method of organic compound P1, P1-1 was replaced with P8-1, yielding organic compound P8 in 69.4% yield, MS (ASAP) =824.
Example 9
Organic compound P9# -) Is synthesized by (a)
The synthetic route for organic compound P9 is as follows:
the specific synthetic procedure for organic compound P9 is as follows:
referring to the synthesis method of organic compound P1, P1-1 was replaced with P9-1, yielding organic compound P9 in a yield of 78.1%, MS (ASAP) =834.
Example 10
Organic compound P10# -) Is synthesized by (a)
The synthetic route for organic compound P10 is as follows:
the specific synthetic procedure for organic compound P10 is as follows:
referring to the synthesis method of organic compound P1, substitution of P1-1 for P10-1 and I-1 for I-2 gave organic compound P10 in a yield of 70.8%, MS (ASAP) =754.
Example 11
Organic compound P11%) Is synthesized by (a)
The synthetic route for organic compound P11 is as follows:
the specific synthetic procedure for organic compound P11 is as follows:
referring to the synthesis method of organic compound P1, substitution of P1-1 with P11-1 and I-1 with I-2 gave organic compound P11 in 56.2% yield, MS (ASAP) =794.
Example 12
Organic compound P12# -) Is synthesized by (a)
The synthetic route for organic compound P12 is as follows:
The specific synthetic procedure for organic compound P12 is as follows:
referring to the synthesis method of the organic compound P1, substitution of P1-1 with P12-1 and I-1 with I-2 gave the organic compound P12 in a yield of 71.0%, MS (ASAP) =728.
Example 13
Organic compound P13# -) Is synthesized by (a)
The synthetic route for organic compound P13 is as follows:
the specific synthetic procedure for organic compound P13 is as follows:
referring to the synthesis method of organic compound P1, substitution of P1-1 for P13-1 and I-1 for I-2 gave organic compound P13 in 57.1% yield, MS (ASAP) =754.
Example 14
Organic compound P14) Is synthesized by (a)
The synthetic route for organic compound P14 is as follows:
the specific synthetic procedure for organic compound P14 is as follows:
referring to the synthesis method of organic compound P1, substitution of P1-1 for P14-1 and I-1 for I-3 gave organic compound P14 in 76.7% yield, MS (ASAP) =797.
Example 15
Organic compound P15# -) Is synthesized by (a)
The synthetic route for organic compound P15 is as follows:
the specific synthetic procedure for organic compound P15 is as follows:
referring to the synthesis method of organic compound P1, substitution of P1-1 for P10-1 and I-1 for I-4 gave organic compound P15 in 77.8% yield, MS (ASAP) =760.
Example 16
Organic compound P16# -) Is synthesized by (a)
The synthetic route for organic compound P16 is as follows:
the specific synthetic procedure for organic compound P16 is as follows:
referring to the synthesis method of organic compound P1, P1-1 was replaced with P16-1, yielding organic compound P16 in a yield of 68.3%, MS (ASAP) =812.
Example 17
Organic compound P17# -) Is synthesized by (a)
The synthetic route for organic compound P17 is as follows:
the specific synthetic procedure for organic compound P17 is as follows:
referring to the synthesis method of organic compound P1, replacement of I-1 with I-5 and P1-1 with P17-1 gave organic compound P17 in 74.3% yield, MS (ASAP) =808.
Example 18
Organic compound P18# -) Is synthesized by (a)
The synthetic route for organic compound P18 is as follows:
the specific synthetic procedure for organic compound P18 is as follows:
referring to the synthesis method of organic compound P1, replacement of I-1 with I-6 and P1-1 with P11-1 gave organic compound P18 in 71.0% yield, MS (ASAP) =822.
Example 19
Organic compound P19%) Is synthesized by (a)
The synthetic route for organic compound P19 is as follows:
the specific synthetic procedure for organic compound P19 is as follows:
referring to the synthesis method of organic compound P1, replacement of I-1 with I-7 and P1-1 with P19-1 gave organic compound P19 in 66.7% yield, MS (ASAP) =961.
Example 20
Organic compound P20# -) Is synthesized by (a)
The synthetic route for organic compound P20 is as follows:
the specific synthetic procedure for organic compound P20 is as follows:
referring to the synthesis method of organic compound P1, replacement of I-1 with I-8 and P1-1 with P10-1 gave organic compound P20 in 75.1% yield, MS (ASAP) =796.
Example 21
Organic compound P21# -) Is synthesized by (a)
The synthetic route for organic compound P21 is as follows:
the specific synthetic procedure for organic compound P21 is as follows:
referring to the synthesis method of organic compound P1, replacement of I-1 with I-9 and P1-1 with P11-1 gave organic compound P21 in a yield of 65.8%, MS (ASAP) =822.
Example 22
Organic compound P22# -) Is synthesized by (a)
The synthetic route for organic compound P22 is as follows:
the specific synthetic procedure for organic compound P22 is as follows:
referring to the synthesis method of organic compound P1, replacement of I-1 with I-10 and P1-1 with P22-1 gave organic compound P22 in 83.3% yield, MS (ASAP) =808.
Example 23
Organic compound P23# -) Is synthesized by (a)
The synthetic route for organic compound P23 is as follows:
the specific synthetic procedure for organic compound P23 is as follows:
referring to the synthesis method of organic compound P1, replacement of I-1 with I-10 and P1-1 with P23-1 gave organic compound P23 in 82.7% yield, MS (ASAP) =844.
Example 24
Organic compound P24# -) Is synthesized by (a)
The synthetic route for organic compound P24 is as follows:
the specific synthetic procedure for organic compound P24 is as follows:
referring to the synthesis method of organic compound P1, replacement of I-1 with I-11 and P1-1 with P24-1 gave organic compound P24 in 67.9% yield, MS (ASAP) =845.
Example 25
Organic compound P25# -) Is synthesized by (a)
The synthetic route for organic compound P25 is as follows:
the specific synthetic procedure for organic compound P25 is as follows:
referring to the synthesis method of organic compound P1, replacement of I-1 with I-12 and P1-1 with P17-1 gave organic compound P25 in 86.1% yield, MS (ASAP) =793.
Exemplary fabrication steps for the light emitting element provided by the present invention are shown in exemplary embodiment 26 below.
Example 26
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 30nm;
c. forming a hole transport layer: evaporating a hole transport material 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 luminescent auxiliary material Prime on the hole transport layer to form a luminescent auxiliary layer, wherein the thickness of the luminescent auxiliary layer is 10nm;
e. forming a light emitting layer: evaporating a light-emitting layer on the light-emitting auxiliary layer, wherein BH is used as a main material, BD is used as a doping material, the mass ratio of BH to BD 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 25, and the contrast elements 1 to 3 are obtained through the above steps. The hole transport materials used in the light emitting elements 1 to 25 are organic compounds P1 to P25, respectively, and the hole transport materials used in the comparative elements 1 to 3 are Ref1, ref2, and Ref3, respectively.
Specifically, HATCN, prime, BH, BD, ET, liq, ref, ref2 and Ref3 are all commercially available or synthesized from known synthetic methods and existing raw materials, and the chemical structural formula of the above compound is as follows:
in the present embodiment, the current-voltage (J-V) characteristics of the light emitting elements 1 to 25 and the comparative elements 1 to 3 were tested, and the current density of each of the light emitting elements and the comparative elements was 10mA/cm 2 The voltage at the time, the time required for the luminance to drop to 95% of the initial luminance @1000nits (relative lifetime), and the relative external quantum efficiency are shown in table 1.
Table 1: performance data of light emitting elements 1 to 25 and comparison elements 1 to 3
Voltage (V) Relative life span Relative external quantum efficiency
Light-emitting element 1 4.4 1.3 126％
Light-emitting element 2 4.4 1.5 138％
Light-emitting element 3 4.4 1.6 139％
Light-emitting element 4 4.4 1.3 120％
Light-emitting element 5 4.4 1.2 112％
Light-emitting element 6 4.3 1.3 123％
Light-emitting element 7 4.4 1.5 133％
Light-emitting element 8 4.4 1.1 111％
Light-emitting element 9 4.4 1.7 163％
Light-emitting element 10 4.4 1.3 129％
Light-emitting element 11 4.5 1.5 131％
Light-emitting element 12 4.4 1.3 133％
Light-emitting element 13 4.4 1.3 128％
Light-emitting element 14 4.4 1.4 144％
Light-emitting element 15 4.4 1.5 139％
Light emitting element 16 4.3 1.3 113％
Light emitting element 17 4.4 1.5 166％
Light emitting element 18 4.4 1.5 141％
Light emitting element 19 4.4 1.3 123％
Light-emitting element 20 4.4 1.3 129％
Light emitting element 21 4.3 1.6 142％
Light-emitting element 22 4.4 1.2 131％
Light-emitting element 23 4.4 1.3 128％
Light emitting element 24 4.4 1.1 120％
Light emitting element 25 4.4 1.7 169％
Contrast element 1 4.8 1.0 100％
Contrast element 2 4.5 0.9 106％
Contrast element 3 4.4 0.7 101％
As can be seen from table 1, the light-emitting elements 1 to 25 obtained by using the organic compounds P1 to P25 as the hole transport materials in the hole transport layer according to the present invention have significantly improved light-emitting efficiency and lifetime compared to the comparative elements 1 to 3, wherein the light-emitting efficiency of the light-emitting elements 1 to 25 is more than 111% compared to the comparative element 1, and the lifetime of the light-emitting elements 1 to 25 is more than 1.1 times compared to the comparative element 1.
When the organic compounds P1 to P25 are used as the hole transport materials, the organic compounds P1 to P25 have the highest occupied molecular orbital (HOMO, highest Occupied Molecular Orbital) energy levels of the organic compounds P1 to P25 more suitable by fixing the connection site of the arylamine group on the fluorenyl group at the number 2 position than Ref1 and Ref2, and the barrier for hole transport is reduced, thereby improving the carrier transport performance in the light emitting element.
When the organic compounds P1 to P25 are used as the hole transport material, the organic compounds P1 to P25 introduce a large steric hindrance group at the number 9 of the fluorenyl group, compared with Ref3 as the hole transport material, the film forming property of the organic compounds P1 to P25 is enhanced, and higher thermal stability is obtained while improving the carrier transport property in the light emitting element.
According to the light-emitting element disclosed by the embodiment of the invention, the organic compound is used for connecting the aromatic amine group to the No. 2 position of the fluorenyl and introducing the highly twisted large steric hindrance group to the No. 9 position of the fluorenyl, so that the hole transmission performance is effectively improved, the thermal stability is better, 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, so that the hole transmission performance is effectively improved, the thermal stability is better, the light-emitting efficiency of the display panel is improved, and the service life of the display panel 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, the organic compound with the structure shown in the general formula (1) is used, the aromatic amine group is connected to the No. 2 position of the fluorenyl, and the highly twisted large steric hindrance group is introduced to the No. 9 position of the fluorenyl, so that the hole transmission performance is effectively improved, the thermal stability is better, the luminous efficiency of the 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 Ar is 1 、Ar 2 Each independently selected from the group consisting of a substituted or unsubstituted cyclic alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a combination thereof;
R 1 、R 2 、R 3 、R 4 、R 5 each independently selected from hydrogen, deuterium, a substituted or unsubstituted straight chain alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cyclic alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 60 ring atomsA heteroaromatic group;
L 1 and L 2 Each independently selected from a single bond or an arylene group having 6 to 30 carbon atoms;
a is selected from any integer from 0 to 4;
b is selected from any integer from 0 to 8;
c is selected from any integer from 0 to 7.
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 (1-2):
3. The organic compound according to claim 1, wherein Ar 1 、Ar 2 Each independently selected from the following groups:
wherein X is selected from N, C or CR 6 ；
Y is selected from O, S, NR 7 Or CR (CR) 8 R 9 ；
R 6 、R 7 、R 8 、R 9 Each occurrence is independently selected from hydrogen, deuterium, a substituted or unsubstituted straight chain alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cyclic alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group having 6 to 60 ring atoms.
4. An organic compound according to claim 3, wherein R 6 、R 7 、R 8 、R 9 Each occurrence is independently selected from hydrogen, methyl, ethyl, isopropyl, t-butyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl.
5. The organic compound according to any one of claims 1 to 4, wherein R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from hydrogen, 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, a substituted or unsubstituted aryl group having 6 to 10 ring atoms, and a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms.
6. The organic compound according to claim 5, wherein R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from hydrogen, 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.
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;
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, 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 hole transport 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.
CN202311730725.1A 2023-12-15 2023-12-15 Organic compound, light-emitting element, and display panel Pending CN117843502A (en)

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