Organic compound, light-emitting element, and display panel

Abstract

This invention discloses an organic compound, a light-emitting element, and a display panel. The organic compound has a structure as shown in general formula (1). By using an organic compound with the structure shown in general formula (1), the organic compound connects an aromatic amine group to the 2 position of the fluorenyl group and introduces a highly distorted sterically hindered group at the 9 position of the fluorenyl group. The hole transport performance is effectively improved and the thermal stability is better, thereby improving the luminous efficiency of the light-emitting element and extending the service life of the light-emitting element.

Description

Technical Field

[0001] This invention relates to the field of displays, and more specifically to an organic compound, a light-emitting element, and a display panel. Background Technology

[0002] Currently, organic electroluminescent devices (OLEDs) typically consist of a positive electrode, a negative electrode, and an organic layer between them. The organic material in the organic layer converts electrical energy into light energy, thus achieving organic electroluminescence. When a voltage is applied between the positive and negative electrodes of the OLED, holes are injected into the organic layer from the positive electrode, and electrons are injected into the organic layer from the negative electrode. The injected holes and electrons meet to form excitons, which emit light when they transition back to the ground state, thereby realizing the light emission of the OLED. OLEDs possess characteristics such as self-luminescence, high brightness, high efficiency, low voltage driving, wide viewing angle, high contrast, and high response, therefore, organic electroluminescent devices have broad application prospects.

[0003] To improve the luminous efficiency and extend the lifespan of organic light-emitting diodes (OLEDs), suitable hole transport materials are used in the organic functional layers of the OLEDs to facilitate electron-hole recombination in the central region of the light-emitting layer and reduce exciton quenching. However, existing hole transport materials still have shortcomings in carrier transport and other properties, leaving room for improvement in the luminous efficiency and lifespan of OLEDs.

[0004] Therefore, there is an urgent need for an organic compound, a light-emitting element, and a display panel to solve the above-mentioned technical problems. Summary of the Invention

[0005] This invention provides an organic compound, a light-emitting element, and a display panel, which can alleviate the technical problem that the luminous efficiency and lifespan of organic electroluminescent elements are difficult to improve due to the shortcomings of current hole transport materials in terms of carrier transport and other properties.

[0006] This invention provides an organic compound having a structure as shown in general formula (1):

[0007]

[0008] Among them, Ar 1 Ar 2 The groups are selected independently from cyclic alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 60 cyclic atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 cyclic atoms, or combinations thereof;

[0009] R 1 R 2 R 3 R 4R 5 The groups are independently selected from hydrogen, deuterium, substituted or unsubstituted linear alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted branched alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted cyclic alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 60 cyclic atoms, and substituted or unsubstituted heteroaromatic groups having 6 to 60 cyclic atoms.

[0010] L 1 and L 2 Each is independently selected from a single bond or an arylene group having 6 to 30 carbon atoms;

[0011] a is any integer from 0 to 4;

[0012] b is any integer from 0 to 8;

[0013] c is any integer from 0 to 7.

[0014] Preferably, the organic compound has a structure as shown in any one of general formulas (1-1) to (1-2):

[0015]

[0016] Preferred, Ar 1 Ar 2 Each group is independently selected from the following groups:

[0017]

[0018] Where X is selected from N, C or CR 6 ;

[0019] Y is selected from O, S, NR 7 or CR 8 R 9 ;

[0020] R 6 R 7 R 8 R 9 Each time it appears, it is independently selected from hydrogen, deuterium, substituted or unsubstituted linear alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted branched alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted cyclic alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 60 cyclic atoms, or substituted or unsubstituted heteroaromatic groups having 6 to 60 cyclic atoms.

[0021] Preferred, R 6 R 7 R 8 R 9Each time it appears, it is independently selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, and naphthyl.

[0022] Preferred, R 1 R 2 R 3 R 4 R 5 The groups are independently selected from hydrogen, deuterium, substituted or unsubstituted straight-chain alkyl groups having 1 to 5 carbon atoms, substituted or unsubstituted branched alkyl or cycloalkyl groups having 3 to 10 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 10 cyclic atoms, and substituted or unsubstituted heteroaromatic groups having 6 to 14 cyclic atoms.

[0023] Preferred, R 1 R 2 R 3 R 4 R 5 Each of the following is independently selected from hydrogen, deuterium, substituted or unsubstituted linear alkyl groups having 1 to 3 carbon atoms, substituted or unsubstituted tert-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.

[0024] Preferably, the organic compound is selected from the following compounds:

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038] The present invention also provides a light-emitting element, comprising:

[0039] A pair of electrodes, including a first electrode and a second electrode;

[0040] An organic functional layer located between the first electrode and the second electrode;

[0041] The organic functional layer is made of at least one organic compound as described above. Preferably, the organic functional layer comprises a light-emitting layer, a hole transport layer between the light-emitting layer and the first electrode, a light-emitting auxiliary layer between the hole transport layer and the light-emitting layer, a hole injection layer between the hole transport layer and the first electrode, an electron transport layer between the light-emitting layer and the second electrode, and an electron injection layer between the electron transport layer and the second electrode.

[0042] The hole transport layer includes at least one organic compound as described above.

[0043] The present invention also provides a display panel including a light-emitting element as described in any of the preceding claims.

[0044] The present invention uses an organic compound having the structure shown in general formula (1), which connects an aromatic amine group to the 2 position of the fluorenyl group and introduces a highly distorted sterically hindered group at the 9 position of the fluorenyl group, thereby effectively improving hole transport performance and thermal stability, thereby improving the luminous efficiency of the light-emitting element and extending the service life of the light-emitting element. Attached Figure Description

[0045] To more clearly illustrate the technical solutions in the embodiments of the present invention, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of the present invention. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0046] Figure 1 This is a schematic diagram of a light-emitting element provided in an embodiment of the present invention. Detailed Implementation

[0047] The technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention. In addition, it should be understood that the specific embodiments described herein are only for illustration and explanation of the present invention and are not intended to limit the present invention. In the present invention, unless otherwise stated, directional terms such as "upper" and "lower" generally refer to the upper and lower positions of the device in actual use or operation, specifically the drawing direction in the accompanying drawings; while "inner" and "outer" refer to the outline of the device. In the present invention, "optionally," "optionally," and "optional" mean that they are optional, that is, they are selected from either "with" or "without" in the parallel schemes. If multiple "optional" appear in a technical solution, unless otherwise specified, and there is no contradiction or mutual constraint relationship, each "optional" is independent. In the present invention, the technical features described in an open-ended manner include both closed technical solutions composed of the listed features and open technical solutions containing the listed features.

[0048] In this invention, aromatic groups, aromatic families, and aromatic ring systems have the same meaning and can be used interchangeably.

[0049] In this invention, heteroaromatic groups, heteroaromatic families, and heteroaromatic ring systems have the same meaning and can be used interchangeably.

[0050] In this invention, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0051] In this invention, when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R, then R can be independently selected from different groups.

[0052] In this invention, "substituted or unsubstituted" means that the defined group may or may not be substituted. When the defined group is substituted, it should be understood that the defined group can be substituted by one or more substituents R, wherein R is selected from, but not limited to: deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-20 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R", silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, halocarbamoyl, formyl, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl, trifluoromethyl, and the above groups may also be further substituted by substituents acceptable in the art; it can be understood that R' and R" in -NR'R" are independently selected from, but not limited to: H, deuterium. The group R is selected from, but is not limited to, deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, and heteroaromatic group containing 5-20 ring atoms. Preferably, R is selected from, but is not limited to, deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-10 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl, trifluoromethyl, and the above groups may be further substituted with substituents acceptable in the art.

[0053] In this invention, "ring atom number" refers to the number of atoms in the ring-forming structure of a compound (e.g., monocyclic compound, fused-ring compound, cross-linked compound, carbocyclic compound, heterocyclic compound) obtained by atomic bonding. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "ring atom number" described below unless otherwise specified. For example, the benzene ring has 6 ring atoms, the naphthalene ring has 10 ring atoms, and the thiophene group has 5 ring atoms.

[0054] In this invention, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. It can be a monocyclic aryl, a fused-ring aryl, or a polycyclic aryl, and for polycyclic rings, at least one ring is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" refers to an aryl containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aryl having 6 to 14 ring atoms, with optional further substitution on the aryl group; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, fluoranyl, triphenylene, pyrene, perylene, tetraphenyl, fluorenyl, dinaphthylphenyl, acenaphthyl, and their derivatives. It is understandable that multiple aryl groups can also be interrupted by short non-aromatic units (e.g., <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, and diaryl ether systems should also be included in the definition of aryl.

[0055] In this invention, "heteroaryl or heteroaromatic group" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom, which can be an N atom, O atom, S atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" refers to a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms. The heteroaryl group may optionally be further substituted, and suitable examples include, but are not limited to, thiophene, furanyl, pyrrole, imidazolyl, diazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, and pyrimidine. Triazinyl, acridineyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridinylpyrimidinyl, pyridinylpyrazinyl, benzothiopheneyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienopyrrolyl, furanolyl, furanolyl, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, o-diazonyl, phenanthridineyl, primidyl, quinazolinoneyl, dibenzothiopheneyl, dibenzofuranyl, carbazoleyl and their derivatives.

[0056] In this invention, "alkyl" can refer to straight-chain, branched, and / or cyclic alkyl groups. The number of carbon atoms in an alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Phrases containing this term, such as "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each time it appears, it can independently be a C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, or C9 alkyl. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, etc. tert-amyl, 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, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl The compounds include 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-pentadecanyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-hepta ...

[0057] In this invention, the abbreviations for substituents are: n-n-, sec-sec-, i-iso-, t-tert-, o-ortho-, m-me-, p-para-, Me-methyl, Et-ethyl, Pr-propyl, Bu-butyl, Am-pentyl, Hx-hexyl, Cy-cyclohexyl.

[0058] In this invention, "amino group" refers to an amine derivative having the structural feature of formula -N(X)2, wherein each "X" is independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, etc. Non-limiting types of amino groups include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclic)2, -NH(heterocyclic), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic), -N(cycloalkyl)(heterocyclic), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0059] In this invention, unless otherwise defined, hydroxyl refers to -OH, carboxyl refers to -COOH, carbonyl refers to -C(=O)-, amino refers to -NH2, formyl refers to -C(=O)H, haloformyl refers to -C(=O)Z (where Z represents halogen), carbamoyl refers to -C(=O)NH2, isocyanate refers to -NCO, and isothiocyanate refers to -NCS.

[0060] In this invention, the term "alkoxy" refers to a group with the structure "-O-alkyl", that is, an alkyl group as defined above that is attached to other groups via an oxygen atom. Suitable examples of phrases containing this term include, but are not limited to: methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), and tert-butoxy (-OC(CH3)3 or -OtBu).

[0061] In this invention, the "*" connected to a single bond indicates a connection or fusion site.

[0062] In this invention, when no linking site is specified in the group, it means that any linkable site in the group is selected as the linking site.

[0063] In this invention, when no fusion site is specified in the group, it means that any fusionable site in the group is selected as the fusion site, preferably two or more sites in the adjacent position of the group are fusion sites.

[0064] In this invention, when the same group contains multiple substituents with the same symbol, the substituents can be the same as or different from each other, for example... The six R's on the benzene ring can be the same or different from each other.

[0065] In this invention, the single bond connecting the substituents extends through the corresponding ring, indicating that the substituent can be attached to any position on the ring, for example... R is attached to any substituted site on the benzene ring; such as express Can be with A fused ring can be formed at any position on the benzene ring.

[0066] According to the present invention, cycloalkyl or cycloalkyl means have the same meaning and can be used interchangeably.

[0067] In this invention, "adjacent groups" refers to two substituents that have no substituted sites between them.

[0068] In this invention, "two adjacent R1, R3, or R5 rings together" means a ring system formed by connecting two adjacent R1, R3, or R5 rings. The ring system can be selected from aliphatic hydrocarbon rings, aliphatic heterocycles, aromatic hydrocarbon rings, or aromatic heterocycles. Preferably, it can form...

[0069] Currently, due to the shortcomings of hole transport materials in terms of carrier transport and charge balance regulation, there is still room for improvement in the luminous efficiency and lifetime of organic electroluminescent elements.

[0070] This invention provides an organic compound having a structure as shown in general formula (1):

[0071]

[0072] Among them, Ar 1 Ar 2 The groups are selected independently from cyclic alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 60 cyclic atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 cyclic atoms, or combinations thereof;

[0073] R 1 R 2 R 3 R 4 R 5 The groups are independently selected from hydrogen, deuterium, substituted or unsubstituted linear alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted branched alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted cyclic alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 60 cyclic atoms, and substituted or unsubstituted heteroaromatic groups having 6 to 60 cyclic atoms.

[0074] L 1 and L 2 Each is independently selected from a single bond or an arylene group having 6 to 30 carbon atoms;

[0075] a is any integer from 0 to 4;

[0076] b is any integer from 0 to 8;

[0077] c is any integer from 0 to 7.

[0078] The present invention uses an organic compound having the structure shown in general formula (1), which connects an aromatic amine group to the 2 position of the fluorenyl group and introduces a highly distorted sterically hindered group at the 9 position of the fluorenyl group, thereby effectively improving hole transport performance and thermal stability, thereby improving the luminous efficiency of the light-emitting element and extending the service life of the light-emitting element.

[0079] In some embodiments, the organic compound has a structure as shown in any of general formulas (1-1) to (1-2):

[0080]

[0081] In some embodiments, Ar 1 Ar 2 Each group is independently selected from cyclic alkyl groups having 3 to 10 carbon atoms, aromatic groups having 6 to 30 substituted or unsubstituted cyclic atoms, heteroaromatic groups having 6 to 30 substituted or unsubstituted cyclic atoms, or combinations thereof.

[0082] In some embodiments, Ar 1 Ar 2 The groups are independently selected from substituted or unsubstituted aromatic groups having 6 to 20 cyclic atoms, substituted or unsubstituted heteroaromatic groups having 6 to 20 cyclic atoms, and combinations of substituted or unsubstituted aromatic groups having 6 to 20 cyclic atoms and cyclic alkyl groups having 3 to 10 carbon atoms.

[0083] In some embodiments, Ar 1 Ar 2 The aromatic group is selected independently from substituted or unsubstituted aromatic groups having 6 to 15 cyclic atoms, substituted or unsubstituted heteroaromatic groups having 6 to 12 cyclic atoms, and substituted or unsubstituted aromatic groups having 6 to 15 cyclic atoms combined with cyclic alkyl groups having 3 to 10 carbon atoms.

[0084] In some embodiments, Ar 1 Ar 2 Each group is independently selected from the following groups:

[0085]

[0086] Where X is selected from N, C or CR 6 The X group connected to the adjacent group is selected from C.

[0087] Y is selected from O, S, NR 7 or CR 8 R 9 ;

[0088] R 6 R 7 R 8 R 9 Each time it appears, it is independently selected from hydrogen, deuterium, substituted or unsubstituted linear alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted branched alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted cyclic alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 60 cyclic atoms, or substituted or unsubstituted heteroaromatic groups having 6 to 60 cyclic atoms.

[0089] In some embodiments, R 6 R 7 R 8 R9 Each time it appears, it is independently selected from hydrogen, substituted or unsubstituted straight-chain alkyl with 1 to 5 carbon atoms, substituted or unsubstituted branched alkyl or cycloalkyl with 3 to 10 carbon atoms, substituted or unsubstituted aromatic group with 6 to 10 cyclic atoms, or substituted or unsubstituted heteroaromatic group with 6 to 14 cyclic atoms.

[0090] In some embodiments, R 6 R 7 R 8 R 9 Each time it appears, it is independently selected from methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, and naphthyl.

[0091] In some embodiments, R 1 R 2 R 3 R 4 R 5 The groups are independently selected from substituted or unsubstituted straight-chain alkyl groups having 1 to 5 carbon atoms, substituted or unsubstituted branched alkyl or cycloalkyl groups having 3 to 10 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 10 cyclic atoms, and substituted or unsubstituted heteroaromatic groups having 6 to 14 cyclic atoms.

[0092] In some embodiments, R 1 R 2 R 3 R 4 R 5 Each of the following is independently selected from substituted or unsubstituted linear alkyl groups having 1 to 3 carbon atoms, substituted or unsubstituted tert-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.

[0093] In some embodiments, R 1 R 2 R 3 R 4 R 5 Each of the following is independently selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted dibenzofuranyl.

[0094] In some embodiments, the substituted methyl, substituted ethyl, substituted isopropyl, substituted tert-butyl, substituted cyclopentyl, substituted cyclohexyl, substituted adamantyl, substituted phenyl, substituted naphthyl, and substituted dibenzofuranyl satisfy the following condition: at least one H in the group is substituted with deuterium.

[0095] In some embodiments, L 1 L 2 Each is independently selected from single bonds, phenyl, naphthyl, phenanthryl, carbazole, etc.

[0096] In some embodiments, when a is selected from any integer from 0 to 4, a can be selected from 0, 1, 2, 3 or 4.

[0097] In some embodiments, when b is selected from any integer from 0 to 8, b can be selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0098] In some embodiments, when c is selected from any integer from 0 to 7, c can be selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0099] In some embodiments, the organic compound is selected from the following compounds:

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113] The organic compound provided in this embodiment of the invention fixes the linkage site of the aromatic amine group at the 2 position of the fluorene group, which helps to reduce the hole transport barrier, obtain a more suitable carrier transport rate, and enhance the hole transport capability. The large steric hindrance group at the 9 position of the fluorene group improves the film-forming properties of the organic compound and obtains higher thermal stability, which is beneficial to the luminous efficiency of the light-emitting element and extends the service life of the light-emitting element.

[0114] The present invention also provides a mixture comprising at least one organic compound as described in any of the above claims and an organic functional material, wherein the organic functional material is selected from at least one of hole transport materials, hole injection materials, hole blocking materials, electron injection materials, electron transport materials, host materials, or guest materials.

[0115] Please see Figure 1 The present invention also provides a light-emitting element, the light-emitting element comprising: 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 organic compounds as described above. The first electrode 101 may be an anode, and the second electrode 102 may be a cathode.

[0116] In some embodiments, the light-emitting element can be an organic light-emitting diode, an organic photovoltaic cell, an organic light-emitting cell, an organic field-effect transistor, an organic light-emitting field-effect transistor, an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon emitting diode, etc., preferably an organic light-emitting diode, an organic light-emitting cell, or an organic light-emitting field-effect transistor.

[0117] In some embodiments, the light-emitting element can be applied to various electronic devices, such as display panels, lighting devices, and light sources.

[0118] In some embodiments, the organic functional layer 103 may be a single layer. In this case, the organic functional layer 103 is a mixture layer, which includes a first compound and a second compound. The first compound is selected from one or more organic compounds as described above, and the second compound is selected from one or more hole injection materials, hole transport materials, electron injection materials, electron transport materials, hole blocking materials, light-emitting guest materials, light-emitting host materials, and organic dyes. For detailed descriptions of the various organic functional materials included in the organic functional layer 103, please refer to WO2010135519A1, US20090134784A1, and WO2011110277A1. The entire contents of these three patent documents are hereby incorporated herein by reference.

[0119] The luminescent object material is selected from singlet luminescent materials (fluorescent materials), triplet luminescent materials (phosphorescent materials), and TADF materials.

[0120] The organic compound can be used as a hole transport material.

[0121] In some embodiments, the organic functional layer 103 may include multiple layers. When the organic functional layer 103 is multilayered, 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.

[0122] 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.

[0123] 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 and a guest material. The guest material may be one or more organic compounds as described above, and the host material may include fused aromatic derivatives or heteroaromatic compounds.

[0124] The light-emitting element has an emission wavelength between 300 and 1000 nm; further, the light-emitting element has an emission wavelength between 350 and 900 nm; even further, the light-emitting element has an emission wavelength between 400 and 800 nm; and still further, the light-emitting element has an emission wavelength within the wavelength range of red light, green light, or blue light.

[0125] In some embodiments, the host material includes fused aromatic ring derivatives, heterocyclic compounds, etc., such as at least one of anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, fluoranthene compounds, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives. The host material can be a host material applied to red light-emitting elements, a host material applied to green light-emitting elements, or a host material applied to blue light-emitting elements. Preferably, the host material is a host material applied to blue light-emitting elements; when the host material is a host material applied to blue light-emitting elements, the host material is preferably an anthracene-based organic compound.

[0126] In some embodiments, the mass ratio of the host material to the guest material is 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 helps to suppress the crystallization of the light-emitting layer 107 and suppress the concentration quenching caused by the high concentration of the guest material, thereby improving the luminous efficiency of the light-emitting element.

[0127] In some embodiments, the anode is a hole-injecting electrode, and the anode can inject holes into the organic functional layer 103, such as by injecting 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 between the work function of the anode and the HOMO (Highest Occupied Molecular Orbital) level or valence band level of the light-emitting material in the light-emitting layer, or the p-type semiconductor material in the hole injection layer, hole transport layer, or electron blocking layer, is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. The material of the anode includes, but is not limited to, at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO (Indium Tin Oxide), aluminum-doped zinc oxide (AZO), or other suitable and known anode materials, which can be readily selected and used by those skilled in the art. The anode material can be deposited using any suitable technique, such as suitable physical vapor deposition methods, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode can be patterned, for example, patterned ITO conductive substrates are commercially available and can be used to fabricate the light-emitting element of the present invention.

[0128] In some embodiments, the cathode is an electron-injecting electrode, and the cathode can inject electrons into the organic functional layer, such as injecting electrons into the electron injection layer, electron transport layer, or 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 serving as the electron injection layer, electron transport layer, or hole blocking layer, is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. All materials that can be used as cathodes in organic electronic devices may be used as cathode materials for the devices of this invention, including but not limited to at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, and ITO. The cathode material can be deposited using any suitable technique, such as suitable physical vapor deposition methods, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0129] In some embodiments, the hole injection layer 104 facilitates hole injection from the anode to the light-emitting layer 107, and the hole injection layer 104 includes a hole injection material that can receive holes injected from the positive electrode at low voltage. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material lies between the work function of the anode material and the HOMO of the 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 metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, polyaniline-based conductive polymers, and polythiophene-based conductive polymers.

[0130] In some embodiments, the hole transport layer 105 can be used to transport holes to the light-emitting layer 107. The hole transport layer 105 includes a hole transport material that receives holes transported from the anode or the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material may be selected from the organic compounds described above.

[0131] In some embodiments, the electron transport layer 108 is used to transport electrons. 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 with high electron mobility known in the art, and may include, but is not limited to, at least one of: Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavonoid-metal complexes, lithium 8-hydroxyquinoline (LiQ), and benzimidazole-based compounds.

[0132] In some embodiments, the electron injection layer 109 is used for injecting electrons. The electron injection layer 109 includes an electron injection material, which preferably has the ability to transport electrons, the effect of injecting electrons from the negative electrode, and the excellent effect of injecting electrons into the light-emitting layer 107 or the light-emitting material. It also has the ability to prevent excitons generated by the light-emitting layer 107 from migrating to the hole injection layer and has excellent thin film formation capabilities. The electron injection material includes, but is not limited to, at least one of lithium 8-hydroxyquinoline (LiQ), fluorenone, anthraquinone dimethane, biphenylquinone, thiamethane dioxide, azoles, diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0133] In some embodiments, the hole blocking layer is used to block holes from reaching the negative electrode, and can typically be formed under the same conditions as the hole injection layer 104. The hole blocking layer includes a hole blocking material, which includes, but is not limited to, at least one of diazole or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc.

[0134] In some embodiments, the light-emitting element further includes a substrate 110, wherein 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 can be a transparent substrate or an opaque substrate. When the substrate 110 is a transparent substrate, a transparent light-emitting element can be fabricated. The substrate 110 can be a rigid substrate or a flexible substrate with elasticity. The material of the substrate 110 can include, but is not limited to, plastics, polymers, metals, semiconductor wafers, or glass. Preferably, the substrate 110 includes at least one smooth surface for forming the anode on the surface. More preferably, the surface is free of surface defects. Preferably, the substrate 110 is made of polymer film or plastic, including but not limited to polyethylene terephthalate (PET material) and polyethylene glycol (2,6-naphthalene) (PEN material). The glass transition temperature of the substrate 110 is greater than or equal to 150°C, preferably greater than or equal to 200°C, more preferably greater than or equal to 250°C, and most preferably greater than or equal to 300°C.

[0135] In some embodiments, the light-emitting element may be a solution-based light-emitting element, that is, at least one of the organic functional layers is prepared by a printing method (e.g., inkjet printing).

[0136] In some embodiments, the materials of the organic functional layer, the mixture layer, or the light-emitting layer can be prepared by composition, and the preparation process can be a printing or coating process. Printing or coating processes include inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, knife coating, roller printing, torsional roller printing, offset printing, flexographic printing, rotary printing, spraying, brushing, pad printing, slot extrusion coating, etc. Preferably, gravure printing, inkjet printing, and other similar processes are used.

[0137] The composition may be a solution or a suspension, and may include a dispersed phase and a dispersant. The dispersed phase is one or more of the organic compounds described above, and the dispersant is used to disperse the dispersed phase.

[0138] In the composition, the mass fraction of the organic compound as described above can be from 0.3% to 30%, preferably from 0.5% to 20%, more preferably from 0.5% to 15%, further preferably from 0.5% to 10%, and most preferably from 1% to 5%.

[0139] When the composition is used in a printing process, the composition can be an ink. The viscosity and surface tension of the ink are important parameters. Suitable surface tension parameters of the ink are suitable for specific substrates and specific printing methods. In some embodiments, the surface tension of the ink at the operating temperature or 25°C ranges from 19 dyne / cm to 50 dyne / cm; preferably from 22 dyne / cm to 35 dyne / cm; more preferably from 25 dyne / cm to 33 dyne / cm, which is beneficial for application in inkjet printing processes. In some embodiments, the viscosity of the ink at the operating temperature or 25°C ranges from 1 cps to 100 cps; preferably from 1 cps to 50 cps; more preferably from 1.5 cps to 20 cps; and most preferably from 4.0 cps to 20 cps, which is beneficial for application in inkjet printing processes.

[0140] In some embodiments, the Hansen solubility parameter of the dispersant is within the following range: the δd (dispersion force) of the dispersant is between 17.0 and 23.2 MPa. 1 / 2 The preferred range is 18.5–21.0 MPa. 1 / 2 The range; δp (polar force) is 0.2–12.5 MPa. 1 / 2 The preferred range is 2.0–6.0 MPa. 1 / 2 The range; δh (hydrogen bond force) is in the range of 0.9–14.2 MPa. 1 / 2 The preferred range is 2.0–6.0 MPa. 1 / 2 The range.

[0141] In some embodiments, the dispersant has a boiling point greater than or equal to 150°C; preferably greater than or equal to 180°C; even more preferably greater than or equal to 200°C; more preferably greater than or equal to 250°C; further preferably greater than or equal to 275°C; and most preferably greater than or equal to 300°C. A boiling point of at least 150°C is beneficial in preventing nozzle clogging of the inkjet printhead during inkjet printing, and a higher boiling point is more conducive to preventing clogging.

[0142] The dispersant may include at least one organic solvent, which can evaporate from the solvent system to form a thin film containing the functional material. The organic solvent may include at least one first organic solvent, which may be selected from aromatic or heteroaromatic compounds. Specifically, the first organic solvent may be selected from p-diisopropylbenzene, pentylene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butyronitrile, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbenzene... Biphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furanate, ethyl 2-furanate, etc.

[0143] The first organic solvent may be selected from aromatic ketone solvents. Specifically, the first organic solvent may be selected from 1-tetrahydronaphthone, 2-tetrahydronaphthone, 2-(phenylepoxy)tetrahydronaphthone, 6-(methoxy)tetrahydronaphthone, acetophenone, phenylacetone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylphenylacetone, 3-methylphenylacetone, 2-methylphenylacetone, etc.

[0144] 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-ethylbenzene, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidylphenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, etc.

[0145] The first organic solvent may be selected from aliphatic ketones. Specifically, the first organic solvent may be selected from aliphatic ketones, such as 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, frankinc, phorone, isophorone, di-n-pentyl ketone, etc.; or aliphatic ethers, such as pentanyl ether, hexane 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, etc.

[0146] The first organic solvent can be selected from organic ester solvents. Specifically, the first solvent can be selected from alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate, etc. are particularly preferred.

[0147] The organic solvent may further include a second organic solvent, which may be selected from one or more solvents such as methanol, ethanol, 2-methoxyethanol, dichloromethane, trichloromethane, 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, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetrahydronaphthalene, naphthane, and indene.

[0148] In addition to the dispersed phase and the dispersant, the composition may also include one or more components such as surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc.

[0149] The exemplary preparation method of the organic compound provided by the present invention is shown in the following exemplary embodiments 1 to 25.

[0150] Synthesis of intermediates I-1 to I-12

[0151] The synthetic route for intermediate I-1 is as follows:

[0152]

[0153] Synthesis of intermediate I-1:

[0154] 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 and placed in a clean three-necked flask. Pd(PPh3)4 (1%, 1.7 g), potassium carbonate (41.5 g, 0.30 mol), 1,4-dioxane (400 mL), and deionized water (100 mL) were added. Nitrogen gas was purged three times, and the mixture was heated to 80 °C and refluxed for 6 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Intermediate I-1-2 was obtained by column chromatography with a yield of 89.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate I-1-2 was: MS(ASAP) = 231.

[0155] Synthesis of intermediate I-1: I-1-3 (43.6 g, 0.13 mol) was weighed and placed in a clean double-necked flask. 360 mL of tetrahydrofuran was added to dissolve it completely. After sealing, nitrogen gas was purged to remove oxygen. The system was cooled to -78 °C and then 56 mL of n-butyllithium solution (0.14 mol) was slowly added dropwise. The mixture was stirred at low temperature for 2 h. Then, 120 mL of tetrahydrofuran solution containing I-1-2 (27.7 g, 0.12 mol) was added. After the mixture was allowed to rise naturally to room temperature, the mixture was stirred for another 3 h to obtain crude product I-1-4. After mixing with saturated ammonium chloride solution, the mixture was separated. The organic phase was collected and the solvent was evaporated. 20 mL of hydrochloric acid and 120 mL of glacial acetic acid were added. The mixture was heated at 100 °C for 4 h. After the reaction was completed, the mixture was cooled to room temperature and ice water was added to precipitate the solid. The solid I-1 was obtained by filtration and purified by column chromatography to obtain intermediate I-1 with a yield of 65.6% and MS (ASAP) = 469.

[0156] The synthetic route for intermediate I-2 is as follows:

[0157]

[0158] Synthesis of intermediate I-2:

[0159] Following the synthesis method of I-1, I-1-3 was replaced with I-2-1 to obtain intermediate I-2 with a yield of 54.6% and MS(ASAP) = 469.

[0160] The synthetic route for intermediate I-3 is as follows:

[0161]

[0162] Synthesis of intermediate I-3:

[0163] Synthesis of intermediate I-3-2: Following the synthesis method of intermediate I-1-2, I-1-1 was replaced with I-3-1 to obtain intermediate I-3-2 with a yield of 79.6% and MS(ASAP) = 234.

[0164] Synthesis of intermediate I-3: Following the synthesis method of intermediate I-1, I-1-2 was replaced with I-3-2 to obtain intermediate I-3 with a yield of 56.7% and MS(ASAP) = 472.

[0165] The synthetic route for intermediate I-4 is as follows:

[0166]

[0167] Synthesis of intermediate I-4:

[0168] Following the synthesis method of intermediate I-1, I-1-2 was replaced with I-3-2 and I-1-3 was replaced with I-4-1 to obtain intermediate I-4 with a yield of 50.3% and MS(ASAP) = 475.

[0169] The synthetic route for intermediate I-5 is as follows:

[0170]

[0171] Synthesis of intermediate I-5:

[0172] Synthesis of intermediate I-5-2: Following the synthesis method of intermediate I-1-2, I-1-1 was replaced with I-5-1 to obtain intermediate I-5-2 with a yield of 73.3% and MS(ASAP) = 245.

[0173] Synthesis of intermediate I-5: Following the synthesis method of intermediate I-1, I-1-2 was replaced with I-5-2 to obtain intermediate I-5 with a yield of 43.1% and MS(ASAP) = 483.

[0174] The synthetic route for intermediate I-6 is as follows:

[0175]

[0176] Synthesis of intermediate I-6:

[0177] Synthesis of intermediate I-6-2: Following the synthesis method of intermediate I-1-2, I-1-1 was replaced with I-6-1 to obtain intermediate I-6-2 with a yield of 71.8% and MS(ASAP) = 259.

[0178] Synthesis of intermediate I-6: Following the synthesis method of intermediate I-1, I-1-2 was replaced with I-6-2 to obtain intermediate I-6 with a yield of 41.5% and MS(ASAP) = 497.

[0179] The synthetic route for intermediate I-7 is as follows:

[0180]

[0181] Synthesis of intermediate I-7:

[0182] Synthesis of intermediate I-7-2: Following the synthesis method of intermediate I-1-2, I-1-1 was replaced with I-7-1 to obtain intermediate I-7-2 with a yield of 76.2% and MS(ASAP) = 273.

[0183] Synthesis of intermediate I-7: Following the synthesis method of intermediate I-1, I-1-2 was replaced with I-7-2 to obtain intermediate I-7 with a yield of 40.3% and MS(ASAP) = 511.

[0184] The synthetic route for intermediate I-8 is as follows:

[0185]

[0186] Synthesis of intermediate I-8:

[0187] Following the synthesis method of intermediate I-1, I-1-2 was replaced with I-7-2 and I-1-3 was replaced with I-2-1 to obtain intermediate I-8 with a yield of 46.7% and MS(ASAP) = 511.

[0188] The synthetic route for intermediate I-9 is as follows:

[0189]

[0190] Synthesis of intermediate I-9:

[0191] Following the synthesis method of intermediate I-1, I-1-3 was replaced with I-9-1 to obtain intermediate I-9 with a yield of 63.5% and MS(ASAP) = 497.

[0192] The synthetic route for intermediate I-10 is as follows:

[0193]

[0194] Synthesis of intermediate I-10:

[0195] Synthesis of intermediate I-10-2: Following the synthesis method of intermediate I-1-2, I-1-1 was replaced with I-10-1 to obtain intermediate I-10-2 with a yield of 66.7% and MS(ASAP) = 307.

[0196] Synthesis of intermediate I-10: Following the synthesis method of intermediate I-1, I-1-2 was replaced with I-10-2 to obtain intermediate I-10 with a yield of 61.0% and MS(ASAP) = 545.

[0197] The synthetic route for intermediate I-11 is as follows:

[0198]

[0199] Synthesis of intermediate I-11:

[0200] Synthesis of intermediate I-11-2: Following the synthesis method of intermediate I-1-2, p-chlorophenylboronic acid was replaced with I-11-1 to obtain intermediate I-11-2 with a yield of 70.1% and MS (ASAP) = 397.

[0201] Synthesis of intermediate I-11: Following the synthesis method of intermediate I-1, I-1-2 was replaced with I-11-2 to obtain intermediate I-11 with a yield of 52.8% and MS(ASAP) = 635.

[0202] The synthetic route for intermediate I-12 is as follows:

[0203]

[0204] Synthesis of intermediate I-12:

[0205] Following the synthesis method of intermediate I-1, I-1-3 was replaced with I-12-1 to obtain intermediate I-12 with a yield of 66.7% and MS(ASAP) = 468.

[0206] Example 1

[0207] Organic compound P1 ( Synthesis of )

[0208] The synthetic route for organic compound P1 is as follows:

[0209]

[0210] The specific synthetic steps of organic compound P1 are as follows:

[0211] I-1 (18.8 g, 40 mmol) and P1-1 (12.9 g, 40 mmol) were weighed and placed in a clean three-necked flask. Pd(dba)2 (1%, 0.23 g), X-Phos (0.38 g, 0.8 mmol), sodium tert-butoxide (7.7 g, 80 mmol), and anhydrous toluene (400 mL) were added. The mixture was purged with nitrogen three times and heated to 110 °C for 3 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. The organic compound P1 was obtained by column chromatography with a yield of 81.0% and MS (ASAP) = 754.

[0212] Example 2

[0213] Organic compound P2 ( Synthesis of )

[0214] The synthetic route for organic compound P2 is as follows:

[0215]

[0216] The specific steps for synthesizing organic compound P2 are as follows:

[0217] Following the synthetic method of organic compound P1, P1-1 was replaced with P2-1 to obtain organic compound P2 with a yield of 72.2% and MS(ASAP) = 718.

[0218] Example 3

[0219] Organic compound P3 ( Synthesis of )

[0220] The synthetic route for organic compound P3 is as follows:

[0221]

[0222] The specific steps for synthesizing organic compound P3 are as follows:

[0223] Following the synthetic method of organic compound P1, P1-1 was replaced with P3-1 to obtain organic compound P3 with a yield of 79.5% and MS(ASAP) = 794.

[0224] Example 4

[0225] Organic compound P4 ( Synthesis of )

[0226] The synthetic route for organic compound P4 is as follows:

[0227]

[0228] The specific steps for synthesizing organic compound P4 are as follows:

[0229] Following the synthetic method for organic compound P1, P1-1 was replaced with P4-1 to obtain organic compound P4 with a yield of 81.3% and MS(ASAP) = 728.

[0230] Example 5

[0231] Organic compound P5 ( Synthesis of )

[0232] The synthetic route for organic compound P5 is as follows:

[0233]

[0234] The specific steps for synthesizing organic compound P5 are as follows:

[0235] Following the synthetic method of organic compound P1, P1-1 was replaced with P5-1 to obtain organic compound P5 with a yield of 68.7% and MS(ASAP) = 734.

[0236] Example 6

[0237] Organic compound P6 ( Synthesis of )

[0238] The synthetic route for organic compound P6 is as follows:

[0239]

[0240] The specific synthetic steps of organic compound P6 are as follows:

[0241] Following the synthetic method for organic compound P1, P1-1 was replaced with P6-1 to obtain organic compound P6 with a yield of 73.0% and MS(ASAP) = 754.

[0242] Example 7

[0243] Organic compound P7 ( Synthesis of )

[0244] The synthetic route for organic compound P7 is as follows:

[0245]

[0246] The specific synthetic steps of organic compound P7 are as follows:

[0247] Following the synthetic method for organic compound P1, P1-1 was replaced with P7-1 to obtain organic compound P7 with a yield of 62.9% and MS (ASAP) = 778.

[0248] Example 8

[0249] Organic compound P8 ( Synthesis of )

[0250] The synthetic route for organic compound P8 is as follows:

[0251]

[0252] The specific synthetic steps of organic compound P8 are as follows:

[0253] Following the synthetic method of organic compound P1, P1-1 was replaced with P8-1 to obtain organic compound P8 with a yield of 69.4% and MS(ASAP) = 824.

[0254] Example 9

[0255] Organic compound P9 ( Synthesis of )

[0256] The synthetic route for organic compound P9 is as follows:

[0257]

[0258] The specific synthetic steps of organic compound P9 are as follows:

[0259] Following the synthetic method of organic compound P1, P1-1 was replaced with P9-1 to obtain organic compound P9 with a yield of 78.1% and MS(ASAP) = 834.

[0260] Example 10

[0261] Organic compound P10 ( Synthesis of )

[0262] The synthetic route for organic compound P10 is as follows:

[0263]

[0264] The specific synthetic steps of organic compound P10 are as follows:

[0265] Following the synthetic method of organic compound P1, P1-1 was replaced with P10-1 and I-1 was replaced with I-2 to obtain organic compound P10 with a yield of 70.8% and MS (ASAP) = 754.

[0266] Example 11

[0267] Organic compound P11 ( Synthesis of )

[0268] The synthetic route for organic compound P11 is as follows:

[0269]

[0270] The specific synthetic steps of organic compound P11 are as follows:

[0271] Following the synthetic method of organic compound P1, P1-1 was replaced with P11-1 and I-1 was replaced with I-2 to obtain organic compound P11 with a yield of 56.2% and MS (ASAP) = 794.

[0272] Example 12

[0273] Organic compound P12 ( Synthesis of )

[0274] The synthetic route for the organic compound P12 is as follows:

[0275]

[0276] The specific synthetic steps of organic compound P12 are as follows:

[0277] Following the synthetic method of organic compound P1, P1-1 was replaced with P12-1 and I-1 was replaced with I-2 to obtain organic compound P12 with a yield of 71.0% and MS (ASAP) = 728.

[0278] Example 13

[0279] Organic compound P13 ( Synthesis of )

[0280] The synthetic route for organic compound P13 is as follows:

[0281]

[0282] The specific synthetic steps of organic compound P13 are as follows:

[0283] Following the synthetic method of organic compound P1, P1-1 was replaced with P13-1 and I-1 was replaced with I-2 to obtain organic compound P13 with a yield of 57.1% and MS (ASAP) = 754.

[0284] Example 14

[0285] Organic compound P14 ( Synthesis of )

[0286] The synthetic route for organic compound P14 is as follows:

[0287]

[0288] The specific synthetic steps of organic compound P14 are as follows:

[0289] Following the synthetic method of organic compound P1, P1-1 was replaced with P14-1 and I-1 was replaced with I-3 to obtain organic compound P14 with a yield of 76.7% and MS(ASAP) = 797.

[0290] Example 15

[0291] Organic compound P15 ( Synthesis of )

[0292] The synthetic route for organic compound P15 is as follows:

[0293]

[0294] The specific synthetic steps of organic compound P15 are as follows:

[0295] Following the synthetic method of organic compound P1, P1-1 was replaced with P10-1 and I-1 was replaced with I-4 to obtain organic compound P15 with a yield of 77.8% and MS (ASAP) = 760.

[0296] Example 16

[0297] Organic compound P16 ( Synthesis of )

[0298] The synthetic route for organic compound P16 is as follows:

[0299]

[0300] The specific synthetic steps of organic compound P16 are as follows:

[0301] Following the synthetic method for organic compound P1, P1-1 was replaced with P16-1 to obtain organic compound P16 with a yield of 68.3% and MS (ASAP) = 812.

[0302] Example 17

[0303] Organic compound P17 ( Synthesis of )

[0304] The synthetic route for organic compound P17 is as follows:

[0305]

[0306] The specific synthetic steps of organic compound P17 are as follows:

[0307] Following the synthetic method of organic compound P1, I-1 was replaced with I-5 and P1-1 was replaced with P17-1 to obtain organic compound P17 with a yield of 74.3% and MS (ASAP) = 808.

[0308] Example 18

[0309] Organic compound P18 ( Synthesis of )

[0310] The synthetic route for organic compound P18 is as follows:

[0311]

[0312] The specific synthetic steps of organic compound P18 are as follows:

[0313] Following the synthetic method of organic compound P1, I-1 was replaced with I-6 and P1-1 was replaced with P11-1 to obtain organic compound P18 with a yield of 71.0% and MS (ASAP) = 822.

[0314] Example 19

[0315] Organic compound P19 ( Synthesis of )

[0316] The synthetic route for organic compound P19 is as follows:

[0317]

[0318] The specific synthetic steps of organic compound P19 are as follows:

[0319] Following the synthetic method of organic compound P1, I-1 was replaced with I-7 and P1-1 was replaced with P19-1 to obtain organic compound P19 with a yield of 66.7% and MS (ASAP) = 961.

[0320] Example 20

[0321] Organic compound P20 ( Synthesis of )

[0322] The synthetic route for organic compound P20 is as follows:

[0323]

[0324] The specific synthetic steps of organic compound P20 are as follows:

[0325] Following the synthetic method of organic compound P1, I-1 was replaced with I-8 and P1-1 was replaced with P10-1 to obtain organic compound P20 with a yield of 75.1% and MS (ASAP) = 796.

[0326] Example 21

[0327] Organic compound P21 ( Synthesis of )

[0328] The synthetic route for organic compound P21 is as follows:

[0329]

[0330] The specific synthetic steps of organic compound P21 are as follows:

[0331] Following the synthetic method of organic compound P1, I-1 was replaced with I-9 and P1-1 was replaced with P11-1 to obtain organic compound P21 with a yield of 65.8% and MS (ASAP) = 822.

[0332] Example 22

[0333] Organic compound P22 ( Synthesis of )

[0334] The synthetic route for organic compound P22 is as follows:

[0335]

[0336] The specific synthetic steps of organic compound P22 are as follows:

[0337] Following the synthetic method of organic compound P1, I-1 was replaced with I-10 and P1-1 was replaced with P22-1 to obtain organic compound P22 with a yield of 83.3% and MS (ASAP) = 808.

[0338] Example 23

[0339] Organic compound P23 ( Synthesis of )

[0340] The synthetic route for organic compound P23 is as follows:

[0341]

[0342] The specific synthetic steps of organic compound P23 are as follows:

[0343] Following the synthetic method of organic compound P1, I-1 was replaced with I-10 and P1-1 was replaced with P23-1 to obtain organic compound P23 with a yield of 82.7% and MS (ASAP) = 844.

[0344] Example 24

[0345] Organic compound P24 ( Synthesis of )

[0346] The synthetic route for organic compound P24 is as follows:

[0347]

[0348] The specific synthetic steps of organic compound P24 are as follows:

[0349] Following the synthetic method of organic compound P1, I-1 was replaced with I-11 and P1-1 was replaced with P24-1 to obtain organic compound P24 with a yield of 67.9% and MS (ASAP) = 845.

[0350] Example 25

[0351] Organic compound P25 ( Synthesis of )

[0352] The synthetic route for organic compound P25 is as follows:

[0353]

[0354] The specific synthetic steps of organic compound P25 are as follows:

[0355] Following the synthetic method of organic compound P1, I-1 was replaced with I-12 and P1-1 was replaced with P17-1 to obtain organic compound P25 with a yield of 86.1% and MS (ASAP) = 793.

[0356] An exemplary manufacturing process for the light-emitting element provided by the present invention is shown in the following exemplary embodiment 26.

[0357] Example 26

[0358] 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. The specific fabrication steps are as follows:

[0359] a. Cleaning of ITO anode: Ultrasonic cleaning with deionized water, acetone, and isopropanol for 15 minutes, followed by treatment in a plasma cleaner for 5 minutes to improve electrode work function;

[0360] b. Formation of hole injection layer: Hole injection material HATCN is deposited on the ITO anode by vacuum evaporation to form a hole injection layer with a thickness of 30nm;

[0361] c. Forming a hole transport layer: A hole transport material is deposited on the hole injection layer by vacuum evaporation to form a hole transport layer with a thickness of 60nm;

[0362] d. Forming a light-emitting auxiliary layer: A light-emitting auxiliary layer with a thickness of 10 nm is formed by evaporating the light-emitting auxiliary material Prime on the hole transport layer;

[0363] e. Forming the light-emitting layer: A light-emitting layer is deposited on the light-emitting auxiliary layer. BH is used as the host material and BD is used as the dopant material. The mass ratio of BH to BD is 98:2 and the thickness of the light-emitting layer is 25nm.

[0364] f. Forming an electron transport layer: An electron transport layer with a thickness of 30 nm is formed by vacuum evaporation of electron transport materials ET and Liq (ET and Liq in a mass ratio of 5:5) on the organic light-emitting layer.

[0365] g. Forming an electron injection layer: An electron injection layer with a thickness of 1 nm is formed on the electron transport layer by vacuum evaporation of electron injection material Liq.

[0366] h. Forming the cathode layer: Al is deposited on the electron injection layer by vacuum evaporation to obtain an Al cathode with a thickness of 100 nm;

[0367] i. Packaging: The device is encapsulated in a nitrogen glove box using UV-cured resin.

[0368] Specifically, in this embodiment, light-emitting elements 1 to 25 and contrast elements 1 to 3 are obtained through the above steps. The hole transport materials used in light-emitting elements 1 to 25 are organic compounds P1 to P25, respectively, and the hole transport materials used in contrast elements 1 to 3 are Ref1, Ref2, and Ref3, respectively.

[0369] Specifically, HATCN, Prime, BH, BD, ET, Liq, Ref1, Ref2, and Ref3 are all commercially available or synthesized using known synthetic methods and existing raw materials. The chemical structural formulas of the above compounds are as follows:

[0370]

[0371] In this embodiment, current-voltage (JV) characteristic tests were performed on light-emitting elements 1 to 25 and comparison elements 1 to 3, and the results were obtained for each light-emitting element and comparison element at a current density of 10 mA / cm². 2 The voltage, the time required for the brightness to drop to 95% of the initial brightness @1000 nits (relative lifetime), and the relative external quantum efficiency are shown in Table 1.

[0372] Table 1: Performance data of light-emitting elements 1 to 25 and contrast elements 1 to 3

[0373] 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％ Comparison element 1 4.8 1.0 100％ Comparison element 2 4.5 0.9 106％ Comparison element 3 4.4 0.7 101％

[0374] As shown in Table 1, the light-emitting elements 1 to 25 obtained by using organic compounds P1 to P25 as hole transport materials in the hole transport layer of the present invention have significantly improved luminous efficiency and lifetime compared with the comparative elements 1 to 3. Specifically, the luminous efficiency of light-emitting elements 1 to 25 is more than 111% compared with the comparative element 1, and the lifetime of light-emitting elements 1 to 25 is more than 1.1 times that of the comparative element 1.

[0375] Among them, when organic compounds P1 to P25 are used as hole transport materials, compared with Ref1 and Ref2 as hole transport materials, organic compounds P1 to P25 fix the linkage site of the aromatic amino group on the fluorene group at the 2 position, making the highest occupied molecular orbital (HOMO) energy level of organic compounds P1 to P25 more suitable, reducing the hole transport barrier, and thus improving the carrier transport performance in the light-emitting element.

[0376] When organic compounds P1 to P25 are used as hole transport materials, compared with Ref3 as hole transport material, organic compounds P1 to P25 introduce a large steric hindrance group at position 9 of the fluorene group, which enhances the film-forming properties of organic compounds P1 to P25 and obtains higher thermal stability while improving the carrier transport performance in the light-emitting element.

[0377] The light-emitting element disclosed in this invention improves hole transport performance and thermal stability by using the organic compound, which connects an aromatic amine group to the 2-position of the fluorene group and introduces a highly distorted sterically hindered group at the 9-position of the fluorene group. This improves the luminous efficiency of the light-emitting element and extends its service life.

[0378] The present invention also discloses a display panel, which includes any of the light-emitting elements described above.

[0379] The display panel further includes an array substrate located on one side of the light-emitting element, and an encapsulation layer located on the side of the light-emitting element away from the array substrate and covering the light-emitting element. The display panel also includes a polarizer layer located on the side of the encapsulation layer away from the light-emitting element, and a cover plate layer located on the side of the polarizer layer away from the light-emitting element. The polarizer layer can be replaced by a color filter layer, which may include multiple color resists and black matrices located on both sides of the color resists.

[0380] The display panel disclosed in this embodiment of the invention improves hole transport performance and thermal stability by using an organic compound with the structure shown in general formula (1) in the light-emitting element, thereby improving the luminous efficiency of the display panel and extending its service life.

[0381] This invention discloses an organic compound, a light-emitting element, and a display panel. The organic compound has a structure as shown in general formula (1): The present invention uses an organic compound having the structure shown in general formula (1), which connects an aromatic amine group to the 2 position of the fluorenyl group and introduces a highly distorted sterically hindered group at the 9 position of the fluorenyl group, thereby effectively improving hole transport performance and thermal stability, thereby improving the luminous efficiency of the light-emitting element and extending the service life of the light-emitting element.

[0382] The organic compound, light-emitting element, and display panel provided in the embodiments of the present invention have been described in detail above. Specific examples have been used to illustrate the principles and implementation methods of the present invention. The description of the above embodiments is only for the purpose of helping to understand the method and core ideas of the present invention. At the same time, for those skilled in the art, there will be changes in the specific implementation methods and application scope based on the ideas of the present invention. Therefore, the content of this specification should not be construed as a limitation of the present invention.

Claims

1. An organic compound, characterized in that, The organic compound has a structure as shown in any of general formulas (1-1) to (1-2): ； Among them, Ar 1 Ar 2 Each group is independently selected from any one of the following groups: ； Where X is selected from N, C or CR 6 The X group connected to the adjacent group is selected from C; Y is selected from O, S, or CR. 8 R 9 ; R 6 Each time it appears, it is independently selected from hydrogen, deuterium, unsubstituted straight-chain alkyl groups having 1 to 20 carbon atoms, unsubstituted cyclic alkyl groups having 3 to 10 carbon atoms, phenyl groups, etc. Or adamantyl; R 8 R 9 Each time it appears, it is independently selected from hydrogen, deuterium, and unsubstituted straight-chain alkyl groups having 1 to 20 carbon atoms; R 1 R 2 Each time it appears, it is independently selected from unsubstituted straight-chain alkyl groups having 1 to 20 carbon atoms or unsubstituted branched alkyl groups having 3 to 20 carbon atoms; R 3 Each time it appears, it is selected from hydrogen or deuterium; R 4 Each time it appears, it is selected from hydrogen, deuterium or unsubstituted straight-chain alkyl groups having 1 to 20 carbon atoms; R 5 Each time it appears, it is selected from hydrogen, deuterium, unsubstituted phenyl or unsubstituted dibenzofuranyl; L1 and L2 are independently selected from single bonds, phenyl groups, or naphthyl groups, respectively; a is any integer from 0 to 4; b is any integer from 0 to 8; c is any integer from 0 to 7.

2. The organic compound according to claim 1, characterized in that, R 6 Each time it appears, it is independently selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, or phenyl; R 8 R 9 Each time it appears, it is independently selected from hydrogen, methyl, or ethyl.

3. The organic compound according to claim 1 or 2, characterized in that, R 1 R 2 Each time it appears, it is independently selected from unsubstituted straight-chain alkyl groups having 1 to 5 carbon atoms or unsubstituted branched alkyl groups having 3 to 10 carbon atoms; R 4 Each time it appears, it is independently selected from hydrogen, deuterium, or unsubstituted straight-chain alkyl groups having 1 to 5 carbon atoms.

4. The organic compound according to claim 3, characterized in that, R 1 R 2 Each time it appears, it is independently selected from unsubstituted straight-chain alkyl groups having 1 to 3 carbon atoms; R 4 Each time it appears, it is independently selected from hydrogen, deuterium, or an unsubstituted straight-chain alkyl group having 1 to 3 carbon atoms.

5. The organic compound according to claim 3, characterized in that, R 1 R 2 Each time it appears, it is independently selected from tert-butyl.

6. An organic compound, characterized in that, The organic compound is selected from any one of the following compounds: 。 7. A light-emitting element, characterized in that, include: 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; The material of the organic functional layer includes at least one organic compound as described in any one of claims 1 to 6.

8. The light-emitting element according to claim 7, characterized in that, The organic functional layer includes a light-emitting layer, a hole transport layer located between the light-emitting layer and the first electrode, a light-emitting auxiliary layer located between the hole transport layer and the light-emitting layer, a hole injection layer located between the hole transport layer and the first electrode, an electron transport layer located between the light-emitting layer and the second electrode, and an electron injection layer located between the electron transport layer and the second electrode. The hole transport layer comprises at least one organic compound as described in any one of claims 1 to 6.

9. A display panel, characterized in that, Includes the light-emitting element as described in claim 7 or 8.

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