Organic compounds and organic light emitting diodes comprising the same

Abstract

The organic compound represented by Chemical Formula A according to the present application can achieve excellent hole transport properties. Also, the hole transport layer or the hole transport auxiliary layer of the organic light emitting diode according to the present application, which contains the organic compound represented by Chemical Formula A according to the present application, can improve the driving voltage, efficiency, and lifespan characteristics of the organic light emitting diode.

Description

Technical Field

[0001] This invention relates to an organic compound and an organic light-emitting diode comprising the same. Background Technology

[0002] Compared with other flat panel display devices such as liquid crystal displays (LCDs), plasma display panels (PDPs), and field emission displays (FEDs), organic light-emitting diodes (OLEDs) have many advantages in terms of simple structure and manufacturing process. They also have high brightness and excellent viewing angle characteristics, as well as fast response speed and low driving voltage. Therefore, they are being actively developed and commercialized as light sources for flat panel displays such as wall-mounted TVs (TVs) or for backlighting, illumination, and advertising boards.

[0003] An organic light-emitting diode (OLED) consists of an organic layer between two electrodes. It is a device that uses the principle that electrons and holes are injected into the light-emitting layer from the two electrodes respectively. When electrons and holes combine, they generate excitons. When the generated excitons descend from the excited state to the ground state, they emit light.

[0004] Organic light-emitting diodes (OLEDs) may include at least one light-emitting layer. Typically, OLEDs with multiple light-emitting layers include light-emitting layers that emit light with different peak wavelengths, and a specific color is achieved by combining light with different peak wavelengths.

[0005] Such organic light-emitting diodes (OLEDs) can be divided into bottom-emitting devices and top-emitting devices. Bottom-emitting devices use a reflective second electrode (cathode) to emit light emitted from the light-emitting layer towards the semi-transparent or transparent first electrode (anode). Conversely, top-emitting devices use a reflective first electrode to emit light emitted from the light-emitting layer and reflected from the first electrode towards the transparent second electrode, which is the direction in which the thin-film transistor is driven.

[0006] Existing technical documents

[0007] Patent documents

[0008] Existing patent document 1: WO2011-059099A1 (published on May 19, 2011)

[0009] Existing patent document 2: WO2017-022727A1 (published on 2017.02.09)

[0010] Existing patent document 3: WO2021-096228A1 (published on 2021.05.20) Summary of the Invention

[0011] Technical issues

[0012] The purpose of this invention is to provide a novel organic compound and an organic light-emitting diode comprising the same.

[0013] Apart from the technical issues mentioned above, technical issues not specifically mentioned will be explained through embodiments of the present invention.

[0014] The objectives of this invention are not limited to those mentioned above. Other objectives and advantages of the invention not mentioned can be understood through the following description, and will become more apparent through embodiments of the invention. Furthermore, it will be understood that the objectives and advantages of the invention can be achieved through the means and combinations thereof shown in the claims.

[0015] Technical solution

[0016] According to one embodiment of the present invention, an organic compound represented by the following chemical formula A can be provided, wherein the definition of the following chemical formula A is the same as that described in this specification and the scope of the claims.

[0017] Chemical formula A:

[0018]

[0019] In the chemical formula A,

[0020] L is selected from the group consisting of arylene groups with 6 to 30 carbon atoms (either single-bonded, substituted or unsubstituted) and heteroarylene groups with 3 to 60 carbon atoms (either substituted or unsubstituted).

[0021] Ar is an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heteroaryl group with 3 to 60 substituted or unsubstituted carbon atoms.

[0022] R1 to R 25 They may be the same as or different from each other, and each independently consists of one selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl groups of 1 to 30, substituted or unsubstituted aryl groups of 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups of 3 to 60 carbon atoms.

[0023] n1 and n2 may be the same or different from each other, and each is an independent integer from 0 to 5.

[0024] n3 is an integer from 0 to 3.

[0025] n4 is an integer from 0 to 4.

[0026] In L, Ar and R1 to R 25When substituted, the substituents may be the same or different from each other, and can be selected from deuterium, cyano, trifluoromethyl, nitro, halogen group, hydroxyl, trimethylsilyl (TMS), alkyl with 1 to 30 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, alkenyl with 2 to 30 carbon atoms, cycloalkenyl with 3 to 20 carbon atoms, alkynyl with 2 to 30 carbon atoms, cycloalkynyl with 3 to 20 carbon atoms, aryl with 6 to 30 carbon atoms, aralkyl with 7 to 30 carbon atoms, heteroaryl with 3 to 60 carbon atoms, heteroaryl with 4 to 60 carbon atoms, amine The substituents are one or more of the group consisting of alkylamino, alkylamino with 1 to 30 carbon atoms, arylalkylamino with 7 to 30 carbon atoms, arylamino with 6 to 30 carbon atoms, heteroarylamino with 3 to 60 carbon atoms, silyl, alkylsilyl with 1 to 30 carbon atoms, arylsilyl with 6 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, aryloxy with 6 to 30 carbon atoms, alkylthio with 1 to 30 carbon atoms, and arylthio with 6 to 30 carbon atoms, wherein when there are multiple substituents, the substituents may be the same or different from each other.

[0027] *a, *b1, and *b2 are different from each other and represent the bonding sites on the phenylene group, while *c represents the bonding site on the phenanthrene group.

[0028] One of R5 to R9 represents a single bond that bonds with *a.

[0029] R 10 To R 15 One of them represents a single bond that bonds with *b1.

[0030] R 10 To R 15 Another representation in the text is a single bond bonded to *b2.

[0031] R 16 To R 25 One of them represents a single bond that bonds with *c.

[0032] According to an embodiment of the present invention, an organic light-emitting diode (OLED) can be provided, the OLED comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic layers located inside the first electrode and the second electrode, wherein at least one of the organic layers comprises the organic compound represented by chemical formula A.

[0033] The effects of the invention

[0034] The organic compound represented by chemical formula A of the present invention can achieve excellent hole transport characteristics.

[0035] Furthermore, one or more of the hole transport layer and hole transport auxiliary layer of the organic light-emitting diode of the present invention contain the organic compound represented by chemical formula A of the present invention, thereby improving the driving voltage, external quantum efficiency and lifetime characteristics of the organic light-emitting diode.

[0036] Furthermore, when the organic compound represented by chemical formula A of the present invention is used as the hole transport auxiliary layer material, it can have an appropriate energy level as a hole transport auxiliary layer, which plays the role of transporting holes from the hole transport layer to the light-emitting layer and blocking electrons from the light-emitting layer.

[0037] Furthermore, the organic light-emitting diode of the present invention includes a hole transport layer and / or a hole transport auxiliary layer comprising an organic compound represented by chemical formula A of the present invention, which can excellently achieve the color coordinates targeted by the light-emitting layer even when combined with a light-emitting layer of any color.

[0038] The effects of this invention are not limited to those described above. Those skilled in the art will clearly understand other effects not mentioned through the full description in this specification. The above and other effects will be described in detail below. Detailed Implementation

[0039] The foregoing objectives, features, and advantages will be described in detail below, and those skilled in the art to which this invention pertains can easily implement the technical ideas of this invention.

[0040] In describing this specification, detailed descriptions of well-known technologies related to this invention will be omitted when it is determined that such descriptions may unnecessarily obscure the essence of the invention.

[0041] In this specification, when structural elements such as "including," "having," "forming," "setting," and "possessing" are mentioned, other parts may be added unless limited by "only." Unless otherwise expressly stated, the use of the singular to express structural elements includes the plural case.

[0042] In this specification, when interpreting structural elements, even if not explicitly stated, it is interpreted as including the range of error.

[0043] In this specification, when referring to the “upper (or lower) part” of a structural element or the “upper (or lower) part” of a structural element having any structure, it not only indicates that the arbitrary structure is arranged in contact with the upper (or lower) part of the structural element, but also indicates that there are other structures intervening between the structural element and the arbitrary structure arranged on the upper (or lower) part of the structural element.

[0044] The expressions “at least one of a, b and c” and “of a, b or c” as used in this specification may include “a alone”, “b alone”, “c alone”, “a and b”, “a and c”, “b and c” or “all of a, b and c”.

[0045] The term "halogen group" as used in this specification includes fluorine, chlorine, bromine, and iodine.

[0046] As used in this specification, the term "alkyl" refers to both straight-chain alkyl radicals and branched-chain alkyl radicals. Unless otherwise specified, an alkyl group contains 1 to 30 carbon atoms and may include, but is not limited to, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl, hexyl, etc. Furthermore, alkyl groups may be substituted in any way.

[0047] As used in this specification, the term "cycloalkyl" refers to a cyclic alkyl radical. Unless otherwise specified, a cycloalkyl group contains 3 to 20 carbon atoms and may include, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, etc. Furthermore, the cycloalkyl group may be substituted in any way.

[0048] As used in this specification, the term "alkenyl" refers to a straight-chain alkenyl radical and a branched alkenyl radical having one or more carbon-carbon double bonds. Unless otherwise specified, an alkenyl group contains 2 to 30 carbon atoms and may include, but is not limited to, vinyl, allyl, isopropenyl, 2-butenyl, etc. Furthermore, the alkenyl group can be arbitrarily substituted.

[0049] As used in this specification, the term "cycloalkenyl" refers to a cyclic alkenyl radical. Unless otherwise specified, a cycloalkenyl radical contains 3 to 20 carbon atoms, and furthermore, the cycloalkenyl radical can be arbitrarily substituted.

[0050] As used in this specification, the term "alkynyl" refers to a straight-chain alkynyl radical and a branched alkynyl radical having one or more carbon-carbon triple bonds. Unless otherwise specified, an alkynyl radical contains 2 to 30 carbon atoms and may include, but is not limited to, ethynyl or 2-propynyl. Furthermore, the alkynyl radical can be arbitrarily substituted.

[0051] As used in this specification, the term "cycloynyl" refers to a cyclic ynyl radical. Unless otherwise specified, a cycloynyl radical contains 3 to 20 carbon atoms, and furthermore, the cycloynyl radical can be arbitrarily substituted.

[0052] The terms “aralkyl” or “arylalkyl” used in this specification may be used interchangeably and refer to an alkyl group having an aromatic group as a substituent. Furthermore, aralkyl (arylalkyl) may be substituted in any way.

[0053] The terms "aryl" or "aromatic group" used in this specification have the same meaning, and aryl includes monocyclic and polycyclic groups. Polycyclic groups can include "fused rings" consisting of two or more rings shared by two adjacent rings, with two carbon atoms. Furthermore, they can also include forms where two or more rings are simply linked or fused together. Unless otherwise specified, aryl groups contain 6 to 30 carbon atoms and can include, but are not limited to, phenyl, naphthyl, phenanthryl, anthraceneyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, etc. Furthermore, aryl groups can be substituted in any way.

[0054] The terms "heteroaryl" or "heteroaromatic group" used in this specification have the same meaning, and heteroaryl includes monocyclic and polycyclic groups. Polycyclic groups can include "fused rings" of two or more rings shared by two adjacent rings as two carbon atoms or heteroatoms. Furthermore, they can also include forms in which two or more rings are simply connected or fused together. Unless otherwise specified, the heteroaryl group contains 3 to 60 carbon atoms. In this case, one or more carbon atoms in the ring are replaced by heteroatoms such as oxygen (O), nitrogen (N), sulfur (S), or selenium (Se). It can include 6-membered monocyclic rings, such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings, such as phenoxthiayl, indoleazinyl, indoleyl, purine, quinolinyl, isoquinolinyl, benzoxazolyl, benzothiazolyl, dibenzoxazolyl, dibenzothiazolyl, benzimidazolyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, carbazolyl, phenylcarbazolyl, and 9-phenylcarbazolyl; and 2-furanyl, N-imidazolyl, 2-isooxazolyl, 2-pyridinyl, and 2-pyrimidinyl, but is not limited thereto. Furthermore, the heteroaryl group can be arbitrarily substituted.

[0055] As used in this specification, the term "heterocyclic group" refers to a group in which one or more carbon atoms constituting aryl, cycloalkyl, cycloalkenyl, cycloalkynyl, aralkyl, arylamino, etc., are replaced by heteroatoms such as oxygen (O), nitrogen (N), and sulfur (S). Referring to the above definition, it includes heteroaryl, heterocycloalkyl, heterocycloalkenyl, heterocycloalkynyl, heteroaromaticyl, heteroaromaticamino, etc. Furthermore, heterocyclic groups can be arbitrarily substituted.

[0056] Unless otherwise specified, the term "carbon ring" as used in this specification may be used as a term that simultaneously includes "cycloalkyl", "cycloalkenyl", "cycloynyl" as alicyclic cyclic groups and "aryl (aromatic group)" as an aromatic cyclic group.

[0057] The terms “heteroalkyl,” “heteroalkenyl,” “heteroynyl,” and “heteroaryl” used in this specification refer to a form in which one or more carbon atoms constituting the carbon atom are replaced by heteroatoms such as oxygen (O), nitrogen (N), and sulfur (S). Furthermore, heteroalkyl, heteroalkenyl, heteroynyl, and heteroaryl can be arbitrarily substituted.

[0058] As used in this specification, the terms "alkylamino", "arylalkylamino", "arylamino", and "heteroarylamino" refer to amino groups (or amino groups) that are substituted by the alkyl, arylalkyl, aryl, or heteroaryl groups, and simultaneously include primary, secondary, or tertiary amino groups (or amino groups). Furthermore, alkylamino, arylalkylamino, arylamino, and heteroarylamino groups can be substituted in any way.

[0059] The terms “alkylsilyl”, “arylsilyl”, “alkoxy”, “aryloxy”, “alkathio”, and “arylthio” used in this specification refer to the substitution of silyl, oxy, and thio groups by the alkyl and aryl groups, respectively. Furthermore, alkylsilyl, arylsilyl, alkoxy, aryloxy, alkathio, and arylthio can be substituted in any way.

[0060] As used in this specification, the terms "arylene," "arylalkylene," "heteroarylene," and "heteroarylalkylene" refer to the aryl, aralkyl, heteroaryl, and heteroaryl groups each comprising one or more divalent substituents. Furthermore, the arylene, arylalkylene, heteroarylene, and heteroarylalkylene groups may be substituted in any way.

[0061] As used in this specification, the term "substitution" means replacing hydrogen (H) atoms bonded to carbon atoms, nitrogen atoms, etc., of the compounds of the present invention with substituents other than hydrogen. In the case of multiple substituents, the substituents may be the same as or different from each other.

[0062] The substituents may be independently selected from deuterium, cyano, trifluoromethyl, nitro, halogen group, hydroxyl, trimethylsilyl (TMS), alkyl with 1 to 30 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, alkenyl with 2 to 30 carbon atoms, cycloalkenyl with 3 to 20 carbon atoms, alkynyl with 2 to 30 carbon atoms, cycloalkynyl with 3 to 20 carbon atoms, aryl with 6 to 30 carbon atoms, aralkyl with 7 to 30 carbon atoms, heteroaryl with 3 to 60 carbon atoms, and carbon atom. Among the following groups: heteroaryl, amino, alkylamino, arylalkylamino, arylalkylamino, arylamino, heteroarylamino, silyl, alkylsilyl, arylsilyl, alkoxy, aryloxy, alkathio, alkylthio, and arylthio.

[0063] Unless otherwise specified, the objects and substituents defined in this specification may be the same or different.

[0064] Unless otherwise specified, all units in this specification are in weight (wt). For example, if stated as "%", it means weight percentage (wt%).

[0065] The organic compounds of the present invention and organic light-emitting diodes comprising the thereof will be described in detail below.

[0066] The organic compounds of the present invention can be represented by the following chemical formula A.

[0067] Chemical formula A:

[0068]

[0069] In the chemical formula A,

[0070] L is selected from the group consisting of arylene groups with 6 to 30 carbon atoms (either single-bonded, substituted or unsubstituted) and heteroarylene groups with 3 to 60 carbon atoms (either substituted or unsubstituted).

[0071] Ar is an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heteroaryl group with 3 to 60 substituted or unsubstituted carbon atoms.

[0072] R1 to R 25 They may be the same as or different from each other, and each independently consists of one selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl groups of 1 to 30, substituted or unsubstituted aryl groups of 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups of 3 to 60 carbon atoms.

[0073] n1 and n2 may be the same or different from each other, and each is an independent integer from 0 to 5.

[0074] n3 is an integer from 0 to 3.

[0075] n4 is an integer from 0 to 4.

[0076] In L, Ar and R1 to R 25When substituted, the substituents may be the same or different from each other, and can be selected from deuterium, cyano, trifluoromethyl, nitro, halogen group, hydroxyl, trimethylsilyl (TMS), alkyl with 1 to 30 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, alkenyl with 2 to 30 carbon atoms, cycloalkenyl with 3 to 20 carbon atoms, alkynyl with 2 to 30 carbon atoms, cycloalkynyl with 3 to 20 carbon atoms, aryl with 6 to 30 carbon atoms, aralkyl with 7 to 30 carbon atoms, heteroaryl with 3 to 60 carbon atoms, heteroaryl with 4 to 60 carbon atoms, amine The substituents are one or more of the group consisting of alkylamino, alkylamino with 1 to 30 carbon atoms, arylalkylamino with 7 to 30 carbon atoms, arylamino with 6 to 30 carbon atoms, heteroarylamino with 3 to 60 carbon atoms, silyl, alkylsilyl with 1 to 30 carbon atoms, arylsilyl with 6 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, aryloxy with 6 to 30 carbon atoms, alkylthio with 1 to 30 carbon atoms, and arylthio with 6 to 30 carbon atoms, wherein when there are multiple substituents, the substituents may be the same or different from each other.

[0077] *a, *b1, and *b2 are different from each other and represent the bonding sites on the phenylene group, while *c represents the bonding site on the phenanthrene group.

[0078] One of R5 to R9 represents a single bond that bonds with *a.

[0079] R 10 To R 15 One of them represents a single bond that bonds with *b1.

[0080] R 10 To R 15 Another representation in the text is a single bond bonded to *b2.

[0081] R 16 To R 25 One of them represents a single bond that bonds with *c.

[0082] According to one embodiment of the present invention, L can be a single bond or a substituted or unsubstituted carbon group with 6 to 25 carbon atoms, for example, 6 to 15 carbon atoms, for example, 6 to 12 carbon atoms, for example, an aryl group with 6 to 10 carbon atoms.

[0083] According to one embodiment of the present invention, L can be a single bond or a substituted or unsubstituted phenylene.

[0084] The substituted or unsubstituted phenylene selected as L can be a divalent phenylene with two substituted positions among the 6-position phenylenes capable of substitutional bonding. This can be any of 1,2 (ortho) substitution, 1,3 (meta) substitution, or 1,4 (para) substitution, and can be selected from structures B1 to B3 below (in some compounds of structures B1 to B3 below, * indicates the portion of the compound bonded by a single bond).

[0085]

[0086] According to one embodiment of the present invention, the Ar can be an aryl group with 6 to 25 substituted or unsubstituted carbon atoms, for example, 6 to 15 substituted carbon atoms, for example, 6 to 12 substituted carbon atoms, for example, 6 to 10 substituted carbon atoms, or a heteroaryl group with 3 to 18 substituted or unsubstituted carbon atoms, for example, 3 to 12 substituted carbon atoms, for example, 3 to 9 substituted carbon atoms, for example, 3 to 7 substituted carbon atoms, for example, 3 to 4 substituted carbon atoms.

[0087] According to one embodiment of the present invention, Ar can be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted anthraceneyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dimethylfluorenyl, a substituted or unsubstituted diphenylfluorenyl, a substituted or unsubstituted spirodifluorenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyridazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted phenoxathiolyl, a substituted or unsubstituted indolazinyl, a substituted or unsubstituted indolayl, a substituted or unsubstituted purine, or a substituted or unsubstituted quinolinyl. Substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzoxazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenylcarbazolyl, substituted or unsubstituted 9-phenylcarbazolyl, substituted or unsubstituted 2-furanyl, substituted or unsubstituted N-imidazolyl, substituted or unsubstituted 2-isooxazolyl, substituted or unsubstituted 2-pyridyl, substituted or unsubstituted 2-pyrimidinyl.

[0088] According to one embodiment of the present invention, Ar may be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted dimethylfluorenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiopheneyl, a substituted or unsubstituted carbazoyl, a substituted or unsubstituted phenylcarbazoyl, or a substituted or unsubstituted 9-phenylcarbazoyl.

[0089] According to one embodiment of the present invention, Ar can be one of the substituents represented by M1 to M43 below. In M1 to M45 below, * represents the bonding site.

[0090] According to one embodiment of the present invention, in M1 to M31 below, Dn refers to the number of deuterium substituted in the structure, where n, representing the number of deuterium, is an integer greater than or equal to 0.

[0091] According to an embodiment of the present invention, in formula M1, n is an integer selected from 0 to 5; in formulas M2 to M4, n is an integer selected from 0 to 9; in formulas M5 and M6, n is an integer selected from 0 to 13; in formulas M7 and M8, n is an integer selected from 0 to 7; in formula M9, ​​n is an integer selected from 0 to 9; in formulas M10 to M13, n is an integer selected from 0 to 13; in formulas M14 to M21, n is an integer selected from 0 to 7; in formulas M22 to M28, n is an integer selected from 0 to 12; and in formulas M29 and M30, n is an integer selected from 0 to 8.

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] According to an embodiment of the present invention, R1 to R 25 They can be the same or different from each other, and can be hydrogen or deuterium independently.

[0104] According to one embodiment of the present invention, the chemical formula A can be represented by chemical formula 1 to chemical formula 3.

[0105] Chemical Formula 1:

[0106]

[0107] Chemical formula 2:

[0108]

[0109] Chemical formula 3:

[0110]

[0111] In the chemical formulas 1 to 3,

[0112] L, Ar, R1 to R9, R 11 To R 25 The definitions of n1 to n4 and their substituents are the same as those in the chemical formula A.

[0113] *b2 represents the bonding site on the phenylene group, and *c represents the bonding site on the phenanthrene group.

[0114] R 11 To R 15 One of them represents a single bond that bonds with *b2.

[0115] R 16 To R 25 One of them represents a single bond that bonds with *c.

[0116] According to one embodiment of the present invention, R 13 With R 18 R 14 With R 18 Or R 15 With R 18 Single-key bonding is possible.

[0117] According to one embodiment of the present invention, the chemical formula A may be represented by the following chemical formulas 4 to 12.

[0118] Chemical formula 4:

[0119]

[0120] Chemical formula 5:

[0121]

[0122] Chemical formula 6:

[0123]

[0124] Chemical Formula 7:

[0125]

[0126] Chemical formula 8:

[0127]

[0128] Chemical formula 9:

[0129]

[0130] Chemical Formula 10:

[0131]

[0132] Chemical Formula 11:

[0133]

[0134] Chemical formula 12:

[0135]

[0136] In the chemical formulas 4 to 12,

[0137] L, Ar, R1 to R9, R 11 To R 25 The definitions of n1 to n4 and their substituents are the same as those in the chemical formula A.

[0138] *c represents the bonding site on the phenotype, R 16 To R 25 One of them represents a single bond that bonds with *c.

[0139] According to one embodiment of the present invention, *c can be related to R. 18 Bonded single bonds.

[0140] According to one embodiment of the present invention, the organic compound represented by chemical formula A may be selected from the group consisting of the following organic compounds, but is not limited thereto.

[0141]

[0142] According to one embodiment of the present invention, the organic compound represented by chemical formula A may include an amino structure consisting of an umbrella-shaped tetraphenyl (5'-phenyl-1,1':3',1''-terphenyl) structure combined with a biphenyl-phenanthrene group structure, represented by the following chemical formula TP.

[0143] Chemical formula TP:

[0144]

[0145] In the chemical formula TP,

[0146] The definitions of R1 to R4, n1 to n4, and their substituents are the same as those given in chemical formula A.

[0147] * refers to the portion of the chemical formula TP bonded by single bonds.

[0148] Since the organic compound represented by chemical formula A of the present invention has the characteristic structural form described above, it has excellent hole injection characteristics compared with compounds that do not satisfy the structure of chemical formula A. Therefore, when used as a hole transport layer and / or hole transport auxiliary layer in an organic light-emitting diode, it can help ensure low drive voltage, high efficiency and long lifetime characteristics in device performance evaluation.

[0149] More specifically, the organic compound represented by Formula A of the present invention has an electron-rich phenanthrene group, thereby improving the efficiency and lifetime of organic light-emitting diodes when used as a hole transport layer or hole transport auxiliary layer, such as a hole transport auxiliary layer. In contrast, unlike the organic compound represented by Formula A of the present invention, where the phenanthrene group is directly bonded to an aromatic amino group or bonded through a biphenyl linker, existing in a fused planar form, this may result in excessively high deposition temperatures required for the deposition process to form the hole transport layer or hole transport auxiliary layer. Consequently, not only may the deposition process itself be inefficient, but the thermal stability of the molecule may also decrease at the high temperatures during the deposition process. Conversely, the organic compound represented by Formula A of the present invention introduces a biphenyl linker when linking the phenanthrene group to a nitrogen atom, thereby maintaining the advantages of a compound structure containing a phenanthrene group while ensuring efficiency in the deposition process and excellent thermal stability of the molecule.

[0150] That is, when the organic compound represented by chemical formula A of the present invention is used as the hole transport layer material, it exhibits excellent hole migration characteristics, thus increasing the efficiency and lifetime of the device. Furthermore, in one embodiment, when the organic compound represented by chemical formula A of the present invention is used as the hole transport auxiliary layer material, it possesses excellent hole migration characteristics and an appropriate energy level for a hole transport auxiliary layer, thus increasing the efficiency and lifetime of the device. The hole transport auxiliary layer functions to transport holes from the hole transport layer to the light-emitting layer and to block electrons from the light-emitting layer.

[0151] Furthermore, the organic compound represented by chemical formula A of the present invention has a triplet energy level (T1) within the appropriate range required for the hole transport layer and / or hole transport auxiliary layer. Therefore, it can effectively suppress the outward diffusion of triplet excitons generated in the emissive layer and improve luminous efficiency and device lifetime characteristics. In particular, when the triplet energy level of the compound used as the hole transport layer and / or hole transport auxiliary layer is too high, the HOMO level may become too deep, potentially leading to a decrease in hole transport characteristics and consequently, a reduction in device performance such as an increase in driving voltage. Conversely, when the triplet energy level is too low, the device efficiency may decrease because the diffusion of triplet excitons generated in the emissive layer cannot be prevented. Furthermore, when the LUMO energy level is too low, the device efficiency may decrease because the diffusion of leaked electrons generated in the emissive layer cannot be prevented.

[0152] An organic light-emitting diode according to an embodiment of the present invention includes: a first electrode (anode); a second electrode (cathode) disposed opposite to the first electrode; and one or more organic layers located inside the first electrode and the second electrode, wherein at least one of the more than one organic layers is a hole transport layer or a hole transport auxiliary layer containing the organic compound represented by the chemical formula A.

[0153] The organic layer may include one or more of the following: Hole Injection Layer (HIL), Hole Transport Layer (HTL), Hole Transport Auxiliary Layer, Emitting Layer (EML), Electron Transport Auxiliary Layer, Electron Transport Layer (ETL), and Electron Injection Layer (EIL).

[0154] For example, an organic light-emitting diode can have a structure in which a first electrode, a hole injection layer (HIL), a hole transport layer (HTL), a hole transport auxiliary layer, an emissive layer (EML), an electron transport layer (ETL), an electron injection layer (EIL), and a second electrode are stacked sequentially.

[0155] The organic layer containing the organic compound represented by chemical formula A in an embodiment of the present invention can be a hole transport layer (HTL) or a hole transport auxiliary layer.

[0156] The organic layer or more may further include one or more selected from the group consisting of a hole injection layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer.

[0157] The first electrode can be an anode, and the first electrode can contain transparent and highly conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), and zinc oxide (ZnO).

[0158] The second electrode can be a cathode, and it can contain materials such as lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). Furthermore, in the case of a top-emitting organic light-emitting diode, indium tin oxide (ITO) or indium zinc oxide (IZO) can be used to form a transparent second electrode that allows light to pass through.

[0159] The surface of the second electrode can be covered with a capping layer (CPL) by a composition for forming the capping layer.

[0160] Furthermore, a protective layer (encapsulation layer or protecting layer) can be provided on the cover layer to protect the organic light-emitting diode from the effects of moisture and oxygen. This protective layer can be made of a curable adhesive composition containing an inorganic hygroscopic agent.

[0161] An organic light-emitting diode according to an embodiment of the present invention includes a first electrode (anode); a second electrode (cathode) disposed opposite to the first electrode; and one or more organic layers located inside the first electrode and the second electrode, wherein at least one of the organic layers is a hole transport auxiliary layer containing the organic compound represented by the chemical formula A.

[0162] Wherein, when the organic layer containing the organic compound represented by chemical formula A in an embodiment of the present invention is a hole transport auxiliary layer, the hole injection layer, light emission layer, electron transport auxiliary layer, electron transport layer and electron injection layer constituting the organic layer or more can be defined as the following compounds, but are not limited thereto.

[0163] The hole injection layer or hole transport layer compound is not particularly limited, and any compound commonly used as a hole injection layer or hole transport layer compound can be used. Non-limiting examples of hole injection layer or hole transport layer compounds may include phthalocyanine derivatives, porphyrin derivatives, triarylamine derivatives, indole-carbazole derivatives, etc. For example, it may include 1,4,5,8,9,11-hexaazabenzophenanthrene-hexacarboxynitrile (HAT-CN), copper phthalocyanine (CuPc), 4,4',4”-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4',4”-tris(3-methylphenylamino)phenoxybenzene (m-MTDAPB), 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA), 4,4',4”-tris(N-(2-naphthyl)-N-phenylamino)triphenylamine (2-TNATA), N4,N4,N4',N4'-tetra([1,1' [1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine (N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine), bis(N-(1-naphthyl-n-phenyl))benzidine (α-NPD), N,N'-bis(naphthyl-1-yl)-N,N'-biphenyl-benzidine (NPB) or N,N'-biphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), etc.

[0164] The compounds contained in the luminescent layer are not particularly limited, and any compound commonly used as a luminescent layer compound can be used. A single luminescent compound or a host luminescent compound can be used.

[0165] According to one embodiment of the present invention, the light-emitting layer can be a blue or green light-emitting layer. When used as a blue light-emitting layer, excellent device performance can be achieved.

[0166] According to one embodiment of the present invention, when used as a blue emitting layer, the CIEx and CIEy color coordinate systems are not particularly limited, as long as they correspond to the blue emitting layer. For example, CIEx can be 0.10 to 0.15, and CIEy can be 0.03 to 0.10.

[0167] The luminescent compound serving as the luminescent layer may include, but is not limited to, compounds capable of emitting phosphorescence, fluorescence, thermal ignition delayed fluorescence (TADF, or also known as E-type delayed fluorescence), triplet-triplet annihilation, or a combination of these processes to achieve luminescence. Depending on the desired luminescence color, the luminescent compound can be selected from a variety of materials. Non-limiting examples of luminescent compounds include phenanthrene, anthracene, pyrene, tetraphenylene, pentaphenylene, perylene, naphthopyrene, dibenzopyrene, fluorene and β-cyclohexane derivatives, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bis(styrene) derivatives, bis(styrene)-arylene derivatives, diazaindenene derivatives, furan derivatives, benzofuran derivatives, isobenzofuran derivatives, dibenzofuran derivatives, coumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethylene derivatives, etc. Biological compounds, anthocyanin derivatives, oxabenzanthracene derivatives, xanthones derivatives, rhodamine derivatives, fluorescein derivatives, pyranonium derivatives, quinolone derivatives, acridine derivatives, oxazine derivatives, benzodioxin derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furanopyridine derivatives, 1,2,5-thiadiazolpyrene derivatives, promethazine derivatives, violacetone derivatives, pyrrolopyrrole derivatives, squaric acid cyanide derivatives, violacetone derivatives, phenazine derivatives, acridineone derivatives, desoxyflavin derivatives, fluorene derivatives, benzo[a]fluorene derivatives, aromatic boron derivatives, aromatic nitrogen-boron derivatives, and metal complexes (complexes formed by metals such as Ir, Pt, Au, Eu, Ru, Re, Ag, and Cu with heterocyclic ligands, etc.).For example, including N1,N1,N6,N6-tetrakis(4-(1-methylyl)phenyl)pyrene-1,6-diamine, 2,12-di-tert-butyl-5,9-bis(4-(tert-butyl)phenyl)-7-(3,5-di-tert-butylphenyl)-5,9-dihydro-5,9-diaza-13b-boronanaphene[3,2,1-de]anthracene (t-DABNA-dtB), platinum octaethylporphyrin (PtOEP), Ir(ppy)3, Ir(ppy)2(acac), Ir(mppy)3, Ir(PPy)2(m-bppy), BtpIr(acac), Ir(btp)2(acac), Ir(2-phq)3, Hex-Ir(phq)3, Ir(fbi)2(acac), fac- Tris(2-(3-p-xylyl)phenyl)pyridineiridium(III), Eu(dbm)3(Phen), Ir(piq)3, Ir(piq)2(acac), Ir(Fliq)2(acac), Ir(Flq)2(acac), Ru(dtb-bpy)3·2(PF6), Ir(BT)2(aca c), Ir(DMP)3, Ir(Mphq)3IR(phq)2tpy, fac-Ir(ppy)2Pc, Ir(dp)PQ2, Ir(Dpm)(Piq)2, H ex-Ir(piq)2(acac), Hex-Ir(piq)3, Ir(dmpq)3, Ir(dmpq)2(acac), FPQIrpic, FIrpic, etc.

[0168] The host compound for the luminescent layer can be a luminescent host, a hole-transporting host, an electron-transporting host, or a combination thereof. Non-limiting examples of luminescent host compounds include fused-ring derivatives such as anthracene or pyrene, bis(5-phenylene)-anthracene derivatives or stilbene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzo[a]fluorene derivatives, n-phenylcarbazole (9-phenylcarbazole) derivatives, carbazole nitrile derivatives, etc. Non-limiting examples of hole-transporting host substances include carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, triarylamine derivatives, indole-carbazole derivatives, and benzo[a]oxazine-phenoxazine derivatives, etc. Non-limiting examples of electron-transporting host substances include pyridine derivatives, triazine derivatives, phosphine oxide derivatives, benzo[a]furan-pyridine derivatives, and dibenzo[a]oxasiloline derivatives, etc. Examples include 9,10-bis(2-naphthyl)anthracene (ADN), tris(8-hydroxyquinoline)aluminum (Alq3), BAlq (8-hydroxyquinoline beryllium salt), DPVBi (4,4'-bis(2,2-bistyryl)-1,1'-biphenyl) series, spiro-DPVBi (spiro-4,4'-bis(2,2-bistyryl)-1,1'-biphenyl), LiPBO (2-(2-benzoxazolyl)phenol lithium salt), bis(bistyryl)benzene, aluminum-quinoline metal complexes, imidazole, thiazole and oxazole metal complexes, etc.

[0169] The electron injection layer or electron transport layer compound is not particularly limited, and any compound commonly used as an electron injection layer or electron transport layer compound may be used. Non-limiting examples of electron injection layer or electron transport layer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, violet ketone derivatives, coumarin derivatives, naphthylimide derivatives, anthraquinone derivatives, dibenzoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives, thiophene derivatives, triazole derivatives, thiadiazole derivatives, metal complexes of oxime derivatives, quinoline metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzo[a]azole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, and triazine derivatives. Pyrazine derivatives, benzoquinoline derivatives, imidazopyridine derivatives, borane derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives, naphthidine derivatives, aldehyde azide derivatives, carbazole derivatives, indole derivatives, phosphine oxide derivatives, bis(5-phenylene oxide) metal complexes, quinoline alcohol metal complexes, hydroxyazole metal complexes, azomethyl alkaloid metal complexes, tyrosine metal complexes, flavonol metal complexes, benzoquinoline metal complexes, metal salts, etc. These materials can be used alone or in combination with other materials. For example, they may include 2-(4-(9,10-bis(naphthyl-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, tris(8-hydroxyquinoline)aluminum (Alq3), LiF, Liq, Li2O, BaO, NaCl, CsF, etc.

[0170] The electron transport auxiliary layer compound located between the electron transport layer and the luminescent layer is not particularly limited, and any compound commonly used as an electron transport auxiliary layer compound can be used. For example, the electron transport auxiliary layer can contain pyrimidine derivatives, etc.

[0171] The organic light-emitting diode of one embodiment of the present invention can be either top-emitting or bottom-emitting.

[0172] An organic light-emitting diode according to an embodiment of the present invention can be used in a display device.

[0173] The organic light-emitting diode of one embodiment of the present invention can be applied to transparent display devices, mobile display devices, flexible display devices, etc., but is not limited thereto.

[0174] An organic light-emitting diode according to an embodiment of the present invention may include a series structure, which includes multiple light-emitting stacks between the anode and the cathode.

[0175] The following examples illustrate the method for synthesizing the compounds. However, the method for synthesizing the compounds of the present invention is not limited to the methods described in the examples below.

[0176] Synthesis example

[0177] Representatively, a synthesis example of compound 1 is described, and the compound of chemical formula A of the present invention can be synthesized in a similar manner to the reaction of compound 1.

[0178] The solvents, catalysts, protecting groups, leaving groups, reaction temperatures, and reaction times in the following reaction formulas are representative examples, and equivalent solvents, catalysts, protecting groups, leaving groups, reaction temperatures, reaction times, and reactant stoichiometry can also be used.

[0179] 1. Synthesize compound 1

[0180] Compound 1 can be synthesized as follows, but is not limited to these methods.

[0181] Reaction 1:

[0182]

[0183] Under a nitrogen atmosphere, reactant 1 (22 mmol), reactant 2 (20 mmol), Pd2(dba)3 (0.8 mmol), Sphos (1.6 mmol), t-BuONa (50 mmol), and toluene were added to a reaction flask, and the mixture was stirred and refluxed at approximately 90 °C for 3 hours. The organic layer was then extracted with toluene and water. The extract was treated with MgSO4 to remove residual water and reduce concentration, and then purified by column chromatography followed by recrystallization to obtain the product.

[0184] Representative synthesized compounds are shown in Table 1 below. Specific compounds of the present invention and similar compounds can be synthesized using the synthetic examples described.

[0185] Table 1

[0186]

[0187]

[0188] The effects of the compound of the present invention were confirmed by the following experiments. This is only a typical example, and the experimental examples are not limited thereto.

[0189] Experiment Example 1: Simulation Results of Hole Transport Auxiliary Layer

[0190] The hole transport auxiliary layer serves to reduce hole accumulation at the emissive layer interface due to the HOMO energy level difference between the hole transport layer and the emissive layer. Therefore, it is preferable that the HOMO energy level difference with the emissive layer is smaller than the HOMO energy level difference with the hole transport layer. Furthermore, it should have an energy level higher than the LUMO energy level of the emissive layer to minimize electron leakage from the emissive layer to the hole transport layer.

[0191] To confirm whether the organic compound represented by chemical formula A of the present invention is suitable as a hole transport auxiliary layer material, the HOMO level (eV) and LUMO level (eV) were calculated using Spartan software (B3LYP DFT 6-31G* by Spartan 16) and are shown in Table 2 below.

[0192] Table 2

[0193]

[0194]

[0195] Example 1: Fabrication of an organic light-emitting diode (blue light-emitting layer)

[0196] The substrate with ITO (100nm) layered on top of the first electrode (anode) of the organic light-emitting diode is divided into a second electrode (cathode) region, a first electrode (anode) region and an insulating layer by photolithography and patterned. Then, in order to improve the work function of the first electrode (ITO) and to clean it, the surface is treated by ultraviolet (UV)-ozone treatment and O2:N2 plasma.

[0197] Then, a 10 nm thick hole injection layer (HIL) was formed by depositing a mixture of NDP-9 (2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyrene-2-ylidene)-malononitrile and N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine) in a 3:97 ratio on the anode. Next, a hole transport layer with a thickness of 100 nm is formed by vacuum deposition of N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine (N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine) on the hole injection layer. Compound 1 with a thickness of 15 nm is formed on the hole transport layer (HTL) as a hole transport auxiliary layer.

[0198] 9,10-bis(2-naphthyl)anthracene (ADN) was used as the host and 2,12-di-tert-butyl-5,9-bis(4-(tert-butyl)phenyl)-7-(3,5-di-tert-butylphenyl)-5,9-dihydro-5,9-diaza-13b-borona[3,2,1-de]anthracene (2,12-Di-tert-butyl-5,9-bis(4-(tert-buty))anthracene was used. A 25 nm thick blue emitting layer is deposited on top of the hole transport auxiliary layer using 1-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (2-(4-(9,10-Di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole and Liq in a 1:1 weight ratio as an electron transport layer (ETL). A 1 nm thick electron injection layer (Liq) is deposited on top of the electron transport layer (ETL), and a 16 nm thick mixture of magnesium and silver in a 1:4 weight ratio is deposited as the cathode. A 60 nm thick layer of N4,N4'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD) is deposited on the cathode as a capping layer. A seal cap containing a hygroscopic agent is bonded to the capping layer using a UV-curable adhesive to form a protective film, thereby protecting the organic light-emitting diode from atmospheric oxygen or moisture, thus fabricating the organic light-emitting diode.

[0199] Examples 2 to 16

[0200] Except for replacing compound 1, which was used as the hole transport auxiliary layer material in Example 1, with the compounds shown in Table 3 below, organic light-emitting diodes of Examples 2 to 16 were prepared using the same method as in Example 1.

[0201] Comparative Examples 1 to 3

[0202] Organic light-emitting diodes of Comparative Examples 1 to 3 were prepared using the same method as in Example 1, except that Compound 1 used as the hole transport auxiliary layer material in Example 1 was replaced with the following Comparative Compound 1, Comparative Compound 2 and Comparative Compound 3.

[0203] Experiment Example 2: Performance Evaluation of Organic Light Emitting Diodes (Blue Device)

[0204] Compare compound 1:

[0205] Compare compound 2:

[0206] Compare compound 3:

[0207] For each organic light-emitting diode prepared in Examples 1 to 16 and Comparative Examples 1 to 3, a CS-2000 from Konica Minolta was used to apply 10 mA / cm². 2 The driving voltage (V) and external quantum efficiency (EQE) (%) were measured using the current. Furthermore, the driving voltage was determined using McScience's M6000 at 10 mA / cm². 2 The method of determining lifetime (LT95) (hrs) was validated by constant current drive to confirm the reduction time of brightness from initial brightness to 95% level. The measurement results are shown in Table 3 below.

[0208] Table 3

[0209]

[0210]

[0211] The organic compound represented by chemical formula A of the present invention comprises an amino structure combining an umbrella-shaped tetraphenyl (5'-phenyl-1,1':3',1''-terphenyl) structure represented by the following chemical formula TP with a biphenyl-phenanthrene group. The embodiments described confirm that the organic compound represented by chemical formula A of the present invention possesses an electron-rich phenanthrene group, thereby improving the efficiency and lifetime of organic light-emitting diodes.

[0212] Chemical formula TP:

[0213]

[0214] Conversely, Comparative Compound 1 of Comparative Example 1 has a structure lacking two phenanthrene groups, Comparative Compound 2 of Comparative Example 2 has a structure in which phenanthrene groups are bonded to an amino group without a biphenyl linker, and Comparative Compound 3 of Comparative Example 3 has a structure in which phenanthrene groups are bonded to an amino group via a phenyl linker. Device evaluation results confirm that the device performance is worse than when using the organic compound represented by Chemical Formula A of this invention.

[0215] Experiment Example 3: Determination of the lowest triplet energy

[0216] For the organic compound represented by chemical formula A of the present invention and comparative compounds 1, 2 and 3, the triplet energy (triplet 1, referred to as "T1") (unit: eV, absolute value) was calculated by quantum computing experiments using Gaussian software (B3LYP DFT 6-31G* by Gaussian 16) and is shown in Table 5 below.

[0217] Table 5

[0218]

[0219] The organic compound represented by chemical formula A of the present invention, as a hole transport layer or hole transport auxiliary layer, has a suitable range of triplet energy levels (T1), thereby effectively suppressing the outward diffusion of triplet excitons generated in the light-emitting layer and improving luminous efficiency and device lifetime characteristics.

[0220] When the triplet energy level is too high, it may deepen the HOMO level, which could lead to a decrease in hole transport characteristics or an increase in the device's drive voltage. Conversely, when the triplet energy level is too low, it may be unable to prevent the diffusion of triplet excitons generated from the light-emitting layer, resulting in a decrease in device efficiency.

[0221] The organic compound represented by chemical formula A of the present invention can have triplet energy levels within a range that ensures a balance between the binding effect of triplet excitons and charge transport properties.

Claims

1. An organic compound represented by the following chemical formula A, characterized in that, Chemical formula A: ， In the chemical formula A, L is selected from the group consisting of arylene groups with 6 to 30 carbon atoms (either single-bonded, substituted or unsubstituted) and heteroarylene groups with 3 to 60 carbon atoms (either substituted or unsubstituted). Ar is an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heteroaryl group with 3 to 60 substituted or unsubstituted carbon atoms. R1 to R 25 They may be the same as or different from each other, and each independently consists of one selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl groups of 1 to 30, substituted or unsubstituted aryl groups of 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups of 3 to 60 carbon atoms. n1 and n2 may be the same or different from each other, and each is an independent integer from 0 to 5. n3 is an integer from 0 to 3. n4 is an integer from 0 to 4. In L, Ar and R1 to R 25 When substituted, the substituents may be the same as or different from each other, and may be selected from deuterium, cyano, trifluoromethyl, nitro, halogen group, hydroxyl, trimethylsilyl, alkyl with 1 to 30 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, alkenyl with 2 to 30 carbon atoms, cycloalkenyl with 3 to 20 carbon atoms, alkynyl with 2 to 30 carbon atoms, cycloalkynyl with 3 to 20 carbon atoms, aryl with 6 to 30 carbon atoms, aralkyl with 7 to 30 carbon atoms, heteroaryl with 3 to 60 carbon atoms, heteroaryl with 4 to 60 carbon atoms, amino, etc. The substituents are one or more from the group consisting of alkylamino groups having 1 to 30 carbon atoms, arylalkylamino groups having 7 to 30 carbon atoms, aromaticamino groups having 6 to 30 carbon atoms, heteroaromaticamino groups having 3 to 60 carbon atoms, silylamino groups, alkylsilylamino groups having 1 to 30 carbon atoms, arylsilylamino groups having 6 to 30 carbon atoms, alkoxy groups having 1 to 30 carbon atoms, aryloxy groups having 6 to 30 carbon atoms, alkylthio groups having 1 to 30 carbon atoms, and arylthio groups having 6 to 30 carbon atoms. When there are multiple substituents, the substituents may be the same or different from each other. *a, *b1, and *b2 are different from each other and represent the bonding sites on the phenylene group, while *c represents the bonding site on the phenanthrene group. One of R5 to R9 represents a single bond that bonds with *a. R 10 To R 15 One of them represents a single bond that bonds with *b1. R 10 To R 15 Another representation in the text is a single bond bonded to *b2. R 16 To R 25 One of them represents a single bond that bonds with *c.

2. The organic compound according to claim 1, characterized in that, The L is a single bond or a substituted or unsubstituted phenylene.

3. The organic compound according to claim 1, characterized in that, The Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted phenylcarbazoyl, and substituted or unsubstituted 9-phenylcarbazoyl.

4. The organic compound according to claim 1, characterized in that, The R1 to R 25 They may be the same or different from each other, and each can be hydrogen or deuterium independently.

5. An organic light-emitting diode, characterized in that, First electrode: Second electrode; The first electrode is an electrode disposed opposite to the second electrode; and A layer of one or more organic materials is located between the first electrode and the second electrode. At least one of the organic layers comprises an organic compound represented by chemical formula A according to claim 1.

6. The organic light-emitting diode according to claim 5, characterized in that, The organic layer containing the organic compound represented by the chemical formula A is a hole transport layer or a hole transport auxiliary layer.

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