Organic compound and organic light emitting diode including same

Abstract

The organic compound represented by Chemical Formula 1 of the present invention can achieve excellent hole injection characteristics and hole transport characteristics. Moreover, the hole transport auxiliary layer of the organic light emitting diode according to the present invention comprises the organic compound represented by Chemical Formula 1 according to the present invention, thereby improving the driving voltage, efficiency, and lifespan characteristics of the organic light emitting diode.

Description

Technical Field

[0001] The invention relates to an organic compound and an organic light emitting diode comprising the organic compound. Background Art

[0002] Compared with other flat panel display devices such as existing liquid crystal displays (LCDs), plasma flat panel displays (PDPs) and field emission displays (FEDs), organic light emitting diodes have a simpler structure and have many advantages in the preparation process. They have excellent high brightness and viewing angle characteristics, fast response speed and low driving voltage. Therefore, they are being actively developed for use as light sources for flat panel displays such as wall-mounted TVs or back lights of displays, lighting and billboards.

[0003] Organic light-emitting diodes are composed of an organic layer between two electrodes. They use the following principle: electrons and holes are injected into the light-emitting layer from the two electrodes, and the electrons and holes combine to generate excitons. When the generated excitons fall from the excited state to the ground state, light is generated.

[0004] The organic light emitting diode may include at least one light emitting layer. Generally, an organic light emitting diode having a plurality of light emitting layers includes a plurality of light emitting layers emitting light having different peak wavelengths, so that a specific color may be realized by a combination of light having different peak wavelengths.

[0005] This organic light emitting diode can be divided into a front light emitting diode and a back light emitting device structure. The front light emitting diode uses a reflective cathode (Cathode) to emit light generated from the light emitting layer to the semi-transparent anode (Anode) side. On the contrary, the back light emitting diode uses a reflective anode (Anode) to emit light generated from the light emitting layer and reflected to the anode to the transparent cathode (Cathode) side as the driving direction of the thin film transistor.

[0006] Existing patent literature

[0007] Existing patent document 1: KR 2019-0020514 A

[0008] Existing Patent Document 2: KR 2083707 B1 Summary of the invention

[0009] Technical issues

[0010] The object of the present invention is to provide a novel organic compound and an organic light emitting diode comprising the same.

[0011] In addition to the above-mentioned problems, embodiments of the present invention may also be used to solve other problems not specifically mentioned.

[0012] The purpose of the present invention is not limited to the purpose described above, and other purposes and advantages of the present invention not mentioned can be understood by the following description, and will be more clearly understood by the embodiments of the present invention. And, it is obvious that the purposes and advantages of the present invention can be achieved by the means shown in the scope of the invention and their combination.

[0013] Technical Solution

[0014] According to an aspect of the present invention, an organic compound represented by the following Chemical Formula 1 may be provided.

[0015] Chemical formula 1:

[0016]

[0017] According to another aspect of the present invention, an organic light emitting diode can be provided, comprising: an anode; a cathode arranged opposite to the anode; and one or more organic layers arranged between the anode and the cathode, at least one of the organic layers comprising the organic compound represented by the above Chemical Formula 1.

[0018] Effects of the Invention

[0019] The organic compound represented by Chemical Formula 1 of the present invention may achieve excellent hole injection characteristics and hole transport characteristics.

[0020] Furthermore, the hole transport auxiliary layer of the organic light emitting diode of the present invention includes the organic compound represented by Chemical Formula 1 of the present invention, thereby improving the driving voltage, efficiency and lifespan characteristics of the organic light emitting diode.

[0021] Also, when the organic compound represented by Chemical Formula 1 of the present invention is used as a hole transport auxiliary layer material, it can have an appropriate energy level as a hole transport auxiliary layer, which plays a role of transporting holes from the hole transport layer to the light emitting layer and blocking electrons from the light emitting layer.

[0022] Furthermore, the organic light emitting diode of the present invention, as a hole transport auxiliary layer including the organic compound represented by Chemical Formula 1 of the present invention, can achieve excellent color coordinates targeted by the light emitting layer even when combined with a light emitting layer of any color.

[0023] The effects of the present invention are not limited to the above-mentioned effects, and a person skilled in the art can clearly understand other effects not mentioned through the entire description of this specification. DETAILED DESCRIPTION

[0024] The aforementioned objects, features and advantages are described in detail below with reference to the following embodiments so that those skilled in the art can easily implement the technical ideas of the present invention.

[0025] In describing the present invention, if it is judged that a detailed description of known techniques related to the present invention may unnecessarily obscure the gist of the present invention, the detailed description will be omitted.

[0026] In this specification, when referring to structural elements such as "including", "containing", "having", "forming", "configured", or "having", other parts may be added unless "only to" is used. When a structural element is expressed in the singular, the plural is included unless otherwise specifically stated.

[0027] In interpreting the structural elements in the present specification, they are interpreted as including the error range even if there is no individual explicit description.

[0028] In this specification, the arrangement of an arbitrary structure "on the top (or bottom)" of a structural element or "above (or below)" a structural element means that the arbitrary structure is not only arranged in contact with the top (or bottom) of the above-mentioned structural element, but also other structures may exist between the above-mentioned structural element and the arbitrary structure arranged on (or below) the above-mentioned structural element.

[0029] The term "halogen group" used in the present specification includes fluorine, chlorine, bromine and iodine.

[0030] The term "alkyl" used in this specification refers to both straight-chain alkyl and branched-chain alkyl. Unless otherwise specified, the alkyl 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. Further, the alkyl may be optionally substituted.

[0031] The term "cycloalkyl" used in this specification refers to a cyclic alkyl group. Unless otherwise specified, the cycloalkyl group contains 3 to 20 carbon atoms and may include, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, etc. Further, the cycloalkyl group may be optionally substituted.

[0032] The term "alkenyl" used in this specification refers to both straight-chain alkenyl and branched alkenyl groups having one or more carbon-carbon double bonds. Unless otherwise specified, alkenyl contains 2 to 30 carbon atoms and may include, but is not limited to, vinyl, allyl, isopropenyl, 2-butenyl, etc. Further, alkenyl may be optionally substituted.

[0033] The term "cycloalkenyl" used in the present specification refers to a cyclic alkenyl group. Unless otherwise specified, the cycloalkenyl group contains 3 to 20 carbon atoms, and further, the cycloalkenyl group may be optionally substituted.

[0034] The term "alkynyl" used in this specification refers to both straight-chain alkynyl and branched alkynyl having more than one carbon-carbon triple bond. Unless otherwise specified, the alkynyl contains 2 to 30 carbon atoms, which may include but are not limited to ethynyl, 2-propynyl (2-propynyl) and the like. Further, the alkynyl may be optionally substituted.

[0035] The term "cycloalkynyl" used in the present specification refers to a cyclic alkynyl group. Unless otherwise specified, the cycloalkynyl group contains 3 to 20 carbon atoms, and further, the cycloalkynyl group may be optionally substituted.

[0036] The term "aralkyl" or "arylalkyl" used in the present specification is used interchangeably, and refers to an alkyl group having an aromatic group as a substituent. Further, the aralkyl group (arylalkyl group) may be optionally substituted.

[0037] The terms "aryl" or "aromatic group" used in this specification have the same meaning, and aryl includes monocyclic groups and polycyclic groups. Polycyclic rings may include "condensed rings", which are two or more rings, wherein two adjacent rings have two carbon or heteroatoms in common. In addition, it may also include a form in which two or more rings are simply attached or fused to each other. Unless otherwise specified, aryl contains 6 to 30 carbon atoms and may include, but is not limited to, phenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, etc. Further, aryl may be optionally substituted.

[0038] The terms "heteroaryl" or "heteroaromatic group" used in this specification have the same meaning, and heteroaryl includes both monocyclic groups and polycyclic groups. Polycyclic rings may contain "fused rings", which are two or more rings in which two adjacent rings have two carbon or heteroatoms in common. In addition, it may also include a form in which two or more rings are simply attached or fused to each other. Unless otherwise specified, the heteroaryl group contains 1 to 60 carbon atoms, and when there are 1 or 2 carbon atoms, additional hetero elements are included to form a ring, and the heteroaryl group may contain 1 to 30 carbon atoms, in which case one or more carbons in the ring are replaced by heteroatoms such as oxygen (O), nitrogen (N), sulfur (S) or selenium (Se), and may include but is not limited to 6-membered monocyclic rings, such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl ; polycyclic, for example, phenoxathiophenyl, indolizinyl, indolyl, purinyl, quinolyl, isoquinolyl, benzooxy oxazolyl, benzothiazolyl, dibenzooxy oxazolyl, dibenzothiazolyl, benzimidazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, phenylcarbazolyl, 9-phenylcarbazolyl, carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridyl, 2-pyrimidinyl, etc. Further, heteroaryl can be optionally substituted.

[0039] The term "heterocyclic group" used in this specification means that one or more of the carbon atoms constituting an aryl group, a cycloalkyl group, a cycloalkenyl group, a cycloalkynyl group, an aralkyl group, an arylamino group, etc. are substituted by a heteroatom (hetero-atom) such as oxygen (O), nitrogen (N), sulfur (S), etc., and with reference to the above definition, includes a heteroaryl group, a heterocycloalkyl group, a heterocycloalkenyl group, a heterocycloalkynyl group, a heteroarylalkyl group, a heteroarylamino group, etc., and further, the heterocycle may be optionally substituted.

[0040] Unless otherwise specified, the term "carbon ring" used in the present specification may include "cycloalkyl", "cycloalkenyl", "cycloalkynyl" as alicyclic ring groups, and "aryl (aromatic group)" as aromatic ring groups.

[0041] The terms "heteroalkyl", "heteroalkenyl", "heteroalkynyl" and "heteroarylalkyl" as used in the present specification mean that one or more of the carbon atoms constituting the group are substituted by heteroatoms such as oxygen (O), nitrogen (N) and sulfur (S), and further, the heteroalkyl, heteroalkenyl, heteroalkynyl and heteroarylalkyl may be optionally substituted.

[0042] The terms "alkylamino", "arylalkylamino", "arylamino" and "heteroarylamino" used in this specification refer to amino groups (or amine groups) substituted by the above-mentioned alkyl groups, arylalkyl groups, aryl groups and heteroaryl groups, and include primary amino groups, secondary amino groups and tertiary amino groups (or amine groups). Furthermore, alkylamino groups, arylalkylamino groups, arylamino groups and heteroarylamino groups may be optionally substituted.

[0043] The terms "alkylsilyl", "arylsilyl", "alkoxy", "aryloxy", "alkylthio" and "arylthio" used in the present specification mean that the silyl, oxy and thio groups are substituted by the above-mentioned alkyl and aryl groups, respectively. Furthermore, the alkylsilyl, arylsilyl, alkoxy, aryloxy, alkylthio and arylthio groups may be optionally substituted.

[0044] The terms "arylene", "arylalkylene", "heteroarylene", and "heteroarylalkylene" used in this specification mean that the above-mentioned aryl, arylalkyl, heteroaryl, and heteroarylalkyl are each a divalent substituent further containing one substituent. Furthermore, the arylene, arylalkylene, heteroarylene, and heteroarylalkylene may be optionally substituted.

[0045] The term "substituted" used in this specification means that a hydrogen (H) atom bonded to a carbon atom of the compound of the present invention is replaced by a substituent other than hydrogen, and when there are multiple substituents, each substituent may be the same or different from each other.

[0046] The substituents may be independently selected from deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxyl, trimethylsilyl, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, alkenyl having 2 to 30 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, alkynyl having 2 to 30 carbon atoms, cycloalkynyl having 3 to 20 carbon atoms, aryl having 6 to 30 carbon atoms, aralkyl having 7 to 30 carbon atoms, heteroaryl having 5 to 60 carbon atoms, heteroaryl having 6 to 60 carbon atoms, atom, an alkylamino group having 1 to 30 carbon atoms, an arylalkylamino group having 7 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, a heteroarylamino group having 5 to 60 carbon atoms, a silyl group, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, and an arylthio group having 6 to 30 carbon atoms

[0047] In the present specification, unless otherwise specified, the position of substitution is not particularly limited as long as the hydrogen atom is substituted, that is, the position of the substituent is substitutable. When there are two or more substituents, the substituents may be the same or different from each other.

[0048] Unless otherwise stated, each object and substituent defined in this specification may be the same or different.

[0049] In this specification, unless otherwise specified, all unit standards are based on weight (wt). For example, when "%" is recorded, it is interpreted as weight percentage (wt%).

[0050] Hereinafter, the organic compound of the present invention and the organic light emitting diode including the same will be described in detail.

[0051] The organic compound of the present invention can be represented by Chemical Formula 1 below.

[0052] Chemical formula 1:

[0053]

[0054] In the above chemical formula 1,

[0055] L1 to L3 may each independently be one selected from the group consisting of a single bond, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, and a substituted or unsubstituted heteroarylalkyl group having 6 to 60 carbon atoms,

[0056] R1 to R 16and Ar1 are the same as or different from each other and can be each independently selected from hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxyl, trimethylsilylethynyl (TMS), substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl having 3 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 30 carbon atoms, substituted or unsubstituted cycloalkynyl having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 5 to 60 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 60 carbon atoms one of the group consisting of a substituted or unsubstituted amine group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 7 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 5 to 60 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms and a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms,

[0057] Ar2 is a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms,

[0058] Optionally, when the above L1 to L3, R1 to R 16When Ar1 and Ar2 are substituted, they may be selected from deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxyl, trimethylsilylethynyl (TMS), alkyl groups having 1 to 30 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, alkenyl groups having 2 to 30 carbon atoms, cycloalkenyl groups having 3 to 20 carbon atoms, alkynyl groups having 2 to 30 carbon atoms, cycloalkynyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 30 carbon atoms, aralkyl groups having 7 to 30 carbon atoms, heteroaryl groups having 5 to 60 carbon atoms, heteroaralkyl groups having 6 to 60 carbon atoms, amino groups, The present invention is substituted with one or more substituents selected from the group consisting of alkylamino groups having 1 to 30 carbon atoms, aralkylamino groups having 7 to 30 carbon atoms, arylamino groups having 6 to 30 carbon atoms, heteroarylamino groups having 5 to 60 carbon atoms, silyl groups, alkylsilyl groups having 1 to 30 carbon atoms, arylsilyl 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 a plurality of the above substituents are present, the above substituents may be the same as or different from each other.

[0059] The compound represented by the above chemical formula 1 is an amine structure NRR'R", in which the 1st position of R as a dibenzofuran group is connected to N (nitrogen) through a connecting group L2, R' is a terphenyl group connected through a connecting group L1, and R" is Ar1 connected through N (nitrogen) and a connecting group L3, and the above Ar1 can be selected in a variety of ways. Furthermore, Ar2 as a substituent is bonded to the 4th position of the above dibenzofuran group, so that the hole injection characteristics and hole transport characteristics can be increased by increasing conjugation and expanding the electron cloud of the highest occupied molecular orbital (HOMO). In addition, it can have a suitable energy level as a hole transport auxiliary layer, which plays a role in transferring holes from the hole transport layer to the light-emitting layer and blocking electrons from the light-emitting layer, so it can show characteristics suitable for being a hole transport auxiliary layer material.

[0060] According to an example of the present invention, the R7 may be a substituent represented by the following Chemical Formula 2.

[0061] Chemical formula 2:

[0062]

[0063] In the above chemical formula, * represents a binding site, n is an integer from 0 to 5, and R 17Each may be independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms.

[0064] According to one example of the present invention, the above-mentioned Ar1 can be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. Compared with when the above-mentioned Ar1 is a heteroaryl group, the hole mobility when the above-mentioned Ar1 is an aryl group can be improved. For example, Ar1 can be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms or a substituted or unsubstituted aryl group having 6 to 15 carbon atoms. When it has more than 18 carbon atoms, the characteristics as a hole transport auxiliary layer material may be reduced. For example, the above-mentioned Ar1 can be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted dimethyl fluorene group, a substituted or unsubstituted triphenylene group.

[0065] According to an example of the present invention, the Ar2 may be one of the substituents represented by the following Chemical Formulae 3 to 5.

[0066] Chemical formula 3:

[0067]

[0068] Chemical formula 4:

[0069]

[0070] Chemical formula 5:

[0071]

[0072] In the above chemical formula, * represents a binding site, o is an integer from 0 to 5, p is an integer from 0 to 7, q is an integer from 0 to 9,

[0073] R 18 To R 20 Each may be independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms.

[0074] According to an embodiment of the present invention, the L1 mentioned above may be a single bond.

[0075] According to an example of the present invention, the above Chemical Formula 1 may be selected from the group consisting of the following Chemical Formulas 6 to 13 according to the bonding position relationship of three phenyl groups of a terphenyl group bonded to nitrogen (N) of an arylamine group.

[0076] Chemical formula 6:

[0077]

[0078] Chemical formula 7:

[0079]

[0080] Chemical formula 8:

[0081]

[0082] Chemical formula 9:

[0083]

[0084] Chemical formula 10:

[0085] Chemical formula 11:

[0086] Chemical formula 12:

[0087] Chemical formula 13:

[0088]

[0089] In the above Chemical Formulas 6 to 13,

[0090] L2, L3, R 11 To R 16 , Ar1 and Ar2 are as defined in the chemical formula 1,

[0091] R 21 To R 33The same as or different from each other, and may each independently be selected from hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxyl, trimethylsilylethynyl (TMS), substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl having 3 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 30 carbon atoms, substituted or unsubstituted cycloalkynyl having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 5 to 60 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 60 carbon atoms The present invention is one of the group consisting of a substituted or unsubstituted amine, a substituted or unsubstituted alkylamino having 1 to 30 carbon atoms, a substituted or unsubstituted aralkylamino having 7 to 30 carbon atoms, a substituted or unsubstituted arylamino having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino having 5 to 60 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms and a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms.

[0092] According to an embodiment of the present invention, the L2 may be a single bond.

[0093] According to one embodiment of the present invention, the above Chemical Formula 1 can be selected from the group consisting of the following Chemical Formulas 14 to 45, which is selected in the structures of Chemical Formulas 6 to 13 as a single bond, and is represented according to the type of structure bonded to the Ar2 position of the dibenzofuran group.

[0094] Chemical formula 14:

[0095] Chemical formula 15:

[0096] Chemical formula 16:

[0097] Chemical formula 17:

[0098] Chemical formula 18:

[0099] Chemical formula 19:

[0100] Chemical formula 20:

[0101] Chemical formula 21:

[0102] Chemical formula 22:

[0103] Chemical formula 23:

[0104] Chemical formula 24:

[0105] Chemical formula 25:

[0106] Chemical formula 26:

[0107] Chemical formula 27:

[0108] Chemical formula 28:

[0109] Chemical formula 29:

[0110] Chemical formula 30:

[0111] Chemical formula 31:

[0112] Chemical formula 32:

[0113] Chemical formula 33:

[0114] Chemical formula 34:

[0115] Chemical formula 35:

[0116] Chemical formula 36:

[0117] Chemical formula 37:

[0118] Chemical formula 38:

[0119] Chemical formula 39:

[0120] Chemical formula 40:

[0121] Chemical formula 41:

[0122] Chemical formula 42:

[0123] Chemical formula 43:

[0124]

[0125] Chemical formula 44:

[0126]

[0127] Chemical formula 45:

[0128]

[0129] In the above Chemical Formulas 14 to 45,

[0130] L3, R 11 To R 16 and Ar1 is as defined in the chemical formula 1,

[0131] R 21 To R 42 The same as or different from each other, and may each independently be selected from hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxyl, trimethylsilylethynyl (TMS), substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl having 3 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 30 carbon atoms, substituted or unsubstituted cycloalkynyl having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 5 to 60 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 60 carbon atoms The present invention is one of the group consisting of a substituted or unsubstituted amine, a substituted or unsubstituted alkylamino having 1 to 30 carbon atoms, a substituted or unsubstituted aralkylamino having 7 to 30 carbon atoms, a substituted or unsubstituted arylamino having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino having 5 to 60 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms and a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms.

[0132] According to an example of the present invention, the compound represented by the above Chemical Formula 1 may be any one selected from the following compounds, and the following compounds may be further substituted.

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167] An organic light emitting diode according to one aspect of the present invention includes an anode and a cathode disposed opposite to the anode, and may include an organic layer between the anode and the cathode.

[0168] According to an example of the present invention, the organic layer may include a hole transport auxiliary layer, and the hole transport auxiliary layer may include the compound represented by Chemical Formula 1 of the present invention.

[0169] In addition to the hole transport auxiliary layer, the above-mentioned organic layer may also include one or more selected from the group consisting of a hole injection layer (HIL), a hole transport layer (HTL), an emitting layer (EML), an electron transport layer (ETL) and an electron injection layer (EIL).

[0170] For example, an organic light emitting diode may have a structure in which an anode, a hole injection layer (HIL), a hole transport layer (HTL), a hole transport auxiliary layer (Hole transport auxiliary layer), a light emitting layer (EML), an electron transport layer (ETL), an electron injection layer (EIL) and a cathode are sequentially stacked.

[0171] The organic layer may further include an electron transport auxiliary layer and the like.

[0172] The anode may include transparent and highly conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), and zinc oxide (ZnO).

[0173] The cathode may include materials such as lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). In addition, in the case of a front-emitting organic light-emitting diode, indium tin oxide (ITO) or indium zinc oxide (IZO) may be used to form a transparent cathode that is light-transmitting.

[0174] A covering layer (CPL) may be formed on the surface of the cathode using a composition for forming a covering layer.

[0175] The hole injection layer or hole transport layer compound is not particularly limited, and any compound can be used as long as it is generally used as a hole injection layer or hole transport layer compound. Non-limiting examples of hole injection layer or hole transport layer compounds may include phthalocyanine derivatives, porphyrin derivatives, triarylamine derivatives; indole and carbazole derivatives. For example, they include 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (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'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine (N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamin e), bis(N-(1-naphthyl-n-phenyl))benzidine (α-NPD), N,N'-di(naphth-1-yl)-N,N'-biphenyl-benzidine (NPB) or N,N'-biphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), etc.

[0176] The compound contained in the above-mentioned light-emitting layer is not particularly limited, and a light-emitting compound alone or a light-emitting host compound may be used as long as it is generally used as a light-emitting layer compound.

[0177] As the luminescent compound of the above-mentioned luminescent layer, it includes but is not limited to phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e. TADF (also known as E-type delayed fluorescence), triplet-triplet quenching or compounds that can cause luminescence through a combination of these processes. The luminescent compound can be selected from a variety of materials according to the desired luminescent color. Non-limiting examples of the light-emitting compound include phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene and other fused ring derivatives, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, distyrene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, distyryl derivatives, distyryl arylene derivatives, diazinonacene derivatives, furan derivatives, benzofuran derivatives, isobenzofuran derivatives, dibenzofuran derivatives, coumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polyisocyanurate derivatives, Methyl derivatives, cyanine derivatives, oxobenzanthracene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, quinolone derivatives, acridine derivatives, oxazine derivatives, phenoxy derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furanopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyrrolmethyl derivatives, purple ring ketone derivatives, pyrrolopyrrole derivatives, square acid derivatives, bioanthrone derivatives, phenazine derivatives, acridone derivatives, denitroflavin derivatives, fluorene derivatives, benzofluorene derivatives, aromatic boron derivatives, aromatic nitrogen boron derivatives and metal complexes (complexes of metals such as Ir, Pt, Au, Eu, Ru, Re, Ag, Cu and heteroaromatic ligands, etc.), etc.For example, N1,N1,N6,N6-tetrakis(4-(1-silyl)phenyl)pyrene-1,6-diamine, 2,12-di-tert-butyl-5,9-bis(4-(tert-butyl)-butyl)phenyl)-7-(3,5-di-tert-butylphenyl)-5,9-dihydro-5,9-diaza-13b-boronaphtho[3,2,1-de]anthracene (t-DABNA-dtB), octaethylporphyrin platinum (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)pyridine iridium(III) (fac-Tris(2-(3-p-xylyl)phenyl)pyridine iridium(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(acac), Ir(DMP)3, Ir(M phq)3, Ir(phq)2tpy, fac-Ir(ppy)2Pc, Ir(dp)PQ2, Ir(Dpm)(Piq)2, Hex-Ir(piq)2(acac), Hex-Ir(piq)3, Ir(dmpq)3, Ir(dmpq)2(acac), FPQIrpic, FIrpic, etc.

[0178] As the host compound of the above-mentioned light-emitting layer, a light-emitting host, a hole transport host and an electron transport host or a combination thereof can be used. As non-limiting examples of the light-emitting host compound, condensed ring derivatives such as anthracene and pyrene, distyryl anthracene derivatives or distyryl benzene derivatives such as distyryl derivatives, tetraphenyl butadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzofluorene derivatives, N-phenyl carbazole derivatives, carbonitrile derivatives, etc. can be cited. As non-limiting examples of hole transport host substances, carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, triarylamine derivatives, indole carbazole derivatives and benzoxazine phenoxazine derivatives can be cited. As non-limiting examples of electron transport host substances, pyridine derivatives, triazine derivatives, phosphine oxide derivatives, benzofuran pyridine derivatives and dibenzoxazine derivatives can be cited. For example, including 9,10-bis(2-naphthyl)anthracene (ADN), tris(8-hydroxyquinoline)aluminum (Alq3), Balq (8-hydroxyquinoline beryllium salt), DPVBi (4,4'-bis(2,2-distyryl)-1,1'-biphenyl) series, spiro-DPVBi (spiro-4,4'-bis(2,2-distyryl)-1,1'-biphenyl), LiPBO (2-(2-benzoxazolyl))-phenol lithium salt), bis(biphenylvinyl)benzene, aluminum-quinoline metal complex, imidazole, thiazole, oxazole metal complex, etc.

[0179] The above-mentioned electron injection layer or electron transport layer compound is not particularly limited, and any compound can be used as long as it is generally used as an electron injection layer or electron transport layer compound. As non-limiting examples of the electron injection layer or electron transport layer compound, there can be mentioned pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, piperidone derivatives, coumarin derivatives, naphthylimide derivatives, anthraquinone derivatives, diphenylquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives, thiophene derivatives, triazole derivatives, thiadiazole derivatives, metal complexes of auxin derivatives, quinoline derivatives, quinoxaline derivatives, quinoxaline derivatives, polymers, gallium complexes, pyrazole derivatives, perfluorophenylene derivatives, triazine derivatives. Compounds, 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, naphthyridine derivatives, aldehyde-linked azine derivatives, carbazole derivatives, indole derivatives, phosphine oxide derivatives, distyryl derivatives, hydroxyquinoline metal complexes, hydroxyazole metal complexes, azomethine metal complexes, tropolone metal complexes, flavonol metal complexes, benzoquinoline metal complexes, metal salts, etc. These materials can be used alone, but it is also okay to mix them with other materials. For example, 2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, tris(8-hydroxyquinoline)aluminum (Alq3), LiF, Liq, Li2O, BaO, NaCl, CsF and other substances can be included.

[0180] An electron transport auxiliary layer may be formed between the electron transport layer and the light emitting layer. The hole blocking layer compound is not particularly limited, and any compound may be used as long as it is commonly used as an electron transport auxiliary layer compound. For example, the electron transport auxiliary layer may include a pyrimidine derivative or the like.

[0181] The organic light emitting diode according to an embodiment of the present invention may be a front-emitting diode or a back-emitting diode.

[0182] An organic light emitting diode according to an example of the present invention may be used in a display device.

[0183] The organic light emitting diode according to an example of the present invention may be applied to a transparent display device, a mobile display device, a flexible display device, etc., but is not limited thereto.

[0184] The following will describe the synthesis methods and examples of the above compounds by means of representative examples. However, the synthesis methods of the compounds of the present invention are not limited to the methods exemplified below, and the implementation of the present invention is not limited to the examples below.

[0185] Synthesis example:

[0186] The final product of the present invention can be synthesized as shown in the following reaction formula 1 (Buchwald-Hartwig Cross Coupling Reaction), but is not limited thereto.

[0187] Reaction 1:

[0188]

[0189] Under nitrogen flow, SUB1 (reactant 1) (53.95 mmol), SUB2 (reactant 2) (51.38 mmol), t-BuONa (102.76 mmol), Pd2(dba)3 (1.03 mmol), Sphos (2.06 mmol) and toluene were placed in a 500 mL flask and stirred and refluxed to react. After the reaction was completed, the organic layer was extracted with toluene and water. The extracted solution was treated with MgSO4 to remove residual water, concentrated under reduced pressure, purified by column chromatography and recrystallized to obtain the product.

[0190] Reaction formula 1-1:

[0191]

[0192] Using SUB1 and SUB2-1 as reactants 1 and 2, the product was synthesized and purified according to the preparation method of the above reaction formula 1 to obtain 23.7 g (yield 72%) of "Compound 93" as a product. m / z = 639.26 (C48H33NO = 639.80)

[0193] Reaction 1-2:

[0194]

[0195] Using SUB1 and SUB2-2 as reactants 1 and 2, the synthesis and purification were carried out according to the preparation method of the above reaction formula 1 to obtain 25.8 g (yield 74%) of "Compound 7" as the product. m / z = 679.29 (C51H37NO = 679.86)

[0196] Reaction 1-3:

[0197]

[0198] Using SUB1 and SUB2-3 as reactants 1 and 2, the synthesis and purification were carried out according to the preparation method of the above reaction formula 1 to obtain 23.5 g (yield 70%) of "Compound 11" as the product. m / z = 653.24 (C48H32NO2 = 653.78)

[0199] Reaction 1-4:

[0200]

[0201] Using SUB1 and SUB2-4 as reactants 1 and 2, the synthesis and purification were carried out according to the preparation method of the above reaction formula 1 to obtain 23.1 g (yield 67%) of "Compound 14" as the product. m / z = 669.21 (C48H31NOS = 669.84)

[0202] Reaction 1-5:

[0203]

[0204] Using SUB1 and SUB2-5 as reactants 1 and 2, the synthesis and purification were carried out according to the preparation method of the above reaction formula 1 to obtain 24.3 g (yield 65%) of "Compound 22" as the product. m / z = 728.28 (C54H36N2O = 728.90)

[0205] Reaction 1-6:

[0206]

[0207] Using SUB1 and SUB2-6 as reactants 1 and 2, the product was synthesized and purified according to the preparation method of the above reaction formula 1 to obtain 26.6 g (yield 71%) of "Compound 18" as a product. m / z = 728.28 (C54H36N2O = 728.90)

[0208] Reaction 1-7:

[0209]

[0210] Using SUB1 and SUB2-7 as reactants 1 and 2, the product was synthesized and purified according to the preparation method of the above reaction formula 1 to obtain 23.7 g (yield 67%) of "Compound 94" as a product. m / z = 689.27 (C52H35NO = 689.86)

[0211] Reaction 1-8:

[0212]

[0213] Using SUB1 and SUB2-8 as reactants 1 and 2, the synthesis and purification were carried out according to the preparation method of the above reaction formula 1 to obtain 23.0 g (yield 73%) of "Compound 24" as the product. m / z = 613.24 (C46H31NO = 613.76)

[0214] Reaction 1-9:

[0215]

[0216] Using SUB1 and SUB2-9 as reactants 1 and reactants, synthesis and purification were performed according to the preparation method of the above reaction formula 1 to obtain 25.6 g (yield 68%) of "Compound 53" as a product. m / z = 731.32 (C55H41NO = 731.94)

[0217] Reaction 1-10:

[0218]

[0219] Using SUB1 and SUB2-10 as reactants 1 and 2, the synthesis and purification were carried out according to the preparation method of the above reaction formula 1 to obtain 28.5 g (yield 75%) of "Compound 105" as the product. m / z = 739.29 (C56H37NO = 739.92)

[0220] The products are synthesized by the preparation method of the above reaction formula 1 using reactants 1 and reactants 2 as shown in Tables 1 to 8 below.

[0221] Table 1

[0222]

[0223]

[0224]

[0225]

[0226]

[0227] Table 2

[0228]

[0229]

[0230]

[0231] Table 3

[0232]

[0233]

[0234]

[0235]

[0236] Table 4

[0237]

[0238]

[0239]

[0240] Table 5

[0241]

[0242]

[0243]

[0244] Table 6

[0245]

[0246]

[0247]

[0248]

[0249] Table 7

[0250]

[0251]

[0252]

[0253] Table 8

[0254]

[0255]

[0256]

[0257] Experimental Example 1: Determination of HOMO and LUMO

[0258] The hole transport auxiliary layer plays a role in reducing the accumulation of holes at the interface of the light-emitting layer due to the HOMO energy level difference between the hole transport layer and the light-emitting layer. For this reason, preferably, the HOMO energy difference with the light-emitting layer is smaller than the HOMO energy level difference with the hole injection layer. In addition, it should have a higher LUMO energy level than the light-emitting layer to minimize the leakage of electrons from the light-emitting layer to the hole transport layer.

[0259] In order to confirm whether the compound represented by Chemical Formula 1 of the present invention is suitable as a hole transport auxiliary layer material, the HOMO energy level (eV) and LUMO energy level (eV) were calculated using Spartan software (B3LYP DFT 6-31G* by spartan'16) and are shown in Table 9 below.

[0260] Table 9

[0261]

[0262] Example 1: Preparation of organic light emitting diode (blue light emitting layer)

[0263] The substrate laminated with ITO (100nm) as the anode of the organic light-emitting diode is divided into cathode, anode area and insulating layer and patterned by the exposure (Photo-Lithograph) process, and then the surface is treated with UV-ozone (Ozone) treatment and O2:N2 plasma to achieve the purpose of cleaning and improving the work function of the anode (ITO).

[0264] Then, a mixture of 2-(7-Dicyanomethy lene-1,3,4,5,6,8,9,10-octafluoro-7H-pyren-2-ylidene)-malononitrile (NDP-9) and N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine in a ratio of 3:97 was deposited on the anode with a thickness of 10 nm as a hole injection layer (HIL). Next, 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) was vacuum deposited with a thickness of 100 nm on the upper portion of the hole injection layer as a hole transport layer, and compound 93 was formed with a thickness of 15 nm on the upper portion of the hole transport layer (HTL) as a hole transport auxiliary layer.

[0265] The 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-boranaphtho[3,2,1-de]anthracene (t-DABNA-dtB) was used as the dopant. A blue light emitting layer (EBL) was deposited on the upper portion of the hole transport auxiliary layer with a thickness of 25 nm, wherein the mixing ratio of the host:dopant was (weight standard) 97:3. On the blue light emitting layer (EML), 2-(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 were mixed in a weight ratio of 1:1 and deposited in a thickness of 25 nm as an electron transport layer (ETL). An electron injection layer (Liq) was deposited in a thickness of 1 nm on the upper portion of the electron transport layer (ETL), and a mixture of magnesium and silver mixed in a weight ratio of 1:4 was deposited in a thickness of 16 nm as a cathode. N4,N4'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD) is deposited on the cathode with a thickness of 60 nm as a capping layer. A seal cap containing a moisture absorbent is attached to the capping layer with a UV curable adhesive to form a protective film (encapsulation layer or protective layer) to prepare an organic light emitting diode, so that the organic light emitting diode is protected from oxygen or moisture in the atmosphere.

[0266] Comparative Examples 1 to 10

[0267] Except that the material of compound 93 used as the hole transport auxiliary layer material in the above example 1 was changed to the material shown in the following table 11, the organic light emitting diodes of comparative examples 1 to 10 were prepared respectively in the same manner as in the above example 1. The structures of compound A to compound J used as the hole transport auxiliary layer materials in comparative examples 1 to 10 are shown in the following table 10.

[0268] Example 2 to Example 181

[0269] The organic light emitting diodes of Examples 2 to 181 were prepared respectively in the same manner as in Example 1, except that the material of Compound 93 used as the hole transport auxiliary layer material in Example 1 was changed to the materials shown in Tables 12 to 19 below.

[0270] Experimental Example 2: Performance Evaluation of Organic Light Emitting Diodes (Blue Diodes)

[0271] For each of the organic light emitting diodes prepared in Examples 1 to 181 and Comparative Examples 1 to 10, a 10 mA / cm 2 The driving voltage and external quantum efficiency (EQE) (%) were measured using the McScience M6000 at 10 mA / cm 2 The lifetime (LT95) was measured by constant current driving of 100 Å to confirm the time required for the luminance to decrease from the initial luminance to the 95% level. The measurement results are shown in Tables 11 to 19 below.

[0272] Table 10

[0273]

[0274]

[0275] Table 11

[0276] Comparative Example Hole transport auxiliary layer materials Driving voltage(V) EQE(%) Life (LT95) (hrs) Comparative Example 1 Compound A 3.80 12.9 252 Comparative Example 2 Compound B 3.80 12.5 245 Comparative Example 3 Compound C 3.81 12.3 230 Comparative Example 4 Compound D 3.81 12.9 226 Comparative Example 5 Compound E 3.82 13.0 225 Comparative Example 6 Compound F 3.82 13.0 220 Comparative Example 7 Compound G 3.83 12.8 220 Comparative Example 8 Compound H 3.83 12.6 214 Comparative Example 9 Compound I 3.85 12.6 210 Comparative Example 10 Compound J 3.85 12.8 210

[0277] Table 12

[0278]

[0279]

[0280] Table 13

[0281]

[0282]

[0283] Table 14

[0284]

[0285]

[0286] Table 15

[0287]

[0288]

[0289] Table 16

[0290]

[0291]

[0292] Table 17

[0293]

[0294]

[0295] Table 18

[0296]

[0297]

[0298] Table 19

[0299]

[0300]

[0301] Example 182: Preparation of organic light emitting diode (green light emitting layer)

[0302] The substrate laminated with ITO (100nm) as the anode of the organic light-emitting diode is divided into cathode, anode area and insulating layer and patterned by the exposure (Photo-Lithograph) process, and then the surface is treated with UV-ozone (Ozone) treatment and O2:N2 plasma to achieve the purpose of cleaning and improving the work function of the anode (ITO).

[0303] A mixture of 2-(7-Dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyren-2-ylidene)-malononitrile (NDP-9) and N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine in a ratio of 3:97 was deposited on the anode with a thickness of 10 nm as a hole injection layer (HIL). Next, 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) was vacuum deposited with a thickness of 100 nm on the upper portion of the hole injection layer as a hole transport layer, and compound 93 was formed with a thickness of 15 nm on the upper portion of the hole transport layer (HTL) as a hole transport auxiliary layer.

[0304] A green light-emitting layer (EML) was deposited on the hole transport auxiliary layer with a thickness of 35 nm using 4,4-N,N'-dicarbazole-biphenyl (CBP) as the main body and Ir(ppy)3 [tris(2-phenylpyridine)-iridium] as the dopant, wherein the mixing ratio of the main body: dopant (weight standard) was 95:5. On the green light emitting layer (EML), 2-(4-(9,10-Di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole and Liq were mixed at a weight ratio of 1:1 and deposited at a thickness of 25 nm as an electron transport layer (ETL). Liq was deposited at a thickness of 1 nm on the upper portion of the electron transport layer (ETL) as an electron injection layer (EIL). Then, a mixture of magnesium and silver (Ag) mixed in a weight ratio of 1:4 was deposited as a cathode with a thickness of 16 nm, and N4,N4'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD) was deposited as a capping layer with a thickness of 60 nm on the cathode. A seal cap containing a moisture absorbent was attached to the capping layer with a UV curable adhesive to form a protective film (encapsulation layer or protective layer) to prepare an organic light emitting diode, so that the organic light emitting diode is protected from oxygen or moisture in the atmosphere.

[0305] Comparative Examples 11 to 20

[0306] The organic light emitting diodes of Comparative Examples 11 to 20 were prepared in the same manner as in Example 182, except that the material of Compound 93 used as the hole transport auxiliary layer material of Example 182 was changed to the material shown in Table 20 below. The structures of Compounds A to J used as hole transport auxiliary layer materials in Comparative Examples 11 to 20 are shown in Table 10 above.

[0307] Example 183 to Example 205

[0308] The organic light emitting diodes of Examples 183 to 205 were prepared respectively in the same manner as in Example 182, except that the material of Compound 93 used as the hole transport auxiliary layer material of Example 182 was changed to the material shown in Table 21 below.

[0309] Experimental Example 3: Performance Evaluation of Organic Light Emitting Diode (Green Diode)

[0310] For each organic light emitting diode prepared in the above-mentioned Examples 182 to 205 and Comparative Examples 11 to 20, the performance of the organic light emitting diode was evaluated by the same method as the above-mentioned Experimental Example 2, and the results are shown in the following Tables 20 and 21.

[0311] Table 20

[0312] Comparative Example Hole transport auxiliary layer materials Driving voltage(V) EQE(%) Life (LT95) (hrs) Comparative Example 11 Compound A 3.70 40.0 650 Comparative Example 12 Compound B 3.75 40.2 680 Comparative Example 13 Compound C 3.72 39.5 700 Comparative Example 14 Compound D 3.71 38.5 685 Comparative Example 15 Compound E 3.73 40.3 670 Comparative Example 16 Compound F 3.76 39.4 673 Comparative Example 17 Compound G 3.74 40.6 690 Comparative Example 18 Compound H 3.77 39.2 660 Comparative Example 19 Compound I 3.76 40.9 645 Comparative Example 20 Compound J 3.78 40.1 640

[0313] Table 21

[0314]

[0315]

[0316] Since the compound represented by Chemical Formula 1 of the present invention has a specific structural form as described above, compared with the comparative example compound that does not satisfy the structure of Chemical Formula 1, the hole injection characteristics are adjusted to reduce the accumulation of holes at the interface of the hole transport auxiliary layer and the light-emitting layer, thereby reducing the quenching phenomenon of excitons being quenched by polarons at the interface of the hole transport auxiliary layer and the light-emitting layer. As a result, it is confirmed that the degradation phenomenon of the diode can be reduced and stabilized compared with the comparative example compound, so when applied to a device, the driving voltage is reduced and the efficiency and life are improved.

[0317] Although the preferred embodiments of the present invention are described in detail above, the protection scope of the present invention is not limited thereto. Various changes and improvements made by ordinary technicians in this field using the basic concepts of the present invention defined in the protection scope of the invention claims belong to the protection scope of the present invention.

Claims

1. An organic compound represented by the following chemical formula 1, characterized in that: Chemical formula 1: In the above chemical formula 1, L1 to L3 are each independently one selected from the group consisting of a single bond, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, and a substituted or unsubstituted heteroarylalkyl group having 6 to 60 carbon atoms, R1 to R 16 and Ar1 are the same as or different from each other and are each independently selected from hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxyl, trimethylsilylethynyl, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl having 3 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 30 carbon atoms, substituted or unsubstituted cycloalkynyl having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 5 to 60 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 60 carbon atoms one selected from the group consisting of a heteroarylalkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylalkylamino group having 7 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 5 to 60 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, and a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, Ar2 is a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, Optionally, when the above L1 to L3, R1 to R 16 When Ar1 and Ar2 are substituted, they can be selected from deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxyl, trimethylsilylethynyl, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, alkenyl having 2 to 30 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, alkynyl having 2 to 30 carbon atoms, cycloalkynyl having 3 to 20 carbon atoms, aryl having 6 to 30 carbon atoms, aralkyl having 7 to 30 carbon atoms, heteroaryl having 5 to 60 carbon atoms, heteroaralkyl having 6 to 60 carbon atoms, amino, 1 to The present invention is substituted with one or more substituents selected from the group consisting of an alkylamino group having 30 carbon atoms, an aralkylamino group having 7 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, a heteroarylamino group having 5 to 60 carbon atoms, a silyl group, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms and an arylthio group having 6 to 30 carbon atoms. When a plurality of the above substituents are present, the above substituents may be the same or different from each other.

2. The organic compound according to claim 1, characterized in that The above R7 is a substituent represented by the following chemical formula 2, Chemical formula 2: In the above chemical formula 2, * represents a binding site, n is an integer from 0 to 5, R 17 Each of them can be independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms.

3. The organic compound according to claim 1, characterized in that The above Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

4. The organic compound according to claim 1, characterized in that The above Ar2 is one of the substituents represented by the following Chemical Formula 3 to Chemical Formula 5, Chemical formula 3: Chemical formula 4: Chemical formula 5: In the above Chemical Formulae 3 to 5, * represents a binding site, o is an integer from 0 to 5, p is an integer from 0 to 7, q is an integer from 0 to 9, R 18 To R 20 Each of them can be independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms.

5. The organic compound according to claim 1, characterized in that The above Ar1 is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

6. The organic compound according to claim 1, characterized in that The above Chemical Formula 1 is selected from the following Chemical Formulas 6 to 13, Chemical formula 6: Chemical formula 7: Chemical formula 8: Chemical formula 9: Chemical formula 10: Chemical formula 11: Chemical formula 12: Chemical formula 13: In the above Chemical Formulas 6 to 13, L2, L3, R 11 To R 16 , Ar1 and Ar2 are as defined in the chemical formula 1, R 21 To R 33 The same as or different from each other and are each independently selected from hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxyl, trimethylsilylethynyl, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl having 3 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 30 carbon atoms, substituted or unsubstituted cycloalkynyl having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 5 to 60 carbon atoms, substituted or unsubstituted heteroaryl having 6 to 60 carbon atoms One of the group consisting of an alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 7 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 5 to 60 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms and a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms.

7. The organic compound according to claim 1, characterized in that The above Chemical Formula 1 is selected from the following Chemical Formulas 14 to 45, Chemical formula 14: Chemical formula 15: Chemical formula 16: Chemical formula 17: Chemical formula 18: Chemical formula 19: Chemical formula 20: Chemical formula 21: Chemical formula 22: Chemical formula 23: Chemical formula 24: Chemical formula 25: Chemical formula 26: Chemical formula 27: Chemical formula 28: Chemical formula 29: Chemical formula 30: Chemical formula 31: Chemical formula 32: Chemical formula 33: Chemical formula 34: Chemical formula 35: Chemical formula 36: Chemical formula 37: Chemical formula 38: Chemical formula 39: Chemical formula 40: Chemical formula 41: Chemical formula 42: Chemical formula 43: Chemical formula 44: Chemical formula 45: In the above Chemical Formulas 14 to 45, L3, R 11 To R 16 and Ar1 is as defined in the chemical formula 1, R 21 To R 42 The same as or different from each other and are each independently selected from hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxyl, trimethylsilylethynyl, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl having 3 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 30 carbon atoms, substituted or unsubstituted cycloalkynyl having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 5 to 60 carbon atoms, substituted or unsubstituted heteroaryl having 6 to 60 carbon atoms One of the group consisting of an alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 7 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 5 to 60 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms and a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms.

8. An organic light emitting diode, characterized in that: include: anode; a cathode, disposed opposite to the anode; and One or more organic layers are disposed between the anode and the cathode. At least one of the organic layers contains the organic compound according to claim 1 .

9. The organic light emitting diode according to claim 8, characterized in that: The organic layer comprising the organic compound according to claim 1 is a hole transport auxiliary layer.

10. The organic light emitting diode according to claim 8, characterized in that: The organic layer further includes at least one selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

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