Condensed ring compound and organic light-emitting device containing the same

Abstract

The present specification provides a compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

Description

Technical Field

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2018-0161787 filed in the Korean Intellectual Property Office on December 14, 2018, the entire contents of which are incorporated herein by reference.

[0002] The present specification relates to a compound and an organic light-emitting device including the same. Background Art

[0003] An organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to an organic light-emitting device having such a structure, electrons and holes injected from the two electrodes combine and pair in the organic thin film, and light is emitted when these annihilate. The organic thin film can be formed into a single layer or multiple layers as needed.

[0004] The organic light emitting phenomenon generally refers to the phenomenon of converting electrical energy into light energy using organic materials. An organic light emitting device utilizing the organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often formed into a multilayer structure formed of different materials to improve the efficiency and stability of the organic light emitting device. For example, the organic material layer may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in such an organic light emitting device structure, holes and electrons are injected from the anode and the cathode into the organic material layer, respectively, and when the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons fall back to the ground state.

[0005] There is an ongoing need to develop new materials for such organic light emitting devices.

[0006] Prior art literature

[0007] (Patent Document 1) Korean Patent Application Publication No. 10-2012-032572 Summary of the invention

[0008] Technical issues

[0009] This specification describes compounds and organic light-emitting devices including the same.

[0010] Technical Solution

[0011] One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[0012] [Chemical formula 1]

[0013]

[0014] In Chemical Formula 1,

[0015] X is O or S, and

[0016] One or more of R9 to R16 are connected to * of the following Chemical Formula 2, and the rest of R9 to R16 not connected to Chemical Formula 2 and R1 to R8 are the same as or different from each other, and are each independently hydrogen, deuterium, cyano, nitro, carbonyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, or bond with an adjacent group to form a substituted or unsubstituted benzene ring,

[0017] [Chemical formula 2]

[0018]

[0019] In chemical formula 2,

[0020] A1 to A3 are the same as or different from each other and are each independently N or CR, and one or more of A1 to A3 is N,

[0021] L1 and L2 are the same as or different from each other and are each independently a direct bond, a substituted or unsubstituted cycloalkylene group, or a substituted or unsubstituted arylene group,

[0022] L3 is a direct bond, a substituted or unsubstituted cycloalkylene group, or a substituted or unsubstituted arylene group,

[0023] One or more of Ar1 and Ar2 are substituted or unsubstituted bicyclic or more fused aryl groups, and the others are the same as or different from each other and are each independently substituted or unsubstituted aryl groups, or substituted or unsubstituted heterocyclic groups,

[0024] R are the same as or different from each other and are each independently hydrogen, deuterium, cyano, nitro, carbonyl, substituted or unsubstituted silyl, substituted or unsubstituted boronyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclyl, and

[0025] m1 to m3 are each an integer of 0 to 3, and when m1 to m3 are each 2 or more, two or more substituents in brackets are the same as or different from each other.

[0026] Another embodiment of the present specification provides an organic light emitting device including: a first electrode; a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers includes the above compound.

[0027] Beneficial Effects

[0028] According to one embodiment of the present specification, the compound represented by Chemical Formula 1 may be used as a material of an organic material layer of an organic light emitting device.

[0029] When an organic light emitting device including the compound represented by Chemical Formula 1 according to one embodiment of the present specification is manufactured, an organic light emitting device having low driving voltage, high efficiency, and long lifetime may be obtained. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] Figures 1 to 8 An example of an organic light-emitting device is shown.

[0031] [reference numerals]

[0032] 1: substrate / 2: anode / 3: hole injection layer / 4: hole transport layer / 5: light-emitting layer / 6: hole blocking layer / 7: layer for simultaneous electron transport and electron injection / 8: cathode / 9: electron blocking layer / 11: first hole transport layer / 12: first electron blocking layer / 13: first light-emitting layer / 14: first electron transport layer / 15: N-type charge generation layer / 16: P-type charge generation layer / 17: second hole transport layer / 18: second light-emitting layer Light layer / 19: Second electron transport layer / 20: Third hole transport layer / 21: Third light-emitting layer / 22: Third electron transport layer / 111, 202: Hole transport layer 1 / 112, 208: Hole transport layer 2 / 113, 204, 303-3: Blue fluorescent light-emitting layer 1 / 114, 205, 304: Electron transport layer 1 / 115, 206: N-type charge generation layer 1 / 116: P-type charge generation layer 1 / 117, 21 4: Hole transport layer 3 / 118, 303-1: Red phosphorescent light emitting layer / 119: Yellow-green phosphorescent light emitting layer / 120, 303-2: Green phosphorescent light emitting layer / 121, 211: Electron transport layer 2 / 122, 212: N-type charge generation layer 2 / 123, 201, 207, 213, 301: P-doped hole transport layer / 124: Hole transport layer 4 / 125: Hole transport layer 5 / 126, 210: Blue phosphorescent light emitting layer Light emitting layer 2 / 127, 217: Electron transport layer 3 / 128, 218, 306: Electron injection layer / 129: Cover layer / 203: Hole transport layer 1-1 / 209: Hole transport layer 2-1 / 215: Hole transport layer 3-1 / 216: Blue fluorescent light emitting layer 3 / 302-1: Red hole transport layer / 302-2: Green hole transport layer / 302-3: Blue hole transport layer / 305: Electron transport layer 1-1 DETAILED DESCRIPTION

[0033] Hereinafter, the present specification will be described in more detail.

[0034] One embodiment of the present specification provides a compound represented by the following Chemical Formula 1. In the compound represented by the following Chemical Formula 1, the fluorene part of the spirofluorene xanthene derivative is bonded to a N-containing monocyclic ring, and a bicyclic or more ring-condensed aryl group is bonded to the N-containing monocyclic ring.

[0035] When the fluorene part of the spirofluorene xanthene derivative is bonded to the N-containing monocyclic ring instead of the xanthene part in the compound represented by the following Chemical Formula 1, LUMO is delocalized to the N-containing monocyclic ring by the non-conjugated effect of the heteroatom (O or S) and the electron donor, and the compound having the N-containing monocyclic ring connected to the xanthene part has an excessively high LUMO energy value compared to the compound having the N-containing monocyclic ring bonded to the fluorene part instead of the xanthene part. Therefore, when the compound having the N-containing monocyclic ring connected to the xanthene part is included in an organic light-emitting device, electrons cannot be smoothly injected from the cathode due to the high LUMO energy value, and the voltage is greatly increased and the efficiency is reduced when the device is driven.

[0036] In addition, since the compound represented by the following chemical formula 1 contains a bicyclic or more ring-fused aromatic group (one or more of Ar1 and Ar2) as an essential component, a compound having a large difference (ΔEST) between a singlet energy (S1) value and a triplet energy (T1) value can be obtained, and when a compound having a large difference (ΔEST) between a singlet energy (S1) value and a triplet energy (T1) value is used in a device, a life improvement effect can be obtained. Specifically, a large difference between a singlet energy (S1) value and a triplet energy (T1) value means that the overlap between molecular orbitals (HOMO and LUMO) in the molecule is large. Since the degree of overlap between molecular orbitals (HOMO and LUMO) increases, the bond strength between atoms in the molecule becomes rigid due to the absence of structural steric hindrance, and therefore, a life improvement effect can be obtained when used in a device.

[0037] [Chemical formula 1]

[0038]

[0039] In Chemical Formula 1,

[0040] X is O or S, and

[0041] One or more of R9 to R16 are connected to * of the following Chemical Formula 2; and the rest of R9 to R16 not connected to Chemical Formula 2 and R1 to R8 are the same as or different from each other, and are each independently hydrogen, deuterium, cyano, nitro, carbonyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, or bond with an adjacent group to form a substituted or unsubstituted benzene ring,

[0042] [Chemical formula 2]

[0043]

[0044] In chemical formula 2,

[0045] A1 to A3 are the same as or different from each other and are each independently N or CR, and one or more of A1 to A3 is N,

[0046] L1 and L2 are the same as or different from each other and are each independently a direct bond, a substituted or unsubstituted cycloalkylene group, or a substituted or unsubstituted arylene group,

[0047] L3 is a direct bond, a substituted or unsubstituted cycloalkylene group, or a substituted or unsubstituted arylene group,

[0048] One or more of Ar1 and Ar2 are substituted or unsubstituted bicyclic or more fused aryl groups, and the others are the same as or different from each other and are each independently substituted or unsubstituted aryl groups, or substituted or unsubstituted heterocyclic groups,

[0049] R are the same as or different from each other and are each independently hydrogen, deuterium, cyano, nitro, carbonyl, substituted or unsubstituted silyl, substituted or unsubstituted boronyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclyl, and

[0050] m1 to m3 are each an integer of 0 to 3, and when m1 to m3 are each 2 or more, two or more substituents in brackets are the same as or different from each other.

[0051] In the present specification, unless specifically described to the contrary, a description that a part “includes” certain constituent elements means that other constituent elements can also be included, and other constituent elements are not excluded.

[0052] In this specification, description that one member is placed “on” another member includes not only a case where one member is in contact with another member but also a case where another member exists between the two members.

[0053] In the present specification, "a substituent in brackets" means a substituent described in a symbol represented by '()'. Specifically, in '(W)', a substituent in brackets means 'W', and "two or more substituents in brackets are the same or different from each other" means that when two W are present, the types of the two W are the same or different from each other.

[0054] Examples of the substituent in the present specification will be described below, however, the substituent is not limited thereto.

[0055] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed into another substituent, and the position of substitution is not limited as long as it is a position where a hydrogen atom is substituted (i.e., a position where a substituent can be substituted), and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0056] In this specification, the term "substituted or unsubstituted" means substituted by one, two or more substituents selected from the following: deuterium (-D), halogen groups, cyano groups, nitro groups, carbonyl groups, hydroxyl groups, silyl groups, boron groups, alkoxy groups, alkyl groups, aryloxy groups, cycloalkyl groups, aryl groups, and heterocyclic groups, or substituted by substituents connected by two or more substituents in the substituents exemplified above, or having no substituents. For example, "substituents connected by two or more substituents" can include biphenyl groups. In other words, the biphenyl group can be an aryl group, or it can be interpreted as a substituent connected by two phenyl groups.

[0057] Examples of the substituent will be described below, however, the substituent is not limited thereto.

[0058] In the present specification, examples of the halogen group may include fluorine (—F), chlorine (—Cl), bromine (—Br), or iodine (—I).

[0059] In the present specification, the silyl group may be represented by a chemical formula -SiYaYbYc, and Ya, Yb, and Yc may each be hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group.

[0060] The silyl group may be an alkylsilyl group, an arylsilyl group, an arylalkylsilyl group, etc. The alkylsilyl group means that one or more of Ya, Yb, and Yc are substituted or unsubstituted alkyl groups and the remainder is hydrogen, the arylsilyl group means that one or more of Ya, Yb, and Yc are substituted or unsubstituted aryl groups and the remainder is hydrogen, and the arylalkylsilyl group means that one or more of Ya, Yb, and Yc are substituted or unsubstituted alkyl groups, one or more of the remainder are substituted or unsubstituted aryl groups, and the further remainder is hydrogen. Specific examples of the silyl group may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, ethyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, dimethylphenylsilyl, methyldiphenylsilyl, etc., but are not limited thereto.

[0061] In the present specification, the carbonyl group may be represented by -C(=O)Yf, and Yf ​​may be a substituent such as an alkyl group having 1 to 40 carbon atoms or an aryl group having 6 to 60 carbon atoms, but is not limited thereto.

[0062] In the present specification, the boron group can be represented by the chemical formula -BYdYe, and Yd and Ye can each be hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group. Specific examples of the boron group can include dimethylboryl, diethylboryl, tert-butyldimethylboryl, diphenylboryl, phenylboryl, etc., but are not limited thereto.

[0063] In the present specification, the alkyl group may be linear or branched. The number of carbon atoms of the alkyl group is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10.

[0064] Specific examples of the alkyl group may include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, etc., and the alkyl group may be linear or branched. According to one embodiment, the propyl group includes normal propyl and isopropyl, and the butyl group includes normal butyl, isobutyl and tert-butyl.

[0065] In the present specification, the alkoxy group may be linear or branched. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20. Specific examples thereof may include methoxy, ethoxy, n-propoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but are not limited thereto.

[0066] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the carbon number of the cycloalkyl group is 3 to 30. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specific examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0067] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 39. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. When the aryl group is a monocyclic aryl group, examples thereof may include phenyl, biphenyl, terphenyl, quaterphenyl, etc., but are not limited thereto. Examples of polycyclic aryl groups may include naphthyl, anthracenyl, phenanthren ... Phi, pyrene, base, phenylene, fluorenyl, triphenylene, fluoranthene, etc., but not limited thereto.

[0068] In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro ring structure.

[0069] When the fluorenyl group is substituted, it may include a spirofluorenyl group such as spirocyclopentanefluorene and spirobifluorene; or a substituted fluorenyl group such as 9,9-dimethylfluorenyl and 9,9-diphenylfluorenyl. However, the structure is not limited thereto.

[0070] In the present specification, the heterocyclic group is a cyclic group containing one or more of N, O, S and Si as a heteroatom, and although not particularly limited thereto, the number of carbon atoms is preferably 2 to 60. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group may include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a quinolyl group, a pyridazinyl group, a triazinyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothienyl group, an indenocarbazolyl group, an indolocarbazolyl group, a spiroxanthenyl group Spirofluorene Thioxanthenyl 9,9-Dimethylthiazolidine etc., but not limited to.

[0071] In the present specification, the description provided above regarding the heterocyclic group may be applied to the heteroaryl group, except that the heteroaryl group is aromatic.

[0072] In the present specification, the description provided above regarding the cycloalkyl group may be applied to the cycloalkylene group, except that the cycloalkylene group is divalent.

[0073] In the present specification, the description provided above regarding the aryl group may be applied to the arylene group, except that the arylene group is divalent.

[0074] In the present specification, the description provided above regarding the heteroaryl group may be applied to the heteroarylene group, except that the heteroarylene group is divalent.

[0075] In the present specification, the bicyclic or more ring-condensed aryl group means a substituent formed by fusing two or more aromatic hydrocarbon rings, and examples thereof may include naphthyl, phenanthrenyl, phenalkenyl, triphenylene, fluoranthenyl and the like, but are not limited thereto.

[0076] In the present specification, in a substituted or unsubstituted ring formed by bonding with an adjacent group, "ring" means a hydrocarbon ring or a heterocyclic ring.

[0077] The hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a condensed ring of an aromatic ring and an aliphatic ring, and may be selected from examples of a cycloalkyl group or an aryl group, except that the hydrocarbon ring is not monovalent.

[0078] In the present specification, the description provided above regarding the aryl group may be applied to the aromatic hydrocarbon ring, except that the aromatic hydrocarbon ring is not monovalent.

[0079] The description provided above for heterocyclyl can be applied to heterocycle, except that the heterocycle is not monovalent.

[0080] According to one embodiment of the present specification, X is O or S.

[0081] In one embodiment of the present specification, A1 to A3 are the same as or different from each other and are each independently N or CR, and one or more of A1 to A3 are N.

[0082] According to another embodiment, two or more of A1 to A3 are N, and the rest are CR.

[0083] In another embodiment, two or three of A1 to A3 are N, and the rest are CR.

[0084] According to one embodiment of the present specification, R is hydrogen, deuterium, cyano, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclyl group having 2 to 30 carbon atoms.

[0085] According to another embodiment, R is hydrogen or deuterium.

[0086] In one embodiment of the present specification, one or more of R9 to R16 are connected to * of Chemical Formula 2, and the rest of R9 to R16 not connected to Chemical Formula 2 and R1 to R8 are the same as or different from each other, and are each independently hydrogen, deuterium, cyano, nitro, carbonyl, substituted or unsubstituted trialkylsilyl having 1 to 20 carbon atoms, substituted or unsubstituted diarylboryl having 6 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 20 carbon atoms. The present invention relates to a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms and containing one or more of O, S and N as a heteroatom, or is bonded to an adjacent group to form a substituted or unsubstituted benzene ring.

[0087] In another embodiment, one or more of R9 to R16 are connected to * of Chemical Formula 2, and the rest of R9 to R16 not connected to Chemical Formula 2 and R1 to R8 are the same as or different from each other and are each independently hydrogen; deuterium; cyano; carbonyl; trialkylsilyl having 1 to 20 carbon atoms; alkyl having 1 to 20 carbon atoms which is unsubstituted or substituted with a halogen group; aryloxy having 6 to 30 carbon atoms; cycloalkyl having 3 to 30 carbon atoms; unsubstituted or substituted with one or more of the following Substituted aryl group having 6 to 30 carbon atoms: cyano group, diarylboryl group having 6 to 30 carbon atoms, alkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms which is unsubstituted or substituted with a halogen group, and heteroaryl group having 2 to 30 carbon atoms; or heterocyclic group having 2 to 30 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms and contains one or more of O, S and N as a heteroatom, or bonds with an adjacent group to form a substituted or unsubstituted benzene ring.

[0088] According to another embodiment, one or more of R9 to R16 are connected to * of Chemical Formula 2, and the rest of R9 to R16 not connected to Chemical Formula 2 and R1 to R8 are the same as or different from each other, and are each independently hydrogen; deuterium; cyano; carbonyl; trimethylsilyl; methyl which is unsubstituted or substituted with a halogen group; propyl; butyl; phenoxy; cyclohexyl; phenyl which is unsubstituted or substituted with a cyano group, a diphenylboryl group, a methyl group, a trifluoromethoxy group or a pyridyl group; biphenyl; naphthyl; dibenzofuranyl; carbazolyl; benzofuranyl; or methylbenzimidazolyl, or bonded to an adjacent group to form a benzene ring.

[0089] According to one embodiment of the present specification, in Chemical Formula 1, when adjacent two groups of R1 to R8 and the rest of R9 to R16 not connected to Chemical Formula 2 are bonded to each other to form a benzene ring, the following structure may be obtained, however, the structure is not limited thereto.

[0090]

[0091] According to one embodiment of the present specification, one or more of R9 to R16 are connected to * of the following Chemical Formula 2.

[0092] According to one embodiment of the present specification, one or more of R9, R11, R14 or R16 among R9 to R16 are connected to * of the following Chemical Formula 2.

[0093] [Chemical formula 2]

[0094]

[0095] In chemical formula 2,

[0096] A1 to A3 are the same as or different from each other and are each independently N or CR, and one or more of A1 to A3 is N,

[0097] L1 and L2 are the same as or different from each other and are each independently a direct bond, a substituted or unsubstituted cycloalkylene group, or a substituted or unsubstituted arylene group,

[0098] L3 is a direct bond, a substituted or unsubstituted cycloalkylene group, or a substituted or unsubstituted arylene group,

[0099] One or more of Ar1 and Ar2 are substituted or unsubstituted bicyclic or more fused aryl groups, and the others are the same as or different from each other and are each independently substituted or unsubstituted aryl groups, or substituted or unsubstituted heterocyclic groups,

[0100] R are the same as or different from each other and are each independently hydrogen, deuterium, cyano, nitro, carbonyl, substituted or unsubstituted silyl, substituted or unsubstituted boronyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclyl, and

[0101] m1 to m3 are each an integer of 0 to 3, and when m1 to m3 are each 2 or more, two or more substituents in brackets are the same as or different from each other.

[0102] According to one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted cycloalkylene group having 3 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

[0103] According to another embodiment, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted cycloalkylene group having 3 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0104] In another embodiment, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted cyclohexylene, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted fluorenylene, or a substituted or unsubstituted naphthylene.

[0105] In another embodiment, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a cyclohexylene group, a phenylene group which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, a biphenylene group which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, a fluorenylene group which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, or a naphthylene group which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

[0106] According to another embodiment, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a cyclohexylene group, an unsubstituted or methyl-substituted phenylene group, an unsubstituted or methyl-substituted biphenylene group, an unsubstituted or methyl-substituted fluorenylene group, or an unsubstituted or methyl-substituted naphthylene group.

[0107] In one embodiment of the present specification, L3 is a direct bond, a substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

[0108] According to another embodiment, L3 is a direct bond, a substituted or unsubstituted cycloalkylene group having 3 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0109] In another embodiment, L3 is a direct bond, substituted or unsubstituted cyclohexylene, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorenylene, or substituted or unsubstituted naphthylene.

[0110] According to another embodiment, L3 is a direct bond, a phenylene group which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, a biphenylene group which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, a fluorenyl group which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, or a naphthyl group which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

[0111] According to another embodiment, L3 is a direct bond, cyclohexylene, unsubstituted or methyl-substituted phenylene, unsubstituted or methyl-substituted biphenylene, unsubstituted or methyl-substituted fluorenylene, or unsubstituted or methyl-substituted naphthylene.

[0112] In Chemical Formula 1, the N-containing monocyclic ring and the spirofluorene xanthene are connected by a linking group L3, and when L3 is a divalent heterocyclic group, since the heterocyclic ring has excessively chemically weighted electron donor and acceptor capabilities on one side, the heterocyclic ring excessively increases or decreases the LUMO value of the N-containing monocyclic ring, resulting in a significant change in the electron injection ability or electron transport ability of the light-emitting layer when used in a device, and therefore, the driving voltage, efficiency and life characteristics of the device are deteriorated due to the destruction of the balance between holes and electrons in the device.

[0113] In addition, unlike the case where one or more of Ar1 and Ar2 contain a bicyclic or more ring-condensed aromatic group, when Ar1 and Ar2 are monocyclic aromatic groups and L3 is a bicyclic or more ring-condensed aromatic group in Chemical Formula 1 of the present application, steric hindrance (high distortion) of the spirofluorene xanthene and the monocyclic ring containing N is caused in the structure, resulting in weak bond strength between atoms in the molecule, and in addition, the degree of overlap between molecular orbitals (HOMO and LUMO) in the molecule becomes small. This results in poor device characteristics not only in terms of the driving voltage and efficiency of the device, but also in terms of life span.

[0114] According to one embodiment of the present specification, one or more of Ar1 and Ar2 is any one of the following structures, and the rest are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0115]

[0116] In the structure described,

[0117] R21 to R30 are the same as or different from each other, and are each independently hydrogen, deuterium, cyano, nitro, carbonyl, substituted or unsubstituted silyl, substituted or unsubstituted boronyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclyl,

[0118] n1 is an integer from 0 to 7, n2 is an integer from 0 to 9, n3 and n6 are each an integer from 0 to 6, n4, n5 and n9 are each an integer from 0 to 3, n7 is an integer from 0 to 4, n8 is an integer from 0 to 5, n10 is an integer from 0 to 8, and when n1 to n10 are each 2 or more, two or more substituents in brackets are the same as or different from each other, and

[0119] * refers to the attachment site.

[0120] According to one embodiment of the present specification, one or more of Ar1 and Ar2 is a substituted or unsubstituted bicyclic or more ring-condensed aryl group, and the rest is a substituted or unsubstituted heterocyclic group.

[0121] According to one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted bicyclic or multicyclic condensed aromatic group.

[0122] According to one embodiment of the present specification, one or more of Ar1 and Ar2 is a substituted or unsubstituted bicyclic or more fused aryl group having 12 to 60 carbon atoms, and the rest are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms and containing one or more of O, S, Si and N as a heteroatom.

[0123] According to one embodiment of the present specification, one or more of Ar1 and Ar2 is a substituted or unsubstituted bicyclic or more ring-condensed aromatic group having 12 to 60 carbon atoms, and the remainder is a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms and containing one or more of O, S, Si and N as a heteroatom.

[0124] According to one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted bicyclic or more ring-condensed aromatic group having 12 to 60 carbon atoms.

[0125] According to another embodiment, one or more of Ar1 and Ar2 are substituted or unsubstituted bicyclic or higher ring condensed aryl groups having 12 to 60 carbon atoms, and the rest are the same as or different from each other and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms and containing one or more of O, S, Si and N as heteroatoms.

[0126] According to another embodiment, one or more of Ar1 and Ar2 is a substituted or unsubstituted bicyclic or higher ring condensed aryl group having 12 to 60 carbon atoms, and the rest is a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms and containing one or more of O, S, Si and N as a heteroatom.

[0127] According to another embodiment, one or more of Ar1 and Ar2 are substituted or unsubstituted bicyclic or more fused aryl groups having 12 to 60 carbon atoms, and the rest are the same or different from each other and are each independently an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with one or more substituents selected from an alkyl group having 1 to 20 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms which is unsubstituted or substituted with one or more substituents selected from an alkyl group having 1 to 20 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms and containing one or more of O, S, N or Si as a heteroatom. The heteroaryl group contains O, S, N or Si as a heteroatom.

[0128] According to another embodiment, one or more of Ar1 and Ar2 are substituted or unsubstituted bicyclic or more fused aryl groups having 12 to 60 carbon atoms, and the remainder are heterocyclic groups having 2 to 30 carbon atoms and containing one or more of O, S, N or Si as heteroatoms, which are unsubstituted or substituted with one or more substituents selected from alkyl groups having 1 to 20 carbon atoms and heteroaryl groups having 2 to 30 carbon atoms. The heteroaryl group contains O, S, N or Si as heteroatoms.

[0129] In another embodiment, one or more of Ar1 and Ar2 are substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, or substituted or unsubstituted fluoranthenyl, and the rest are the same or different from each other and are each independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted silyl, substituted or unsubstituted spiroxanthenyl. Substituted or unsubstituted spirofluorene thioxanthenyl substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted pyridinyl.

[0130] In another embodiment, one or more of Ar1 and Ar2 is substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, or substituted or unsubstituted fluoranthenyl, and the rest is substituted or unsubstituted silyl, substituted or unsubstituted spiroxanthenyl. Substituted or unsubstituted spirofluorene thioxanthenyl substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted pyridinyl.

[0131] In another embodiment, Ar1 and Ar2 are the same as or different from each other, and are each independently substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenalkenyl, substituted or unsubstituted triphenylene, or substituted or unsubstituted fluoranthenyl.

[0132] According to another embodiment, one or more of Ar1 and Ar2 is unsubstituted or substituted with one or more substituents selected from the following naphthyl: alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 30 carbon atoms, and heterocyclic groups having 2 to 30 carbon atoms; phenanthrenyl, unsubstituted or substituted with one or more substituents selected from the following: alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 30 carbon atoms, and heterocyclic groups having 2 to 30 carbon atoms; phenanthrenyl, unsubstituted or substituted with one or more substituents selected from the following: alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 30 carbon atoms, and heterocyclic groups having 2 to 30 carbon atoms; triphenylene, unsubstituted or substituted with one or more substituents selected from the following: alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 30 carbon atoms, and heterocyclic groups having 2 to 30 carbon atoms; or unsubstituted or substituted with one or more substituents selected from the following Fluoranthene substituted with substituents: alkyl having 1 to 20 carbon atoms, aryl having 6 to 30 carbon atoms, and heterocyclic group having 2 to 30 carbon atoms, and the rest are the same or different from each other, and each is independently unsubstituted or substituted with one or more substituents selected from the following phenyl: alkyl having 1 to 20 carbon atoms and heteroaryl having 2 to 30 carbon atoms; biphenyl unsubstituted or substituted with one or more substituents selected from the following: alkyl having 1 to 20 carbon atoms and heteroaryl having 2 to 30 carbon atoms; terphenyl unsubstituted or substituted with one or more substituents selected from the following: alkyl having 1 to 20 carbon atoms and heteroaryl having 2 to 30 carbon atoms; silolyl unsubstituted or substituted with one or more substituents selected from the following: alkyl having 1 to 20 carbon atoms and heteroaryl having 2 to 30 carbon atoms; spirofluorenyl unsubstituted or substituted with one or more substituents selected from the following Alkyl groups having 1 to 20 carbon atoms and heteroaryl groups having 2 to 30 carbon atoms; spirofluorenylthioxanthenyl groups which are unsubstituted or substituted with one or more substituents selected from the following an alkyl group having 1 to 20 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms; a dibenzofuranyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms; or a pyridyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms.

[0133] According to another embodiment, one or more of Ar1 and Ar2 is unsubstituted or substituted with one or more substituents selected from the group consisting of naphthyl, alkyl, 6 to 30 carbon atoms, aryl, and heterocyclic groups having 2 to 30 carbon atoms; phenanthrenyl, unsubstituted or substituted with one or more substituents selected from the group consisting of alkyl, 6 to 30 carbon atoms, and heterocyclic groups having 2 to 30 carbon atoms; phenanthrenyl, unsubstituted or substituted with one or more substituents selected from the group consisting of alkyl, 6 to 30 carbon atoms, and heterocyclic groups having 2 to 30 carbon atoms; phenanthrenyl, unsubstituted or substituted with one or more substituents selected from the group consisting of alkyl, 6 to 30 carbon atoms, and heterocyclic groups having 2 to 30 carbon atoms. ; triphenylene which is unsubstituted or substituted with one or more substituents selected from the following: an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms; or fluoranthene which is unsubstituted or substituted with one or more substituents selected from the following: an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms, and the remainder is silolyl which is unsubstituted or substituted with one or more substituents selected from the following: an alkyl group having 1 to 20 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms; spirofluorenyl which is unsubstituted or substituted with one or more substituents selected from the following Alkyl groups having 1 to 20 carbon atoms and heteroaryl groups having 2 to 30 carbon atoms; spirofluorenylthioxanthenyl groups which are unsubstituted or substituted with one or more substituents selected from the following an alkyl group having 1 to 20 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms; a dibenzofuranyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms; or a pyridyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms.

[0134] According to another embodiment, Ar1 and Ar2 are identical to or different from each other and are each independently a naphthyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms; a phenanthrenyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms; a phenanthrenyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of substituted phenalenyl: an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms; a triphenylene group which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms; or a fluoranthenyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms.

[0135] According to another embodiment, one or more of Ar1 and Ar2 are unsubstituted or substituted with one or more substituents selected from the following: naphthyl, methyl, phenyl, naphthyl and pyridyl; phenanthrenyl, unsubstituted or substituted with one or more substituents selected from the following: methyl, phenyl, naphthyl and pyridyl; phenanthrenyl, unsubstituted or substituted with one or more substituents selected from the following: methyl, phenyl, naphthyl and pyridyl; triphenylene, unsubstituted or substituted with one or more substituents selected from the following: methyl, phenyl, naphthyl and pyridyl; or fluoranthenyl, unsubstituted or substituted with one or more substituents selected from the following: methyl, phenyl, naphthyl and pyridyl, and the rest are the same or different from each other and are each independently phenyl, unsubstituted or substituted with dibenzofuranyl or pyridyl; biphenyl; terphenyl, unsubstituted or substituted with methyl or phenyl; 9,9-dimethylthiazolyl; spirofluorenyl Spirofluorene Thioxanthenyl dibenzofuranyl; or pyridinyl.

[0136] According to another embodiment, one or more of Ar1 and Ar2 are unsubstituted or substituted with one or more substituents selected from the following naphthyl: methyl, phenyl, naphthyl and pyridyl; unsubstituted or substituted with one or more substituents selected from the following phenanthrenyl: methyl, phenyl, naphthyl and pyridyl; unsubstituted or substituted with one or more substituents selected from the following phenanthrenyl: methyl, phenyl, naphthyl and pyridyl; unsubstituted or substituted with one or more substituents selected from the following triphenylene: methyl, phenyl, naphthyl and pyridyl; or unsubstituted or substituted with one or more substituents selected from the following fluoranthenyl: methyl, phenyl, naphthyl and pyridyl, and the remainder is 9,9-dimethylthiazolyl; spirofluorenyl Spirofluorene Thioxanthenyl dibenzofuranyl; or pyridinyl.

[0137] According to another embodiment, Ar1 and Ar2 are the same as or different from each other and are each independently naphthyl which is unsubstituted or substituted with one or more substituents selected from the group consisting of methyl, phenyl, naphthyl and pyridyl; phenanthrenyl which is unsubstituted or substituted with one or more substituents selected from the group consisting of methyl, phenyl, naphthyl and pyridyl; phenanthrenyl which is unsubstituted or substituted with one or more substituents selected from the group consisting of methyl, phenyl, naphthyl and pyridyl; triphenylene which is unsubstituted or substituted with one or more substituents selected from the group consisting of methyl, phenyl, naphthyl and pyridyl; or fluoranthenyl which is unsubstituted or substituted with one or more substituents selected from the group consisting of methyl, phenyl, naphthyl and pyridyl.

[0138] According to one embodiment of the present specification, one or more of Ar1 and Ar2 is a substituted or unsubstituted bicyclic or more ring-fused aromatic group. When an N-type heterocycle (e.g., a cyclic compound containing an N atom) is included instead of a bicyclic or more ring-fused aromatic group, the electron affinity becomes too high and the LUMO of the monocyclic ring containing N becomes too low, and when the compound is included in a layer (e.g., an electron transport layer) between the light-emitting layer and the cathode of an organic light-emitting device according to one embodiment of the present specification, the electron transport ability to the light-emitting layer or the hole blocking layer is reduced, thereby increasing the barrier to the light-emitting layer, and therefore, an increase in driving voltage, a decrease in efficiency, and a decrease in lifespan occur in the device. In addition, compounds to which a P-type heterocycle or a monocyclic aromatic group is bonded instead of a bicyclic or more ring-fused aromatic group result in a decrease in device life due to a relatively small difference (ΔEST) between the singlet energy (S1) value and the triplet energy (T1) value.

[0139] According to one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 3 to 8.

[0140] [Chemical formula 3]

[0141]

[0142] [Chemical formula 4]

[0143]

[0144] [Chemical formula 5]

[0145]

[0146] [Chemical formula 6]

[0147]

[0148] [Chemical formula 7]

[0149]

[0150] [Chemical formula 8]

[0151]

[0152] In Chemical Formulas 3 to 8,

[0153] X, R1 to R8, A1 to A3, L1 to L3 and m1 to m3 have the same definitions as in Chemical Formula 1,

[0154] Ar3 is a substituted or unsubstituted bicyclic or more fused aryl group, a substituted or unsubstituted monocyclic aryl group, or a substituted or unsubstituted heterocyclic group,

[0155] R21 to R30 are the same as or different from each other, and are each independently hydrogen, deuterium, cyano, nitro, carbonyl, substituted or unsubstituted silyl, substituted or unsubstituted boronyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclyl,

[0156] R32 is hydrogen, deuterium, cyano, nitro, carbonyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, or bonds with an adjacent group to form a substituted or unsubstituted benzene ring,

[0157] n1 is an integer from 0 to 7, n2 is an integer from 0 to 9, n3 and n6 are each an integer from 0 to 6, n4, n5 and n9 are each an integer from 0 to 3, n7 is an integer from 0 to 4, n8 is an integer from 0 to 5, n10 is an integer from 0 to 8, and when n1 to n10 are each 2 or more, two or more substituents in brackets are the same as or different from each other, and

[0158] p1 is an integer of 0 to 7, and when p1 is 2 or more, two or more R32 are the same as or different from each other.

[0159] According to one embodiment of the present specification, Ar3 is a substituted or unsubstituted bicyclic or more ring-condensed aryl group, a substituted or unsubstituted monocyclic aryl group, or a substituted or unsubstituted heterocyclic group.

[0160] According to one embodiment of the present specification, Ar3 is a substituted or unsubstituted bicyclic or more ring-condensed aromatic group having 12 to 60 carbon atoms; a substituted or unsubstituted monocyclic aromatic group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms and containing one or more of O, S, Si and N as a heteroatom.

[0161] According to another embodiment, Ar3 is a substituted or unsubstituted bicyclic or more ring-condensed aryl group having 12 to 60 carbon atoms; a substituted or unsubstituted monocyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms and containing one or more of O, S, Si and N as heteroatoms.

[0162] According to another embodiment, Ar3 is a substituted or unsubstituted bicyclic or more fused aryl group having 12 to 60 carbon atoms; a monocyclic aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with one or more substituents selected from an alkyl group having 1 to 20 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms which is unsubstituted or substituted with one or more substituents selected from an alkyl group having 1 to 20 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms and contains one or more of O, S, N or Si as a heteroatom. The heteroaryl group contains O, S, N or Si as a heteroatom.

[0163] In another embodiment, Ar3 is substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted silolyl, substituted or unsubstituted spiroxanthenyl. Substituted or unsubstituted spirofluorene thioxanthenyl substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted pyridinyl.

[0164] According to another embodiment, Ar3 is a naphthyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms; a phenanthrenyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms; a phenanthrenyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms; a triphenylene group which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms; Fluoranthene group substituted with more substituents: alkyl group having 1 to 20 carbon atoms, aryl group having 6 to 30 carbon atoms, and heterocyclic group having 2 to 30 carbon atoms; phenyl group which is unsubstituted or substituted with one or more substituents selected from the following: alkyl group having 1 to 20 carbon atoms and heteroaryl group having 2 to 30 carbon atoms; biphenyl group which is unsubstituted or substituted with one or more substituents selected from the following: alkyl group having 1 to 20 carbon atoms and heteroaryl group having 2 to 30 carbon atoms; terphenyl group which is unsubstituted or substituted with one or more substituents selected from the following: alkyl group having 1 to 20 carbon atoms and heteroaryl group having 2 to 30 carbon atoms; silyl group which is unsubstituted or substituted with one or more substituents selected from the following: alkyl group having 1 to 20 carbon atoms and heteroaryl group having 2 to 30 carbon atoms; spirofluorenyl group which is unsubstituted or substituted with one or more substituents selected from the following Alkyl groups having 1 to 20 carbon atoms and heteroaryl groups having 2 to 30 carbon atoms; spirofluorenylthioxanthenyl groups which are unsubstituted or substituted with one or more substituents selected from the following an alkyl group having 1 to 20 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms; a dibenzofuranyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms; or a pyridyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms.

[0165] According to another embodiment, Ar3 is unsubstituted or substituted with one or more substituents selected from the group consisting of naphthyl, methyl, phenyl, naphthyl and pyridyl; phenanthrenyl, unsubstituted or substituted with one or more substituents selected from the group consisting of methyl, phenyl, naphthyl and pyridyl; phenanthrenyl, unsubstituted or substituted with one or more substituents selected from the group consisting of methyl, phenyl, naphthyl and pyridyl; triphenylene, unsubstituted or substituted with one or more substituents selected from the group consisting of methyl, phenyl, naphthyl and pyridyl; fluoranthenyl, unsubstituted or substituted with one or more substituents selected from the group consisting of methyl, phenyl, naphthyl and pyridyl; phenyl, unsubstituted or substituted with dibenzofuranyl or pyridyl; biphenyl; terphenyl, unsubstituted or substituted with methyl or phenyl; 9,9-dimethylthiazolyl; spirofluorenyl Spirofluorene Thioxanthenyl dibenzofuranyl; or pyridinyl.

[0166] According to one embodiment of the present specification, R21 to R30 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms and containing O, S, N or Si as a heteroatom.

[0167] In another embodiment, R21 to R30 are the same as or different from each other, and are each independently hydrogen; deuterium; substituted or unsubstituted methyl; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl; or substituted or unsubstituted pyridinyl.

[0168] According to another embodiment, R21 to R30 are the same as or different from each other, and are each independently hydrogen; deuterium; methyl; phenyl; biphenyl; naphthyl; or pyridyl.

[0169] According to another embodiment, n1 to n10 are each 0 or 1.

[0170] According to one embodiment of the present specification, R32 has the same definition as the rest of R9 to R16 that are not connected to the above Chemical Formula 2.

[0171] According to one embodiment of the present specification, in Chemical Formula 3, Ar3 is a substituted or unsubstituted bicyclic or more ring-condensed aromatic group; or a substituted or unsubstituted heterocyclic group.

[0172] According to one embodiment of the present specification, in Chemical Formula 3, Ar3 is a substituted or unsubstituted bicyclic or more fused aromatic group having 12 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms and including one or more of O, S, Si and N as a heteroatom.

[0173] According to one embodiment of the present specification, in Chemical Formula 3, Ar3 is a substituted or unsubstituted bicyclic or more fused aromatic group having 12 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms and including one or more of O, S, Si and N as a heteroatom.

[0174] According to one embodiment of the present specification, in Chemical Formula 3, Ar3 is a substituted or unsubstituted bicyclic or more fused aryl group having 12 to 60 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms and containing one or more of O, S, N or Si as a heteroatom, which is unsubstituted or substituted with one or more substituents selected from an alkyl group having 1 to 20 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms. The heteroaryl group contains O, S, N or Si as a heteroatom.

[0175] According to one embodiment of the present specification, in Chemical Formula 3, Ar3 is a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluoranthenyl group; a substituted or unsubstituted thiophene group; a substituted or unsubstituted spiroxanthenyl group; Substituted or unsubstituted spirofluorene thioxanthenyl substituted or unsubstituted dibenzofuranyl; or substituted or unsubstituted pyridinyl.

[0176] According to one embodiment of the present specification, in Chemical Formula 3, Ar3 is a naphthyl group which is unsubstituted or substituted with one or more substituents selected from the following: an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms; a phenanthrenyl group which is unsubstituted or substituted with one or more substituents selected from the following: an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms; a phenanthrenyl group which is unsubstituted or substituted with one or more substituents selected from the following: an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms; heterocyclic group; triphenylene group which is unsubstituted or substituted with one or more substituents selected from the following: alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 30 carbon atoms, and heterocyclic groups having 2 to 30 carbon atoms; fluoranthene group which is unsubstituted or substituted with one or more substituents selected from the following: alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 30 carbon atoms, and heterocyclic groups having 2 to 30 carbon atoms; silolyl group which is unsubstituted or substituted with one or more substituents selected from the following: alkyl groups having 1 to 20 carbon atoms and heteroaryl groups having 2 to 30 carbon atoms; spirofluorenyl group which is unsubstituted or substituted with one or more substituents selected from the following Alkyl groups having 1 to 20 carbon atoms and heteroaryl groups having 2 to 30 carbon atoms; spirofluorenylthioxanthenyl groups which are unsubstituted or substituted with one or more substituents selected from the following an alkyl group having 1 to 20 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms; a dibenzofuranyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms; or a pyridyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms.

[0177] According to one embodiment of the present specification, in Chemical Formula 3, Ar3 is unsubstituted or substituted with one or more substituents selected from the following naphthyl: methyl, phenyl, naphthyl and pyridyl; unsubstituted or substituted with one or more substituents selected from the following phenanthrenyl: methyl, phenyl, naphthyl and pyridyl; unsubstituted or substituted with one or more substituents selected from the following phenanthrenyl: methyl, phenyl, naphthyl and pyridyl; unsubstituted or substituted with one or more substituents selected from the following triphenylene: methyl, phenyl, naphthyl and pyridyl; unsubstituted or substituted with one or more substituents selected from the following fluoranthenyl: methyl, phenyl, naphthyl and pyridyl; 9,9-dimethylthiazolyl; spirofluorenyl Spirofluorene Thioxanthenyl dibenzofuranyl; or pyridinyl.

[0178] According to one embodiment of the present specification, Chemical Formula 3 is represented by the following Chemical Formula 3-1.

[0179] [Chemical formula 3-1]

[0180]

[0181] In Chemical Formula 3-1, the substituents have the same definitions as in Chemical Formula 3.

[0182] According to one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following structures.

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192] According to one embodiment of the present specification, the compound represented by Chemical Formula 1 satisfies the following Formula 1.

[0193] [Formula 1]

[0194] ΔESTC El >ΔEST El

[0195] In formula 1,

[0196] ΔEST C El is the difference between the singlet energy (S1) value and the triplet energy (T1) value of the compound represented by Chemical Formula 1, and

[0197] ΔEST El is the difference between the singlet energy (S1) value and the triplet energy (T1) value of the compound in which Ar1 and Ar2 in the compound represented by Chemical Formula 1 do not include a bicyclic or higher ring condensed aromatic group.

[0198] Formula 1 means that the difference between the S1 energy value and the T1 energy value of the compound of Chemical Formula 1 of the present application having a bicyclic or more ring-condensed aromatic group (one or more of Ar1 and Ar2) as an essential component is greater than the difference between the S1 value and the T1 value of the compound having the same core structure as the compound of the present disclosure but not including the bicyclic or more ring-condensed aromatic group in Ar1 and Ar2 of the present application. Since the compound represented by Chemical Formula 1 includes a bicyclic or more ring-condensed aromatic group (one or more of Ar1 and Ar2) in the compound, the difference between the S1 energy value and the T1 energy value is large, and therefore, when used in a device, a device having excellent life characteristics can be obtained.

[0199] According to one embodiment of the present specification, the compound represented by Chemical Formula 1 satisfies the following Formula 3. When the compound represented by Chemical Formula 1 satisfies the following Formula 3, when used in a device, a device having highly excellent lifespan characteristics may be obtained.

[0200] [Formula 3]

[0201] ΔESTC El -ΔEST El >0.05eV

[0202] In formula 3,

[0203] ΔEST C El is the difference between the singlet energy (S1) value and the triplet energy (T1) value of the compound represented by Chemical Formula 1, and

[0204] ΔEST El is the difference between the singlet energy (S1) value and the triplet energy (T1) value of the compound in which Ar1 and Ar2 in the compound represented by Chemical Formula 1 do not include a bicyclic or higher ring condensed aromatic group.

[0205] Formula 3 can be obtained by 0.05eV<ΔESTC El -ΔEST El Indicated by <1.00eV.

[0206] According to one embodiment of the present specification, the compound represented by Chemical Formula 1 satisfies the following Formula 2.

[0207] [Formula 2]

[0208] 0.30eV<ΔESTC El <1.5eV

[0209] In formula 2,

[0210] ΔESTC El is the difference between the singlet energy (S1) value and the triplet energy (T1) value of the compound represented by Chemical Formula 1.

[0211] In the calculation of the singlet energy (S1) and triplet energy (T1) in this specification, molecular structure optimization and calculation of each energy can be performed using Gaussian (a quantum chemical calculation program manufactured by Gaussian, Inc.) by using the B3PW91 functional and 6-31G * The density functional theory (DFT) of the basis functions is used to obtain the

[0212] In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by Chemical Formula 1. In addition, in the present specification, the HOMO energy level and LUMO energy level of the compound can also be adjusted by introducing various substituents into the core structure having the above structure.

[0213] In addition, an organic light-emitting device according to the present specification includes a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers contains the above-mentioned compound.

[0214] The organic material layer includes a first stack including one or more light emitting layers and a second stack including one or more charge generation layers between the first stack and the second stack.

[0215] In addition, the organic material layer includes a first stack, a second stack and a third stack, and one or more charge generating layers are respectively included between the first stack and the second stack, and between the second stack and the third stack, the first stack includes one or more light-emitting layers, the second stack includes one or more light-emitting layers, and the third stack includes one or more light-emitting layers.

[0216] The one or more charge generation layers may be an N-type charge generation layer and a P-type charge generation layer, and the N-type charge generation layer and the P-type charge generation layer may be disposed adjacent to each other.

[0217] The N-type charge generation layer may include both the benzimidazolophenanthridine-based derivative and a metal such as Li.

[0218] The P-type charge generation layer may contain both the arylamine-based derivative and the cyano group-containing compound.

[0219] The first stack, the second stack and the third stack each include one or more light-emitting layers, and may also include one or more layers of a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole blocking layer, a layer that simultaneously performs hole transport and hole injection, and a layer that simultaneously performs electron transport and electron injection.

[0220] The organic light-emitting device of the present specification may be manufactured using a common organic light-emitting device manufacturing method and materials, except that one or more organic material layers are formed using the compound represented by Chemical Formula 1 above.

[0221] When manufacturing an organic light-emitting device in which an organic material layer including the compound represented by Chemical Formula 1 is formed, a solution coating method as well as a vacuum deposition method may be used when forming the organic material layer. Herein, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited thereto.

[0222] The organic material layer of the organic light-emitting device of the present specification may be formed as a single-layer structure, but may also be formed as a multilayer structure in which two or more organic material layers are laminated. For example, the organic light-emitting device of the present disclosure may have a structure including a hole transport layer, a hole injection layer, an electron blocking layer, a layer that simultaneously performs hole transport and hole injection, an electron transport layer, an electron injection layer, a hole blocking layer, and a layer that simultaneously performs electron transport and electron injection as an organic material layer. However, the structure of the organic light-emitting device of the present specification is not limited thereto, and may include a smaller or larger number of organic material layers.

[0223] According to one embodiment of the present specification, the organic material layer includes a light-emitting layer, the light-emitting layer includes a host and a dopant, and the maximum light-emitting wavelength of the dopant is 400 nm to 520 nm.

[0224] According to another embodiment, the dopant of the light-emitting layer is a blue fluorescent dopant.

[0225] According to one embodiment of the present specification, the organic material layer includes two or more light-emitting layers, and at least one of the two or more light-emitting layers includes a blue fluorescent dopant.

[0226] According to another embodiment, at least two of the two or more light-emitting layers have different maximum emission wavelengths.

[0227] In another embodiment, at least one of the two or more light-emitting layers comprises a phosphorescent dopant and at least one of the others comprises a fluorescent dopant.

[0228] When the organic light-emitting device includes two or more light-emitting layers, each light-emitting layer may be Figures 3 to 7 As shown, the light-emitting layers may be stacked vertically. Figure 8 Horizontally laminated as shown.

[0229] In the organic light-emitting device of the present specification, the organic material layer includes a hole transport layer, a hole injection layer, or a layer that simultaneously performs hole transport and hole injection, and the hole transport layer, the hole injection layer, or the layer that simultaneously performs hole transport and hole injection may contain the compound represented by Chemical Formula 1 above.

[0230] In another organic light-emitting device of the present specification, the organic material layer includes an electron transport layer, an electron injection layer, or a layer that simultaneously performs electron transport and electron injection, and the electron transport layer, the electron injection layer, or the layer that simultaneously performs electron transport and electron injection may contain the compound represented by Chemical Formula 1 above.

[0231] According to another embodiment, the compound represented by Chemical Formula 1 is included in an electron transport layer, an electron injection layer, or a layer that simultaneously performs electron transport and electron injection, and a blue fluorescent dopant may be included in a light emitting layer.

[0232] In another organic light-emitting device of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer may include the compound represented by Chemical Formula 1 above.

[0233] According to another embodiment, the organic material layer includes a light emitting layer, and the light emitting layer may include the compound represented by Chemical Formula 1 as a host of the light emitting layer.

[0234] According to another embodiment, the organic material layer includes a light emitting layer, and the light emitting layer may include the compound represented by Chemical Formula 1 as a dopant.

[0235] In one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a host and a dopant. Here, based on 100 parts by weight of the host, the dopant may be included in an amount of 1 to 20 parts by weight, preferably 1 to 10 parts by weight.

[0236] In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

[0237] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0238] The organic light-emitting device of the present specification may have Figures 1 to 8 The structure is shown, however, the structure is not limited thereto.

[0239] Figure 1The structure of an organic light-emitting device is shown in which an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, a hole blocking layer 6, a layer 7 for simultaneous electron transport and electron injection, and a cathode 8 are sequentially laminated on a substrate 1. In such a structure, the compound represented by Chemical Formula 1 may be contained in the layer 7 for simultaneous electron transport and electron injection.

[0240] Figure 2 The structure of an organic light-emitting device is shown in which an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 9, a light-emitting layer 5, a layer 7 for simultaneous electron transport and electron injection, and a cathode 8 are sequentially laminated on a substrate 1. In such a structure, the compound represented by Chemical Formula 1 may be contained in the layer 7 for simultaneous electron transport and electron injection.

[0241] Figure 3 The structure of an organic light-emitting device is shown in which an anode 2, a hole injection layer 3, a first hole transport layer 11, a first electron blocking layer 12, a first light-emitting layer 13, a first electron transport layer 14, an N-type charge generation layer 15, a P-type charge generation layer 16, a second hole transport layer 17, a second light-emitting layer 18, a layer 7 for simultaneous electron transport and electron injection, and a cathode 8 are sequentially laminated on a substrate 1. In such a structure, the compound represented by Chemical Formula 1 may be contained in the layer 7 for simultaneous electron transport and electron injection.

[0242] Figure 4 The structure of an organic light-emitting device in which an anode 2, a hole injection layer 3, a first hole transport layer 11, a first electron blocking layer 12, a first light-emitting layer 13, a first electron transport layer 14, an N-type charge generation layer 15, a P-type charge generation layer 16, a second hole transport layer 17, a second light-emitting layer 18, a second electron transport layer 19, an N-type charge generation layer 15, a P-type charge generation layer 16, a third hole transport layer 20, a third light-emitting layer 21, a third electron transport layer 22, and a cathode 8 are sequentially laminated on a substrate 1 is shown. In such a structure, the compound represented by Chemical Formula 1 may be contained in the first electron transport layer 14 and the third electron transport layer 22.

[0243] Figure 5The structure of an organic light-emitting device is shown in which an anode 2, a hole injection layer 3, a hole transport layer 1 111, a hole transport layer 2 112, a blue fluorescent light-emitting layer 1 113, an electron transport layer 1 114, an N-type charge generation layer 1 115, a P-type charge generation layer 1 116, a hole transport layer 3 117, a red phosphorescent light-emitting layer 118, a yellow-green phosphorescent light-emitting layer 119, a green phosphorescent light-emitting layer 120, an electron transport layer 2 121, an N-type charge generation layer 2 122, a p-doped hole transport layer 123, a hole transport layer 4 124, a hole transport layer 5 125, a blue fluorescent light-emitting layer 2 126, an electron transport layer 3 127, an electron injection layer 128, a cathode 8 and a covering layer 129 are sequentially laminated on a substrate 1. In such a structure, the compound represented by Chemical Formula 1 may be included in one or more of the electron transport layer 3 127 , the electron transport layer 2 121 , and the electron transport layer 1 114 .

[0244] Figure 6 The structure of an organic light-emitting device in which an anode 2, a hole injection layer 3, a hole transport layer 1 111, a hole transport layer 2 112, a blue fluorescent light-emitting layer 1 113, an electron transport layer 1 114, an N-type charge generation layer 1 115, a P-type charge generation layer 1 116, a hole transport layer 3 117, a red phosphorescent light-emitting layer 118, a green phosphorescent light-emitting layer 120, an electron transport layer 2 121, an N-type charge generation layer 2 122, a p-doped hole transport layer 123, a hole transport layer 4 124, a hole transport layer 5 125, a blue fluorescent light-emitting layer 2 126, an electron transport layer 3 127, an electron injection layer 128, a cathode 8, and a capping layer 129 are sequentially laminated on a substrate 1 is shown. In such a structure, the compound represented by Chemical Formula 1 may be contained in one or more of the electron transport layer 3 127, the electron transport layer 2 121, and the electron transport layer 1 114.

[0245] Figure 7The structure of an organic light-emitting device is shown in which an anode 2, a p-doped hole transport layer 201, a hole transport layer 1 202, a hole transport layer 1-1 203, a blue fluorescent light-emitting layer 1 204, an electron transport layer 1 205, an N-type charge generation layer 1 206, a p-doped hole transport layer 207, a hole transport layer 2 208, a hole transport layer 2-1 209, a blue fluorescent light-emitting layer 2 210, an electron transport layer 2 211, an N-type charge generation layer 2 212, a p-doped hole transport layer 213, a hole transport layer 3 214, a hole transport layer 3-1 215, a blue fluorescent light-emitting layer 3 216, an electron transport layer 3 217, an electron injection layer 218, a cathode 8 and a covering layer 129 are sequentially laminated on a substrate 1. In such a structure, the compound represented by Chemical Formula 1 may be included in one or more of the electron transport layer 3 217 , the electron transport layer 2 211 , and the electron transport layer 1 205 .

[0246] Figure 8 The structure of an organic light-emitting device in which an anode 2, a p-doped hole transport layer 301, a hole transport layer 302-1, 302-2, 302-3, a light-emitting layer 303-1, 303-2, 303-3, an electron transport layer 1 to 304, an electron transport layer 1-1 to 305, an electron injection layer 306, a cathode 8, and a capping layer 129 are sequentially laminated on a substrate 1 is shown. In such a structure, the compound represented by Chemical Formula 1 may be contained in one or more of the electron transport layer 1 to 304 and the electron transport layer 1-1 to 305.

[0247] For example, the organic light-emitting device according to the present specification can be manufactured by forming an anode on a substrate by depositing a metal, a conductive metal oxide, or an alloy thereof using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation, forming an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, an electron transport layer, an electron injection layer, etc. on the anode, and then depositing a material that can be used as a cathode on the organic material layer. In addition to such a method, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0248] The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a layer for simultaneous hole injection and hole transport, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer for simultaneous electron injection and electron transport, etc., but is not limited thereto, and may have a single-layer structure. In addition, various polymer materials may be used to form the organic material layer into a smaller number of layers using a solvent method instead of a deposition method. The solution method may be a method such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer.

[0249] The anode is an electrode for injecting holes. As the anode material, a material having a large work function is generally preferred so that the hole injection into the organic material layer is smooth. Specific examples of anode materials that can be used in the present disclosure include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, but not limited thereto.

[0250] The cathode is an electrode for injecting electrons. As the cathode material, a material having a small work function is generally preferred so that electrons can be injected smoothly into the organic material layer. Specific examples of cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO 2 / Al; and so on, but not limited to.

[0251] The hole injection layer is a layer that performs the function of promoting the injection of holes from the anode to the light-emitting layer. The hole injection material is a material that can advantageously receive holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on organic materials, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, etc., but are not limited thereto.

[0252] The hole transport layer can perform the role of promoting hole transport. As the hole transport material, such a material is suitable: it can receive holes from the anode or the hole injection layer, move the holes to the light-emitting layer, and has a high hole mobility. Specific examples thereof include organic materials based on arylamine, conductive polymers, block copolymers having both conjugated parts and non-conjugated parts, etc., but are not limited thereto.

[0253] The electron blocking layer may be provided between the hole transport layer and the light emitting layer. As the electron blocking layer, materials known in the art may be used.

[0254] The light-emitting layer may emit red, green or blue light and may be formed of a phosphorescent material or a fluorescent material. The light-emitting material is a material that can emit light in the visible light region by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the holes and electrons, and is preferably a material having a favorable quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include: 8-hydroxyquinoline aluminum complex (Alq 3 ); carbazole-based compounds; diphenylethylene-based compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoquinoline-based azoles, benzothiazole-based and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorenes; rubrene; and the like, but are not limited thereto.

[0255] The host material of the light-emitting layer includes fused aromatic ring derivatives, heterocyclic compounds, etc. Specifically, the fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., however, the materials are not limited thereto.

[0256] When the light-emitting layer emits red light, the following can be used as the light-emitting dopant: a phosphorescent material such as bis(1-phenylisoquinoline)iridium acetylacetonate (PIQIr(acac)), bis(1-phenylquinoline)iridium acetylacetonate (PQIr(acac)), tris(1-phenylquinoline)iridium (PQIr), or platinum octaethylporphyrin (PtOEP); or a fluorescent material such as tris(8-hydroxyquinoline)aluminum (Alq 3 ), however, the light-emitting dopant is not limited thereto. When the light-emitting layer emits green light, the following can be used as the light-emitting dopant: a phosphorescent material, such as face tris(2-phenylpyridine)iridium (Ir(ppy) 3 ); or fluorescent materials, such as tris(8-hydroxyquinoline)aluminum (Alq 3 ), anthracene-based compounds, pyrene-based compounds or boron-based compounds, however, the luminescent dopant is not limited thereto. When the luminescent layer emits blue light, the following can be used as the luminescent dopant: phosphorescent materials, such as (4,6-F2ppy) 2 Irpic; or a fluorescent material such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarene (DSA), a PFO-based polymer, a PPV-based polymer, an anthracene-based compound, a pyrene-based compound or a boron-based compound, however, the light-emitting dopant is not limited thereto.

[0257] The electron transport layer can perform the role of promoting electron transport. As the electron transport material, such a material is suitable: it can advantageously receive electrons from the cathode, move the electrons to the light-emitting layer, and has a high electron mobility. Specific examples thereof include: Al complexes of 8-hydroxyquinoline; Alq 3 complexes; organic free radical compounds; hydroxyflavonoid-metal complexes, etc., but not limited thereto.

[0258] The electron injection layer can perform the role of promoting electron injection. The electron injection material is preferably a compound that has the ability to transport electrons, has the effect of injecting electrons from the cathode, has an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from moving to the hole injection layer, and also has excellent thin film forming ability. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, Tetracarboxylic acid, fluorenyl methane, anthrone, etc., and derivatives thereof; metal complex compounds; nitrogen-containing 5-membered ring derivatives; etc., but not limited thereto.

[0259] As the layer that simultaneously performs electron transport and electron injection, the compound of the present disclosure or a material known in the art may be used, and when the compound of the present disclosure is included, a compound such as lithium quinolate (LiQ) may also be included.

[0260] The metal complex compounds include 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) chlorogallium, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, bis(2-methyl-8-quinoline)(2-naphthol) gallium, and the like, but are not limited thereto.

[0261] The hole blocking layer is a layer that blocks holes from reaching the cathode and can generally be formed under the same conditions as the hole injection layer. Specifically, it includes Oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., however, the hole blocking layer is not limited thereto.

[0262] The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a dual emission type according to the materials used.

[0263] Embodiments of the invention

[0264] Hereinafter, this specification will be described in detail with reference to the embodiments to specifically describe this specification. However, the embodiments according to this specification can be modified into various other forms, and the scope of this application should not be interpreted as being limited to the embodiments described below. The embodiments of this specification are provided to more fully describe this specification to those of ordinary skill in the art.

[0265] <Synthesis Example 1> Preparation of a compound represented by Compound 1

[0266]

[0267] (1) Preparation of Chemical Formula 1A

[0268] 4-Bromo-9H-fluoren-9-one (10 g, 38.6 mmol), phenol (7.25 g, 77.2 mmol) and excess phosphorus oxychloride (POCl 3 ) was refluxed at 120°C. After the resultant was cooled to room temperature, an excess of ethanol was introduced therein, and the resultant was filtered. The filtered solid was dissolved in pyridine, and the resultant was heated, cooled to room temperature, and then filtered. The resultant was recrystallized with chloroform and ethyl acetate to obtain Chemical Formula 1A (14 g, yield 87%).

[0269] MS:[M+H] + =411

[0270] (2) Preparation of Compound 1

[0271] After mixing Chemical Formula 1A (10 g, 24.3 mmol), Chemical Formula 1B-triazine boronic acid (9.82 g, 24 mmol) and potassium carbonate (K 2 CO 3 ) (10 g, 72.9 mmol) was dissolved in tetrahydrofuran (THF) (300 mL) and H 2 O (100 ml), and the resultant was heated to 90° C. Tetrakis(triphenylphosphine)palladium (Pd(PPh 3 ) 4 ) (0.56 g, 0.48 mmol), and the resultant was refluxed for 4 hours. After the resultant was cooled to room temperature, the aqueous layer was removed. Magnesium sulfate (MgSO 4 ), and the resultant was filtered. The resultant was concentrated and then purified by column chromatography to obtain Compound 1 (10 g, yield 67%).

[0272] MS:[M+H] + =613

[0273] <Synthesis Example 2> Preparation of a compound represented by Compound 2

[0274]

[0275] Compound 2 (11 g, yield 74%) was obtained in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Chemical Formula 2B was used instead of Chemical Formula 1B.

[0276] MS:[M+H] + =613

[0277] <Synthesis Example 3> Preparation of the compound represented by Compound 3

[0278]

[0279] Compound 3 (13 g, yield 81%) was obtained in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Chemical Formula 3B was used instead of Chemical Formula 1B.

[0280] MS:[M+H] + =663

[0281] <Synthesis Example 4> Preparation of the compound represented by Compound 4

[0282]

[0283]

[0284] Compound 4 (12.5 g, yield 78%) was obtained in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Chemical Formula 4B was used instead of Chemical Formula 1B.

[0285] MS:[M+H] + =663

[0286] <Synthesis Example 5> Preparation of the compound represented by Compound 5

[0287]

[0288] Compound 5 (9 g, yield 60%) was obtained in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Chemical Formula 2A was used instead of Chemical Formula 1A.

[0289] MS:[M+H] + =613

[0290] <Synthesis Example 6> Preparation of a compound represented by Compound 6

[0291]

[0292]

[0293] Compound 6 (12 g, yield 81%) was obtained in the same manner as in the preparation of Compound 5 of Synthesis Example 5, except that Chemical Formula 2B was used instead of Chemical Formula 1B.

[0294] MS:[M+H] + =613

[0295] <Synthesis Example 7> Preparation of the compound represented by Compound 7

[0296]

[0297] Compound 7 (11 g, yield 74%) was obtained in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Chemical Formula 3A was used instead of Chemical Formula 1A, and Chemical Formula 2B was used instead of Chemical Formula 1B.

[0298] MS:[M+H] + =613

[0299] <Synthesis Example 8> Preparation of the compound represented by Compound 8

[0300]

[0301]

[0302] (1) Preparation of Chemical Formula 4A

[0303] After dissolving Chemical Formula 4A-2 (13.6 g, 38.6 mmol) in tetrahydrofuran and cooling the resultant to -78°C under nitrogen, n-BuLi (1.05 equivalents) was introduced therein. After 30 minutes, Chemical Formula 4A-1 (8.1 g, 38.6 mmol) was introduced thereinto, and the resultant was stirred at room temperature. The generated phenol intermediate was filtered, and an excess of H was introduced thereinto. 2 SO 4 Aqueous solution was added, and the resultant was refluxed. After the resultant was cooled to room temperature, an excess of ethanol was introduced therein, and the resultant was filtered. The filtered solid was recrystallized with chloroform and ethyl acetate to obtain Chemical Formula 4A (10 g, yield 56%).

[0304] MS:[M+H] + =467

[0305] (2) Preparation of Compound 8

[0306] Compound 8 (15 g, yield 83%) was obtained in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Chemical Formula 4A and Chemical Formula 5B were used instead of Chemical Formula 1A and Chemical Formula 1B, respectively.

[0307] MS:[M+H] + =745

[0308] <Synthesis Example 9> Preparation of the compound represented by Compound 9

[0309]

[0310]

[0311] (1) Preparation of Chemical Formula 5A

[0312] Chemical Formula 5A (10 g, yield 61%) was obtained in the same manner as in the preparation of Chemical Formula 4A in Synthesis Example 8, except that Chemical Formula 5A-1 and Chemical Formula 5A-2 were used instead of Chemical Formula 4A-1 and Chemical Formula 4A-2, respectively.

[0313] MS:[M+H] + =427

[0314] (2) Preparation of Compound 9

[0315] Compound 9 (10 g, yield 65%) was obtained in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Chemical Formula 5A was used instead of Chemical Formula 1A.

[0316] MS:[M+H] + =629

[0317] <Synthesis Example 10> Preparation of the compound represented by Compound 10

[0318]

[0319]

[0320] (1) Preparation of Compound 10

[0321] Compound 10 (10.5 g, yield 67%) was obtained in the same manner as in the preparation of Compound 9 of Synthesis Example 9, except that Chemical Formula 2B was used instead of Chemical Formula 1B.

[0322] MS:[M+H] + =629

[0323] <Synthesis Example 11> Preparation of the compound represented by Compound 11

[0324]

[0325] (1) Preparation of Compound 11

[0326] Compound 11 (12 g, yield 73%) was obtained in the same manner as in the preparation of Compound 9 of Synthesis Example 9, except that Chemical Formula 3B was used instead of Chemical Formula 1B.

[0327] MS:[M+H] + =679

[0328] <Synthesis Example 12> Preparation of the compound represented by Compound 12

[0329]

[0330]

[0331] (1) Preparation of Compound 12

[0332] Compound 12 (12 g, yield 72%) was obtained in the same manner as in the preparation of Compound 5 of Synthesis Example 5, except that Chemical Formula 5B was used instead of Chemical Formula 1B.

[0333] MS:[M+H] + =689

[0334] <Synthesis Example 13> Preparation of the compound represented by Compound 13

[0335]

[0336] (1) Preparation of Compound 13

[0337] Compound 13 (13 g, yield 78%) was obtained in the same manner as in the preparation of Compound 5 of Synthesis Example 5, except that Chemical Formula 6B was used instead of Chemical Formula 1B.

[0338] MS:[M+H] + =689

[0339] <Synthesis Example 14> Preparation of the compound represented by Compound 14

[0340]

[0341]

[0342] (1) Preparation of Compound 14

[0343] Compound 14 (11 g, yield 66%) was obtained in the same manner as in the preparation of Compound 5 of Synthesis Example 5, except that Chemical Formula 7B was used instead of Chemical Formula 1B.

[0344] MS:[M+H] + =689

[0345] <Synthesis Example 15> Preparation of the compound represented by Compound 15

[0346]

[0347] (1) Preparation of Compound 15

[0348] Compound 15 (14 g, yield 78%) was obtained in the same manner as in the preparation of Compound 5 of Synthesis Example 5, except that Chemical Formula 8B was used instead of Chemical Formula 1B.

[0349] MS:[M+H] + =739

[0350] <Synthesis Example 16> Preparation of the compound represented by Compound 16

[0351]

[0352]

[0353] Compound 16 (15 g, yield 81%) was obtained in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Chemical Formula 6A and Chemical Formula 9B were used instead of Chemical Formula 1A and Chemical Formula 1B, respectively.

[0354] MS:[M+H] + =764

[0355] <Synthesis Example 17> Preparation of the compound represented by Compound 17

[0356]

[0357]

[0358] (1) Preparation of Chemical Formula 7A

[0359] Chemical Formula 7A (15 g, yield 76%) was obtained in the same manner as in the preparation of Chemical Formula 1A of Synthesis Example 1, except that naphthol was used instead of phenol, and 2-bromo-9H-fluoren-9-one was used instead of 4-bromo-9H-fluoren-9-one.

[0360] MS:[M+H] + =511

[0361] (2) Preparation of Compound 17

[0362] Compound 17 (13 g, yield 68%) was obtained in the same manner as in the preparation of Compound 13 of Synthesis Example 13, except that Chemical Formula 7A was used instead of Chemical Formula 2A.

[0363] MS:[M+H]+ =789

[0364] <Synthesis Example 18> Preparation of the compound represented by Compound 18

[0365]

[0366]

[0367] (1) Preparation of Chemical Formula 8A

[0368] Chemical Formula 8A (13 g, yield 69%) was obtained in the same manner as in the preparation of Chemical Formula 5A of Synthesis Example 9, except that Chemical Formula 8A-1 was used instead of Chemical Formula 5A-1.

[0369] MS:[M+H] + =487

[0370] (2) Preparation of Compound 18

[0371] Compound 18 (12 g, yield 72%) was obtained in the same manner as in the preparation of Compound 9 of Synthesis Example 9, except that Chemical Formula 8A was used instead of Chemical Formula 5A.

[0372] MS:[M+H] + =689

[0373] <Synthesis Example 19> Preparation of the compound represented by Compound 19

[0374]

[0375] Compound 19 (15 g, yield 79%) was obtained in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Chemical Formula 9B was used instead of Chemical Formula 1B.

[0376] MS:[M+H] + =779

[0377] <Synthesis Example 20> Preparation of the compound represented by Compound 20

[0378]

[0379] Compound 20 (9 g, yield 54%) was obtained in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Chemical Formula 10B was used instead of Chemical Formula 1B.

[0380] MS:[M+H] + =689

[0381] <Synthesis Example 21> Preparation of the compound represented by Compound 21

[0382]

[0383] Compound 21 (10 g, yield 56%) was obtained in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Chemical Formula 11B was used instead of Chemical Formula 1B.

[0384] MS:[M+H] + =739

[0385] <Synthesis Example 22> Preparation of the compound represented by Compound 22

[0386]

[0387]

[0388] Compound 22 (11 g, yield 66%) was obtained in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Chemical Formula 13B was used instead of Chemical Formula 1B.

[0389] MS:[M+H] + =689

[0390] <Synthesis Example 23> Preparation of the compound represented by Compound 23

[0391]

[0392] Compound 23 (14 g, yield 84%) was obtained in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Chemical Formula 5B was used instead of Chemical Formula 1B.

[0393] MS:[M+H] + =689

[0394] <Synthesis Example 24> Preparation of the compound represented by Compound 24

[0395]

[0396]

[0397] Compound 24 (12 g, yield 72%) was obtained in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Chemical Formula 6B was used instead of Chemical Formula 1B.

[0398] MS:[M+H] + =689

[0399] <Synthesis Example 25> Preparation of the compound represented by Compound 25

[0400]

[0401] Compound 25 (13 g, yield 72%) was obtained in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Chemical Formula 14B was used instead of Chemical Formula 1B.

[0402] MS:[M+H] + =739

[0403] <Synthesis Example 26> Preparation of the compound represented by Compound 26

[0404]

[0405]

[0406] Compound 26 (8 g, yield 48%) was obtained in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Chemical Formula 15B was used instead of Chemical Formula 1B.

[0407] MS:[M+H] + =689

[0408] <Synthesis Example 27> Preparation of the compound represented by Compound 27

[0409]

[0410] Compound 27 (11 g, yield 66%) was obtained in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Chemical Formula 16B was used instead of Chemical Formula 1B.

[0411] MS:[M+H] + =689

[0412] <Synthesis Example 28> Preparation of the compound represented by Compound 28

[0413]

[0414]

[0415] Compound 28 (15 g, yield 83%) was obtained in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Chemical Formula 17B was used instead of Chemical Formula 1B.

[0416] MS:[M+H] + =739

[0417] <Experimental example>

[0418] Experimental Example 1: Calculation of the difference (ΔEST) between the S1 energy value and the T1 energy value

[0419] The difference between the S1 energy value and the T1 energy value of the compound corresponding to Chemical Formula 1, and the difference between the S1 energy value and the T1 energy value of the compound having the same core structure as the compound of the present disclosure but not containing a bicyclic or more ring-condensed aromatic group were calculated and shown in the following Table 1, and the difference between the S1 energy value and the T1 energy value (ΔEST, eV) is shown below each compound.

[0420] [Table 1]

[0421]

[0422]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428]

[0429] It was determined from Table 1 that the compounds (Compounds 1 to 28) containing a bicyclic or higher ring-condensed aromatic group in one or more of Ar1 and Ar2 of Chemical Formula 1 of the present application had a greater difference (ΔEST) between the S1 energy value and the T1 energy value than the compounds (Comparative Compounds 1 to Comparative Compounds 13) not containing a bicyclic or higher ring-condensed aromatic group.

[0430] Experimental Example 2: Fabrication of Device

[0431] <Example 1-1>

[0432] It is coated with a thickness of A glass substrate (corning 7059 glass) with indium tin oxide (ITO) as a thin film was placed in distilled water dissolved with a dispersant and ultrasonically cleaned. A product of Fischer Co. was used as a cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as distilled water. After the ITO was cleaned for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After the cleaning with distilled water was completed, the substrate was ultrasonically cleaned with isopropyl alcohol, acetone and methanol solvents in this order, and then dried.

[0433] On the transparent ITO electrode prepared as above, hexanitrile hexaazatriphenylene (HAT) was thermally vacuum deposited onto The hole injection layer is formed by vacuum depositing a hole transporting material HT1 on the hole injection layer. , and vacuum deposit the host BH1 and dopant BD1 compounds onto The thickness of the light-emitting layer is as follows. When the hole blocking layer (electron control layer) is deposited on the light-emitting layer using the ET-A compound, After that, the compound 1 synthesized in Synthesis Example 1 and lithium quinoline (LiQ) were vacuum deposited onto the substrate at a weight ratio of 1:1. On the electron injection and transport layer, lithium fluoride (LiF) is deposited in a continuous sequence to form an electron injection and transport layer. and deposit aluminum to a thickness of Thus, an organic light emitting device was manufactured.

[0434] During the above process, the deposition rate of the organic material is maintained at / second to / sec, and the deposition rates of lithium fluoride and aluminum at the cathode were kept at / second and / sec, and the vacuum degree during deposition was maintained at 2 × 10 -7 Up to 5×10 -6 The support is used to manufacture organic light-emitting devices.

[0435]

[0436]

[0437]

[0438] Other Examples and Comparative Examples

[0439] Organic light-emitting devices were manufactured in the same manner as in Example 1-1, except that the compounds described in the following Table 2 were each used instead of using Compound 1 for the electron injection and transport layer in Example 1-1.

[0440] For each organic light-emitting device manufactured in the experimental example, at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm 2 The time taken for the luminance to decrease to 98% (LT98) compared to the initial luminance was measured at a current density of 1.3 Å. The results are shown in Table 2 below.

[0441] [Table 2]

[0442]

[0443]

[0444]

[0445] <Example 2-1>

[0446] It is coated with a thickness of A glass substrate (corning 7059 glass) with indium tin oxide (ITO) as a thin film was placed in distilled water dissolved with a dispersant and ultrasonically cleaned. A product of Fischer Co. was used as a cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as distilled water. After the ITO was cleaned for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After the cleaning with distilled water was completed, the substrate was ultrasonically cleaned with isopropyl alcohol, acetone and methanol solvents in this order, and then dried.

[0447] On the transparent ITO electrode prepared as above, hexanitrile hexaazatriphenylene (HAT) was thermally vacuum deposited onto The hole injection layer is formed by vacuum depositing a hole transporting material HT2 on the hole injection layer. Then, the following compound HT3 was vacuum deposited onto The main BH2 and dopant BD2 compounds are vacuum deposited onto the hole transport layer to form an electron blocking layer. On the light-emitting layer, the compound 1 prepared in Synthesis Example 1 was vacuum deposited to The thickness of the lithium fluoride (LiF) is obtained by sequentially depositing lithium fluoride (LiF) to and deposit aluminum to a thickness of Thus, an organic light emitting device was manufactured.

[0448] During the above process, the deposition rate of the organic material is maintained at / second to / sec, and the deposition rates of lithium fluoride and aluminum at the cathode were kept at / second and / sec, and the vacuum degree during deposition was maintained at 2 × 10 -7 Up to 5×10 -6 The support is used to manufacture organic light-emitting devices.

[0449]

[0450] Other Examples and Comparative Examples

[0451] Organic light-emitting devices were manufactured in the same manner as in Example 2-1, except that the compounds described in the following Table 3 were each used instead of using Compound 1 for the electron injection and transport layer in Example 2-1.

[0452] For each organic light-emitting device manufactured in the experimental example, at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm 2 The time taken for the luminance to decrease to 98% (LT98) compared to the initial luminance was measured at a current density of 1.3 Å. The results are shown in Table 3 below.

[0453] [Table 3]

[0454]

[0455]

[0456]

[0457] <Example 3-1>

[0458] It is coated with a thickness of A glass substrate (corning 7059 glass) with indium tin oxide (ITO) as a thin film was placed in distilled water dissolved with a dispersant and ultrasonically cleaned. A product of Fischer Co. was used as a cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as distilled water. After the ITO was cleaned for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After the cleaning with distilled water was completed, the substrate was ultrasonically cleaned with isopropyl alcohol, acetone and methanol solvents in this order, and then dried.

[0459] On the transparent ITO electrode prepared as above, hexanitrile hexaazatriphenylene (HAT) was thermally vacuum deposited onto The hole injection layer is formed by vacuum deposition of NPB. The first hole transport layer is formed by vacuum depositing the following compound HT3 on the first hole transport layer. The first electron blocking layer was formed by vacuum depositing the following YGH-A, YGH-B and YGD at a weight ratio of 2:2:1 onto the The first light-emitting layer is formed on the first electron blocking layer with a film thickness of . Then, compound ET-B is vacuum-deposited on the first light-emitting layer to The first electron transport layer was formed by vacuum depositing the following compound NCG and lithium (Li) at a weight ratio of 50:1 onto the An N-type charge generation layer is formed on the first electron transport layer with a thickness of .

[0460] Then, by forming HT-A to The P-type charge generation layer is formed by doping the compound PCG at a doping concentration of 30 wt %, and further vacuum depositing only HT-A to The second hole transport layer was formed by vacuum depositing a compound represented by BH3 and BD3 at a weight ratio of 96:4. The thickness is used as the second light-emitting layer.

[0461] On the light-emitting layer, the compound 12 prepared in Synthesis Example 12 was vacuum deposited onto The thickness of the lithium fluoride (LiF) and aluminum are deposited successively to The thickness and To form a cathode, a thickness of 10000 is provided. Thus, an organic light emitting device is manufactured.

[0462] During the above process, the deposition rate of the organic material is maintained at / second to / sec, and the deposition rates of lithium fluoride and aluminum at the cathode were kept at / second and / sec, and the vacuum degree during deposition was maintained at 2 × 10 -7 Up to 5×10 -6 The support is used to manufacture organic light-emitting devices.

[0463]

[0464] Other Examples and Comparative Examples

[0465] Organic light-emitting devices were manufactured in the same manner as in Example 3-1, except that the compounds described in the following Table 4 were each used instead of using Compound 12 for the electron injection and transport layer in Example 3-1.

[0466] For each organic light-emitting device manufactured in the experimental example, at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm 2 The time taken for the luminance to decrease to 98% (LT98) compared to the initial luminance was measured at a current density of 1.3 Å. The results are shown in Table 4 below.

[0467] [Table 4]

[0468]

[0469] <Example 4-1>

[0470] It is coated with a thickness of A glass substrate (corning 7059 glass) with indium tin oxide (ITO) as a thin film was placed in distilled water dissolved with a dispersant and ultrasonically cleaned. A product of Fischer Co. was used as a cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as distilled water. After the ITO was cleaned for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After the cleaning with distilled water was completed, the substrate was ultrasonically cleaned with isopropyl alcohol, acetone and methanol solvents in this order, and then dried.

[0471] On the transparent ITO electrode prepared as above, hexanitrile hexaazatriphenylene (HAT) was thermally vacuum deposited onto The hole injection layer is formed by vacuum deposition of NPB. The first hole transport layer is formed by vacuum depositing compound HT3 on the first hole transport layer. to form a first electron blocking layer.

[0472] The host BH3 and dopant BD3 compounds were vacuum deposited onto the On the light-emitting layer, the compound 24 prepared in Synthesis Example 24 was deposited to The thickness of the first electron transport layer is then vacuum deposited on the first electron transport layer with the following compound NCG and lithium (Li) at a weight ratio of 50:1. Then, HT-A is formed to a thickness of The P-type charge generation layer is formed by doping the compound PCG at a doping concentration of 30 wt %, and further vacuum depositing only HT-A to to form a second hole transport layer.

[0473] Subsequently, YGH-A, YGH-B and YGD were vacuum deposited onto the substrate at a weight ratio of 2:2:1. The second light-emitting layer is formed on the second hole transport layer with a film thickness of . Then, compound ET-B is vacuum deposited on the second light-emitting layer. Then, on the second electron transport layer, the following compound NCG and lithium (Li) were vacuum deposited at a weight ratio of 50:1. to form a second N-type charge generation layer.

[0474] Then, by forming HT-B to The P-type charge generation layer is formed by doping the compound PCG at a doping concentration of 30 wt %, and further vacuum depositing only HT-B to The third hole transport layer is formed by vacuum depositing a compound represented by BH3 and BD3 at a weight ratio of 96:4. The thickness of the third light-emitting layer is .

[0475] On the light-emitting layer, the compound 12 prepared in Synthesis Example 12 was vacuum deposited to The thickness of the lithium fluoride (LiF) and aluminum are deposited successively to The thickness and To form a cathode, a thickness of 10000 is provided. Thus, an organic light emitting device is manufactured.

[0476] During the above process, the deposition rate of the organic material is maintained at / second to / sec, and the deposition rates of lithium fluoride and aluminum at the cathode were kept at / second and / sec, and the vacuum degree during deposition was maintained at 2 × 10 -7 Up to 5×10 -6 The support is used to manufacture organic light-emitting devices.

[0477]

[0478] Another comparative example (Comparative example 4-1)

[0479] An organic light-emitting device was manufactured in the same manner as in Example 4-1, except that Comparative Compound 6 was used instead of Compound 12, and Comparative Compound 13 was used instead of Compound 24.

[0480] For each organic light-emitting device manufactured in the examples, at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm 2 The time taken for the luminance to decrease to 98% (LT98) compared to the initial luminance was measured at a current density of 1.3 Å. The results are shown in Table 5 below.

[0481] [Table 5]

[0482]

[0483] It is determined from the experimental results of Tables 2 to 5 that the embodiments containing the compounds of the present application have excellent driving voltage, current efficiency and lifespan characteristics compared to the comparative examples using compounds in which Ar1 and Ar2 of Chemical Formula 1 of the present application do not contain a bicyclic or higher ring fused aromatic group, Chemical Formula 2 of the present application is bonded to R1 to R8, or one or more of L1 to L3 contain a sub-heteroaryl group.

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] in, In Chemical Formula 1, X is O or S; and One or more of R9 to R16 are connected to * of the following Chemical Formula 2, and the rest of R9 to R16 not connected to Chemical Formula 2 and R1 to R8 are the same as or different from each other, and are each independently hydrogen, deuterium, methyl, phenyl, or bonded to an adjacent group to form a benzene ring, [Chemical formula 2] In chemical formula 2, A1 to A3 are the same as or different from each other and are each independently N or CR, and two or more of A1 to A3 are N; L1 and L2 are the same as or different from each other, and are each independently a direct bond, a phenylene group or a naphthylene group; L3 is a direct bond or a phenylene group; One or more of Ar1 and Ar2 are naphthyl or phenanthryl, and the others are the same as or different from each other and are each independently phenyl or dibenzofuranyl; R are the same or different from each other and are each independently hydrogen or deuterium; m1 to m3 are each an integer of 0 or 1.

2. The compound according to claim 1, wherein one or more of Ar1 and Ar2 is the following structure, and the others are the same or different from each other and are each independently phenyl or dibenzofuranyl: In the structure described, R21 is each independently hydrogen; n1 is an integer from 0 to 7; and * refers to the attachment site.

3. The compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 3 to 4: [Chemical formula 3] [Chemical formula 4] In Chemical Formulas 3 to 4, X, R1 to R8, A1 to A3, L1 to L3 and m1 to m3 have the same definitions as in claim 1; Ar3 is naphthyl, phenanthrenyl, phenyl, or dibenzofuranyl; R21 and R22 are each independently hydrogen; R32 is hydrogen, deuterium, methyl, or phenyl; n1 is an integer from 0 to 7, n2 is an integer from 0 to 9; and p1 is an integer of 0 to 7, and when p1 is 2 or more, two or more R32 are the same as or different from each other.

4. A compound selected from any one of the following structures:

5. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 satisfies the following Formula 1: [Formula 1] ΔEST C E >ΔEST E1 In formula 1, ΔEST C E1 is the difference between the singlet energy value and the triplet energy value of the compound represented by Chemical Formula 1; and ΔEST El is the difference between the singlet energy value and the triplet energy value of the compound in which Ar1 and Ar2 in the compound represented by Chemical Formula 1 do not include a bicyclic or more ring-condensed aromatic group.

6. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 satisfies the following Formula 2: [Formula 2] 0.30eV <AEST C El <1.5eV In formula 2, ΔEST C El is the difference between the singlet energy value and the triplet energy value of the compound represented by Chemical Formula 1.

7. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 satisfies the following Formula 3: [Formula 3] ΔESTC E1 -AEST El >0.05eV In formula 3, ΔEST C El is the difference between the singlet energy value and the triplet energy value of the compound represented by Chemical Formula 1; and ΔEST El is the difference between the singlet energy value and the triplet energy value of the compound in which Ar1 and Ar2 in the compound represented by Chemical Formula 1 do not include a bicyclic or more ring-condensed aromatic group.

8. An organic light-emitting device, comprising: a first electrode; a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the compound according to any one of claims 1 to 7.

9. An organic light-emitting device according to claim 8, wherein the organic material layer comprises a hole injection layer, a hole transport layer, or a layer that simultaneously performs hole transport and hole injection, and the hole injection layer, the hole transport layer, or the layer that simultaneously performs hole transport and hole injection contains the compound.

10. An organic light-emitting device according to claim 8, wherein the organic material layer comprises an electron transport layer, an electron injection layer, or a layer that simultaneously performs electron transport and electron injection, and the electron transport layer, the electron injection layer, or the layer that simultaneously performs electron transport and electron injection contains the compound. 11 . The organic light emitting device according to claim 8 , wherein the organic material layer comprises a light emitting layer, and the light emitting layer contains the compound.

12. An organic light-emitting device according to claim 8, wherein the organic material layer comprises one or more layers selected from the following: a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, a hole blocking layer, a layer that simultaneously performs hole transport and hole injection, and a layer that simultaneously performs electron transport and electron injection. 13 . The organic light emitting device according to claim 8 , wherein the organic material layer comprises a light emitting layer, the light emitting layer comprises a host and a dopant, and the maximum light emission wavelength of the dopant is 400 nm to 520 nm. The organic light emitting device according to claim 13 , wherein the dopant is a blue fluorescent dopant. The organic light emitting device according to claim 8 , wherein the organic material layer comprises two or more light emitting layers. 16 . The organic light emitting device according to claim 15 , wherein at least one of the two or more light emitting layers comprises a blue fluorescent dopant.

17. An organic light-emitting device according to claim 8, wherein the organic material layer includes a first stack and a second stack, and includes one or more charge generation layers between the first stack and the second stack, the first stack includes one or more light-emitting layers, and the second stack includes one or more light-emitting layers.

18. An organic light-emitting device according to claim 8, wherein the organic material layer includes a first stack, a second stack and a third stack, and one or more charge generating layers are respectively included between the first stack and the second stack, and between the second stack and the third stack, the first stack includes one or more light-emitting layers, the second stack includes one or more light-emitting layers, and the third stack includes one or more light-emitting layers.

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