Compound and organic light-emitting device comprising same

Abstract

The present specification relates to a compound and an organic light-emitting device comprising the same.

Description

Technical Field

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0043070 filed in the Korean Intellectual Property Office on March 31, 2023, 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] 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 has a multilayer structure composed of different materials in many cases to improve the efficiency and stability of the organic light-emitting device. For example, the organic material layer may be composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light-emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic material layer, and electrons are injected from the cathode into the organic material layer, and excitons are formed when the injected holes and electrons meet each other, and light is emitted when the excitons fall back to the ground state.

[0004] There is a continuing need to develop new materials for the aforementioned organic light-emitting devices. Summary of the invention

[0005] Technical issues

[0006] The present specification is directed to providing a compound and an organic light-emitting device including the same.

[0007] Technical Solution

[0008] This specification provides a compound of the following Chemical Formula 1.

[0009] [Chemical formula 1]

[0010]

[0011] In Chemical Formula 1,

[0012] X1 is O or S,

[0013] L1 is a single bond; substituted or unsubstituted phenylene; substituted or unsubstituted biphenylene; substituted or unsubstituted terphenylene; substituted or unsubstituted quaterphenylene; substituted or unsubstituted fluorenylene; substituted or unsubstituted spirocyclopentanefluorenylene; substituted or unsubstituted spirobifluorenylene; substituted or unsubstituted naphthylene; substituted or unsubstituted phenanthrenylene; substituted or unsubstituted trimphenylene; substituted or unsubstituted substituted or unsubstituted phenanthrofuranyl; substituted or unsubstituted phenanthrothienyl; substituted or unsubstituted benzofuranyl; substituted or unsubstituted benzothiophenylene; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted dibenzothiophenylene; substituted or unsubstituted benzonaphthofuranyl; substituted or unsubstituted benzonaphthothiophenylene; substituted or unsubstituted carbazolylene; or substituted or unsubstituted benzocarbazolylene,

[0014] Any one of R1 to R8 is bonded to L1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; aryl which is unsubstituted or substituted with deuterium, alkyl, cycloalkyl or heterocyclic group having O or S; or substituted or unsubstituted heterocyclic group having O or S, and is optionally fused with an adjacent group to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted heterocyclic ring,

[0015] Ar1 is a pyrenyl group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group and a heteroaryl group; a fluoranthenyl group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group and a heteroaryl group; or a phenanthrenyl group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group and a heteroaryl group,

[0016] m is an integer from 0 to 3, and when m is 2 or more, L1 in the brackets are the same as or different from each other,

[0017] x is 1 or 2, and when x is 2, the structures in the brackets are the same as or different from each other, and

[0018] y is an integer of 1 or 2, and when y is 2, Ar1 in the brackets are the same as or different from each other.

[0019] In addition, the present specification provides an organic light-emitting device including: an anode; a cathode; and an organic material layer having one or more layers disposed between the anode and the cathode, wherein one or more layers of the organic material layer include the above-mentioned compound.

[0020] Beneficial Effects

[0021] An organic light emitting device using the compound according to an exemplary embodiment of the present application may have low driving voltage, high light emitting efficiency, or a long lifetime. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] Figure 1 The structure of an organic light emitting device according to a first exemplary embodiment is shown.

[0023] Figure 2 The structure of an organic light emitting device according to a second exemplary embodiment is shown.

[0024] Figure 3 The structure of an organic light emitting device according to a third exemplary embodiment is shown.

[0025] Figure 4 The structure of an organic light emitting device according to a fourth exemplary embodiment is shown.

[0026] Figure 5 : is a graph showing the results of HPLC analysis of a film deposited using the mixture of Experimental Example 2.

[0027] Figure 6 Graphs showing the results of HPLC analysis of a film deposited using the mixture of Experimental Example 3.

[0028] <Description of Reference Numerals>

[0029] 101: Base

[0030] 102: Anode

[0031] 103: Hole injection layer

[0032] 104: Hole transport layer

[0033] 105: Hole regulation layer

[0034] 106: Luminous layer

[0035] 106-1: First light-emitting layer

[0036] 106-2: Second light-emitting layer

[0037] 107: Electronic Regulation Layer

[0038] 108: Electron transport layer

[0039] 109: Electron injection layer

[0040] 110: cathode DETAILED DESCRIPTION

[0041] Hereinafter, the present specification will be described in detail.

[0042] The present specification provides a compound represented by Chemical Formula 1.

[0043] Chemical formula 1 according to an exemplary embodiment of the present specification is a structure in which a specific functional group Ar1 is bonded to a phenanthrofuran or phenanthrothiophene structure through an intermediate connecting group L1, and has excellent ability to transfer electrons and holes and high quantum efficiency. Therefore, by applying the compound of chemical formula 1 to the organic material layer of an organic light-emitting device, the effects of reducing driving voltage, improving efficiency, and extending service life can be obtained.

[0044] In the present specification, when a part “includes / comprises” a constituent element, unless otherwise specifically described, this does not mean to exclude another constituent element but means that another constituent element may be further included / comprised.

[0045] In this specification, when one member is disposed “on” another member, this includes not only a case where one member is in contact with the other member but also a case where another member is present between the two members.

[0046] In the present specification, * or a dotted line means a site to which another substituent or a bonding moiety is bonded or condensed.

[0047] In the present specification, Cn means that the number of carbon atoms is n, and Cn to Cm means that the number of carbon atoms is n to m.

[0048] Examples of the substituent in the present specification will be described below, but are not limited thereto.

[0049] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of the substitution is not limited as long as the position is a position where the hydrogen atom is substituted (i.e., a position where a substituent can be substituted), and when two or more substitutions are made, the two or more substituents may be the same or different from each other.

[0050] In the present specification, the term "substituted or unsubstituted" means substituted with one or two or more substituents selected from the following: deuterium; halogen group; cyano group (-CN); silyl group; boron group; alkyl group; cycloalkyl group; aryl group; and heterocyclic group, substituted with a substituent in which two or more substituents are connected among the exemplified substituents, or having no substituent. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may also be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

[0051] In an exemplary embodiment of the present invention, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a cyano group (-CN); a silyl group; a C1 to C20 alkyl group; a C3 to C60 cycloalkyl group; a C6 to C60 aryl group; and a C2 to C60 heterocyclic group, substituted with a substituent in which two or more groups selected from the above group are connected, or having no substituent.

[0052] In an exemplary embodiment of the present invention, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a cyano group (-CN); a silyl group; a C1 to C20 alkyl group; a C3 to C60 cycloalkyl group; a C6 to C60 aryl group; and a C2 to C60 heterocyclic group, substituted with a substituent in which two or more groups selected from the above group are connected, or having no substituent.

[0053] In an exemplary embodiment of the present invention, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a cyano group (-CN); a silyl group; a C1 to C10 alkyl group; a C3 to C30 cycloalkyl group; a C6 to C30 aryl group; and a C2 to C30 heterocyclic group, substituted with a substituent in which two or more groups selected from the above group are connected, or having no substituent.

[0054] In an exemplary embodiment of the present invention, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a cyano group (-CN); a silyl group; a C1 to C6 alkyl group; a C3 to C20 cycloalkyl group; a C6 to C20 aryl group; and a C2 to C20 heterocyclic group, substituted with a substituent in which two or more groups selected from the above group are connected, or having no substituent.

[0055] In the present specification, the fact that two or more substituents are linked means that the hydrogen of any substituent is replaced by another substituent. For example, isopropyl and phenyl can be linked to each other to form a substituent.

[0056] In the present specification, the fact that three substituents are connected to each other includes not only the case where (substituent 1)-(substituent 2)-(substituent 3) are connected to each other in sequence, but also the case where (substituent 2) and (substituent 3) are connected to (substituent 1). For example, two phenyl groups and an isopropyl group may be connected to each other to form a substituent. The same applies to the case where four or more substituents are bonded to one another.

[0057] In the present specification, "substituted by A or B" includes not only the case where it is substituted by A alone or by B alone, but also the case where it is substituted by both A and B.

[0058] In the present specification, "substituted with at least one selected from A, B and C" means substituted with one or more substituents selected from this group, or substituted with substituents in which two or more groups selected from this group are linked.

[0059] Examples of the substituent will be described below; however, the substituent is not limited thereto.

[0060] In the present specification, examples of the halogen group include fluorine (—F), chlorine (—Cl), bromine (—Br) or iodine (—I).

[0061] In this specification, a silyl group can be represented by the chemical formula -SiY a Y b Y c indicates that, and Y a , Y b and Y c Each of them may be hydrogen; a substituted or unsubstituted alkyl; or a substituted or unsubstituted aryl. Specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited thereto.

[0062] In this specification, the boron group can be represented by the chemical formula -BY d Y e indicates that, and Y d and Y e Each of them may be hydrogen; a substituted or unsubstituted alkyl; or a substituted or unsubstituted aryl. Specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, etc., but are not limited thereto.

[0063] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to yet another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, etc., but are not limited thereto.

[0064] Substituents including alkyl groups and other alkyl moieties described in the present specification include both straight-chain and branched forms.

[0065] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another embodiment, the number of carbon atoms 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.

[0066] 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 an exemplary embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to an exemplary embodiment, the number of carbon atoms of the aryl group is 6 to 20. Examples of monocyclic aryl groups as aryl groups include phenyl, biphenyl, terphenyl, etc., but are not limited thereto. Examples of polycyclic aryl groups include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, triphenylene, etc., but not limited thereto.

[0067] In this specification, aryl can also include a form in which an aliphatic ring is fused with an aromatic ring. For example, aryl includes fluorenyl, spirofluorenyl, spirobifluorenyl, tetrahydronaphthyl, dihydroindenyl, dihydroanthracenyl, etc. In the following structure, one of the carbons of the benzene ring can be connected to another position.

[0068]

[0069] In the present specification, the 9th carbon atom (C) of the fluorenyl group may be substituted with an alkyl group, an aryl group, or the like, and two substituents may be bonded to each other to form a spiro structure such as cyclopentane or fluorene.

[0070] In the present specification, the above description about the aryl group can be applied to the arylene group, except that the arylene group is divalent.

[0071] In the present specification, the alkylaryl group means an aryl group substituted with an alkyl group, and a substituent other than the alkyl group may be further bonded.

[0072] In the present specification, an arylalkyl group means an alkyl group substituted with an aryl group, and a substituent other than the alkyl group may be further bonded.

[0073] In this specification, aryloxy is a group in which an aryl group is connected to an oxygen atom, and arylthio is a group in which an aryl group is connected to a sulfur atom, and the above description of aryl can be applied to the aryl of aryloxy and arylthio. The aryl of aryloxy is the same as the above-mentioned example of aryl. Specifically, examples of aryloxy include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthraceneoxy, 2-anthraceneoxy, 9-anthraceneoxy, 1-phenanthrenoxy, 3-phenanthrenoxy, 9-phenanthrenoxy, and examples of arylthio include phenylthio, 2-methylphenylthio, 4-tert-butylphenylthio, etc., but examples are not limited thereto.

[0074] In the present specification, the heterocyclic group is a cyclic group containing one or more of N, O, P, S, Si and Se as a heteroatom, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 60. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. Examples of the heterocyclic group include pyridyl; quinolyl; thienyl; dibenzothienyl; furyl; dibenzofuranyl; naphthobenzofuranyl; carbazolyl; benzocarbazolyl; naphthobenzothienyl; dibenzothirolyl; naphthobenzothirolyl; hexahydrocarbazolyl; dihydroacridinyl; dihydrodibenzoaziridinyl; phenanthroline; oxazine; phenothiazine; dihydrodibenzodiazepine; spiro(dibenzosilole-dibenzodiazepine) group; spiro(acridine-fluorene) group; and the like, but are not limited thereto.

[0075]

[0076] In the present specification, the above description about the heterocyclic group can be applied to the heteroaryl group, except that the heteroaryl group is aromatic.

[0077] In the present specification, the amine group can be selected from -NH2; alkylamine group; N-alkylarylamine group; arylamine group; N-arylheteroarylamine group; N-alkylheteroarylamine group; and heteroarylamine group, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl-anthrylamine, diphenylamine, N-phenylnaphthylamine, xylylamine, N-phenyltolylamine, triphenylamine, N-phenylbiphenylamine, N-phenylnaphthylamine, N-biphenylnaphthylamine, N-naphthylfluorenylamine, N-phenylphenanthrenylamine, N-biphenylphenanthrenylamine, N-phenylfluorenylamine, N-phenylterphenylamine, N-phenanthrenylfluorenylamine, N-biphenylfluorenylamine and the like, but are not limited thereto.

[0078] In the present specification, the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.

[0079] In the present specification, the N-arylheteroarylamine group means an amine group in which N of the amine group is substituted with an aryl group and a heteroaryl group.

[0080] In the present specification, the N-alkylheteroarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and a heteroaryl group.

[0081] In the present specification, the alkyl group, aryl group and heteroaryl group in the alkylamine group, N-alkylarylamine group, arylamine group, N-arylheteroarylamine group, N-alkylheteroarylamine group and heteroarylamine group are each the same as the above-mentioned examples of the alkyl group, aryl group and heteroaryl group.

[0082] In this specification, "adjacent" groups may mean substituents that replace atoms directly connected to the atoms replaced by the corresponding substituents, substituents that are closest to the corresponding substituents in space, or other substituents that replace atoms replaced by the corresponding substituents. For example, two substituents that replace the ortho position in a benzene ring and two substituents that replace the same carbon in an aliphatic ring may be interpreted as groups "adjacent" to each other. In addition, substituents (a total of four) that are connected to two consecutive carbons in an aliphatic ring may be interpreted as "adjacent" groups.

[0083] In the present specification, “adjacent groups bond to each other to form a ring” in a substituent means that the substituent bonds to the adjacent group to form a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring.

[0084] In the present specification, "a five-membered ring or a six-membered ring formed by bonding adjacent groups" means that the ring including the substituents participating in the ring formation is five-membered or six-membered. Another ring condensed with the ring including the substituents participating in the ring formation may be included.

[0085] In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a combination thereof.

[0086] In the present specification, the heterocycle is a ring containing a heteroatom, and may be in a form in which an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring is condensed with a ring having a heteroatom. The heterocycle may be an aromatic heterocycle, an aliphatic heterocycle, or a combination thereof.

[0087] In the present specification, the aromatic hydrocarbon ring means a hydrocarbon ring in which π electrons are completely conjugated and planar, and the description about the aryl group can be applied to the aromatic hydrocarbon ring, except that the aromatic hydrocarbon ring is divalent.

[0088] In this specification, an aliphatic hydrocarbon ring has a cyclic bonding structure and means a non-aromatic ring. Examples of the aliphatic hydrocarbon ring include a cycloalkyl group or a cycloolefin group, and the above description about the cycloalkyl group or the cycloalkenyl group can be applied to the aliphatic hydrocarbon ring, except that the aliphatic hydrocarbon ring is divalent. In addition, the substituted aliphatic hydrocarbon ring also includes an aliphatic hydrocarbon ring in which an aromatic ring is condensed.

[0089] In the present specification, the condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring means that the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring form a condensed ring. Examples of the condensed ring of an aromatic ring and an aliphatic ring include 1,2,3,4-tetrahydronaphthyl, 2,3-dihydro-1H-indenyl, etc., but are not limited thereto.

[0090] In the present specification, when adjacent groups in a substituent are bonded to each other to form a ring, any of the following structures may be formed.

[0091]

[0092] In the structure described,

[0093] A1 to A14 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0094] a1 to a9 are each an integer from 1 to 4,

[0095] a10 and a14 are each an integer from 1 to 6,

[0096] When a1 to a14 are each 2 or more, two or more substituents in brackets are the same as or different from each other, and

[0097] * indicates the position of substitution.

[0098] According to an exemplary embodiment of the present specification, A1 is hydrogen; or a substituted or unsubstituted aryl group.

[0099] According to an exemplary embodiment of the present specification, A1 is hydrogen; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0100] According to an exemplary embodiment of the present specification, A1 is hydrogen; or a substituted or unsubstituted phenyl group.

[0101] According to an exemplary embodiment of the present specification, A1 is hydrogen or a phenyl group.

[0102] According to an exemplary embodiment of the present specification, A2 to A10 and A14 are hydrogen.

[0103] According to an exemplary embodiment of the present specification, A11 to A13 are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[0104] According to an exemplary embodiment of the present specification, A11 to A13 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0105] According to an exemplary embodiment of the present specification, A11 and A12 are methyl groups.

[0106] According to an exemplary embodiment of the present specification, A13 is substituted or unsubstituted benzene, or substituted or unsubstituted naphthalene.

[0107] In the present specification, a compound of the following Chemical Formula 1 is provided.

[0108] [Chemical formula 1]

[0109]

[0110] In Chemical Formula 1,

[0111] X1 is O or S,

[0112] L1 is a single bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

[0113] Any one of R1 to R8 is bonded to L1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclyl, and optionally condensed with an adjacent group to form a substituted or unsubstituted ring,

[0114] Ar1 is a substituted or unsubstituted pyrenyl group; a substituted or unsubstituted fluoranthenyl group; or a substituted or unsubstituted phenanthryl group,

[0115] m is an integer from 0 to 3, and when m is 2 or more, L1 in the brackets are the same as or different from each other,

[0116] x is 1 or 2, and when x is 2, the structures in the brackets are the same as or different from each other, and

[0117] y is an integer of 1 or 2, and when y is 2, Ar1 in the brackets are the same as or different from each other.

[0118] In this specification, x is 1 and y is 1.

[0119] In this specification, x is 1 and y is 2.

[0120] In this specification, x is 2 and y is 1.

[0121] In this specification, x is 2 and y is 2.

[0122] In the present specification, Chemical Formula 1 is any one of the following Chemical Formulas 1-A to 1-F.

[0123] [Chemical Formula 1-A]

[0124]

[0125] [Chemical Formula 1-B]

[0126]

[0127] [Chemical Formula 1-C]

[0128]

[0129] [Chemical formula 1-D]

[0130]

[0131] [Chemical Formula 1-E]

[0132]

[0133] [Chemical Formula 1-F]

[0134]

[0135] In Chemical Formulae 1-A to 1-F, X1, L1, m, R1 to R8, and Ar1 are the same as defined in Chemical Formula 1.

[0136] In the present specification, Chemical Formula 1 is any one of the following Chemical Formulas 1-a to 1-e.

[0137] [Chemical formula 1-a]

[0138]

[0139] [Chemical formula 1-b]

[0140]

[0141] [Chemical formula 1-c]

[0142]

[0143] [Chemical formula 1-d]

[0144]

[0145] [Chemical formula 1-e]

[0146]

[0147] In Chemical Formulae 1-a to 1-e, X1 and Ar1 are the same as defined in Chemical Formula 1, and

[0148] Any one of R1 to R8 is bonded to Ar1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; aryl which is unsubstituted or substituted with deuterium, alkyl, cycloalkyl or a heterocyclic group having O or S; or a substituted or unsubstituted heterocyclic group having O or S, and is optionally fused with an adjacent group to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted heterocyclic ring.

[0149] In the present specification, Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-3.

[0150] [Chemical formula 1-1]

[0151]

[0152] [Chemical formula 1-2]

[0153]

[0154] [Chemical formula 1-3]

[0155]

[0156] In Chemical Formula 1-1 to Chemical Formula 1-3,

[0157] R1 to R8, X1, L1, x, m and y are the same as those defined in claim 1, and

[0158] Any one of R101 to R110 is bonded to L1, and the rest are the same as or different from each other and are each independently hydrogen, deuterium, an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group, or the rest are fused with an adjacent group to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted heterocycle.

[0159] In this specification, Chemical Formula 1 is the following Chemical Formula 1-4.

[0160] [Chemical formula 1-4]

[0161]

[0162] In Chemical Formulae 1-4, X1, L1, Ar1, x and y are the same as those defined in Chemical Formula 1, and L2 and L3 are each the same as those defined in L1.

[0163] Any one of R1 to R8 is bonded to any one of L1 to L3, and the rest are the same as or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, and are optionally fused with an adjacent group to form a substituted or unsubstituted ring, and

[0164] Ar1 bonds to any one of L1 to L3.

[0165] In this specification, Chemical Formula 1 is any one of the following Chemical Formulas 1-4-1 to 1-4-3.

[0166] [Chemical formula 1-4-1]

[0167]

[0168] [Chemical formula 1-4-2]

[0169]

[0170] [Chemical formula 1-4-3]

[0171]

[0172] In Chemical Formulae 1-4-1 to 1-4-3, X1, L1 and Ar1 are the same as those defined in Chemical Formula 1.

[0173] L2 and L2 are each the same as L1 in definition,

[0174] Any one of R1 to R8 is bonded to any one of L1 to L3, and the rest are the same as or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, and are optionally fused with an adjacent group to form a substituted or unsubstituted ring, and

[0175] Ar1 bonds to any one of L1 to L3.

[0176] In the present specification, L1 is a single bond; substituted or unsubstituted phenylene; substituted or unsubstituted biphenylene; substituted or unsubstituted terphenylene; substituted or unsubstituted quaterphenylene; substituted or unsubstituted fluorenylene; substituted or unsubstituted spirocyclopentanefluorenylene; substituted or unsubstituted spirobifluorenylene; substituted or unsubstituted naphthylene; substituted or unsubstituted phenanthrenylene; substituted or unsubstituted triphenylene; substituted or unsubstituted tertphenylene; substituted or unsubstituted quaterphenylene; substituted or unsubstituted fluorenylene; substituted or unsubstituted spirocyclopentanefluorenylene; substituted or unsubstituted spirobifluorenylene; substituted or unsubstituted naphthylene; substituted or unsubstituted phenanthrenylene; substituted or unsubstituted triphenylene; substituted or unsubstituted quater ... substituted phenanthrofuranyl; substituted or unsubstituted phenanthrothienyl; substituted or unsubstituted benzofuranyl; substituted or unsubstituted benzothiophenylene; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted dibenzothiophenylene; substituted or unsubstituted benzonaphthofuranyl; substituted or unsubstituted benzonaphthothiophenylene; substituted or unsubstituted carbazolylene; or substituted or unsubstituted benzocarbazolylene.

[0177] In the present specification, L1 is a single bond; a phenylene group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a biphenylene group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a terphenylene group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a quaterphenylene group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a quaterphenylene group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; fluorenyl; spirocyclopentanefluorenyl unsubstituted or substituted with at least one selected from deuterium, alkyl, cycloalkyl, aryl and heteroaryl; spirobifluorenyl unsubstituted or substituted with at least one selected from deuterium, alkyl, cycloalkyl, aryl and heteroaryl; naphthylene unsubstituted or substituted with at least one selected from deuterium, alkyl, cycloalkyl, aryl and heteroaryl; phenanthrenyl unsubstituted or substituted with at least one selected from deuterium, alkyl, cycloalkyl, aryl and heteroaryl; triphenylene unsubstituted or substituted with at least one selected from deuterium, alkyl, cycloalkyl, aryl and heteroaryl; a phenanthrofuranyl group substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a phenanthrothienyl group unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a benzofuranyl group unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a benzothienyl group unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a dibenzofuranyl group unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; an unsubstituted or a dibenzothienylene group substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a benzonaphthofuranyl group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a benzonaphthothienyl group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a carbazolylene group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; or a benzocarbazolylene group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group.

[0178] In the present specification, any one of R1 to R8 is bonded to L1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; aryl which is unsubstituted or substituted with deuterium, alkyl, cycloalkyl or a heterocyclic group having O or S; or a substituted or unsubstituted heterocyclic group having O or S, and is optionally fused with an adjacent group to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted heterocyclic ring.

[0179] In the present specification, Ar1 is a pyrenyl group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group and a heteroaryl group; a fluoranthenyl group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group and a heteroaryl group; or a phenanthrenyl group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group and a heteroaryl group.

[0180] In the present specification, at least one of R1 and R2, R2 and R3, and R4 and R5 may be bonded to form a substituted or unsubstituted hydrocarbon ring.

[0181] In the present specification, at least one of R1 and R2, R2 and R3, and R4 and R5 may be bonded to form a substituted or unsubstituted benzene ring.

[0182] In the present specification, at least one of R1 and R2, R2 and R3, and R4 and R5 may be bonded to form an unsubstituted or deuterium-substituted benzene ring.

[0183] In an exemplary embodiment of the present specification, the band gap energy of the compound can be 2.9eV or more, and 2.9eV or more and 4.0eV or less. The organic compound used in the organic light-emitting device can be used as an organic semiconductor only when the organic compound needs to have a band gap of 0.5eV to 4.0eV, and in order to display blue, the organic compound needs to have a band gap energy of at least 2.9eV. According to the principle of fluorescent blue light emission in the host-dopant system, when the band gap of the blue fluorescent host is greater than the band gap of the blue fluorescent dopant, energy transfer occurs smoothly. Therefore, in order to use the compound as a blue fluorescent host, the energy band gap of the preferred compound is 2.9eV to 4.0eV.

[0184] Various methods are known to determine the band gap energy, and in particular, cyclic voltammetry and absorption spectroscopy are representative.

[0185] Cyclic voltammetry is an electrochemical technique for measuring a band gap through oxidation and reduction reactions of a compound, and this technique measures current under conditions of cyclic voltage change, and measures current caused by oxidation-reduction reactions occurring according to changes in potential energy.

[0186] The absorption spectroscopy measures a UV-vis spectrum and is exemplified in Korean Patent Publication No. 2009-0051787 (KR 2009-0051787 A).

[0187] In the present specification, “containing deuterium”, “deuterated” or “deuterated” means that hydrogen at a substitutable position of the compound is substituted with deuterium.

[0188] In the present specification, “overdeuterated” means a compound or group in which all hydrogens in a molecule are replaced by deuterium, and has the same meaning as “100% deuterated”.

[0189] In the present specification, "X% deuterated", "X% deuteration degree" or "X% deuterium substitution rate" means that X% of hydrogens at substitutable positions in the corresponding structure are replaced by deuterium. For example, when the corresponding structure is dibenzofuran, "25% deuterated" of dibenzofuran, "25% deuteration degree" of dibenzofuran, or "25% deuterium substitution rate" of dibenzofuran means that 2 of 8 hydrogens at substitutable positions of dibenzofuran are replaced by deuterium.

[0190] In an exemplary embodiment of the present specification, the deuterium substitution rate of the compound can be 1% to 100%, specifically, 40% to 99%. The deuterium substitution rate of the compound can be 5% or more, 10% or more, 20% or more, 30% or more, 40% or more, 50% or more, 60% or more, 70% or more, or 80% or more, and 100% or less, or 99% or less. The physicochemical properties associated with deuterium, such as chemical bond length, seem to be different from those of hydrogen. In particular, it can be shown that the stretching amplitude of the CD bond is less than the stretching amplitude of the CH bond, and the van der Waals radius of deuterium is less than the van der Waals radius of hydrogen, and the CD bond is generally shorter and stronger than the CH bond. When substituted by deuterium, the energy of the ground state becomes lower, and the bond length between deuterium and carbon becomes shorter, so that the molecular hard core volume is reduced. Therefore, the electric susceptibility can be reduced, and the intermolecular interaction can be weakened, so that the volume of the film can be increased.

[0191] These characteristics may have the effect of reducing the crystallinity of the film, ie, producing an amorphous state, and may generally be effective in improving the lifetime and driving characteristics of the OLED, and may further improve heat resistance.

[0192] As prior arts related to organic light-emitting compounds containing deuterium, Korean Patent No. 10-1111406 describes a technology for providing a device with low voltage driving and long service life by substituting an amine-based compound containing carbazole with deuterium or mixing the deuterium-substituted compounds, and Korean Patent No. 10-1068224 describes a technology for using an anthracene derivative containing a phenyl group in which hydrogen in the phenyl group is replaced by deuterium as a host.

[0193] Here, the deuterium substitution rate can be calculated using a spectrum obtained by a mass spectrum of a material separated by chromatography. Specifically, the deuterium substitution rate can be calculated based on the maximum value of the molecular weight distribution in a spectrum obtained by a mass spectrum of a material separated by liquid chromatography or gas chromatography according to the sample to be measured. For example, when analyzing the degree of deuteration of the following compound A, in the MS graph, the molecular weight of the following starting material is set to 506, and the maximum molecular weight (median) of the following compound A is set to 527, and then it can be calculated that about 81% of the hydrogen has been deuterated, because 21 of the 26 hydrogens at the substitutable positions in the following starting material have been replaced by deuterium.

[0194]

[0195] In this specification, D means deuterium.

[0196] Another method for determining the deuterium substitution rate can use nuclear magnetic resonance (NMR), specifically by adding dimethylformamide (DMF) as an internal standard and using 1 The deuterium substitution rate can be calculated from the integral ratio of the total peak in the H NMR spectrum.

[0197] In an exemplary embodiment of the present specification, the compound of Chemical Formula 1 may be any one of the following structures.

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246] In the structures described, hydrogen may be replaced by deuterium.

[0247] In addition, the present specification provides an organic light-emitting device including the above compound.

[0248] In an exemplary embodiment of the present specification, an organic light emitting device is provided, which includes: an anode; a cathode; and an organic material layer having one or more layers disposed between the anode and the cathode, wherein one or more layers of the organic material layer include the compound.

[0249] The organic material layer of the organic light-emitting device of the present specification may have a single-layer structure, but may also have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0250] In an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.

[0251] In an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound. Specifically, the light-emitting layer may include a dopant and a host including the compound.

[0252] In an exemplary embodiment of the present specification, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.

[0253] In an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and further includes one or two or more layers selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

[0254] In an exemplary embodiment of the present specification, an organic light-emitting device includes: an anode; a cathode; and an organic material layer having one or more layers disposed between the anode and the cathode, the organic material layer including: a light-emitting layer; a hole transport region disposed between the light-emitting layer and the anode; and an electron transport region disposed between the light-emitting layer and the cathode, and the light-emitting layer contains the compound.

[0255] In an exemplary embodiment of the present specification, as the organic material layer in the hole transport region, one or more may be selected from a hole transport layer, a hole injection layer, a layer that simultaneously transports and injects holes, and an electron blocking layer.

[0256] In an exemplary embodiment of the present specification, as the organic material layer in the electron transport region, one or more may be selected from an electron transport layer, an electron injection layer, a layer that simultaneously transports and injects electrons, and a hole blocking layer.

[0257] In another exemplary embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, an organic material layer having one or more layers, and a cathode are sequentially stacked on a substrate.

[0258] In yet another exemplary embodiment, the organic light emitting device may be an inverted organic light emitting device in which a cathode, an organic material layer having one or more layers, and an anode are sequentially stacked on a substrate.

[0259] The organic light emitting device may have a stack structure, for example, as described below, but the stack structure is not limited thereto.

[0260] (1) Anode / hole transport layer / light-emitting layer / cathode

[0261] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0262] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0263] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0264] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0265] (6) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0266] (7) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0267] (8) Anode / hole injection layer / hole transport layer / hole regulation layer / light-emitting layer / electron transport layer / cathode

[0268] (9) Anode / hole injection layer / hole transport layer / hole regulation layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0269] (10) Anode / hole injection layer / hole transport layer / light-emitting layer / electron regulation layer / electron transport layer / electron injection layer / cathode

[0270] (11) Anode / hole injection layer / hole transport layer / hole regulation layer / light-emitting layer / electron regulation layer / electron transport layer / electron injection layer / cathode

[0271] (12) Anode / hole transport layer / first light-emitting layer / second light-emitting layer / cathode

[0272] (13) Anode / hole transport layer / first light-emitting layer / second light-emitting layer / electron transport layer / electron injection layer / cathode

[0273] (14) Anode / hole injection layer / hole transport layer / first light-emitting layer / second light-emitting layer / electron transport layer / cathode

[0274] (15) Anode / hole injection layer / hole transport layer / first light-emitting layer / second light-emitting layer / electron transport layer / electron injection layer / cathode

[0275] (16) Anode / hole injection layer / hole transport layer / hole regulation layer / first light emitting layer / second light emitting layer / electron transport layer / cathode

[0276] (17) Anode / hole injection layer / hole transport layer / hole regulation layer / first light emitting layer / second light emitting layer / electron transport layer / electron injection layer / cathode

[0277] (18) Anode / hole injection layer / hole transport layer / first light-emitting layer / second light-emitting layer / electron regulation layer / electron transport layer / electron injection layer / cathode

[0278] (19) Anode / hole injection layer / hole transport layer / hole regulation layer / first light-emitting layer / second light-emitting layer / electron regulation layer / electron transport layer / electron injection layer / cathode

[0279] The structure of the organic light-emitting device of the present specification may have the following Figures 1 to 4 The structure shown is, but not limited to, this.

[0280] Figure 1 An example of an organic light-emitting device according to an exemplary embodiment of the present invention is shown, and a structure of an organic light-emitting device in which a substrate 101, an anode 102, a light-emitting layer 106, and a cathode 110 are sequentially stacked is illustrated. In the structure described above, the compound of Chemical Formula 1 and the second compound which is an anthracene derivative may be each contained in a single light-emitting layer as a mixture or a composition, or may be contained in a light-emitting layer having two layers.

[0281] Figure 2 An example of an organic light-emitting device according to an exemplary embodiment of the present invention is shown, and a structure of an organic light-emitting device is illustrated in which a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, a light-emitting layer 106, an electron transport layer 108, an electron injection layer 109, and a cathode 110 are sequentially stacked. In the structure described above, the compound of Chemical Formula 1 and the second compound that is an anthracene derivative may each be included in a single light-emitting layer 105, or may be included in a light-emitting layer 105 having two layers.

[0282] Figure 3 An example of an organic light-emitting device according to an exemplary embodiment of the present invention is shown, and a structure of an organic light-emitting device is illustrated in which a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, a hole regulation layer 105, a light-emitting layer 106, an electron regulation layer 107, an electron transport layer 108, an electron injection layer 109, and a cathode 110 are sequentially stacked. In the structure described above, the compound of Chemical Formula 1 and the second compound that is an anthracene derivative may each be included in a single light-emitting layer, or may be included in a light-emitting layer having two or more layers.

[0283] Figure 4 An example of an organic light-emitting device according to an exemplary embodiment of the present invention is shown, and the structure of an organic light-emitting device in which a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, a hole adjustment layer 105, a first light-emitting layer 106-1, a second light-emitting layer 106-2, an electron adjustment layer 107, an electron transport layer 108, an electron injection layer 109, and a cathode 110 are sequentially stacked is illustrated. In the above structure, the compound of Chemical Formula 1 may be included in the first light-emitting layer 106-1. Alternatively, the second compound which is an anthracene derivative may be included in the second light-emitting layer 106-2, or vice versa.

[0284] The organic light-emitting device of the present specification can be manufactured by using materials and methods known in the art, except that one or more layers in the organic material layer contain the compound of the present specification, ie, the compound.

[0285] When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0286] The organic light-emitting device of the present specification can be manufactured by using materials and methods known in the art, except that one or more layers of the organic material layers contain the compound, ie, the compound of Chemical Formula 1.

[0287] For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. In this case, the organic light-emitting device can be manufactured by depositing a metal, or a conductive metal oxide, or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation to form an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer on the anode, and then depositing a material that can be used as a cathode on the organic material layer. In addition to the above method, the organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0288] In addition, when manufacturing an organic light-emitting device, the compound of Chemical Formula 1 can be formed into an organic material layer not only by a vacuum deposition method but also by a solution application method. Here, the solution application method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited thereto.

[0289] The anode is an electrode for injecting holes, and as an anode material, a material with a high work function is generally preferred to promote hole injection into the organic material layer. Specific examples of anode materials that can be used in the present invention 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 SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline; etc., but are not limited thereto.

[0290] The cathode is an electrode for injecting electrons, and as a cathode material, a material having a low work function is generally preferred to facilitate electron injection 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 LiO2 / Al; etc., but are not limited thereto.

[0291] The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably such a compound: it has the ability to transport holes, so it has the effect of injecting holes at the anode and has an excellent effect of injecting holes into the light-emitting layer or the light-emitting material, preventing the excitons generated by the light-emitting layer from moving to the electron injection layer or the electron injection material, and is also excellent in the ability to form a thin film. The highest occupied molecular orbital (HOMO) of the hole injection material is preferably a value 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 perylene, anthraquinone, conductive polymers based on polyaniline and polythiophene, etc., but are not limited thereto.

[0292] According to an exemplary embodiment of the present specification, the hole injection layer includes a compound of the following Chemical Formula HI-1, but is not limited thereto.

[0293] [Chemical formula HI-1]

[0294]

[0295] In the chemical formula HI-1,

[0296] At least one of X'1 to X'6 is N, and the rest are CH, and

[0297] R309 to R314 are the same as or different from each other, and are each independently hydrogen; deuterium; cyano; substituted or unsubstituted alkyl; substituted or unsubstituted amine; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, or bond with an adjacent group to form a substituted or unsubstituted ring.

[0298] According to an exemplary embodiment of the present specification, X'1 to X'6 are N.

[0299] According to an exemplary embodiment of the present specification, R309 to R314 are cyano groups.

[0300] According to an exemplary embodiment of the present specification, Chemical Formula HI-1 is the following compound.

[0301]

[0302] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is suitably a material having high hole mobility: it can receive holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples thereof include organic materials based on arylamine, conductive polymers, block copolymers having both a conjugated portion and a non-conjugated portion, etc., but are not limited thereto.

[0303] The hole regulating layer is a layer that can improve the service life and efficiency of the device by regulating the holes transmitted from the hole transport layer so that the holes are smoothly injected into the light-emitting layer and preventing the electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer. As the hole regulating layer, known materials can be used without limitation, and the hole regulating layer can be formed between the light-emitting layer and the hole injection layer, between the light-emitting layer and the hole transport layer, or between the light-emitting layer and the layer that simultaneously injects and transports holes.

[0304] According to an exemplary embodiment of the present specification, the hole transport layer or the hole regulating layer includes a compound of the following Chemical Formula HT-1, but is not limited thereto.

[0305] [Chemical formula HT-1]

[0306]

[0307] In the chemical formula HT-1,

[0308] R315 to R317 are the same as or different from each other, and are each independently selected from any one of hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof, or are bonded to an adjacent group to form a substituted or unsubstituted ring,

[0309] r315 is an integer of 1 to 5, and when r315 is 2 or more, two or more R315 are the same as or different from each other, and

[0310] r316 is an integer of 1 to 5, and when r316 is 2 or more, two or more R316 are the same as or different from each other.

[0311] According to an exemplary embodiment of the present specification, R317 is any one selected from the following: a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a combination thereof.

[0312] According to an exemplary embodiment of the present specification, R317 is any one selected from the group consisting of: a carbazolyl group; a phenyl group; a biphenyl group; and a combination thereof.

[0313] According to an exemplary embodiment of the present specification, R315 and R316 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or bond with an adjacent group to form an alkyl-substituted aromatic hydrocarbon ring.

[0314] According to an exemplary embodiment of the present specification, R315 and R316 are the same as or different from each other, and are each independently a phenyl group or a phenanthryl group, or bond with an adjacent group to form an indene substituted with a methyl group.

[0315] According to an exemplary embodiment of the present specification, Chemical Formula HT-1 is any one of the following compounds.

[0316]

[0317] The electron regulating layer is a layer that regulates electrons transferred from the electron transporting layer to be smoothly injected into the light emitting layer, and a known material can be used without limitation.

[0318] According to an exemplary embodiment of the present specification, the electron adjustment layer includes a compound of the following Chemical Formula EG-1, but is not limited thereto.

[0319] [Chemical formula EG-1]

[0320]

[0321] In the chemical formula EG-1,

[0322] At least one of G'1 to G'18 is -L5-Ar5, and the others are hydrogen, or G'1 and G'18 are connected through -L51- to form a substituted or unsubstituted ring,

[0323] L5 is a direct bond; or a substituted or unsubstituted arylene group,

[0324] Ar5 is substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, and

[0325] L51 is O; or S.

[0326] According to an exemplary embodiment of the present specification, L51 is O.

[0327] According to an exemplary embodiment of the present specification, L51 is S.

[0328] According to an exemplary embodiment of the present specification, G'1 and G'18 are connected through -L51- to form a substituted or unsubstituted heterocyclic ring.

[0329] According to an exemplary embodiment of the present specification, G'1 and G'18 are linked through -L51- to form a substituted or unsubstituted xanthene ring; or a substituted or unsubstituted thioxanthene ring.

[0330] According to an exemplary embodiment of the present specification, G'1 and G'18 are connected through -O- to form a substituted or unsubstituted xanthene ring.

[0331] According to an exemplary embodiment of the present specification, G'1 and G'18 are linked through -S- to form a substituted or unsubstituted thioxanthene ring.

[0332] According to an exemplary embodiment of the present specification, G'1 and G'18 are linked through -O- to form a xanthene ring.

[0333] According to an exemplary embodiment of the present specification, G'1 and G'18 are linked through -S- to form a thioxanthene ring.

[0334] According to an exemplary embodiment of the present specification, L5 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0335] According to an exemplary embodiment of the present specification, L5 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0336] According to an exemplary embodiment of the present specification, L5 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0337] According to an exemplary embodiment of the present specification, L5 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0338] According to an exemplary embodiment of the present specification, L5 is a direct bond; or a phenylene group.

[0339] According to an exemplary embodiment of the present specification, Ar5 is a substituted or unsubstituted triazine group.

[0340] According to an exemplary embodiment of the present specification, Ar5 is a triazine group which is unsubstituted or substituted with a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

[0341] According to an exemplary embodiment of the present specification, Ar5 is a triazine group substituted with a phenyl group.

[0342] According to an exemplary embodiment of the present specification, EG-1 is the following compound.

[0343]

[0344] In an exemplary embodiment of the present specification, the light emitting layer includes a host and a dopant, and in this case, the host and the dopant are included in a weight ratio of 0.1:99.9 to 20:80.

[0345] Examples of host materials for the light-emitting layer include fused aromatic ring derivatives or heterocyclic compounds, etc. Specifically, examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and examples of heterocyclic compounds include carbazole derivatives, dibenzofuran, dibenzofuran derivatives, dibenzothiophene, dibenzothiophene derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but examples thereof are not limited thereto.

[0346] For the dopant used for the light-emitting layer, when the light-emitting layer emits red light, 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 (Alq3) can be used as a light-emitting dopant, but the light-emitting dopant is not limited thereto. When the light-emitting layer emits green light, a phosphorescent material such as planar tris(2-phenylpyridine)iridium (Ir(ppy)3) or a fluorescent material such as tris(8-hydroxyquinoline)aluminum (Alq3) can be used as a light-emitting dopant, but the light-emitting dopant is not limited thereto. When the light-emitting layer emits blue light, a phosphorescent material such as (4,6-F2ppy)2Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), a PFO-based polymer or a PPV-based polymer can be used as a light-emitting dopant, however, the light-emitting dopant is not limited thereto.

[0347] In an exemplary embodiment of the present specification, the light emitting layer includes one or more first compounds of Chemical Formula 1 of the present application and a second compound that is an anthracene derivative.

[0348] In an exemplary embodiment of the present specification, the light emitting layer may be composed of a single layer, but may also be a plural layer having two or more layers.

[0349] When the light emitting layer is a single layer, the first compound of Chemical Formula 1 and the second compound which is an anthracene derivative are contained in one layer. Such a single layer light emitting layer can be formed by co-depositing the first compound of Chemical Formula 1 and the second compound which is an anthracene derivative.

[0350] When the light-emitting layer has two or more layers, the first compound of Chemical Formula 1 and the second compound that is an anthracene derivative may be contained in one layer, and the first compound of Chemical Formula 1 and the second compound that is an anthracene derivative may be contained in different light-emitting layers. For example, the light-emitting layer may include a first light-emitting layer containing the first compound of Chemical Formula 1 and a second light-emitting layer containing the second compound that is an anthracene derivative. In this case, the second light-emitting layer may be disposed between the first light-emitting layer and the cathode. The first light-emitting layer and the second light-emitting layer may be disposed in contact with each other. When the first light-emitting layer and the second light-emitting layer each contain the compound of Chemical Formula 1 and the second compound that is an anthracene derivative as a host, the first light-emitting layer and the second light-emitting layer each further contain a dopant compound. In this case, the first light-emitting layer and the second light-emitting layer may contain the same type of dopant material, and may contain different types of dopant materials, but preferably contain the same type of dopant material.

[0351] In an exemplary embodiment of the present specification, a light-emitting layer having one or more layers includes the compound of Chemical Formula 1 and a second compound that is an anthracene derivative as a host.

[0352] In an exemplary embodiment of the present specification, the second compound that is an anthracene derivative may include at least one of a compound of the following Chemical Formula 2 and a compound of the following Chemical Formula 3. Specifically, the second compound that is an anthracene derivative is a mixed body including two different types of anthracene derivatives, and may include a compound of the following Chemical Formula 2 and a compound of the following Chemical Formula 3.

[0353] [Chemical formula 2]

[0354]

[0355] In chemical formula 2,

[0356] One or more of R11 to R20 are bonded to the * part of the following chemical formula 2-1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group,

[0357] [Chemical formula 2-1]

[0358]

[0359] L2 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0360] Ar2 is a substituted or unsubstituted aryl group, and

[0361] p is an integer from 1 to 3,

[0362] [Chemical formula 3]

[0363]

[0364] In chemical formula 3,

[0365] One or more of Y1 to Y10 are bonded to the * part of the following chemical formula 3-1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group,

[0366] [Chemical formula 3-1]

[0367]

[0368] A and B are the same as or different from each other and are each independently a substituted or unsubstituted aromatic hydrocarbon ring; or a substituted or unsubstituted aromatic heterocycle,

[0369] L3 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0370] q is an integer from 1 to 3.

[0371] The present inventors have discovered suitable conditions for a phenanthrofuran-type or phenanthrothiophene-type host (hereinafter, referred to as the compound of Chemical Formula 1) and an anthracene-type host (hereinafter, referred to as the compound of Chemical Formula 2 and the compound of Chemical Formula 3), which can be used as a blue fluorescent host material and can simultaneously provide a stable co-evaporation mixture after premixing.

[0372] The light-emitting layer of an organic light-emitting device showing excellent service life and efficiency requires more than two components (e.g., three or four components). For this purpose, three or four raw materials are required to prepare such a light-emitting layer, which is very complex and expensive compared to a standard two-component light-emitting layer with a single host and a dopant that requires only two raw materials. Premixing two or more materials and evaporating the two or more materials from one raw material can reduce the complexity of the preparation process. The selected hole transport host and another type of host, such as an electron transport host, can be mixed and co-evaporated from one crucible to achieve stable evaporation.

[0373] However, co-evaporation needs to be stable, i.e. the composition of the evaporated film needs to remain constant during the manufacturing process. Any compositional changes may have an adverse effect on the device performance. It can be assumed that in order to obtain stable co-evaporation from a mixture of compounds under vacuum, the materials need to have the same evaporation temperature under the same conditions. However, this will not be the only parameter to be considered. When two compounds are mixed together, the compounds may interact with each other and their evaporation characteristics may be different from their individual properties. On the other hand, materials with slightly different evaporation temperatures can produce stable co-evaporated mixtures. Therefore, it is extremely difficult to achieve stable co-evaporated mixtures. To date, there are tens of thousands of available host materials in the literature, but only very few examples of stable co-evaporated mixtures. The "evaporation temperature" of the material is determined in the sublimation crucible of a vacuum deposition tool such as a VTE tool. At a deposition rate of 1 × 10 -6 Torr to 1×10 -9 As will be appreciated by those skilled in the art, the various measurements disclosed in this specification, such as temperature, pressure, and deposition rate, are expected to have nominal variations due to the expected tolerance errors in the measurements used to calculate the quantitative values.

[0374] The disclosure of this specification describes a new class of two different types of anthracene hosts (Chemical Formula 2 and Chemical Formula 3) that can be premixed to provide a stable co-evaporation mixture that can be used as a blue fluorescent host material. Multiple factors other than temperature may contribute to evaporation, such as the miscibility of different materials and different phase transitions. The inventors have found that when two materials have similar evaporation temperatures and similar mass loss rates or similar vapor pressures, the materials can be continuously co-evaporated. The mass loss rate is defined as the percentage of mass loss over time (minutes) and is determined by measuring the time it takes for the first 10% of the mass to decrease, which is measured by thermogravimetric analysis (TGA) at the same constant temperature given for each compound after reaching a stable evaporation state under the same experimental conditions. The constant temperature given is a temperature point selected so that the value of the mass loss rate is about 0.05% / minute to 0.50% / minute. Those skilled in the art will understand that in order to compare two parameters, the experimental conditions need to be constant. Methods for measuring mass loss rate and vapor pressure are well known in the art and can be found, for example, in the literature (Bull et al. Mater. Sci. 2011, 34, 7).

[0375] In the two-component mixture of the blue fluorescent host in the prior art, the prior art document of the present invention is disclosed in JP 6328890B2. In order to prepare a blue fluorescent light-emitting layer with such a mixed host material, three evaporation sources are required: two types of hosts and blue fluorescent dopants. The concentration of the co-host and the dopant is important for the device performance, and the deposition rate of each component is usually measured separately during deposition. This makes the manufacturing process complicated and requires a lot of cost. Therefore, it is expected to reduce the amount of raw materials by mixing two or more components.

[0376] When two types of blue fluorescent hosts are premixed during the preparation of the mixture by thermal sublimation and the difference in composition is within a certain range, it means that the two blue fluorescent hosts can be co-deposited from one raw material. Uniform co-evaporation of the two hosts is important for the sustainability of the performance of the device made from the mixture.

[0377] Hereinafter, the compound of Chemical Formula 2 will be described in detail.

[0378] According to an exemplary embodiment of the present specification, one to three of R11 to R20 are bonded to the * portion of Chemical Formula 2-1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group.

[0379] According to another exemplary embodiment, one to three of R11 to R20 are bonded to the * portion of Chemical Formula 2-1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted aryl group having 2 to 60 carbon atoms; or a substituted or unsubstituted silyl group.

[0380] In another exemplary embodiment, R19 and R20 are bonded to the * portion of Chemical Formula 2-1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group.

[0381] According to yet another exemplary embodiment, R19, R20 and R18 are bonded to the * portion of Chemical Formula 2-1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group.

[0382] In yet another exemplary embodiment, R19, R20, and R17 are bonded to the * portion of Chemical Formula 2-1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group.

[0383] According to an exemplary embodiment of the present specification, among R11 to R20, substituents not bonded to Chemical Formula 2-1 are the same as or different from each other, and are each independently hydrogen, deuterium, or a dibenzofuranyl group.

[0384] According to an exemplary embodiment of the present specification, p is an integer of 3, and three L2s are the same as or different from each other.

[0385] In yet another exemplary embodiment, p is an integer of 2, and two L2 are the same as or different from each other.

[0386] According to an exemplary embodiment of the present specification, L2 is a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms. L2 may be substituted with deuterium.

[0387] In yet another exemplary embodiment, L2 is a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

[0388] According to another exemplary embodiment, L2 is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted phenanthrenyl group; or a substituted or unsubstituted triphenylene group.

[0389] In another exemplary embodiment, L2 is a direct bond; unsubstituted or deuterium-substituted phenylene; unsubstituted or deuterium-substituted biphenylene; unsubstituted or deuterium-substituted naphthylene; unsubstituted or deuterium-substituted phenanthrenylene; or unsubstituted or deuterium-substituted triphenylene.

[0390] According to an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms. Ar2 may be substituted with deuterium.

[0391] In another exemplary embodiment, Ar2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0392] According to another exemplary embodiment, Ar2 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; or a substituted or unsubstituted triphenylene group.

[0393] In another exemplary embodiment, Ar2 is unsubstituted or deuterium-substituted phenyl; unsubstituted or deuterium-substituted biphenyl; unsubstituted or deuterium-substituted terphenyl; unsubstituted or deuterium-substituted naphthyl; unsubstituted or deuterium-substituted phenanthrenyl; or unsubstituted or deuterium-substituted triphenylene.

[0394] As the compound of Chemical Formula 2, compounds described in JP 4070676 B2, KR 1477844 B1, US6465115B2, JP 3148176B2, JP 4025136B2, JP 4188082B2, JP 5015459B2, KR 1979037 B1, KR 1550351 B1, KR 1503766 B1, KR 0826364 B1, KR 0749631B1, KR 1115255B1, KR1538534B1 and the like may be used.

[0395] Hereinafter, the compound of Chemical Formula 3 will be described in detail.

[0396] According to an exemplary embodiment of the present specification, one or more of Y1 to Y10 are bonded to the * portion of Chemical Formula 3-1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0397] According to an exemplary embodiment of the present specification, one to three of Y1 to Y10 are bonded to the * portion of Chemical Formula 3-1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group.

[0398] In an exemplary embodiment of the present specification, one to three of Y1 to Y10 are bonded to the * portion of Chemical Formula 3-1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or a substituted or unsubstituted silyl group.

[0399] In another exemplary embodiment, Y7, Y8 or Y9 is bonded to the * portion of Chemical Formula 3-1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group.

[0400] According to another exemplary embodiment, Y7 and Y9 are bonded to the * portion of Chemical Formula 3-1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group.

[0401] According to yet another exemplary embodiment, Y9 and Y10 are bonded to the * portion of Chemical Formula 3-1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group.

[0402] According to an exemplary embodiment of the present specification, in Y1 to Y10, the substituents not bonded to Chemical Formula 3-1 are the same as or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. In Y1 to Y10, the substituents not bonded to Chemical Formula 2-1 may be substituted with deuterium.

[0403] According to another exemplary embodiment, in Y1 to Y10, the substituents not bonded to Chemical Formula 3-1 are the same as or different from each other, and are each independently hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthryl; or substituted or unsubstituted triphenylene, and the substituents may be further substituted by deuterium; unsubstituted or deuterium-substituted phenyl; unsubstituted or deuterium-substituted biphenyl; unsubstituted or deuterium-substituted terphenyl; unsubstituted or deuterium-substituted naphthyl; unsubstituted or deuterium-substituted phenanthryl; or unsubstituted or deuterium-substituted triphenylene.

[0404] In an exemplary embodiment of the present specification, q is an integer of 1 to 3, and when q is 2 or more, two or more L3 are the same as or different from each other.

[0405] According to an exemplary embodiment of the present specification, L3 is a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms. L2 may be substituted with deuterium.

[0406] In another exemplary embodiment, L3 is a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

[0407] According to another exemplary embodiment, L3 is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted phenanthrenyl group; or a substituted or unsubstituted triphenylene group.

[0408] In yet another exemplary embodiment, L3 is a direct bond; unsubstituted or deuterium-substituted phenylene; unsubstituted or deuterium-substituted biphenylene; unsubstituted or deuterium-substituted naphthylene; unsubstituted or deuterium-substituted phenanthrenylene; or unsubstituted or deuterium-substituted triphenylene.

[0409] According to an exemplary embodiment of the present specification, A and B are the same as or different from each other, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; or a substituted or unsubstituted aromatic heterocycle having 2 to 60 carbon atoms.

[0410] In an exemplary embodiment of the present specification, A and B are the same as or different from each other, and are each independently an aromatic hydrocarbon ring having 6 to 60 carbon atoms which is unsubstituted or substituted with one or more substituents selected from deuterium and unsubstituted or deuterium-substituted aryl groups; or an aromatic heterocyclic ring having 2 to 60 carbon atoms which is unsubstituted or substituted with one or more substituents selected from deuterium and unsubstituted or deuterium-substituted aryl groups.

[0411] According to another exemplary embodiment, A and B are the same as or different from each other, and are each independently an aromatic hydrocarbon ring having 6 to 60 carbon atoms which is unsubstituted or substituted with one or more substituents selected from deuterium and an unsubstituted or deuterium-substituted aryl group having 6 to 30 carbon atoms; or an aromatic heterocycle having 2 to 60 carbon atoms which is unsubstituted or substituted with one or more substituents selected from deuterium and an unsubstituted or deuterium-substituted aryl group having 6 to 30 carbon atoms.

[0412] In another exemplary embodiment, A and B are the same as or different from each other, and are each independently substituted or unsubstituted benzene; substituted or unsubstituted naphthalene; substituted or unsubstituted phenanthrene; substituted or unsubstituted triphenylene; or substituted or unsubstituted dibenzofuran.

[0413] According to yet another exemplary embodiment, A and B are the same as or different from each other, and are each independently benzene which is unsubstituted or substituted with one or more substituents selected from deuterium and an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with deuterium; naphthalene which is unsubstituted or substituted with one or more substituents selected from deuterium and an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with deuterium; phenanthrene which is unsubstituted or substituted with one or more substituents selected from deuterium and an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with deuterium; triphenylene which is unsubstituted or substituted with one or more substituents selected from deuterium and an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with deuterium; or dibenzofuran which is unsubstituted or substituted with one or more substituents selected from deuterium and an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with deuterium.

[0414] As the compound of Chemical Formula 3, compounds described in KR 1964435 B1, KR 1899728 B1, KR1975945B1, KR 2018-0098122 A, KR 2018-0102937 A, KR2018-0103352A, KR 1538534 B1, etc. may be used.

[0415] In the organic light-emitting device according to an exemplary embodiment of the present specification, the sublimation temperature (T 升华1) and the sublimation temperature of the second compound (T 升华2 ) satisfies the following formula (1):

[0416] |T 升华1 -T 升华2 |≤20℃ — Formula (1)

[0417] When the above configuration is satisfied, electrons are easily injected into the triplet energy level provided by the first compound of Chemical Formula 1 while reproducing the low voltage and high efficiency provided by the second compound, so that there is an advantage of improved luminous efficiency due to an increase in the proportion of formed excitons.

[0418] In an organic light-emitting device according to an exemplary embodiment of the present specification, the light-emitting layer includes a first light-emitting layer and a second light-emitting layer,

[0419] wherein the first light emitting layer comprises the compound of Chemical Formula 1 as a first host material, and

[0420] The second light emitting layer includes, as a second host material, at least one of the compound of Chemical Formula 2 and the compound of Chemical Formula 3. When such a configuration is satisfied, the efficiency of the organic light emitting device can be additionally improved.

[0421] In the organic light emitting device according to an exemplary embodiment of the present specification, the second light emitting layer is provided between the first light emitting layer and the cathode.

[0422] The organic light emitting device according to an exemplary embodiment of the present specification is configured such that the first light emitting layer and the second light emitting layer are in direct contact with each other. When such a configuration is satisfied, the efficiency of the organic light emitting device can be further improved.

[0423] In the organic light emitting device according to an exemplary embodiment of the present specification, the first light emitting layer includes a combination of two or more compounds of Chemical Formula 1 as a first host material.

[0424] In the organic light emitting device according to an exemplary embodiment of the present specification, the light emitting layer further includes a dopant material.

[0425] As described above, the light-emitting layer may include a light-emitting layer having a single layer or two or more layers. When the light-emitting layer is a single layer, for the compound of Chemical Formula 1 and the second compound that is an anthracene derivative, the light-emitting layer may also include a single dopant material or a combination of multiple dopant materials. In addition, when the light-emitting layer has two layers and includes a first light-emitting layer including the compound of Chemical Formula 1 and a second light-emitting layer including the second compound that is an anthracene derivative, each light-emitting layer may include the same type of dopant material as each other, or different types of dopant materials. Preferably, two or more light-emitting layers include the same type of dopant material.

[0426] In the organic light emitting device according to an exemplary embodiment of the present specification, the dopant material is a fluorescent dopant.

[0427] In the organic light emitting device according to an exemplary embodiment of the present specification, the fluorescent dopant is a blue fluorescent dopant.

[0428] In the organic light emitting device according to an exemplary embodiment of the present specification, the blue fluorescent dopant is a pyrene-based compound or a non-pyrene-based compound.

[0429] In the organic light emitting device according to an exemplary embodiment of the present specification, the non-pyrene-based compound is an arylamine-based compound or a boron-based compound.

[0430] When a non-pyrene-based compound is used as a fluorescent dopant, efficiency may be improved and lifetime may be increased due to a characteristic of a narrow full width at half maximum, compared to a pyrene-based compound.

[0431] The pyrene-based compound may be a pyrene-based compound having a smaller band gap than a host material in which a diarylamine is substituted, for example, BD02 (N1,N1,N6,N6-tetraphenylpyrene-1,6-diamine).

[0432] As a compound that is not pyrene or a pyrene derivative, non-pyrene-based compounds may include metal complexes (iridium complexes, platinum complexes, etc.), boron-based compounds (DABNA-1, etc.), arylamine-based compounds (coumarin 6, etc.), but are not limited thereto.

[0433] In an exemplary embodiment of the present specification, the pyrene-based compound may be a compound represented by the following Chemical Formula Z1, and the non-pyrene-based compound may be a compound represented by the following Chemical Formula Z2 (arylamine-based compound) and Chemical Formula Z3 (boron-based compound).

[0434] [Chemical formula Z1]

[0435]

[0436] [Chemical formula Z2]

[0437]

[0438] [Chemical formula Z3]

[0439]

[0440] In chemical formulae Z1 to Z3,

[0441] X3 and X4 are each hydrogen or deuterium, or are directly bonded to each other to form a ring,

[0442] R41 and R42 are the same as or different from each other and are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group,

[0443] Ar31 to Ar34, Ar41 to Ar44, Ar51 and Ar52 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,

[0444] Cy1 to Cy3 are the same as or different from each other, and are each independently a monocyclic to polycyclic aromatic hydrocarbon ring, or a monocyclic to polycyclic aromatic heterocyclic ring,

[0445] R31, R32, R43 to R46, and R51 to R53 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or bond with an adjacent substituent to form a substituted or unsubstituted ring, and

[0446] R41, R42, and R51 to R53 are each an integer of 0 to 4, and when R41, R42, and R51 to R53 are 2 or more, the substituents in brackets are the same as or different from each other.

[0447] In an exemplary embodiment of the present specification, Ar31 to Ar34, Ar41 to Ar44, Ar51, and Ar52 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0448] In an exemplary embodiment of the present specification, Ar31 to Ar34, Ar41 to Ar44, Ar51 and Ar52 are the same as or different from each other, and are each independently a C6 to C20 aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group and a C1 to C6 alkyl group, or a substituent selected from two or more groups in the above group connected; or a C2 to C20 heterocyclic group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group and a C1 to C6 alkyl group, or a substituent selected from two or more groups in the above group connected.

[0449] In an exemplary embodiment of the present specification, Cy1 to Cy3 are the same as or different from each other, and are each independently a monocyclic to tricyclic aromatic hydrocarbon ring; or a monocyclic to tricyclic aromatic heterocyclic ring containing N, O, or S.

[0450] In an exemplary embodiment of the present specification, Cy1 to Cy3 are the same as or different from each other and are each independently a benzene ring; a naphthalene ring; a furan ring; a thiophene ring; a benzofuran ring; a benzothiophene ring; a dibenzofuran ring; or a dibenzothiophene ring, and may be further condensed with a C5 to C10 aliphatic hydrocarbon ring.

[0451] In an exemplary embodiment of the present specification, R31, R32, R43 to R46, and R51 to R53 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C10 alkyl group; a substituted or unsubstituted C1 to C30 alkylsilyl group; a substituted or unsubstituted C6 to C90 arylsilyl group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C1 to C30 alkylamine group; a substituted or unsubstituted C6 to C60 arylamine group; a substituted or unsubstituted C2 to C60 heteroarylamine group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heterocyclic group, or bonded to an adjacent substituent to form a C3 to C30 hydrocarbon ring; or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0452] In an exemplary embodiment of the present specification, R31 and R32 are hydrogen or deuterium.

[0453] In an exemplary embodiment of the present specification, Ar31 to Ar34 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0454] In an exemplary embodiment of the present specification, Ar31 to Ar34 are the same as or different from each other, and are each independently an unsubstituted or alkyl-substituted C6 to C30 aryl group; or a substituted or unsubstituted O-containing C2 to C30 heterocyclic group.

[0455] In an exemplary embodiment of the present specification, Ar31 to Ar34 are the same as or different from each other, and are each independently an unsubstituted or alkyl-substituted phenyl group; or a substituted or unsubstituted dibenzofuranyl group.

[0456] In an exemplary embodiment of the present specification, Chemical Formula Z3, which is a boron-based compound, is any one of the following Chemical Formulas Z3-1 to Z3-3.

[0457] [Chemical formula Z3-1]

[0458]

[0459] [Chemical formula Z3-2]

[0460]

[0461] [Chemical formula Z3-3]

[0462]

[0463] In chemical formulae Z3-1 to Z3-3,

[0464] R51 to R53, r52, Ar51 and Ar52 are the same as those defined in Chemical Formula Z3,

[0465] X5 is O or S, and

[0466] r521 is an integer of 0 to 2, and when r521 is 2 or more, R52 are the same as or different from each other.

[0467] In an exemplary embodiment of the present specification, Ar51 and Ar52 are the same as or different from each other, and are each independently a C6 to C30 aryl group in which an aliphatic hydrocarbon ring is fused or not fused; or a C2 to C30 heterocyclic group, and the aryl group or the heterocyclic group is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group and a C1 to C10 alkyl group, or a substituent selected from two or more groups connected to each other.

[0468] In an exemplary embodiment of the present specification, the aryl group or heterocyclic group of Ar51 includes a substituent replacing hydrogen at the para position relative to N to which the aryl group or heterocyclic group is attached.

[0469] In an exemplary embodiment of the present specification, the aryl group or heterocyclic group of Ar52 includes a substituent replacing hydrogen at the para position relative to N to which the aryl group or heterocyclic group is attached.

[0470] In an exemplary embodiment of the present specification, R51 to R53 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C10 alkyl group; a substituted or unsubstituted C1 to C30 alkylsilyl group; a substituted or unsubstituted C6 to C90 arylsilyl group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C1 to C30 alkylamine group; a substituted or unsubstituted C6 to C60 arylamine group; a substituted or unsubstituted C2 to C60 heteroarylamine group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heterocyclic group, or bonded to an adjacent substituent to form a C3 to C30 aliphatic hydrocarbon ring; or a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring.

[0471] In an exemplary embodiment of the present specification, R51 to R53 are the same as or different from each other, and are each independently hydrogen; deuterium; methyl; tert-butyl; phenyl; tert-butyl-substituted phenyl; diphenylamine; or bis((tert-butyl)phenyl)amine.

[0472] In an exemplary embodiment of the present specification, two adjacent R51, two adjacent R52, or two adjacent R53 are bonded to each other to form a substituted or unsubstituted ring. In this case, the ring is a C3 to C30 aliphatic hydrocarbon ring; or a C6 to C30 aromatic hydrocarbon ring, and specifically a cyclopentene, cyclohexene, tetrahydronaphthalene ring, benzene ring or naphthalene ring.

[0473] In an exemplary embodiment of the present specification, the dopant may be selected from the following structures, and is not limited thereto.

[0474]

[0475] In an exemplary embodiment of the present specification, based on 100 parts by weight of the host material, the dopant material may be included in the light-emitting layer in an amount of 0.01 parts by weight to 50 parts by weight, 0.1 parts by weight to 30 parts by weight, 1 part by weight to 10 parts by weight, or 2 parts by weight. Within the above range, energy transfer from the host to the dopant occurs effectively. In this case, 100 parts by weight of the host material is based on the total weight of the compound of Chemical Formula 1 and / or the second compound.

[0476] When the above configuration is satisfied, the efficiency of the organic light emitting device can be further improved.

[0477] In the organic light emitting device according to an exemplary embodiment of the present specification, a deuterium substitution rate of at least one of the first compound and the second compound of Chemical Formula 1 is each independently 1% or more and 100% or less.

[0478] In an exemplary embodiment of the present specification, the deuterium substitution rate of at least one of the first compound and the second compound of Chemical Formula 1 may be each independently 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more.

[0479] In an exemplary embodiment of the present specification, the deuterium substitution rate of at least one of the first compound and the second compound of Chemical Formula 1 may be each independently 100% or less, 99% or less, 98% or less, 97% or less, 96% or less, or 95% or less.

[0480] According to an exemplary embodiment of the present specification, deuterium substitution rates of both the first compound and the second compound of Chemical Formula 1 are 100%.

[0481] The deuterium substitution rate can be calculated by the method described above. According to another example, the second compound is directly substituted with at least one deuterium. The light-emitting layer of the organic light-emitting device is a region that emits light and is a region where the molecular loss caused by energy is large. Since the carbon-deuterium bond is stronger than the carbon-hydrogen bond, and deuterium has a higher mass value than hydrogen, the zero-point energy with carbon is reduced, and the bond energy is high, so by replacing the carbon-hydrogen bond contained in the molecule of the compound of Chemical Formula 2 with a carbon-deuterium bond to increase the bond energy of the molecule, a device with excellent service life can be obtained.

[0482]

[0483] The organic light emitting device including Chemical Formula 1 and / or the second compound having a certain deuterium substitution rate according to an exemplary embodiment of the present specification has improved heat resistance and has an effect of improving service life.

[0484] In the organic light-emitting device according to an exemplary embodiment of the present specification, the triplet energy level (T h1 ) is 2.30 eV or greater.

[0485] In an exemplary embodiment of the present specification, the triplet energy level (T h1 ) can be 2.30 eV or greater, 2.40 eV or greater, or 2.50 eV or greater.

[0486] In the organic light-emitting device according to an exemplary embodiment of the present specification, the triplet energy level (T h1 ) is higher than the triplet energy level (T h2 ).

[0487] In the organic light-emitting device according to an exemplary embodiment of the present specification, the triplet energy level (T h1 ) can satisfy 2.30eV≤T h1 ≤2.90eV.

[0488] In an exemplary embodiment of the present specification, the triplet energy level (T h1 ) can be greater than 2.30 eV, greater than 2.40 eV, or greater than 2.50 eV.

[0489] In an exemplary embodiment of the present specification, the triplet energy level (T h1 ) can be less than 2.90 eV, less than 2.80 eV, or less than 2.70 eV.

[0490] In the organic light-emitting device according to an exemplary embodiment of the present specification, the triplet energy level (T h2 ) can satisfy 1.40eV≤T h2 ≤1.80eV.

[0491] In an exemplary embodiment of the present specification, the triplet energy level (T h2 ) may be greater than 1.40 eV, greater than 1.45 eV, greater than 1.50 eV, or greater than 1.55 eV.

[0492] In an exemplary embodiment of the present specification, the triplet energy level (T h2 ) can be less than 1.80 eV, less than 1.75 eV, less than 1.70 eV, or less than 1.65 eV.

[0493] In the organic light-emitting device according to an exemplary embodiment of the present specification, the triplet energy level (T h1 ) and the triplet energy level of the second compound (T h2 ) can satisfy the following formula (2).

[0494] Δ(T h1 -T h2 )≤1.50 eV — Formula (2)

[0495] In an exemplary embodiment of the present specification, the triplet energy level (T h1 ) and the triplet energy level of the second compound (T h2 ) difference (Δ(T h1 -T h2 )) can be 1.50 eV or less, 1.45 eV or less, 1.40 eV or less, 1.35 eV or less, or 1.30 eV or less.

[0496] In the organic light-emitting device according to an exemplary embodiment of the present specification, the triplet energy level (T h1 ), the triplet energy level of the second compound (T h2 ) and the triplet energy level of the blue fluorescent dopant (T BD ) can satisfy at least one of the following equations (3) and (4).

[0497] Δ(T BD -T h1 )≤0.40eV—Formula (3) and

[0498] Δ(T BD -T h2 )≥0.40 eV — Formula (4)

[0499] In an exemplary embodiment of the present specification, the triplet energy level (T h1 ) and the triplet energy level of the blue fluorescent dopant (T BD ) difference (Δ(T BD -T h1 )) can be 0.40 eV or less, 0.35 eV or less, or 0.30 eV or less.

[0500] In an exemplary embodiment of the present specification, the triplet energy level (T h2 ) and the triplet energy level of the blue fluorescent dopant (T BD ) difference (Δ(T BD -T h2 )) can be 0.40 eV or greater, 0.45 eV or greater, or 0.50 eV or greater.

[0501] When any of the configurations is satisfied, electrons are easily injected into the triplet level of the dopant, so that efficiency is improved due to an increase in the ratio of formed excitons.

[0502] In this specification, the triplet energy level (T h1 ) can be measured using a spectroscopic instrument capable of measuring fluorescence and phosphorescence, and the measurement conditions are determined by: preparing a 10% concentration of iodine using toluene or tetrahydrofuran (THF) as a solvent under an extremely low temperature state using liquid nitrogen. -6 M, irradiate the solution with a light source in the absorption wavelength band of the material to exclude singlet light emission from the luminescence spectrum, and analyze the luminescence spectrum in the triplet energy level. When electrons are excited from the light source, since the time that electrons stay in the triplet energy level is much longer than the time that electrons stay in the singlet energy level, the two components can be separated from each other in an extremely low temperature state.

[0503] In this specification, triplet energy (E T1 ) can be calculated by the following method. After cooling the sample to 77K, the sample for measuring phosphorescence is irradiated with excitation light (360nm), the phosphorescence intensity is measured using a streak camera, and then the tangent line of the rising point of the phosphorescence spectrum is plotted to obtain the wavelength value λ edge [nm] at the intersection of the tangent line and the x-axis, and the E converted into an energy value can be calculated by substituting the wavelength value into the following formula (6): T1 In this case, the luminescence spectrum was measured using a nitrogen laser (MNL200, manufactured by Lasertechnik Berlin GmbH) and a streak camera (C4334, manufactured by HamamatsuPhotonics KK).

[0504] E T1 [eV] = 1239.85 / λedge - Formula (6)

[0505] In an exemplary embodiment of the present specification, the triplet energy level (E T1 Specifically, the calculated values ​​of triplet energy can be obtained by time-dependent-density functional theory (TD-DFT) relative to the structure optimized by density functional theory (DFT) using B3LYP (Becke, three-parameter, Lee-Yang-Parr) as the functional and 6-31G* as the basis function.

[0506] In the organic light emitting device according to an exemplary embodiment of the present specification, in the light emitting layer, the maximum light emission wavelengths (λmax) of the compound of Chemical Formula 1 and the second compound may each be within a range of 400 nm or more and 500 nm or less.

[0507] Preferably, the maximum emission wavelengths (λmax) of the compound of Chemical Formula 1 and the second compound may each be within the range of 400 nm or more and 485 nm or less, or 400 nm or more and 470 nm or less. When such a configuration is satisfied, the light emitting layer may emit blue light.

[0508] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer, and the electron transport material is appropriately a material with high electron mobility that can well receive electrons from the cathode and transfer the electrons to the light-emitting layer. Specific examples thereof include: Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the relevant technology. In particular, suitable examples of cathode materials are typical materials with low work functions, followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

[0509] According to an exemplary embodiment of the present specification, the electron transport layer includes a compound of the following Chemical Formula ET-1, but is not limited thereto.

[0510] [Chemical formula ET-1]

[0511]

[0512] In the chemical formula ET-1,

[0513] At least one of Z11 to Z13 is N, and the rest are CH,

[0514] L601 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0515] Ar601 and Ar602 are the same as or different from each other and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0516] l601 is an integer of 1 to 5, and when l601 is 2 or greater, two or more L601 are the same as or different from each other.

[0517] According to an exemplary embodiment of the present specification, L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0518] According to an exemplary embodiment of the present specification, L601 is a phenylene group; a biphenylene group; or a naphthylene group.

[0519] According to an exemplary embodiment of the present specification, Ar601 and Ar602 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

[0520] According to an exemplary embodiment of the present specification, Ar601 and Ar602 are phenyl groups.

[0521] According to an exemplary embodiment of the present specification, Chemical Formula ET-1 is the following compound.

[0522]

[0523] The electron injection layer is a layer that injects electrons from the electrode, and the electron injection material is preferably a compound that has the ability to transport electrons, has an effect of injecting electrons from the cathode and has an excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, prevents the excitons generated by the light-emitting layer from moving to the hole injection layer, and is also excellent in the ability to form a thin film. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone, etc., and their derivatives; metal complex compounds, nitrogen-containing 5-membered ring derivatives; etc., but not limited thereto.

[0524] 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.

[0525] A covering layer is formed to prevent a large amount of light from being lost through total reflection of light in an organic light-emitting device, and the covering layer has the property of being able to fully protect the underlying negative electrode and light-emitting layer from external moisture penetration or contamination, and has a high refractive index, and thus can prevent light loss caused by total reflection, and materials in the related field can be used without restriction.

[0526] According to an exemplary embodiment of the present specification, the covering layer includes a compound of the following Chemical Formula CP-1, but is not limited thereto.

[0527] [Chemical formula CP-1]

[0528]

[0529] In the chemical formula CP-1,

[0530] L501 and L502 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0531] R501 and Ar501 to Ar504 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

[0532] According to an exemplary embodiment of the present specification, L501 and L502 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0533] According to an exemplary embodiment of the present specification, L501 and L502 are phenylene groups.

[0534] According to an exemplary embodiment of the present specification, R501 and Ar501 to Ar504 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, or are bonded to an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0535] According to an exemplary embodiment of the present specification, R501 and Ar501 to Ar504 are phenyl groups, or are bonded with adjacent groups to form unsubstituted or phenyl-substituted carbazole.

[0536] According to an exemplary embodiment of the present specification, Ar501 is bonded to L501 to form a phenyl-substituted carbazole.

[0537] According to an exemplary embodiment of the present specification, Ar503 is bonded to L503 to form a phenyl-substituted carbazole.

[0538] According to an exemplary embodiment of the present specification, Chemical Formula CP-1 is the following compound.

[0539]

[0540] 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.

[0541] The organic light emitting device according to the present specification may be included in and used in various electronic devices. For example, the electronic device may be a display panel, a touch panel, a solar module, a lighting device, etc., and is not limited thereto.

[0542] Embodiments of the invention

[0543] Hereinafter, the present application will be described in detail with reference to the embodiments for specifically describing the present application. However, the embodiments according to the present application can be modified in various forms, and should not be interpreted as the scope of the present application being limited to the embodiments described in detail below. The embodiments of the present application are provided to more completely illustrate the present application to those of ordinary skill in the art.

[0544] 1-1) Synthesis of Chemical Formula A1

[0545]

[0546] Here, ring A is a monocyclic or polycyclic hydrocarbon ring.

[0547] After SM1 (1 equivalent) and SM2 (1.1 equivalents) were added to tetrahydrofuran (THF) (excess), a 2M potassium carbonate aqueous solution (30 volume ratio compared to THF) was added thereto, and tetrakistriphenylphosphine palladium (Pd(PPh3)4, 2 mol%) was added thereto, and the resulting mixture was stirred for 10 hours under heating at 85°C. After the temperature was lowered to room temperature and the reaction was terminated, the layers were separated by removing the potassium carbonate aqueous solution, and the residue was column-filtered with hexane and ethyl acetate to prepare Chemical Formula A1 (A1-1 to A1-8).

[0548] A1-1 to A1-8 in [Table A1] were synthesized in the same manner as in the method for synthesizing Chemical Formula A1, except that SM1 and SM2 were changed.

[0549] [Table A1]

[0550]

[0551]

[0552] 1-2) Synthesis of Chemical Formula A2

[0553]

[0554] Here, ring A is a monocyclic or polycyclic hydrocarbon ring.

[0555] Compound A1 dissolved in tetrahydrofuran (excess) was dissolved under nitrogen and cooled to -78 °C. 2.5M n-BuLi (1.2 equivalents) was added dropwise thereto, the resulting mixture was stirred for 1 hour, iodine (1.1 equivalents) was then added thereto, and the resulting mixture was stirred for 10 hours. After the temperature was raised to room temperature (rt), 1N hydrogen chloride solution was added dropwise thereto, and the organic layer was extracted, followed by further extraction with water twice. After removing the solvent, the residue was passed through a column with hexane and ethyl acetate to prepare chemical formula A2 (A2-1 to A2-8).

[0556] A2-1 to A2-8 in [Table A2] were synthesized in the same manner as in the method for synthesizing Chemical Formula A2, except that SM1 and SM2 were changed.

[0557] [Table A2]

[0558]

[0559]

[0560] 1-3) Synthesis of Chemical Formula A3

[0561]

[0562] Here, ring A is a monocyclic or polycyclic hydrocarbon ring.

[0563] Compound A2 (1 equivalent), trimethylsilyl acetylene (TMS-≡, 5 equivalents), tetrakistriphenylphosphine palladium (Pd(PPh3)4, 0.1 equivalent), copper iodide (CuI, 1 equivalent) and triethylamine (TEA, excess) were placed in a container, and the resulting mixture was stirred for 5 hours under heating at 70°C. After the reaction was terminated, the resulting product was cooled to room temperature, passed through a filter filled with diatomaceous earth / silica gel, and washed with chloroform, the solvent was removed, and the residue was columned with hexane and ethyl acetate to prepare Chemical Formula A3 (A3-1 to A3-8).

[0564] A3-1 to A3-8 in [Table A3] were synthesized in the same manner as in the method for synthesizing Chemical Formula A3, except that A2 was changed.

[0565] [Table A3]

[0566]

[0567]

[0568] 1-4) Synthesis of Chemical Formula A4

[0569]

[0570] Here, ring A is a monocyclic or polycyclic hydrocarbon ring.

[0571] Compound A3 (1 equivalent) is dissolved in acetonitrile (AN, excess), silver fluoride (1.4 equivalents) is added thereto, the resulting mixture is stirred for 30 minutes, and then N-iodosuccinimide (NIS, 1.4 equivalents) is added thereto. After the mixture is stirred at room temperature for 2 hours, it is determined that the reaction has terminated, and the resulting product is then filtered and washed with acetonitrile. The solvent is removed by distillation under reduced pressure, and the residue is passed through a column with hexane and ethyl acetate to prepare chemical formula A4 (A4-1 to A4-8).

[0572] A4-1 to A4-8 in [Table A4] were synthesized in the same manner as in the method for synthesizing Chemical Formula A4, except that A3 was changed.

[0573] [Table A4]

[0574]

[0575]

[0576] 1-5) Synthesis of Chemical Formula A5

[0577]

[0578] Here, ring A is a monocyclic or polycyclic hydrocarbon ring.

[0579] Compound A4 (1 equivalent), platinum chloride (0.05 equivalent) and toluene (excess) were placed in a container, the resulting mixture was stirred at 100° C. for 3 hours, the reaction was determined to be terminated, and then the resulting product was cooled to room temperature. The product was filtered through a diatomaceous earth / silica gel pad, the solvent was removed by distillation under reduced pressure, and the residue was then columned with hexane and ethyl acetate to prepare Chemical Formula A5 (A5-1 to A5-8).

[0580] A5-1 to A5-8 in [Table A5] were synthesized in the same manner as in the method for synthesizing Chemical Formula A5, except that A4 was changed.

[0581] [Table A5]

[0582]

[0583]

[0584] 1-6) Synthesis of Chemical Formula A6

[0585]

[0586] Here, ring A is a monocyclic or polycyclic hydrocarbon ring.

[0587] After dissolving compound A5 (1 equivalent) in dichloromethane (excess), boron tribromide (BBr3, 1.4 equivalents) was added dropwise thereto, and the resulting mixture was stirred for 2 hours. After the reaction was completed, the reactant was added to water, extracted, and then the extract was washed with water, the solvent was removed by distillation under reduced pressure, hexane was added thereto, and the resulting mixture was stirred for 3 hours, and then filtered to prepare chemical formula A6 (A6-1 to A6-8).

[0588] A6-1 to A6-8 in [Table A6] were synthesized in the same manner as in the method for synthesizing Chemical Formula A6, except that A5 was changed.

[0589] [Table A6]

[0590]

[0591]

[0592] 1-7) Synthesis of Chemical Formula A7

[0593]

[0594] Here, ring A is a monocyclic or polycyclic hydrocarbon ring.

[0595] After adding compound A6 (1 equivalent) and potassium carbonate (2.5 equivalents) to N-methylpyrrolidone (NMP, excess), the mixture was stirred for 3 hours under heating at 180°C. After determining that the reaction was terminated, the resulting product was cooled to room temperature, water (excessive, twice the amount of the solvent input) was added thereto, and the resulting mixture was filtered, and the filtered solid was washed with water. Thereafter, the washed solid was recrystallized with ethyl acetate and ethanol to prepare chemical formula A7 (A7-1 to A7-8).

[0596] A7-1 to A7-8 in [Table A7] were synthesized in the same manner as in the method for synthesizing Chemical Formula A7, except that A6 was changed.

[0597] [Table A7]

[0598]

[0599]

[0600] 1-8) Synthesis of Chemical Formula A8

[0601]

[0602] Here, ring A is a monocyclic or polycyclic hydrocarbon ring.

[0603] Compound A7 (1 equivalent) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (SM3, 1.3 equivalents) were placed in 1,4-dioxaborolane. 1,4-dioxane (12 times the mass ratio of A7), potassium acetate (KOAc, 3 equivalents) was added thereto, and the resulting mixture was stirred and refluxed. Bis(diphenylphosphino)ferrocenedichloropalladium (Pd(dppf)2Cl2, 0.05 equivalents) was added to 1,4-dioxane. The mixture was stirred in alkane for 5 minutes, then added thereto, and after 2 hours, the reaction was determined to be terminated, and then the resulting product was cooled to room temperature. After ethanol and water were added thereto, the resulting mixture was filtered and purified by recrystallization with ethyl acetate and ethanol to prepare Chemical Formula A8 (A8-1 to A8-8).

[0604] A8-1 to A8-8 in [Table A8] were synthesized in the same manner as in the method for synthesizing Chemical Formula A8, except that A7 was changed.

[0605] [Table A8]

[0606]

[0607]

[0608] 1-9) Synthesis of Int.

[0609]

[0610] Here, L1, Ar1, x, y, and m are the same as those in Chemical Formula 1, Z1 and Z2 are each a halogen group, and Z3 is a leaving group.

[0611] After SM4 (1 equivalent) and Ar1-Z3 (the amount of Z1, depending on y, i.e., 1.1 equivalents or 2.1 equivalents) are added to tetrahydrofuran (THF, excess), a 2M potassium carbonate aqueous solution (30 volume ratio compared to THF) is added thereto, tetrakistriphenylphosphine palladium (2 mol%) is added thereto, and then the resulting mixture is stirred for 10 hours under heating at 85° C. After the temperature is lowered to room temperature and the reaction is terminated, the layers are separated by removing the potassium carbonate aqueous solution, and the residue is column-filtered with hexane and ethyl acetate to prepare chemical formula int. (int.1 to int.12).

[0612] int.1 to int.12 in [Table int.] were synthesized in the same manner as in the method of synthesizing the chemical formula int., except that SM4 and Ar1-Z3 were changed.

[0613] [table int.]

[0614]

[0615]

[0616] 1-10) Synthesis of Chemical Formula 1

[0617] Here, R1 to R8, L1, Ar1, x, y, and m are the same as those in Chemical Formula 1, and Z2 is a halogen group.

[0618] After Int. (1 equivalent) and A8 (1.1 equivalents or 1.1 equivalents per halogen number) were added to tetrahydrofuran (excess), 2M potassium carbonate aqueous solution (30 volume ratio compared to THF) was added thereto, and tetrakistriphenylphosphine palladium (2 mol%) was added thereto, and the resulting mixture was stirred for 10 hours under heating at 85° C. After the temperature was lowered to room temperature and the reaction was terminated, the layers were separated by removing the potassium carbonate aqueous solution, and the residue was columned with hexane and ethyl acetate to prepare the product of Chemical Formula 1 (Compounds 1 to 13).

[0619] Compounds 1-1 to 1-13 in [Table 1H] were synthesized in the same manner as in the method for synthesizing Chemical Formula 1, except that int. and A8 in [Table 1H] were changed.

[0620] [Table 1H]

[0621]

[0622]

[0623]

[0624] 1-11) Synthesis of Chemical Formula 1D

[0625]

[0626] Here, R1 to R8, L1, Ar1, x, y, and m are the same as those in Chemical Formula 1, and Dz is the number of deuterium substitution.

[0627] Chemical formula 1 (1 equivalent) and trifluoromethanesulfonic acid (catalyst) are placed in C6D6 (10 to 50 times the mass ratio compared to the reactant), and the resulting mixture is stirred at 70 ° C for 10 to 100 minutes. After the reaction is completed, D2O (excess) is added thereto, the resulting solution is stirred for 30 minutes, and then trimethylamine (excess) is added dropwise thereto. The reaction solution is transferred to a separatory funnel and extracted with water and chloroform. The extract is dried over MgSO4 and then recrystallized by heating with toluene to obtain compound 1D (compounds 1-14 to 1-17) of Table 1D below.

[0628] [Table 1D]

[0629]

[0630] Each product has a different degree of deuterium substitution depending on the reaction time, and the substitution rate is determined based on the maximum m / z (M+) value.

[0631] The product compounds 1-14 to 1-17 were synthesized with reference to existing internal literature such as KR 1790854 B1.

[0632] [Preparation Example 2] Synthesis of Formula 2

[0633] 1) Synthesis of Chemical Formula 2 based on aromatic groups

[0634]

[0635] Here, Ar3 is a substituted or unsubstituted aryl group.

[0636] Reactant (1 equivalent) and trifluoromethanesulfonic acid (TfOH, catalyst) are put into C6D6 (10 times to 50 times mass ratio compared with reactant), and the resulting mixture is stirred at 70 ℃ for 10 minutes to 100 minutes.After the reaction is completed, D2O (excessive) is added thereto, the resulting solution is stirred for 30 minutes, and then trimethylamine (excessive) is added thereto.The reaction solution is transferred to a separating funnel, and extracted with water and chloroform.The extract is dried through MgSO4, and then recrystallized by heating with toluene, to obtain the product of [Table 2-1] below.

[0637] [Table 2-1]

[0638]

[0639]

[0640]

[0641]

[0642] Each product has a different degree of deuterium substitution depending on the reaction time, and the substitution rate is determined based on the maximum m / z (M+) value.

[0643] Compounds A to W as reactants are synthesized with reference to existing documents such as JP 4070676 B2, KR 1477844B1, US6465115 B2, JP 3148176 B2, JP 4025136 B2, JP 4188082B2, JP 5015459 B2, KR 1979037B1, KR 1550351 B1, KR 1503766 B1, KR 0826364B1, KR 0749631B1 and KR 1115255B1. In addition, for compounds 1-A to 1-W as deuterium-substituted products, reference is made to existing document KR 1538534 B1.

[0644] 2) Synthesis of Furan-based Chemical Formula 2

[0645]

[0646] Reactant (1 equivalent) and trifluoromethanesulfonic acid (catalyst) are put into C6D6 (10 times to 50 times mass ratio compared with reactant), and the resulting mixture is stirred at 70 ℃ for 10 minutes to 100 minutes. After the reaction is completed, D2O (excessive) is added thereto, the resulting solution is stirred for 30 minutes, and then trimethylamine (excessive) is added thereto. The reaction solution is transferred to a separating funnel, and extracted with water and chloroform. The extract is dried through MgSO4, and then recrystallized by heating with toluene, to obtain the product of [Table 2-2] to [Table 2-3] below.

[0647] [Table 2-2]

[0648]

[0649]

[0650]

[0651]

[0652]

[0653] Each product has a different degree of deuterium substitution depending on the reaction time, and the substitution rate is determined based on the maximum m / z (M+) value.

[0654] Compounds 1# to 27# as reactants were synthesized with reference to existing documents such as KR 1964435 B1, KR 1899728 B1, KR 1975945 B1, KR 2018-0098122 A, KR 2018-0102937 A, and KR 2018-0103352 A. In addition, for compounds 2-1 to 2-27 as deuterium substitution products, reference was made to existing document KR 1538534 B1.

[0655] [Table 2-3]

[0656]

[0657]

[0658]

[0659]

[0660] Each product has a different degree of deuterium substitution depending on the reaction time, and the substitution rate is determined based on the maximum m / z (M+) value.

[0661] Compounds 28# to 47# as reactants were synthesized with reference to existing internal documents such as KR 1994238 B1, KR 1670193 B1, KR 1754445 B1, and KR 1368164 B1. In addition, for compounds 2-28 to 2-47 as deuterium-substituted products, reference was made to existing document KR 1538534 B1.

[0662] [Experimental Example 1] Dipole moment (DM) and sublimation temperature of Preparation Example 2

[0663] [Table 2-4]

[0664]

[0665]

[0666] In this case, the units of dipole moment (DM) are Debye and the units of sublimation temperature are °C.

[0667] The physical properties of the compounds synthesized in the preparation examples are shown in [Table 2-4]. Regarding the physical properties of compounds A to W, although compounds 1-A to 1-W have differences in chemical structure between carbon-hydrogen skeletons and carbon-deuterium skeletons, the basic chemical skeletons are the same, and the differences in dipole moments are almost the same, so that the values ​​of the physical properties are collectively regarded as compounds A to W. In addition, compounds 1# to 47# are the same as compounds 2-1 to 2-47, and their values ​​are collectively regarded as compounds 1# to 47#.

[0668] In the compound synthesized in Preparation Example 2, the compound (main body 1) of the chemical formula 2 based on aryl and the compound (main body 2) of the chemical formula 2 based on furan are prepared to have a difference in dipole moment in their chemical structures. Compounds A to W corresponding to the chemical formula 2 based on aryl have a skeleton based only on carbon and hydrogen due to having an aryl-based substituent, and the division of the chemical structure with fewer electrons and more electrons is limited, thereby showing a result that the dipole moment (DM) does not exceed a maximum of 0.3 Debye. In contrast, it can be determined that compounds 1# to 47# of the chemical formula 2 based on furan have a relatively higher dipole moment (DM) than compounds A to W based on the chemical formula due to the substitution of anthracene skeletons with furan containing heteroaryl or aryl groups containing relatively electron-rich oxygen, thereby having the potential to deepen the electronic division in the chemical structure with a carbon-hydrogen skeleton. Therefore, the combination of the two structures proposed in this document has a range in which the DM difference between the two main bodies exceeds at least 0.2.

[0669] |DM 主体1 -DM 主体2 |>0.2

[0670] Furthermore, it was confirmed that the sublimation temperature of the compound synthesized in the preparation example was lower than 400° C., and when the sublimation temperature of the compound was 400° C. or higher, the compound had many limitations when used as a material for an organic electroluminescent device.

[0671] Furthermore, in order to pre-sublimate and prepare a mixture of one of the aryl-based compounds of Chemical Formula 2 and one of the furan-based compounds of Chemical Formula 2, the following formula is preferably satisfied.

[0672] |T 升华1 -T 升华2 |≤20℃

[0673] [Experimental Example 2] Preparation of a mixture

[0674] The premixability of two compounds (one each of Chemical Formula 2 and Chemical Formula 3) corresponding to the two entities to be mixed was tested by high pressure liquid chromatography (HPLC) analysis of the evaporated film. In the preparation example of this mixture, Compound J (Chemical Formula 2) and Compound 6# (Chemical Formula 3) were used.

[0675] For this purpose, 0.15 g of compound J (or compound 1-J) and 0.15 g of compound 6# (or compound 2-6) were mixed in a ratio of 1:1 and crushed. 0.3 g of the mixture was placed in the evaporation source of the VTE vacuum chamber. The pressure was reduced to 10 by evacuating the chamber. -7 Support pressure. The premixed components are deposited on a glass substrate at a rate of After the thick film was formed, the substrate was replaced twice more continuously without interrupting the deposition process to avoid cooling of the feedstock and to keep the feedstock at a suitable temperature. The deposited film was analyzed by HPLC and the results are shown below Figure 5 The three substrate samples were taken and labeled as Film 1 to Film 3 as described below. From Film 1 to Film 3, the composition of Compound J (Chemical Formula 2) and Compound 6# (Chemical Formula 3) did not change significantly. The concentration variation before and after deposition within 10%, preferably within 5%, throughout the process is considered to be excellent and useful for commercial OLED applications, and it seems that the above concentration variation can be maintained when the difference in sublimation temperature between the two mixed compounds is 20°C or less. The difference in sublimation temperature between Compound J and Compound 6# is 10°C.

[0676] As shown below, the slight change in concentration does not show any trend in the device, and the sample collection and HPLC analysis can be described by the following formula 2. More specifically, the first compound (Compound J) or the second compound (Compound 6#) has a concentration C1 in the mixture, and the concentration of C1 is 1×10-4 Torr to 1×10 -9 The mixture was heated to 1000 rpm at a chamber base pressure of 1000 torr. to The deposition rate of evaporation has a concentration C2 in a film formed on a surface located at a certain distance from a point where the mixture is evaporated in a high vacuum evaporation system, and satisfies the following formula.

[0677] |(C1-C2) / C1|<10%

[0678] For the compound represented by compound 6#, when the concentration C1 in the composition is 48.85%, the concentration change is 2.3% because the concentration of film 1 is 47.69%, the concentration change is 3.9% because the concentration of film 2 is 47.69%, and the concentration change is 2.3% because the concentration of film 3 is 47.69%.

[0679] The concentration variation did not vary significantly in the produced Films 1 to 3, and it was observed that the deviation between the films was small. Therefore, the above conditions are desirable.

[0680] [Experimental Example 3] Comparative Preparation Example of Mixture

[0681] The following exemplifies the results of mixtures other than the conditions presented in this specification. In the following comparative preparation examples of mixtures, Compound B (Chemical Formula 2) and Compound 24# (Chemical Formula 3) were used.

[0682] For mixing, 0.21 g of compound B (or compound 1-B) and 0.09 g of compound 24# (or compound 2-24) were mixed at a ratio of 7:3 and pulverized. The manufacturing conditions were the same as those of the preparation example of the mixture in Preparation Example 3, and the results are shown below. Figure 6 middle.

[0683] Based on the above formula 2, for the compound represented by compound B, when the concentration C1 in the composition is 69.30%, the concentration change is 5.5% because the concentration of film 1 is 65.42%, the concentration change is 11.6% because the concentration of film 2 is 61.22%, and the concentration change is 9.3% because the concentration of film 3 is 62.82%.

[0684] The concentration variation varied significantly in the produced films 1 to 3, and in particular, a variation of 10% or more was observed, and a large deviation between the films was observed. Therefore, the above conditions are undesirable.

[0685] [Experimental Example 4] Fabrication of OLED

[0686] <Example 1>

[0687] As the positive electrode, a layer with a thickness of The substrate of ITO / Ag / ITO was cut into a size of 50mm×50mm×0.5mm, placed in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. A product manufactured by Fischer Co. was used as a detergent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic washing was performed using isopropyl alcohol, acetone, and methanol solvents in sequence, and then dried.

[0688] On the positive electrode thus prepared, HI-1 was thermally vacuum deposited to a thickness of Thus, a hole injection layer is formed, and HT1 as a hole transport material is vacuum deposited on the hole injection layer to a thickness of Then, the hole transport layer is formed using EB1. Next, the main compound 1-1 synthesized in Preparation Example 1 and the dopant BD1 (2 wt%) were vacuum deposited onto The thickness of the first light-emitting layer is formed, and then the host compound A of Preparation Example 2 and the dopant BD1 (2 wt %) are vacuum deposited onto the Then, HB1 is deposited to a thickness of Thus, an electron regulating layer is formed, and the compound ET1 and Liq are mixed at a mass ratio of 5:5 to form a layer having a thickness of Subsequently, magnesium and lithium fluoride (LiF) were deposited to a thickness of To form an electron injection layer<electron injection layer,EIL> A film of magnesium and silver (1:4) is used to form a thickness of The negative electrode is then deposited with CP1 to a thickness of In the above steps, the deposition rate of the organic materials is maintained at

[0689]

[0690] <Comparative Examples 1 to 8 and Examples 2 to 86>

[0691] Devices were manufactured in the same manner as in Example 1, except that in Comparative Examples 1 to 8 and Examples 2 to 86, materials shown in the following [Table 1] were used as materials for the light emitting layer.

[0692] For the devices fabricated in Comparative Examples 1 to 8 and Examples 1 to 86, at 20 mA / cm 2 The driving voltage, luminous efficiency and time to reach a value of 95% compared to the initial luminance (LT95) were measured at a current density of . The results are shown in the following [Table 1].

[0693] [Table 1]

[0694]

[0695]

[0696]

[0697]

[0698]

[0699]

[0700]

[0701] The results in [Table 1] show a case where the device has a structure in which the light-emitting layer is formed of two layers, the main body of the first light-emitting layer and the main body of the second light-emitting layer are single main bodies of each layer, and the compound of Chemical Formula 1 is composed of the main body of the first light-emitting layer. Comparative Examples 1 to 4 are cases in which an aryl-based anthracene main body is used as the main body of the second light-emitting layer, and exhibit lower efficiency and service life than Examples 1 to 86, and particularly significantly higher voltage. Among them, Comparative Examples 2 and Comparative Examples 3 have a structure in which the main body of the second light-emitting layer contains deuterium, and it can be seen that, although there is an effect of improving the service life of some parts, the effect on the overall device performance (which is significantly lower than the effect of the embodiment) is not significant. In addition, when Comparative Example 2 is compared with Comparative Example 4 in which BD2 (which is a boron-based blue dopant) is also applied, the trend is maintained.

[0702] Comparative Examples 5 to 8 are cases where a furan-based anthracene main body is used as the main body of the second light-emitting layer, and also exhibit particularly low voltages compared to Comparative Examples 1 to 4, but also exhibit low efficiency and service life and high voltages compared to Examples 1 to 86. Among them, Comparative Example 7 has a structure in which the main body of the second light-emitting layer contains deuterium as in Comparative Examples 2 and 3, and it can be seen that, although there is an effect of improving the service life of some parts, the effect on the overall device performance (which is significantly lower than the effect of the embodiment) is not significant. In addition, when Comparative Example 7 is compared with Comparative Example 8 in which BD2 (which is a boron-based blue dopant) is also applied, the trend is also maintained.

[0703] In Examples 1 to 86 of the present application, it can be seen that when the compound corresponding to Chemical Formula 1 is applied as the host in the first light-emitting layer to play the role of injecting holes and acting as an electron barrier, changing the light-emitting area in the light-emitting layer, and maintaining low voltage characteristics and efficiency, the performance of the device is ensured, which is considered to be important in a blue light-emitting device using an anthracene host as the host of the second light-emitting layer in which the existing aromatic-based or furan-based material is replaced.

[0704] Examples 1 to 23 are cases where the compound of Chemical Formula 1 is used as the host of the first light-emitting layer and an aryl-based anthracene host is used as the host of the second light-emitting layer, and the examples are evaluated as cases where the H compound not applying deuterium is introduced as the host of the second light-emitting layer (Examples 1, 5, 8, 12, 16, and 21) and cases where the D compound applying deuterium is introduced as the host of the second light-emitting layer (the rest), and the examples are intended to determine the effect of the light-emitting layer having two layers in each case. The inventors have seen data in which the service life can be further improved by deuterium substitution of the host of the second light-emitting layer, and can also be positively determined that when the compound of Chemical Formula 1 is used as the host of the first light-emitting layer, the device performance is improved.

[0705] Therefore, in Examples 24 to 27, the compound of Chemical Formula 1 was substituted with deuterium and used as a host of the first light-emitting layer to compare device results, as compared with Examples 10, 13, 14, and 3. In the case where the first light-emitting layer was formed adjacent to the hole regulating layer, it was observed that the lifetime was further improved by deuterium substitution.

[0706] In Examples 28 to 31, the trends and performance of the devices were determined by changing only BD1 as a blue dopant to BD2 in the devices of Examples 24 to 27, and when the boron-based dopant BD2 was used, a trend of maintaining improved service life while improving additional efficiency was determined.

[0707] Unlike Examples 1 to 23, Examples 32 to 58 are cases in which anthracene derivatives bonded with various heteroaryl groups such as dibenzofuran, naphthiobenzofuran and triphenyldifuran are introduced as the main body of the second light-emitting layer, and compared with Examples 1 to 23, they exhibit characteristics of relatively low voltage and low service life, but in the structure of the device manufactured by applying the compound of Chemical Formula 1 as the main body of the first light-emitting layer, it can be determined that the device is improved while maintaining the characteristics as in Examples 1 to 23.

[0708] In Examples 79 to 86, changes were introduced as in Examples 24 to 31, and the results also verified excellent device performance.

[0709] <Example 87> Production of OLED

[0710] As the positive electrode, a layer with a thickness of The substrate of ITO / Ag / ITO was cut into a size of 50mm×50mm×0.5mm, placed in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. A product manufactured by Fischer Co. was used as a detergent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic washing was performed using isopropyl alcohol, acetone, and methanol solvents in sequence, and then dried.

[0711] On the positive electrode thus prepared, HI-1 was thermally vacuum deposited to a thickness of Thus, a hole injection layer is formed, and HT1 as a hole transport material is vacuum deposited on the hole injection layer to a thickness of Then, the hole transport layer is formed using EB1. Next, the main compound 1-12 synthesized in Preparation Example 1 and the dopant BD1 (2 wt%) were vacuum deposited onto The thickness of the first light-emitting layer is formed, and then the host compound B of Preparation Example 2, the compound 2-3 of Preparation Example 2 and the dopant BD1 (2 wt %) are vacuum deposited onto the Then, HB1 is deposited to a thickness of Thus, an electron regulating layer is formed, and the compound ET1 and Liq are mixed at a mass ratio of 5:5 to form a layer having a thickness of Subsequently, magnesium and lithium fluoride (LiF) were deposited to a thickness of To form an electron injection layer <eil>A film of magnesium and silver (1:4) is used to form a thickness of The negative electrode is then deposited with CP1 to a thickness of In the above steps, the deposition rate of the organic materials is maintained at

[0712]

[0713] [Comparative Examples 9 to 18 and Examples 88 to 122]

[0714] Devices were manufactured in the same manner as in Example 87, except that in Comparative Examples 9 to 18 and Examples 88 to 122, materials shown in Table 2 below were used as materials for the light-emitting layer.

[0715] However, as shown in [Table 2], the host of the second light-emitting layer represents both an example in which the light-emitting layer is formed by co-depositing two hosts by another evaporation source during the manufacture of the device and an example in which two host compounds are used for a premix prepared in advance.

[0716] In particular, the conditions for preparing the premix using the host of the second light-emitting layer have been mentioned above, and [Table 3] shows that two hosts of the second light-emitting layer applied to Comparative Examples 9 to 18 and Examples 87 to 122 in [Table 2] can be used to prepare the premix. For the devices manufactured in Comparative Examples 9 to 18 and Examples 87 to 122, at 20 mA / cm 2 The driving voltage, luminous efficiency and time to reach a value of 95% compared to the initial luminance (LT95) were measured at a current density of . The results are shown in the following [Table 2].

[0717] [Table 2]

[0718]

[0719]

[0720]

[0721]

[0722]

[0723] [Table 3]

[0724]

[0725]

[0726] The results in [Table 2] show a case where the light-emitting layer is formed of two layers, the main body of the first light-emitting layer is a single main body and is a compound of Chemical Formula 1, and the main body of the second light-emitting layer is a mixed main body and is composed of a mixed main body of two types of anthracenes co-deposited or pre-mixed. Comparative Examples 9 and 10 are examples in which, among widely used aryl-based anthracene compounds, H compounds (in which only hydrogen skeletons are substituted) and D compounds (in which deuterium is partially or completely substituted) are co-deposited or a premixture is prepared and deposited to form the main body of the second light-emitting layer. In addition, Comparative Examples 11, 12, and 13 are examples in which an aryl-based anthracene compound and two types of heteroaryl-based anthracene compounds (one or more of the two types are D compounds) are co-deposited or a premixture is prepared and deposited to form the main body of the second light-emitting layer. Comparative Examples 14, 15, and 16 are examples in which two types of heteroaryl-based anthracene compounds (one or more of the two types are D compounds) are co-deposited or a premixture is prepared and deposited to form the main body of the second light-emitting layer.

[0727] It can be seen that the use of a mixed host to form the light-emitting layer improves the performance of the device when compared with the case of a single host in Comparative Examples 1 to 8 in [Table 1] above. In addition, in Comparative Examples 17 and 18, it can be confirmed that even when a boron-based blue dopant is applied and a mixed host (co-deposited or prepared premix) is used as in Comparative Example 4 in [Table 1], the characteristics are maintained and the improvement in device performance is maintained.

[0728] It can be observed that, compared with Comparative Examples 9 to 18, by using the compound of Chemical Formula 1 as the main body of the first light-emitting layer and co-depositing various combinations of anthracene compounds (aryl-based compounds or heteroaryl-based compounds, one of which is a deuterium-substituted D compound) (1:1 mass ratio) to form the main body of the second light-emitting layer, Examples 87 to 102 exhibit very excellent voltage and efficiency characteristics, and can also increase the service life.

[0729] Unlike the host of the second light-emitting layer in Examples 87 to 102, in Examples 103 to 106, devices were manufactured by co-depositing two hosts with deuterium-substituted D compounds, and an additional lifetime increase of 20% on average was shown compared to Examples 97, 101, 92, and 93. Unlike Examples 103 to 106, in Examples 107 to 110, among the claimed compounds in the first light-emitting layer, compounds 1-14 to 1-17, which are deuterated forms of compounds 1-7, 1-10, 1-11, and 1-12, were used to construct devices. In this regard, in addition, in the case where the first light-emitting layer is formed adjacent to the hole regulating layer as mentioned in the results of [Table 1], it can be observed that the lifetime is additionally improved by deuterium substitution.

[0730] Examples 111 to 114 are devices manufactured by changing the method of co-depositing the host of the second light-emitting layer of Examples 107 to 110 to a method in which a premix of two types of hosts is formed and then evaporated from a single deposition source. The conditions for forming the premix are carried out with reference to the above description, and due to the uniform mixing effect of the molecular units, the device performance of the co-deposited device is maintained or stably improved.

[0731] Examples 115 to 118 are cases where BD2 (boron-based blue dopant) is applied to one or all of the dual light-emitting layers and a premixed host is applied. It can be seen that the advantages of the premixed host are maintained while maintaining high efficiency compared to the pyrene dopant.

[0732] Examples 119 to 122 are cases in which a premix of the second light-emitting layer in Examples 115 to 118 is prepared by changing the ratio of the two compounds and deposited to form a host, and it is shown that the advantages and disadvantages of the two compounds can be applied by the ratio and reflected in the device.< / eil>

Claims

1. A compound of the following chemical formula 1: [Chemical formula 1] in, In Chemical Formula 1, X1 is O or S, L1 is a single bond; substituted or unsubstituted phenylene; substituted or unsubstituted biphenylene; substituted or unsubstituted terphenylene; substituted or unsubstituted quaterphenylene; substituted or unsubstituted fluorenylene; substituted or unsubstituted spirocyclopentanefluorenylene; substituted or unsubstituted spirobifluorenylene; substituted or unsubstituted naphthylene; substituted or unsubstituted phenanthrenylene; substituted or unsubstituted trimphenylene; substituted or unsubstituted substituted or unsubstituted phenanthrofuranyl; substituted or unsubstituted phenanthrothienyl; substituted or unsubstituted benzofuranyl; substituted or unsubstituted benzothiophenylene; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted dibenzothiophenylene; substituted or unsubstituted benzonaphthofuranyl; substituted or unsubstituted benzonaphthothiophenylene; substituted or unsubstituted carbazolylene; or substituted or unsubstituted benzocarbazolylene, Any one of R1 to R8 is bonded to L1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; aryl which is unsubstituted or substituted with deuterium, alkyl, cycloalkyl or heterocyclic group having O or S; or substituted or unsubstituted heterocyclic group having O or S, and is optionally fused with an adjacent group to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted heterocyclic ring, Ar1 is a pyrenyl group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group and a heteroaryl group; a fluoranthenyl group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group and a heteroaryl group; or a phenanthrenyl group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group and a heteroaryl group, m is an integer from 0 to 3, and when m is 2 or more, L1 in the brackets are the same as or different from each other, x is 1 or 2, and when x is 2, the structures in the brackets are the same as or different from each other, and y is an integer of 1 or 2, and when y is 2, Ar1 in the brackets are the same as or different from each other.

2. The compound according to claim 1, wherein L1 is a single bond; a phenylene group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a biphenylene group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a terphenylene group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a quaterphenylene group which is unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; substituted with at least one of deuterium, alkyl, cycloalkyl, aryl and heteroaryl; spirocyclopentanefluorenyl unsubstituted or substituted with at least one selected from deuterium, alkyl, cycloalkyl, aryl and heteroaryl; spirobifluorenyl unsubstituted or substituted with at least one selected from deuterium, alkyl, cycloalkyl, aryl and heteroaryl; naphthylene unsubstituted or substituted with at least one selected from deuterium, alkyl, cycloalkyl, aryl and heteroaryl; phenanthrenyl unsubstituted or substituted with at least one selected from deuterium, alkyl, cycloalkyl, aryl and heteroaryl; triphenylene unsubstituted or substituted with at least one selected from deuterium, alkyl, cycloalkyl, aryl and heteroaryl. ; phenanthrofuranyl unsubstituted or substituted with at least one selected from deuterium, alkyl, cycloalkyl, aryl and heteroaryl; phenanthrothienyl unsubstituted or substituted with at least one selected from deuterium, alkyl, cycloalkyl, aryl and heteroaryl; benzofuranyl unsubstituted or substituted with at least one selected from deuterium, alkyl, cycloalkyl, aryl and heteroaryl; benzothienyl unsubstituted or substituted with at least one selected from deuterium, alkyl, cycloalkyl, aryl and heteroaryl; dibenzofuranyl unsubstituted or substituted with at least one selected from deuterium, alkyl, cycloalkyl, aryl and heteroaryl; a dibenzothiophenylene group substituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a benzonaphthofuranyl group unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a benzonaphthothiophenylene group unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a carbazolylene group unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; or a benzocarbazolylene group unsubstituted or substituted with at least one selected from deuterium, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group.

3. The compound according to claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 1-A to 1-F: [Chemical Formula 1-A] [Chemical Formula 1-B] [Chemical Formula 1-C] [Chemical formula 1-D] [Chemical Formula 1-E] [Chemical Formula 1-F] In Chemical Formulae 1-A to 1-F, X1, L1, m, R1 to R8, and Ar1 are the same as defined in Chemical Formula 1.

4. The compound according to claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 1-a to 1-e: [Chemical formula 1-a] [Chemical formula 1-b] [Chemical formula 1-c] [Chemical formula 1-d] [Chemical formula 1-e] In Chemical Formulae 1-a to 1-e, X1 and Ar1 are the same as defined in Chemical Formula 1, and Any one of R1 to R8 is bonded to Ar1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; aryl which is unsubstituted or substituted with deuterium, alkyl, cycloalkyl or a heterocyclic group having O or S; or a substituted or unsubstituted heterocyclic group having O or S, and is optionally fused with an adjacent group to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted heterocyclic ring.

5. The compound according to claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-3: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] In Chemical Formula 1-1 to Chemical Formula 1-3, R1 to R8, X1, L1, x, m and y are the same as those defined in claim 1, and Any one of R101 to R110 is bonded to L1, and the rest are the same as or different from each other and are each independently hydrogen, deuterium, an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group, or the rest are fused with an adjacent group to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted heterocycle.

6. The compound according to claim 1, wherein Chemical Formula 1 is any one of the following structures:

7. An organic light-emitting device, comprising: anode; cathode; as well as an organic material layer having one or more layers disposed between the anode and the cathode, wherein one or more of the organic material layers comprises the compound of Chemical Formula 1 according to any one of claims 1 to 6.

8. The organic light emitting device according to claim 7, wherein the organic material layer comprises a light emitting layer disposed between the anode and the cathode, The light-emitting layer comprises: a first light-emitting layer disposed between the anode and the cathode; and a second light-emitting layer disposed between the first light-emitting layer and the cathode and in contact with the first light-emitting layer, and The first light emitting layer includes the compound of Chemical Formula 1.

9. The organic light-emitting device according to claim 8, wherein the second light-emitting layer comprises at least one compound of the following Chemical Formula 2 and the following Chemical Formula 3: [Chemical formula 2] In chemical formula 2, One or more of R11 to R20 are bonded to the * part of the following chemical formula 2-1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group, [Chemical formula 2-1] In chemical formula 2-1, L2 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, Ar2 is a substituted or unsubstituted aryl group, and p is an integer from 1 to 3, [Chemical formula 3] In chemical formula 3, One or more of Y1 to Y10 are bonded to the * part of the following chemical formula 3-1, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group, [Chemical formula 3-1] In chemical formula 3-1, A and B are the same as or different from each other and are each independently a substituted or unsubstituted aromatic hydrocarbon ring; or a substituted or unsubstituted aromatic heterocycle, L3 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and q is an integer from 1 to 3.

10. The organic light emitting device according to claim 9, wherein for the light emitting layer, the first light emitting layer comprises the compound of Chemical Formula 1 as a first host material, and The second light emitting layer includes at least one of the compound of Chemical Formula 2 and the compound of Chemical Formula 3 as a second host material. 11 . The organic light emitting device according to claim 8 , wherein the first light emitting layer and the second light emitting layer each further comprise a dopant material. 12 . The organic light emitting device according to claim 11 , wherein the dopant material is a fluorescent dopant. 13 . The organic light emitting device according to claim 12 , wherein the fluorescent dopant is a pyrene-based compound or a non-pyrene-based compound. 14 . The organic light emitting device according to claim 13 , wherein the non-pyrene-based compound is an arylamine-based compound or a boron-based compound.

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