Compounds and organic light emitting devices comprising the same

Abstract

This specification relates to compounds and organic light emitting devices comprising the same.

Description

Technical Field

[0001] This specification claims priority to Korean Patent Application No. 10-2021-0089233, filed with the Korean Intellectual Property Office on July 7, 2021, the entire contents of which are contained herein.

[0002] This specification relates to compounds and organic light-emitting devices containing them. Background Technology

[0003] Organic light emission (OLED) typically refers to the phenomenon of converting electrical energy into light energy using organic materials. OLED devices generally have a structure including a first electrode, a second electrode, and an organic layer between them. To improve the efficiency and stability of OLEDs, the organic layer is often formed by a multilayer structure composed of different materials; for example, it can consist of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such an OLED structure, if a voltage is applied between the two electrodes, holes are injected into the organic layer from the first electrode, and electrons are injected from the second electrode. When the injected holes and electrons meet, they form excitons. When these excitons re-enter the ground state, they emit light.

[0004] There is a continuous demand for the development of new materials for organic light-emitting devices as described above. Summary of the Invention

[0005] Technical issues

[0006] This specification provides compounds and organic light-emitting devices containing them.

[0007] Solution to the problem

[0008] One embodiment of this specification provides a compound of the following chemical formula 1.

[0009] [Chemical Formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] X1 is either O or S.

[0013] R1 is hydrogen; deuterium; a halogen group; cyano; nitro; hydroxyl; 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 comprising at least one selected from N, O, and S.

[0014] R2 is hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl 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 comprising at least one selected from N, O, and S, or adjacent groups that can combine to form a substituted or unsubstituted ring.

[0015] R3 is a heterocyclic group comprising a polycyclic compound selected from at least one of N, O, and S; or a heterocyclic group comprising a monocyclic compound selected from at least one of O and S, whether substituted or unsubstituted.

[0016] L1 and L2 may be the same or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group.

[0017] Ar represents substituted or unsubstituted aryl groups.

[0018] r1 is an integer from 1 to 8.

[0019] r2 is an integer from 1 to 6.

[0020] When r1 is 2 or more, R1 values ​​are either the same or different.

[0021] When r² is 2 or higher, R² values ​​are either the same or different.

[0022] For r, which is an integer from 1 to 4, when r is 2 or higher, Ar can be either the same or different from each other.

[0023] Another embodiment of this specification provides an organic light-emitting device, characterized in that it includes: a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers contain the aforementioned compound.

[0024] Invention Effects

[0025] Organic light-emitting devices using compounds according to one embodiment of this specification can achieve lower driving voltage, higher luminous efficiency, or longer lifetime. Attached Figure Description

[0026] Figure 1 The diagram illustrates the structure of an organic light-emitting device according to one embodiment.

[0027] Figure 2 The diagram illustrates the structure of an organic light-emitting device according to another embodiment.

[0028] Explanation of symbols

[0029] 1: Substrate

[0030] 2: First electrode

[0031] 2-1: Anode

[0032] 3: Organic layer

[0033] 4: Second electrode

[0034] 4-1: Cathode

[0035] 5: First organic layer

[0036] 6: Emissive layer

[0037] 7: Second organic layer

[0038] 8: Hole injection layer

[0039] 9: Hole transport layer

[0040] 10: Hole regulation layer

[0041] 11: Electronic Regulation Layer

[0042] 12: Electron transport layer

[0043] 13: Electron Injection Layer

[0044] 14: Overlay. Detailed Implementation

[0045] The following is a detailed description of this instruction manual.

[0046] This specification provides for compounds represented by the above chemical formula 1.

[0047] The compounds of Formula 1 in this specification are anthracene blue fluorescent host incorporating aryl groups including fluorene, along with fused dibenzofuran or even dibenzothiophene. By setting substituents at specific positions, improved hole and electron injection, transport, and modulation properties can be achieved. Specifically, the compounds of Formula 1 in this specification, through specific directional bonding of dibenzofuran or dibenzothiophene and the introduction of heteroaryl groups as substituents into the aforementioned unit, modulate the migration and balance of holes and electrons, resulting in the fabrication of superior devices.

[0048] In this specification, when a part is indicated to "include / contain" a certain component, unless otherwise stated, it means that other components may be included, rather than excluding other components.

[0049] In this specification, when it is stated that a component is located "on" another component, it includes not only the case where one component is connected to another component, but also the case where there are other components between the two components.

[0050] In this specification, * or dashed lines indicate sites of binding or fusion with other substituents or binding sites.

[0051] In this specification, Cn represents the number of carbon atoms n, and Cn-Cm represents the number of carbon atoms n to m. In this specification, the term "layer" is used interchangeably with "film" primarily used in this technical field, referring to a coating covering a target area. The size of the aforementioned "layer" is not limited; the sizes of each "layer" can be the same or different. According to one embodiment, the size of a "layer" can be equal to the size of the entire device, can be equivalent to the size of a specific functional area, or can be as small as a single sub-pixel.

[0052] In this specification, the inclusion of a specific substance A in layer B means including both i) the case where one or more substances A are included in a single layer of layer B, and ii) the case where layer B consists of one or more layers and substances A are included in one or more layers of multiple layers of layer B.

[0053] In this specification, the inclusion of a specific substance A in layer C or layer D means that i) it is included in more than one layer of layer C, or ii) it is included in more than one layer of layer D, or iii) it is included in both more than one layer of layer C and more than one layer of layer D.

[0054] Examples of substituents in this specification are described below, but are not limited thereto.

[0055] The term "substitution" refers to the replacement of hydrogen atoms on carbon atoms in a compound with other substituents. There is no limitation on the position of substitution, as long as the hydrogen atom can be substituted, that is, the position where the substituent can be substituted. When more than two substituents are substituted, the two or more substituents can be the same or different from each other.

[0056] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from the group consisting of deuterium, halogen groups, cyano (-CN), silyl, boron, alkyl, cycloalkyl, aryl, and heterocyclic groups, or substituted by a substituent formed by two or more substituents linked together as exemplified above, or without any substituents. For example, "a substituent formed by two or more substituents linked together" can be biphenyl. That is, biphenyl can be aryl, or it can be interpreted as a substituent formed by two phenyl groups linked together.

[0057] In one embodiment of this specification, "substituted or unsubstituted" means substituted by one or more substituents selected from the group consisting of deuterium, halogen groups, cyano (-CN), silyl, C1-C20 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, and C2-C60 heterocyclic groups, or substituted by a substituent formed by connecting two or more groups selected from the above group, or having no substituents.

[0058] In one embodiment of this specification, "substituted or unsubstituted" means substituted by one or more substituents selected from the group consisting of deuterium, halogen groups, cyano (-CN), silyl, C1-C10 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, and C2-C30 heterocyclic groups, or substituted by a substituent formed by connecting two or more groups selected from the above group, or having no substituents.

[0059] In one embodiment of this specification, "substituted or unsubstituted" means substituted by one or more substituents selected from the group consisting of deuterium, halogen groups, cyano (-CN), silyl, C1-C6 alkyl, C3-C20 cycloalkyl, C6-C20 aryl, and C2-C20 heterocyclic groups, or substituted by two or more substituents selected from the above group, or not having any substituents.

[0060] In this specification, the connection of two or more substituents means that the hydrogen of any one substituent is replaced by another substituent. For example, isopropyl and phenyl can be connected to form... or Such substituents.

[0061] In this specification, the connection of three substituents includes not only the case of (substituent 1)-(substituent 2)-(substituent 3) sequentially connected, but also the case where (substituent 2) and (substituent 3) are connected to (substituent 1). For example, two phenyl groups and an isopropyl group can be connected to form... or Such substituents. The same applies to cases where four or more substituents are connected.

[0062] In this specification, the case of "replaced by A or B" includes not only the case of being replaced by only A or only B, but also the case of being replaced by both A and B.

[0063] Examples of the substituents mentioned above are given below, but are not limited thereto.

[0064] Examples of halogen groups in this specification include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0065] In this specification, the silyl group can be composed of –SiY a Y b Y c The chemical formula of the above Y represents a Y b and Y cThese can be hydrogen, substituted or unsubstituted alkyl groups, or substituted or unsubstituted aryl groups. Specific examples of the aforementioned silyl groups include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl, but are not limited to these.

[0066] In this specification, the boron group can be represented by –BY d Y e The chemical formula of the above Y represents d and Y e These can be hydrogen, substituted or unsubstituted alkyl groups, or substituted or unsubstituted aryl groups. Specific examples of the aforementioned boron groups include dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl, and phenylboryl, but are not limited to these.

[0067] In this specification, the alkyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of alkyl groups 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 to these.

[0068] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group with 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., are used, but are not limited to these.

[0069] In this specification, the aryl group is not particularly limited, but is preferably an aryl group with 6 to 60 carbon atoms, and can be a monocyclic aryl or polycyclic aryl. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. Regarding the aforementioned aryl group, as a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, etc., but is not limited to these. As the aforementioned polycyclic aryl group, it can be naphthyl, anthraceneyl, phenanthryl, pyrene, peryl, triphenyl, thionyl, fluoreneyl, etc., but is not limited to these.

[0070] In this specification, the 9th carbon atom (C) of the fluorene group can be replaced by alkyl, aryl, etc., and two substituents can combine with each other to form a spiro structure of cyclopentane, fluorene, etc.

[0071] In this specification, the substituted aryl group may also include forms in which an aliphatic ring is fused to the aryl group. For example, tetrahydronaphthyl or dihydroindenyl in the following structures are included in the substituted aryl group. In the following structures, one of the carbon atoms of the benzene ring may be attached to other positions.

[0072]

[0073] In this specification, the above description of aryl groups applies, except that arylene is a divalent group.

[0074] In this specification, a heterocyclic group is a cyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms. The number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to another embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of the heterocyclic groups include pyridinyl, quinolinyl, thiopheneyl, dibenzothiopheneyl, furanyl, dibenzofuranyl, naphthobenzofuranyl, carbazoleyl, benzocarbazoleyl, naphthobenzothiopheneyl, dibenzosilole, naphthobenzosilole, hexahydrocarbazoleyl, dihydroacridinyl, dihydrodibenzodiazepine, and phenanthrene. Phenoxazine, phenothiazine, spiro(dibenzothiophene-dibenzosilazane), spiro(acridin-fluorene), etc., but not limited to these.

[0075]

[0076] In this specification, heteroaryl refers to aromatic compounds; otherwise, the above description of heterocyclic groups applies.

[0077] In this specification, "adjacent" groups can refer to substituents that are directly bonded to the atom substituted by the substituent, substituents that are stereomorphically closest to the substituent, or other substituents that are bonded to the atom substituted by the substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon atom in an aliphatic ring can be interpreted as "adjacent" groups. Furthermore, substituents bonded to two consecutive carbons in an aliphatic ring (a total of four) can also be interpreted as "adjacent" groups.

[0078] In this specification, "adjacent groups bonded together to form a ring" in the context of substituents means the formation of a ring containing the substituents involved in cyclization. This can include cases where an additional ring is fused onto the aforementioned ring containing the substituents involved in cyclization.

[0079] In this specification, the phrase "adjacent groups combine with each other to form a ring" in the context of substituents means that they combine with adjacent groups to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle. Specifically, it means that they combine with adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic heterocycle, or a combination thereof.

[0080] In this specification, an aromatic hydrocarbon ring refers to a planar hydrocarbon ring with fully conjugated π electrons, except that it is divalent, and the above description of aryl groups applies.

[0081] In this specification, aliphatic hydrocarbon rings refer to rings that are not aromatic. Examples of aliphatic hydrocarbon rings include cycloalkyl or cycloalkane rings, which, except that they are divalent, are subject to the above descriptions regarding cycloalkyl or cycloalkenyl groups. Furthermore, substituted aliphatic hydrocarbon rings also include aliphatic hydrocarbon rings fused with aromatic rings.

[0082] In this specification, fused rings of aromatic and aliphatic hydrocarbon rings refer to fused rings formed by the combination of an aromatic and an aliphatic hydrocarbon ring. Examples of fused rings of aromatic and aliphatic hydrocarbons include 1,2,3,4-tetrahydronaphthyl and 2,3-dihydro-1H-indenyl, but are not limited to these.

[0083] In this specification, an aromatic heterocycle refers to a planar heterocycle containing heteroatoms that are not carbon and hydrogen and whose π electrons are fully conjugated, while an aliphatic heterocycle refers to a ring containing heteroatoms that are not carbon and hydrogen and which are bonded together in a ring structure and are not aromatic.

[0084] In this specification, when adjacent groups in the substituents combine with each other to form a ring, any of the following structures can be formed.

[0085]

[0086] In the above structure,

[0087] A1 to A14 are each independently hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group.

[0088] a1 to a9 are each integers from 1 to 4.

[0089] a10 and a14 are each integers from 1 to 6.

[0090] * indicates the position that is being replaced.

[0091] According to one embodiment of this specification, A1 is hydrogen, or a substituted or unsubstituted aryl group.

[0092] According to one embodiment of this specification, A1 is hydrogen, or an aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

[0093] According to one embodiment of this specification, A1 is hydrogen, or a substituted or unsubstituted phenyl group.

[0094] According to one embodiment of the basic specification, A1 is hydrogen or phenyl.

[0095] According to one embodiment of this specification, A2 to A10 and A14 are hydrogen.

[0096] According to one embodiment of this specification, each of A11 to A13 is independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

[0097] According to one embodiment of this specification, each of A11 to A13 is independently an alkyl group having 1 to 30 carbon atoms, either substituted or unsubstituted, or an aryl group having 6 to 30 carbon atoms, either substituted or unsubstituted.

[0098] According to one embodiment of this specification, A11 and A12 are methyl groups.

[0099] According to one embodiment of this specification, A13 is either substituted or unsubstituted benzene or substituted or unsubstituted naphthalene.

[0100] In this specification, the above chemical formula 1 is any one of the following chemical formulas 1-1 to 1-3.

[0101] [Chemical Formula 1-1]

[0102]

[0103] [Chemical Formula 1-2]

[0104]

[0105] [Chemical Formulas 1-3]

[0106]

[0107] In the above chemical formulas 1-1 to 1-3,

[0108] X1, R1, R2, R3, r1, L1, L2, Ar, and r are defined the same as in chemical formula 1.

[0109] R4 and R5 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; cyano; nitro; hydroxyl; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group comprising at least one selected from N, O, and S.

[0110] r2 is an integer from 1 to 4.

[0111] r4 is an integer from 1 to 6.

[0112] r5 is an integer from 1 to 8.

[0113] When r4 is 2 or higher, R4 values ​​are either the same or different from each other.

[0114] When r5 is 2 or more, R5 values ​​are either the same or different from each other.

[0115] In this specification, chemical formula 1 is any one of chemical formulas 2 to 5.

[0116] [Chemical Formula 2]

[0117]

[0118] [Chemical Formula 3]

[0119]

[0120] [Chemical Formula 4]

[0121]

[0122] [Chemical Formula 5]

[0123]

[0124] In the above chemical formulas 2 to 5,

[0125] X1, R1, R2, r1, L1, L2, Ar, and r are defined in the same way as in chemical formula 1.

[0126] X2 is NR, O, or S.

[0127] X3 and X4 are each independently O or S.

[0128] X5 is either N or CR'.

[0129] R, R', and R7 through R9 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; cyano; nitro; hydroxyl; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group comprising at least one selected from N, O, and S.

[0130] R6 is hydrogen; deuterium; a halogen group; cyano; nitro; hydroxyl; substituted or substituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group comprising at least one selected from N, O, and S, or adjacent groups that can combine to form a substituted or unsubstituted ring.

[0131] r2 is an integer from 1 to 4.

[0132] r6 is an integer from 1 to 7.

[0133] r7 is an integer from 1 to 3.

[0134] r8 is an integer from 1 to 4.

[0135] r9 is an integer from 1 to 6.

[0136] When r6 is 2 or higher, R6 values ​​are either the same or different.

[0137] When r7 is 2 or higher, R7 values ​​are either the same or different from each other.

[0138] When r8 is 2 or higher, R8 values ​​are either the same or different from each other.

[0139] When r9 is 2 or more, R9 values ​​are either the same or different from each other.

[0140] In this specification, the above chemical formula 1 is any one of the following chemical formulas 2-1 to 2-4.

[0141] [Chemical Formula 2-1]

[0142]

[0143] [Chemical Formula 2-2]

[0144]

[0145] [Chemical Formula 2-3]

[0146]

[0147] [Chemical Formula 2-4]

[0148]

[0149] In the above chemical formulas 2-1 to 2-4,

[0150] X1, X2, R1, R2, r1, r2, L1, L2, Ar, and r are defined in the same way as in chemical formula 2.

[0151] X6 is NR, O, or S.

[0152] R and R61 to R64 may be the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; cyano; nitro; hydroxyl; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group comprising at least one selected from N, O, and S.

[0153] r61 is an integer from 1 to 7.

[0154] r62 and r63 are each integers from 1 to 9.

[0155] r64 is an integer from 1 to 11.

[0156] When r61 is 2 or higher, R61 values ​​are either the same or different.

[0157] When r62 is 2 or higher, R62 values ​​are either the same or different.

[0158] When r63 is 2 or higher, R63 values ​​are either the same or different.

[0159] When r64 is 2 or higher, R64 values ​​are either the same or different from each other.

[0160] In this specification, X1 is 0.

[0161] In this specification, X1 is S.

[0162] In this specification, R1 is hydrogen; deuterium; a halogen group; cyano; nitro; hydroxyl; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group comprising at least one selected from N, O, and S.

[0163] In this specification, R1 is hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group comprising at least one selected from N, O and S.

[0164] In this specification, R1 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl.

[0165] In this specification, R1 is hydrogen, deuterium, or a substituted or unsubstituted aryl group.

[0166] In this specification, R1 is hydrogen, deuterium, or an aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

[0167] In this specification, R1 is hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, or substituted or unsubstituted pyrene.

[0168] In this specification, R1 is hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, or substituted or unsubstituted naphthyl.

[0169] In this specification, R2, R4, and R5 may be the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; cyano; nitro; hydroxyl; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group comprising at least one selected from N, O, and S.

[0170] In this specification, R2, R4, and R5 may be the same as or different from each other, and each independently represents hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group comprising at least one selected from N, O, and S.

[0171] In this specification, R2, R4 and R5 may be the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms comprising at least one selected from N, O and S.

[0172] In this specification, R2, R4 and R5 may be the same as or different from each other, and each independently represents hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, cyclohexyl, tetrahydronaphthyl substituted or unsubstituted with alkyl, phenyl, biphenyl, terphenyl, naphthyl, furanyl or thiophene.

[0173] In this specification, when adjacent groups in R2 combine to form substituted or unsubstituted rings, substituted or unsubstituted hydrocarbon rings or substituted or unsubstituted heterocycles may be formed.

[0174] In this specification, when adjacent groups in R2 combine to form substituted or unsubstituted rings, substituted or unsubstituted benzene rings may be formed.

[0175] In this specification, R3 is a heterocyclic group comprising a polycyclic compound selected from at least one of N, O, and S; or a heterocyclic group comprising a monocyclic compound selected from at least one of O and S, whether substituted or unsubstituted.

[0176] In this specification, R3 refers to substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted benzofuranyl Azolium, substituted or unsubstituted benzothiazolium, substituted or unsubstituted naphthyl The azole group, or the substituted or unsubstituted naphthiazole group, can combine with adjacent groups to form a substituted or unsubstituted ring in substituents that are further substituted by these substituents.

[0177] In this specification, R, R' and R6 to R9 may be the same as or different from each other, and each independently represents hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group comprising at least one selected from N, O and S.

[0178] In this specification, R and R' are the same or different from each other, and are each independently hydrogen, deuterium, or substituted or unsubstituted aryl groups.

[0179] In this specification, R and R' may be the same as or different from each other, and each independently is hydrogen, deuterium, or an aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

[0180] In this specification, R and R' may be the same as or different from each other, and each independently represents hydrogen, deuterium, phenyl, biphenyl, terphenyl or naphthyl.

[0181] In this specification, R and R' are the same as or different from each other, and each is independently hydrogen, deuterium or phenyl.

[0182] In this specification, R6 and R7 may be the same as or different from each other, and each is independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group.

[0183] In this specification, R8 and R9 may be the same as or different from each other, and each independently represents hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group comprising at least one selected from N, O and S.

[0184] In this specification, R8 and R9 may be the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms comprising at least one selected from N, O, and S.

[0185] In this specification, R8 and R9 may be the same as or different from each other, and each independently represents hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, cyclohexyl, cyclopentyl, tetrahydronaphthyl substituted or unsubstituted with alkyl, phenyl, biphenyl, terphenyl, naphthyl, furanyl or thiophene.

[0186] In this specification, R61 to R64 may be the same as or different from each other, and each independently represents hydrogen; deuterium; halogen group; cyano; nitro; hydroxyl; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group comprising at least one selected from N, O and S.

[0187] In this specification, R61 to R64 may be the same as or different from each other, and each independently represents hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group comprising at least one selected from N, O and S.

[0188] In this specification, R61 to R64 may be the same as or different from each other, and each is independently hydrogen or deuterium.

[0189] In this specification, L1 and L2 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group.

[0190] In this specification, L1 and L2 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group with 6 to 30 carbon atoms.

[0191] In this specification, L1 and L2 may be the same as or different from each other, and each independently is a directly bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted fluorene.

[0192] According to one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each may be directly bonded or represented by any of the following structures independently.

[0193]

[0194] In the above structure,

[0195] Y1 and Y2 are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.

[0196] According to one embodiment of this specification, Ar is a substituted or unsubstituted aryl group.

[0197] In this specification, Ar is an aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0198] In this specification, Ar is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted triphenylene, or a substituted or unsubstituted pyrene.

[0199] In this specification, Ar can be represented by any of the following structures.

[0200]

[0201] In the above structure,

[0202] B1 to B7 are each independently hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.

[0203] b1 is an integer from 1 to 5.

[0204] b2 is an integer from 1 to 9.

[0205] b3 is an integer from 1 to 13.

[0206] b4 and b5 are each integers from 0 to 7.

[0207] When b1 is 2 or more, B1 values ​​are either the same or different from each other.

[0208] When b2 is 2 or more, B2 values ​​are either the same or different from each other.

[0209] When b3 is 2 or more, B3 values ​​are either the same or different from each other.

[0210] When b4 is 2 or more, B4 values ​​are either the same or different from each other.

[0211] When b5 is 2 or more, B5 values ​​are either the same or different from each other.

[0212] According to one embodiment of this specification, B1 to B5 are hydrogen or deuterium.

[0213] According to one embodiment of this specification, B6 and B7 are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

[0214] According to one embodiment of this specification, B6 and B7 are each independently an alkyl group having 1 to 60 carbon atoms, either substituted or unsubstituted, or an aryl group having 6 to 60 carbon atoms, either substituted or unsubstituted.

[0215] According to one embodiment of this specification, B6 and B7 are each independently an alkyl group having 1 to 30 carbon atoms, either substituted or unsubstituted, or an aryl group having 6 to 30 carbon atoms, either substituted or unsubstituted.

[0216] In this specification, the compound of chemical formula 1 is any one of the following structures.

[0217]

[0218]

[0219]

[0220]

[0221]

[0222] .

[0223] In addition, this specification provides organic light-emitting devices containing the compounds mentioned above.

[0224] In one embodiment of this specification, an organic light-emitting device is provided, comprising: a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers contain the aforementioned compound.

[0225] The organic layers of the organic light-emitting device described in this specification can be formed as a single layer or as a multilayer structure with two or more organic layers stacked on top of each other. For example, the organic light-emitting device of this invention can have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer as organic layers. However, the structure of the organic light-emitting device is not limited to this and may include fewer organic layers.

[0226] In one embodiment of this specification, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or hole transport layer contains the compound described above.

[0227] In one embodiment of this specification, the organic layer includes a light-emitting layer, which contains the aforementioned compound. Specifically, the light-emitting layer may include a host containing the aforementioned compound and a dopant.

[0228] In one embodiment of this specification, the organic layer includes an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer contains the compound described above.

[0229] In one embodiment of this specification, the organic layer includes a light-emitting layer, and further includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a hole modulation layer, and an electron modulation layer.

[0230] In one embodiment of this specification, the organic light-emitting device includes: an anode, a cathode, and one or more organic layers disposed between the anode and the cathode. The organic layer includes: 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. The light-emitting layer contains the compound.

[0231] In one embodiment of this specification, the organic layer of the hole transport region may be selected from one or more layers in the group consisting of a hole transport layer, a hole injection layer, a layer that performs both hole transport and hole injection, and a hole regulation layer.

[0232] In one embodiment of this specification, the organic layer of the electron transport region may be selected from one or more layers in the group consisting of an electron transport layer, an electron injection layer, a layer that performs both electron transport and electron injection, and an electron conditioning layer.

[0233] In another embodiment, the organic light-emitting device can be an organic light-emitting device with a structure (normal type) in which a first electrode, one or more organic layers and a second electrode are sequentially stacked on a substrate.

[0234] In another embodiment, the organic light-emitting device can be an organic light-emitting device with a reverse structure (inverted type) in which a second electrode, one or more organic layers and a first electrode are sequentially stacked on a substrate.

[0235] For example, the organic light-emitting devices described above can have the layered structure described below, but are not limited to this.

[0236] (1) Anode / hole transport layer / light-emitting layer / cathode

[0237] (2) Anode / hole injection layer / hole transport layer / light emission layer / cathode

[0238] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0239] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0240] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0241] (6) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / cathode

[0242] (7) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / electron injection layer / cathode

[0243] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light emission layer / electron transport layer / cathode

[0244] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light emission layer / electron transport layer / electron injection layer / cathode

[0245] (10) Anode / Hole transport layer / Hole modulation layer / Light emission layer / Electron transport layer / Cathode

[0246] (11) Anode / hole transport layer / hole modulation layer / light emission layer / electron transport layer / electron injection layer / cathode

[0247] (12) Anode / hole injection layer / hole transport layer / hole modulation layer / light emission layer / electron transport layer / cathode

[0248] (13) Anode / hole injection layer / hole transport layer / hole modulation layer / light emission layer / electron transport layer / electron injection layer / cathode

[0249] (14) Anode / Hole transport layer / Light emission layer / Electron modulation layer / Electron transport layer / Cathode

[0250] (15) Anode / Hole transport layer / Light emission layer / Electron modulation layer / Electron transport layer / Electron injection layer / Cathode

[0251] (16) Anode / Hole injection layer / Hole transport layer / Light emission layer / Electron modulation layer / Electron transport layer / Cathode

[0252] (17) Anode / Hole injection layer / Hole transport layer / Light emission layer / Electron modulation layer / Electron transport layer / Electron injection layer / Cathode

[0253] (18) Anode / hole injection layer / hole transport layer / light-emitting layer / layer that simultaneously performs electron injection and transport / cathode

[0254] (19) Anode / Hole injection layer / Hole transport layer / Hole conditioning layer / Light emission layer / Electron conditioning layer / Electron transport layer / Electron injection layer / Cathode

[0255] (20) Anode / Hole injection layer / Hole transport layer / Hole conditioning layer / Light emission layer / Electron conditioning layer / Electron transport layer / Cathode

[0256] (21) Anode / hole injection layer / hole transport layer / hole conditioning layer / light emission layer / electron conditioning layer / layer that performs both electron injection and transport simultaneously / cathode

[0257] For example, the structure of an organic light-emitting device according to one embodiment of this specification is illustrated in... Figure 1 and 2 .

[0258] Figure 1 The diagram illustrates the structure of an organic light-emitting device in which a first electrode 2, an organic layer 3, and a second electrode 4 are sequentially stacked on a substrate 1.

[0259] Figure 2 The diagram illustrates the structure of an organic light-emitting device in which a first electrode 2, a first organic layer 5, a light-emitting layer 6, a second organic layer 7, and a second electrode 4 are sequentially stacked on a substrate 1. In the structure shown above, the aforementioned compound may be contained in the light-emitting layer 6.

[0260] The above Figure 2 An organic light-emitting device is illustrated, wherein, depending on the first electrode and the second electrode, the first organic layer and the second organic layer can each be a hole transport region and an electron transport region, respectively. Here, the hole transport region refers to the organic layer between the anode and the light-emitting layer, for example, including at least one of a hole injection layer, a hole transport layer, and a hole modulation layer; the electron transport region refers to the organic layer between the cathode and the light-emitting layer, for example, including at least one of an electron injection layer, an electron transport layer, and an electron modulation layer.

[0261] The organic light-emitting devices described herein, except for those containing one or more organic layers containing the compounds described herein, can be manufactured using materials and methods known in the art.

[0262] When the aforementioned organic light-emitting device comprises a plurality of organic layers, the organic layers may be formed from the same substance or different substances.

[0263] The organic light-emitting device described in this specification, except that one or more layers of the organic material contain the aforementioned compound (i.e., the compound represented by the aforementioned chemical formula 1), can be manufactured using materials and methods known in the art.

[0264] For example, the organic light-emitting device of this specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be achieved by: depositing a metal or a conductive metal oxide or alloy thereof onto the substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form the first electrode; then forming an organic layer comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer on the first electrode; and finally depositing a material suitable for use as the second electrode onto the organic layer. Alternatively, the organic light-emitting device can also be manufactured by sequentially depositing a second electrode material, an organic layer, and a first electrode material onto the substrate.

[0265] Furthermore, the compounds of Formula 1 mentioned above can be used to form organic layers not only by vacuum evaporation but also by solution coating when manufacturing organic light-emitting devices. Here, solution coating refers to methods such as spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, and roller coating, but is not limited to these.

[0266] In one embodiment of this specification, the first electrode is an anode and the second electrode is a cathode.

[0267] In another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0268] The anode described above is the electrode for injecting holes. As the anode material, it is generally preferred to be a material with a high work function in order to enable holes to be smoothly injected into the organic layer. Specific examples of anode materials that can be used in this invention include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; 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; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0269] The cathode described above is the electrode for injecting electrons. As a cathode material, it is generally preferred to be a material with a low work function in order to facilitate the injection of electrons into the organic 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 their alloys; multilayer structures such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0270] The aforementioned hole injection layer is a layer that injects holes from the electrode. Preferably, the hole injection material is a compound that possesses the ability to transport holes, the effect of injecting holes from the first electrode, excellent hole injection performance for the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material, and exhibits excellent thin film formation capability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the first electrode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic compounds, hexanitrile hexaazabenzophenanthrene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinones, and conductive polymers based on polyaniline and polythiophene.

[0271] According to one embodiment of this specification, the hole injection layer comprises, but is not limited to, a compound represented by the chemical formula HI-1.

[0272] [Chemical formula HI-1]

[0273]

[0274] In the above chemical formula HI-1,

[0275] At least one of X'1 to X'6 is N, and the rest are CH.

[0276] R309 to R314 may be the same as or different from each other, and each is independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or combined with adjacent groups to form substituted or unsubstituted rings.

[0277] According to one embodiment of this specification, X'1 to X'6 are N.

[0278] According to one embodiment of this specification, R309 to R314 are cyano groups.

[0279] According to one embodiment of this specification, the above chemical formula HI-1 is represented by the following compound.

[0280]

[0281] The aforementioned hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is a material capable of receiving holes from the first electrode or the hole injection layer and transferring them to the light-emitting layer; materials with high hole mobility are suitable. Specific examples include aryl amine-based organic compounds, conductive polymers, and block copolymers that simultaneously contain conjugated and non-conjugated portions, but are not limited to these.

[0282] In one embodiment of this specification, the hole transport layer comprises a compound with the chemical formula HT-1.

[0283] [Chemical formula HT-1]

[0284]

[0285] In the above chemical formula HT-1,

[0286] L101 is a directly bonded, substituted, or unsubstituted aryl group.

[0287] R101 and R102 may be the same as or different from each other, and each may independently be hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic.

[0288] R103 and R104 may be the same as or different from each other, and each may be independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

[0289] When o is 1 or 2, and o is more than 2, the structures inside the parentheses are the same or different from each other.

[0290] In one embodiment of this specification, L101 is a directly bonded, substituted or unsubstituted phenylene, or a substituted or unsubstituted naphthylene.

[0291] In one embodiment of this specification, L101 is a directly bonded, substituted, or unsubstituted phenylene oxide.

[0292] In one embodiment of this specification, L101 is directly bonded or phenylene.

[0293] In one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each may be a substituted or unsubstituted aryl group independently.

[0294] In one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each may be a substituted or unsubstituted monocyclic aryl group or a substituted or unsubstituted polycyclic aryl group.

[0295] In one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraceneyl, a substituted or unsubstituted phenanthrene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted pyrene, or a substituted or unsubstituted fluorene.

[0296] In one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each may be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted fluorenyl.

[0297] In one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently a phenyl, biphenyl, or fluorene group substituted with an alkyl group.

[0298] In one embodiment of this specification, R103 and R104 may be the same as or different from each other, and each may be independently a substituted or unsubstituted alkyl group.

[0299] In one embodiment of this specification, R103 and R104 may be the same as or different from each other, and each is independently an alkyl group.

[0300] In one embodiment of this specification, R103 and R104 are methyl groups.

[0301] In one embodiment of this specification, the above chemical formula HT-1 is represented by the following compound.

[0302]

[0303] In one embodiment of this specification, a hole modulation layer may be disposed between the hole transport layer and the light-emitting layer. The hole modulation layer may be made of materials known in the art.

[0304] According to one embodiment of this specification, the hole-modifying layer comprises, but is not limited to, a compound represented by the following chemical formula EB-1.

[0305] [Chemical formula EB-1]

[0306]

[0307] In the above chemical formula EB-1,

[0308] R315 to R317 may be the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and any one of the groups selected from the group consisting of combinations thereof, or may be combined with adjacent groups to form substituted or unsubstituted rings.

[0309] r315 is an integer from 1 to 5. When r315 is 2 or more, two or more of the above R315 are either the same or different from each other.

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

[0311] According to one embodiment of this specification, R317 is any one of the group consisting of substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof.

[0312] According to one embodiment of this specification, R317 is any one of phenyl, biphenyl, and combinations thereof.

[0313] According to one embodiment of this specification, R315 and R316 may be the same as or different from each other, and each may be a substituted or unsubstituted aryl group independently.

[0314] According to one embodiment of this specification, R315 and R316 are each independently a substituted or unsubstituted polycyclic aryl group.

[0315] According to one embodiment of this specification, R315 and R316 are each independently a substituted or unsubstituted phenanthrene.

[0316] According to one embodiment of this specification, R315 and R316 are phenotypes.

[0317] According to one embodiment of this specification, the above chemical formula EB-1 is represented by the following compound.

[0318]

[0319] In one embodiment of this specification, the light-emitting layer comprises a host and a dopant.

[0320] The main material of the luminescent layer includes aromatic fused-ring derivatives or heterocyclic compounds. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include carbazole derivatives, dibenzofuran, dibenzofuran derivatives, dibenzothiophene, dibenzothiophene derivatives, and ladder-type furan compounds. ), pyrimidine derivatives, etc., but not limited to these.

[0321] Regarding the dopants in the emissive layer, when the emissive layer emits red light, phosphorescent materials such as PIQIr(acac) (bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac) (bis(1-phenylquinoline)acetylacetonateiridium), PQIr (tris(1-phenylquinoline)iridium), PtOEP (octaethylporphyrin platinum), or fluorescent materials such as Alq3 (tris(8-hydroxyquinolino)aluminum) can be used as the phosphorescent dopants, but these are not the only options. When the luminescent layer emits green light, phosphorescent materials such as Ir(ppy)3 (fac tris(2-phenylpyridine)iridium, or fluorescent materials such as Alq3 (tris(8-hydroxyquinoline)aluminum) can be used as luminescent dopants, but these are not the only options. When the luminescent layer emits blue light, phosphorescent materials such as (4,6-F2ppy)2Irpic, or fluorescent materials such as spiro-DPVBi, spiro-6P, stilbene (DSB), stilbene arylene (DSA), PFO-based polymers, and PPV-based polymers can be used as luminescent dopants, but these are not the only options.

[0322] In one embodiment of this specification, the above-mentioned subject comprises one or more compounds of chemical formula 1 of this application.

[0323] In one embodiment of this specification, the aforementioned body comprises a first anthracene derivative substituted with deuterium and a second anthracene derivative not substituted with deuterium, wherein either the first anthracene derivative or the second anthracene derivative comprises a compound of the aforementioned chemical formula 1.

[0324] In one embodiment of this specification, when the main body of the light-emitting layer comprises a first anthracene derivative and a second anthracene derivative, the mass ratio of the first anthracene derivative to the second anthracene derivative can be 99:1 to 1:99, 90:10 to 10:90, 80:20 to 20:80, 70:30 to 30:70, or 60:40 to 40:60.

[0325] In one embodiment of this specification, the aforementioned deuterated first anthracene derivative comprises the compound of chemical formula 1 of this application.

[0326] In one embodiment of this specification, the dopant used with the compound of chemical formula 1 of this application is a fluorescent dopant.

[0327] In one embodiment of this specification, the dopant used with the compound of Formula 1 of this application includes a pyrene compound or a non-pyrene compound.

[0328] In one embodiment of this specification, the non-pyrene compound used in conjunction with the compound of Formula 1 of this application comprises a boron compound.

[0329] In one embodiment of this specification, the aforementioned pyrene compounds may be selected from the compounds exemplified in Japanese Patent Publication No. 4205059 (JP 4205059 B2), Japanese Patent Publication No. 4267623 (JP 4267623 B2), Japanese Patent Publication No. 4188401 (JP 4188401 B2), Japanese Patent Publication No. 4848134 (JP 4848134B2), Japanese Patent Publication No. 6082179 (JP 6082179 B2), and Japanese Patent Publication No. 5587302 (JP 5587302 B2).

[0330] In one embodiment of this specification, the pyrene compound used in conjunction with the compound of chemical formula 1 of this application may be a compound of chemical formula D1.

[0331] [Chemical formula D1]

[0332]

[0333] In the above chemical formula D1, Ar1 to Ar4 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0334] In one embodiment of this specification, Ar1 and Ar3 may be the same as or different from each other, and each may be a substituted or unsubstituted aryl group independently.

[0335] In one embodiment of this specification, Ar1 and Ar3 may be the same as or different from each other, and each is independently an aryl group that is substituted with or unsubstituted with an alkyl group.

[0336] In one embodiment of this specification, Ar1 and Ar3 may be the same as or different from each other, and each is independently a phenyl group that is substituted with or unsubstituted with a methyl group.

[0337] In one embodiment of this specification, Ar2 and Ar4 may be the same as or different from each other, and each may be a substituted or unsubstituted heterocyclic group independently.

[0338] In one embodiment of this specification, Ar2 and Ar4 may be the same as or different from each other, and each may be independently a substituted or unsubstituted dibenzofuranyl group.

[0339] In one embodiment of this specification, Ar2 and Ar4 are dibenzofuranyl groups.

[0340] In one embodiment of this specification, Ar1 and Ar3 may be the same as each other.

[0341] In one embodiment of this specification, Ar2 and Ar4 may be the same as each other.

[0342] In one embodiment of this specification, the compound of chemical formula D1 can be one of the following compounds.

[0343]

[0344] In one embodiment of this specification, the aforementioned boron compound may be selected from the compounds exemplified in Japanese Patent Publication No. 5935199 (JP 5935199 B2), International Patent Publication No. WO2017-138526A1, Japanese Patent Publication No. 6611825 (JP 6611825 B2), International Patent Publication No. WO2018-047639A1, International Patent Publication No. WO2018-110497A1, and Japanese Patent Publication No. 2020-097561 (JP 2020-097561 A).

[0345] In one embodiment of this specification, the non-pyrene compound used in conjunction with the compound of chemical formula 1 of this application may be a compound of chemical formula D2.

[0346] [Chemical formula D2]

[0347]

[0348] In the above chemical formula D2,

[0349] Ar5 and Ar6 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0350] Z1 to Z3 are hydrogen, deuterium, halogen groups, cyano, nitro, hydroxyl, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic groups, or groups adjacent to each other that combine to form substituted or unsubstituted rings.

[0351] In one embodiment of this specification, Ar5 and Ar6 may be the same as or different from each other, and each may be a substituted or unsubstituted aryl group independently.

[0352] In one embodiment of this specification, Ar5 and Ar6 may be the same as or different from each other, and each is independently an aryl group that is substituted with or unsubstituted with an alkyl group.

[0353] In one embodiment of this specification, Ar5 and Ar6 may be the same as or different from each other, and each is independently a phenyl group that is substituted with or unsubstituted with a methyl group.

[0354] In one embodiment of this specification, Z1 to Z3 may be the same as or different from each other, and each may be independently a substituted or unsubstituted alkyl group.

[0355] In one embodiment of this specification, Z1 to Z3 are methyl groups.

[0356] In one embodiment of this specification, the compound of chemical formula D2 may be one of the following compounds.

[0357]

[0358] In one embodiment of this specification, the weight ratio of the host and dopant in the light-emitting layer can be 50:50, 60:40, 70:30, 80:20, 90:10, 91:9, 92:8, 93:7, 94:6, 95:5, 96:4, 97:3, 98:2 or 99:1.

[0359] In one embodiment of this specification, the above-mentioned compound is the main body, specifically a fluorescent main body, and more specifically a blue fluorescent main body.

[0360] In one embodiment of this specification, the maximum emission peak (λ) of the luminescent layer comprising the compound represented by the above-described chemical formula 1 is... 最大（max） The wavelength range is 400nm to 470nm.

[0361] In one embodiment of this specification, the light-emitting layer comprises a host and a dopant in a mass ratio of 99:1 to 1:99.

[0362] In one embodiment of this specification, the light-emitting layer comprises a host and a dopant in a mass ratio of 99:1 to 10:90.

[0363] In one embodiment of this specification, the light-emitting layer comprises a host and a dopant in a mass ratio of 99:1 to 50:50.

[0364] In one embodiment of this specification, an electron conditioning layer may be disposed between the electron transport layer and the light-emitting layer. This electron conditioning layer is a layer that prevents holes from reaching the cathode, and is typically formed under the same conditions as a hole-blocking layer. Specifically, there are... Diazole or triazole derivatives, phenanthrene-rhein derivatives, BCP, aluminum complexes, but not limited to these.

[0365] In one embodiment of this specification, the above-mentioned electronic conditioning layer comprises a compound with the following chemical formula HB-1.

[0366] [Chemical formula HB-1]

[0367]

[0368] In the above chemical formula HB-1,

[0369] L501 to L503 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group.

[0370] R501 and R502 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic.

[0371] In one embodiment of this specification, L501 to L503 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted phenylene or a substituted or unsubstituted naphthylene.

[0372] In one embodiment of this specification, L501 to L503 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted phenylene oxide.

[0373] In one embodiment of this specification, L501 to L503 may be the same as or different from each other, and each may be directly bonded or benzene independently.

[0374] In one embodiment of this specification, R501 and R502 may be the same as or different from each other, and each may be a substituted or unsubstituted aryl group independently.

[0375] In one embodiment of this specification, R501 and R502 may be the same as or different from each other, and each may be a substituted or unsubstituted monocyclic aryl group or a substituted or unsubstituted polycyclic aryl group.

[0376] In one embodiment of this specification, R501 and R502 may be the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraceneyl, a substituted or unsubstituted phenanthrene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted pyrene, or a substituted or unsubstituted fluorene.

[0377] In one embodiment of this specification, R501 and R502 may be the same as or different from each other, and each may be independently a substituted or unsubstituted phenyl or a substituted or unsubstituted naphthyl group.

[0378] In one embodiment of this specification, R501 and R502 may be the same as or different from each other, and each is independently phenyl or naphthyl.

[0379] In one embodiment of this specification, the above chemical formula HB-1 is represented by the following compound.

[0380]

[0381] In one embodiment of this specification, the electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is a material capable of effectively receiving electrons from the second electrode and transferring them to the light-emitting layer; a material with high electron mobility is suitable. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavonoid-metal complexes, etc., but are not limited to these. The electron transport layer can be used with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are common materials with low work functions and accompanied by an aluminum or silver layer. Specifically, these are cesium, barium, calcium, ytterbium, and samarium, and in each case, they are accompanied by an aluminum or silver layer.

[0382] In one embodiment of this specification, the electron transport layer comprises a compound with the chemical formula ET-1.

[0383] [Chemical formula ET-1]

[0384]

[0385] In the above chemical formula ET-1,

[0386] R601 to R604 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic.

[0387] In one embodiment of this specification, R601 to R604 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0388] In one embodiment of this specification, R601 to R604 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group.

[0389] In one embodiment of this specification, R601 to R604 may be the same as or different from each other, and each is independently an aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0390] In one embodiment of this specification, R601 to R604 may be the same as or different from each other, and each is independently an aryl group with 6 to 20 carbon atoms, either substituted or unsubstituted.

[0391] In one embodiment of this specification, R601 to R604 may be the same as or different from each other, and each is independently an aryl group with 6 to 10 carbon atoms, either substituted or unsubstituted.

[0392] In one embodiment of this specification, R601 to R604 are phenyl.

[0393] In one embodiment of this specification, the compound of the above chemical formula ET-1 is represented by the following compound.

[0394]

[0395] In one embodiment of this specification, the electron transport layer may together comprise the compound of the chemical formula ET-1 and a lithium complex.

[0396] The aforementioned electron injection layer is a layer that injects electrons from the electrode. Preferably, compounds are those that possess electron transport capabilities, effectively inject electrons from the second electrode, exhibit excellent electron injection performance for the light-emitting layer or light-emitting material, prevent excitons generated in the light-emitting layer from migrating to the hole injection layer, and possess excellent thin-film forming ability. Specifically, these include fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, but not limited to these.

[0397] Examples of the aforementioned metal coordination compounds include lithium 8-hydroxyquinoline, 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)gallium chloride, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, and bis(2-methyl-8-quinoline)(2-naphthol)gallium, but are not limited to these.

[0398] In one embodiment of this specification, an organic coating may be formed on the cathode. For example, the coating may contain a carbazole-based compound.

[0399] In one embodiment of this specification, the coating layer comprises a compound with the chemical formula CL-1.

[0400] [Chemical formula CL-1]

[0401]

[0402] In the above chemical formula CL-1,

[0403] R701 to R703 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic.

[0404] In one embodiment of this specification, R701 to R703 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0405] In one embodiment of this specification, R701 to R703 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group.

[0406] In one embodiment of this specification, R701 to R703 may be the same as or different from each other, and each is independently an aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0407] In one embodiment of this specification, R701 to R703 may be the same as or different from each other, and each is independently an aryl group with 6 to 20 carbon atoms, either substituted or unsubstituted.

[0408] In one embodiment of this specification, R701 to R703 may be the same as or different from each other, and each is independently an aryl group with 6 to 10 carbon atoms, either substituted or unsubstituted.

[0409] In one embodiment of this specification, R701 to R703 are phenyl groups.

[0410] In one embodiment of this specification, the compound of the above chemical formula CL-1 is represented by the following chemical formula.

[0411]

[0412] Depending on the materials used, the organic light-emitting device according to this specification can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0413] The organic light-emitting device according to this specification can be included in various electronic devices for use. For example, the aforementioned electronic devices may be display panels, touch panels, solar modules, lighting devices, etc., but are not limited thereto.

[0414] The compounds represented by Chemical Formula 1 in this specification can be manufactured with a core structure as shown in the reaction formulas of Manufacturing Examples 1 to 7 below. Substituents can be combined by methods known in the art, and the type, position, and number of substituents can be changed by techniques known in the art.

[0415] Methods of implementing the invention

[0416] The present specification will now be described in more detail through examples. However, the examples described below are merely illustrative and are not intended to limit the scope of the specification.

[0417] Manufacturing Example 1 (Synthesis of A1 to A8)

[0418] [Reaction Formula 1]

[0419]

[0420] Here, R2, r2, and X1 are defined in the same way as in chemical formula 1.

[0421] R2-1 and R2-2 are defined the same as R2, where r2-1 is 1 or 2, and r2-2 is an integer from 1 to 4.

[0422] SM1 (1 equivalent) and SM2 (1.05 equivalent) were added to excess tetrahydrofuran (THF), followed by the addition of 2M potassium carbonate aqueous solution (30 v / v to THF), and tetra(triphenylphosphine)palladium (2 mol%). The mixture was then heated and stirred for 10 hours. The temperature was lowered to room temperature, and after the reaction was complete, the potassium carbonate aqueous solution was removed, and chromatography was performed. After solvent removal, dimethylacetamide (DMAc, excess) and potassium carbonate (3 equivalents) were added, and the mixture was stirred and refluxed for 5 hours. Once the reaction was confirmed to be complete, the temperature was lowered to room temperature, water (1.5 v / v to DMAc) was added, and the mixture was filtered. The resulting solid was purified by column chromatography using dichloromethane and hexane to produce intermediate A.

[0423] In the above-mentioned synthesis method of compound A, SM1 and SM2 were modified as shown in Table A below. Otherwise, intermediates A1 to A8 were synthesized by the same method.

[0424] [Table A]

[0425]

[0426]

[0427] Manufacturing Example 2

[0428] Manufacturing Example 2-1 (Synthesis of B1 to B32)

[0429] [Reaction 2]

[0430]

[0431] Here, R2, R3, r2, and X1 are defined in the same way as in chemical formula 1.

[0432] Intermediate A (1 equivalent) and SM3 (1.05 equivalent) synthesized in Manufacturing Example 1 were added to excess tetrahydrofuran, followed by the addition of 2M aqueous potassium carbonate solution (30 v / v to THF), and then tetra(triphenylphosphine)palladium (2 mol%). The mixture was heated and stirred for 10 hours. After the temperature was lowered to room temperature and the reaction was stopped, the aqueous potassium carbonate solution was removed, and layer separation was performed. Then, the solvent was removed, and the mixture was purified by recrystallization using chloroform and hexane to produce intermediate B.

[0433] In the above method for synthesizing intermediate B, A and SM3 were modified as shown in Table B below. Otherwise, B1 to B32 in [Table B] were synthesized by the same method.

[0434] [Table B]

[0435]

[0436]

[0437]

[0438]

[0439]

[0440]

[0441] Manufacturing Example 2-2 (Synthesis of Compound B33)

[0442]

[0443] Here, R2, R3, r2, and X1 are defined in the same way as in chemical formula 1.

[0444] Intermediate A (1 equivalent), SM3 (1.05 equivalent), and sodium tert-butoxide (1.5 equivalent) synthesized in Example 1 above were added to toluene, heated and stirred until refluxed, and then [1,1'-bis(diphenylphosphine)ferrocene]dichloropalladium (658 mg, 1 mol%) was added. After cooling to room temperature and stopping the reaction, the mixture was recrystallized from tetrahydrofuran and ethyl acetate to produce B33 [Table B-2].

[0445] [Table B-2]

[0446]

[0447] Manufacturing Example 3 (Synthesis of compounds C1 to C33)

[0448] [Reaction 3]

[0449]

[0450] Here, R2, R3, r2, and X1 are defined as in Formula 1, and Nf stands for nonafluorobutyl group.

[0451] Intermediate B (1 equivalent) synthesized in Manufacturing Example 2 above and potassium carbonate (2.3 equivalents) were added to excess acetonitrile (AN). Then, 2 equivalents of perfluorobutanesulfonic acid (NNF) were added dropwise at room temperature with stirring. After 5 hours, once the reaction was confirmed to be complete, water was added, and the mixture was stirred and filtered. The solid was then extracted with excess chloroform and purified by recrystallization using chloroform and ethanol to produce intermediate C.

[0452] In the above method for synthesizing intermediate C, intermediates C1 to C33 in [Table C] below are synthesized by changing B as shown in Table C below, except that they are synthesized by the same method.

[0453] [Table C]

[0454]

[0455]

[0456]

[0457]

[0458]

[0459]

[0460] Manufacturing Example 4 (Synthesis of compounds D1 to D2)

[0461] [Reaction 4]

[0462]

[0463] Here, R2, R3, r2, X1, and L1 are defined as in Formula 1, and Nf is nonafluorobutyl.

[0464] C21 or C22 (1 equivalent) and SM4 (1.05 equivalent) from intermediate C synthesized in Example 3 above were added to tetrahydrofuran (excess), followed by the addition of 2M aqueous potassium carbonate solution (30 v / v to THF), and then tetra(triphenylphosphine)palladium (2 mol%). The mixture was heated and stirred for 10 hours. After the temperature was lowered to room temperature and the reaction was stopped, the aqueous potassium carbonate solution was removed, and layer separation was performed. The solvent was then removed, and the mixture was purified by recrystallization using chloroform and ethanol, thereby producing intermediates D (D1 and D2) as summarized in Table D below.

[0465] [Table D]

[0466]

[0467] Manufacturing Example 5 (Synthesis of compounds E1 to E33)

[0468] [Reaction 5]

[0469]

[0470] Here, R2, R3, r2, X1, and L1 are defined as in Formula 1, and Nf is nonafluorobutyl.

[0471] SM5 (1 equivalent) and SM6 (1.3 equivalent), equivalent to intermediates C or D synthesized in manufacturing examples 3 or 4 above, are added to 1,4-di Add potassium acetate (3 equivalents) to alkylene (12 times the mass ratio of SM5), stir and reflux. Add potassium acetate (0.02 equivalents) and tricyclohexylphosphine (0.04 equivalents) to 1,4-dialkylene oxide. After stirring in the alkane for 5 minutes, the mixture was added. After 2 hours, once the reaction was confirmed to be complete, the mixture was cooled to room temperature. Ethanol and water were added, and the mixture was filtered. It was then purified by recrystallization with ethyl acetate and ethanol, thus producing the aforementioned intermediate E.

[0472] In the above method for synthesizing intermediate E, SM5 and SM6 were modified as shown in Table E below. Otherwise, intermediates E1 to E33 in [Table E] were synthesized by the same method.

[0473] [Table E]

[0474]

[0475]

[0476]

[0477]

[0478]

[0479]

[0480] Manufacturing Example 6 (Synthesis of compounds 1 to 29 and 33 to 36)

[0481] [Reaction Formula 6]

[0482]

[0483] Here, R1, R2, R3, Ar, r, r1, r2, X1, L1, and L2 are defined in the same way as in chemical formula 1.

[0484] Intermediate E (1 equivalent) and SM7 (1.05 equivalent) synthesized in Manufacturing Example 5 above were added to tetrahydrofuran (excess), followed by the addition of 2M aqueous potassium carbonate solution (30 v / v to THF), and then tetra(triphenylphosphine)palladium (2 mol%). The mixture was heated and stirred for 10 hours. After cooling to room temperature and stopping the reaction, the aqueous potassium carbonate solution was removed, and layer separation was performed. The solvent was then removed, and the product was purified by recrystallization using toluene to obtain the product.

[0485] The compounds 1 to 29 and 33 to 36 in Table 1 below were synthesized by the same method except as shown in Table 1 below, with E and SM7 changed.

[0486] [Table 1]

[0487]

[0488]

[0489]

[0490]

[0491]

[0492]

[0493] Manufacturing Example 7 (Synthesis of Compounds 30 to 32)

[0494] [Reaction Formula 7]

[0495]

[0496] Here, R1, R2, R3, Ar, r, r1, r2, X1, L1, and L2 are defined the same as in chemical formula 1, D stands for deuterium, and n represents the number of atoms substituted by deuterium.

[0497] The reactants (1 equivalent) and trifluoromethanesulfonic acid (catalyst, cat.) were added to C6D6 (10-50 times the mass of the reactants), and the mixture was stirred at 70°C for 10 to 100 minutes. After the reaction was complete, D2O (excess) was added, and the mixture was stirred for 30 minutes, followed by the dropwise addition of trimethylamine (excess). The reaction mixture was transferred to a separatory funnel and extracted with water and chloroform. The extract was dried over MgSO4 and recrystallized by heating with toluene to obtain compounds 30 to 32 as shown in Table 2 below.

[0498] [Table 2]

[0499]

[0500] The deuterium substitution reaction of the above products was carried out with reference to the existing literature KR 1538534 B1. The degree of deuterium substitution of each product varies depending on the reaction time. Therefore, the total reaction time was adjusted to 50 minutes, and the substitution rate was determined based on the maximum m / z (M+) value.

[0501] <Example> OLED Manufacturing

[0502] The ITO / Ag / ITO substrate, deposited at 70 / 1000 / 70 Å as the anode, was cut into 50mm × 50mm × 0.5mm pieces and placed in distilled water containing detergent for ultrasonic washing. The detergent used was from Fischer Co., and the distilled water was filtered twice using a filter manufactured by Millipore Co. After washing the ITO (Indium Tin Oxide) for 30 minutes, the process was repeated twice with distilled water for 10 minutes of ultrasonic washing. Following the distilled water washing, the substrate was ultrasonically washed in the following order: isopropanol, acetone, and methanol, and then dried.

[0503] On the prepared anode, HI-1 was thermally vacuum-deposited to a thickness of 50 Å to form a hole injection layer. On the hole injection layer, HT1, as a hole transport material, was vacuum-deposited to a thickness of 1150 Å to form a hole transport layer. Then, a hole conditioning layer was formed using EB1 (150 Å). Next, the compound synthesized in Manufacturing Examples 6 or 7 was used as the host and vacuum-deposited with a dopant (2 wt%) to a thickness of 360 Å to form a light-emitting layer. Then, ET1 was deposited to a thickness of 50 Å to form an electron conditioning layer. Compound ET2 and Liq were mixed in a 7:3 ratio to form an electron transport layer with a thickness of 250 Å. Magnesium and lithium fluoride (LiF) were then used sequentially as electron injection layers with a thickness of 50 Å. <eil>After the film was formed, it was used as a cathode. A 200 Å layer was formed using magnesium and silver (1:4), followed by a 600 Å layer of CP1 vapor deposition to complete the device. During the above process, the vapor deposition rate of organic materials was maintained at 1 Å / second.

[0504]

[0505]

[0506]

[0507] The experimental results of organic light-emitting devices manufactured by using any one of compounds 1 to 36 synthesized in manufacturing examples 6 and 7 as the host material of the light-emitting layer and BD1 or BD2 as the dopant material of the light-emitting layer, namely Examples 1 to 42 and Comparative Examples 1 to 23, are shown in [Table 3].

[0508] At this time, the organic light-emitting device is at 20mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm². 2 The time (T95) at which the brightness reaches 95% of its initial value was determined at a current density.

[0509] [Table 3]

[0510]

[0511]

[0512]

[0513]

[0514] This invention relates to an anthracene blue phosphor host incorporating fused dibenzofuran or dibenzothiophene, and fluorene, etc. By substituting the units in a specific direction and introducing additional substituents, improvements in hole and electron injection, transport, and modulation characteristics have been identified. Examples of blue devices that satisfy the substitution positions, characteristic of this specification, show a significant improvement in device performance compared to Comparative Examples 1 to 19. Comparative Examples 2 to 5 are examples of using a structure as a blue phosphor host where the binding positions of the dibenzofuran unit and the anthracene and substituents are the same as those in the compound of Formula 1 of this specification, but with the addition of substituents containing silicon atoms. The device results show that the binding positions and substitution effects exhibited by the silicon-containing units are not as shown in the compound of Formula 1 of this specification.

[0515] The structural combination described in this specification modulates the migration and balance of holes and electrons within the blue fluorescent host by using specific directional bonding of dibenzofuran or dibenzothiophene and introducing heteroaryl groups as substituents into the aforementioned units, thereby producing excellent device performance.

[0516] Comparative Examples 6 to 17 are examples where the bonding positions of the anthracene and dibenzofuran units differ from those of the compounds of Formula 1 in this specification. The unit combinations are similar to those of the compounds of Formula 1 in this specification. However, it is evident that the combined effect of the bonding positions of the dibenzofuran unit with anthracene and the substitution positions of the substituents in the dibenzofuran unit results in a smaller improvement in device characteristics compared to the compounds of Formula 1 in this specification.

[0517] Organic electroluminescent devices made from compound derivatives according to the chemical formulas of this specification, by using the compounds of Manufacturing Examples 6 and 7 as the main body of blue organic electroluminescent devices, can adjust the good hole injection effect into the light-emitting layer. Through the balance of holes and electrons in the organic light-emitting device brought about by the chemical structure, the devices according to the present invention exhibit excellent characteristics in terms of efficiency, driving voltage, and stability.< / eil>

Claims

1. A compound of the following chemical formula 1: Chemical Formula 1 In the chemical formula 1, X1 is either O or S. R1 is hydrogen; deuterium; or a C6-C30 aryl group. R2 is hydrogen; deuterium; C1-C10 alkyl; or C6-C30 aryl, or adjacent groups optionally combined to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring. R3 is a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothiopheneyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiopheneyl, or a substituted or unsubstituted benzofuranyl. Azolium, substituted or unsubstituted benzothiazolium, substituted or unsubstituted naphthyl Azolium group, or substituted or unsubstituted naphthothiazolium group, L1 is either directly bonded or phenylene. L2 is a direct bond. Ar can be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted triphenylene, or a substituted or unsubstituted pyrene. r1 is an integer from 1 to 8. r2 is an integer from 1 to 6. When r1 is 2 or more, R1 values ​​are either the same or different. When r² is 2 or higher, R² values ​​are either the same or different. For any integer r between 1 and 4, when r is 2 or greater, Ar is either the same or different from each other. The term "substitution" here means substitution by one or more substituents selected from the group consisting of deuterium, halogen groups, cyano (-CN), silyl, C1-C10 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, and C2-C30 heterocyclic groups. The compounds mentioned above do not include the following compounds: 。 2. The compound according to claim 1, wherein, The chemical formula 1 is the following chemical formula 1-1: Chemical Formula 1-1 In the chemical formula 1-1, X1, R1, R2, R3, r1, L1, L2, Ar, and r are defined in the same way as in chemical formula 1. r2 is an integer from 1 to 4.

3. The compound according to claim 1, wherein, The chemical formula 1 is any one of the following chemical formulas 1-2 and 1-3: Chemical formula 1-2 Chemical formulas 1-3 In the chemical formulas 1-2 and 1-3, X1, R1, R3, r1, L1, L2, Ar, and r are defined in the same way as in chemical formula 1. R4 and R5 may be the same as or different from each other, and each is independently hydrogen; deuterium; C1-C10 alkyl; or C6-C30 aryl. r4 is an integer from 1 to 6. r5 is an integer from 1 to 8. When r4 is 2 or higher, R4 values ​​are either the same or different from each other. When r5 is 2 or more, R5 values ​​are either the same or different from each other.

4. A compound having any one of the following chemical formulas 2-1 to 2-4 and chemical formulas 4 to 5: Chemical formula 2-1 Chemical formula 2-2 Chemical formula 2-3 Chemical formula 2-4 Chemical Formula 4 Chemical formula 5 In the chemical formulas 2-1 to 2-4 and chemical formulas 4 to 5, X1 is either O or S. R1 is hydrogen; deuterium; or a C6-C30 aryl group. R2 is hydrogen; deuterium; C1-C10 alkyl; or C6-C30 aryl, or adjacent groups optionally combined to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring. L1 is either directly bonded or phenylene. L2 is a direct bond. Ar can be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted triphenylene, or a substituted or unsubstituted pyrene. r1 is an integer from 1 to 8. When r1 is 2 or more, R1 values ​​are either the same or different. For any integer r between 1 and 4, when r is 2 or greater, Ar is either the same or different from each other. X2 is NR, O, or S. X4 is either O or S. X5 is either N or CR'. R, R', and R8 to R9 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C3-C30 cycloalkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heterocyclic group comprising at least one selected from N, O, and S. X6 is NR'', O, or S. R'' and R61 to R64 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C3-C30 cycloalkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heterocyclic group comprising at least one selected from N, O, and S. r2 is an integer from 1 to 4. r8 is an integer from 1 to 4. r9 is an integer from 1 to 6. When r8 is 2 or higher, R8 values ​​are either the same or different from each other. When r9 is 2 or higher, R9 values ​​are either the same or different from each other. r61 is an integer from 1 to 7. r62 and r63 are each integers from 1 to 9. r64 is an integer from 1 to 11. When r61 is 2 or higher, R61 values ​​are either the same or different. When r62 is 2 or higher, R62 values ​​are either the same or different. When r63 is 2 or higher, R63 values ​​are either the same or different. When r64 is 2 or higher, R64 values ​​are either the same or different. The term "substitution" here means substitution by one or more substituents selected from the group consisting of deuterium, halogen groups, cyano (-CN), silyl, C1-C10 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, and C2-C30 heterocyclic groups. The compounds mentioned above do not include the following compounds: 。 5. A compound having any one of the following structures: 。 6. An organic light-emitting device, characterized in that, include: The first electrode, the second electrode, and one or more organic layers disposed between the first electrode and the second electrode. One or more of the organic layers comprise the compound according to any one of claims 1 to 5.

7. The organic light-emitting device according to claim 6, wherein, The organic layer includes a light-emitting layer comprising a host and a dopant, wherein the host comprises one or more of the compounds described above.

8. The organic light-emitting device according to claim 7, wherein, The main body comprises a first anthracene derivative substituted with deuterium and a second anthracene derivative substituted with deuterium, wherein either the first anthracene derivative or the second anthracene derivative comprises the compound.

9. The organic light-emitting device according to claim 8, wherein, The first anthracene derivative substituted with deuterium comprises the compound.

10. The organic light-emitting device according to claim 7, wherein, The dopant is a fluorescent dopant.

11. The organic light-emitting device according to claim 7, wherein, The dopant comprises pyrene compounds or non-pyrene compounds.

12. The organic light-emitting device according to claim 11, wherein, The non-pyrene compounds include boron compounds.

13. The organic light-emitting device according to claim 7, wherein, The maximum emission peak λ of the luminescent layer containing the compound 最大 The range is from 400nm to 470nm.

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