Compounds and organic light emitting devices comprising the same

Abstract

The present specification relates to compounds of Chemical Formula 1 and organic light emitting devices comprising the same.

Description

Technical Field

[0001] This application claims priority and benefit to Korean Patent Application No. 10-2021-0116104, filed with the Korean Intellectual Property Office on September 1, 2021, the entire contents of which are incorporated herein by reference.

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

[0003] Organic light emission (OLED) typically refers to the conversion of electrical energy into light energy using organic materials. OLED devices generally have a structure comprising a positive electrode, a negative electrode, and an organic material layer between them. In many cases, the organic material layer can have a multilayer structure composed of different materials to improve the efficiency and stability of the OLED. The organic material layer can be composed of, for example, 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 from the positive electrode into the organic material layer, and electrons are injected from the negative electrode. When the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons return to the ground state.

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

[0005] Technical issues

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

[0007] Technical solution

[0008] An exemplary embodiment of this specification provides a compound represented by the following chemical formula 1.

[0009] [Chemical Formula 1]

[0010]

[0011] In chemical formula 1,

[0012] D stands for deuterium.

[0013] L1 is a direct bond; or a substituted or unsubstituted aryl group.

[0014] Ar1 is a substituted or unsubstituted aryl group.

[0015] R1 to R9 may be the same as or different from each other, and each is independently hydrogen; or deuterium, and

[0016] a1 is an integer from 1 to 8.

[0017] In addition, this specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer contain the compound.

[0018] Beneficial effects

[0019] The compounds described in this specification can be used as materials for organic material layers in organic light-emitting devices. Compounds according to another exemplary embodiment can improve efficiency, achieve low drive voltage, and / or improve lifetime characteristics in organic light-emitting devices. Attached Figure Description

[0020] Figure 1 and Figure 2 An example of an organic light-emitting device according to an exemplary embodiment of this specification is shown.

[0021] [Explanation of Figure Labels and Symbols]

[0022] 1: Base

[0023] 2: First electrode

[0024] 3: Second electrode

[0025] 4: Emissive layer

[0026] 5: First Hole Injection Layer

[0027] 6: Second cavity injection layer

[0028] 7: Hole transport layer

[0029] 8: Electron blocking layer

[0030] 9: First electron transport layer

[0031] 10: Second electron transport layer

[0032] 11: Electron Injection Layer Detailed Implementation

[0033] This instruction manual will be described in more detail below.

[0034] An exemplary embodiment of this specification provides a compound represented by chemical formula 1.

[0035] Because the anthracene of an exemplary embodiment according to this specification includes 1) Ar1 and 2) L1 bonded to the 3-position of benzobisbenzofuran as substituents at the anthracene core, and has a structure in which at least one hydrogen at the substituted position of the anthracene of formula 1 is deuterated, it possesses structural properties that improve electron and hole mobility and enhance molecular stability. Therefore, organic light-emitting devices incorporating this structure exhibit superior performance in terms of driving voltage, efficiency, and lifetime.

[0036] Examples of substituents in this specification will be described below, but are not limited thereto.

[0037] In this instruction manual, This refers to the part that needs to be connected.

[0038] Throughout this application, the term "combination thereof" included in the Markush type expression means a mixture or combination of one or more of the constituent elements described in the Markush type expression, and means to include one or more of the constituent elements described above.

[0039] The term “substitution” means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent, and there are no restrictions on the position to be substituted, as long as the position is where the hydrogen atom is substituted (i.e., the position where the substituent can be substituted), and when two or more are substituted, the two or more substituents can be the same or different from each other.

[0040] In this invention, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium; halogen group; hydroxyl group; cyano group; nitro group; alkyl group; cycloalkyl group; alkoxy group; alkenyl group; haloalkyl group; silyl group; boron group; amino group; aryl group; and heteroaryl group, substituted with a substituent connected to two or more of the exemplified substituents, or without substituents.

[0041] In this specification, the fact that two or more substituents are linked means that the hydrogen of any substituent is linked to another substituent. For example, when two substituents are linked to each other, phenyl and naphthyl groups can be linked to each other to become substituents. or Furthermore, the connection of three substituents not only includes the sequential connection of (substituent 1)-(substituent 2)-(substituent 3), but also the connection of (substituent 2) and (substituent 3) with (substituent 1). For example, phenyl, naphthyl, and isopropyl groups can be linked together to form substituents. , or The above limitations also apply to cases where four or more substituents are connected to each other.

[0042] Examples of halogen groups in this specification include fluorine, chlorine, bromine, or iodine.

[0043] In this specification, alkyl groups may be straight-chain or branched, and there is no particular limitation on the number of carbon atoms, but it is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0044] In this specification, there is no particular limitation on the cycloalkyl group, but it is preferably composed of 3 to 30 carbon atoms, and specific examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl, etc.

[0045] In this specification, the alkoxy group can be straight-chain, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 30. Specific examples include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc.

[0046] In this specification, the alkenyl group can be linear or branched, and its number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, etc. It includes, but is not limited to, styrene, etc.

[0047] In this specification, alkyl haloide means, in the definition of alkyl, that at least one halogen group is substituted for hydrogen in the alkyl group.

[0048] In this specification, there are no particular limitations on the aryl group, but it is preferred to have 6 to 30 carbon atoms, and the aryl group can be monocyclic or polycyclic.

[0049] When the aryl group is a monocyclic aryl group, there is no particular limitation on the number of carbon atoms, but it is preferably 6 to 30. Specific examples of monocyclic aryl groups include phenyl, biphenyl, terphenyl, etc., but are not limited to these.

[0050] When the aryl group is a polycyclic aryl group, there is no particular limitation on the number of carbon atoms, but it is preferably 10 to 30. Specific examples of polycyclic aryl groups include naphthyl, anthraceneyl, phenanthrene, phenylenetriene, pyrene, finadeninyl, etc. base, It includes, but is not limited to, methyl, fluorene, etc.

[0051] In this specification, the fluorene group may be substituted, and adjacent groups may be bonded to each other to form a ring.

[0052] Examples of fluorene groups that have undergone substitution include: , , , , , , , And so on, but not limited to these.

[0053] In this specification, "adjacent" groups may mean a substituent that substitutes for an atom directly bonded to the atom substituted by the corresponding substituent, a substituent that is spatially closest to the corresponding substituent, or another substituent that substitutes for the atom substituted by the corresponding substituent. For example, two substituents in an ortho position of a benzene ring and two substituents in an aliphatic ring that substitute for the same carbon atom can be interpreted as groups that are "adjacent" to each other.

[0054] In this specification, a heteroaryl group comprises one or more atoms other than carbon, i.e., one or more heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from O, N, Se, S, etc. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thiophene, furanyl, pyrrole, imidazolyl, thiazolyl, etc. azole group, Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazenopyrazinyl, isoquinolinyl, indoleyl, carbazoleyl, benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthridine, phenanthrolinyl, iso Azolyl, thiadiazolyl, dibenzofuranyl, dibenzothiopyrrolyl, phen Thiol, phen Azinyl, phenothiazinyl, dihydroindocarbazolyl, spirofluorene Examples include, but are not limited to, ton-based, spirofluorene-thion-based, etc.

[0055] In this specification, silane can be alkylsilane, arylsilane, heteroarylsilane, etc. The above examples of alkyl can be applied to alkyl in alkylsilane, the above examples of aryl can be applied to aryl in arylsilane, and the examples of heteroaryl can be applied to heteroaryl in heteroarylsilane.

[0056] In this specification, the boron group can be -BR 100 R 101 R 100 and R 101 They may be the same as or different from each other, and may be independently selected from hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted monocyclic or polycyclic cycloalkyl groups having 3 to 30 carbon atoms; substituted or unsubstituted straight-chain or branched alkyl groups having 1 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms. Specific examples of boryl groups include, but are not limited to, dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl, etc.

[0057] In this specification, the amino group may be selected from -NH2, alkylamino, N-alkylarylamino, arylamino, N-arylheteroarylamino, N-alkylheteroarylamino, and heteroarylamino, and its number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amino groups include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthraceneamino, 9-methyl-anthraylamino, diphenylamino, xylylamino, N-phenyltolylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthreneamino, N-biphenylphenanthreneamino, N-phenylfluorenylamino, N-phenyltriphenylamino, N-phenanthrenefluorenylamino, N-biphenylfluorenylamino, etc., but are not limited thereto.

[0058] In this specification, N-alkylarylamine means that the N of the amino group is replaced by an alkyl or aryl amino group. The alkyl and aryl groups in N-alkylarylamine are the same as those in the examples of alkyl and aryl groups described above.

[0059] In this specification, N-arylheteroarylamine means that the N of the amino group is replaced by an aryl or heteroaryl amino group. The aryl and heteroaryl groups in N-arylheteroarylamine are the same as those in the examples of aryl and heteroaryl groups described above.

[0060] In this specification, N-alkylheteroarylamine means that the N of the amino group is replaced by an alkyl or heteroaryl amino group. The alkyl and heteroaryl groups in N-alkylheteroarylamine are the same as those in the examples of alkyl and heteroaryl groups described above.

[0061] In this specification, examples of alkylamine groups include substituted or unsubstituted monoalkylamine groups or substituted or unsubstituted dialkylamine groups. The alkyl group in an alkylamine group can be a straight-chain or branched alkyl group. An alkylamine group containing two or more alkyl groups can contain a straight-chain alkyl group, a branched alkyl group, or both a straight-chain alkyl group and a branched alkyl group. For example, the alkyl group in an alkylamine group can be selected from the above-described examples of alkyl groups.

[0062] In this specification, examples of arylamines include substituted or unsubstituted monoarylamines or substituted or unsubstituted diarylamines. The aryl group in an arylamine can be a monocyclic aryl or a polycyclic aryl. An arylamine containing two or more aryl groups can comprise a monocyclic aryl, a polycyclic aryl, or both. For example, the aryl group in an arylamine can be selected from the above-described examples of aryl groups.

[0063] In this specification, examples of heteroarylamines include substituted or unsubstituted mono-heteroarylamines or substituted or unsubstituted di-heteroarylamines. Heteroarylamines comprising two or more heteroaryl groups may include monocyclic heteroaryl, polycyclic heteroaryl, or both. For example, the heteroaryl groups in a heteroarylamine may be selected from the aforementioned examples of heteroaryl groups.

[0064] In this specification, arylene refers to a group having two bonding positions within an aryl group, i.e., a divalent group. The above description of aryl groups can be applied to arylene groups, the difference being that each arylene group is a divalent group.

[0065] In this specification, “deuterated” or “deuterated” means that hydrogen at a substituted position in a compound is replaced by deuterium.

[0066] In this specification, "over-deuterated" means a compound or group in which all hydrogen atoms in the molecule are replaced by deuterium, and has the same meaning as "100% deuterated".

[0067] In this specification, "X% deuterated", "X% degree of deuteration", or "X% rate of deuteration substitution" means that X% of the hydrogens at the substituted positions in the corresponding structure are deuterated. For example, when the corresponding structure is dibenzofuran, a dibenzofuran that is "25% deuterated", "25% degree of deuteration", or "25% rate of deuteration" means that two of the eight hydrogens at the substituted positions in the dibenzofuran are deuterated.

[0068] In this specification, the degree of deuteration can be determined by known methods such as nuclear magnetic resonance spectroscopy (NMR spectroscopy). 1 It is determined by ¹H NMR, thin-layer chromatography / mass spectrometry (TLC / MS), or matrix-assisted laser desorption / ionization time-of-flight mass spectrometry (MALDI-TOF MS).

[0069] Unless otherwise specified in this specification, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. While similar or equivalent methods and materials to those described herein may be used in practice or in testing of exemplary embodiments of the invention, suitable methods and materials will be described below. All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference in their entirety, and in the event of conflict, this specification (including definitions) shall prevail unless a specific paragraph is cited. Furthermore, materials, methods, and examples are illustrative only and are not intended to be restrictive.

[0070] According to an exemplary embodiment of this specification, chemical formula 1 is represented by the following chemical formula 1-1 or 1-2.

[0071] [Chemical Formula 1-1]

[0072]

[0073] [Chemical Formula 1-2]

[0074]

[0075] In chemical formulas 1-1 and 1-2,

[0076] The definitions of D, Ar1, a1, and R1 through R9 are the same as those defined in Formula 1, and

[0077] L11 is a substituted or unsubstituted aryl group.

[0078] According to an exemplary embodiment of this specification, chemical formula 1 is represented by the following chemical formulas 1-3 or 1-4.

[0079] [Chemical Formulas 1-3]

[0080]

[0081] [Chemical Formulas 1-4]

[0082]

[0083] In chemical formulas 1-3 and 1-4,

[0084] The definitions of D, Ar1, a1, and R1 through R9 are the same as those defined in Formula 1.

[0085] a2 is an integer from 0 to 4.

[0086] a3 is an integer from 0 to 4.

[0087] a4 is an integer from 0 to 4, and

[0088] 0≤a3+a4≤6.

[0089] According to one embodiment of the specification, the 0 in the definition of a2 to a4 refers to bonded hydrogen rather than deuterium.

[0090] According to one exemplary embodiment of this specification, a2 is an integer from 1 to 4.

[0091] According to one exemplary embodiment of this specification, a2 is 0.

[0092] According to one exemplary embodiment of this specification, a2 is 1.

[0093] According to one exemplary embodiment of this specification, a2 is 2.

[0094] According to one exemplary embodiment of this specification, a2 is 3.

[0095] According to one exemplary embodiment of this specification, a2 is 4.

[0096] According to one exemplary embodiment of this specification, a3 is an integer from 1 to 4.

[0097] According to one exemplary embodiment of this specification, a3 is 0.

[0098] According to one exemplary embodiment of this specification, a3 is 1.

[0099] According to one exemplary embodiment of this specification, a3 is 2.

[0100] According to one exemplary embodiment of this specification, a3 is 3.

[0101] According to one exemplary embodiment of this specification, a3 is 4.

[0102] According to one exemplary embodiment of this specification, a4 is an integer from 1 to 4.

[0103] According to one exemplary embodiment of this specification, a4 is 0.

[0104] According to one exemplary embodiment of this specification, a4 is 1.

[0105] According to one exemplary embodiment of this specification, a4 is 2.

[0106] According to one exemplary embodiment of this specification, a4 is 3.

[0107] According to one exemplary embodiment of this specification, a4 is 4.

[0108] According to one exemplary embodiment of this specification, a1 is 1.

[0109] According to one exemplary embodiment of this specification, a1 is 2.

[0110] According to one exemplary embodiment of this specification, a1 is 3.

[0111] According to one exemplary embodiment of this specification, a1 is 4.

[0112] According to one exemplary embodiment of this specification, a1 is 5.

[0113] According to one exemplary embodiment of this specification, a1 is 6.

[0114] According to one exemplary embodiment of this specification, a1 is 7.

[0115] According to one exemplary embodiment of this specification, a1 is 8.

[0116] According to an exemplary embodiment of this specification, at least one of R1 to R9 is deuterium, and the remainder is hydrogen.

[0117] According to an exemplary embodiment of this specification, one of R1 to R9 is deuterium, and the remainder is hydrogen.

[0118] According to an exemplary embodiment of this specification, two of R1 to R9 are deuterium, and the remainder is hydrogen.

[0119] According to an exemplary embodiment of this specification, three of R1 to R9 are deuterium, and the remainder is hydrogen.

[0120] According to an exemplary embodiment of this specification, four of R1 to R9 are deuterium, and the remainder is hydrogen.

[0121] According to an exemplary embodiment of this specification, five of R1 to R9 are deuterium, and the remainder is hydrogen.

[0122] According to an exemplary embodiment of this specification, six of R1 to R9 are deuterium, and the remainder is hydrogen.

[0123] According to an exemplary embodiment of this specification, seven of R1 to R9 are deuterium, and the remainder is hydrogen.

[0124] According to an exemplary embodiment of this specification, eight of R1 to R9 are deuterium, and the remainder are hydrogen.

[0125] According to an exemplary embodiment of this specification, R1 to R9 are deuterium.

[0126] According to one exemplary embodiment of this specification, R1 to R9 are hydrogen.

[0127] According to an exemplary embodiment of this specification, L1 is a direct bond; or an unsubstituted or deuterated monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and Ar1 is an unsubstituted or deuterated monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted with one or more substituents in combinations thereof.

[0128] According to one exemplary embodiment of this specification, L1 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0129] According to an exemplary embodiment of this specification, L1 is a direct bond; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, substituted or unsubstituted.

[0130] According to an exemplary embodiment of this specification, L1 is a direct bond; or an unsubstituted or deuterated monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0131] According to one exemplary embodiment of this specification, L1 is a direct bond; or an unsubstituted or deuterated monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0132] According to an exemplary embodiment of this specification, L1 is a direct bond; an unsubstituted or deuterated phenylene; or an unsubstituted or deuterated naphthylene.

[0133] According to an exemplary embodiment of this specification, Ar1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0134] According to an exemplary embodiment of this specification, Ar1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0135] According to an exemplary embodiment of this specification, Ar1 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or deuterated and substituted with one or more substituents of combinations thereof.

[0136] According to an exemplary embodiment of this specification, Ar1 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that is unsubstituted or deuterated and substituted with one or more substituents of combinations thereof.

[0137] According to an exemplary embodiment of this specification, Ar1 is an unsubstituted or substituted phenyl group, or a phenyl group substituted with one or more of the following: deuterium, naphthyl, or combinations thereof; an unsubstituted or deuterium-substituted biphenyl group; or an unsubstituted or deuterium-substituted naphthyl group.

[0138] According to one exemplary embodiment of this specification, chemical formula 1 is selected from any of the following compounds.

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154] .

[0155] This specification provides organic light-emitting devices containing the above-described compounds.

[0156] In this specification, when a component is positioned "on" another component, this includes not only the case where one component is in contact with another component, but also the case where there is another component between the two components.

[0157] In this specification, when a part "includes" a constituent element, unless otherwise specifically described, this does not mean that other constituent elements are excluded, but rather that other constituent elements may be included.

[0158] In this specification, the term "layer" has the same meaning as "film" as commonly used in the art, and refers to a coating covering a target area. There is no limitation on the size of a "layer," and individual "layers" may have the same or different sizes. According to one exemplary embodiment, the size of a "layer" may be the same as the size of the entire device, may correspond to the size of a specific functional area, and may be as small as a single subpixel.

[0159] In this specification, when a particular material A is contained in layer B, this means the following two situations: i) the fact that one or more materials A are contained in one layer B; and ii) the fact that layer B consists of one or more layers, and material A is contained in one or more layers of multiple layers B.

[0160] In this specification, when a particular material A is contained in layer C or layer D, this means all of the following: i) the fact that material A is contained in one or more layers of layer C having one or more layers; ii) the fact that material A is contained in one or more layers of layer D having one or more layers; and iii) the fact that material A is contained in each of layer C having one or more layers and layer D having one or more layers.

[0161] This specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer contain a compound represented by chemical formula 1.

[0162] The organic material layer of the organic light-emitting device described in this specification can be a single-layer structure, or it can be a multilayer structure in which two or more organic material layers are stacked. For example, the organic material layer can have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc. However, the structure of the organic light-emitting device is not limited to this, and it can include a smaller number of organic material layers.

[0163] According to an exemplary embodiment of this specification, the organic material layer includes a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, hole transport layer, or electron blocking layer contains the compound.

[0164] According to one exemplary embodiment of this specification, the organic material layer includes a light-emitting layer, and the light-emitting layer contains the compound.

[0165] According to an exemplary embodiment of this specification, the organic material layer includes a light-emitting layer, and the light-emitting layer contains the compound as the body of the light-emitting layer.

[0166] According to one exemplary embodiment of this specification, the light-emitting layer includes a dopant, and the dopant includes one or more selected from fluorescent dopant, phosphorescent dopant, and thermally delayed fluorescent dopant.

[0167] According to one exemplary embodiment of this specification, the fluorescent dopant includes one or more compounds selected from arylamine-based compounds and boron-based compounds.

[0168] According to one exemplary embodiment of this specification, the fluorescent dopant is an arylamine-based compound.

[0169] According to one exemplary embodiment of this specification, the fluorescent dopant is a boron-based compound.

[0170] According to an exemplary embodiment of this specification, the organic material layer includes a light-emitting layer comprising a host and a dopant, the host comprising the compound, and the dopant comprising one or more selected from fluorescent dopant, phosphorescent dopant, and thermally delayed fluorescent dopant.

[0171] According to an exemplary embodiment of this specification, the arylamine-based compound is represented by the following chemical formula D-1.

[0172] [Chemical Formula D-1]

[0173]

[0174] In chemical formula D-1,

[0175] L101 and L102 may be identical or different from each other, and each is independently a direct bond; or a substituted or unsubstituted aryl group, and

[0176] Ar101 to Ar104 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 heteroaryl group.

[0177] According to an exemplary embodiment of this specification, L101 and L102 are direct keys.

[0178] According to an exemplary embodiment of this specification, Ar101 to Ar104 may be the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0179] According to an exemplary embodiment of this specification, Ar101 to Ar104 may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0180] According to one exemplary embodiment of this specification, Ar101 to Ar104 may be the same as or different from each other, and each is independently a methyl-substituted phenyl; or a dibenzofuranyl.

[0181] According to an exemplary embodiment of this specification, chemical formula D-1 is represented by the following compound.

[0182]

[0183] According to one exemplary embodiment of this specification, the boron-based compound is represented by the following chemical formula D-2.

[0184] [Chemical formula D-2]

[0185]

[0186] In chemical formula D-2,

[0187] T1 to T5 may be the same as or different from each other, and each is independently hydrogen; substituted or unsubstituted alkyl groups; substituted or unsubstituted amino groups; or substituted or unsubstituted aryl groups.

[0188] t3 and t4 are each integers from 1 to 4.

[0189] t5 is an integer from 1 to 3.

[0190] When t3 is 2 or greater, two or more T3s are either the same or different from each other.

[0191] When t4 is 2 or greater, two or more T4s are the same or different from each other, and

[0192] When t5 is 2 or greater, two or more T5s are the same or different from each other.

[0193] According to an exemplary embodiment of this specification, T1 to T5 may be the same as or different from each other, and each is independently hydrogen; a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0194] According to an exemplary embodiment of this specification, T1 to T5 may be the same as or different from each other, and each is independently hydrogen; a straight-chain or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms.

[0195] According to one exemplary embodiment of this specification, T1 to T5 may be the same as or different from each other, and each is independently hydrogen; tert-butyl; diphenylamino; or unsubstituted or tert-butyl-substituted phenyl.

[0196] According to one exemplary embodiment of this specification, chemical formula D-2 is represented by the following compound.

[0197]

[0198] According to one exemplary embodiment of this specification, those known in the art are used as phosphorescent dopants and thermally delayed fluorescence dopants, but phosphorescent dopants and thermally delayed fluorescence dopants are not limited thereto.

[0199] According to one exemplary embodiment of this specification, the light-emitting layer comprises a host and a dopant in a weight ratio of 99:1 to 1:99. Specifically, the light-emitting layer comprises a host and a dopant in a weight ratio of 99:1 to 50:50, and more specifically, in a weight ratio of 99:1 to 95:5.

[0200] According to an exemplary embodiment of this specification, the organic light-emitting device further includes one or more layers selected from a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.

[0201] According to an exemplary embodiment of this specification, the organic light-emitting device includes: a first electrode; a second electrode; a light-emitting layer disposed between the first electrode and the second electrode; and an organic material layer having two or more layers disposed between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode.

[0202] According to an exemplary embodiment of this specification, an organic material layer having two or more layers between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode may be selected from a light-emitting layer, a hole transport layer, a hole injection layer, a hole injection and transport layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer.

[0203] According to an exemplary embodiment of this specification, a hole injection layer having two or more layers is included between the light-emitting layer and the first electrode. The hole injection layer having two or more layers may contain the same or different materials.

[0204] According to an exemplary embodiment of this specification, a hole transport layer having two or more layers is included between the light-emitting layer and the first electrode. The hole transport layer having two or more layers may contain the same or different materials.

[0205] According to an exemplary embodiment of this specification, an electron transport layer having two or more layers is included between the light-emitting layer and the second electrode. The electron transport layer having two or more layers may contain the same or different materials.

[0206] According to one exemplary embodiment of this specification, the first electrode is an anode or a cathode.

[0207] According to one exemplary embodiment of this specification, the second electrode is a cathode or an anode.

[0208] According to an exemplary embodiment of this specification, an organic light-emitting device can be a normal type of organic light-emitting device in which an anode, an organic material layer having one or more layers, and a cathode are sequentially stacked on a substrate.

[0209] According to an exemplary embodiment of this specification, an organic light-emitting device can be an inverted organic light-emitting device in which a cathode, an organic material layer having one or more layers, and an anode are sequentially stacked on a substrate.

[0210] For example, Figure 1 and Figure 2 The structure of an organic light-emitting device according to an exemplary embodiment of this specification is illustrated below. Figure 1 and Figure 2 Organic light-emitting devices are illustrated, but organic light-emitting devices are not limited to these.

[0211] Figure 1 An example is shown of an organic light-emitting device in which a first electrode 2, a light-emitting layer 4, and a second electrode 3 are sequentially stacked on a substrate 1. A compound of formula 1 is contained in the light-emitting layer 4.

[0212] Figure 2 An example is illustrated of an organic light-emitting device in which a substrate 1, a first electrode 2, a first hole injection layer 5, a second hole injection layer 6, a hole transport layer 7, an electron blocking layer 8, a light-emitting layer 4, a first electron transport layer 9, a second electron transport layer 10, an electron injection layer 11, and a second electrode 3 are sequentially stacked. In the above structure, the compound may be contained in the light-emitting layer 4.

[0213] The organic light-emitting device described in this specification can be manufactured using materials and methods known in the art, except that the light-emitting layer contains the compound described herein, i.e., the compound represented by chemical formula 1.

[0214] When an organic light-emitting device comprises multiple layers of organic materials, the organic material layers can be formed from the same material or different materials.

[0215] For example, the organic light-emitting device of this specification can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light-emitting device can be manufactured by depositing a metal, or a conductive metal oxide, or an alloy thereof, on the substrate using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation to form an anode; forming an organic material layer on the anode comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer; and then depositing a material that can be used as a cathode on the organic material layer. In addition to the above methods, the organic light-emitting device can also be manufactured by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate.

[0216] Furthermore, in the manufacture of organic light-emitting devices, the compound represented by chemical formula 1 can be formed into an organic material layer not only by vacuum deposition but also by solution application. Here, solution application refers to, but is not limited to, spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, and roll coating.

[0217] In addition to the methods described above, organic light-emitting devices can also be fabricated by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate. However, the fabrication method is not limited to these methods.

[0218] As the first electrode material, materials with high work functions are generally preferred to facilitate hole injection into the organic material layer. Examples include: metals, such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline; and so on, but are not limited thereto.

[0219] As a second electrode material, materials with low work functions are generally preferred to facilitate electron injection into the organic material layer. Examples include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF / Al or LiO2 / Al; and so on, but are not limited to these.

[0220] The luminescent layer may comprise a host material and a dopant material. When an additional luminescent layer is included in addition to the luminescent layer comprising a compound represented by Formula 1 according to an exemplary embodiment of this specification, examples of the host material include fused and / or non-fused aromatic ring derivatives, heterocyclic compounds, etc. Specific examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and specific examples of heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited to these examples.

[0221] Examples of dopant materials include aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are fused aromatic ring derivatives having substituted or unsubstituted aryl amine groups, and examples include pyrene, anthracene, etc., having aryl amine groups. Examples include diindene pyrene, etc. Furthermore, styrene amine compounds are compounds in which at least one aryl vinyl group is substituted with a substituted or unsubstituted aryl amine, and one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamine groups are substituted or unsubstituted. Specific examples include, but are not limited to, styrene amine, styrene diamine, styrene triamine, styrene tetraamine, etc. Furthermore, examples of metal complexes include, but are not limited to, iridium complexes, platinum complexes, etc.

[0222] The hole injection layer is a layer that receives holes from the electrode. Preferably, the hole injection material has the ability to transport holes and has the effect of receiving holes from the anode, as well as an excellent hole injection effect on the light-emitting layer or light-emitting material. Furthermore, the hole injection material is preferably a material that excels in preventing excitons generated by the light-emitting layer from migrating to the electron injection layer or electron injection material. Furthermore, the hole injection material is preferably a material that excels in the ability to form thin films. Furthermore, the highest occupied molecular orbital (HOMO) of the hole injection material is preferably a value between the work function of the anode material and the HOMO of the adjacent organic material layer. Specific examples of hole injection materials include: metalloporphyrins, oligothiophenes, and arylamine-based organic materials; organic materials based on hexanitrile hexaazabenzophenanthrene; organic materials based on quinacridones; and organic materials based on... Organic materials; conductive polymers based on polythiophene, such as anthraquinone and polyaniline; and so on, but not limited to these.

[0223] According to one exemplary embodiment of this specification, the hole injection layer comprises a compound represented by the chemical formula HI-1, but is not limited thereto.

[0224] [Chemical formula HI-1]

[0225]

[0226] In the chemical formula HI-1,

[0227] R300 to R308 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 bonded to an adjacent group to form a substituted or unsubstituted ring.

[0228] r301 and r302 are each integers from 1 to 4.

[0229] r303 and r304 are each integers from 1 to 3.

[0230] When r301 is 2 or greater, R301 may be the same or different from each other.

[0231] When r302 is 2 or greater, R302 may be the same or different from each other.

[0232] When r303 is 2 or greater, R303 may be the same or different from each other, and

[0233] When r304 is 2 or greater, R304 can be the same or different from each other.

[0234] According to one exemplary embodiment of this specification, R301 to R304 are hydrogen.

[0235] According to one exemplary embodiment of this specification, R300 is a substituted or unsubstituted aryl group.

[0236] According to one exemplary embodiment of this specification, R300 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0237] According to one exemplary embodiment of this specification, R300 is phenyl.

[0238] According to one exemplary embodiment of this specification, R300 is bonded to R301 or R302 to form a substituted or unsubstituted ring.

[0239] According to one exemplary embodiment of this specification, R300 is bonded to R301 or R302 to form an indole ring.

[0240] According to an exemplary embodiment of this specification, R305 to R308 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 heteroaryl group.

[0241] According to an exemplary embodiment of this specification, R305 to R308 may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms that is unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0242] According to one exemplary embodiment of this specification, R305 to R308 may be the same as or different from each other, and each is independently phenyl; or unsubstituted or phenyl-substituted carbazole group.

[0243] According to an exemplary embodiment of this specification, the chemical formula HI-1 is represented by the following compound.

[0244]

[0245] According to one exemplary embodiment of this specification, the hole injection layer comprises a compound represented by the chemical formula HI-2, but is not limited thereto.

[0246] [Chemical formula HI-2]

[0247]

[0248] In the chemical formula HI-2,

[0249] At least one of X'1 to X'6 is N, and the rest are CH, and

[0250] 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 bonded to an adjacent group to form a substituted or unsubstituted ring.

[0251] According to an exemplary embodiment of this specification, X'1 to X'6 are N.

[0252] According to an exemplary embodiment of this specification, R309 to R314 are cyano groups.

[0253] According to one exemplary embodiment of this specification, the chemical formula HI-2 is represented by the following compound.

[0254]

[0255] The 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 preferably a material with high hole mobility that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0256] According to one exemplary embodiment of this specification, the hole transport layer comprises, but is not limited to, a compound represented by the chemical formula HT-1.

[0257] [Chemical formula HT-1]

[0258]

[0259] In the chemical formula HT-1,

[0260] R315 to R317 may be the same as or different from each other, and each is independently selected from hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; and combinations thereof, or bonded to adjacent groups to form substituted or unsubstituted rings.

[0261] r315 is an integer from 1 to 5, and when r315 is 2 or greater, two or more R315s are the same or different from each other.

[0262] r316 is an integer from 1 to 5, and when r316 is 2 or greater, two or more R316 are the same or different from each other.

[0263] According to an exemplary embodiment of this specification, R317 is selected from any of the following: substituted or unsubstituted aryl groups; substituted or unsubstituted heteroaryl groups; and combinations thereof.

[0264] According to an exemplary embodiment of this specification, R317 is selected from carbazolyl; phenyl; biphenyl; and combinations thereof.

[0265] According to an exemplary embodiment of this specification, R315 and R316 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group, or bonded to an adjacent group to form an alkyl-substituted aromatic ring.

[0266] According to one exemplary embodiment of this specification, R315 and R316 may be the same as or different from each other, and each is independently phenyl, or bonded to adjacent groups to form methyl-substituted indene.

[0267] According to an exemplary embodiment of this specification, the chemical formula HT-1 is represented by any of the following compounds.

[0268]

[0269] The electron transport layer is the layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is preferably a material with high electron mobility that can effectively receive electrons from the cathode and transfer them to the light-emitting layer. Specific examples include: Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavonoid-metal complexes; and so on, but are not limited to these. The electron transport layer can be used with any desired cathode material as used according to the relevant art. In particular, suitable cathode materials are typically materials with low work functions, followed by an aluminum or silver layer. Specific examples include cesium, barium, calcium, ytterbium, and samarium, in each case followed by an aluminum or silver layer.

[0270] According to one exemplary embodiment of this specification, the electron transport layer comprises a compound represented by the following chemical formula ET-1.

[0271] [Chemical formula ET-1]

[0272]

[0273] In the chemical formula ET-1,

[0274] At least one of X'7 to X'8 is N, and the rest are CH.

[0275] R318 to R323 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 bonded to an adjacent group to form a substituted or unsubstituted ring.

[0276] L'1 is a direct bond; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0277] r322 is an integer from 1 to 7, and when r322 is 2 or greater, R322 is either the same or different from each other.

[0278] l'1 is an integer from 1 to 5, and when l'1 is 2 or greater, L'1 is either the same or different from each other.

[0279] According to an exemplary embodiment of this specification, R318 to R323 may be the same as or different from each other, and each is independently hydrogen; or substituted or unsubstituted aryl groups, or adjacent groups are bonded to each other to form substituted or unsubstituted aromatic hydrocarbon rings.

[0280] According to an exemplary embodiment of this specification, R318 to R323 may be the same as or different from each other, and each is independently hydrogen; phenyl; or naphthyl, or adjacent groups are bonded to each other to form benzene.

[0281] According to one exemplary embodiment of this specification, L'1 is a substituted or unsubstituted aryl group.

[0282] According to one exemplary embodiment of this specification, L'1 is phenylene.

[0283] According to one exemplary embodiment of this specification, ET-1 is represented by the following compound.

[0284]

[0285] According to one exemplary embodiment of this specification, the electron transport layer comprises a compound represented by the following chemical formula ET-2.

[0286] [Chemical formula ET-2]

[0287]

[0288] In the chemical formula ET-2,

[0289] T7 to T9 may be the same as or different from each other, and each is independently selected from hydrogen; deuterium; cyano; substituted or unsubstituted alkyl; substituted or unsubstituted amino; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; and combinations thereof, or bonded to adjacent groups to form substituted or unsubstituted rings.

[0290] t7 is an integer from 1 to 4, and when t7 is 2 or greater, two or more T7s are either the same or different from each other.

[0291] t8 is an integer from 1 to 4, and when t8 is 2 or greater, two or more T8s are either the same or different from each other.

[0292] t9 is an integer from 1 to 10, and when t9 is 2 or greater, two or more T9s are the same or different from each other.

[0293] According to an exemplary embodiment of this specification, T7 to T9 may be the same as or different from each other, and each independently is selected from hydrogen; substituted or unsubstituted aryl; and substituted or unsubstituted heteroaryl and combinations thereof.

[0294] According to an exemplary embodiment of this specification, T7 to T9 may be the same as or different from each other, and each independently is selected from hydrogen; carbazolyl; phenyl; biphenyl; triazine; and combinations thereof.

[0295] According to one exemplary embodiment of this specification, ET-2 is represented by the following compound.

[0296]

[0297] The electron transport layer may also contain a metal complex. As the metal, metals used in the art can be used.

[0298] The electron injection layer is a layer that receives electrons from the electrodes. Preferably, the electron injection material exhibits excellent electron transport capabilities and has the effect of receiving electrons from the cathode, as well as excellent electron injection effects on the light-emitting layer or light-emitting material. Furthermore, the electron injection material is preferably a material that prevents excitons generated by the light-emitting layer from migrating to the hole injection layer and has excellent thin film formation capabilities. Specific examples include: fluorenone, anthraquinone dimethane, biphenylquinone, thiamethoxam dioxide, etc. azole, diazole, triazole, imidazole Tetracarboxylic acids, fluorenemethane, anthrone, and their derivatives; metal complexes; nitrogen-containing 5-membered ring derivatives; and so on, but not limited to these.

[0299] Examples of metal complex compounds include, but are not limited to, 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)chlorogallium, 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.

[0300] An electron blocking layer is a layer that improves the lifespan and efficiency of a device by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer. Known materials can be used without restriction as the electron blocking layer, and the electron blocking layer can be formed between the light-emitting layer and the hole injection layer, between the light-emitting layer and the hole transport layer, or between the light-emitting layer and a layer that simultaneously injects and transports holes.

[0301] A hole-blocking layer is a layer that prevents holes from reaching the cathode, and it can typically be formed under the same conditions as the electron-injection layer. Specific examples include... Diazole or triazole derivatives, phenanthrene-rhein derivatives, aluminum complexes, etc., but not limited to these.

[0302] Depending on the material to be used, the organic light-emitting device according to this specification can be a top-emitting, bottom-emitting, or dual-emitting type.

[0303] The organic light-emitting devices according to this specification can be included in and used in various electronic devices. For example, electronic devices can be display panels, touch panels, solar modules, light-emitting devices, etc., and are not limited thereto.

[0304] Invention Embodiments

[0305] In the following description, this specification will be described in detail with reference to embodiments, comparative examples, etc., used to specifically describe this specification. However, modifications can be made in various forms based on the embodiments and comparative examples in this specification, and should not be construed as limiting the scope of this specification to the embodiments and comparative examples described in detail below. The embodiments and comparative examples in this specification are provided to illustrate this specification more completely to those skilled in the art.

[0306] Synthesis Example 1. Synthesis of Nucleus-1

[0307]

[0308] Preparation of compound nucleus-1 (<1-a>)

[0309] 3-Chloro-benzo[1,2-b:4,3-b']bisbenzofuran (50 g, 170.81 mmol), bis(pinacol)diboron (54.3 g, 256.22 mmol), tricyclohexylphosphine (1.9 g, 6.7 mmol), potassium acetate (33.5 g, 341.6 mmol), and Pd(dba)2 (1.9 g, 3.4 mmol) were added to 1,4-bisbenzofuran. The mixture was placed in alkyl (400 ml) and the resulting solution was refluxed for 6 hours. The reaction solution was cooled, and the organic layer was extracted with ethyl acetate and then dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure, and the residue was purified by column chromatography to obtain compound nucleus-1 (44.0 g, 67% yield).

[0310] MS: [M+H]+=385

[0311] Synthesis Example 2. Synthesis of Nucleus-2

[0312]

[0313] Preparation of <2-a> compound core-2-a

[0314] After dissolving compound nucleus-1 (40 g, 104.1 mmol) and 1-bromo-3-chlorobenzene (18.9 g, 98.9 mmol) in THF (400 ml), Pd(PPh3)4 (1.2 g, 1.0 mmol) and 80 ml of 2M K2CO3 aqueous solution were added, and the resulting solution was refluxed for 4 hours. The reaction solution was cooled, and the organic layer was extracted with ethyl acetate and then dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure, and the residue was purified by column chromatography to obtain compound nucleus-2-a (23.7 g, 65% yield).

[0315] MS: [M+H]+=369

[0316] <2-b>Preparation of compound nucleus-2

[0317] Compound core-2 was obtained by synthesis and purification in the same manner as in the preparation of compound core-1 of <1-a> in Synthesis Example 1, except that compound core-2-a was used instead of 3-chloro-benzo[1,2-b:4,3-b']bisbenzofuran in the preparation of compound core-1 of <1-a> in Synthesis Example 1.

[0318] MS: [M+H]+=461

[0319] Synthesis Example 3. Synthesis of Nucleo-3

[0320]

[0321] Preparation of <3-a> compound core-3-a

[0322] Compound core-3-a was obtained by synthesis and purification in the same manner as in the preparation of <2-a> compound core-2-a in Synthetic Example 2, except that 1-bromo-4-chlorobenzene was used instead of 1-bromo-3-chlorobenzene in the preparation of <2-a> compound core-2-a in Synthetic Example 2.

[0323] MS: [M+H]+=369

[0324] <3-b>Preparation of compound nucleus-3

[0325] Compound nucleus-3 was obtained by synthesis and purification in the same manner as in the preparation of compound nucleus-1 of <1-a> in Synthesis Example 1, except that compound nucleus-3-a was used instead of 3-chloro-benzo[1,2-b:4,3-b']bisbenzofuran in the preparation of compound nucleus-1 of <1-a> in Synthesis Example 1.

[0326] MS: [M+H]+=461

[0327] Synthesis Example 4. Synthesis of Nucleo-4

[0328]

[0329] Preparation of <4-a> compound core-4-a

[0330] Compound core-4-a was obtained by synthesis and purification in the same manner as in the preparation of <2-a> compound core-2-a in Synthetic Example 2, except that 1-bromo-6-chloronaphthalene was used instead of 1-bromo-3-chlorobenzene in the preparation of <2-a> compound core-2-a in Synthetic Example 2.

[0331] MS: [M+H]+=419

[0332] <4-b>Preparation of compound nucleus-4

[0333] Compound core-4 was obtained by synthesis and purification in the same manner as in the preparation of compound core-1 of <1-a> in Synthesis Example 1, except that compound core-4-a was used instead of 3-chloro-benzo[1,2-b:4,3-b']bisbenzofuran in the preparation of compound core-1 of <1-a> in Synthesis Example 1.

[0334] MS: [M+H]+=511

[0335] Synthesis Example 5. Synthesis of BH-1

[0336]

[0337] <5-a> Preparation of compound BH-1

[0338] Compound BH-1 was obtained by synthesis and purification in the same manner as in the preparation of compound core-2-a of Synthetic Example 2, except that 1-bromo-3-chlorobenzene was used instead of 9-bromo-10-phenylanthracene-1,2,3,4,5,6,7,8-d8 in the preparation of compound core-2-a of Synthetic Example 2.

[0339] MS: [M+H]+=519

[0340] Synthesis Example 6. Synthesis of BH-2

[0341]

[0342] Preparation of compound BH-2 (<6-a>)

[0343] Compound BH-2 was obtained by synthesis and purification in the same manner as in the preparation of <2-a> compound core-2-a in Synthetic Example 2, except that 9-bromo-10-(naphth-1-yl)anthracene-1,2,3,4,5,6,7,8-d8 was used instead of 1-bromo-3-chlorobenzene, and compound core-2 was used instead of compound core-1.

[0344] MS: [M+H]+=645

[0345] Synthesis Example 7. Synthesis of BH-3

[0346]

[0347] Preparation of compound BH-3-a (<7-a>)

[0348] Compound BH-3-a was obtained by synthesis and purification in the same manner as in the preparation of compound nucleus-2-a of Synthetic Example 2, except that 9-bromoanthracene was used instead of 1-bromo-3-chlorobenzene in the preparation of compound nucleus-2-a of Synthetic Example 2.

[0349] MS: [M+H]+=435

[0350] Preparation of compound BH-3-b (<7-b>)

[0351] Compound BH-3-a (40 g, 92.1 mmol) and AlCl3 (8 g, 60 mmol) were added to C6D6 (800 ml), and the resulting solution was stirred for 5 hours. After the reaction was complete, D2O (50 ml) was added, and the resulting solution was stirred for 30 minutes, followed by the dropwise addition of trimethylamine (5 ml). The reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO4 and then recrystallized from ethyl acetate to obtain BH-3-b (27.9 g, 67% yield).

[0352] MS: [M+H]+=453

[0353] Preparation of compound BH-3-c (<7-c>)

[0354] After dispersing compound BH-3-b (30 g, 66.3 mmol) in 250 mL of dimethylformamide, a solution of N-bromosuccinimide (12.4 g, 69.6 mmol) dissolved in 50 mL of dimethylformamide was slowly added dropwise. After reacting at room temperature for 4 hours, 600 mL of water was added dropwise. When a solid was formed, it was filtered, dissolved in ethyl acetate, and the resulting solution was placed in a separatory funnel and washed several times with distilled water. The product was recrystallized in ethyl acetate to obtain compound BH-3-c (29.9 g, 85% yield).

[0355] MS: [M+H]+=531

[0356] Preparation of compound BH-3 (<7-d>)

[0357] Compound BH-3 was obtained by synthesis and purification in the same manner as in the preparation of <2-a> compound core-2-a in Synthetic Example 2, except that compound BH-3-c was used instead of 1-bromo-3-chlorobenzene, and [1,1'-biphenyl]-2-ylboronic acid was used instead of compound core-1.

[0358] MS: [M+H]+=604

[0359] Synthesis Example 8. Synthesis of BH-4

[0360]

[0361] Preparation of compound BH-4 (<8-a>)

[0362] Compound BH-4 was obtained by synthesis and purification in the same manner as in the preparation of compound nucleus-2-a of Synthetic Example 2, except that 1-bromo-3-chlorobenzene was used instead of 9-bromo-10-(naphth-1-yl)anthracene-1,2,3,4,5,6,7,8-d8 in the preparation of compound nucleus-2-a of Synthetic Example 2.

[0363] MS: [M+H]+=569

[0364] Synthesis Example 9. Synthesis of BH-5

[0365]

[0366] <9-a> Preparation of compound BH-5

[0367] Compound BH-5 was obtained by synthesis and purification in the same manner as in the preparation of <2-a> compound nucleus-2-a in Synthetic Example 2, except that 1-bromo-3-chlorobenzene was used instead of 9-bromo-10-(naphth-2-yl-d7)anthracene-1,2,3,4,5,6,7,8-d8 in the preparation of <2-a> compound nucleus-2-a in Synthetic Example 2.

[0368] MS: [M+H]+=576

[0369] Synthesis Example 10. Synthesis of BH-6

[0370]

[0371] Preparation of <10-a> compound BH-6-a

[0372] Compound BH-6-a was obtained by synthesis and purification in the same manner as in the preparation of <2-a> compound nucleus-2-a in Synthetic Example 2, except that 1-bromo-3-chlorobenzene was replaced in the preparation of <2-a> compound nucleus-2-a in Synthetic Example 2 with 9-([1,1'-biphenyl]-3-yl)-10-bromoanthracene.

[0373] MS: [M+H]+=587

[0374] <10-b> Preparation of compound BH-6

[0375] Compound BH-6 was obtained by synthesis and purification in the same manner as in the preparation of compound BH-3-b of Synthesis Example 7, except that compound BH-6-a was used instead of compound BH-3-a in the preparation of compound BH-3-b of Synthesis Example 7.

[0376] MS: [M+H]+=613

[0377] Synthesis Example 11. Synthesis of BH-7

[0378]

[0379] Preparation of <11-a> compound BH-7-a

[0380] Compound BH-7-a was obtained by synthesis and purification in the same manner as in the preparation of compound nucleus-2-a of Synthetic Example 2, except that 1-bromo-3-chlorobenzene was used instead of 9-bromo-10-phenylanthracene in the preparation of compound nucleus-2-a of Synthetic Example 2.

[0381] MS: [M+H]+=511

[0382] <11-b>Preparation of compound BH-7

[0383] Compound BH-7 was obtained by synthesis and purification in the same manner as in the preparation of compound BH-3-b of Synthesis Example 7, except that compound BH-7-a was used instead of compound BH-3-a in the preparation of compound BH-3-b of Synthesis Example 7.

[0384] MS: [M+H]+=533

[0385] Synthesis Example 12. Synthesis of BH-8

[0386]

[0387] Preparation of <12-a> compound BH-8-a

[0388] Compound BH-8-a was obtained by synthesis and purification in the same manner as in the preparation of <2-a> compound nucleus-2-a in Synthetic Example 2, except that compound nucleus-3 was used instead of compound nucleus-1 and 9-bromo-10-(naphthyl-1-yl)anthracene was used instead of 1-bromo-3-chlorobenzene.

[0389] MS: [M+H]+=637

[0390] <12-b>Preparation of compound BH-8

[0391] Compound BH-8 was obtained by synthesis and purification in the same manner as in the preparation of compound BH-3-b of Synthesis Example 7, except that compound BH-8-a was used instead of compound BH-3-a.

[0392] MS: [M+H]+=665

[0393] Synthesis Example 13. Synthesis of BH-9

[0394]

[0395] Preparation of compound BH-9 (<13-a>)

[0396] Compound BH-9 was obtained by synthesis and purification in the same manner as in the preparation of compound nucleus-2-a of Synthetic Example 2, except that 1-bromo-3-chlorobenzene was used instead of 9-bromo-10-(naphth-1-yl-d7)anthracene-1,2,3,4,5,6,7,8-d8 in the preparation of compound nucleus-2-a of Synthetic Example 2.

[0397] MS: [M+H]+=576

[0398] Synthesis Example 14. Synthesis of BH-10

[0399]

[0400] Preparation of <14-a> compound BH-10-a

[0401] Compound BH-10-a was obtained by synthesis and purification in the same manner as in the preparation of <2-a> compound core-2-a in Synthetic Example 2, except that compound core-4 was used instead of compound core-1 and 9-([1,1'-biphenyl]-3-yl)-10-bromoanthracene was used instead of 1-bromo-3-chlorobenzene.

[0402] MS: [M+H]+=713

[0403] <14-b>Preparation of compound BH-10

[0404] Compound BH-10 was obtained by synthesis and purification in the same manner as in the preparation of compound BH-3-b of Synthesis Example 7, except that compound BH-10-a was used instead of compound BH-3-a.

[0405] MS: [M+H]+=746

[0406] Synthesis Example 15. Synthesis of BH-11

[0407]

[0408] Preparation of compound BH-11 (<15-a>)

[0409] Compound BH-11 was obtained by synthesis and purification in the same manner as in the preparation of <2-a> compound nucleus-2-a in Synthetic Example 2, except that compound BH-3-c was used instead of 1-bromo-3-chlorobenzene, and [1,1'-biphenyl]-4-ylboronic acid was used instead of compound nucleus-1.

[0410] MS: [M+H]+=604

[0411] Synthesis Example 16. Synthesis of BH-12

[0412]

[0413] Preparation of <16-a> compound BH-12-a

[0414] Compound BH-12-a was obtained by synthesis and purification in the same manner as in the preparation of <2-a> compound core-2-a in Synthetic Example 2, except that 9-bromoanthracene was used instead of 1-bromo-3-chlorobenzene, and compound core-3 was used instead of compound core-1.

[0415] MS: [M+H]+=511

[0416] Preparation of <16-b> compound BH-12-b

[0417] Compound BH-12-b was obtained by synthesis and purification in the same manner as in the preparation of compound BH-3-b of Synthesis Example 7, except that compound BH-12-a was used instead of compound BH-3-a in the preparation of compound BH-3-b of Synthesis Example 7.

[0418] MS: [M+H]+=533

[0419] Preparation of <16-c> compound BH-12-c

[0420] Compound BH-12-c was obtained by synthesis and purification in the same manner as in the preparation of compound BH-3-c of <7-c> in Synthesis Example 7, except that compound BH-12-b was used instead of compound BH-3-b in the preparation of compound BH-3-c of <7-c> in Synthesis Example 7.

[0421] MS: [M+H]+=611

[0422] Preparation of <16-d> compound BH-12

[0423] Compound BH-12 was obtained by synthesis and purification in the same manner as in the preparation of compound nucleus-2-a of <2-a> in Synthesis Example 2, except that compound BH-12-c and [1,1'-biphenyl]-4-ylboronic acid were used instead of 1-bromo-3-chlorobenzene and compound nucleus-1, respectively.

[0424] MS: [M+H]+=684

[0425] <Experiment Example 1: Fabrication of Organic Light-Emitting Devices>

[0426] Example 1.

[0427] A glass substrate thinly coated with 1,400 Å indium tin oxide (ITO) was immersed in distilled water containing a cleaning agent and ultrasonically washed. In this case, a product manufactured by Fischer Co. was used as the cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice for 10 minutes each time with distilled water. After washing with distilled water, ultrasonic washing was performed using isopropanol, acetone, and methanol solvents, and the resulting product was dried and then transferred to a plasma scrubber. Furthermore, the substrate was cleaned with oxygen plasma for 5 minutes and then transferred to a vacuum deposition machine.

[0428] On the prepared ITO transparent electrode, HI-A and HATCN are thermally vacuum deposited to thicknesses of 650 Å and 50 Å, respectively, to sequentially form a first hole injection layer and a second hole injection layer. On the second hole injection layer, HT-A is vacuum deposited to a thickness of 600 Å to form a hole transport layer. On the hole transport layer, HT-B is vacuum deposited to a thickness of 50 Å to form an electron blocking layer.

[0429] Subsequently, the following compound BD-A, which is a blue light-emitting dopant, is vacuum-deposited on the electron blocking layer at 4 wt% of the total weight of the light-emitting layer, and the following BH-1, which is vacuum-deposited at 96 wt% of the total weight of the light-emitting layer, is formed to a thickness of up to 200 Å, thereby forming the light-emitting layer.

[0430] Next, compound ET-A, serving as the first electron transport layer, is vacuum-deposited onto the luminescent layer to a thickness of 50 Å. Subsequently, ET-B and LiQ are vacuum-deposited in a 1:1 weight ratio to form a second electron transport layer with a thickness of 360 Å. LiQ is then vacuum-deposited onto the second electron transport layer to a thickness of 5 Å to form an electron injection layer. Aluminum and silver are deposited on the electron injection layer in a 10:1 weight ratio to a thickness of 220 Å, and aluminum is then deposited on top of this to a thickness of 1,000 Å to form the negative electrode.

[0431] In the aforementioned steps, the deposition rate of the organic material was maintained between 0.4 Å / s and 0.9 Å / s, the deposition rate of the aluminum negative electrode was maintained at 2 Å / s, and the vacuum level during deposition was maintained at 1 × 10⁻⁶. -7 Up to 5×10 -8 This led to the creation of organic light-emitting devices.

[0432]

[0433] Examples 2 to 12

[0434] The organic light-emitting devices of Examples 2 to 12 were manufactured in the same manner as in Example 1, except that the compounds described in Table 1 below were used instead of compound BH-1 in Example 1 as the main body of the light-emitting layer.

[0435]

[0436] Comparative Examples 1 to 5

[0437] Organic light-emitting devices of Comparative Examples 1 to 5 were manufactured in the same manner as in Example 1, except that the following compounds BH-a to BH-e were used instead of compound BH-1 in Example 1 as the main body of the light-emitting layer.

[0438]

[0439] Measurements were taken when 10 mA / cm² was applied to the organic light-emitting devices in Examples 1 to 12 and Comparative Examples 1 to 5. 2 The voltage and conversion efficiency (cd / A / y) at current densities and when 20 mA / cm² is applied to these devices. 2 Lifespan at current density (LT) 95 ), and the results are shown in Table 1 below. In this case, LT 95 This indicates that when 20 mA / cm 2 The ratio of the time taken for the brightness to decrease to 95% when the initial brightness is set to 100% at the given current density.

[0440] [Table 1]

[0441]

[0442] Conversion efficiency (cd / A / y) takes into account the material’s current efficiency (cd / A) compared to color purity (CIEy), and is an important reference value for the efficiency of both small and large organic light-emitting devices that aim for high brightness and high color gamut.

[0443] In Table 1, Examples 1 to 12, which use organic light-emitting devices of Formula 1 according to an exemplary embodiment of this specification, contain compounds containing at least one deuterium in anthracene; Comparative Examples 1 and 2 contain compounds that do not contain deuterium; and Comparative Examples 3 to 5 contain compounds that do not contain deuterium in anthracene cores.

[0444] Specifically, since the compound containing deuterium in an anthracene according to an exemplary embodiment of the present invention has structural properties that improve electron and hole mobility and improve molecular stability, compared with Comparative Examples 1 and 2 which do not contain deuterium and Comparative Examples 3 to 5 which do not contain deuterium in an anthracene core, it can be seen that the organic light-emitting device containing the compound is superior in terms of driving voltage, efficiency and lifetime.

Claims

1. An organic light-emitting device, comprising: First electrode; Second electrode; as well as An organic material layer having one or more layers is disposed between the first electrode and the second electrode. The organic material layer includes a light-emitting layer, and the light-emitting layer comprises a compound represented by the following chemical formula 1. The organic material layer includes a hole injection layer having two or more layers disposed between the light-emitting layer and the first electrode, and The hole injection layer comprises a compound represented by the chemical formula HI-1: [Chemical Formula 1] In chemical formula 1, D stands for deuterium. L1 is a direct bond; or a substituted or unsubstituted aryl group. Ar1 is a substituted or unsubstituted aryl group. R1 to R9 may be the same as or different from each other, and each is independently hydrogen; or deuterium. a1 is an integer from 1 to 8. [Chemical formula HI-1] In the chemical formula HI-1, R300 to R308 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 bonded to an adjacent group to form a substituted or unsubstituted ring. r301 and r302 are each integers from 1 to 4. r303 and r304 are each integers from 1 to 3. When r301 is 2 or greater, R301 may be the same or different from each other. When r302 is 2 or greater, R302 may be the same or different from each other. When r303 is 2 or greater, R303 may be the same or different from each other, and When r304 is 2 or greater, R304 can be the same or different from each other.

2. The organic light-emitting device according to claim 1, wherein chemical formula 1 is represented by the following chemical formula 1-1 or 1-2: [Chemical Formula 1-1] [Chemical Formula 1-2] In chemical formulas 1-1 and 1-2, The definitions of D, Ar1, a1, and R1 through R9 are the same as those defined in Formula 1, and L11 is a substituted or unsubstituted aryl group.

3. The organic light-emitting device according to claim 1, wherein chemical formula 1 is represented by chemical formulas 1-3 or 1-4: [Chemical Formulas 1-3] [Chemical Formulas 1-4] In chemical formulas 1-3 and 1-4, The definitions of D, Ar1, a1, and R1 through R9 are the same as those defined in Formula 1. a2 is an integer from 0 to 4. a3 is an integer from 0 to 4. a4 is an integer from 0 to 4, and 0≤a3+a4≤6.

4. The organic light-emitting device according to claim 1, wherein L1 is a direct bond; or an unsubstituted or deuterated monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and Ar1 is an unsubstituted or deuterated monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted with one or more substituents of a combination thereof, having 6 to 30 carbon atoms.

5. The organic light-emitting device according to claim 1, wherein chemical formula 1 is selected from any of the following compounds: 。 6. The organic light-emitting device according to claim 1, wherein the light-emitting layer comprises the compound represented by chemical formula 1 as the main body of the light-emitting layer.

7. The organic light-emitting device of claim 6, wherein the light-emitting layer comprises a dopant, and the dopant comprises one or more selected from fluorescent dopant and phosphorescent dopant.

8. The organic light-emitting device of claim 6, wherein the light-emitting layer comprises a dopant, and the dopant comprises one or more selected from phosphorescent dopant and thermally delayed fluorescence dopant.

9. The organic light-emitting device of claim 7, wherein the fluorescent dopant comprises one or more selected from arylamine-based compounds and boron-based compounds.

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