Organic electroluminescence device and amine compound for organic electroluminescence device

Abstract

Provided are an organic electroluminescence device and an amine compound for an organic electroluminescence device. The amine compound according to an embodiment of the present disclosure is represented by Formula 1. In Formula 1, Ar is a substituted or unsubstituted aryl group having 10 to 60 carbon atoms for forming a ring: Formula 1

Description

[0001] Cross-references to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2017-0174912, filed on December 19, 2017, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This disclosure relates herein to organic electroluminescent devices and amine compounds for use in organic electroluminescent devices. Background Technology

[0004] Development of organic electroluminescent display devices as image display devices is actively underway. Organic electroluminescent display devices differ from liquid crystal display devices. They are self-emissive display devices where holes and electrons injected by the first and second electrodes recombine in the emissive layer, and the luminescent material in the emissive layer, comprising organic compounds, emits light to achieve image display.

[0005] Organic light-emitting devices (OLEDs) are known, for example, comprising a first electrode, a hole transport layer disposed on (e.g., located on) the first electrode, an emissive layer disposed on the hole transport layer, an electron transport layer disposed on the emissive layer, and a second electrode disposed on the electron transport layer. Holes are injected by the first electrode, and the injected holes migrate through the hole transport layer and are injected into the emissive layer. Simultaneously, electrons are injected by the second electrode, and the injected electrons migrate through the electron transport layer and are injected into the emissive layer. Holes and electrons injected into the emissive layer recombine to generate excitons in the emissive layer. The OLED emits light generated by exciton transitions to the ground state. However, the configuration of the OLED is not limited to this, and various modifications are possible. When applying OLEDs to display devices, increased efficiency and lifetime of the OLED are required (or desired). Summary of the Invention

[0006] One or more aspects of embodiments of this disclosure relate to organic electroluminescent devices having high luminous efficiency and long lifetime.

[0007] One or more aspects of embodiments of this disclosure relate to amine compounds suitable for organic electroluminescent devices having high luminous efficiency and long lifetime.

[0008] One embodiment of this disclosure provides an organic electroluminescent device, comprising: a first electrode, a hole transport region disposed on the first electrode, a light-emitting layer disposed on the hole transport region, an electron transport region disposed on the light-emitting layer, and a second electrode disposed on the electron transport region. The hole transport region comprises an amine compound represented by the following formula 1:

[0009] Formula 1

[0010]

[0011] In Formula 1, Ar is a substituted or unsubstituted aryl group having 10 to 60 carbon atoms for forming a ring; L is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring; R1 and R2 are each independently hydrogen, deuterium, halogen atom, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring; "a" and "b" are each independently integers selected from 0 to 7; and "c" is an integer selected from 1 to 4.

[0012] In one embodiment, the hole transport region may include a hole injection layer disposed on the first electrode and a hole transport layer disposed on the hole injection layer. The hole transport layer may include an amine compound represented by Formula 1.

[0013] In one embodiment, the hole transport region may include multiple layers. The layer in contact with the light-emitting layer among the multiple layers may include an amine compound represented by Formula 1.

[0014] In one embodiment, L may be a substituted or unsubstituted phenylene or a substituted or unsubstituted naphthylene.

[0015] In one embodiment, the amine compound represented by Formula 1 may be represented by one of the following Formulas 2-1 to 2-3:

[0016] Equation 2-1

[0017]

[0018] Equation 2-2

[0019]

[0020] Equation 2-3

[0021]

[0022] In formulas 2-1 to 2-3, "d" is 0 or 1; R9 is hydrogen, deuterium, halogen atom, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms for ring formation, or substituted or unsubstituted heteroaryl with 2 to 30 carbon atoms for ring formation; "n" is an integer selected from 0 to 6; and Ar, R1, R2, "a" and "b" are the same as those defined above.

[0023] In one embodiment, an amine compound represented by any one of formulas 2-1 to 2-3 may be represented by any one of formulas 2-1-1 to 2-3-2:

[0024] Equation 2-1-1

[0025]

[0026] Equation 2-1-2

[0027]

[0028] Equation 2-2-1

[0029]

[0030] Equation 2-2-2

[0031]

[0032] Equation 2-3-1

[0033]

[0034] Equation 2-3-2

[0035]

[0036] In Equations 2-1-1 to 2-3-2, n1, n3 and n5 are each independently an integer selected from 0 to 4, n2, n4 and n6 are each independently an integer selected from 0 to 6, and Ar, R1, R2, R9, "a" and "b" are the same as those defined above.

[0037] In one embodiment, Ar may be a substituted or unsubstituted naphthyl or a substituted or unsubstituted phenanthryl.

[0038] In one embodiment, the amine compound represented by Formula 1 may be represented by one of the following Formulas 3-1 to 3-3:

[0039] Equation 3-1

[0040]

[0041] Equation 3-2

[0042]

[0043] Equation 3-3

[0044]

[0045] In formulas 3-1 to 3-3, R3 to R5 are each independently hydrogen, deuterium, halogen atom, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring; "e" is an integer selected from 0 to 7, and "f" and "g" are each independently an integer selected from 0 to 9.

[0046] In equations 3-1 to 3-3, R1, R2, “a”, “b” and L are the same as those defined above.

[0047] In one embodiment, at least one of “a” and “b” may be 1 or 2; and R1 and R2 may each be independently deuterium, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene group.

[0048] In one embodiment, the amine compound represented by Formula 1 can be represented by the following Formula 4:

[0049] Formula 4

[0050]

[0051] In Formula 4, "h" and "i" are each independently an integer from 0 to 2, at least one of "h" and "i" is 1 or 2, and R1 and R2 are each independently hydrogen, deuterium, halogen atom, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl with 2 to 30 carbon atoms for forming a ring.

[0052] In Equation 4, Ar, L, and “c” are the same as those defined above.

[0053] In one embodiment, the amine compound represented by Formula 1 can be represented by the following Formula 5:

[0054] Formula 5

[0055]

[0056] In Equation 5, R 11 To R 14 and R 21 To R 24Each is independently hydrogen, deuterium, halogen atom, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation, wherein R 11 To R 14 and R 21 To R 24 At least one of them is deuterium, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation. Selected from R 11 and R 21 R 12 and R 22 R 13 and R 23 and R 14 and R 24 At least two members in at least one group are different from each other.

[0057] In Equation 5, Ar, L, and “c” are the same as those defined above.

[0058] In one embodiment of this disclosure, an amine compound represented by Formula 1 is provided.

[0059] In one embodiment of this disclosure, an amine compound represented by Formula 6 is provided:

[0060] Formula 6

[0061]

[0062] In Equation 6, R6, R7, and R 10 Each R8 is independently hydrogen, deuterium, halogen atom, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation; each R8 is independently hydrogen, deuterium, halogen atom, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation, wherein multiple R8 groups may be linked to form a ring; "j" and "k" are each independently an integer selected from 0 to 7, "l" is an integer selected from 0 to 7, "m" is an integer of 0 or 1, and "u" is an integer selected from 0 to 6. Attached Figure Description

[0063] The accompanying drawings are included to provide a further understanding of this disclosure, and are incorporated in and form a part of this specification. The drawings illustrate exemplary embodiments of the present disclosure and, together with the description, serve to explain the principles of the disclosure. In the drawings:

[0064] Figure 1 A cross-sectional view of an organic electroluminescent device according to one embodiment of the present disclosure is shown for illustrative purposes; and

[0065] Figure 2 A cross-sectional view of an organic electroluminescent device according to one embodiment of the present disclosure is shown for illustrative purposes. Detailed Implementation

[0066] The above-described objectives, other objectives, features, and advantages of this disclosure will be readily understood by referring to the accompanying drawings and the description of exemplary embodiments. However, this disclosure may be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, exemplary embodiments are provided so that the contents of this disclosure are thorough and complete, and the spirit of this disclosure will be fully appreciated by those skilled in the art (e.g., readily apparent).

[0067] The same reference numerals refer to the same elements used to interpret each figure. In the accompanying drawings, the dimensions of elements may be enlarged for clarity of this disclosure. It will be understood that although the terms first, second, etc., may be used herein to describe various elements, these elements should not be limited by these terms. These terms are used only to distinguish one element from another. For example, the first element discussed below may be referred to as the second element, and similarly, the second element may be referred to as the first element. As used herein, the singular forms are intended to include the plural forms as well, unless the context clearly indicates otherwise.

[0068] It will be further understood that when the terms "comprising" or "including" are used in this specification, they indicate the presence of stated features, numbers, steps, operations, elements, components, or combinations thereof, but do not preclude the presence or addition of one or more other features, numbers, steps, operations, elements, components, or combinations thereof. It will also be understood that when a layer, film, region, plate, etc., is referred to as "on another component," it may be "directly" on the other component, or an intermediate component (e.g., a layer) may also be present. When a layer, film, region, plate, etc., is referred to as "below another component," it may be "directly" below the other component, or an intermediate component (e.g., a layer) may also be present.

[0069] First, refer to Figure 1 and Figure 2 An organic electroluminescent device according to an embodiment of the present disclosure is explained.

[0070] Figure 1A cross-sectional view of an organic electroluminescent device according to one embodiment of the present disclosure is shown for illustrative purposes. Figure 2 A cross-sectional view of an organic electroluminescent device according to one embodiment of the present disclosure is shown for illustrative purposes.

[0071] Reference Figure 1 and Figure 2 An organic electroluminescent device according to one embodiment of the present disclosure includes a first electrode EL1, a hole transport region HTR, a light-emitting layer EML, an electron transport region ETR, and a second electrode EL2.

[0072] The hole transport region (HTR) includes an amine compound according to embodiments of the present disclosure. Hereinafter, the amine compound according to embodiments of the present disclosure will be explained in more detail, followed by an explanation of each layer of the organic electroluminescent device 10.

[0073] The amine compound according to the embodiments of this disclosure is represented by the following formula 1:

[0074] Formula 1

[0075]

[0076] In Formula 1, L can be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring. For example, L can be a substituted or unsubstituted phenylene or a substituted or unsubstituted naphthylene.

[0077] Ar can be a substituted or unsubstituted aryl group having 10 to 60 carbon atoms for forming a ring. For example, Ar can be a substituted or unsubstituted naphthyl or a substituted or unsubstituted phenanthryl.

[0078] R1 and R2 can each independently be hydrogen, deuterium, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation. R1 and R2 can each independently be deuterium, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene group. For example, R1 and R2 can both be hydrogen atoms.

[0079] "a" and "b" can each be an integer selected from 0 to 7 independently. For example, "a" and "b" can each be an integer selected from 0 to 2 independently. If "a" is 1, then R1 can be non-hydrogen, and if "b" is 1, then R2 can be non-hydrogen. If "a" is 0, then the amine compound represented by Formula 1 can be unsubstituted by R1. If "b" is 0, then the amine compound represented by Formula 1 can be unsubstituted by R2. For example, "a" and "b" can both be 0, and the dibenzothiophene group in the amine compound represented by Formula 1 can be unsubstituted. If "a" is 2 or a larger integer, multiple R1 groups can be the same or different. If "b" is 2 or a larger integer, multiple R2 groups can be the same or different.

[0080] “c” is an integer selected from 1 to 4. If “c” is an integer of 2 or greater, the multiple L groups can be the same or different. If “c” is an integer of 2 or greater, the L groups can be connected in a line. For example, if there are multiple L groups (e.g., if Formula 1 has more than one L group), one L group can be connected to N, another L group can be connected to Ar, and the remaining L groups can be connected between the L group connected to N and the L group connected to Ar. For example, “c” can be 2, and the multiple L groups can be phenylene and naphthylene, respectively, and the phenylene and naphthylene can be connected in a line. In some embodiments, “c” can be 1, and N and Ar can be connected via a phenylene or naphthylene group.

[0081] In this instruction manual, It can refer to the part to be connected (e.g., the connection site).

[0082] In this specification, "substituted or unsubstituted" can mean a group that is not substituted or is substituted by at least one substituent selected from the group consisting of: deuterium, halogen, cyano, nitro, amino, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, boron, arylamine, phosphine oxide, phosphine sulfide, alkyl, alkenyl, aryl, and heterocyclic groups. Furthermore, each substituent listed above may itself be substituted or unsubstituted. For example, biphenyl can be described as aryl, or a phenyl group substituted with a phenyl group.

[0083] In this specification, the term "forming a ring via bonding with an adjacent group" can refer to the formation of a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle by bonding one group with an adjacent group. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and aromatic heterocycles. Hydrocarbon rings and heterocycles can each be monocyclic or polycyclic. Furthermore, a ring formed via bonding with an adjacent group can bond with another ring to form a spirostructure.

[0084] In this specification, the term "adjacent group" can refer to a pair of substituents, wherein the first substituent is attached to an atom directly bonded to another atom, which is replaced by the second substituent; a pair of substituents attached to the same atom; or a pair of substituents wherein the first substituent is spatially positioned closest to the second substituent. For example, in 1,2-xylene, the two methyl groups can be interpreted as "adjacent groups" to each other, and in 1,1-diethylcyclopentene, the two ethyl groups can be interpreted as "adjacent groups" to each other.

[0085] In this manual, direct connection may refer to a single key.

[0086] In this specification, halogen atoms may include, but are not limited to, fluorine, chlorine, bromine and / or iodine atoms.

[0087] In the specification, alkyl groups can be straight-chain, branched, or cyclic. The number of carbon atoms in an alkyl group can be 1 to 30, 1 to 20, 1 to 15, 1 to 10, or 1 to 6. Alkyl groups may, without limitation, include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyl... 2-Hexyldecyl, 2-Octylide, n-Undecyl, n-Dodecyl, 2-Ethyldodecyl, 2-Butyldodecyl, 2-Hexyldodecyl, 2-Octylide, n-Tridecyl, n-Tetradecyl, n-Pentadedecyl, n-Hexadecyl, 2-Ethylhexadecyl, 2-Butylhexadecyl, 2-Hexylhexadecyl, 2-Octylide, n-Heptadedecyl, n-Octadedecyl, n-Nondecyl, n-Eicosyl, 2-Ethyleicosyl, 2-Butyleicosyl, 2-Hexyleicosyl, 2-Octylide, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, etc.

[0088] In this specification, aryl can refer to a functional group or substituent derived from an aromatic hydrocarbon ring. Aryl can be monocyclic or polycyclic. The number of carbons in the aryl group used to form the ring can be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups may, without limitation, include phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, triphenyl, tetraphenyl, pentaphenyl, hexaphenyl, benzo[a]phenanthryl, pyrene, benzo[a]fluoranyl, trefyl, etc.

[0089] In this specification, the fluorene group may be substituted, and two substituents may combine with each other to form a spirostructure. Non-limiting examples of substituted fluorene groups are shown below. However, embodiments of this disclosure are not limited thereto:

[0090]

[0091] In this specification, a heteroaryl group can be a heteroaryl group (e.g., a cyclic aromatic group) comprising at least one of O, N, P, Si, and S as a cyclic heteroatom. If the heteroaryl group comprises two heteroatoms, the two heteroatoms can be the same or different. The number of carbon atoms in the ring used to form the heteroaryl group can be from 2 to 30, for example, from 2 to 20. The heteroaryl group can be a monocyclic heteroaryl or a polycyclic heteroaryl. Polycyclic heteroaryl groups can have a bicyclic or tricyclic structure. Examples of heteroaryl groups may be nonlimitingly included, such as thiophene, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinel, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenothiazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazolopyrazinyl, isoquinolinyl, indolyl, carbazole, N-arylcarbazole, N-heteroarylcarbazole, N-alkylcarbazole, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, thiophenothiophene, benzofuranyl, phenanthrolyl, isoxazolyl, thiadiazolyl, phenothiazinyl, dibenzothiophene, dibenzofuranyl, etc.

[0092] In this specification, the same interpretation of aryl can be applied to arylene, except that arylene is divalent. The same interpretation of heteroaryl can be applied to heteroarylene, except that heteroarylene is divalent.

[0093] In this specification, silane is not limited to alkylsilane and arylsilane. Examples of silane may include trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc. However, embodiments of this disclosure are not limited thereto.

[0094] In this specification, the number of carbon atoms in the amino group (e.g., the number of carbon atoms) is not particularly limited, but can be from 1 to 30. The amino group may include, without limitation, alkylamino and arylamino groups. Examples of amino groups may include, without limitation, methylamino, dimethylamino, phenylamino, diphenylamino, naphthylamino, 9-methyl-anthraylamino, triphenylamino, etc.

[0095] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but can be 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group can have the following non-limiting structures:

[0096]

[0097] In this specification, the number of carbon atoms in the sulfinyl group and sulfonyl group is not particularly limited, but can be from 1 to 30. The sulfinyl group may include, without limitation, alkylsulfinyl and arylsulfinyl groups. Examples of sulfonyl groups may include, without limitation, alkylsulfonyl and arylsulfonyl groups.

[0098] In this specification, the thio group may include, without limitation, alkyl thio groups and aryl thio groups.

[0099] In this specification, the oxygen group may, without limitation, include alkyloxy and aryloxy groups. Alkyloxy groups may be straight-chain, branched, or cyclic. The number of carbon atoms in an alkyloxy group is not particularly limited, but may be, for example, 1 to 20, or 1 to 10. Examples of oxygen groups without limitation include methyloxy, ethyloxy, n-propyloxy, isopropyloxy, butyloxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, etc.

[0100] In this specification, the term "boron group" is not limited to alkylboron group and arylboron group. Examples of boron groups may include trimethylboron group, triethylboron group, tert-butyldimethylboron group, triphenylboron group, diphenylboron group, phenylboron group, etc. However, the embodiments of this disclosure are not limited thereto.

[0101] In this specification, the alkenyl group can be straight-chain or branched. The number of carbon atoms in the alkenyl group is not particularly limited, but can be 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups may include vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienylaryl, styryl, styrylvinyl, etc. However, the embodiments disclosed herein are not limited thereto.

[0102] In the specification, the number of carbon atoms in the amino group is not particularly limited, but can be from 1 to 30. The amino group can include, without limitation, alkylamino and arylamino groups. Examples of amino groups include, without limitation, methylamino, dimethylamino, phenylamino, diphenylamino, naphthylamino, 9-methyl-anthraylamino, triphenylamino, etc.

[0103] In this specification, the alkyl group in alkylthio, alkylsulfonyl, alkylaryl, alkylamino, alkylboron, alkylsilyl, and alkylamine is the same as the alkyl group described above.

[0104] In this specification, the aryl group in aryloxy, arylthio, arylsulfonyl, arylamino, arylboryl, arylsilyl, and arylamine is the same as the aryl group mentioned above.

[0105] The amine compound according to the embodiments of this disclosure can be a monoamine compound.

[0106] In Equation 1, "c" can be 1. However, the embodiments of this disclosure are not limited to this, and "c" can be an integer selected from 1 to 3.

[0107] The amine compound represented by Formula 1 can be represented by the following Formula 2:

[0108] Formula 2

[0109]

[0110] In Formula 2, R9 is hydrogen, deuterium, halogen atom, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, "n" is an integer selected from 0 to 6, and the descriptions of R1, R2, "a", "b" and Ar are the same as those provided in Formula 1.

[0111] In Formula 2, "d" is 0 or 1. If "d" is 0, Formula 2 corresponds to Formula 1 (where L is phenylene). If "d" is 1, Formula 2 corresponds to Formula 1 (where L is naphthylene).

[0112] In Equation 2, if “n” is 1, R9 may not be hydrogen, and if “n” is 2 or greater, multiple R9 groups may be the same or different.

[0113] The amine compound represented by formula 2 can be represented by one of the following formulas 2-1 to 2-3:

[0114] Equation 2-1

[0115]

[0116] Equation 2-2

[0117]

[0118] Equation 2-3

[0119]

[0120] In Equations 2-1 to 2-3, R1, R2, R9, “a”, “b”, “n”, Ar and “d” are the same as those defined above.

[0121] The amine compound represented by formula 2-1 can be represented by formula 2-1-1 or formula 2-1-2:

[0122] Equation 2-1-1

[0123]

[0124] Equation 2-1-2

[0125]

[0126] In Equations 2-1-1 and 2-1-2, “n1” is an integer selected from 0 to 4, “n2” is an integer selected from 0 to 6, and R1, R2, R9, “a”, “b” and Ar are the same as those defined above.

[0127] The amine compound represented by formula 2-2 can be represented by formula 2-2-1 or formula 2-2-2:

[0128] Equation 2-2-1

[0129]

[0130] Equation 2-2-2

[0131]

[0132] In Equations 2-2-1 and 2-2-2, “n3” is an integer selected from 0 to 4, “n4” is an integer selected from 0 to 6, and R1, R2, R9, “a”, “b” and Ar are the same as those defined above.

[0133] The amine compound represented by formula 2-3 can be represented by formula 2-3-1 or formula 2-3-2:

[0134] Equation 2-3-1

[0135]

[0136] Equation 2-3-2

[0137]

[0138] In Equations 2-3-1 and 2-3-2, “n5” is an integer selected from 0 to 4, “n6” is an integer selected from 0 to 6, and R1, R2, R9, “a”, “b” and Ar are the same as those defined above.

[0139] The amine compound represented by Formula 1 can be represented by one of the following formulas 3-1 to 3-3:

[0140] Equation 3-1

[0141]

[0142] Equation 3-2

[0143]

[0144] Equation 3-3

[0145]

[0146] In formulas 3-1 to 3-3, R3 to R5 are each independently hydrogen, deuterium, halogen atom, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation. For example, R3 to R5 may each be independently substituted or unsubstituted phenyl or substituted or unsubstituted naphthyl group.

[0147] “e” can be an integer selected from 0 to 7. If “e” is 0, the amine compound represented by formula 3-1 may not be substituted with R3. If “e” is an integer of 2 or greater, multiple R3 groups may be the same or different.

[0148] "f" and "g" can each be an integer selected from 0 to 9. If "f" is 0, the amine compound represented by formula 3-2 may not be substituted with R4. If "f" is 2 or a larger integer, the multiple R4 groups may be the same or different. If "g" is 0, the amine compound represented by formula 3-3 may not be substituted with R5. If "g" is 2 or a larger integer, the multiple R5 groups may be the same or different.

[0149] The amine compound represented by Formula 1 can be represented by the following Formula 4:

[0150] Formula 4

[0151]

[0152] In Equation 4, "h" and "i" are each independently an integer selected from 0 to 2, at least one of "h" and "i" is 1 or 2, and Ar, L and "c" are the same as those defined above.

[0153] The amine compound represented by Formula 1 can be represented by the following Formula 5:

[0154] Formula 5

[0155]

[0156] In Equation 5, Ar, L, and “c” are the same as those defined above.

[0157] In Equation 5, R 11 To R 14 and R 21 To R 24 Each of these can independently be hydrogen, deuterium, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation. In some embodiments, R 11 To R 14 and R 21 To R 24 At least one of them may be deuterium, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation. For example, R 11 To R 14 and R 21 To R 24 At least one of them may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring.

[0158] Selected from R 11 and R 21 R 12 and R 22 R 13 and R 23 and R 14 and R 24 In R, at least two members of a group can be different. For example, R 11 It can be a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group, and R 21 It can be hydrogen. In one embodiment, R 12 It can be a fluorine atom or a chlorine atom, and R 22 It can be hydrogen. In one embodiment, R 13 It can be a substituted or unsubstituted ethyl group, and R 23 It can be hydrogen. In other words, if R... 11 To R 14 It is a substituent on a dibenzothiophene moiety of Formula 5, and R 21 To R 24 The substituent on another dibenzothiophene moiety of Formula 2 is replaced by different substituents at specific carbon positions in order to form an asymmetric structure with the nitrogen atom at the center.

[0159] The amine compound represented by Formula 1 can be represented by the following Formula 6:

[0160] Formula 6

[0161]

[0162] In Equation 6, R6, R7, and R 10 Each of the following can be independently hydrogen, deuterium, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation. R6 and R7 can each be independently deuterium, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene group.

[0163] In Equation 6, "j" and "k" can each independently be integers selected from 0 to 7, "l" can be an integer selected from 0 to 7, "m" can be 0 or 1, and "u" can be an integer selected from 0 to 6. If "j" is 1, R6 may not be hydrogen, and if "j" is 2 or greater, multiple R6 groups may be the same or different. If "k" is 1, R7 may not be hydrogen, and if "k" is 2 or greater, multiple R7 groups may be the same or different. If "l" is 1, R8 may not be hydrogen, and if "l" is 2 or greater, multiple R8 groups may be the same or different. If "u" is 1, R... 10 It can be non-hydrogen, and if "u" is 2 or greater, multiple Rs are allowed. 10 The functional groups are the same or different.

[0164] In Formula 6, R8 can be hydrogen, deuterium, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation. R8 can be a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group. In some embodiments, R8 can be linked to an adjacent group to form a ring. For example, in an amine compound represented by Formula 6, the naphthyl group can be substituted by two R8 groups, and the two substituted R8 groups can be linked to each other to form a six-membered aromatic ring. In the case of forming a six-membered aromatic ring via two R8 groups, in an amine compound represented by Formula 6, the phenanthrene group can be linked to the amine core via a phenylene linker (e.g., if "m" is 0) or a naphthylene linker (e.g., if "m" is 1).

[0165] The amine compound represented by Formula 1 may be at least one selected from the compounds represented by Group 1 of compounds. However, the embodiments of this disclosure are not limited thereto.

[0166] Compound group 1

[0167]

[0168]

[0169]

[0170] Referring to Formula 1 or Formula 6, the amine compound according to embodiments of this disclosure comprises two dibenzothiophene groups, which are directly bonded to the amine core at the 4-carbon position of each dibenzothiophene group (e.g., as illustrated in Formulas 1 and 6). Furthermore, at the amine core, an aryl substituent having 10 or more carbon atoms (e.g., represented by Ar) is substituted via a linker (e.g., represented by L) such as phenylene or naphthylene.

[0171] When amine compounds represented by Formula 1 or Formula 6 are applied to organic electroluminescent devices, high luminous efficiency and long lifetime can be ensured. The amine compounds represented by Formula 1 or Formula 6 comprise two dibenzothiophene groups, each attached to an amine core (e.g., bonded to the N atom of an amino group) at a carbon position of 4 (e.g., as illustrated in Formulas 1 and 6), resulting in high amorphous properties. Therefore, when amine compounds represented by Formula 1 or Formula 6 are applied to organic electroluminescent devices, high luminous efficiency and long lifetime can be achieved. Furthermore, the phenyl or naphthyl group attached to the amine core is protected by an aryl substituent having 10 or more carbon atoms, which can inhibit (e.g., reduce) the decomposition of the amine compound during device operation. Thus, high luminous efficiency can be maintained, and the device lifetime can be increased.

[0172] Reference Figure 1 and Figure 2 The following will explain an organic electroluminescent device according to embodiments of the present disclosure. The light-emitting layer (EML) may include an amine compound according to embodiments of the present disclosure. In some embodiments, the hole transport region (HTR) may include an amine compound represented by Formula 1.

[0173] The following will primarily explain the amine compounds according to the embodiments of this disclosure, with regard to the different features compared to the foregoing embodiments, and any parts not explained will follow the above explanation regarding the amine compounds according to the embodiments of this disclosure.

[0174] The first electrode EL1 is conductive. The first electrode EL1 can be a pixel electrode or an anode. The first electrode EL1 can be a transmissive electrode, a semi-reflective electrode, or a reflective electrode. If the first electrode EL1 is a transmissive electrode, it can be formed using a transparent metal oxide (such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO)). If the first electrode EL1 is a semi-reflective electrode or a reflective electrode, it can include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds thereof, or mixtures thereof (e.g., a mixture of Ag and Mg). Furthermore, the first electrode EL1 can include multiple layers, including a reflective layer or a semi-reflective layer formed using any of the above materials, or a transparent layer formed using ITO, IZO, ZnO, and / or ITZO.

[0175] The following will explain the case where the amine compound according to embodiments of the present disclosure is included in the hole transport region (HTR). However, embodiments of the present disclosure are not limited thereto. The amine compound according to embodiments of the present disclosure may be included in at least one of one or more organic layers disposed between the first electrode EL1 and the second electrode EL2. For example, the amine compound according to embodiments of the present disclosure may be included in the light-emitting layer (EML).

[0176] As described above, the organic electroluminescent device 10 according to embodiments of the present disclosure may include an amine compound according to embodiments of the present disclosure in the hole transport region HTR.

[0177] The hole transport region (HTR) may include an amine compound represented by Formula 6.

[0178] The hole transport region HTR is provided on the first electrode EL1. The hole transport region HTR may include at least one of the hole injection layer HIL, the hole transport layer HTL, the hole buffer layer, and the electron blocking layer.

[0179] Hole transport region (HTR) can have a single layer formed using a single material, a single layer formed using multiple different materials, or a multilayer structure including multiple layers formed using multiple different materials.

[0180] For example, the hole transport region HTR can have a monolayer structure such as a hole injection layer HIL or a hole transport layer HTL, and can have a monolayer structure formed using hole injection materials and hole transport materials. In some embodiments, the hole transport region HTR can non-limitingly have a monolayer structure formed using a variety of different materials, or have a structure (laminated from the first electrode EL1) of hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / hole buffer layer, hole injection layer HIL / hole buffer layer, hole transport layer HTL / hole buffer layer, or hole injection layer HIL / hole transport layer HTL / electron blocking layer.

[0181] Hole transport regions (HTRs) can be formed using various methods, such as vacuum deposition, spin coating, casting, Langmuir-Brookett (LB) method, inkjet printing, laser printing, and / or laser-induced thermal imaging (LITI).

[0182] The hole transport region (HTR) may include an amine compound according to embodiments of the present disclosure. The hole transport region (HTR) may include an amine compound according to embodiments of the present disclosure as a hole transport material. If the hole transport region (HTR) comprises multiple layers, the amine compound of the embodiment may be included in the layer contacting the light-emitting layer (EML) among the multiple layers. For example, if the hole transport region (HTR) consists of a hole injection layer (HIL) and a hole transport layer (HTL), such as... Figure 2 As shown, the amine compound according to the embodiments of this disclosure may be included in the hole transport layer (HTL).

[0183] If the hole transport layer HTL comprises an amine compound according to embodiments of the present disclosure, the hole injection layer HIL may, for example, non-limitingly comprise: phthalocyanine compounds (e.g., copper phthalocyanine); N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), 4,4',4”-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4”-tri{N-(1-naphthyl)-N-phenylamino}-triphenylamine (1-TNATA) Poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N'-dinaphthyl-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (NPD), triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetra(pentafluorophenyl)borate, 1,4,5,8,9,12-hexaazabenzophenanthrene hexanitrile (HAT-CN), etc.

[0184] In addition to the amine compounds according to embodiments of this disclosure, the hole transport layer (HTL) may further comprise any known (e.g., suitable) material. Hole transport layers (HTLs) may include, for example, non-limiting examples such as: carbazole derivatives (e.g., N-phenylcarbazole, polyvinylcarbazole and / or 1,3-bis(N-carbazolyl)phenyl (mCP)), fluorene derivatives, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), triphenylamine derivatives (e.g., 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA)), N,N'-bis(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (NPD), 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), etc.

[0185] The thickness of the hole transport region (HTR) can be approximately to approximately For example, about to approximately If the hole transport region (HTR) comprises both the hole injection layer (HIL) and the hole transport layer (HTL), then the thickness of the hole injection layer (HIL) can be approximately... to approximately For example, about to approximately Furthermore, the thickness of the hole transport layer (HTL) can be approximately to approximately If the thicknesses of the hole transport region (HTR), hole injection layer (HIL), and hole transport layer (HTL) satisfy any of the above ranges, satisfactory (or suitable) hole transport properties can be obtained without a significant increase in the driving voltage.

[0186] In addition to the materials described above, the hole transport region (HTR) may further include a charge-generating material to increase conductivity. The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region (HTR). The charge-generating material may be, for example, a p-type dopant. The p-type dopant may be, non-limitingly, one of quinone derivatives, metal oxides, and cyano-containing compounds. For example, non-limiting examples of p-type dopant may include quinone derivatives (such as tetracyanoquinone dimethyl (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl (F4-TCNQ)) and metal oxides (such as tungsten oxide and / or molybdenum oxide).

[0187] As described above, in addition to the hole injection layer (HIL) and the hole transport layer (HTL), the hole transport region (HTR) may further include at least one of a hole buffer layer and an electron blocking layer. The hole buffer layer can compensate for the optical resonant distance and improve luminous efficiency based on the wavelength of light emitted by the emissive layer (EML). Any material included in the hole transport region (HTR) can be used as the material included in the hole buffer layer. The electron blocking layer is a layer configured to prevent or reduce electron injection from the electron transport region (ETR) into the hole transport region (HTR).

[0188] An emissive layer (EML) is provided on the hole transport region (HTR). The EML is disposed on the hole transport layer (HTL) and may be in contact with the HTL (e.g., may be in contact). The thickness of the EML may be, for example, approximately... to approximately The light-emitting layer (EML) can be a single layer formed using a single material, a single layer formed using multiple different materials, or a multilayer structure with multiple layers formed using multiple different materials.

[0189] The emissive layer (EML) can emit one of the following colors of light: red, green, blue, white, yellow, and cyan. The EML can include fluorescent or phosphorescent materials. For example, the EML can include a thermally induced delayed fluorescence (TADF) material.

[0190] The light-emitting layer (EML) can include a host and dopants.

[0191] The host material of the luminescent layer EML can be selected from anthracene derivatives, fluoranthene derivatives, pyrene derivatives, aromatic yne derivatives, fluorene derivatives, perylene derivatives, chrysene derivatives, and phenanthrene derivatives. For example, the host material can be selected from pyrene derivatives, perylene derivatives, chrysene derivatives, phenanthrene derivatives, and anthracene derivatives. For example, an anthracene derivative represented by the following formula 7 can be used as the host material of the luminescent layer EML:

[0192] Formula 7

[0193]

[0194] In Formula 7, Y1 to Y4 can each independently be hydrogen, deuterium, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation. m1 and m2 can each independently be an integer selected from 0 to 4, and m3 and m4 can each independently be an integer selected from 0 to 5. In Formula 7, Y3 and Y4 can each independently combine with adjacent groups to form a ring.

[0195] Compounds represented by Formula 7 may include, for example, compounds represented by the following structures. However, compounds represented by Formula 7 are not limited to the following structures.

[0196]

[0197] The main body is not particularly limited and may include, for example, tris(8-hydroxyquinoline)aluminum (Alq3), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), poly(N-vinylcarbazole) (PVK), 9,10-bis(naphthyl-2-yl)anthracene (ADN), 4,4',4”-tris(carbazolyl-9-yl)-triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), 3-tert-butyl-9,10-bis(naphthyl-2-yl)anthracene (TBADN), di(styryl)aromatics (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), etc.

[0198] Dopant may be, for example, styrene derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styrene]stilbene (DPAVB) and / or N-(4-((E)-2-(6-((E)-4-(diphenylamino)styrene)naphth-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi)), perylene and its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene and its derivatives (e.g., 1,1-dipyrene, 1,4-dipyrenebenzene and / or 1,4-bis(N,N-diphenylamino)pyrene), etc. The dopant can also be 10-phenyl-10H,10'H-spiro[acridin-9,9'-anthracene]-10'-one.

[0199] If the emissive layer EML emits red light, the emissive layer EML may further include a fluorescent material, which includes tris(dibenzoylmethane) o-phenanthroline europium (PBD:Eu(DBM)3(Phen)) and / or perylene. If the emissive layer EML emits red light, the dopant included in the emissive layer EML may be selected from, for example, metal complexes or organometallic complexes (such as bis(1-phenylisoquinoline)acetylacetonate iridium (PIQIr(acac)), bis(1-phenylquinoline)acetylacetonate iridium (PQIr(acac)), tris(1-phenylquinoline)iridium (PQIr) and octaethylporphyrin platinum (PtOEP)), rubrene and its derivatives, and 4-dicyanomethylene-2-(p-dimethylaminostyryl)-6-methyl-4H-pyran (DCM) and its derivatives.

[0200] If the emissive layer EML emits green light, the emissive layer EML may, in one step, include a fluorescent material, which may include tris(8-hydroxyquinoline)aluminum (Alq3). If the emissive layer EML emits green light, the dopant included in the emissive layer EML may be selected from, for example, metal complexes or organometallic complexes such as faceted tris(2-phenylpyridine)iridium (Ir(ppy)3) and coumarin and its derivatives.

[0201] If the emissive layer EML emits blue light, the emissive layer EML may further include a fluorescent material, which includes at least one selected from, for example, polymers composed of spiro-DPVBi, spiro-6P, stilbene (DSB), stilbene-aromatic (DSA), polyfluorene (PFO) polymers, and poly(p-phenylenevinylene) (PPV) polymers. If the emissive layer EML emits blue light, the dopant included in the emissive layer EML may be selected from metal complexes or organometallic complexes (such as (4,6-F2ppy)2Irpic) and perylene and its derivatives.

[0202] The electron transport region (ETR) is disposed on the light-emitting layer (EML). The ETR may include at least one of a hole blocking layer, an electron transport layer (ETL), and an electron injection layer (EIL). However, embodiments of this disclosure are not limited thereto.

[0203] The electronic transmission region (ETR) can have a single layer made of a single material, a single layer made of multiple different materials, or a multi-layer structure with multiple layers made of multiple different materials.

[0204] For example, the electron transport region (ETR) may have a single-layer structure of an electron injection layer (EIL) or an electron transport layer (ETL), or a single-layer structure formed using an electron injection material and an electron transport material. In some embodiments, the electron transport region (ETR) may not be limited to having a single-layer structure (with various different materials), or may have a structure of an electron transport layer (ETL) / electron injection layer (EIL) or a hole blocking layer / electron transport layer (ETL) / electron injection layer (EIL) laminated from the first electrode (EL1).

[0205] Various methods can be used to form the electron transport region (ETR), such as vacuum deposition, spin coating, casting, Langmuir-Brookett (LB) method, inkjet printing, laser printing and / or laser-induced thermal imaging (LITI).

[0206] Electron transport layers (ETLs) may, without limitation, include, for example, tris(8-hydroxyquinoline)aluminum (Alq3), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene, 2,4,6-tris(3'-(pyridyl)-biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazolyl-1-yl)phenyl)-9,10-dinaphthylanthracene, and 1,3,5-tris(1-phenyl-1H-benzimidazolyl-2-yl)benzene (TP). Bi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole ( t Bu-PBD), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinoline-10-hydroxy)beryllium (Bebq2), 9,10-di(naphthyl-2-yl)anthracene (ADN), bis[2-(diphenylphosphine)phenyl]ether oxide (DPEPO), or mixtures thereof. The thickness of the electron transport layer (ETL) can be approximately to approximately For example, about to approximately If the thickness of the electron transport layer (ETL) meets the above range, satisfactory (or suitable) electron transport properties can be obtained without a significant increase in the driving voltage.

[0207] If the electron transport region (ETR) includes an electron injection layer (EIL), it may include metals such as Al, Ag, Li, Mg, and / or Ca, or mixtures thereof. However, embodiments of this disclosure are not limited thereto. For example, the electron injection layer EIL may use LiF, lithium 8-hydroxyquinoline (Liq), Li₂O, BaO, NaCl, CsF, lanthanide metals (such as Yb), or metal halides (such as RbCl and RbI). However, embodiments of this disclosure are not limited thereto. A mixture of electron transport material and insulating organometallic salt may also be used to form the electron injection layer EIL. The organometallic salt may be a material having a band gap of about 4 eV or higher. In some embodiments, for example, the organometallic salt may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, and / or metal stearate. The thickness of the electron injection layer EIL may be approximately [missing information - likely a number]. to approximately If the thickness of the electron injection layer (EIL) meets the above range, satisfactory electron transport properties can be obtained without a significant increase in driving voltage.

[0208] The electron transport region (ETR) may include a hole blocking layer as described above. The hole blocking layer may include, for example, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and 4,7-diphenyl-1,10-phenanthroline (Bphen). However, embodiments of this disclosure are not limited thereto.

[0209] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 can be a common electrode or a cathode. The second electrode EL2 can be a transmission electrode, a semi-reflective electrode, or a reflection electrode. If the second electrode EL2 is a transmission electrode, it can include a transparent metal oxide, such as ITO, IZO, ZnO, ITZO, etc.

[0210] If the second electrode EL2 is a semi-reflective electrode or a reflective electrode, then the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, their compounds, or mixtures thereof (e.g., a mixture of Ag and Mg). The second electrode EL2 may have a multilayer structure, which, without limitation, includes a reflective or semi-reflective layer formed using any of the above-mentioned materials and a transparent conductive layer formed using ITO, IZO, ZnO, ITZO, etc.

[0211] Although not shown, the second electrode EL2 may be connected to (e.g., coupled to) the auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

[0212] In the organic electroluminescent device 10, depending on the voltage applied to each of the first electrode EL1 and the second electrode EL2, holes injected by the first electrode EL1 can migrate to the emissive layer EML via the hole transport region HTR, and electrons injected by the second electrode EL2 can migrate to the emissive layer EML via the electron transport region ETR. Electrons and holes recombine in the emissive layer EML to generate excitons, and the excitons emit light by transitioning from the excited state to the ground state.

[0213] If the organic electroluminescent device 10 is a top-emitting type (e.g., a top-emitting organic electroluminescent device), then the first electrode EL1 may be a reflective electrode, and the second electrode EL2 may be a transmissive electrode or a semi-reflective electrode. If the organic electroluminescent device 10 is a bottom-emitting type (e.g., a bottom-emitting organic electroluminescent device), then the first electrode EL1 may be a transmissive electrode or a semi-reflective electrode, and the second electrode EL2 may be a reflective electrode.

[0214] Organic electroluminescent devices according to embodiments of the present disclosure include amine compounds represented by Formula 1 or Formula 6, ensuring high luminous efficiency and long lifetime. The amine compounds according to embodiments of the present disclosure can be used as hole transport materials, achieving high luminous efficiency and long lifetime in organic electroluminescent devices. For example, an amine compound represented by Formula 1 or Formula 6 includes two dibenzothiophene groups bonded to an amine core at each of the four carbon positions (e.g., as illustrated in Formulas 1 and 6), resulting in an organic electroluminescent device with high amorphous properties, high hole transport properties, and high luminous efficiency and long lifetime. Furthermore, the divalent phenyl or naphthyl group bonded to the amine core is protected by an aryl substituent having 10 or more carbon atoms, which can suppress (or reduce) the decomposition of the amine compound during device operation, maintaining high luminous efficiency and increasing device lifetime.

[0215] The present disclosure will be explained in more detail below with reference to specific preparation methods, embodiments, and comparative embodiments. The following embodiments are merely illustrative to aid in understanding the present disclosure, and the scope of the present disclosure is not limited thereto.

[0216] For example, amine compounds according to the exemplary embodiments of this disclosure can be synthesized as follows. However, the embodiments of this disclosure are not limited thereto.

[0217] 1. Synthesis of compound 1

[0218]

[0219] A toluene suspension (1150 ml) of compound A (14.0 g, 63.9 mmol), compound B (33.6 g, 127.7 mmol), tris(dibenzylacetone)palladium(0) (5.8 g, 6.4 mmol), tri-tert-butylphosphine (2.1 g, 10.2 mmol), and sodium tert-butoxide (24.5 g, 6.4 mmol) was degassed at approximately 80 °C and heated for approximately 4 hours under an argon (Ar) atmosphere. After cooling in air, it was... The reaction solution was filtered, and the residue obtained after concentration was separated by column chromatography to obtain compound 1 (26.5 g, 45.3 mmol, 71%). The molecular weight of compound 1 was determined to be 583 by rapid atomic impact mass spectrometry (FAB-MS).

[0220] 2. Synthesis of compound 4

[0221] Synthetic intermediate E

[0222]

[0223] A toluene / EtOH / H2O suspension (1200 / 120 / 240 ml) of compound C (37.6 g, 146.1 mmol), compound D (20.0 g, 146.1 mmol), tetrakis(triphenylphosphine)palladium(0) (8.4 g, 7.3 mmol) and potassium carbonate (24.2 g, 175.3 mmol) was degassed at approximately 80 °C under an argon (Ar) atmosphere and heated for approximately 4 hours. After cooling in air, it was... The reaction solution was filtered, and the residue obtained after concentration was separated by column chromatography to obtain intermediate E (25.5 g, 94.9 mmol, 65%). The molecular weight of intermediate E was determined to be 269 by FAB-MS.

[0224] Synthetic compound 4

[0225]

[0226] A toluene suspension (940 ml) of intermediate E (14.0 g, 52.0 mmol), compound B (27.4 g, 104.0 mmol), tris(dibenzylacetone)dipalladium(0) (4.8 g, 5.2 mmol), tri-tert-butylphosphine (1.7 g, 8.3 mmol), and sodium tert-butoxide (20.0 g, 5.2 mmol) was degassed at approximately 80 °C and heated for approximately 4 hours under an argon (Ar) atmosphere. After cooling in air, it was... The reaction solution was filtered, and the residue obtained by concentration was separated by column chromatography to obtain compound 4 (22.4 g, 35.4 mmol, 68%). The molecular weight of compound 4 was determined to be 633 by FAB-MS.

[0227] 3. Synthesis of compound 12

[0228] Synthetic intermediate H

[0229]

[0230] A toluene / EtOH / H2O suspension (880 / 90 / 180 ml) of compound F (22.1 g, 107.0 mmol), compound G (20.0 g, 187.0 mmol), tetrakis(triphenylphosphine)palladium(0) (6.2 g, 5.35 mmol) and potassium carbonate (17.7 g, 128.3 mmol) was degassed at approximately 80 °C under an argon (Ar) atmosphere and heated for approximately 4 hours. After cooling in air, it was... The reaction solution was filtered, and the residue obtained after concentration was separated by column chromatography to obtain intermediate H (15.8 g, 58.8 mmol, 55%). The molecular weight of intermediate H was determined to be 269 by FAB-MS.

[0231] Synthetic compound 12

[0232]

[0233] A toluene suspension (940 ml) of intermediate H (14.0 g, 52.0 mmol), compound B (27.4 g, 104.0 mmol), tris(dibenzylacetone)dipalladium(0) (4.8 g, 5.2 mmol), tri-tert-butylphosphine (1.7 g, 8.3 mmol), and sodium tert-butoxide (20.0 g, 5.2 mmol) was degassed at approximately 80 °C and heated for approximately 4 hours under an argon (Ar) atmosphere. After cooling in air, it was... The reaction solution was filtered, and the residue obtained by concentration was separated by column chromatography to obtain compound 12 (24.7 g, 39.0 mmol, 75%). The molecular weight of compound 12 was determined to be 633 by FAB-MS.

[0234] 4. Synthesize compound 27

[0235] Synthetic intermediate I

[0236]

[0237] A toluene suspension (1600 ml) of compound A (20.0 g, 91.2 mmol), compound B (24.0 g, 91.2 mmol), tris(dibenzylacetone)palladium(0) (8.4 g, 9.1 mmol), tri-tert-butylphosphine (3.0 g, 14.6 mmol), and sodium tert-butoxide (17.5 g, 182.4 mmol) was degassed at approximately 80 °C and heated for approximately 4 hours under an argon (Ar) atmosphere. After cooling in air, it was... The reaction solution was filtered, and the residue obtained after concentration was separated by column chromatography to obtain intermediate I (28.9 g, 72.1 mmol, 79%). The molecular weight of intermediate I was determined to be 401 by FAB-MS.

[0238] Synthetic compound 27

[0239]

[0240] A toluene suspension (1100 ml) of intermediate I (25.0 g, 62.3 mmol), compound J (21.1 g, 62.3 mmol), tris(dibenzylacetone)palladium(0) (5.7 g, 6.2 mmol), tri-tert-butylphosphine (2.0 g, 10.0 mmol), and sodium tert-butoxide (12.0 g, 124.5 mmol) was degassed at approximately 80 °C and heated for approximately 4 hours under an argon (Ar) atmosphere. After cooling in air, it was... The reaction solution was filtered, and the residue obtained after concentration was separated by column chromatography to give compound 27 (29.6 g, 44.8 mmol, 72%). The molecular weight of the compound was determined to be 659 by FAB-MS. Based on this result, the synthesized compound was identified as compound 27.

[0241] 5. Synthesize compound 38

[0242]

[0243] A toluene suspension (900 ml) of intermediate I (20.0 g, 49.8 mmol), compound K (22.2 g, 49.8 mmol), tris(dibenzylacetone)dipalladium(0) (4.6 g, 5.0 mmol), tri-tert-butylphosphine (1.6 g, 8.0 mmol), and sodium tert-butoxide (9.6 g, 99.6 mmol) was degassed at approximately 80 °C and heated for approximately 4 hours under an argon (Ar) atmosphere. After cooling in air, it was... The reaction solution was filtered, and the residue obtained after concentration was separated by column chromatography to give compound 38 (25.9 g, 33.9 mmol, 68%). The molecular weight of the compound was determined to be 765 by FAB-MS. Based on this result, the synthesized compound was identified as compound 38.

[0244] Experimental Example

[0245] Device manufacturing example

[0246] Organic electroluminescent devices of Examples 1 to 5 were fabricated using compounds 1, 4, 12, 27, and 38 as hole transport materials.

[0247] Example Compounds

[0248]

[0249] The apparatus used to manufacture Comparative Examples 1 to 6 was prepared using comparative compounds c1 to c6.

[0250] Comparison of compounds

[0251]

[0252] The organic electroluminescent devices of Examples 1 to 5 and Comparative Examples 1 to 6 were manufactured as follows: a first electrode of approximately 150 nm thickness was formed using ITO; a hole injection layer of approximately 60 nm thickness was formed using 4,4',4”-tri{N-(1-naphthyl)-N-phenylamino}-triphenylamine (1-TNATA); a hole transport layer of approximately 30 nm thickness was formed using the respective compounds of the examples or comparative compounds; a light-emitting layer of approximately 25 nm thickness was formed using 2,5,8,11-tetra-tert-butylperylene (TBP)-doped dianathenium (ADN); an electron transport layer of approximately 25 nm thickness was formed using Alq3; an electron injection layer of approximately 1 nm thickness was formed using LiF; and a second electrode of approximately 100 nm thickness was formed using Al. Each layer was formed under vacuum by deposition.

[0253] Experimental Example

[0254] The luminous efficiency and luminous lifetime of organic electroluminescent devices manufactured using compounds 1, 4, 12, 27, and 38 of Examples and comparative compounds c1 to c6 were evaluated. The evaluation results are shown in Table 1 below. The evaluation results of the properties of the examples and comparative examples in Table 1 are the relative ratios of luminous efficiency and luminous lifetime relative to 100% of the luminous efficiency and luminous lifetime of the organic electroluminescent device of Comparative Example 1.

[0255] Table 1

[0256]

[0257]

[0258] Referring to the results in Table 1, it was found that Examples 1 to 5 exhibited improved luminous efficiency and / or device lifetime compared to Comparative Examples 1 to 6. More specifically, compared to Comparative Examples 1 to 5, which included hole transport materials having a similar core structure, Examples 1 to 5 exhibited improved luminous efficiency and / or device lifetime.

[0259] According to embodiments of this disclosure, the compounds included in Examples 1 to 5 comprise two dibenzothiophene groups (e.g., as shown in the compound image) bonded to the amine core at each of the four carbon positions. Due to the high amorphous properties of the compounds of this embodiment, high hole transport properties can be obtained if the compounds are used as hole transport materials, ensuring high luminous efficiency and long lifetime of the organic electroluminescent device. Furthermore, the divalent phenyl or naphthyl group bonded to the amine core (e.g., to the central N atom) is protected by an aryl substituent having 10 or more carbon atoms, which can suppress (reduce) the decomposition of the amine compound during device operation, maintaining high luminous efficiency and increasing the device lifetime.

[0260] Comparative compound c1 included in Comparative Example 1 comprises two dibenzothiophene groups. These two dibenzothiophene groups are bonded to the amine core at each of the four carbon positions (e.g., the same positions as in the compound of Formula 1), but the naphthyl group bonded to the amine core is unsubstituented. Therefore, compared to the example compounds, the protection of the naphthyl group is not achieved, and the amine compound can decompose during device operation. Therefore, compared to the examples, the luminous efficiency and device lifetime of Comparative Example 1 are reduced.

[0261] Comparative compound c2 included in Comparative Example 2 comprises two dibenzothiophene groups bonded to the amine core at each of the four carbon positions, but with a triphenylene bonded to the amine core. The triphenylene lowers the LUMO level of the amine compound, and compared to the example compounds, comparative compound c2 exhibits decreased hole transport properties, and compared to the examples, the luminous efficiency and device lifetime of Comparative Example 2 are reduced.

[0262] In Comparative Examples 3 and 4, which respectively include comparative compounds c3 and c4, a dibenzothiophene group is bonded to the amine core; however, one of the dibenzothiophene groups is bonded to the amino group at a 3-carbon position rather than at a 4-carbon position. If the dibenzothiophene group is bonded to the amine core at a 3-carbon position (as shown in Comparative Compounds c3 and c4), the crystallinity of the amine compound can increase, and the amorphous properties decrease compared to the example compounds. Therefore, the hole transport properties of Comparative Compounds c3 and c4 decrease compared to the example compounds, and the luminous efficiency and device lifetime of Comparative Examples 3 and 4 can be reduced compared to the examples.

[0263] Comparative compound c5, included in Comparative Example 5, comprises two dibenzothiophene groups bonded to an amine core at each of the four carbon positions, with a substituted phenylene group on the amine core. Here, the dibenzofuran group is attached to the phenylene group in Comparative Compound c5, and compared to the compounds of the examples, the stability of the compound is reduced and it tends to (e.g., is more prone to) decomposition. Therefore, compared to the examples, the luminous efficiency and device lifetime of Comparative Example 5 are reduced.

[0264] Comparative Compound C6, included in Comparative Example 6, comprises two dibenzothiophene groups bonded to the amine nucleus at each of the four carbon positions. However, the dibenzothiophene groups are bonded to the amine nucleus via a phenylene or divalent biphenyl group rather than directly to the amine nucleus. Therefore, the distance between the dibenzothiophene groups and the amine nucleus is increased, and the hole transport properties of Comparative Compound C6 are reduced compared to the example compounds. Consequently, the luminous efficiency and device lifetime of Comparative Example 6 are reduced compared to the examples.

[0265] The organic electroluminescent device according to the embodiments of this disclosure has excellent luminous efficiency and long lifespan.

[0266] The amine compounds according to embodiments of this disclosure can be used as materials for organic electroluminescent devices.

[0267] Organic electroluminescent devices, including amine compounds according to embodiments of the present disclosure, can achieve excellent luminous efficiency and long lifespan.

[0268] Expressions such as "at least one of...", "one of...", and "selected from..." modify the entire column of elements when used before / after an element, rather than modifying a single element in that column. Furthermore, the use of "may" in describing embodiments of the invention refers to "one or more embodiments of the invention".

[0269] As used herein, the terms “use,” “using,” and “used” can be considered synonyms for the terms “utilize,” “utilizing,” and “utilized,” respectively.

[0270] Furthermore, the terms “substantially,” “about,” and similar terms are used as approximations rather than as terms of degree, and are intended to account for the inherent biases of the measured or calculated values, as will be recognized by those skilled in the art.

[0271] Furthermore, any numerical range described herein is intended to include all subranges with the same numerical precision covering the range. For example, the range “1.0 to 10.0” is intended to include all subranges between the minimum value 1.0 and the maximum value 10.0 (inclusive), i.e., a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit described herein is intended to include all lower numerical limits covered therein, and any minimum numerical limit described in this specification is intended to include all higher numerical limits covered therein. Therefore, the applicant reserves the right to amend this specification (including the claims) to expressly describe any subranges included within the range expressly described herein.

[0272] While exemplary embodiments of the invention have been described herein, it is to be understood that the invention should not be limited to these exemplary embodiments, but rather various changes and modifications can be made by those skilled in the art within the spirit and scope of the invention as defined by the claims of the invention and their equivalents.

Claims

1. An amine compound, said amine compound being represented by the following formula 1: Formula 1 ， In Equation 1, Ar is an unsubstituted naphthyl or an unsubstituted phenanthryl. L represents unsubstituted phenylene or unsubstituted naphthylene. R1 and R2 are each independently hydrogen, deuterium, an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothiophene group. "a" is an integer selected from 0 to 2, and "b" is 0. "c" is 1.

2. The amine compound of claim 1, wherein the amine compound represented by formula 1 is represented by one of the following formulas 2-1 to 2-3: Equation 2-1 Equation 2-2 Equation 2-3 ， In equations 2-1 to 2-3, "d" can be 0 or 1. R9 is hydrogen. "n" is an integer selected from 0 to 6, and Ar, R1, R2, "a" and "b" are the same as those defined in Equation 1.

3. The amine compound of claim 2, wherein the amine compound represented by any one of formulas 2-1 to 2-3 is represented by any one of formulas 2-1-1 to 2-3-2: Equation 2-1-1 Equation 2-1-2 Equation 2-2-1 Equation 2-2-2 Equation 2-3-1 Equation 2-3-2 ， Among them, in equations 2-1-1 to 2-3-2, n1, n3, and n5 are each independent integers selected from 0 to 4. n2, n4, and n6 are each an independent integer selected from 0 to 6. R9 is the same as that defined in Equations 2-1 to 2-3, and Ar, R1, R2, "a" and "b" are the same as those defined in Equation 1.

4. The amine compound of claim 1, wherein the amine compound represented by formula 1 is represented by one of the following formulas 3-1 to 3-3: Equation 3-1 Equation 3-2 Equation 3-3 ， Among them, in equations 3-1 to 3-3, R3 to R5 are each independently hydrogen. "e" is an integer selected from 0 to 7. "f" and "g" are each an integer selected from 0 to 9, and R1, R2, "a", "b" and L are the same as those defined in Equation 1.

5. The amine compound of claim 1, wherein the amine compound represented by formula 1 is represented by the following formula 4: Formula 4 ， In Equation 4, "h" is 1 or 2, and "i" is 0. R1 and R2 are each independently hydrogen, deuterium, an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothiophene group. Ar, L, and "c" are the same as those defined in Equation 1.

6. The amine compound of claim 1, wherein the amine compound represented by formula 1 is represented by the following formula 5: Formula 5 ， In Equation 5, R 11 To R 14 Each is independently hydrogen, deuterium, an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothiophene group, wherein R 11 To R 14 At least one of them is deuterium, an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothiophene group. R 21 To R 24 Each is independently hydrogen. Selected from R 11 and R 21 R 12 and R 22 R 13 and R 23 and R 14 and R 24 At least two members in at least one group are different from each other, and Ar, L, and "c" are the same as those defined in Equation 1.

7. The amine compound of claim 1, wherein the amine compound represented by formula 1 is at least one selected from the group consisting of compounds represented by group 1: Compound group 1 。 8. An amine compound, said amine compound being represented by the following formula 6: Formula 6 ， In Equation 6, R6 and R7 are each independently hydrogen, deuterium, an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothiophene group. R8 and R 10 Each is independently hydrogen. "j" is an integer selected from 0 to 2, and "k" is 0. "l" is an integer selected from 0 to 7. "u" is an integer selected from 0 to 6, and "m" is an integer of 0 or 1.

9. An organic electroluminescent device, comprising: First electrode; The hole transport region on the first electrode, wherein the hole transport region comprises an amine compound as described in any one of claims 1 to 8; A light-emitting layer on the hole transport region; The electron transport region on the light-emitting layer; and The second electrode on the electron transport region.

10. The organic electroluminescent device of claim 9, wherein the hole transport region comprises: Hole injection layer on the first electrode; and Hole transport layer on the hole injection layer, The hole transport layer thereunder comprises an amine compound as described in any one of claims 1 to 8.

11. The organic electroluminescent device of claim 9, wherein the hole transport region comprises multiple layers, and The layer in contact with the light-emitting layer among the plurality of layers comprises an amine compound as described in any one of claims 1 to 8.

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