Light-emitting material, light-emitting device, electronic apparatus, and electronic device

Abstract

A light-emitting material, a light-emitting device, an electronic apparatus, and an electronic device are provided. The luminescent material has a form in which an electron-donating group and an electron-withdrawing group are attached to the benzene and the electron-withdrawing group is located ortho to the electron-donating group.

Description

[0001] This application is based upon and claims the benefit of priority of U.S. patent application No. 18 / 349,892, filed on July 10, 2023, which is a continuation-in-part of U.S. patent application No. 18 / 166,431, filed on February 8, 2023, which is a continuation-in-part of U.S. patent application No. 15 / 562,415, filed on January 15, 2018, the disclosures of which are incorporated herein by reference in their entirety. Technical Field

[0002] Example embodiments of the present disclosure relate to a compound for an organic light emitting diode, and more particularly, to a thermally activated delayed fluorescent material as a compound for an organic light emitting diode. Background Art

[0003] OLED (Organic Light Emitting Device) is a self-emitting device, and has advantages of fast response time, excellent or appropriate brightness, driving voltage and response rate characteristics, and realization of multi-color as well as wide viewing angle and excellent or appropriate contrast.

[0004] A typical organic light emitting diode may include an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and / or an electron injection layer, etc. When a voltage is applied between the anode and the cathode, holes injected from the anode move to the light emitting layer via the hole transport layer, and electrons injected from the cathode move to the light emitting layer via the electron transport layer. Carriers (such as holes and electrons) recombine in the light emitting layer to generate excitons, and the excitons transition to the ground state to emit light.

[0005] The excitons generated when an organic light-emitting diode is driven are presumably in a singlet state of 25% and a triplet state of 75%. In the case of fluorescent light-emitting materials, only 25% of the excitons in the singlet state of the total excitons participate in the emission, and the internal quantum efficiency remains at a maximum of 25%. In order to improve these properties, iridium complexes or platinum complexes that promote emission from triplet excitons can be used, thereby allowing excellent or suitable quantum efficiency characteristics. However, these materials are expensive, and their application is limited due to the instability of blue light-emitting materials.

[0006] To solve this problem, recently, thermally activated delayed fluorescent organic materials are being developed. Thermally activated delayed fluorescent organic materials have an energy difference of 0.3 eV or less between the singlet and triplet states of excitons. In this case, up-conversion from triplet to singlet is allowed by heat corresponding to room temperature or device driving temperature, and a theoretical quantum efficiency close to 100% can be achieved. Summary of the invention

[0007] Technical issues

[0008] It is known that the actual quantum efficiency of currently developed thermally activated delayed fluorescent organic materials is very different from the theoretical quantum efficiency and still needs to be improved.

[0009] Technical Solution

[0010] An object of example embodiments of the present disclosure is to provide a thermally activated delayed fluorescent material and an organic light emitting diode including the same, which can improve quantum efficiency because a transition from a triplet state to a singlet state can be performed more efficiently.

[0011] In some example embodiments, a thermally activated delayed fluorescence (TADF) material is provided. The TADF material has a form in which an electron donating group and an electron withdrawing group are attached to benzene and the electron withdrawing group is located at an ortho position to the electron donating group.

[0012] Beneficial Effects

[0013] According to example embodiments of the present disclosure, since a compound having an electron donating group and an electron withdrawing group introduced at the ortho position of a benzene ring can have a reduced energy difference between a singlet excited state and a triplet excited state, up-conversion from a triplet excited state to a singlet excited state by reverse intersystem crossing caused by heat generated at room temperature or a device operating temperature can easily occur, which can lead to delayed fluorescence. BRIEF DESCRIPTION OF THE DRAWINGS

[0014] Example embodiments of the present disclosure will become more apparent by describing in more detail example embodiments of the present disclosure with reference to the accompanying drawings, in which:

[0015] Figure 1 is a cross-sectional view showing an organic light emitting diode according to an example embodiment of the present disclosure;

[0016] Figure 2 shows the distribution of molecular orbitals of Compound 1, Comparative Compound 2 and Comparative Compound 3 prepared according to Synthesis Example 1;

[0017] Figure 3 is a schematic cross-sectional view of a light emitting device according to an embodiment;

[0018] Figure 4 and Figure 5 is a cross-sectional view of an electronic device according to an embodiment;

[0019] Figure 6 is a schematic perspective view of an electronic device including a light emitting device according to an embodiment;

[0020] Figure 7is a schematic diagram showing the exterior of a vehicle as an electronic device including a light emitting device according to an embodiment; and

[0021] Fig. 8A , Figure 8B and Figure 8C is a schematic diagram showing the interior of a vehicle according to an embodiment. DETAILED DESCRIPTION

[0022] Hereinafter, the present disclosure will be described in more detail with reference to multiple aspects and one or more suitable example embodiments. Hereinafter, example embodiments of the present disclosure will be described in more detail with reference to the accompanying drawings. The embodiments to be described may be modified in a variety of different forms, and the scope of the present disclosure is not limited to the embodiments. On the contrary, embodiments are provided to further accurately and fully explain the present disclosure, and to fully convey the scope of the present disclosure to those skilled in the art. In the accompanying drawings, the same reference numerals represent the same elements.

[0023] As used herein, unless otherwise defined, the term "alkyl" refers to an aliphatic hydrocarbon group. An alkyl group may be a saturated alkyl group that does not contain any double or triple bonds. Alternatively, an alkyl group may be an unsaturated alkyl group that includes at least one double or triple bond. Whether saturated or unsaturated, an alkyl group may be branched, straight chain, or cyclic. An alkyl group may be C 1 To C 30 More specifically, the alkyl group may be C 1 To C 10 Alkyl or C 1 To C 6 Alkyl. For example, C 1 To C 4 The alkyl group may be selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.

[0024] As utilized herein, unless otherwise defined, the term "aryl" refers to a monocyclic aromatic group or a polycyclic aromatic group consisting of fused aromatic rings, and includes heteroaryl groups.

[0025] As utilized herein, unless otherwise defined, "heteroaryl" is a monocyclic aromatic group or a polycyclic aromatic group consisting of fused aromatic rings containing at least one heteroatom selected from the group consisting of N, O, S, Se and P in at least one ring.

[0026] As utilized herein, unless otherwise defined, the term "halogen group" refers to a Group VII element, such as F, Cl, Br, or I. As an example, the halogen group may be F.

[0027] When "Cx-Cy" is described in this specification, the number of carbon atoms corresponding to all integers between x and y will also be interpreted as what is described.

[0028] Thermally Activated Delayed Fluorescence (TADF) Materials

[0029] The following Chemical Formula 1 represents a compound according to an exemplary embodiment of the present disclosure.

[0030] Chemical formula 1

[0031]

[0032] In Chemical Formula 1,

[0033] R EDG It can be an electron donating group,

[0034] R EWG It can be an electron withdrawing group,

[0035] R 5 To R 8 can be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 9 Alkyl, substituted or unsubstituted C 5 -C 30 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 7 -C 30 Alkaryl, substituted or unsubstituted C 7 -C 30 Arylalkyl, substituted or unsubstituted C 3 -C 30 a heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylamine group (e.g., a substituted or unsubstituted fused arylamine group), a substituted or unsubstituted phosphine group or phosphine oxide group, a substituted or unsubstituted thiol group, a substituted or unsubstituted sulfoxide group or sulfone group.

[0036] The electron donating group may be a substituted or unsubstituted amine group, and the electron withdrawing group may be a substituted or unsubstituted triazine group.

[0037] The compound represented by Chemical Formula 1 may be a light-emitting material. For example, it may be a thermally activated delayed fluorescence (TADF) material that exhibits thermally activated delayed fluorescence. More specifically, it may be used as a light-emitting dopant in an organic light-emitting device. However, it is not limited thereto, and it may be used in any layer in an organic light-emitting device, or may also be used as a host material in a light-emitting layer.

[0038] The compound represented by Chemical Formula 1 has a form in which an electron-donating group and an electron-withdrawing group are combined with benzene, and the electron-withdrawing group is located in the adjacent position (ortho position) of the electron-donating group. Therefore, by introducing the steric hindrance effect of the electron-donating group and the electron-withdrawing group at the ortho position relative to each other of benzene, the overlap of HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) can be controlled and the difference between the singlet energy (S1) and the triplet energy (T1) can be reduced. For example, since the compound having the electron-donating group and the electron-withdrawing group introduced at the ortho position of the benzene ring has the energy difference (less than 0.3 eV) between the singlet excited state and the triplet excited state that is minimized or reduced, the triplet excited state of the reverse intersystem crossing caused by the heat generated at room temperature or the device operating temperature can be easily converted to the singlet excited state, which can cause delayed fluorescence.

[0039] Specific examples of the compound represented by Chemical Formula 1 may be represented by any one of Chemical Formulas 2 to 4 below.

[0040] Chemical formula 2

[0041]

[0042] Chemical formula 3

[0043]

[0044] Chemical formula 4

[0045]

[0046] In Chemical Formulae 2 to 4, R 1 To R 12 can independently represent substituted or unsubstituted C 1 -C 9 Alkyl, substituted or unsubstituted C 5 -C 30 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 7 -C 30 Alkaryl, substituted or unsubstituted C 7 -C 30 Arylalkyl or substituted or unsubstituted C 3 -C 30 Heteroaryl; R 1 and R 2 , R 3 and R 4 , R 5 and R 6 , R 7 and R 8 , R9 and R 10 or R 11 and R 12 may optionally be combined with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heteroaryl group. 1 and R 2 may be combined with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl.

[0047] In Chemical Formulae 2 to 4, R 17 To R 19 The functional groups may be connected to the triazine group via carbon, nitrogen, oxygen, silicon, sulfur or phosphorus and are independently cyano, substituted or unsubstituted C 1 -C 9 Alkyl, substituted or unsubstituted C 5 -C 30 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 7 -C 30 Alkaryl, substituted or unsubstituted C 7 -C 30 Arylalkyl, substituted or unsubstituted C 3 -C 30 Heteroaryl, substituted or unsubstituted C 1 -C 30 Alkoxy, substituted or unsubstituted C 6 -C 30 Aryloxy, C 1 -C 9 Alkylsilyl or substituted or unsubstituted -NR a R b . R a and R b can be independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C 1 -C 9 Alkyl, substituted or unsubstituted C 5 -C 30 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 7 -C 30 Arylalkyl and substituted or unsubstituted C 3 -C 30 Heteroaryl. a and R b The groups may optionally be combined with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl.

[0048] R 22 To R 45 Each of the above R 5 To R 8 For example, R 22 To R 45 may be independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted C 4 -C 6 heteroaryl, substituted or unsubstituted phenyl or substituted or unsubstituted C 1 -C 3 Here, the substituted C 1 -C 3 The alkyl group may be halogen-substituted C 1 -C 3 The alkyl group may be F. For example, in Formula 2, R 22 To R 25 may independently be hydrogen or deuterium.

[0049] In chemical formula 2, R 1 , R 2 , R 17 and R 18 At least one of may include deuterium, or R 22 To R 25 At least one of may be deuterium.

[0050] The electron donating group in Chemical Formula 1 or -NR in Chemical Formulas 2 to 4 1 R 2 、-NR 3 R 4 、-NR 5 R 6 、-NR 7 R 8 、-NR 9 R 10 or -NR 11 R 12 can be independently any one of the structural formulas A1 to A19, for example, A6, A8, A9 or A10. For example, in Chemical Formula 2, R 1 and R 2 may be combined together with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heteroaryl group represented by any one of Structural Formulas A1 to A6 and A9 to A19:

[0051]

[0052]

[0053] In structural formulas A1 to A19,

[0054] R 1 The same as R in the above chemical formula 2 1 same,

[0055] R 11 To R 14 can be independently hydrogen, deuterium, substituted or unsubstituted C 1 -C 2 Alkyl or substituted or unsubstituted C 6 -C 30 Aryl,

[0056] Sub 1 and Sub 2 may be independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 -C 9 Alkyl, substituted or unsubstituted C 5 -C 30 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 7 -C 30 Alkaryl, substituted or unsubstituted C 3 -C 30 Heteroaryl, substituted or unsubstituted C 1 -C 9 Alkoxy, substituted or unsubstituted -NR c R d , substituted or unsubstituted silyl, substituted or unsubstituted phosphine, substituted or unsubstituted phosphine oxide, substituted or unsubstituted thiol, substituted or unsubstituted sulfoxide, substituted or unsubstituted sulfone, substituted or unsubstituted C 6 -C 30 Arylsilyl, substituted or unsubstituted C 6 -C 30 Arylthio, substituted or unsubstituted C 6 -C 30 Aryloxy, substituted or unsubstituted C 6 -C 30 Aromatic amino or substituted or unsubstituted C 7 -C 30 For example, in Formula 2, Sub 1 and Sub 2 can be independently hydrogen, deuterium, a halogen group or a cyano group. 1 and Sub 2Can exist in multiple quantities independently of each other. For example, Sub 1 and Sub 2 Can be present in a number of 2, 3, 4 or 5 independently of each other. c and R d can be independently selected from the group consisting of: substituted or unsubstituted C 1 -C 9 Alkyl, substituted or unsubstituted C 5 -C 30 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 7 -C 30 Arylalkyl and substituted or unsubstituted C 3 -C 30 Heteroaryl. c and R d may optionally be linked together with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl. 1 and Sub 2 may be optionally fused to the subject to which they are bound independently of each other to form a substituted or unsubstituted cyclic group or a substituted or unsubstituted aryl group. 1 and Sub 2 At least one of them is a substituted or unsubstituted C 6 -C 30 Arylsilyl, substituted or unsubstituted C 6 -C 30 Arylthio, substituted or unsubstituted C 6 -C 30 Aryloxy, substituted or unsubstituted C 6 -C 30 Aromatic amino or substituted or unsubstituted C 7 -C 30 In the case of an aralkyl group, an aryl group contained therein may be fused to the main body to form a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heteroaryl group.

[0057] The electron donating group in Chemical Formula 1 or -NR in Chemical Formulas 2 to 4 1 R 2 、-NR 3 R 4 、-NR 5 R 6 、-NR 7 R 8 、-NR 9 R 10 and-NR 11 R 12The structural formula A9 may be any one of the structural formulas A20 to A38 independently of each other. Specifically, the structural formula A9 may be any one of the following structural formulas A20 to A38.

[0058]

[0059] In structural formulas A20 to A38,

[0060] R 11 and R 12 can be independently hydrogen, deuterium, substituted or unsubstituted C 1 -C 2 Alkyl or substituted or unsubstituted C 6 -C 30 Aryl,

[0061] Sub 1 To Sub 4 may be independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 -C 9 Alkyl, substituted or unsubstituted C 5 -C 30 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 7 -C 30 Alkaryl, substituted or unsubstituted C 7 -C 30 Arylalkyl, substituted or unsubstituted C 3 -C 30 Heteroaryl, substituted or unsubstituted C 1 -C 9 Alkoxy, substituted or unsubstituted C 6 -C 30 aryloxy, substituted or unsubstituted silyl, substituted or unsubstituted phosphine, substituted or unsubstituted phosphine oxide, substituted or unsubstituted thiol, substituted or unsubstituted sulfoxide or substituted or unsubstituted sulfone. 1 To Sub 4 can be independently hydrogen, deuterium, a halogen group or a cyano group. 1 To Sub 4 Can exist in multiple quantities independently of each other. For example, Sub 1 To Sub 4 Can be present in a number of 2, 3 or 4 independently of each other.

[0062] The electron donating group in Chemical Formula 1 or -NR in Chemical Formulas 2 to 4 1 R 2、-NR 3 R 4 、-NR 5 R 6 、-NR 7 R 8 、-NR 9 R 10 and-NR 11 R 12 The structural formula A10 may be any one of the structural formulas A39 to A45 independently of each other. Specifically, the structural formula A10 may be any one of the following structural formulas A39 to A45.

[0063]

[0064] In structural formulas A39 to A45,

[0065] R 11 To R 14 can be independently hydrogen, deuterium, substituted or unsubstituted C 1 -C 2 Alkyl or substituted or unsubstituted C 6 -C 30 Aryl,

[0066] Sub 1 To Sub 4 may be independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 -C 9 Alkyl, substituted or unsubstituted C 5 -C 30 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 7 -C 30 Alkaryl, substituted or unsubstituted C 7 -C 30 Arylalkyl, substituted or unsubstituted C 3 -C 30 Heteroaryl, substituted or unsubstituted C 1 -C 9 Alkoxy, substituted or unsubstituted C 6 -C 30 aryloxy, substituted or unsubstituted silyl, substituted or unsubstituted phosphine, substituted or unsubstituted phosphine oxide, substituted or unsubstituted thiol, substituted or unsubstituted sulfoxide or substituted or unsubstituted sulfone. 1 To Sub 4 can be independently hydrogen, deuterium, a halogen group or a cyano group. 1 To Sub4 Can exist in multiple quantities independently of each other. For example, Sub 1 To Sub 4 Can be present in a number of 2, 3 or 4 independently of each other.

[0067] In formula 2, R 17 and R 18 Examples of may be independently cyano, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 heteroaryl or substituted or unsubstituted -NR a R b , and R a and R b can be independently hydrogen, deuterium, substituted or unsubstituted C 1 -C 9 Alkyl, substituted or unsubstituted C 5 -C 30 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 7 -C 30 Arylalkyl or substituted or unsubstituted C 3 -C 30 heteroaryl; and R a and R b The groups may optionally be combined with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl.

[0068] The electron withdrawing group in Chemical Formula 1 or the substitution group in Chemical Formula 2 is R 17 and R 18 Examples of the triazine group may be the same as the following structural formulas B1 to B14, structural formula B50 and structural formula B51. For example, in chemical formula 2, the substitution is R 17 and R 18 The triazine group may be the same as any one of Structural Formulas B8 to B12, Structural Formula B50, and Structural Formula B51.

[0069]

[0070] In formulae B1 to B14, B50 and B51,

[0071] R 11 and R 12 may be independently hydrogen, deuterium or substituted or unsubstituted C 1 -C 2alkyl,

[0072] Sub 5 and Sub 6 may be independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 -C 9 Alkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 Heteroaryl, substituted or unsubstituted C 1 -C 9 Alkoxy, substituted or unsubstituted -NR e R f , substituted or unsubstituted silyl, substituted or unsubstituted phosphine, substituted or unsubstituted phosphine oxide, substituted or unsubstituted thiol, substituted or unsubstituted sulfoxide, substituted or unsubstituted sulfone, substituted or unsubstituted C 6 -C 30 Arylthio, substituted or unsubstituted C 6 -C 30 Aryloxy, substituted or unsubstituted C 6 -C 30 Aromatic amino or substituted or unsubstituted C 7 -C 30 Aralkyl. In addition, Sub 5 and Sub 6 Can exist in multiple quantities independently of each other. For example, Sub 5 and Sub 6 Can be present in the number of 2, 3, 4, 5, 6, 7 or 8 independently of each other. In addition, Sub 5 and Sub 6 may be optionally fused to the subject to which they are bound independently of each other to form a substituted or unsubstituted cyclic group or a substituted or unsubstituted aryl group. 5 or Sub 6 is substituted or unsubstituted C 6 -C 30 Arylthio, substituted or unsubstituted C 6 -C 30 Aryloxy, substituted or unsubstituted C 6 -C 30 Aromatic amino or substituted or unsubstituted C 7 -C 30 In the case of an aralkyl group, an aryl group contained therein may be fused to the main body to form a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heteroaryl group.

[0073] R e and R fmay be independently selected from the group consisting of: substituted or unsubstituted C 1 -C 9 Alkyl, substituted or unsubstituted C 5 -C 30 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 7 -C 30 Alkaryl, substituted or unsubstituted C 7 -C 30 Arylalkyl or substituted or unsubstituted C 3 -C 30 Heteroaryl. e and R f may optionally be linked together with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl.

[0074] The electron withdrawing group in the above chemical formula 1 or the substitution with R in the above chemical formula 2 17 and R 18 Examples of the triazine group may be the same as the following structural formulas B15 to B27. Specifically, structural formula B12 may be any one of the following structural formulas B15 to B27.

[0075]

[0076]

[0077] In structural formulas B15 to B27,

[0078] R 11 and R 12 may be independently hydrogen, deuterium or substituted or unsubstituted C 1 -C 2 alkyl.

[0079] In the above chemical formula 2, the substitutions are R 17 and R 18 Examples of the triazine group may be the same as the following Structural Formula B12 and Structural Formula B50 to Structural Formula B54.

[0080]

[0081] In formula B12 and formulas B50 to B54,

[0082] Sub 5 To Sub 8 may be independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 6 -C30 Aryl or substituted or unsubstituted C 3 -C 30 Heteroaryl. For example, Sub 7 and Sub 8 may independently be hydrogen, deuterium, a halogen group or a cyano group.

[0083] In the above chemical formula 3, the substitutions are R 19 Examples of the triazine group may be the same as the following Structural Formulas B28 to B49.

[0084]

[0085] In structural formulas B28 to B49,

[0086] R 11 and R 12 independently represents hydrogen, deuterium or substituted or unsubstituted C 1 -C 2 alkyl.

[0087] A specific example of the compound represented by Chemical Formula 2 may be represented by Chemical Formula 5 below, and a specific example of the compound represented by Chemical Formula 3 may be represented by Chemical Formula 6 below.

[0088] Chemical formula 5

[0089]

[0090] In Chemical Formula 5, R 1 , R 2 and R 22 To R 25 As defined in Chemical Formula 2, and specifically, -NR 1 R 2 It may be any one of Structural Formulas A1 to A45, for example, A6, A9 or A10.

[0091] In chemical formula 5, Sub 5 and Sub 6 It can be as defined in Structural Formula B12 and Structural Formula B50 to Structural Formula B54. As an example, Sub 5 and Sub 6 At least one of them can be -NR e R f For example, when Sub 5 or Sub 6 Yes - NR e R f And-NR e R fWhen the triazine group is located at the ortho position, the compound of Chemical Formula 5 may be the same as the compound represented by Chemical Formula 6. 5 and Sub 6 The two in it are -NR e R f And these two-NR e R f The compound of Chemical Formula 5 may be the same as the compound represented by Chemical Formula 4 when both are located at the ortho position relative to the triazine group.

[0092] As an example, an example of the triazine group in the above Chemical Formula 5 may be the same as any one of the above Structural Formulas B12 and B15 to B27.

[0093] As an example, an example of the triazine group in the above Chemical Formula 5 may be the same as any one of the above Structural Formula B12 and Structural Formulas B50 to B54.

[0094] Chemical formula 6

[0095]

[0096] In Chemical Formula 6, R 3 , R 4 , R 5 , R 6 , R 26 To R 29 and R 30 To R 33 As defined in Formula 3 above. For example, -NR 3 R 4 and-NR 5 R 6 Independently of each other, it may be any one of the structural formulae A1 to A45, for example, A6, A8, A9 or A10.

[0097] In chemical formula 6, Sub 5 The same as defined in Formula B11. As an example, examples of the triazine group in the above Chemical Formula 6 may be the same as any one of the above Formulas B34 to B47.

[0098] Specific examples of the compound represented by Chemical Formula 2 may be represented by any one of Chemical Formulas 7 to 10 below.

[0099] Chemical formula 7

[0100]

[0101] Chemical formula 8

[0102]

[0103] Chemical formula 9

[0104]

[0105] Chemical formula 10

[0106]

[0107] A specific example of the compound represented by Chemical Formula 3 may be represented by Chemical Formula 11 below.

[0108] Chemical formula 11

[0109]

[0110] A specific example of the compound represented by Chemical Formula 4 may be represented by Chemical Formula 12 below.

[0111] Chemical formula 12

[0112]

[0113] Subsections of Formula 7, Formula 11 and Formula 12 above 1 and Sub 2 It can be as defined in Structural Formula A9. As an example, the above Chemical Formulas 7, 11 and 12 include Sub 1 and Sub 2 The carbazole group of can be any one of the above structural formulas A20 to A38. 1 and Sub 2 It can be as defined in Structural Formula A8. Sub 1 and Sub 2 It may be as defined in Structural Formula A6. Substituents of Formula 10 1 and Sub 2 It can be as defined in Structural Formula A10. As an example, the Sub 1 and Sub 2 The acridine group may be any one of Structural Formulas A39 to A45.

[0114] In the above Chemical Formulae 7 to 10, R 17 and R 18 It may be as defined in the above chemical formula 2. As an example, it includes R 17 and R 18 The triazine group may be any one of the above-mentioned structural formulas B1 to B27. 17 and R 18The triazine group may be any one of the above-mentioned structural formulas B12 and B50 to B54. In Chemical Formula 11, R 19 It may be the same as defined in Chemical Formula 3. As another example, 19 The triazine group may be any one of the above structural formulas B28 to B49.

[0115] In Chemical Formulae 7 to 12, R 22 To R 45 can be independently combined with R defined in the above chemical formula 1 5 To R 8 , but specifically, R 22 To R 45 independently represents hydrogen, deuterium, a halogen group, a substituted or unsubstituted C 4 -C 6 heteroaryl, substituted or unsubstituted phenyl or substituted or unsubstituted C 1 -C 3 Here, the substituted C 1 -C 3 The alkyl group may be halogen-substituted C 1 -C 3 The alkyl group may be F. For example, in Chemical Formulae 7 to 10, R 22 To R 25 may independently be hydrogen or deuterium.

[0116] In the above chemical formula 10, R 11 and R 12 may be independently hydrogen, deuterium or substituted or unsubstituted C 1 -C 2 alkyl.

[0117] The thermally activated delayed fluorescent material can realize red, green, and blue emission colors by appropriately or properly introducing an electron donating group and an electron withdrawing group and reducing the difference between the singlet energy and the triplet energy to 0.3 eV or less.

[0118] Specific compounds of such a thermally activated delayed fluorescent material are represented by the following Compound 1 to Compound 122, but are not limited thereto.

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127] Compounds 1 to 21, 31 to 45, 52, 53, 55 to 60, 67 to 74, 81 to 86, and 93 to 122 may be examples of the compounds shown in Chemical Formula 7, compounds 22 to 30, 46 to 48, 75 to 78, and 89 to 92 may be examples of the compounds shown in Chemical Formula 8, compound 49, 50, 61 to 66, 87, and 88 may be examples of the compounds shown in Chemical Formula 9, compound 51, 54, 79, and 80 may be examples of the compounds shown in Chemical Formula 10, compounds 67 to 74 may be examples of the compounds shown in Chemical Formula 11, and compounds 83 to 86 may be examples of the compounds shown in Chemical Formula 12.

[0128] Figure 3 Description

[0129] Figure 3 1 is a schematic cross-sectional view of a light emitting device 10 according to an embodiment. The light emitting device 10 may include a first electrode 110 , an intermediate layer 130 , and a second electrode 150 .

[0130] In the following, reference will be made to Figure 3 The structure of the light emitting device 10 and a method of manufacturing the light emitting device 10 according to the embodiment are described.

[0131] First electrode 110

[0132] exist Figure 3 In the embodiment, the substrate may also be included under the first electrode 110 and / or on the second electrode 150. In an embodiment, the substrate may be a glass substrate and / or a plastic substrate. In an embodiment, the substrate may be a flexible substrate. For example, the flexible substrate may include a plastic having excellent heat resistance and durability (such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof).

[0133] The first electrode 110 may be formed by applying a material for forming the first electrode 110 onto a substrate using a deposition method or a sputtering method. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be a high work function material to facilitate injection of holes.

[0134] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), or any combination thereof. When the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0135] The first electrode 110 may have a structure including (eg, consisting of) a single layer or a structure including a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.

[0136] Middle layer 130

[0137] The intermediate layer 130 may be disposed on the first electrode 110. The intermediate layer 130 may include an emission layer.

[0138] The intermediate layer 130 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 150 .

[0139] In addition to one or more suitable organic materials, the intermediate layer 130 may further include metal-containing compounds (such as organometallic compounds) and / or inorganic materials (such as quantum dots), etc.

[0140] The intermediate layer 130 may include: two or more emission units stacked between the first electrode 110 and the second electrode 150; and at least one charge generation layer located between the two or more emission units. When the intermediate layer 130 includes two or more emission units and at least one charge generation layer as described herein, the light emitting device 10 may be a tandem light emitting device.

[0141] Hole transport region in the intermediate layer 130

[0142] The hole transport region may have: a structure including (e.g., consisting of) a layer including (e.g., consisting of) a single material; a structure including (e.g., consisting of) a layer including different materials; or a structure including a plurality of layers including different materials.

[0143] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof.

[0144] In an embodiment, the hole transport region may have a multilayer structure including a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure or a hole injection layer / hole transport layer / emission auxiliary layer structure, wherein the layers of each structure may be stacked from the first electrode 110 in their corresponding stated order, but the structure of the hole transport region is not limited thereto.

[0145] The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:

[0146] Formula 201

[0147]

[0148] Formula 202

[0149]

[0150] In equation 201 and equation 202,

[0151] L 201 To L 204 may be independently unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,

[0152] L 205 Can be *-O-*', *-S-*', *-N(Q 201 )-*', unsubstituted or substituted with at least one R 10a C 1 -C 20 Alkylene, unsubstituted or substituted with at least one R 10a C 2 -C 20 Alkenylene, unsubstituted or substituted with at least one R 10a C3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,

[0153] xa1 to xa4 may each independently be an integer from 0 to 5,

[0154] xa5 can be an integer from 1 to 10,

[0155] R 201 To R 204 and Q 201 may be independently unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,

[0156] R 201 and R 202 may be optionally substituted via a single bond, unsubstituted or substituted with at least one R 10a C 1 -C 5 The alkylene group is either unsubstituted or substituted with at least one R 10a C 2 -C 5 The alkenylene groups are connected to each other to form an unsubstituted or substituted group having at least one R 10a C 8 -C 60 Polycyclic groups (eg, carbazole groups, etc.) (eg, see compound HT16),

[0157] R 203 and R 204 may be optionally substituted via a single bond, unsubstituted or substituted with at least one R 10a C 1 -C 5 The alkylene group is either unsubstituted or substituted with at least one R 10a C 2 -C 5 The alkenylene groups are connected to each other to form an unsubstituted or substituted group having at least one R 10a C 8 -C 60 Polycyclic groups, and

[0158] na1 can be an integer from 1 to 4.

[0159] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each independently include at least one of the groups represented by Formulas CY201 to CY217:

[0160]

[0161] In formula CY201 to formula CY217, R 10b and R 10c can be independently related to R 10a Same as described herein, CY 201 To Ring CY 204 can be independently C 3 -C 20 Carbocyclic or C 1 -C 20 In the heterocyclic group, at least one hydrogen in Formula CY201 to Formula CY217 may be unsubstituted or replaced by R 10a replace.

[0162] In the embodiment, in Formula CY201 to Formula CY217, ring CY 201 To Ring CY 204 Each of them may independently be a benzene group, a naphthyl group, a phenanthrene group or an anthracene group.

[0163] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each independently include at least one of the groups represented by Formulae CY201 to CY203.

[0164] In an embodiment, the compound represented by Formula 201 may include at least one of the groups represented by Formulas CY201 to CY203 and at least one of the groups represented by Formulas CY204 to CY217.

[0165] In an embodiment, in formula 201, xa1 may be 1, R 201 It can be a group represented by one of the formulas CY201 to CY203, xa2 can be 0, R 202 It may be a group represented by one of Formula CY204 to Formula CY207.

[0166] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may both not include a group represented by one of Formula CY201 to Formula CY203.

[0167] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may both not include a group represented by one of Formula CY201 to Formula CY203, and may each independently include at least one of groups represented by Formula CY204 to Formula CY217.

[0168] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may both not include a group represented by one of Formulas CY201 to CY217.

[0169] In an embodiment, the hole transport region may include at least one selected from compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA) and polyaniline / poly(4-styrenesulfonate) (PANI / PSS), and / or any combination thereof:

[0170]

[0171]

[0172]

[0173]

[0174] The thickness of the hole transport region can be about to about For example, the thickness of the hole transport region may be in the range of about to about When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be about to about In the range of to about For example, the thickness of the hole injection layer can be about to about For example, the thickness of the hole transport layer can be about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.

[0175] The emission auxiliary layer can compensate the optical resonance distance according to the wavelength of the light emitted from the emission layer so that the luminous efficiency can be improved. The electron blocking layer can prevent or reduce the leakage of electrons from the emission layer to the hole transport region. The material that can be included in the hole transport region can be included in the emission auxiliary layer and the electron blocking layer.

[0176] p-dopant

[0177] In addition to these materials, the hole transport region may further include a charge generating material for improving conductive properties. The charge generating material may be dispersed uniformly or non-uniformly in the hole transport region (eg, in the form of a single layer composed of the charge generating material).

[0178] The charge generating material may be, for example, a p-dopant.

[0179] For example, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant can be equal to or less than about -3.5 eV.

[0180] In an embodiment, the p-dopant may include a quinone derivative, a cyano-containing compound, a compound including the element EL1 and the element EL2, or any combination thereof.

[0181] Examples of quinone derivatives may include TCNQ, F 4 -TCNQ, etc.

[0182] Examples of cyano-containing compounds may include HAT-CN and a compound represented by Formula 221:

[0183]

[0184] Formula 221

[0185]

[0186] In formula 221,

[0187] R 221 To R 223 may be independently unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 a heterocyclic group, and

[0188] R 221 To R 223 At least one of them may be independently C substituted with the following groups 3 -C 60 Carbocyclic or C 1 -C60 Heterocyclic group: cyano; -F; -Cl; -Br; -I; C substituted with cyano, -F, -Cl, -Br, -I or any combination thereof 1 -C 20 or any combination thereof.

[0189] In the compound including the element EL1 and the element EL2, the element EL1 may be a metal, a metalloid, or any combination thereof, and the element EL2 may be a nonmetal, a metalloid, or any combination thereof.

[0190] Examples of metals may include alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), etc. (e.g., tantalum (Tb), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.).

[0191] Examples of metalloids may include silicon (Si), antimony (Sb), and tellurium (Te).

[0192] Examples of non-metals may include oxygen (O) and halogens (eg, F, Cl, Br, I, etc.).

[0193] Examples of compounds including element EL1 and element EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, or metal iodides), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, or metalloid iodides), metal tellurides, or any combination thereof.

[0194] Examples of metal oxides may include tungsten oxide (eg, WO, W 2 O 3 , WO 2 , WO 3 , W 2 O 5 etc.), vanadium oxides (e.g., VO, V2 O 3 , VO 2 、V 2 O 5 etc.), molybdenum oxide (MoO, Mo 2 O 3 、MoO 2 、MoO 3 、Mo 2 O 5 etc.) and rhenium oxide (e.g., ReO 3 wait).

[0195] Examples of the metal halide may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and lanthanide metal halides.

[0196] Examples of alkali metal halides may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.

[0197] Examples of alkaline earth metal halides may include BeF 2 MgF 2 , CaF 2 , SrF 2 , BaF 2 、BeCl 2 MgCl 2 , CaCl 2 、SrCl 2 、BaCl 2 ,BeBr 2 MgBr 2 , CaBr 2 , SrBr 2 ,BaBr 2 ,BeI 2 MgI 2 ,CaI 2 , SrI 2 and BaI 2 .

[0198] Examples of transition metal halides may include titanium halides (eg, TiF 4 、TiCl 4 、TiBr 4 、TiI 4 etc.), zirconium halides (e.g., ZrF 4 、ZrCl 4 , ZrBr 4 , ZrI 4etc.), hafnium halides (e.g., HfF 4 , HfCl 4 , HfBr 4 , HfI 4 etc.), vanadium halides (e.g., VF 3 、VCl 3 , VBr 3 VI 3 etc.), niobium halides (e.g., NbF 3 、NbCl 3 , NbBr 3 , NbI 3 etc.), tantalum halides (e.g., TaF 3 、TaCl 3 、TaBr 3 、TaI 3 etc.), chromium halides (e.g., CrF 3 CrCl 3 CrBr 3 CrI 3 etc.), molybdenum halides (e.g., MoF 3 、MoCl 3 、MoBr 3 、MoI 3 etc.), tungsten halides (e.g., WF 3 、WCl 3 , WBr 3 , WI 3 etc.), manganese halides (e.g., MnF 2 、MnCl 2 、MnBr 2 、MnI 2 etc.), technetium halides (e.g., TcF 2 , TcCl 2 、TcBr 2 , TcI 2 etc.), rhenium halides (e.g., ReF 2 、ReCl 2 、ReBr 2 、ReI 2 etc.), ferrous halides (e.g., FeF 2 、FeCl 2 , FeBr 2 ,FeI 2 etc.), ruthenium halides (e.g., RuF 2 、RuCl 2 ,RuBr 2 , RuI 2 etc.), osmium halides (e.g., OsF 2 , OsCl 2 、OsBr 2, OsI 2 etc.), cobalt halides (e.g., CoF 2 、CoCl 2 ,CoBr 2 、CoI 2 etc.), rhodium halides (e.g., RhF 2 , RhCl 2 , RhBr 2 , RhI 2 etc.), iridium halides (e.g., IrF 2 、IrCl 2 ,IrBr 2 ,IrI 2 etc.), nickel halides (e.g., NiF 2 、NiCl 2 、NiBr 2 , NiI 2 etc.), palladium halides (e.g., PdF 2 , PdCl 2 , PdBr 2 , PdI 2 etc.), platinum halides (e.g., PtF 2 、PtCl 2 , PtBr 2 , PtI 2 etc.), cuprous halides (e.g., CuF, CuCl, CuBr, CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.), and gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.).

[0199] Examples of late transition metal halides may include zinc halides (e.g., ZnF 2 、ZnCl 2 、ZnBr 2 、ZnI 2 etc.), indium halides (e.g., InI 3 etc.) and tin halides (e.g., SnI 2 wait).

[0200] Examples of lanthanide metal halides may include YbF, YbF 2 , YbF 3 、SmF 3 , YbCl, YbCl 2 YbCl 3 、SmCl 3 , YbBr, YbBr 2 , YbBr 3 、SmBr 3 、YbI、YbI 2 ,YbI 3and / or SmI 3 wait.

[0201] Examples of metalloid halides may include antimony halides (eg, SbCl 5 wait).

[0202] Examples of metal tellurides may include alkali metal tellurides (eg, Li 2 Te、Na 2 Te, K 2 Te、Rb 2 Te, Cs 2 Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g., TiTe 2 、ZrTe 2 、HfTe 2 、V 2 Te 3 , Nb 2 Te 3 、 2 Te 3 Cr 2 Te 3 、Mo 2 Te 3 , W 2 Te 3 , MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu 2 Te, CuTe, Ag 2 Te, AgTe, Au 2 Te, etc.), late transition metal tellurides (e.g., ZnTe, etc.), and lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).

[0203] Emission layer in the middle layer 130

[0204] When the light emitting device 10 is a full-color light emitting device, the emission layer may be patterned into a red emission layer, a green emission layer and / or a blue emission layer according to the sub-pixel. In an embodiment, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer and a blue emission layer to emit white light, wherein the two or more layers may be in contact with each other or may be separated from each other. In an embodiment, the emission layer may include two or more materials of a red light emitting material, a green light emitting material and a blue light emitting material to emit white light, wherein the two or more materials may be mixed with each other in a single layer.

[0205] The emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.

[0206] The amount of the dopant in the emission layer may be in the range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.

[0207] In an embodiment, the emissive layer may include quantum dots.

[0208] In an embodiment, the emission layer may include a delayed fluorescent material. The delayed fluorescent material may be used as a host or a dopant in the emission layer.

[0209] The thickness of the emission layer can be about to about For example, the thickness of the emission layer can be about to about When the thickness of the emission layer is within these ranges, excellent or suitable light emitting characteristics may be obtained without significantly increasing the driving voltage.

[0210] main body

[0211] In an embodiment, the host may include a compound represented by Formula 301:

[0212] Formula 301

[0213] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .

[0214] In formula 301,

[0215] Ar 301 and L 301 may be independently unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R10a C 1 -C 60 Heterocyclic group,

[0216] xb11 can be 1, 2 or 3,

[0217] xb1 can be an integer from 0 to 5.

[0218] R 301 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O) 2 (Q 301 ) or -P(=O)(Q 301 )(Q 302 ),

[0219] xb21 can be an integer from 1 to 5, and

[0220] Q 301 To Q 303 can be independently compared with the Q 11 Same as described.

[0221] In the embodiment, in Formula 301, when xb11 is 2 or more, two or more Ar 301 can be connected to each other via a single bond.

[0222] In an embodiment, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:

[0223] Formula 301-1

[0224]

[0225] Formula 301-2

[0226]

[0227] In Formula 301-1 and Formula 301-2,

[0228] Ring A 301 To Ring A 304 may be independently unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,

[0229] X 301 Can be O, S, N-[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),

[0230] xb22 and xb23 can each independently be 0, 1 or 2,

[0231] L 301 , xb1 and R 301 may all be the same as described herein,

[0232] L 302 To L 304 can be independently related to L 301 Same as described,

[0233] xb2 through xb4 may each independently be the same as described herein with respect to xb1, and

[0234] R 302 To R 305 and R 311 To R 314 can be independently compared with the 301 Same as described.

[0235] In an embodiment, the host can include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. For example, the host can include a Be complex (eg, compound H55), a Mg complex, a Zn complex, or any combination thereof.

[0236] In an embodiment, the host may include at least one selected from Compound H1 to Compound H128, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), 9,10-di(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-di(9-carbazolyl)benzene (mCP) and 1,3,5-tri(carbazolyl-9-yl)benzene (TCP), and / or any combination thereof:

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244] Phosphorescent dopants

[0245] In an embodiment, the phosphorescent dopant may include at least one transition metal as a central metal.

[0246] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.

[0247] The phosphorescent dopant may be electrically neutral.

[0248] In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 401:

[0249] Formula 401

[0250] M(L 401 ) xc1 (L 402 ) xc2

[0251] Formula 402

[0252]

[0253] In equations 401 and 402,

[0254] M may be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),

[0255] L 401 may be a ligand represented by formula 402, and xc1 may be 1, 2 or 3, wherein when xc1 is two or more, two or more L 401 can be the same or different from each other,

[0256] L 402 can be an organic ligand, and xc2 can be 0, 1, 2, 3 or 4, wherein when xc2 is 2 or greater, two or more L 402 can be the same or different from each other,

[0257] X 401 and X 402 may each independently be nitrogen or carbon,

[0258] Ring A 401 and Ring A 402 can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,

[0259] T 401 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*'、*-C(Q 411 )(Q 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*'or*=C=*',

[0260] X 403 and X 404 can each independently be a chemical bond (eg, a covalent bond or a coordination bond), O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ),

[0261] Q 411 To Q 414 can be independently compared with the Q 11 Same as described,

[0262] R 401 and R 402 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C 1 -C 20 Alkyl, unsubstituted or substituted with at least one R 10a C 1 -C 20 Alkoxy, unsubstituted or substituted with at least one R 10a C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) or -P(=O)(Q 401 )(Q 402 ),

[0263] Q 401 To Q 403 can be independently compared with the Q 11 Same as described,

[0264] xc11 and xc12 may each independently be an integer from 0 to 10, and

[0265] The * and *' in formula 402 both represent the binding site with M in formula 401.

[0266] In an embodiment, in Formula 402, X 401 It can be nitrogen, X 402 It can be carbon, or X 401 and X 402 It may all be nitrogen.

[0267] In an embodiment, in Formula 401, when xc1 is 2 or greater, two or more L 401 The two rings A401 It can be optionally connected via T as a linker 402 connected to each other, and the two rings A 402 It can be optionally connected via T as a linker 403 Connected to each other (see Compound PD1 to Compound PD4 and Compound PD7). 402 and T 403 can be independently related to T 401 Same as described.

[0268] In formula 401, L 402 It can be an organic ligand. In an embodiment, L 402 It may include a halogen group, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), -C(=O), an isonitrile group, a -CN group, a phosphorus-containing group (e.g., a phosphine group, a phosphite group, etc.), or any combination thereof.

[0269] The phosphorescent dopant may include, for example, at least one selected from Compound PD1 to Compound PD39 and / or any combination thereof:

[0270]

[0271]

[0272]

[0273] Fluorescent dopants

[0274] The fluorescent dopant may include an amine-containing compound, a styrene-containing compound, or any combination thereof. In an embodiment, the fluorescent dopant may include a compound represented by Formula 501:

[0275] Formula 501

[0276]

[0277] In formula 501,

[0278] Ar 501 , L 501 To L 503 , R 501 and R 502 may be independently unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,

[0279] xd1 to xd3 may each independently be 0, 1, 2 or 3, and

[0280] xd4 can be 1, 2, 3, 4, 5 or 6.

[0281] In the embodiment, in Formula 501, Ar 501 It may be a condensed ring group in which three or more monocyclic groups are condensed together (for example, anthracene groups, group or pyrene group).

[0282] In an embodiment, in equation 501, xd4 may be 2.

[0283] In an embodiment, the fluorescent dopant may include at least one selected from compounds FD1 to FD37, DPVBi and DPAVBi, and / or any combination thereof:

[0284]

[0285]

[0286]

[0287] Delayed fluorescence material

[0288] The emitting layer may include a delayed fluorescent material.

[0289] In the disclosure, the delayed fluorescent material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.

[0290] The delayed fluorescent material included in the emission layer may serve as a host or as a dopant according to the types (kinds) of other materials included in the emission layer.

[0291] In an embodiment, the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material may be in the range of about 0 eV to about 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material satisfies the above range, the up-conversion of the delayed fluorescent material from the triplet state to the singlet state may effectively occur, and thus, the luminous efficiency of the light emitting device 10 may be improved.

[0292] In an embodiment, the delayed fluorescent material may include: a C-type molecule including at least one electron donor (eg, a π-electron-rich C-type molecule such as a carbazole group); 3 -C 60 cyclic groups, etc.) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group and / or a π-electron-poor nitrogen-containing C 1 -C 60cyclic groups, etc.); and / or materials containing C 8 -C 60 Polycyclic materials, etc., in C 8 -C 60 In the polycyclic group, at least two ring groups are condensed with each other while sharing boron (B).

[0293] Examples of the delayed fluorescent material may include at least one of Compound DF1 to Compound DF14:

[0294]

[0295]

[0296] quantum dots

[0297] The emissive layer may include quantum dots.

[0298] In the specification, the quantum dot may be a crystal of a semiconductor compound, and may include any material capable of emitting light of one or more suitable emission wavelengths according to the size of the crystal.

[0299] The diameter of the quantum dots may, for example, be in the range of about 1 nm to about 10 nm.

[0300] Quantum dots can be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar to these processes.

[0301] The wet chemical process is a method that includes mixing a precursor material with an organic solvent and growing a quantum dot particle crystal. When the quantum dot particle crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot particle crystal and controls the growth of the quantum dot particle crystal, so that the growth of the quantum dot particle crystal can be controlled or selected by a process that is low in cost and can be more easily performed compared to a vapor deposition method such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).

[0302] Quantum dots may include: Group II-VI semiconductor compounds; Group III-V semiconductor compounds; Group III-VI semiconductor compounds; Group I-III-VI semiconductor compounds; Group IV-VI semiconductor compounds; Group IV elements or compounds; or any combination thereof.

[0303] Examples of II-VI semiconductor compounds may include binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, or MgS; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZ nSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe or MgZnS; a quaternary compound such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe or HgZnSTe; or any combination thereof.

[0304] Examples of III-V semiconductor compounds may include binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, or InSb; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, or InPSb; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, or InAlPSb; or any combination thereof. In an embodiment, the III-V semiconductor compound may also include a Group II element. Examples of the Group III-V semiconductor compound also including the Group II element may include InZnP, InGaZnP, InAlZnP, and the like.

[0305] Examples of III-VI semiconductor compounds may include binary compounds such as GaS, GaSe, Ga 2 Se 3 、GaTe、InS、InSe、In 2 S 3 、In 2 Se 3 or InTe; ternary compounds such as InGaS 3 or InGaSe 3 ; and any combination thereof.

[0306] Examples of Group I-III-VI semiconductor compounds may include: ternary compounds such as AgInS, AgInS 2 、CuInS、CuInS 2 、CuGaO 2 、AgGaO 2 or AgAlO 2 ; or any combination thereof.

[0307] Examples of IV-VI semiconductor compounds may include: binary compounds such as SnS, SnSe, SnTe, PbS, PbSe or PbTe; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe or SnPbTe; quaternary compounds such as SnPbSSe, SnPbSeTe or SnPbSTe; or any combination thereof.

[0308] Examples of Group IV elements or compounds may include: single element materials, such as Si or Ge; binary compounds, such as SiC or SiGe; or any combination thereof.

[0309] Each element included in a multi-element compound such as a binary compound, a ternary compound, or a quaternary compound may be present in the particle at a substantially uniform concentration or at a substantially non-uniform concentration.

[0310] In an embodiment, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is substantially uniform, or the quantum dot may have a core-shell structure. In an embodiment, when the quantum dot has a core-shell structure, the material included in the core and the material included in the shell may be different from each other.

[0311] The shell of the quantum dot can be used as a protective layer to prevent chemical denaturation of the core to maintain semiconductor properties, and / or can be used as a charged layer to impart electrophoretic properties to the quantum dot. The shell can be a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient in which the concentration of the material present in the shell decreases toward the core.

[0312] Examples of the shell of the quantum dot may include metal oxides, metalloid oxides, non-metal oxides, semiconductor compounds, or any combination thereof. Examples of metal oxides, metalloid oxides, or non-metal oxides may include: binary compounds such as SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3 , Mn 3 O4 , CuO, FeO, Fe 2 O 3 , Fe 3 O 4 , CoO, Co 3 O 4 or NiO; ternary compounds such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 or CoMn 2 O 4 ; or any combination thereof.

[0313] As described herein, examples of semiconductor compounds may include II-VI semiconductor compounds, III-V semiconductor compounds, III-VI semiconductor compounds, I-III-VI semiconductor compounds, IV-VI semiconductor compounds, or any combination thereof. Examples of semiconductor compounds may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.

[0314] The full width at half maximum (FWHM) of the emission wavelength spectrum of the quantum dot can be equal to or less than about 45nm. For example, the FWHM of the emission wavelength spectrum of the quantum dot can be equal to or less than about 40nm. For example, the FWHM of the emission wavelength spectrum of the quantum dot can be equal to or less than about 30nm. Within these ranges, color purity or color reproducibility can be increased. The light emitted by the quantum dot can be emitted in all directions, so that the wide viewing angle can be improved.

[0315] In embodiments, the quantum dots may be in the form of spherical nanoparticles, pyramidal nanoparticles, multi-armed nanoparticles, cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplates.

[0316] Because the energy band gap can be adjusted by controlling the size of the quantum dots, light with one or more suitable wavelengths can be obtained from the quantum dot emission layer. Therefore, by using quantum dots of different sizes, a light-emitting device that emits light of one or more wavelengths can be realized. In an embodiment, the size of the quantum dots can be selected to emit red light, green light, and / or blue light. In an embodiment, the size of the quantum dots can be configured to emit white light by combining one or more colors of light.

[0317] Electron transport region in the intermediate layer 130

[0318] The electron transport region may have a structure including (eg, consisting of) a layer including (eg, consisting of) a single material; a structure consisting of layers including different materials; or a structure including a plurality of layers including different materials.

[0319] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0320] In an embodiment, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the layers of each structure may be stacked from the emission layer in their corresponding stated order, but the structure of the electron transport region is not limited thereto.

[0321] In an embodiment, the electron transport region (eg, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a nitrogen-containing C 1 -C 60 Metal-free compounds of heterocyclic groups.

[0322] In an embodiment, the electron transport region may include a compound represented by Formula 601:

[0323] Formula 601

[0324] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .

[0325] In formula 601,

[0326] Ar 601 and L 601 may be independently unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,

[0327] xe11 can be 1, 2 or 3,

[0328] xe1 can be 0, 1, 2, 3, 4, or 5,

[0329] R601 may be unsubstituted or substituted with at least one R 10a C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O) 2 (Q 601 ) or -P(=O)(Q 601 )(Q 602 ),

[0330] Q 601 To Q 603 can be independently compared with the Q 11 Same as described,

[0331] xe21 can be 1, 2, 3, 4, or 5, and

[0332] Ar 601 , L 601 and R 601 At least one of them may be independently unsubstituted or substituted with at least one R 10a The π-electron-poor nitrogen-containing C 1 -C 60 Ring group.

[0333] In an embodiment, in Formula 601, when xe11 is 2 or greater, two or more Ar 601 can be connected to each other via a single bond.

[0334] In the embodiment, in Formula 601, Ar 601 may be unsubstituted or substituted with at least one R 10a anthracene group.

[0335] In an embodiment, the electron transport region may include a compound represented by Formula 601-1:

[0336] Formula 601-1

[0337]

[0338] In formula 601-1,

[0339] X 614 Can be N or C (R 614 ), X 615 Can be N or C (R 615 ), X616 Can be N or C (R 616 ), X 614 To X 616 At least one of them can be N,

[0340] L 611 To L 613 can be independently related to L 601 Same as described,

[0341] xe611 to xe613 may each independently be the same as described herein with respect to xe1,

[0342] R 611 To R 613 can be independently compared with the 601 Same as described, and

[0343] R 614 To R 616 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group.

[0344] In an embodiment, in Formula 601 and Formula 601-1, xe1 and xe611 to xe613 may each independently be 0, 1, or 2.

[0345] In an embodiment, the electron transport region may include compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq 3 , BAlq, TAZ and NTAZ and / or any combination thereof:

[0346]

[0347]

[0348]

[0349] The thickness of the electron transport region can be about to about For example, the thickness of the electron transport region can be in the range of about to about When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, for example, the thickness of the buffer layer, the hole blocking layer, or the electron control layer can be independently about to about In the range of to about For example, the thickness of the buffer layer, the hole blocking layer, or the electron control layer can be independently about to about For example, the thickness of the electron transport layer can be about to about When the thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer and / or the electron transport region is within these ranges, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.

[0350] In addition to the above materials, the electron transport region (eg, the electron transport layer in the electron transport region) may further include a metal-containing material.

[0351] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex or any combination thereof. The metal ion of the alkali metal complex may be Li ion, Na ion, K ion, Rb ion or Cs ion, and the metal ion of the alkaline earth metal complex may be Be ion, Mg ion, Ca ion, Sr ion or Ba ion.

[0352] The ligands coordinated to the metal ion of the alkali metal complex or to the metal ion of the alkaline earth metal complex can each independently include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

[0353] For example, the metal-containing material may include a lithium (Li) complex. The Li complex may include, for example, compound ET-D1 (Liq) or compound ET-D2:

[0354]

[0355] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 150. The electron injection layer may directly contact the second electrode 150.

[0356] The electron injection layer may have: a structure composed of layers consisting of a single material; a structure composed of layers including different materials; or a structure including multiple layers, the multiple layers including different materials.

[0357] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0358] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.

[0359] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may be oxides, halides (e.g., fluorides, chlorides, bromides, or iodides), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.

[0360] The alkali metal compound may include: alkali metal oxides such as Li 2 O, Cs 2 O, or K 2 O; alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI; or any combination thereof. The alkaline earth metal compound may include alkaline earth metal oxides (such as BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying the condition 0 < x < 1) and / or Ba x Ca 1-x O (where x is a real number satisfying the condition 0 < x < 1)), etc. The rare earth metal compound may include YbF 3 , ScF 3 , Sc 2 O 3 , Y 2 O 3 , Ce 2 O 3 , GdF 3 , TbF 3 , YbI 3 , ScI 3 , TbI 3or any combination thereof. In an embodiment, the rare earth metal-containing compound may include a lanthanide metal telluride. Examples of lanthanide metal tellurides may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, LaTe, 2 Te 3 、Ce 2 Te 3 , Pr 2 Te 3 、Nd 2 Te 3 、Pm 2 Te 3 、Sm 2 Te 3 、Eu 2 Te 3 , Gd 2 Te 3 , Tb 2 Te 3 、Dy 2 Te 3 、Ho 2 Te 3 , Er 2 Te 3 、Tm 2 Te 3 , Yb 2 Te 3 He Lu 2 Te 3 .

[0361] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may include one of an alkali metal ion, an alkaline earth metal ion and a rare earth metal ion and a ligand bound to the metal ion (e.g., hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof).

[0362] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described above (e.g., composed of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described above). In an embodiment, the electron injection layer may also include an organic material (e.g., a compound represented by Formula 601).

[0363] In an embodiment, the electron injection layer may include an alkali metal compound (e.g., an alkali metal halide) (e.g., composed of an alkali metal compound (e.g., an alkali metal halide)); or the electron injection layer may include an alkali metal compound (e.g., an alkali metal halide) and an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof (e.g., composed of an alkali metal compound (e.g., an alkali metal halide) and an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof). For example, the electron injection layer may be a KI:Yb co-deposition layer, a RbI:Yb co-deposition layer, and / or a LiF:Yb co-deposition layer, etc.

[0364] When the electron injection layer also includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex or any combination thereof can be uniformly or non-uniformly dispersed in a matrix including the organic material.

[0365] The thickness of the electron injection layer can be about to about For example, the thickness of the electron injection layer can be about to about When the thickness of the electron injection layer is within the above range, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.

[0366] The second electrode 150

[0367] The second electrode 150 may be disposed on the intermediate layer 130. The second electrode 150 may be a cathode as an electron injection electrode. A material for forming the second electrode 150 may be a material having a low work function such as a metal, an alloy, a conductive compound, or any combination thereof.

[0368] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0369] The second electrode 150 may have a single-layer structure or a multi-layer structure.

[0370] Covering layer

[0371] The light emitting device 10 may include a first capping layer outside the first electrode 110 and / or a second capping layer outside the second electrode 150. For example, the light emitting device 10 may have: a structure in which the first capping layer, the first electrode 110, the intermediate layer 130, and the second electrode 150 are stacked in the stated order; a structure in which the first electrode 110, the intermediate layer 130, the second electrode 150 and the second capping layer are stacked in the stated order; or a structure in which the first capping layer, the first electrode 110, the intermediate layer 130, the second electrode 150 and the second capping layer are stacked in the stated order.

[0372] The light generated by the emission layer in the intermediate layer 130 of the light emitting device 10 may pass through the first electrode 110 (which may be a semi-transmissive electrode or a transmissive electrode) and through the first cover layer to be extracted to the outside. The light generated by the emission layer in the intermediate layer 130 of the light emitting device 10 may pass through the second electrode 150 (which may be a semi-transmissive electrode or a transmissive electrode) and through the second cover layer to be extracted to the outside.

[0373] According to the principle of constructive interference, the first capping layer and the second capping layer can both increase the external emission efficiency. Therefore, the light extraction efficiency of the light emitting device 10 is increased, so that the light emitting efficiency of the light emitting device 10 can be improved.

[0374] The first cap layer and the second cap layer may each include a material having a refractive index equal to or greater than about 1.6 (with respect to a wavelength of about 589 nm).

[0375] The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.

[0376] At least one selected from the first cover layer and the second cover layer may independently include a carbocyclic compound, a heterocyclic compound, an amine-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. In an embodiment, the carbocyclic compound, the heterocyclic compound, and the amine-containing compound may be optionally substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof.

[0377] In an embodiment, at least one selected from the first capping layer and the second capping layer may each independently include an amine-containing compound.

[0378] For example, at least one selected from the first capping layer and the second capping layer may each independently include the compound represented by Formula 201, the compound represented by Formula 202, or any combination thereof.

[0379] In an embodiment, at least one of the first cap layer and the second cap layer may each independently include at least one selected from compounds HT28 to HT33, at least one selected from compounds CP1 to CP6, β-NPB, and / or any combination thereof:

[0380]

[0381] membrane

[0382] The amine-containing compound represented by Chemical Formula 1 may be included in one or more suitable films. Therefore, another embodiment provides a film including the amine-containing compound represented by Chemical Formula 1. The film may be, for example, an optical member (or light control device) (e.g., a color filter, a color conversion member, a cover layer, a light extraction efficiency enhancement layer, a selective light absorption layer, a polarization layer, or a quantum dot layer, etc.), a light blocking member (e.g., a light reflecting layer and / or a light absorption layer, etc.), or a protective member (e.g., an insulating layer and / or a dielectric layer, etc.).

[0383] Electronic devices

[0384] The light emitting device may be included in one or more suitable electronic devices. In an embodiment, the electronic device including the light emitting device may be a light emitting device and / or an authentication device, etc.

[0385] In addition to the light emitting device, the electronic device (e.g., light emitting device) may further include a color filter, a color conversion layer, or a color filter and a color conversion layer. The color filter and / or the color conversion layer may be located in at least one direction along which the light emitted from the light emitting device travels. In an embodiment, the light emitted from the light emitting device may be blue light or white light. The light emitting device may be the same as described herein. In an embodiment, the color conversion layer may include quantum dots. The quantum dots may be, for example, quantum dots as described herein.

[0386] The electronic device may include a first substrate, the first substrate may include sub-pixels, the color filter may include color filter regions respectively corresponding to the sub-pixels, and the color conversion layer may include color conversion regions respectively corresponding to the sub-pixels.

[0387] A pixel defining film (hereinafter, referred to as a 'pixel defining layer') may be located between the sub-pixels to define each sub-pixel.

[0388] The color filter may further include color filter regions and light shielding patterns located between the color filter regions, and the color conversion layer may further include color conversion regions and light shielding patterns located between the color conversion regions.

[0389] The color filter region (or color conversion region) may include: a first region emitting a first color light; a second region emitting a second color light; and a third region emitting a third color light. The first color light, the second color light, and / or the third color light may have different maximum emission wavelengths from each other. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In an embodiment, the color filter region (or color conversion region) may include quantum dots. For example, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include (e.g., may exclude) quantum dots. The quantum dots may be the same as described herein. The first region, the second region, and / or the third region may each include a scatterer.

[0390] In an embodiment, the light emitting device may emit a first light, the first region may absorb the first light to emit a first first color light, the second region may absorb the first light to emit a second first color light, and the third region may absorb the first light to emit a third first color light. The first first color light, the second first color light, and the third first color light may have different maximum emission wavelengths from each other. For example, the first light may be blue light, the first first color light may be red light, the second first color light may be green light, and the third first color light may be blue light.

[0391] In addition to the light emitting device as described herein, the electronic device may further include a thin film transistor. The thin film transistor may include a source electrode, a drain electrode and an active layer, wherein one of the source electrode and the drain electrode may be electrically connected to one of the first electrode and the second electrode of the light emitting device.

[0392] The thin film transistor may further include a gate electrode and / or a gate insulating film, etc.

[0393] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, and / or an oxide semiconductor, etc.

[0394] The electronic device may further include a sealing portion for sealing the light-emitting device. The sealing portion may be located between the color filter and the light-emitting device and / or between the color conversion layer and the light-emitting device. The sealing portion may allow light from the light-emitting device to be extracted to the outside, and may concurrently (e.g., simultaneously) prevent or reduce the penetration of ambient air and moisture into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer including an organic layer and / or an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.

[0395] Depending on the purpose of the electronic device, in addition to the color filter and / or the color conversion layer, various functional layers may also be included on the sealing portion. Examples of functional layers may include a touch screen layer and / or a polarizing layer, etc. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The authentication device may be, for example, a biometric authentication device that authenticates an individual by utilizing biometric information of a living body (e.g., a fingertip, a pupil, etc.).

[0396] In addition to the light emitting device as described above, the authentication device may also include a biometric information collector.

[0397] The electronic device can be applied to one or more suitable displays, light sources, lighting, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notepads, electronic dictionaries, electronic game consoles, medical instruments (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, one or more suitable measuring instruments, meters (e.g., meters for vehicles, aircraft, and ships), and / or projectors, etc.

[0398] Electronic Devices

[0399] The light emitting device may be included in one or more suitable electronic devices.

[0400] In an embodiment, the electronic device including the light emitting device can be a flat panel display, a curved display, a computer monitor, a medical monitor, a television (TV), a billboard, indoor lighting, outdoor lighting, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a phone (such as a portable phone), a tablet personal computer, a tablet phone, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays spliced ​​together, a theater screen, a stadium screen, a light therapy device, or a sign.

[0401] Since the light emitting device has excellent or appropriate light emitting efficiency, long life, and the like, an electronic device including the light emitting device may have characteristics of high brightness, high resolution, and low power consumption.

[0402] Figure 4 and Figure 5 Description

[0403] Figure 4 is a schematic cross-sectional view of an electronic device according to an embodiment.

[0404] Figure 4 The electronic device (eg, a light emitting device) may include a substrate 100, a thin film transistor (TFT), a light emitting device, and an encapsulation part 300 sealing the light emitting device.

[0405] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. The buffer layer 210 may be located on the substrate 100. The buffer layer 210 may prevent or reduce impurities from penetrating through the substrate 100. The buffer layer 210 may provide a flat surface on the substrate 100.

[0406] The TFT may be located on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.

[0407] The active layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor. The active layer 220 may include a source region, a drain region, and a channel region.

[0408] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be located on the active layer 220 , and the gate electrode 240 may be located on the gate insulating film 230 .

[0409] An interlayer insulating film 250 may be located on the gate electrode 240. The interlayer insulating film 250 may be located between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.

[0410] Source electrode 260 and drain electrode 270 may be located on interlayer insulating film 250. Interlayer insulating film 250 and gate insulating film 230 may be formed to expose source and drain regions of active layer 220, and source electrode 260 and drain electrode 270 may contact the exposed portions of the source and drain regions of active layer 220, respectively.

[0411] The TFT is electrically connected to the light emitting device to drive the light emitting device, and is covered and protected by the passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The light emitting device is disposed on the passivation layer 280. The light emitting device may include a first electrode 110, an intermediate layer 130, and a second electrode 150.

[0412] The first electrode 110 may be located on the passivation layer 280. The passivation layer 280 may not completely cover the drain electrode 270. The passivation layer 280 may expose a portion of the drain electrode 270. The first electrode 110 may be electrically connected to the exposed portion of the drain electrode 270.

[0413] The pixel defining layer 290 including an insulating material may be located on the first electrode 110. The pixel defining layer 290 may expose a portion of the first electrode 110. The intermediate layer 130 may be formed on the exposed portion. The pixel defining layer 290 may be a polyimide or polyacrylic organic film. Figure 4 , but at least some of the intermediate layers 130 may extend beyond the upper portion of the pixel defining layer 290 to be provided in the form of a common layer.

[0414] The second electrode 150 may be located on the intermediate layer 130, and the capping layer 170 may be further located on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.

[0415] The encapsulation part 300 may be located on the capping layer 170. The encapsulation part 300 may be located on the light emitting device to protect the light emitting device from moisture and / or oxygen. The encapsulation part 300 may include: an inorganic film including silicon nitride (SiN x ), silicon oxide (SiO x ), indium tin oxide, indium zinc oxide or any combination thereof; organic films including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resins (e.g., polymethyl methacrylate and / or polyacrylic acid, etc.), epoxy resins (e.g., aliphatic glycidyl ether (AGE), etc.) or any combination thereof; or any combination of inorganic films and organic films.

[0416] Figure 5 is a schematic cross-sectional view of an electronic device according to another embodiment.

[0417] Figure 5 An electronic device (eg, a light emitting device) and Figure 4 The electronic device of the present invention may be different in that at least the light shielding pattern 500 and the functional area 400 are also included on the packaging part 300. The functional area 400 may be a color filter area, a color conversion area, or a combination of a color filter area and a color conversion area. Figure 5 The light emitting device in the electronic device may be a series light emitting device.

[0418] Figure 6 Description

[0419] Figure 6 is a schematic perspective view of an electronic device 1 including a light emitting device according to an embodiment.

[0420] The electronic device 1, which may be a device for displaying video or still images, may be not only a portable electronic device (such as a mobile phone, a smart phone, a tablet personal computer (PC), a mobile communication terminal, an electronic digital assistant, an e-book, a portable multimedia player (PMP), a navigation device, or an ultra mobile PC (UMPC)) (or a part thereof), but may also be one or more suitable products (such as a television, a laptop computer, a monitor, a billboard, or an Internet of Things (IOT) device).

[0421] The electronic device 1 may be a smart watch, a watch phone, or a wearable device such as a glasses type or kind of display or a head mounted display (HMD) or a part thereof. However, the embodiment is not limited thereto.

[0422] For example, the electronic device 1 may be a dashboard of a vehicle, a center information display (CID) arranged on a center dashboard or dashboard of a vehicle, an interior mirror display replacing a side mirror of a vehicle, a display for entertainment arranged in a rear seat of a vehicle or arranged on the back of a front seat, a head-up display (HUD) mounted on the front of the vehicle or projected onto a front windshield, or a computer generated hologram augmented reality head-up display (CGH AR HUD). For ease of explanation, Figure 6 An embodiment is shown in which the electronic device 1 is a smartphone.

[0423] The electronic device 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device may realize an image through a two-dimensional arrangement of pixels in the display area DA.

[0424] A non-display area NDA, which is an area where an image is not displayed, may surround the display area DA. A driver for supplying an electrical signal or power to a display element located in the display area DA may be arranged in the non-display area NDA. A pad, which is an area to which an electronic device or a printed circuit board may be electrically connected, may be arranged in the non-display area NDA.

[0425] The electronic device 1 may have different lengths in the x-axis direction and the y-axis direction. Figure 6As shown in , the length in the x-axis direction may be less than the length in the y-axis direction. In another embodiment, the length in the x-axis direction and the length in the y-axis direction may be the same. In yet another embodiment, the length in the x-axis direction may be greater than the length in the y-axis direction. In addition, the z-axis direction may be a direction perpendicular to the surface defined by the x-axis direction and the y-axis direction.

[0426] Figure 7 and FIG. 8A to FIG. 8C Description

[0427] Figure 7 is a schematic perspective view of the exterior of a vehicle 1000 as an electronic device including a light emitting device according to an embodiment.

[0428] FIG. 8A to FIG. 8C Each is a schematic diagram of the interior of a vehicle 1000 according to an embodiment.

[0429] Reference Figure 7 , Fig. 8A , Figure 8B and Figure 8C The vehicle 1000 may refer to one or more suitable devices that move a subject to be transported (such as a person, an object, or an animal) from a starting point to a destination. Examples of the vehicle 1000 may include a vehicle that travels on roads or tracks, a ship that moves on the ocean or a river, and an airplane that flies in the sky using the action of air.

[0430] The vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a given direction according to the rotation of at least one wheel. Examples of the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, an engine, a bicycle, and a train running on a track.

[0431] The vehicle 1000 may include a body having an interior and an exterior, and a chassis, which is a part other than the body and includes mechanical devices required for driving the vehicle installed therein. The exterior of the body may include a front panel, a hood, a roof panel, a rear panel, a trunk, at least one door, and pillars disposed at the boundaries between the doors. The chassis of the vehicle 1000 may include a power generation device, a power transmission device, a drive device, a steering device, a brake device, a suspension, a transmission, a fuel device, and a front wheel, a rear wheel, a left wheel, and a right wheel.

[0432] The vehicle 1000 may include side window glasses 1100 , a front window glass 1200 , side view mirrors 1300 , a cluster 1400 , a center instrument panel 1500 , a passenger seat instrument panel 1600 , and a display device 2 .

[0433] The side window glass 1100 and the front window glass 1200 may be separated by pillars disposed between the side window glass 1100 and the front window glass 1200 .

[0434] The side window glass 1100 may be installed on the side of the vehicle 1000. In an embodiment, the side window glass 1100 may be installed in a door of the vehicle 1000. The side window glass 1100 may be provided as a plurality of side window glasses that may face each other. In an embodiment, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In an embodiment, the first side window glass 1110 may be arranged adjacent to the cluster 1400, and the second side window glass 1120 may be arranged adjacent to the passenger seat instrument panel 1600.

[0435] In an embodiment, the side window glass 1100 may be spaced apart from each other in the x-axis direction or in a direction opposite to the x-axis direction. For example, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the x-axis direction or in a direction opposite to the x-axis direction. The imaginary straight line L connecting the side window glass 1100 may extend in the x-axis direction or in a direction opposite to the x-axis direction. For example, the imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 may extend in the x-axis direction or in a direction opposite to the x-axis direction.

[0436] The front window glass 1200 may be installed on the front of the vehicle 1000. The front window glass 1200 may be located between the side window glasses 1100 facing each other.

[0437] The side view mirror 1300 may provide a rear view of the vehicle 1000. The side view mirror 1300 may be mounted on the exterior of the vehicle body. In an embodiment, a plurality of side view mirrors 1300 may be provided. One of the side view mirrors 1300 may be located outside the first side window glass 1110. Another of the side view mirrors 1300 may be located outside the second side window glass 1120.

[0438] Cluster 1400 may be located in front of the steering wheel. A tachometer, a speedometer, a coolant temperature gauge, a fuel gauge, a turn signal indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, a driving record system, an automatic shift selector indicator, a door open warning light, an engine oil warning light, and / or a fuel storage warning light may be located on cluster 1400.

[0439] The central instrument panel 1500 may include a control panel having buttons for adjusting an audio device, an air conditioning device, and a seat heater. The central instrument panel 1500 may be located on one side of the cluster 1400 .

[0440] The passenger seat instrument panel 1600 may be separated from the cluster 1400 with the center instrument panel 1500 between the passenger seat instrument panel 1600 and the cluster 1400. In an embodiment, the cluster 1400 may be arranged to correspond to the driver's seat, and the passenger seat instrument panel 1600 may be arranged to correspond to the passenger seat. In an embodiment, the cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat instrument panel 1600 may be adjacent to the second side window glass 1120.

[0441] In an embodiment, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be located inside the vehicle 1000. In an embodiment, the display device 2 may be located between side window glasses 1100 facing each other. The display device 2 may be located in at least one of the cluster 1400, the center instrument panel 1500, and the passenger seat instrument panel 1600.

[0442] The display device 2 may include an organic light emitting display, an inorganic light emitting display, and / or a quantum dot display, etc. Hereinafter, an organic light emitting display including a light emitting device according to an embodiment is used as an example of the display device 2. However, one or more suitable display devices as described herein may be used as an embodiment.

[0443] Reference Fig. 8A , the display device 2 may be arranged in the central instrument panel 1500. In an embodiment, the display device 2 may display navigation information. In an embodiment, the display device 2 may display information about audio settings, video settings, or vehicle settings.

[0444] Reference Figure 8B , the display device 2 may be arranged in the cluster 1400. The cluster 1400 may display driving information and the like through the display device 2. Therefore, the cluster 1400 may digitally implement driving information. The digital cluster 1400 may digitally display vehicle information and driving information as images. For example, the needle and gauge of a tachometer and one or more warning lights may be displayed through digital signals.

[0445] Reference Figure 8C , the display device 2 may be arranged in the passenger seat instrument panel 1600. The display device 2 may be embedded in the passenger seat instrument panel 1600 or may be located on the passenger seat instrument panel 1600. In an embodiment, the display device 2 arranged in the passenger seat instrument panel 1600 may display an image about the information displayed on the cluster 1400 and / or the information displayed on the central instrument panel 1500. In another embodiment, the display device 2 arranged in the passenger seat instrument panel 1600 may display information different from the information displayed on the cluster 1400 and / or information different from the information displayed on the central instrument panel 1500.

[0446] Manufacturing method

[0447] The corresponding layer included in the hole transport region, the emission layer and the corresponding layer included in the electron transport region can be formed in a specific region by utilizing one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing and laser induced thermal imaging.

[0448] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition temperature may be about 100° C. to about 500° C., about 10 -8 About 10 -3 Torr vacuum and approx. to about The vacuum deposition was performed at a deposition rate of .

[0449] Definition of terms

[0450] As used herein, the term "C 3 -C 60 A "carbocyclic group" may be a cyclic group consisting only of carbon atoms as ring atoms and having 3 to 60 carbon atoms. As used herein, the term "C 1 -C 60 The "heterocyclic group" may be a cyclic group having 1 to 60 carbon atoms and further including at least one heteroatom as a ring-constituting atom other than carbon atoms. 3 -C 60 Carbocyclic and C 1 -C 60 The heterocyclic group may be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed with each other. 1 -C 60 The heterocyclic group can have 3 to 61 ring-forming atoms.

[0451] As used herein, the term "cyclic group" may be a C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.

[0452] As used herein, the term "π-electron-rich C 3 -C 60 The "cyclic group" may be a cyclic group having 3 to 60 carbon atoms and may not include (eg, may exclude) *-N=*' as a ring-forming portion. As used herein, the term "π-electron-poor nitrogen-containing C 1 -C 60The "heterocyclic group" may be a heterocyclic group having 1 to 60 carbon atoms and may include *-N=*' as a ring-forming part.

[0453] In an embodiment,

[0454] C 3 -C 60 The carbocyclic group may be: a T1 group; or a group in which two or more T1 groups are condensed with each other (for example, a cyclopentadiene group, an adamantane group, a norbornane group, a phenyl group, a pentalene group, a naphthalene group, an azulene group, an indacene group, an acenaphthene group, a phenanthrenyl group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, a benzophenone group, a fluorene group, a spirobifluorene group, a benzofluorene group, an indenophenanthrene group or an indenoanthracene group),

[0455] C 1 -C 60 The heterocyclic group may be: a T2 group; a group in which at least two T2 groups are condensed with each other; or a group in which at least one T2 group and at least one T1 group are condensed with each other (for example, a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzothiorrole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzothiorrole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolecarbazole group, a benzofuranocarbazole group, a benzothiophenocarbazole group, a benzothiorrolecarbazole group, a benzoindolecarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofuranodibenzofuran group, a benzofuranodibenzothiophene group, a benzothiophene and a benzothiophene group). dibenzothiophene group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group and / or an azadibenzofuran group, etc.),

[0456] Pi-electron-rich C 3 -C 60 The cyclic group may be: a T1 group; a group in which at least two T1 groups are condensed with each other; a T3 group; a group in which at least two T3 groups are condensed with each other; or a group in which at least one T3 group and at least one T1 group are condensed with each other (e.g., C 3 -C 60 a carbocyclic group, a 1H-pyrrole group, a thiol group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzothiol group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzothiol group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolecarbazole group, a benzofuranocarbazole group, a benzothiophenocarbazole group, a benzothiololcarbazole group, a benzoindolecarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthothiol group, a benzofuranodibenzofuran group, a benzofuranodibenzothiophene group and / or a benzothiophenodibenzothiophene group, and the like), and

[0457] π-electron-poor nitrogen-containing C 1 -C 60 The heterocyclic group may be: a T4 group; a group in which at least two T4 groups are condensed with each other; a group in which at least one T4 group and at least one T1 group are condensed with each other; a group in which at least one T4 group and at least one T3 group are condensed with each other; or a group in which at least one T4 group, at least one T1 group and at least one T3 group are condensed with each other (for example, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzisoxazole group , benzothiazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazoline group, benzoquinazoline group, phenanthroline group, cinnoline group, phthalazine group, naphthyridine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzothiophene group and / or azadibenzofuran group, etc.),

[0458] The T1 group can be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or bicyclo[2.2.1]heptane) group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group or a phenyl group.

[0459] The T2 group can be a furan group, a thiophene group, a 1H-pyrrole group, a thiol group, a borocyclopentadiene group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azathiol group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidinyl group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group or a dihydropyridazine group.

[0460] The T3 group may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group or a borole group.

[0461] The T4 group can be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azathiol group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group or a tetrazine group.

[0462] As used herein, the terms "cyclic group", "C 3 -C 60 Carbocyclic group, "C 1 -C 60 Heterocyclic group", "π-electron-rich C 3 -C 60 "Ring group" or "π-electron-poor nitrogen-containing C 1 -C 60 The term "heterocyclic group" may refer to a group condensed with any cyclic group, a monovalent group or a polyvalent group (e.g., a divalent group, a trivalent group and / or a tetravalent group, etc.) according to the structure of the formula using the corresponding term. For example, a "phenyl group" may be a benzo group, a phenyl group and / or a phenylene group, etc., which can be easily understood by a person of ordinary skill in the art based on the structure of the formula including the "phenyl group".

[0463] Unit Price C3 -C 60 Carbocyclic groups and monovalent C 1 -C 60 Examples of heterocyclic groups may include C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups.

[0464] Bivalent C 3 -C 60 Carbocyclic groups and divalent C 1 -C 60 Examples of heterocyclic groups include C 3 -C 10 Cycloalkylene, C 1 -C 10 Heterocycloalkylene, C 3 -C 10 Cycloalkenylene, C 1 -C 10 Heterocycloalkenylene, C 6 -C 60 Arylene, C 1 -C 60 heteroarylene groups, divalent non-aromatic condensed polycyclic groups and divalent non-aromatic condensed heteropolycyclic groups.

[0465] As used herein, the term "C 1 -C 60 The "alkyl" may be a straight or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms. 1 -C 60 Examples of alkyl groups may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, or tert-decyl.

[0466] As used herein, the term "C 1 -C 60 The "alkylene group" may be a 1 -C60 Alkyl is a divalent group of the same structure.

[0467] As used herein, the term "C 2 -C 60 The "alkenyl" may be in C 2 -C 60 A monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the end of the alkyl group. 2 -C 60 Examples of the alkenyl group may include ethenyl, propenyl, and butenyl.

[0468] As used herein, the term "C 2 -C 60 The "alkenylene" may be a 2 -C 60 Alkenyl is a divalent group of the same structure.

[0469] As used herein, the term "C 2 -C 60 The "alkynyl" may be in C 2 -C 60 A monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the end of the alkyl group. 2 -C 60 Examples of the alkynyl group may include ethynyl and propynyl.

[0470] As used herein, the term "C 2 -C 60 The "alkynylene group" may be a 2 -C 60 Alkynyl is a divalent group of the same structure.

[0471] As used herein, the term "C 1 -C 60 The "alkoxy" may be -O(A 101 )(Among them, A 101 Can be C 1 -C 60 C 1 -C 60 Examples of the alkoxy group may include a methoxy group, an ethoxy group, and an isopropoxy group.

[0472] As used herein, the term "C 3 -C 10 The "cycloalkyl" may be a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms. 3 -C 10Examples of cycloalkyl groups may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, and bicyclo[2.2.2]octyl.

[0473] As used herein, the term "C 3 -C 10 The "cycloalkylene" may be a 3 -C 10 Cycloalkyl is a divalent group of the same structure.

[0474] As used herein, the term "C 1 -C 10 The "heterocycloalkyl group" may be a monovalent ring group having 1 to 10 carbon atoms which further includes at least one heteroatom other than carbon atoms as a ring-constituting atom. 1 -C 10 Examples of the heterocycloalkyl group may include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl, and tetrahydrothienyl.

[0475] As used herein, the term "C 1 -C 10 The "heterocycloalkylene" may be a 1 -C 10 Heterocycloalkyl is a divalent group of the same structure.

[0476] As used herein, the term "C 3 -C 10 The "cycloalkenyl group" may be a non-aromatic monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring. 3 -C 10 Examples of the cycloalkenyl group may include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group.

[0477] As used herein, the term "C 3 -C 10 The cycloalkenylene group may be a 3 -C 10 Cycloalkenyl is a divalent group of the same structure.

[0478] As used herein, the term "C 1 -C 10 The "heterocycloalkenyl group" may be a monovalent cyclic group having 1 to 10 carbon atoms, which further includes at least one heteroatom other than carbon atoms as a ring-forming atom in its ring structure and has at least one double bond. 1 -C 10Examples of the heterocycloalkenyl group may include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl.

[0479] As used herein, the term "C 1 -C 10 The "heterocycloalkenylene" may be a 1 -C 10 Heterocycloalkenyl is a divalent group of the same structure.

[0480] As used herein, the term "C 6 -C 60 The term "aryl" may be a monovalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Examples of the aryl group may include phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, The following are examples of the compounds of the present invention: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31,

[0481] As used herein, the term "C 6 -C 60 The "arylene group" may be a divalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms.

[0482] When C 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the corresponding rings may be condensed with each other.

[0483] As used herein, the term "C 1 -C 60 The "heteroaryl group" may be a monovalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms, the heterocyclic aromatic system further comprising at least one heteroatom as a ring-forming atom other than carbon atoms. 1 -C 60 Examples of heteroaryl groups may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, and naphthyridinyl.

[0484] As used herein, the term "C 1 -C 60The "heteroarylene group" may be a divalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms, the heterocyclic aromatic system further including at least one heteroatom as a ring-constituting atom in addition to the carbon atom.

[0485] When C 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene group includes two or more rings, the corresponding rings may be condensed with each other.

[0486] The term "monovalent non-aromatic condensed polycyclic group" as used herein may be a monovalent group having two or more rings condensed with each other, having only carbon atoms (e.g., having 8 to 60 carbon atoms) as ring-forming atoms, and being non-aromatic in its entire molecular structure. Examples of monovalent non-aromatic condensed polycyclic groups may include indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl, and indenoanthryl.

[0487] The term "divalent non-aromatic condensed polycyclic group" as utilized herein may be a divalent group having the same structure as the above-mentioned monovalent non-aromatic condensed polycyclic group.

[0488] The term “monovalent non-aromatic condensed heteropolycyclic group” as utilized herein may be a monovalent group having two or more rings condensed to each other, further including at least one heteroatom as a ring-constituting atom other than carbon atoms (e.g., having 1 to 60 carbon atoms), and having non-aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group may include a pyrrolyl group, a thienyl group, a furyl group, an indolyl group, a benzindolyl group, a naphthoindolyl group, an isoindolyl group, a benzisoindolyl group, a naphthoisoindolyl group, a benzothioyl group, a benzofuranyl group, a carbazolyl group, a dibenzothioyl group, a dibenzothioyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzothioyl group, an azadibenzothioyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group , benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazine, imidazopyrazinyl, imidazopyridazinyl, indenocarbazolyl, indolecarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzothiorrolocarbazolyl, benzoindolecarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophene, benzonaphthothiorryl, benzofuranodibenzofuranyl, benzofuranodibenzothiophene and benzothiophenodibenzothiophene.

[0489] The term "divalent non-aromatic condensed heteropolycyclic group" as utilized herein may be a divalent group having the same structure as the above-mentioned monovalent non-aromatic condensed heteropolycyclic group.

[0490] As used herein, the term "C 6 -C 60 The "aryloxy" may be -O(A 102 )(Among them, A 102 Can be C 6 -C 60 A group represented by an aryl group.

[0491] As used herein, the term "C 6 -C 60 The "arylthio" group can be -S(A 103 )(Among them, A 103 Can be C 6 -C 60 A group represented by an aryl group.

[0492] As used herein, the term "C 7 -C 60 The "aralkyl" may be -(A 104 )(A 105 )(Among them, A 104 Can be C 1 -C 54 Alkylene, A 105 Can be C 6 -C 59 A group represented by an aryl group.

[0493] As used herein, the term "C 2 -C 60 The heteroarylalkyl group may be -(A 106 )(A 107 )(Among them, A 106 Can be C 1 -C 59 Alkylene, A 107 Can be C 1 -C 59 A group represented by a heteroaryl group.

[0494] In the specification, the group "R 10a " can be:

[0495] Deuterium (-D), -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0496] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy;

[0497] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 heteroarylalkyl; or

[0498] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ).

[0499] In the manual, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; or unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C alkoxy, phenyl, biphenyl or any combination thereof 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60Arylalkyl or C 2 -C 60 Heteroaralkyl.

[0500] As used herein, the term "heteroatom" may be any atom other than a carbon atom or a hydrogen atom. Examples of heteroatoms may include O, S, N, P, Si, B, Ge, Se, and any combination thereof.

[0501] The term “third row transition metal” as utilized herein may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt) and / or gold (Au), among others.

[0502] The term "Ph" as utilized herein refers to a phenyl group, the term "Me" as utilized herein refers to a methyl group, the term "Et" as utilized herein refers to an ethyl group, and the terms "tert-Bu" or "Bu" as utilized herein refer to a phenyl group. t ” refers to tert-butyl, and the term “OMe” as utilized herein refers to methoxy.

[0503] As used herein, the term "biphenyl" may be a "phenyl group substituted with a phenyl group". For example, a "biphenyl group" may be a group having C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.

[0504] As used herein, the term "terphenyl" may be a "phenyl group substituted with a biphenyl group". For example, a "terphenyl group" may be a phenyl group substituted with a C 6 -C 60 Aryl C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.

[0505] Unless otherwise defined, the symbols * and *' as utilized herein refer to the sites of bonding to adjacent atoms in the corresponding formula or moiety.

[0506] In the specification, the terms "x-axis", "y-axis" and "z-axis" are not limited to the three axes in the Cartesian coordinate system, and may have a broader meaning than the above three axes in the Cartesian coordinate system. For example, the x-axis, y-axis and z-axis may describe axes that are orthogonal to each other, or may describe axes in different directions that are not orthogonal to each other.

[0507] Organic Light Emitting Diodes

[0508] Figure 1 is a cross-sectional view illustrating an organic light emitting diode according to an example embodiment of the present disclosure.

[0509] Reference Figure 1, the organic light emitting diode includes an anode 10, a cathode 70, a light emitting layer 40 disposed between the two electrodes, a hole conduction layer 20 disposed between the anode 10 and the light emitting layer 40, and an electron conduction layer 50 disposed between the light emitting layer 40 and the cathode 70. The hole conduction layer 20 may include a hole transport layer 25 for transporting holes and a hole injection layer 23 for facilitating the injection of holes. The electron conduction layer 50 may include an electron transport layer 55 for transporting electrons and an electron injection layer 53 for facilitating the injection of electrons. In some embodiments, a hole blocking layer may be disposed between the light emitting layer 40 and the electron transport layer 55. In addition, an electron blocking layer may be disposed between the light emitting layer 40 and the hole transport layer 25. However, it is not limited thereto, and the electron transport layer 55 may be used as a hole blocking layer or the hole transport layer 25 may be used as an electron blocking layer.

[0510] When a forward bias is applied to the organic light emitting diode, holes are injected from the anode 10 into the light emitting layer 40, and electrons are injected from the cathode 70 into the light emitting layer 40. The electrons and holes injected into the light emitting layer 40 recombine to form excitons, and light is emitted when the excitons transition to a ground state.

[0511] The light-emitting layer 40 may be made of a single light-emitting material or may include a host material and a dopant material. A single light-emitting material or a light-emitting dopant material may be a compound represented by any one of the above-mentioned chemical formulas 1 to 12 and compounds 1 to 92, specifically, a thermally activated delayed fluorescent material. In this case, the efficiency of the organic light-emitting diode can be greatly improved. The thermally activated delayed fluorescent material has a form in which an electron-donating group and an electron-withdrawing group are connected to benzene and the electron-withdrawing group is located in the ortho position of the electron-donating group. Therefore, the difference between the singlet energy and the triplet energy can be reduced to less than 0.3eV. The thermally activated delayed fluorescent material can more effectively promote the transition from the triplet excited state to the singlet excited state by heat (at room temperature or at the element operating temperature), thereby improving the quantum efficiency. In some embodiments, one or more suitable combinations of red, green and blue luminescent colors can be achieved by appropriately or appropriately introducing electron-donating groups and electron-withdrawing groups.

[0512] The host material may be selected from the group consisting of: mCP (N,N-dicarbazolyl-3,5-benzene); Alq 3 ; CBP (4,4'-(N,N'-dicarbazolyl)-biphenyl); 9,10-di(naphthalene-2-yl)anthracene; TPBI (1,3,5-tri(N-phenylbenzimidazol-2-yl)benzene); TBADN (9,10-di(2-naphthyl)-2-tert-butyl-anthracene); E3 (see the formula below); and BeBq 2 (See the formula below).

[0513]

[0514] In some embodiments, the hole injection layer 23 and / or the hole transport layer 25 is a layer having a HOMO energy level between the escape functional level of the anode 10 and the HOMO energy level of the light-emitting layer 40, and has a function of improving the injection or transport efficiency of holes from the anode 10 to the light-emitting layer 40. The electron injection layer 53 and / or the electron transport layer 55 is a layer having a LUMO energy level between the escape functional level of the cathode 70 and the LUMO energy level of the light-emitting layer 40, and has a function of improving the injection or transport efficiency of electrons from the cathode 70 to the light-emitting layer 40.

[0515] The anode 10 may be a conductive metal oxide, a metal, a metal alloy or a carbon material. The conductive metal oxide may be selected from indium tin oxide (ITO), fluorine tin oxide (FTO), antimony tin oxide (ATO), SnO 2 At least one of the group consisting of , ZnO and any combination thereof. The metal or metal alloy suitable for the anode 10 may be Au or CuI. The carbon material may be graphite, graphene or carbon nanotubes.

[0516] The hole injection layer 23 or the hole transport layer 25 may include materials commonly used as hole transport materials, and one layer may have different hole transport materials or different hole transport material layers. The hole transport material may be, for example: mCP (N,N-dicarbazolyl-3,5-benzene); PEDOT:PSS (poly(3,4-ethylenedioxythiophene):polystyrene sulfonate); NPD (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine); N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl (TPD); N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl; N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl; N,N,N',N'-tetraphenyl-4,4'-diaminobiphenyl; porphyrinized Compound derivatives (such as 1,10,15,20-tetraphenyl-21H,23H-porphyrin copper (II)); TAPC (1,1-bis[4-[N,N'-di(p-tolyl)amino]phenyl]cyclohexane); triarylamine derivatives (such as N,N,N-tri(p-tolyl)amine and 4,4',4'-tri[N-(3-methylphenyl)-N-phenylamino]triphenylamine); carbazole derivatives (such as N-phenylcarbazole and polyvinylcarbazole); phthalocyanine derivatives (such as metal-free phthalocyanine and copper phthalocyanine); starburst amine derivatives; enamine stilbene derivatives; derivatives of aromatic tertiary amines and styrylamine compounds; and / or polysilane. Such hole transport materials can also be used as electron blocking layers.

[0517] The hole blocking layer is used to prevent or reduce triplet excitons or holes from diffusing toward the cathode 70 and can be arbitrarily selected from suitable hole blocking materials. For example, oxadiazole derivatives, triazole derivatives and / or phenanthroline derivatives can be used.

[0518] The electron transport layer 55 may be formed of a material selected from the group consisting of: TSPO1 (diphenylphosphine oxide-4-(triphenylsilyl)phenyl); tris(8-hydroxyquinoline)aluminum (Alq 3 ), 2,5-diarylthiorrole derivatives (PyPySPyPy), perfluorinated compounds (PF-6P), COTs (octasubstituted cyclooctatetraene), TAZ (see the chemical formula below), Bphen (4,7-diphenyl-1,10-phenanthroline), BCP (see the formula below) and BAlq (see the formula below).

[0519]

[0520] The electron injection layer 53 may be, for example, LiF, NaCl, CsF, Li 2 O, BaO, BaF 2 or Liq (lithium quinoline).

[0521] Cathode 70 is a conductive film having a lower work function than anode 10 and is made of a metal such as aluminum, magnesium, calcium, sodium, potassium, indium, yttrium, lithium, silver, lead and / or cesium, or a combination of two or more of these metals.

[0522] The anode 10 and the cathode 70 may be formed by sputtering, vapor deposition or ion beam deposition. The hole injection layer 23, the hole transport layer 25, the light emitting layer 40, the hole blocking layer, the electron transport layer 55 and the electron injection layer 53 are formed independently of each other by evaporation or coating methods such as spraying, spin coating, dipping, printing, blade coating or electrophoresis.

[0523] The organic light emitting diode may be disposed on a substrate, which may be disposed below the anode 10 or above the cathode 70. In other words, the anode 10 may be formed on the substrate before the cathode 70, or the cathode 70 may be formed on the substrate before the anode 10.

[0524] The substrate may be a light-transmitting substrate as a flat plate member, in which case the substrate may be glass; ceramic; or a polymer material such as polycarbonate (PC), polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyimide (PI), polypropylene (PP). However, the present disclosure is not limited thereto, and the substrate may be a metal substrate capable of light reflection.

[0525] Hereinafter, exemplary embodiments of the present disclosure will be described to facilitate understanding of the present disclosure. However, it should be understood that the following examples are for the purpose of promoting understanding of the present disclosure and are not intended to limit the scope of the present disclosure.

[0526] Example

[0527] Solution 1

[0528]

[0529] In Scheme 1, when R 1 and R 2 When both are hydrogen, the product is compound 1. 1 is methyl and R 2 When R 1 is tert-butyl and R 2 When R 1 is hydrogen and R 2 When it is methyl, the product is compound 37.

[0530] Synthesis Example 1: Synthesis of Compound 1

[0531] Step 1 : Carbazole (10.0 g, 59.8 mmol), 1,2-dibromobenzene (21.16 g, 89.71 mmol), potassium carbonate (16.53 g, 119.61 mmol) and copper iodide (CuI) (5.69 g, 29.90 mmol) were dissolved in N,N-dimethylacetamide (250 mL), and then oxygen was removed from the solution by nitrogen bubbling. After removing oxygen, the mixture was refluxed and stirred for 24 hours. The reaction solution was extracted with dichloromethane, and then column chromatography was performed using a dichloromethane / hexane mixed solvent as an eluent to obtain 15.99 g of 9-(2-bromophenyl)carbazole. 9-(2-bromophenyl)carbazole: mass spectrum (EI) m / z 322 [(M+H) + ].

[0532] Step 2: 9-(2-bromophenyl)carbazole (10 g, 31.03 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (11.82 g, 46.55 mmol), potassium acetate (9.14 g, 93.11 mmol) and 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) (0.76 g, 0.93 mmol) were dissolved in 1,4-dioxane (180 mL), and then the oxygen in the solution was removed by nitrogen bubbling. After removing the oxygen, the mixture was refluxed and stirred for 24 hours. The reaction solution was extracted with dichloromethane, and then column chromatography was performed using a dichloromethane / hexane mixed solvent as an eluent to obtain 4.01 g of 9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbazole. 9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbazole: mass spectrum (EI) m / z 369 [(M+H) + ].

[0533] Step 3 : 9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbazole (3 g, 8.12 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.61 g, 9.75 mmol), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh 3 ) 4 , 0.28 g, 0.24 mmol) was added to tetrahydrofuran (60 mL) and potassium carbonate 2M solution (20 mL, K 2 CO 3 ) mixed solvent, and then the mixture was refluxed for 24 hours. The reaction solution was extracted with dichloromethane, and then purified by column chromatography using a dichloromethane / hexane mixed solvent as an eluent, and finally purified by sublimation to obtain 3.31 g of a pure white solid.

[0534] Compound 1 : Yield 86%, mass spectrum (EI) m / z 474 [(M+H) + ]. Element analysis theoretical value C 33 H 22 N 4 : C, 83.52%; H, 4.67%; N, 11.81%. Measured values: C, 83.52%; H, 4.74%; N, 11.69%. 1 H NMR (500 MHz, CDCl 3): δ8.57(d,1H), 8.03(t,6H), 7.85(t,1H), 7.78(t,1H), 7.73(d,1H), 7.48(t,2H), 7.34(t,6H), 7.24~7.19(m,4H).

[0535] Synthesis Example 2: Synthesis of Compound 2

[0536] Compound 2 was obtained in a yield of 83% by the same method as Synthesis Example 1, except that 3,6-dimethylcarbazole was used instead of carbazole in Step 1 of Synthesis Example 1.

[0537] Compound 2 :Mass spectrum (FAB) m / z 502[(M+H) + ]. Element analysis theoretical value C 35 H 26 N 4 : C (83.64%) H (5.21%) N (11.15%). Measured values: C, 83.69%; H, 5.26%; N, 11.09%. 1 H NMR (500 MHz, CDCl 3 ): 8.50(d,1H), 8.00(d,4H), 7.78(t,3H), 7.73(t,1H), 7.67(d,1H), 7.47(t,2H), 7.31(t,4H), 7.11(d,2H), 7.06(d,2H), 2.49(s,6H).

[0538] Synthesis Example 3: Synthesis of Compound 3

[0539] Compound 3 was obtained in a yield of 81% by the same method as Synthesis Example 1, except that 3,6-di-tert-butylcarbazole was used instead of carbazole in Step 1 of Synthesis Example 1.

[0540] Compound 3 :Mass spectrum (EI) m / z 586[(M+H) + ]. Element analysis theoretical value C 41 H 38 N 4 : C (83.92%) H (6.53%) N (9.55%). Measured values: C, 83.85%; H, 6.61%; N, 9.53%. 1 H NMR (500 MHz, CDCl 3): 8.56(d,1H), 8.09(d,4H), 8.02(d,2H), 7.81(t,1H), 7.74(t,1H), 7.68(d,1H), 7.49(t,2H), 7.34(t,6H), 7.11(d,2H), 1.42(s,18H).

[0541] Synthesis Example 4: Synthesis of Compound 37

[0542] Compound 37 was obtained in a yield of 78% by the same method as Synthesis Example 1, except that 2-chloro-4,6-di-p-tolyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in Step 3 of Synthesis Example 1.

[0543] Compound 37 :Mass spectrum (FAB) m / z 502[(M+H) + ]. Element analysis theoretical value C 35 H 26 N 4 : C (83.64%) H (5.21%) N (11.15%). Measured value: C (83.53%) H (5.27%) N (11.18%). 1 H NMR (500 MHz, CDCl 3 ): 8.55(d,1H), 7.95(d,4H), 7.78~7.72(m,3H), 7.48(t,2H), 7.11(d,4H), 7.05~6.95(m,6H), 2.72(s,6H).

[0544] Synthesis Example 5: Synthesis of Compound 22

[0545] Solution 2-1

[0546]

[0547] Step 1 : diphenylamine (10.0g, 59.09mmol), 1,2-dibromobenzene (27.88g, 118.19mmol), sodium tert-butoxide (6.814g, 70.908mmol), palladium acetate (0.663g, 2.95mmol) and tri-tert-butylphosphine (1.19g, 5.91mmol) are dissolved in toluene (300mL), then oxygen is removed from solution by nitrogen bubbling. After removing oxygen, the mixture is refluxed and stirred for 24 hours. The reaction solution is extracted with dichloromethane, then column chromatography is performed using dichloromethane / hexane mixed solvent as eluent to obtain 12.21g of intermediate 22-1.

[0548] Intermediate 22-1:Mass spectrum (EI) m / z 324[(M+H) + ].

[0549] Solution 2-2

[0550]

[0551] Step 2 :Intermediate 22-1 (10g, 30.84mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborane) (11.74g, 46.26mmol), potassium acetate (9.08g, 92.52mmol) and 1,1'-bis(diphenylphosphino)ferrocene-dichloropalladium(II) dichloromethane complex (0.76g, 0.93mmol) were dissolved in 1,4-dioxane (180mL), and then oxygen was removed from the solution by nitrogen bubbling. After removing oxygen, the mixture was refluxed and stirred for 24 hours. The reaction solution was extracted with dichloromethane, and then column chromatography was performed using a dichloromethane / hexane mixed solvent as an eluent to obtain 4.58g of intermediate 22-2.

[0552] Intermediate 22-2 :Mass spectrum (EI) m / z 371[(M+H) + ].

[0553] Scheme 2-3

[0554]

[0555] Step 3 :Intermediate 22-2 (3g, 8.08mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.59g, 9.75mmol) and tetrakis (triphenylphosphine) palladium (0) (0.28g, 0.24mmol) are added to the mixed solvent of tetrahydrofuran (60mL) and potassium carbonate 2M solution (20mL), then the mixture is refluxed for 24 hours.The reaction solution is extracted with dichloromethane, then dichloromethane / hexane mixed solvent is utilized as eluent by column chromatography purification, finally by sublimation purification obtains 3.08g of compound 22 as pure white solid.

[0556] Compound 22 : Yield 86%, mass spectrum (EI) m / z 476 [(M+H) + ]. Element analysis theoretical value C 33 H 24 N 4 : C, 83.17%; H, 5.08%; N, 11.76%. Measured values: C, 82.16%; H, 5.12%; N, 11.77%. 1H NMR (500 MHz, CDCl 3 ): δ8.83(d,1H), 8.51(d,4H), 8.05(d,1H), 7.64~7.61(m,2H), 7.57~7.53 (m,3H), 7.46(t,4H), 7.41(d,2H), 7.09~7.04(m,5H), 6.83~6.79(m,2H).

[0557] Synthesis Example 6: Synthesis of Compound 23

[0558] Solution 3

[0559]

[0560] Compound 23 was obtained in a yield of 78% using the same method as Synthesis Example 5, except that di-p-tolylamine was used instead of diphenylamine in Step 1 of Synthesis Example 5 to obtain 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N,N-di-p-tolylaniline in Step 2 and used it in Step 3.

[0561] Compound 23 :Mass spectrum (EI) m / z 504[(M+H) + ]. Element analysis theoretical value C 35 H 28 N 4 : C (83.30%) H (5.59%) N (11.10%). Measured values: C, 83.32%; H, 5.66%; N, 11.05%. 1 H NMR (500 MHz, CDCl 3 ): 8.52(d,4H), 7.95(d,1H), 7.56(t,2H), 7.53~7.45(m,5H), 7.38~7.32(m,2H), 6.92(d,4H), 6.85(d,4H).

[0562] Synthesis Example 7: Synthesis of Compound 36

[0563] Solution 4-1

[0564]

[0565] (2-(Carbazole-9-yl)phenyl)boric acid (10 g, 34.83 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (7.87 g, 34.83 mmol), tetrakis(triphenylphosphine)palladium(0) (4.02 g, 3.48 mmol) and potassium carbonate (14.44 g, 104.49 mmol) were added to tetrahydrofuran (60 mL) and distilled water (20 mL), and the mixture was refluxed and stirred for 24 hours. The reaction solution was extracted with dichloromethane, and then column chromatography was performed using a dichloromethane / hexane mixed solvent as an eluent to obtain 7.99 g of intermediate 36-1.

[0566] Intermediate 36-1 :Mass spectrum (EI) m / z 432[(M+H) + ].

[0567] Solution 4-2

[0568]

[0569] Intermediate 36-1 (3 g, 6.94 mmol) and cupric cyanide (2.18 g, 24.31 mmol) were dissolved in N-methyl-2-pyrrolidone (50 mL), and then oxygen was removed from the solution by nitrogen bubbling. After removing oxygen, the mixture was refluxed and stirred for 24 hours. The reaction solution was extracted with dichloromethane, and then column chromatography was performed using dichloromethane / hexane mixed solvent as eluent to obtain 2.49 g of compound 36.

[0570] Compound 36 :Mass spectrum (EI) m / z 423[(M+H) + ]. Element analysis theoretical value C 28 H 17 N 5 : C (79.42%) H (4.05%) N (16.54%). Measured values: C, 79.43%; H, 4.07%; N, 16.51%. 1 H NMR (500 MHz, CDCl 3 ): 8.41(d,1H), 8.02(d,2H), 7.85(t,1H), 7.75~7.70(m,2H), 7.36~7.29(m,5H), 7.22(t,2H), 7.15(d,2H), 7.10(t,2H).

[0571] Solution 5

[0572]

[0573] In Scheme 5, when R 1 and R 2When both are hydrogen, the product is compound 61. 1 is hydrogen and R 2 When it is methyl, the product is compound 63.

[0574] Synthesis Example 8: Synthesis of Compound 61

[0575] Step 1 : 2-chloro-4,6-diphenyl-1,3,5-triazine (5.0g, 18.67mmol), (2-fluorophenyl) boronic acid (3.92g, 28.01mmol), tetrakis (triphenylphosphine) palladium (0) (2.15g, 1.86mmol), potassium carbonate (7.74g, 56.03mmol) are dissolved in toluene (120mL), ethanol (60mL), DW (90mL), and then oxygen is removed from the solution by nitrogen bubbling. After removing oxygen, the mixture is stirred at room temperature for 1 hour, then refluxed and stirred at 130°C for 15 hours. Then, the reaction solution is vacuum dried by removing the solvent through a rotary evaporator. The dried mixture is extracted with dichloromethane, and then column chromatography is performed using a dichloromethane / hexane mixed solvent as an eluent to obtain 5.4g of 2-(2-fluorophenyl)-4,6-diphenyl-1,3,5-triazine.

[0576] 2-(2-Fluorophenyl)-4,6-diphenyl-1,3,5-triazine: mass spectrum (EI) m / z 327 [(M+H) + ]. 1 H NMR (500 MHz, CDCl 3 ): 8.76(d,4H), 8.48(t,1H), 7.62(t,3H), 7.56(t,4H), 7.35(t,1H), 7.27(t,1H).

[0577] Step 2 : 2-(2-fluorophenyl)-4,6-diphenyl-1,3,5-triazine (1.00 g, 3.05 mmol), indole (0.89 g, 7.63 mmol) and sodium tert-butoxide (0.73 g, 7.63 mmol) were mixed in a solvent of dimethylformamide (100 mL) and refluxed at 160° C. for 24 hours. The reaction solution was extracted with dichloromethane, then purified by column chromatography using a dichloromethane / hexane mixed solvent as an eluent, and finally purified by sublimation to obtain 0.63 g of compound 61 as a yellow solid.

[0578] Compound 61 : Yield 49.5%, mass spectrum (EI) m / z 424 [(M+H) + ]. Element analysis theoretical value C 29 H 20 N 4: C (82.05%) H (4.75%) N (13.20%). Measured values: C, 81.98%; H, 4.77%; N, 13.11%. 1 H NMR (500 MHz, CDCl 3 ): 8.42(d,1H), 8.16(d,4H), 7.73(t,1H), 7.66(t,2H), 7.61(d,1H), 7.50(t, 2H), 7.38(t,4H), 7.31(d,1H), 7.19~7.13(m,2H), 7.07(d,1H), 6.53(d,1H).

[0579] Synthesis Example 9: Synthesis of Compound 63

[0580] 1.17 g of Compound 63 was obtained in a manner similar to that in Step 2 of Synthesis Example 8, except that 2-(2-fluorophenyl)-4,6-diphenyl-1,3,5-triazine (1.50 g, 4.58 mmol), 3-methylindole (1.50 g, 11.45 mmol) and sodium tert-butoxide (1.10 g, 11.45 mmol) obtained in Step 1 of Synthesis Example 8 were added to a solvent of dimethylformamide (100 mL).

[0581] Compound 63 : Yield 58.07%, mass spectrum (EI) m / z 438 [(M+H) + ]. Element analysis theoretical value C 30 H 22 N 4 : C (82.17%) H (5.06%) N (12.78%), measured values: C, 82.22%; H, 4.97%; N, 12.69%. 1 H NMR (500 MHz, CDCl 3 ): 8.43(d,1H), 8.20(d,4H), 7.71(t,1H), 7.62(t,2H), 7.52(t,3H), 7.39 (t,4H), 7.19~7.17(m,1H), 7.10~6.94(m,2H), 6.94(s,1H), 2.26(s,3H).

[0582] Synthesis Example 10: Synthesis of Compound 52

[0583] Solution 6

[0584]

[0585] 2-(2-Fluorophenyl)-4,6-diphenyl-1,3,5-triazine (1.00 g, 3.05 mmol), 5H-benzofurano[3,2-c]carbazole (0.98 g, 3.82 mmol), sodium hydride (NaH, 0.10 g, 3.90 mmol) were mixed in a solvent of dimethylformamide (100 mL) and refluxed at 160° C. for 24 hours. The reaction solution was extracted with dichloromethane, then purified by column chromatography using a dichloromethane / hexane mixed solvent as an eluent, and finally purified by sublimation to obtain 1.35 g of compound 52 as a yellow solid.

[0586] Compound 52 : Yield 78.4%, mass spectrum (EI) m / z 565 [(M+H) + ]. 1 H NMR (300MHz, DMSO): 7.16~7.26(m,6H), 7.34~7.51(m,6H), 7.82(d,1H), 7.88~7.99(m,6H), 8.03~8.31(m,3H), 8.30(d,1H), 8.60(d,1H).

[0587] Synthesis Example 11: Synthesis of Compound 67

[0588] Solution 7

[0589]

[0590] (2-(Carbazole-9-yl)phenyl)boric acid (8.0 g, 27.9 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (3.0 g, 13.3 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.53 g, 1.33 mmol) were added to a mixed solvent of tetrahydrofuran (100 mL) and potassium carbonate 2M solution (40 mL) and refluxed for 24 hours. The reaction solution was extracted with dichloromethane, then purified by column chromatography using a dichloromethane / hexane mixed solvent as an eluent, and finally purified by sublimation to obtain a pure white solid in a yield of 71%.

[0591] Compound 67 :Mass spectrum (EI) m / z 639[(M+H) + ]. Element analysis theoretical value C 45 H 29 N 5 : C (84.48%) H (4.57%) N (10.95%). Measured value: C (84.48%) H (4.57%) N (10.86%). 1 H NMR (500 MHz, CDCl 3): δ6.79(d,2H,J=8Hz), 6.895(t,2H,J=15Hz), 6.965(d,4H,J=8Hz), 7.163~7.217(m,5H), 7.263(t, 4H, J=15Hz), 7.478 (t, 2H, J=15Hz), 7.563 (d, 2H, J=8Hz), 7.659~7.708 (m, 4H), 7.986 (d, 4H, J=8Hz).

[0592] Synthesis Example 12: Synthesis of Compound 83

[0593] Solution 8

[0594]

[0595] (2-(Carbazole-9-yl)phenyl)boric acid (15.4 g, 53.7 mmol), cyanuric chloride (3.0 g, 16.3 mmol) and tetrakis(triphenylphosphine)palladium(0) (2.82 g, 2.44 mmol) were added to a mixed solvent of tetrahydrofuran (100 mL) and potassium carbonate 2M solution (40 mL) and refluxed for 24 hours. The reaction solution was extracted with dichloromethane, then purified by column chromatography using a dichloromethane / hexane mixed solvent as an eluent, and finally purified by sublimation to obtain a pure white solid in a yield of 37%.

[0596] Compound 83 :Mass spectrum (EI) m / z 803[(M+H) + ]. Element analysis theoretical value C 57 H 36 N 6 : C (85.05%) H (4.51%) N (10.44%). Measured value: C (85.07%) H (4.49%) N (10.45%). 1 H NMR (500 MHz, CDCl 3 ): δ6.238(d,3H,J=8Hz), 6.558(d,6H,J=8Hz), 6.968(t,3H,J=15Hz), 7.216~7 .261(m,12H), 7.341(d,3H,J=8Hz), 7.485(t,3H,J=15Hz), 8.10(d,6H,J=7Hz).

[0597] Preparation Example 1: Preparation of delayed fluorescence organic light-emitting diodes

[0598] (ITO / PEDOT:PSS / TAPC / mCP / mCP:Compound 1 / TSPO1 / TPBi / LiF / Al)

[0599] The glass substrate on which the anode ITO was deposited was ultrasonically cleaned for 30 minutes using pure water and isopropyl alcohol. The cleaned ITO substrate was surface treated using short-wavelength ultraviolet rays, and then a hole injection layer was formed by spin coating PEDOT:PSS (poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate)) to a thickness of 60 nm. Thereafter, a 1×10 -6 TAPC (1,1-bis[4-[N,N'-di(p-tolyl)amino]phenyl]cyclohexane) was vapor-deposited at a rate of 0.1 nm / s at a pressure of 10 torr to form a 20 nm hole transport layer. -6 mCP (N,N-dicarbazolyl-3,5-benzene) was vapor-deposited at a rate of 0.1 nm / s at a pressure of 10 torr to form a 10 nm electron blocking layer. -6 Under a pressure of 1×10 -6 TSPO1 (diphenylphosphine oxide-4-(triphenylsilyl)phenyl) and TPBi (1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene) were sequentially vapor-deposited at a rate of 0.1 nm / s at a pressure of 10 torr to form a 5 nm hole blocking layer and a 30 nm electron transport layer, respectively. -6 LiF as an electron injection material was vapor-deposited at a rate of 0.01 nm / s under a pressure of 1 × 10 -6 Al was vapor-deposited at a rate of 0.5 nm / sec under a pressure of 100 torr to form a cathode of 100 nm, thereby forming an organic light emitting diode. After the organic light emitting device was formed, the organic light emitting device was sealed using a CaO moisture absorber and a glass cover.

[0600] The organic light emitting device using compound 1 as a fluorescent dopant material has a quantum efficiency of 9.3%, a current efficiency of 14.6 cd / A, a power efficiency of 7.6 lm / W at a voltage of 6 V, and x=0.15 and y=0.22 based on CIE 1931 color coordinates (indicating excellent or suitable blue light emission characteristics). These results exceed the limit of the maximum external quantum efficiency of 5% (light extraction efficiency of 20%) that can be obtained from general fluorescent devices, and it can directly prove that the triplet energy level is converted to the singlet energy level through intersystem crossing, which is the property of thermally activated delayed fluorescent materials.

[0601] Preparation Example 2: Preparation of delayed fluorescence organic light-emitting diodes

[0602] (ITO / PEDOT:PSS / TAPC / mCP / mCP:Compound 2 / TSPO1 / TPBi / LiF / Al)

[0603] An organic light emitting diode was manufactured in substantially the same manner as Preparation Example 1, except that Compound 2 synthesized by Synthesis Example 2 was used as a delayed fluorescence dopant material.

[0604] The organic light emitting diode according to Preparation Example 2 using Compound 2 as a fluorescent dopant material exhibited a quantum efficiency of 14.7%, a current efficiency of 30.9 cd / A, a power efficiency of 14.9 lm / W at a voltage of 6 V, and x=0.17 and y=0.34 based on CIE1931 color coordinates (indicating excellent or suitable blue light emission characteristics).

[0605] Preparation Example 3: Preparation of delayed fluorescence organic light-emitting diodes

[0606] (ITO / PEDOT:PSS / TAPC / mCP / mCP:Compound 3 / TSPO1 / TPBi / LiF / Al)

[0607] An organic light emitting diode was manufactured in substantially the same manner as Preparation Example 1, except that Compound 3 synthesized by Synthesis Example 3 was used as a delayed fluorescence dopant material.

[0608] The organic light emitting diode according to Preparation Example 3 using Compound 3 as the fluorescent dopant material exhibited a quantum efficiency of 12.3%, a current efficiency of 24.0 cd / A, a power efficiency of 12.6 lm / W at a voltage of 6 V, and x=0.16 and y=0.30 based on CIE1931 color coordinates (indicating excellent or suitable blue light emission characteristics).

[0609] Preparation Example 4: Preparation of delayed fluorescence organic light-emitting diodes

[0610] (ITO / PEDOT:PSS / TAPC / mCP / mCP:Compound 37 / TSPO1 / TPBi / LiF / Al)

[0611] An organic light emitting diode was manufactured in substantially the same manner as Preparation Example 1, except that Compound 37 synthesized by Synthesis Example 4 was used as a delayed fluorescence dopant material.

[0612] The organic light emitting diode according to Preparation Example 4 using Compound 37 as a fluorescent dopant material exhibited a quantum efficiency of 11.5%, a current efficiency of 29.1 cd / A, a power efficiency of 13.8 lm / W at a voltage of 6 V, and x=0.16 and y=0.30 based on CIE1931 color coordinates (indicating excellent or suitable blue light emission characteristics).

[0613] Preparation Example 5: Preparation of delayed fluorescence organic light-emitting diodes

[0614] (ITO / PEDOT:PSS / TAPC / mCP / mCP:Compound 22 / TSPO1 / TPBi / LiF / Al)

[0615] An organic light emitting diode was manufactured in substantially the same manner as Preparation Example 1, except that Compound 22 synthesized by Synthesis Example 5 was used as a delayed fluorescence dopant material.

[0616] The organic light-emitting diode according to Preparation Example 5 using Compound 22 as a fluorescent dopant material exhibited a quantum efficiency of 17.2%, a current efficiency of 45.0 cd / A, a power efficiency of 31.4 lm / W at a voltage of 9 V, and x=0.21 and y=0.45 based on CIE1931 color coordinates (indicating excellent or suitable blue-green light emission characteristics).

[0617] Preparation Example 6: Preparation of delayed fluorescence organic light-emitting diodes

[0618] (ITO / PEDOT:PSS / TAPC / mCP / mCP:Compound 52 / TSPO1 / TPBi / LiF / Al)

[0619] An organic light emitting diode was manufactured in substantially the same manner as Preparation Example 1, except that Compound 52 synthesized by Synthesis Example 10 was used as a delayed fluorescence dopant material.

[0620] The organic light-emitting diode according to Preparation Example 6 using Compound 52 as a fluorescent dopant material exhibited a quantum efficiency of 12.5%, a current efficiency of 19.8 cd / A, a power efficiency of 17.8 lm / W at a voltage of 9 V, and x=0.15 and y=0.20 based on CIE1931 color coordinates (indicating excellent or suitable blue light emission characteristics).

[0621] Preparation Example 7: Preparation of delayed fluorescence organic light-emitting diodes

[0622] (ITO / PEDOT:PSS / TAPC / mCP / mCP:Compound 23 / TSPO1 / TPBi / LiF / Al)

[0623] An organic light emitting diode was manufactured in substantially the same manner as Preparation Example 1, except that Compound 23 synthesized by Synthesis Example 6 was used as a delayed fluorescence dopant material.

[0624] The organic light-emitting diode according to Preparation Example 7 using Compound 23 as a fluorescent dopant material exhibited a quantum efficiency of 16.3%, a current efficiency of 54.6 cd / A, a power efficiency of 32.8 lm / W at a voltage of 9 V, and x=0.35 and y=0.58 based on CIE1931 color coordinates (indicating excellent or suitable green light emission characteristics).

[0625] Preparation Example 8: Preparation of delayed fluorescence organic light-emitting diodes

[0626] (ITO / PEDOT:PSS / TAPC / mCP / mCP:Compound 36 / TSPO1 / TPBi / LiF / Al)

[0627] An organic light emitting diode was manufactured in substantially the same manner as Preparation Example 1, except that Compound 36 synthesized by Synthesis Example 7 was used as a delayed fluorescence dopant material.

[0628] The organic light-emitting diode according to Preparation Example 8 using Compound 36 as a fluorescent dopant material exhibited a quantum efficiency of 11.7%, a current efficiency of 26.9 cd / A, a power efficiency of 10.4 lm / W at a voltage of 6 V, and x=0.55 and y=0.45 based on CIE1931 color coordinates (indicating excellent or suitable red light emission characteristics).

[0629] Preparation Example 9: Preparation of delayed fluorescence organic light-emitting diode

[0630] (ITO / PEDOT:PSS / TAPC / mCP / mCP:Compound 67 / TSPO1 / TPBi / LiF / Al)

[0631] An organic light emitting diode was manufactured in substantially the same manner as Preparation Example 1, except that Compound 67 synthesized by Synthesis Example 11 was used as a delayed fluorescence dopant material.

[0632] The organic light-emitting diode according to Preparation Example 9 using Compound 67 as a fluorescent dopant material exhibited a quantum efficiency of 12.2%, a current efficiency of 18.5 cd / A, a power efficiency of 6.47 lm / W at a voltage of 8 V, and x=0.17 and y=0.21 based on CIE1931 color coordinates (indicating excellent or suitable blue light emission characteristics).

[0633] Preparation Example 10: Preparation of delayed fluorescence organic light-emitting diode

[0634] (ITO / PEDOT:PSS / TAPC / mCP / mCP:Compound 83 / TSPO1 / TPBi / LiF / Al)

[0635] An organic light emitting diode was manufactured in substantially the same manner as Preparation Example 1, except that Compound 83 synthesized by Synthesis Example 12 was used as a delayed fluorescence dopant material.

[0636] The organic light-emitting diode according to Preparation Example 10 using Compound 83 as a fluorescent dopant material exhibited a quantum efficiency of 14.9%, a current efficiency of 23.0 cd / A, a power efficiency of 9.57 lm / W at a voltage of 8 V, and x=0.15 and y=0.22 based on CIE1931 color coordinates (indicating excellent or suitable blue light emission characteristics).

[0637] Comparative Example 1: Preparation of delayed fluorescence organic light-emitting diodes

[0638] (ITO / PEDOT:PSS / TAPC / mCP / mCP:CC2TA / TSPO1 / TPBi / LiF / Al)

[0639] An organic light emitting diode was manufactured in substantially the same manner as in Preparation Example 1, except that 2,4-bis(3-(9H-carbazole-9-yl)-9H-carbazole-9-yl)-6-phenyl-1,3,5-triazine (CC2TA) reported in the paper (APPLIED PHYSICS LETTERS 101, 093306 (2012)) was used as a delayed fluorescence dopant material.

[0640] The organic light emitting diode according to Comparative Example 1 using CC2TA as a fluorescent dopant material exhibited a quantum efficiency of 11.5%, a current efficiency of 29.1 cd / A, a power efficiency of 13.8 lm / W at a voltage of 6 V, and x=0.20 and y=0.44 based on CIE1931 color coordinates.

[0641] Blue (Preparation Examples 1 to 4, 6, 9, and 10), green (Preparation Examples 5 and 7), and red (Preparation Example 8) organic light-emitting diodes were prepared by using the thermally activated delayed fluorescence compounds in Preparation Examples 1-10. Each of these organic light-emitting diodes exhibited a quantum efficiency of more than 5% (light extraction efficiency of 20%), which is the maximum external quantum efficiency that can be obtained from a general fluorescent device, indicating that the thermally activated delayed fluorescence compounds according to the examples of the present disclosure promote efficient reverse intersystem crossing from triplet to singlet. In some embodiments, the organic light-emitting diode according to Comparative Example 1 using CC2TA (which is referred to as a conventional delayed fluorescence luminescent material) exhibited a quantum efficiency of 11.5%, while the organic light-emitting diodes according to Preparation Examples 1 to 10 exhibited significantly higher or the same quantum efficiency. In particular, the green light-emitting device (Preparation Example 5) exhibited a high quantum efficiency of 17% or more, showing excellent or suitable light-emitting characteristics compared to conventional fluorescent devices.

[0642] Evaluation Example 1

[0643] Table 1 shows values ​​calculated by molecular calculation techniques for Compound 1, Comparative Compound A, and Comparative Compound B prepared according to Synthesis Example 1. Molecular calculations were performed on a 6-31G* basis set according to density functional theory by the B3LYP method using the Gaussian 09 program.

[0644] [Table 1]

[0645]

[0646]

[0647] Referring to Table 1, Comparative Compound A or Comparative Compound B is in a similar form to Compound 1, but carbazole as an electron-donating group and diphenyltriazine as an electron-withdrawing group are in the meta position in Comparative Compound A and in the para position in Comparative Compound B. The calculation results show that as the positions of carbazole and diphenyltriazine move from the ortho position to the meta position and from the meta position to the para position, the singlet energy gradually increases and the triplet energy gradually decreases. As a result, the minimum energy difference is found between the singlet state and the triplet state in the ortho form. The smaller the energy difference between the singlet state and the triplet state, the easier the reverse system crossing (RISC) is, and the better the thermally activated delayed fluorescence properties can be obtained.

[0648] Figure 2 Shown are molecular orbital distributions of Compound 1, Comparative Compound A, and Comparative Compound B prepared according to Synthesis Example 1. The molecular orbital distributions were calculated according to density functional theory using a 6-31G* basis set by the B3LYP method using the Gaussian 09 program.

[0649] In order to effectively show the fluorescence properties, the overlap between HOMO and LUMO should exist to a certain extent. As a result of the calculation, the HOMO and LUMO of the ortho-form, meta-form and para-form overlap on benzene as the central connecting unit, and the fluorescence properties of the ortho-form material are expected to be similar to those of other forms. These results show that, compared with the meta-form material and the para-form material, the ortho-form material can be more effectively converted to singlet excitons formed during electroluminescence by RISC, and the singlet excitons can show effective fluorescence emission.

[0650] Synthesis Example 13: Synthesis of Compound 93

[0651] Solution 9

[0652]

[0653] Synthesis of intermediate 93-1:

[0654] 9H-carbazole-1,2,3,4,5,6,7,8-d8 (CAS#=38537-24-5, (2 equivalents)) was dissolved in THF, reacted with nBuLi at 0°C, and then cyanuric chloride was added dropwise. Then, the mixture was stirred at 70°C overnight to obtain Intermediate 93-1. Intermediate 93-1 was confirmed by MS.

[0655] C 27 D 16 C1N 5 M+1 462.3

[0656] Synthesis of intermediate 93-2:

[0657] 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1 equivalent), 1-bromo-2-fluorobenzene (1.5 equivalents) and K 3 PO 4 (2 equiv.) was dissolved in DMF (N,N-dimethylformamide) and stirred overnight at 160° C. Intermediate 93-2 was confirmed by MS.

[0658] C 18 H 4 D 8 BrN M+1: 330.2

[0659] Synthesis of intermediate 93-3:

[0660] Intermediate 93-2 (1 equivalent) was dissolved in THF (tetrahydrofuran) and reacted with nBuLi (1.2 equivalent) at -78°C. After 1 hour, trimethyl borate was added dropwise. Then, the mixture was slowly heated to room temperature to obtain intermediate 93-3. Intermediate 93-3 was confirmed by MS.

[0661] C 18 H 6 D 8 BNO 2 M+1 295.3

[0662] Synthesis of compound 93:

[0663] 2.1g of intermediate 93-1, 1.6g of intermediate 93-3, 0.21g of tetrakis (triphenylphosphine) palladium (0) and 1.6g of potassium carbonate are put into a reaction vessel, and dissolved in 40mL of toluene, 10mL of ethanol and 10mL of distilled water, and then the mixture is refluxed for 24 hours. After the reaction is complete, the reaction solution is extracted with ethyl acetate, the organic layer collected by anhydrous magnesium sulfate drying, and the solvent is evaporated. The residue obtained by evaporation is separated and purified by silica gel column chromatography to obtain 1.8g (yield: 59%) of compound 93. Compound 93 is confirmed by LC-MS.

[0664] C 45 H 4 D 24 N 6 M+1: 677.4

[0665] Synthesis Example 14: Synthesis of Compound 94

[0666] Solution 10

[0667]

[0668] Synthesis of intermediate 94-1:

[0669] 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1 equivalent), 1-bromo-2-fluorobenzene-3,4,5,6-d4 (1.5 equivalent, CAS#=50592-35-3) and K 3 PO 4 (2 eq) was dissolved in DMF and stirred at 160°C overnight. Intermediate 94-1 was confirmed by MS.

[0670] C 18 D 12 BrN M+1: 334.0

[0671] Synthesis of intermediate 94-2:

[0672] Intermediate 94-1 (1 eq) was dissolved in THF and reacted with nBuLi (1.2 eq) at -78°C. After 1 hour, trimethyl borate (1.4 eq) was added dropwise. Then, the mixture was slowly heated to room temperature to obtain intermediate 94-2. Intermediate 94-2 was confirmed by MS.

[0673] C 18 H 2 D 12 BNO 2 M+1: 301.2

[0674] Synthesis of compound 94:

[0675] 3.7g of intermediate 93-1, 2.9g of intermediate 94-2, 0.37g of tetrakis (triphenylphosphine) palladium (0) and 2.8g of potassium carbonate are put into reaction vessel, and are dissolved in 80mL of toluene, 20mL of ethanol and 20mL of distilled water, and then the mixture is refluxed for 24 hours. After the reaction is completed, the reaction solution is extracted with ethyl acetate, the organic layer collected by anhydrous magnesium sulfate drying, and the solvent is evaporated. The residue obtained by evaporation is separated and purified by silica gel column chromatography to obtain 3.3g (yield: 61%) of compound 94. Compound 94 is confirmed by LC-MS.

[0676] C 45 D 28 N 6 M+1: 681.4

[0677] Synthesis Example 15: Synthesis of Compound 98

[0678] Solution 11

[0679]

[0680] Synthesis of intermediate 98-1:

[0681] 3-Bromo-9H-carbazole-1,2,4,5,6,7,8-d7 (CAS#=2764814-81-3) was reacted with CuCN in DMF solvent to obtain Intermediate 98-1. Intermediate 98-1 was confirmed by MS.

[0682] C 13 HD 7 N 2 M+1: 200.21

[0683] Synthesis of intermediate 98-2:

[0684] Intermediate 93-1 was reacted with 2-fluorophenylboronic acid (CAS#=1993-03-9) under Pd catalyst and basic conditions to obtain Intermediate 98-2. Intermediate 98-2 was confirmed by MS.

[0685] C 33 H 4 D 16 FN 5 M+1: 522.29

[0686] Synthesis of compound 98:

[0687] 1.3g of intermediate 98-1, 3.1g of intermediate 98-2, 3.1g of potassium phosphate and 50mL of DMF were placed in a reaction vessel and refluxed at 120°C for 12 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate, the collected organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue obtained by evaporation was separated and purified by silica gel column chromatography to obtain 2.6g (yield: 63%) of compound 98. Compound 98 was confirmed by LC-MS.

[0688] C 46 H 4 D 23 N 7 M+1:701.34

[0689] Synthesis Example 16: Synthesis of Compound 104

[0690] Solution 12

[0691]

[0692] Synthesis of intermediate 104-1:

[0693] 2-Chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (CAS#=1300115-09-6) and 2-fluorophenylboronic acid (CAS#=1993-03-9) were reacted under a Pd catalyst and basic conditions to obtain Intermediate 104-1. Intermediate 104-1 was confirmed by MS.

[0694] C 21 H 4 D 10 FN 3 M+1: 338.21

[0695] Synthesis of compound 104:

[0696] 4.1 g of intermediate 104-1, 2.7 g of intermediate 98-1, 6.4 g of K 3 PO 450mL of DMF was placed in a RBF (round bottom flask) and stirred at 120°C for 12 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate, the collected organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue obtained by evaporation was separated and purified by silica gel column chromatography to obtain 4.5g (yield: 72%) of compound 104. Compound 104 was confirmed by LC-MS.

[0697] C 34 H 4 D 17 N 5 M+1: 517.27

[0698] Synthesis Example 17: Synthesis of Compound 105

[0699] Solution 13

[0700]

[0701] Synthesis of intermediate 105-1:

[0702] 2-Bromo-9H-carbazole-1,3,4,5,6,7,8-d7 (CAS#=2650519-97-2) was reacted with CuCN in DMF solvent to obtain Intermediate 105-1. Intermediate 105-1 was confirmed by MS.

[0703] C 13 HD 7 N 2 M+1: 200.13

[0704] Synthesis of compound 105:

[0705] 3.7 g of intermediate 104-1, 2.4 g of intermediate 105-1, 5.8 g of K 3 PO 4 and DMF were placed in RBF and stirred at 120°C for 12 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate, the collected organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue obtained by evaporation was separated and purified by silica gel column chromatography to obtain 2.9 g (yield: 51%) of compound 105. Compound 105 was confirmed by LC-MS.

[0706] C 34 H 4 D 17 N 5 M+1: 517.28

[0707] Synthesis Example 18: Synthesis of Compound 114

[0708] Solution 14

[0709]

[0710] Synthesis of intermediate 114-1:

[0711] 9H-carbazole-1,2,3,4,5,6,7,8-d8 (CAS#=38537-24-5) was reacted with nBuLi and then with cyanuric chloride to obtain Intermediate 114-1. Intermediate 114-1 was confirmed by MS.

[0712] C 15 D 8 Cl 2 N 4 M+1: 323.08

[0713] Synthesis of intermediate 114-2:

[0714] Intermediate 114-1 and Intermediate 93-3 were reacted under a Pd catalyst and basic conditions to obtain Intermediate 114-2. Intermediate 114-2 was confirmed by MS.

[0715] C 33 H 4 D 16 C1N 5 M+1: 538.19

[0716] Synthesis of intermediate 114-3:

[0717] Intermediate 114-2 was reacted with 2-fluorophenylboronic acid (CAS#=1993-03-9) under Pd catalyst and basic conditions to obtain Intermediate 114-3. Intermediate 114-3 was confirmed by MS.

[0718] C 39 H 8 D 16 FN 5 M+1: 598.31

[0719] Synthesis of compound 114:

[0720] 2.1 g of intermediate 114-3, 0.77 g of intermediate 105-1, 1.9 g of K 3 PO 4 114 (yield: 77%) was purified by silica gel column chromatography.

[0721] C 52 H 8 D 23 N 7 M+1: 777.31

[0722] Synthesis Example 19: Synthesis of Compound 116

[0723] Solution 15

[0724]

[0725] Synthesis of intermediate 116-1:

[0726] 3-Bromo-9H-carbazole-1,2,4,5,6,7,8-d7 (CAS#=2764814-81-3) and (phenyl-d5)boronic acid (CAS#=215527-70-1) were reacted under Pd catalyst and basic conditions to obtain Intermediate 116-1. Intermediate 116-1 was confirmed by MS.

[0727] C 18 HD 12 N M+1: 256.21

[0728] Synthesis of compound 116:

[0729] 2.1 g of intermediate 114-3, 1 g of intermediate 116-1, 1.9 g of K 3 PO 4 and 30mL of DMF were placed in RBF and stirred overnight at 120°C. After the reaction was completed, the reaction solution was extracted with ethyl acetate, the collected organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue obtained by evaporation was separated and purified by silica gel column chromatography to obtain 1.4g (yield: 54%) of compound 116. Compound 116 was confirmed by LC-MS.

[0730] C 51 H 4 D 28 N 6 M+1: 757.42

[0731] Synthesis Example 20: Synthesis of Compound 120

[0732] Scheme 16

[0733]

[0734] Synthesis of compound 120:

[0735] 3.1g of intermediate 114-1, 7.3g of intermediate 94-2, 0.48g of tetrakis (triphenylphosphine) palladium (0) and 3.6g of potassium carbonate are put into a reaction vessel, and dissolved in 80mL of toluene, 20mL of ethanol and 20mL of distilled water, and then the mixture is refluxed for 24 hours. After the reaction is complete, the reaction solution is extracted with ethyl acetate, the organic layer collected by anhydrous magnesium sulfate drying, and the solvent is evaporated. The residue obtained by evaporation is separated, and purified by silica gel column chromatography to obtain 5.0g (yield: 64%) of compound 120. Compound 120 is confirmed by LC-MS.

[0736] C 51 D 32 N 6 M+1:761.49

[0737] Synthesis Example 21: Synthesis of Compound 121

[0738] Solution 17

[0739]

[0740] Synthesis of intermediate 121-1:

[0741] Intermediate 114-1 and Intermediate 94-2 were reacted under a Pd catalyst and basic conditions to obtain Intermediate 121-1. Intermediate 121-1 was confirmed by MS.

[0742] C 33 D 20 C1N 5 M+1: 542.29

[0743] Synthesis of intermediate 121-2:

[0744] 9H-carbazole-1,2,3,4,5,6,7,8-d8 (CAS#=38537-24-5) and 1,3-dibromo-2-fluorobenzene-4,5,6-d3 (CAS#=2768654-61-9) react under basic conditions to obtain Intermediate 121-2. Intermediate 121-2 was confirmed by MS.

[0745] C 18 D 11 Br 2 N M+1:410.98

[0746] Synthesis of intermediate 121-3:

[0747] Intermediate 121-2 and phenyl-d5-boronic acid (CAS#=215527-70-1) were reacted under Pd catalyst and basic conditions to obtain Intermediate 121-3. Intermediate 121-3 was confirmed by MS.

[0748] C 24 D 16 BrN M+1:414.13

[0749] Synthesis of intermediate 121-4:

[0750] Intermediate 121-3 was reacted with nBuLi (1.2 eq.) at -78 °C. The reaction solution was then reacted with B(OMe) 3 (1.4 equiv) was reacted to obtain intermediate 121-4. Intermediate 121-4 was confirmed by MS.

[0751] C 24 H 2 D 16 BNO 2 M+1: 380.23

[0752] Synthesis of compound 121:

[0753] 4.5g of intermediate 121-1, 3.8g of intermediate 121-4, 0.38g of tetrakis (triphenylphosphine) palladium (0) and 2.9g of potassium carbonate are put into a reaction vessel, and dissolved in 80mL of toluene, 20mL of ethanol and 20mL of distilled water, and then the mixture is refluxed for 24 hours. After the reaction is complete, the reaction solution is extracted with ethyl acetate, the organic layer collected by anhydrous magnesium sulfate drying, and the solvent is evaporated. The residue obtained by evaporation is separated, and purified by silica gel column chromatography to obtain 3.6g (yield: 52%) of compound 121. Compound 121 is confirmed by LC-MS.

[0754] C 57 D 36 N 6 M+1: 841.51

[0755] Synthesis Example 22: Synthesis of Compound 122

[0756] Scheme 18

[0757]

[0758] Synthesis of compound 122:

[0759] 2.9g of intermediate 114-1, 7.5g of intermediate 121-4, 0.41g of tetrakis (triphenylphosphine) palladium (0) and 3.1g of potassium carbonate are put into a reaction vessel, and dissolved in 80mL of toluene, 20mL of ethanol and 20mL of distilled water, and then the mixture is refluxed for 24 hours. After the reaction is complete, the reaction solution is extracted with ethyl acetate, the organic layer collected by anhydrous magnesium sulfate drying, and the solvent is evaporated. The residue obtained by evaporation is separated, and purified by silica gel column chromatography to obtain 5.9g (yield: 71%) of compound 122. Compound 122 is confirmed by LC-MS.

[0760] C 63 D 40 N 6 M+1: 921.57

[0761] Evaluation Example 2

[0762] Table 2 shows values ​​calculated by molecular calculation techniques for the compounds prepared according to Synthesis Examples 13 to 22 and Comparative Compounds C1 to C4. Molecular calculations were performed on a 6-31G* basis set by density functional theory using the Gaussian 09 program by the B3LYP method.

[0763] [Table 2]

[0764]

[0765]

[0766]

[0767] Referring to Table 2, Comparative Compound C1, Comparative Compound C2, Comparative Compound C3 or Comparative Compound C4 are in a form similar to that of the compound represented by Chemical Formula 2 disclosed, but the electron-donating group and the electron-withdrawing group are in the meta position in Comparative Compound C1 and Comparative Compound C3 and in the para position in Comparative Compound C2 and Comparative Compound C4, and Comparative Compound C1 to Comparative Compound C4 do not contain deuterium. The calculation results show that the minimum energy difference is found between the singlet state and the triplet state in the ortho form. The smaller the energy difference between the singlet state and the triplet state, the easier the reverse system crossing (RISC) is, and better thermally activated delayed fluorescence properties can be obtained.

[0768] In order to effectively show the fluorescence properties, the overlap between HOMO and LUMO should exist to a certain extent. As a result of the calculation, the HOMO and LUMO of the ortho-form, meta-form and para-form overlap on benzene as the central connecting unit, and the fluorescence properties of the ortho-form material are expected to be similar to those of other forms. These results show that, compared with the meta-form material and the para-form material, during electroluminescence, the ortho-form material can more effectively convert the triplet exciton formed by RISC to a singlet exciton, and the singlet exciton can show effective fluorescence emission.

[0769] In the disclosed compound represented by Chemical Formula 2, an electron donating group and an electron withdrawing group are introduced at the ortho position of the benzene ring. In addition, in the disclosed compound represented by Chemical Formula 2, R 1 , R 2 , R 17 and R 18 At least one of which includes deuterium, or R 22 To R 25 At least one of them is deuterium. Therefore, the compound can have a high T 1 energy level, so that it can effectively block the excitons of the dopant, and the compound can have a small ΔE ST The value of the dopant is such that energy transfer from the host to the dopant can be facilitated. Therefore, a light-emitting device including the compound can have excellent characteristics in terms of driving voltage and maximum quantum efficiency.

[0770] Preparation Example 11: Preparation of Light Emitting Device

[0771] For the anode, Corning 15Ω / cm 2 The ITO glass substrate was cut into a size of 50 mm×50 mm×0.5 mm, ultrasonicated with isopropyl alcohol and pure water for 5 minutes, respectively, and then cleaned by ultraviolet rays and ozone for 30 minutes. The obtained glass substrate was provided to a vacuum deposition device.

[0772] On a glass substrate, HAT-CN was applied to the substrate to form a Then, the first hole transport material BCFN is vacuum deposited onto Then, a second hole transport material SiCzCz is vacuum deposited onto to form a hole transport layer.

[0773] On the hole transport layer, SiCzCz and compound 93 as a mixed host and PtON-TBBI as a phosphorescent dopant were co-deposited in a weight ratio of 60:27:13 to form a The thickness of the emission layer.

[0774] Subsequently, on the emission layer, mSiTrz is deposited to After the first electron transport layer is formed, mSiTrz and Liq are co-deposited as a mixture in a weight ratio of 1:1 to form a On the electron transport layer, LiF (alkali metal halide) is deposited to form an electron transport layer having a thickness of The electron injection layer is formed by vacuum depositing Al to A thickness of is used to form a LiF / Al electrode, thereby completing the manufacture of the light-emitting device.

[0775]

[0776] Preparation Examples 12 to 20 and Comparative Examples 2 to 5

[0777] A light-emitting device was manufactured in substantially the same manner as in Preparation Example 11, except that the compounds shown in Table 2 were each used instead of Compound 93 in forming the emission layer.

[0778] Evaluation Example 3

[0779] For the light emitting devices manufactured according to Preparation Examples 11 to 20 and Comparative Examples 2 to 5, the 10 mA / cm 2 The driving voltage (V) and maximum quantum efficiency (%) at a current density of , and the results are shown in Table 3.

[0780] The driving voltage and current density of the light emitting device were measured using a source meter (Keithley Instrument, 2400 series), and the maximum quantum efficiency was measured using an external quantum efficiency measurement device (Hamamatsu Photonics, C9920-2-12). In the evaluation of the maximum quantum efficiency, the brightness / current density was measured using a brightness meter with wavelength sensitivity calibration, and the maximum quantum efficiency was calculated assuming a Lambertian angular brightness distribution with a perfect diffuse reflection surface. The evaluation results of the characteristics of the organic light emitting device are shown in Table 3 below.

[0781] [Table 3]

[0782]

[0783]

[0784]

[0785]

[0786] It can be confirmed from Table 3 that, compared with the light emitting devices according to Comparative Examples 2 to 5, the light emitting devices according to Examples 11 to 20 have excellent characteristics in terms of driving voltage and maximum quantum efficiency.

[0787] According to one or more embodiments, the light emitting device may have excellent characteristics in terms of driving voltage and maximum quantum efficiency by including the compound represented by Chemical Formula 2. In addition, high-quality electronic devices and electronic apparatuses may be manufactured by using the light emitting device.

[0788] The present disclosure is not limited to the above embodiments and drawings. Although the exemplary embodiments of the present disclosure and their advantages have been described in more detail, it should be understood that one or more suitable changes, substitutions and alterations may be made therein without departing from the scope of the present disclosure.

Claims

1. A luminescent material, the luminescent material is represented by Chemical Formula 2: Chemical formula 2 in, In chemical formula 2, R1 and R2 are independently substituted or unsubstituted C1-C9 alkyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C7-C 30 Alkaryl, substituted or unsubstituted C7-C 30 Arylalkyl or substituted or unsubstituted C3-C 30 heteroaryl; and R1 and R2 are optionally combined with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl, R 17 and R 18 are independently cyano, substituted or unsubstituted C1-C9 alkyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C7-C 30 Alkaryl, substituted or unsubstituted C7-C 30 Arylalkyl, substituted or unsubstituted C3-C 30 Heteroaryl, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 Aryloxy, C1-C9 alkylsilyl or substituted or unsubstituted -NR a R b , R a and R b are independently hydrogen, deuterium, substituted or unsubstituted C1-C9 alkyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C7-C 30 Arylalkyl or substituted or unsubstituted C3-C 30 heteroaryl; and R a and R b are optionally combined with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl, and R 22 To R 25 are independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted C4-C6 heteroaryl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted C1-C3 alkyl group, Among them, selected from R1, R2, R 17 and R 18 At least one of includes deuterium, or is selected from R 22 To R 25 At least one of them is deuterium.

2. The luminescent material according to claim 1, in, In Chemical Formula 2, R1 and R2 are combined together with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heteroaryl group.

3. The luminescent material according to claim 1, in, In Chemical Formula 2, R1 and R2 are combined together with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heteroaryl group represented by any one of Structural Formulas A1 to A6 and A9 to A19: Among them, in structural formulas A1 to A6 and structural formulas A9 to A19, R 11 To R 14 are independently hydrogen, deuterium, substituted or unsubstituted C1-C2 alkyl or substituted or unsubstituted C6-C 30 Aryl, Sub1 and Sub2 are independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C7-C 30 Alkaryl, substituted or unsubstituted C3-C 30 heteroaryl, substituted or unsubstituted C1-C9 alkoxy, substituted or unsubstituted -NR c R d , substituted or unsubstituted silyl, substituted or unsubstituted phosphine, substituted or unsubstituted phosphine oxide, substituted or unsubstituted thiol, substituted or unsubstituted sulfoxide, substituted or unsubstituted sulfone, substituted or unsubstituted C6-C 30 Arylsilyl, substituted or unsubstituted C6-C 30 Arylthio, substituted or unsubstituted C6-C 30 Aryloxy, substituted or unsubstituted C6-C 30 Arylamine or substituted or unsubstituted C7-C 30 Aralkyl, R c and R d are independently selected from the group consisting of: substituted or unsubstituted C1-C9 alkyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C7-C 30 Arylalkyl and substituted or unsubstituted C3-C 30 heteroaryl, and R c and R d are optionally combined with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl, and Sub1 and Sub2 are independently of each other and optionally fused to the host to which they are bound to form a substituted or unsubstituted cyclic group or a substituted or unsubstituted aryl group.

4. The luminescent material according to claim 1, in, In Chemical Formula 2, R1 and R2 are combined together with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heteroaryl group represented by any one of Structural Formulas A1 to A45: Among them, in structural formula A1 to structural formula A45, R 11 To R 14 are independently hydrogen, deuterium, substituted or unsubstituted C1-C2 alkyl or substituted or unsubstituted C6-C 30 Aryl, and Sub1 to Sub4 are independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C7-C 30 Alkaryl, substituted or unsubstituted C7-C 30 Arylalkyl, substituted or unsubstituted C3-C 30 heteroaryl, substituted or unsubstituted C1-C9 alkoxy, substituted or unsubstituted C6-C 30 an aryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted thiol group, a substituted or unsubstituted sulfoxide group or a substituted or unsubstituted sulfone group.

5. The luminescent material according to claim 4, in, In Structural Formulae A1 to A45, Sub1 to Sub4 are independently hydrogen, deuterium, a halogen group or a cyano group.

6. The luminescent material according to claim 1, in, In chemical formula 2, R 17 and R 18 are independently cyano, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C3-C 30 heteroaryl or substituted or unsubstituted -NR a R b ,and R a and R b are independently hydrogen, deuterium, substituted or unsubstituted C1-C9 alkyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C7-C 30 Arylalkyl or substituted or unsubstituted C3-C 30 heteroaryl; and R a and R b Optionally combined with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl.

7. The luminescent material according to claim 1, in, In formula 2, the substitutions are R 17 and R 18 The triazine group is represented by any one of the structural formulas B1 to B13, B50 and B51: Among them, in formulas B1 to B13, B50 and B51, R 11 and R 12 are independently hydrogen, deuterium or substituted or unsubstituted C1-C2 alkyl, Sub5 and Sub6 are independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C3-C 30 heteroaryl, substituted or unsubstituted C1-C9 alkoxy, substituted or unsubstituted -NR e R f , substituted or unsubstituted silyl, substituted or unsubstituted phosphine, substituted or unsubstituted phosphine oxide, substituted or unsubstituted thiol, substituted or unsubstituted sulfoxide, substituted or unsubstituted sulfone, substituted or unsubstituted C6-C 30 Arylthio, substituted or unsubstituted C6-C 30 Aryloxy, substituted or unsubstituted C6-C 30 Arylamine or substituted or unsubstituted C7-C 30 aralkyl, and Sub5 and Sub6 are each independently optionally fused to the subject to which they are bound to form a substituted or unsubstituted cyclic group or a substituted or unsubstituted aryl group, and R e and R f are independently selected from the group consisting of: substituted or unsubstituted C1-C9 alkyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C7-C 30 Alkaryl, substituted or unsubstituted C7-C 30 Arylalkyl and substituted or unsubstituted C3-C 30 heteroaryl, and R e and R f Optionally combined with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl.

8. The luminescent material according to claim 1, in, In formula 2, the substitutions are R 17 and R 18 The triazine group is represented by any one of the structural formulas B8 to B12, B50 and B51: Among them, in structural formulas B8 to B12, structural formula B50 and structural formula B51, R 11 and R 12 are independently hydrogen, deuterium or substituted or unsubstituted C1-C2 alkyl, and Sub5 and Sub6 are independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C3-C 30 heteroaryl, substituted or unsubstituted C1-C9 alkoxy, substituted or unsubstituted silyl, substituted or unsubstituted phosphino, substituted or unsubstituted phosphine oxide, substituted or unsubstituted thiol, substituted or unsubstituted sulfoxide, substituted or unsubstituted sulfone, substituted or unsubstituted C6-C 30 Arylthio, substituted or unsubstituted C6-C 30 Aryloxy, substituted or unsubstituted C6-C 30 Arylamine or substituted or unsubstituted C7-C 30 aralkyl; and Sub5 and Sub6 are independently of each other optionally fused to the subject to which they are bound to form a substituted or unsubstituted cyclic group or a substituted or unsubstituted aryl group.

9. The luminescent material according to claim 1, in, In formula 2, the substitutions are R 17 and R 18 The triazine group is represented by any one of the structural formula B12 and the structural formula B50 to the structural formula B54: Among them, in structural formula B12 and structural formula B50 to structural formula B54, Sub5 to Sub8 are independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C6-C 30 Aryl or substituted or unsubstituted C3-C 30 Heteroaryl.

10. The luminescent material according to claim 1, in, In chemical formula 2, R 22 To R 25 independently of each other is hydrogen or deuterium.

11. The luminescent material according to claim 1, in, The light emitting material represented by Chemical Formula 2 is represented by any one of Compound 93 to Compound 122:

12. A light emitting device, comprising: a first electrode; a second electrode, facing the first electrode; an intermediate layer disposed between the first electrode and the second electrode and including an emission layer; and The luminescent material is represented by chemical formula 2: Chemical formula 2 Wherein, in Chemical Formula 2, R1 and R2 are independently substituted or unsubstituted C1-C9 alkyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C7-C 30 Alkaryl, substituted or unsubstituted C7-C 30 Arylalkyl or substituted or unsubstituted C3-C 30 heteroaryl; and R1 and R2 are optionally combined with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl, R 17 and R 18 are independently cyano, substituted or unsubstituted C1-C9 alkyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C7-C 30 Alkaryl, substituted or unsubstituted C7-C 30 Arylalkyl, substituted or unsubstituted C3-C 30 Heteroaryl, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 Aryloxy, C1-C9 alkylsilyl or substituted or unsubstituted -NR a R b , R a and R b are independently hydrogen, deuterium, substituted or unsubstituted C1-C9 alkyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C7-C 30 Arylalkyl or substituted or unsubstituted C3-C 30 heteroaryl; and R a and R b are optionally combined with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl, and R 22 To R 25 are independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted C4-C6 heteroaryl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted C1-C3 alkyl group, Among them, selected from R1, R2, R 17 and R 18 At least one of includes deuterium, or is selected from R 22 To R 25 At least one of them is deuterium.

13. The light emitting device according to claim 12, wherein: The emission layer includes the light emitting material represented by Chemical Formula 2.

14. The light emitting device according to claim 12, wherein: The emission layer includes a host and a dopant, and The host includes the light emitting material represented by Chemical Formula 2.

15. The light emitting device according to claim 14, in, The host is a delayed fluorescent light-emitting material.

16. The light emitting device according to claim 12, further comprising: A first cover layer, arranged outside the first electrode; as well as a second capping layer, arranged outside the second electrode, Wherein, the first capping layer or the second capping layer includes the light-emitting material represented by Chemical Formula 2. 17 . An electronic device comprising the light emitting device according to claim 12 .

18. The electronic device according to claim 17, further comprising: a thin film transistor electrically connected to the light emitting device; as well as Color filters, color conversion layers, touch screen layers, polarizing layers, or any combination thereof.

19. An electronic device comprising the light emitting device according to any one of claims 12 to 16.

20. The electronic device according to claim 19, wherein: The electronic device is a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, indoor or outdoor lighting, a signal light, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a phone, a tablet personal computer, a tablet phone, a personal digital assistant, a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a three-dimensional display, a virtual reality or augmented reality display, a vehicle, a video wall with multiple displays stitched together, a theater or stadium screen, a light therapy device, or a sign.

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