Ortho-substituted thermally activated delayed fluorescence material and organic light-emitting device comprising same

Abstract

To provide a thermally activated delayed fluorescent material, which can improve quantum efficiency as the transition from a triplet state to a single state can be more efficiently performed.SOLUTION: According an embodiment of the invention, there is provided a thermally activated delayed fluorescent (TADF) material. The TADF 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 positioned in an ortho position to the electron donating group.SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] The present invention relates 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 technology]

[0002] OLEDs (organic light emitting devices) are self-emitting devices that have a fast response time, excellent or suitable luminance, driving voltage and response speed characteristics, and can realize a wide viewing angle and excellent or suitable brightness / dark ratio, as well as multi-color realization.

[0003] A typical organic light-emitting diode includes an anode, a cathode, and an organic layer interposed between the anode and the cathode. The organic layers include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, 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. In the light-emitting layer, carriers such as holes and electrons recombine to generate excitons, which transition to a bottom state and emit light.

[0004] When an organic light-emitting diode is driven, the excitons generated are probabilistically 25% in the singlet state and 75% in the triplet state. In the case of fluorescent materials, only singlet-state excitons, which account for 25% of the total excitons, are involved in light emission, and the internal quantum efficiency remains at a maximum of 25%. To improve such properties, iridium or platinum complexes that promote emission from triplet excitons are utilized, enabling excellent or suitable quantum efficiency properties. However, these materials are expensive, and their applications are limited by the instability of blue-emitting materials.

[0005] To solve such problems, thermally activated delayed fluorescent organic materials have been developed recently. The thermally activated delayed fluorescent organic materials have an energy difference between the singlet and triplet states of excitons of 0.3 eV or less. In this case, upconversion from the triplet state to the singlet state is possible by heat corresponding to room temperature or device operating temperature, so that a theoretical quantum efficiency of nearly 100% can be achieved. Summary of the Invention [Problem to be solved by the invention]

[0006] However, it is known that the actual quantum efficiency of currently developed thermally activated delayed fluorescent organic materials is significantly different from the theoretical quantum efficiency, and there is still a need for improvement. [Means for solving the problem]

[0007] An object of one embodiment of the present invention is to provide a thermally activated delayed fluorescent material capable of more efficiently transitioning from a triplet state to a singlet state to improve quantum efficiency, and an organic light-emitting diode including the same.

[0008] In some exemplary embodiments, a thermally activated delayed fluorescent (TADF) material is provided. The TADF material has a structure in which an electron donating group and an electron withdrawing group are linked to benzene, and the electron withdrawing group is located at the ortho position to the electron donating group. Effect of the Invention

[0009] According to one embodiment of the present invention, a compound having an electron donating group and an electron withdrawing group introduced at the ortho position of a benzene ring can reduce the energy difference between a singlet excited state and a triplet excited state, and thus can easily undergo upconversion from a triplet excited state to a singlet excited state through thermal reverse intersystem crossing at room temperature or at a device operating temperature, thereby generating delayed fluorescence.

[0010] Exemplary embodiments of the present invention will become more apparent from a more particular description of the exemplary embodiments of the present invention taken in conjunction with the accompanying drawings, in which: FIG. [Brief description of the drawings]

[0011] [Figure 1] 1 is a cross-sectional view showing an organic light-emitting diode according to an embodiment of the present invention. [Diagram 2] 1 is a diagram showing molecular orbital distributions of Compound 1 prepared in Synthesis Example 1, Comparative Compound 2, and Comparative Compound 3. [Diagram 3] 1 is a diagram illustrating a schematic structure of a light emitting device according to an embodiment. [Figure 4] 1 is a diagram illustrating a schematic structure of an electronic device according to an embodiment. [Diagram 5] 1 is a diagram illustrating a schematic structure of an electronic device according to an embodiment. [Figure 6] 1 is a schematic diagram of an electronic device including a light emitting device according to an embodiment. [Figure 7] 1 is a schematic view illustrating the exterior of a vehicle as an electronic device including a light emitting device according to an embodiment. [Figure 8A] 1 is a schematic diagram illustrating the interior of a vehicle according to various embodiments. [Figure 8B] 1 is a schematic diagram illustrating the interior of a vehicle according to various embodiments. [Figure 8C] 1 is a schematic diagram illustrating the interior of a vehicle according to various embodiments. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] The present invention will be described in more detail below with reference to various aspects and one or more suitable exemplary embodiments. Hereinafter, the embodiments of the present invention will be described in more detail with reference to the accompanying drawings. The embodiments described below may be modified in various different forms, and the scope of the present invention is not limited to the above-described embodiments. Rather, the embodiments are provided to fully and completely describe the present disclosure and fully convey the scope of the present disclosure to those skilled in the art. In the drawings, the same reference numerals refer to the same elements.

[0013] The term "alkyl group" as used herein means an aliphatic hydrocarbon group unless otherwise defined. The alkyl group is a saturated alkyl group that does not contain any double or triple bonds. Alternatively, the alkyl group is an unsaturated alkyl group that contains at least one double or triple bond. Whether saturated or unsaturated, the alkyl group is branched, linear or cyclic. The alkyl group is a C1-C30 alkyl group. More specifically, the alkyl group is a C1-C10 alkyl group or a C1-C6 alkyl group. For example, the C1-C4 alkyl group may be selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, iso-butyl, sec-butyl and t-butyl.

[0014] The term "aryl group," as used herein, unless otherwise defined, means a monocyclic aromatic group or a polycyclic aromatic group containing fused aromatic rings, and includes heteroaryl groups.

[0015] The term "heteroaryl group," as used herein, unless otherwise defined, is a monocyclic aromatic group or a polycyclic aromatic group containing fused aromatic rings, in which at least one ring contains N, O, S, Se, and P.

[0016] The term "halogen group" as used herein, unless otherwise defined, means a Group 7 element, such as F, Cl, Br, or I. For example, the halogen group can be F.

[0017] In the present specification, when "Cx-Cy" is described, the number of carbon atoms corresponding to all integers between x and y should be interpreted as described.

[0018] Thermally activated delayed fluorescence (TADF) materials The following formula 1 shows a compound according to one embodiment of the present invention.

[0019] [Chemical formula 1] JPEG2025011064000002.jpg3539

[0020] In the above Chemical Formula 1, R EDG is an electron donating group, R EWG is an electron-withdrawing group, R 5 ~R 8 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted fused arylamine group, a substituted or unsubstituted phosphine or phosphine oxide group, a substituted or unsubstituted thiol group, a substituted or unsubstituted sulfoxide group, or a sulfone group.

[0021] The electron donating group is a substituted or unsubstituted amine group and the electron withdrawing group is a substituted or unsubstituted triazine group.

[0022] The compound represented by Formula 1 may be a light-emitting material. For example, it may be a TADF (Thermal Activated Delay Fluorescent) material exhibiting thermally activated delayed fluorescence. More specifically, it is 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, and may also be used as a host material in an emission layer.

[0023] The compound represented by Chemical Formula 1 has a form in which an electron donating group and an electron withdrawing group are bonded to benzene, and the electron withdrawing group is located at a position adjacent to the electron donating group (ortho position). Therefore, by introducing an electron donating group and an electron withdrawing group into the ortho position of benzene, it is possible to control the overlap of the HOMO (highest occupied molecular orbital) and the LUMO (lowest unoccupied molecular orbital) through the steric hindrance effect, and to reduce the difference between the singlet energy (S1) and the triplet energy (T1). For example, a compound in which an electron donating group and an electron withdrawing group are introduced into the ortho position of a benzene ring minimizes or reduces the energy difference between the singlet excited state and the triplet excited state (less than 0.3 eV), and therefore, upconversion, in which the triplet excited state is switched to the singlet excited state through thermal reverse intersystem crossing at room temperature or the device operating temperature, can easily occur, thereby generating delayed fluorescence.

[0024] Specific examples of the compound represented by Chemical Formula 1 may be represented by any one of Chemical Formulas 2 to 4 below.

[0025] [Chemical formula 2] JPEG2025011064000003.jpg45170

[0026] [Chemical formula 3] JPEG2025011064000004.jpg34170

[0027] [Chemical formula 4] JPEG2025011064000005.jpg54170

[0028] In the above Chemical Formulas 2 to 4, R 1 ~R 12 are each independently a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C6-C30 aralkyl group, or a substituted or unsubstituted C3-C30 heteroaryl group; R 1 and R 2 , R 3 and R 4 , R 5 and R 6 , R 7 and R 8 , R 9 and R 10 , or R 11 and R 12 can optionally form, together with the nitrogen to which they are attached, a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heteroaryl group. For example, in Formula 2 above, R 1 and R 2 can together with the nitrogen to which they are attached form a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted heteroaryl group.

[0029] In the above Chemical Formulas 2 to 4, R 17 ~R 19 are functional groups linked to the triazine group via carbon, nitrogen, oxygen, silicon, sulfur, or phosphorus, and each independently represents a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C30 alkyloxy group, a substituted or unsubstituted C3-C30 aryloxy group, a C1-C9 alkylsilyl group, or a substituted or unsubstituted -NR a R b The above R a and R bmay be independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group, or a substituted or unsubstituted C3-C30 heteroaryl group. a and R b can optionally form, together with the nitrogen to which they are attached, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted heteroaryl group.

[0030] R 22 ~R 45 Each of them is R defined in Formula 1 above. 5 ~R 8 For example, R 22 ~R 45 are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted C4-C6 aryl group, or a substituted or unsubstituted C1-C3 alkyl group. Here, the substituted C1-C3 alkyl group is a C1-C3 alkyl group substituted with a halogen, and the halogen group is F. For example, in the above formula 2, R 22 ~R 25 are, independently of each other, hydrogen or deuterium.

[0031] In the above formula 2, R 1 , R 2 , R 17 and R 18 At least one of the groups contains deuterium or R 22 ~R 25 At least one of the is deuterium.

[0032] The electron donating group in the above chemical formula 1, or -NR 1 R 2 , -NR 3 R 4 , -NR 5 R 6 , -NR 7 R 8 , -NR 9 R10 , or -NR 11 R 12 are each independently any one of structural formulas A1 to A19. For example, they can be A6, A8, A9 or A10. For example, in the above chemical formula 2, R 1 and R 2 can form, together with the nitrogen to which they are attached, 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:

[0033] JPEG2025011064000006.jpg179170

[0034] In the structural formulas A1 to A19, R 1 is R in the above Chemical Formula 2 1 is the same as R 11 ~R 14 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C2 alkyl group, or a substituted or unsubstituted C6-C30 aryl group; Sub 1 and Sub 2 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C9 alkyloxy group, a substituted or unsubstituted -NR c R d, 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, a substituted or unsubstituted sulfone group, a substituted or unsubstituted C5-C30 arylsilyl group, a substituted or unsubstituted C5-C30 arylthio group, a substituted or unsubstituted C5-C30 aryloxy group, a substituted or unsubstituted C5-C30 arylamine group, or a substituted or unsubstituted C5-C30 aralkyl group. For example, in the above Chemical Formula 2, Sub 1 and Sub 2 are each independently hydrogen, deuterium, a halogen group, or a cyano group. 1 and Sub 2 There can be multiple instances of each independently of each other. For example, Sub 1 and Sub 2 R may be present independently of one another 2, 3, 4 or 5 times. c and R d may be independently selected from the group consisting of a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group, or a substituted or unsubstituted C3-C30 heteroaryl group. c and R d can optionally form, together with the nitrogen to which they are attached, a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heteroaryl group. 1 and Sub 2 may, independently of each other, be selectively fused to the entity to which they are attached to form a substituted or unsubstituted ring group, or a substituted or unsubstituted aryl group. 1 and Sub 2When at least one of is a substituted or unsubstituted C5-C30 arylsilyl group, a substituted or unsubstituted C5-C30 arylthio group, a substituted or unsubstituted C5-C30 aryloxy group, a substituted or unsubstituted C5-C30 arylamine group, or a substituted or unsubstituted C5-C30 aralkyl group, the aryl group contained therein can be fused to the main body to form a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heteroaryl group.

[0035] The electron donating group in the above chemical formula 1, or -NR 1 R 2 , -NR 3 R 4 , -NR 5 R 6 , -NR 7 R 8 , -NR 9 R 10 , -NR 11 R 12 are each independently any one of the structural formulae A20 to A38. In particular, structural formula A9 is any one of the structural formulae A20 to A38 below.

[0036] JPEG2025011064000007.jpg214170

[0037] In the structural formulae A20 to A38, R 11 ~R 14 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C2 alkyl group, or a substituted or unsubstituted C6-C30 aryl group; Sub 1 ~Sub 4are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C9 alkyloxy group, a substituted or unsubstituted C6-C30 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. For example, in the above chemical formula 2, Sub 1 ~Sub 4 are each independently hydrogen, deuterium, a halogen group, or a cyano group. 1 ~Sub 4 There can be multiple instances of each independently of each other. For example, Sub 1 ~Sub 4 may be present 2, 3 or 4 times, independently of each other.

[0038] The electron donating group in the above chemical formula 1, or -NR 1 R 2 , -NR 3 R 4 , -NR 5 R 6 , -NR 7 R 8 , -NR 9 R 10 , -NR 11 R 12 are each independently any one of structural formulae A39 to A45. In particular, structural formula A10 is any one of structural formulae A39 to A45 below.

[0039] JPEG2025011064000008.jpg85170

[0040] In the structural formulae A39 to A45, R 11 ~R14 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C2 alkyl group, or a substituted or unsubstituted C6-C30 aryl group; Sub 1 ~Sub 4 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C9 alkyloxy group, a substituted or unsubstituted C6-C30 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. For example, in the above chemical formula 2, Sub 1 ~Sub 4 are each independently hydrogen, deuterium, a halogen group, or a cyano group. 1 ~Sub 4 There can be multiple instances of each independently of each other. For example, Sub 1 ~Sub 4 may be present 2, 3 or 4 times, independently of each other.

[0041] In the above formula 2, R 17 and R 18 Examples of the aryl group are, independently of each other, a cyano group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, or a substituted or unsubstituted -NR a R b and R a and R bare each independently hydrogen, deuterium, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group, or a substituted or unsubstituted C3-C30 heteroaryl group; a and R b can optionally form, together with the nitrogen to which they are attached, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted heteroaryl group.

[0042] The electron-withdrawing group in the above formula 1 or R in the above formula 2 17 and R 18 Examples of the triazine group substituted with R are the same as those in the following structural formulas B1 to B14, B50 and B51. For example, R 17 and R 18 The triazine group substituted with is the same as any one of the structural formulas B8 to B12, B50, and B51.

[0043] JPEG2025011064000009.jpg130170

[0044] In the structural formulae B1 to B14, B50 and B51, R 11 and R 12 are, independently of each other, hydrogen, deuterium, or a substituted or unsubstituted C1-C2 alkyl group; Sub 5 and Sub 6 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C9 alkyloxy group, a substituted or unsubstituted -NR e R f, 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, a substituted or unsubstituted sulfone group, a substituted or unsubstituted C5-C30 arylthio group, a substituted or unsubstituted C5-C30 aryloxy group, a substituted or unsubstituted C5-C30 arylamine group, or a substituted or unsubstituted C5-C30 aralkyl group. 5 and Sub 6 There can be multiple instances of each independently of each other. For example, Sub 5 and Sub 6 may be present independently of one another 2, 3, 4, 5, 6, 7 or 8 times. 5 and Sub 6 may, independently of each other, be selectively fused to the entity to which they are attached to form a substituted or unsubstituted ring group, or a substituted or unsubstituted aryl group. 5 or Sub 6 is a substituted or unsubstituted C5-C30 arylthio group, a substituted or unsubstituted C5-C30 aryloxy group, a substituted or unsubstituted C5-C30 arylamine group, or a substituted or unsubstituted C5-C30 aralkyl group, the aryl group contained therein can be fused to the main body to form a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heteroaryl group.

[0045] R e and R f R may be independently selected from the group consisting of a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C6-C30 aralkyl group, or a substituted or unsubstituted C3-C30 heteroaryl group. e and R f can optionally form, together with the nitrogen to which they are attached, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted heteroaryl group.

[0046] The electron-withdrawing group in the above formula 1 or R in the above formula 2 17 and R 18 Examples of the triazine group substituted with are the same as those in the following structural formulae B15 to B27. In particular, structural formula B12 is any one of the following structural formulae B15 to B27.

[0047] JPEG2025011064000010.jpg164170

[0048] In the structural formulas B15 to B27, R 11 and R 12 are each independently hydrogen, deuterium, or a substituted or unsubstituted C1-C2 alkyl group.

[0049] R in the above Chemical Formula 2 17 and R 18 Examples of the triazine group substituted with are the same as those in the following structural formulae B12 and B50 to B54.

[0050] JPEG2025011064000011.jpg110170

[0051] In the structural formulas B12 and B50 to B54, Sub 5 ~Sub 8 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group. For example, Sub 7 and Sub 8 are each independently hydrogen, deuterium, a halogen group, or a cyano group.

[0052] R in the above Chemical Formula 3 19 Examples of the triazine group substituted with are the same as those of the following structural formulas B28 to B49.

[0053] JPEG2025011064000012.jpg174170

[0054] In the structural formulas B28 to B49, R 11 and R 12 independently represent hydrogen, deuterium, or a substituted or unsubstituted C1-C2 alkyl group.

[0055] A specific example of the compound represented by Chemical Formula 2 is represented by Chemical Formula 5 below, and a specific example of the compound represented by Chemical Formula 3 is represented by Chemical Formula 6 below.

[0056] [Chemical formula 5] JPEG2025011064000013.jpg5046

[0057] In the above formula 5, R 1 , R 2 and R 22 ~R 25 is the same as defined in Formula 2, specifically, -NR 1 R 2 is any one of structural formulas A1 to A45, for example, A6, A9 or A10.

[0058] In the above Chemical Formula 5, Sub 5 and Sub 6 is the same as defined in structural formulas B12, B50 to B54. For example, Sub 5 and Sub 6 At least one of them is -NR e R f For example, Sub 5 and Sub 6 One of the following is -NR e R f and -NR e R f When is located at the ortho position relative to the triazine group, the compound of Chemical Formula 5 is the same as the compound represented by Chemical Formula 6. 5 and Sub 6 Both are -NR e R f and these -NR e R fare both located at the ortho position relative to the triazine group, the compound of Chemical Formula 5 is the same as the compound represented by Chemical Formula 4.

[0059] For example, the example of the triazine group in the above Chemical Formula 5 is the same as any one of the above Structural Formulas B12, B15 to B27.

[0060] For example, the example of the triazine group in the chemical formula 5 is the same as any one of the structural formulas B12, B50 to B54.

[0061] [Chemical formula 6] JPEG2025011064000014.jpg4253

[0062] In the above formula 6, R 3 , R 4 , R 5 , R 6 , R 26 ~R 29 , and R 30 ~R 33 is the same as defined in Chemical Formula 3. For example, NR 3 R 4 and N.R. 5 R 6 are each independently any one of structural formulae A1 to A45, for example, A6, A8, A9 or A10.

[0063] In the above Chemical Formula 6, Sub 5 is the same as defined in Structural Formula B11. For example, an example of the triazine group in Chemical Formula 6 is the same as any one of Structural Formulas B34 to B47.

[0064] Specific examples of the compound represented by Chemical Formula 2 may be represented by any one of Chemical Formulas 7 to 10 below.

[0065] [Chemical formula 7] JPEG2025011064000015.jpg58170

[0066] [Chemical formula 8] JPEG2025011064000016.jpg59170

[0067] [Chemical formula 9] JPEG2025011064000017.jpg58170

[0068] [Chemical formula 10] JPEG2025011064000018.jpg58170

[0069] A specific example of the compound represented by Formula 3 may be represented by Formula 11 below.

[0070] [Chemical formula 11] JPEG2025011064000019.jpg36170

[0071] A specific example of the compound represented by Formula 4 may be represented by Formula 12 below.

[0072] [Chemical formula 12] JPEG2025011064000020.jpg60170

[0073] Subscript 7, 11 and 12 in the above formulas 1 and Sub 2 is the same as defined in structural formula A9. For example, Sub in the above chemical formulas 7, 11 and 12 1 and Sub 2 The carbazole group containing the formula (8) is any one of the formulas A20 to A38. 1 and Sub 2 is the same as defined in structural formula A8. 1 and Sub 2 is the same as defined in structural formula A6. 1 and Sub 2 is the same as defined in structural formula A10. For example, Sub 1 and Sub 2The acridine group containing the formula is any one of structural formulas A39 to A45.

[0074] In the above Chemical Formulas 7 to 10, R 17 and R 18 is the same as defined in Formula 2. For example, R 17 ~R 18 The triazine group containing R is any one of the above structural formulas B1 to B27. 17 ~R 18 The triazine group containing R is represented by the above-mentioned structural formulas B12 and B50 to B54. 19 is the same as defined in Formula 3. As another example, R 19 The triazine group containing the following formula is any one of the structural formulas B28 to B49.

[0075] In the above Chemical Formulas 7 to 12, R 22 ~R 45 are each independently R defined in formula 1 5 ~R 8 Specifically, R 22 ~R 45 are independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted C4-C6 aryl group, or a substituted or unsubstituted C1-C3 alkyl group. Here, the substituted C1-C3 alkyl group is a C1-C3 alkyl group substituted with a halogen, and the halogen group can be F. For example, in the above chemical formulas 7 to 10, R 22 ~R 25 are, independently of each other, hydrogen or deuterium.

[0076] In the above formula 10, R 11 and R 12 are each independently hydrogen, deuterium, or a substituted or unsubstituted C1-C2 alkyl group.

[0077] By appropriately introducing electron-donating and electron-withdrawing groups, thermally activated delayed fluorescent substances can emit red, green, and blue light, and the difference between the singlet energy and the triplet energy can be reduced to 0.3 eV or less.

[0078] Specific examples of such thermally activated delayed fluorescent substances are shown in the following compounds 1 to 122, but are not limited thereto.

[0079] JPEG2025011064000021.jpg255164JPEG2025011064000022.jpg255157JPEG2025011064000023.jpg255148JPEG2025011064000024.jpg255154 JPEG2025011064000025.jpg255148JPEG2025011064000026.jpg147170JPEG2025011064000027.jpg137170JPEG2025011064000028.jpg211170

[0080] Compounds 1 to 21, 31 to 45, 52, 53, 55 to 60, 67 to 74, 81 to 86, and 93 to 122 are examples of compounds represented by chemical formula 7, compounds 22 to 30, 46 to 48, 75 to 78, and 89 to 92 are examples of compounds represented by chemical formula 8, compounds 49, 50, 61 to 66, 87, and 88 are examples of compounds represented by chemical formula 9, compounds 51, 54, 79, and 80 are examples of compounds represented by chemical formula 10, compounds 67 to 74 are examples of compounds represented by chemical formula 11, and compounds 83 to 86 are examples of compounds represented by chemical formula 12.

[0081] Explanation of Figure 3 3 is a schematic cross-sectional view of a light emitting device 10 according to an embodiment of the present invention. The light emitting device 10 includes a first electrode 110, an intermediate layer 130, and a second electrode 150.

[0082] Hereinafter, a structure and a method for manufacturing the light emitting device 10 according to an embodiment of the present invention will be described with reference to FIG.

[0083] 1st electrode 110 A substrate may be further disposed under the first electrode 110 or over the second electrode 150 in Fig. 3. The substrate may be a glass substrate or a plastic substrate. The substrate is a flexible substrate and 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.

[0084] The first electrode 110 is formed by providing a first electrode material on the substrate using, for example, a deposition method or a sputtering method. When the first electrode 110 is an anode, a high work function material that easily injects holes may be used as the first electrode material.

[0085] The first electrode 110 may be a reflective electrode, a semi-transparent electrode, or a transparent electrode. To form the first electrode 110 as a transparent electrode, the first electrode material may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), or any combination thereof can be used. Alternatively, to form the first electrode 110, which is a semi-transmissive electrode or a reflective electrode, the first electrode material can be magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0086] The first electrode 110 may have a single-layer structure or a multi-layer structure including a plurality of layers, for example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.

[0087] Middle layer 130 An intermediate layer 130 may be disposed on the first electrode 110. The intermediate layer 130 includes a light emitting layer.

[0088] The intermediate layer 130 may further include a hole transport region disposed between the first electrode 110 and the light emitting layer, and an electron transport region disposed between the light emitting layer and the second electrode 150.

[0089] The intermediate layer 130 may further include a metal-containing compound such as an organometallic compound, an inorganic material such as quantum dots, and the like, in addition to various organic materials.

[0090] Meanwhile, the intermediate layer 130 may include i) two or more emitting units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) at least one charge generation layer disposed between the two emitting units. When the intermediate layer 130 includes the above-mentioned two or more emitting units and at least one charge generation layer, the light emitting device 10 may be a tandem light emitting device.

[0091] Hole transport region in intermediate layer 130 The hole transport region can have i) a monolayer structure consisting of a single layer of a single material, ii) a monolayer structure consisting of a single layer containing a plurality of different materials, or iii) a multilayer structure including a plurality of layers containing a plurality of different materials.

[0092] The hole transport region may include a hole injection layer, a hole transport layer, a light-emitting assisting layer, an electron blocking layer, or any combination thereof.

[0093] For example, the hole transport region may have a multilayer structure of a hole injection layer / hole transport layer, a hole injection layer / hole transport layer / light emitting auxiliary layer, a hole injection layer / light emitting auxiliary layer, a hole transport layer / light emitting auxiliary layer, or a hole injection layer / hole transport layer / electron blocking layer, which are stacked in this order from the first electrode 110, but the structure of the hole transport region is not limited thereto.

[0094] The hole transport region may include a compound represented by formula 201, a compound represented by formula 202, or any combination thereof:

[0095] [Chemical formula 201] JPEG2025011064000029.jpg29170

[0096] [Chemical formula 202] JPEG2025011064000030.jpg36170

[0097] In the above chemical formulas 201 and 202, L 201 ~L 204 are, independently of each other, at least one R 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 60 is a heterocyclic group, L 205 *-O-*', *-S-*', *-N(Q 201 )-*', at least one R 10a Substituted or unsubstituted C 1 -C 20 an alkylene group, at least one R 10a Substituted or unsubstituted C 2 -C 20 alkenylene group, at least one R 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group or at least one R 10aSubstituted or unsubstituted C 1 -C 60 is a heterocyclic group, xa1 to xa4 are each independently an integer of 0 to 5; xa5 is an integer from 1 to 10, R 201 ~R 204 and Q 201 are, independently of each other, at least one R 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 60 is a heterocyclic group, R 201 and R 202 is optionally a single bond, at least one R 10a Substituted or unsubstituted C 1 -C 5 an alkylene group, or at least one R 10a Substituted or unsubstituted C 2 -C 5 are linked together via an alkenylene group, and at least one R 10a Substituted or unsubstituted C 8 -C 60 Polycyclic groups (such as carbazole groups) can be formed (see, for example, compound HT16 below), R 203 and R 204 is optionally a single bond, at least one R 10a Substituted or unsubstituted C 1 -C 5 an alkylene group, or at least one R 10a Substituted or unsubstituted C 2 -C 5 are linked together via an alkenylene group, and at least one R 10a Substituted or unsubstituted C 8 -C 60 can form polycyclic groups, na1 is an integer from 1 to 4.

[0098] For example, each of the chemical formulas 201 and 202 may include at least one of the groups represented by the following chemical formulas CY201 to CY217:

[0099] JPEG2025011064000031.jpg97170

[0100] In the above chemical formulas CY201 to CY217, R 10b and R 10c The explanations regarding R in this specification are as follows. 10a Please refer to the explanation of the CY 201 ~Kan CY 204 are independent of each other, C 3 -C 20 Carbocyclic group or C 1 -C 20 In the formulae CY201 to CY217, at least one hydrogen is selected from the group consisting of R 10a It may be substituted or unsubstituted with.

[0101] According to one embodiment, in the formulae CY201 to CY217, the ring CY 201 ~Kan CY 204 may be, independently of each other, a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.

[0102] According to another embodiment, each of the compound represented by the chemical formula 201 and the compound represented by the chemical formula 202 may contain at least one of the groups represented by the chemical formulas CY201 to CY203.

[0103] According to yet another embodiment, the compound represented by the chemical formula 201 may include at least one of the groups represented by the chemical formulas CY201 to CY203 and at least one of the groups represented by the chemical formulas CY204 to CY217.

[0104] According to yet another embodiment, in the formula 201, xa1 is 1 and R 201is a group represented by one of the chemical formulas CY201 to CY203, xa2 is 0, and R 202 may be a group represented by one of the above chemical formulas CY204 to CY207.

[0105] According to still another embodiment, each of the compound represented by the chemical formula 201 and the compound represented by the chemical formula 202 may not contain any of the groups represented by the chemical formulas CY201 to CY203.

[0106] According to yet another embodiment, each of the compound represented by chemical formula 201 and the compound represented by chemical formula 202 may not contain any of the groups represented by chemical formulas CY201 to CY203, but may contain at least one of the groups represented by chemical formulas CY204 to CY217.

[0107] As yet another example, each of the compound represented by the chemical formula 201 and the compound represented by the chemical formula 202 may not contain any of the groups represented by the chemical formulas CY201 to CY217.

[0108] For example, the hole transport region may include one of the following compounds HT1-HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), or any combination thereof:

[0109] JPEG2025011064000032.jpg184170JPEG2025011064000033.jpg189170JPEG2025011064000034.jpg218170JPEG2025011064000035.jpg255170

[0110] The thickness of the hole transport region is about 50 Å to about 10,000 Å, for example, about 100 Å to about 4,000 Å. 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 is about 100 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, and the thickness of the hole transport layer is about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the above-mentioned ranges, the required hole transport characteristics can be obtained without a substantial increase in driving voltage.

[0111] The light emitting auxiliary layer compensates for the optical resonance distance according to the wavelength of light emitted from the light emitting layer to increase light emission efficiency. The electron blocking layer prevents electron leakage from the light emitting layer to the hole transport region. The materials contained in the hole transport region are also contained in the light emitting auxiliary layer and the electron blocking layer.

[0112] p-type dopants In addition to the materials described above, the hole transport region may include a charge generating material to enhance conductivity. The charge generating material may be uniformly or non-uniformly dispersed (e.g., in the form of a single layer of the charge generating material) within the hole transport region.

[0113] The charge generating material can be, for example, a p-type dopant.

[0114] For example, the LUMO energy level of the p-type dopant can be about -3.5 eV or less.

[0115] According to one embodiment, the p-type dopant may include a quinone derivative, a cyano group-containing compound, an element EL1 and an element EL2-containing compound, or any combination thereof.

[0116] Examples of said quinone derivatives may include TCNQ, F4-TCNQ, and the like.

[0117] Examples of the cyano group-containing compound include HAT-CN, a compound represented by the following formula 221, and the like.

[0118] JPEG2025011064000036.jpg48170

[0119] [Chemical formula 221] JPEG2025011064000037.jpg37170

[0120] In the above formula 221, R 221 ~R 223 are, independently of each other, at least one R 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 60 is a heterocyclic group, R 221 ~R 223 at least one of the groups is independently selected from the group consisting of a cyano group, -F, -Cl, -Br, -I, a C substituted with a cyano group, -F, -Cl, -Br, -I, or any combination thereof; 1 -C 20 or any combination thereof; 3 -C 60 Carbocyclic group or C 1 -C 60 It can be a heterocyclic group.

[0121] In the compound containing the elements EL1 and EL2, the element EL1 is a metal, a metalloid, or a combination thereof, and the element EL2 is a nonmetal, a metalloid, or a combination thereof.

[0122] Examples of the metal 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 (Cs), etc.). (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.; post-transition metals (e.g., zinc (Zn), indium (In), tin (Sn), etc.); lanthanide metals (e.g., lanthanum (La), 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), ruthenium (Lu), etc.); and the like.

[0123] Examples of the metalloid may include silicon (Si), antimony (Sb), tellurium (Te), and the like.

[0124] Examples of said non-metals may include oxygen (O), halogens (eg, F, Cl, Br, I, etc.), and the like.

[0125] For example, the compound containing element EL1 and element EL2 may include a metal oxide, a metal halide (e.g., a metal fluoride, a metal chloride, a metal bromide, a metal iodide, etc.), a metalloid halide (e.g., a metalloid fluoride, a metalloid chloride, a metalloid bromide, a metalloid iodide, etc.), a metal telluride, or any combination thereof.

[0126] Examples of the metal oxide include tungsten oxide (e.g., WO, W 2 O 3 , WO 2 , WO 3 , W 2 O 5 ), vanadium oxides (e.g., VO, V 2 O 3 , V.O. 2 , V 2 O 5 etc.), molybdenum oxide (MoO, Mo 2 O 3 , MoO 2 , MoO 3 , Mo 2 O 5 ), rhenium oxides (e.g., ReO 3 etc.) may also be included.

[0127] Examples of said metal halides may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, lanthanide metal halides, and the like.

[0128] Examples of the alkali metal halides may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, and the like.

[0129] An example of the alkaline earth metal halide is BeF 2 , MgF 2 , CaF 2 , SrF 2 , BaF 2 , BeCl 2 , MgCl2 , CaCl 2 , SrCl 2 , BaCl 2 , BeBr 2 , MgBr 2 , CaBr 2 , SrBr 2 , BaBr 2 , BeI 2 , MgI 2 , CaI 2 , SrI 2 ,BaI 2 etc. may be included.

[0130] Examples of the transition metal halide include titanium halides (e.g., TiF 4 , TiCl 4 , TiBr 4 , TiI 4 etc.), zirconium halides (e.g., ZrF 4 , ZrCl 4 , ZrBr 4 , ZrI 4 etc.), hafnium halides (e.g., HfF 4 , HfCl 4 , HfBr 4 , HfI 4 ), vanadium halides (e.g., VF 3 , VCl 3 , VBr 3 , V.I. 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), tungsten halides (e.g., WF 3 , WCl 3 , W.B.R. 3 , W.I. 3 etc.), manganese halides (e.g., MnF 2 , MnCl 2 , MnBr 2 , MnI 2 ), 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.), iron halides (e.g., FeF 2 , FeCl 2 , FeBr 2 , FeI 2 etc.), ruthenium halides (e.g., RuF 2 , RuCl 2 , RuBr 2 , RuI 2 ), 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., PdF2 , PdCl 2 , PdBr 2 , PdI 2 etc.), platinum halides (e.g., PtF 2 , PtCl 2 , PtBr 2 , PtI 2 etc.), copper halides (e.g., CuF, CuCl, CuBr, CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.), gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.), and the like.

[0131] Examples of the post-transition metal halide include zinc halides (e.g., ZnF 2 , ZnCl 2 , ZnBr 2 , ZnI 2 etc.), indium halides (e.g., InI 3 etc.), tin halides (e.g., SnI 2 etc.) may also be included.

[0132] Examples of the lanthanide metal halides are 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 3 , SmI 3 etc. may be included.

[0133] Examples of the metalloid halides include antimony halides (e.g., SbCl 5 etc.) may also be included.

[0134] Examples of the metal tellurides include alkali metal tellurides (e.g., Li 2 Te, Na 2 Te, K 2 Te, Rb2 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 , Ta 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.), post-transition metal tellurides (e.g., ZnTe, etc.), lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.), and the like.

[0135] Light-emitting layer in intermediate layer 130 When the light emitting device 10 is a full-color light emitting device, the light emitting layer is patterned into a red light emitting layer, a green light emitting layer, and / or a blue light emitting layer for each subpixel, or the light emitting layer may have a structure in which two or more layers selected from the red light emitting layer, the green light emitting layer, and the blue light emitting layer are stacked in contact with or spaced apart from each other, or may have a structure in which two or more materials selected from the red light emitting material, the green light emitting material, and the blue light emitting material are mixed without layer division, and may emit white light.

[0136] The light-emitting layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.

[0137] The content of the dopant in the light emitting layer may be about 0.01 to about 15 parts by weight based on 100 parts by weight of the host.

[0138] Alternatively, the light emitting layer may include quantum dots.

[0139] Meanwhile, the light emitting layer may include a delayed fluorescent material, which may act as a host or a dopant in the light emitting layer.

[0140] The thickness of the light emitting layer is about 100 Å to about 1000 Å, for example, about 200 Å to about 600 Å. When the thickness of the light emitting layer satisfies the above range, excellent light emitting characteristics can be exhibited without a substantial increase in driving voltage.

[0141] host The host may include a compound represented by formula 301: [Chemical formula 301] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21

[0142] In the above formula 301, Ar 301 and L 301 are, independently of each other, at least one R 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 60 is a heterocyclic group, xb11 is 1, 2 or 3; xb1 is an integer from 0 to 5, R 301 is hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, or at least one R 10a Substituted or unsubstituted C 1 -C60 Alkyl group, at least one R 10a Substituted or unsubstituted C 2 -C 60 alkenyl group, at least one R 10a Substituted or unsubstituted C 2 -C 60 Alkynyl group, at least one R 10a Substituted or unsubstituted C 1 -C 60 Alkoxy group, at least one R 10a Substituted or unsubstituted C 3 -C 60 Carbocyclic group, at least one R 10a Substituted or unsubstituted 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 ) and xb21 is an integer from 1 to 5, Q 301 ~Q 303 The explanations regarding Q and Q in this specification are as follows. 1 Please refer to the explanation related to.

[0143] For example, in the above formula 301, when xb11 is 2 or more, 2 or more Ar 301 can be linked to each other via a single bond.

[0144] As another example, the host may include a compound represented by formula 301-1 below, a compound represented by formula 301-2 below, or any combination thereof:

[0145] [Chemical formula 301-1] JPEG2025011064000038.jpg32170

[0146] [Chemical formula 301-2] JPEG2025011064000039.jpg47170

[0147] In the above chemical formulas 301-1 and 301-2, Ring A 301 ~Ring A 304 are, independently of each other, at least one R 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 60 is a heterocyclic group, X 301 is O, S, N[(L 304 ) xb4 -R 304 ], C(R 304 )(R 305 ), or Si(R 304 )(R 305 ) and xb22 and xb23 are independently 0, 1 or 2; L 301 , xb1 and R 301 For the explanation of each of the above, please refer to the descriptions in this specification. L 302 ~L 304 The explanations regarding the above are independent of each other. 301 Refer to the explanation regarding For the explanation of xb2 to xb4, refer to the explanation of xb1. R 302 ~R 305 and R 311 ~R 314 For the explanation of 301 Please refer to the explanation related to.

[0148] As yet another example, the host may include an alkaline earth metal complex, a post-transition metal complex, or any combination thereof. For example, the host may include a Be complex (e.g., compound H55 below), a Mg complex, a Zn complex, or any combination thereof.

[0149] As yet another example, the host may include one of the following compounds H1-H128: 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), or any combination thereof:

[0150] JPEG2025011064000040.jpg251170JPEG2025011064000041.jpg232170JPEG2025011064000042.jpg244170 JPEG2025011064000043.jpg204170JPEG2025011064000044.jpg177170JPEG2025011064000045.jpg179170

[0151] Phosphorescent Dopants The phosphorescent dopant may include at least one transition metal as a central metal.

[0152] The phosphorescent dopant may include monodentate ligands, bidentate ligands, tridentate ligands, tetradentate ligands, pentadentate ligands, hexadentate ligands, or any combination thereof.

[0153] The phosphorescent dopant can be electrically neutral.

[0154] For example, the phosphorescent dopant may include an organometallic compound represented by Formula 401 or Formula 402:

[0155] [Chemical formula 401] M(L 401 ) xc1 (L 402 ) xc2

[0156] [Chemical formula 402] JPEG2025011064000046.jpg58170

[0157] In the above chemical formulas 401 and 402, M is 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)); L 401 is a ligand represented by the above chemical formula 402, xc1 is 1, 2 or 3, and when xc1 is 2 or more, 2 or more L 401 may be the same or different, L 402 is an organic ligand, xc2 is 0, 1, 2, 3, or 4, and if xc2 is 2 or more, then 2 or more L 402 may be the same or different, X 401 and X 402 are, independently of each other, nitrogen or carbon; Ring A 401 and Ring A 402 are independent of each other, C 3 -C 60 Carbocyclic group or C 1 -C 60 is a heterocyclic group, T 401 is 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=*', X 403 and X 404 are, independently of each other, a chemical bond (e.g., a covalent or coordinate bond), O, S, N(Q 413 ), B(Q 413 ), P(Q 413 ), C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ) and Q 411 ~Q 414 The explanations regarding Q and Q in this specification are as follows. 1 Refer to the explanation regarding R 401 and R 402 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, at least one R 10a Substituted or unsubstituted C 1 -C 20 Alkyl group, at least one R 10a Substituted or unsubstituted C 1 -C 20 Alkoxy group, at least one R 10a Substituted or unsubstituted C 3 -C 60 Carbocyclic group, at least one R 10a Substituted or unsubstituted 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 ) and Q 401 ~Q403 The explanations regarding Q and Q in this specification are as follows. 1 Refer to the explanation regarding xc11 and xc12 are each independently an integer of 0 to 10; In said chemical formula 402, * and *' are binding sites with M in said chemical formula 401, respectively.

[0158] For example, in the above formula 402, i) X 401 is nitrogen and X 402 is carbon, or ii) X 401 and X 402 Both are nitrogen.

[0159] As another example, in the above formula 401, when xc1 is 2 or more, L 401 Of these, two rings A 401 is optionally a linking group, T 402 or two rings A 402 is optionally a linking group, T 403 (See compounds PD1 to PD4 and PD7 below.) 402 and T 403 The explanations regarding the above are given in the T 401 Please refer to the explanation related to.

[0160] In the above formula 401, L 402 can be any organic ligand. For example, 402 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 group (e.g., a phosphine group, a phosphite group, etc.), or any combination thereof.

[0161] The phosphorescent dopant may include, for example, one of the following compounds PD1 to PD39, or any combination thereof:

[0162] JPEG2025011064000047.jpg160170JPEG2025011064000048.jpg218170JPEG2025011064000049.jpg56170

[0163] Fluorescent Dopants The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.

[0164] For example, the fluorescent dopant may include a compound represented by the following formula 501:

[0165] [Chemical formula 501] JPEG2025011064000050.jpg32170

[0166] In the above formula 501, Ar 501 , L 501 ~L 503 , R 501 and R 502 are, independently of each other, at least one R 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 60 is a heterocyclic group, xd1 to xd3 are each independently 0, 1, 2, or 3; xd4 is 1, 2, 3, 4, 5 or 6.

[0167] For example, in the formula 501, Ar 501 may contain a fused ring group in which three or more monocyclic groups are fused together (eg, anthracene group, chrysene group, pyrene group, etc.).

[0168] As another example, in formula 501, xd4 can be 2.

[0169] For example, the fluorescent dopant may include one of the following compounds FD1-FD37, DPVBi, DPAVBi, or any combination thereof:

[0170] JPEG2025011064000051.jpg187170JPEG2025011064000052.jpg178170JPEG2025011064000053.jpg214170

[0171] Delayed fluorescent material The light-emitting layer may contain a delayed fluorescent material.

[0172] In the present specification, the delayed fluorescent substance may be selected from any compound capable of emitting delayed fluorescence through a delayed fluorescence emission mechanism.

[0173] The delayed fluorescent material included in the emission layer may act as a host or a dopant depending on the type of other material included in the emission layer.

[0174] According to one 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 is about 0 eV or more and about 0.5 eV or less. 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-mentioned range, reverse energy transfer (up-conversion) from the triplet state to the singlet state in the delayed fluorescent material is effectively performed, and the luminous efficiency of the light-emitting element 10 can be improved.

[0175] For example, the delayed fluorescent material may have at least one electron donor (e.g., a π-electron-rich C 3 -C 60 ring group, etc.), and at least one electron acceptor (e.g., sulfoxide group, cyano group, π-electron deficient nitrogen-containing C 1 -C 60 ii) substances containing two or more ring groups condensed while sharing boron (B),8 -C 60 It may also contain substances containing polycyclic groups.

[0176] Examples of the delayed fluorescent material may include at least one of the following compounds DF1 to DF14:

[0177] JPEG2025011064000054.jpg233170JPEG2025011064000055.jpg47170

[0178] Quantum dots The light emitting layer may include quantum dots.

[0179] As used herein, quantum dots refer to crystals of semiconductor compounds and include any material that can emit light of various emission wavelengths depending on the size of the crystals.

[0180] The quantum dots have a diameter of, for example, about 1 nm to about 10 nm.

[0181] The quantum dots may be synthesized by wet chemical processes, metalorganic chemical vapor deposition processes, molecular beam epitaxy processes, or the like.

[0182] The wet chemical process is a method of growing quantum dot particle crystals after mixing an organic solvent with a precursor material. When the crystals grow, the organic solvent naturally acts as a dispersant coordinated to the surface of the quantum dot crystals and controls the growth of the crystals, so the growth of the quantum dot particles can be controlled through a process that is easier and less expensive than gas phase deposition methods such as metal organic chemical vapor deposition (MOCVD) and molecular beam epitaxy (MBE).

[0183] The quantum dots may comprise a II-VI semiconductor compound; a III-V semiconductor compound; a III-VI semiconductor compound; a I-III-VI semiconductor compound; a IV-VI semiconductor compound; a Group IV element or compound; or any combination thereof.

[0184] Examples of the II-VI semiconductor compounds may include binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS; quaternary compounds such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, or any combination thereof.

[0185] Examples of the III-V semiconductor compounds may include binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, etc.; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb, etc.; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, etc.; or any combination thereof. Meanwhile, the III-V semiconductor compounds may further include a group II element. Examples of III-V semiconductor compounds further including a Group II element may include InZnP, InGaZnP, InAlZnP, and the like.

[0186] Examples of the III-VI group semiconductor compounds are GaS, GaSe, Ga 2 Se 3 , GaTe, InS, InSe, In 2 S 3 , In 2 Se 3 , InTe and other binary compounds; InGaS 3 , InGaSe 3 or any combination thereof.

[0187] Examples of the I-III-VI group semiconductor compounds include AgInS, AgInS 2 , CuInS, CuInS 2 ,CuGaO 2 , AgGaO 2 , AgAlO 2 or any combination thereof.

[0188] Examples of the IV-VI semiconductor compounds may include binary compounds such as SnS, SnSe, SnTe, PbS, PbSe, PbTe; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe; quaternary compounds such as SnPbSSe, SnPbSeTe, SnPbSTe; or any combination thereof.

[0189] The Group IV elements or compounds may include single elements such as Si, Ge; binary compounds such as SiC, SiGe; or any combination thereof.

[0190] Each element contained in the multi-element compounds, such as the binary, ternary and quaternary compounds, may be present in the particles at a uniform or non-uniform concentration.

[0191] Meanwhile, the quantum dots may have a single structure in which the concentration of each element contained in the quantum dot is uniform, or a core-shell double structure, in which, for example, the material contained in the core and the material contained in the shell are different from each other.

[0192] The shell of the quantum dot may act as a protective layer to prevent chemical denaturation of the core and maintain the semiconductor properties, and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell may be a single layer or multiple layers. The interface between the core and the shell may have a concentration gradient in which the concentration of elements present in the shell decreases toward the center.

[0193] Examples of the shell of the quantum dot include oxides of metals, semimetals or nonmetals, semiconductor compounds, or combinations thereof. Examples of the oxides of metals, semimetals or nonmetals include SiO 2 , Al 2 O 3 , TiO 2 , ZnO, MnO, Mn 2 O 3 , Mn 3 O 4 , CuO, FeO, Fe 2 O 3 , Fe 3 O 4 , CoO, Co 3 O 4 , NiO, and other binary compounds; MgAl 2 O 4 , CoFe 2 O 4 , NiFe 2 O 4 , CoMn 2 O 4 Examples of the 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, as described herein. For example, the semiconductor compounds may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaS, GaSe, AgGaS, AgGaS 2, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.

[0194] The quantum dots may have a full width of half maximum (FWHM) of an emission wavelength spectrum of about 45 nm or less, specifically about 40 nm or less, more specifically about 30 nm or less, and within this range, color purity and color reproducibility may be improved. In addition, since light emitted through such quantum dots is emitted in all directions, a wide viewing angle may be improved.

[0195] The quantum dots may be in the form of, for example, a spherical particle, a pyramidal particle, a multi-arm particle, a cubic nanoparticle, a nanotube particle, a nanowire particle, a nanofiber particle, or a nanoplate particle.

[0196] By adjusting the size of the quantum dots, the energy band gap can be adjusted, and light of various wavelength bands can be obtained from the quantum dot light emitting layer. Therefore, by using quantum dots of different sizes, a light emitting device that emits light of multiple wavelengths can be realized. Specifically, the size of the quantum dots can be selected to emit red light, green light, and / or blue light. In addition, the size of the quantum dots can be configured to combine lights of various colors to emit white light.

[0197] Electron transport region in intermediate layer 130 The electron transport region can have i) a monolayer structure consisting of a single layer of a single material, ii) a monolayer structure consisting of a single layer containing multiple different materials, or iii) a multilayer structure including multiple layers containing multiple different materials.

[0198] The electron transport region may include a buffer layer, a hole blocking layer, an electron modulating layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0199] For example, the electron transport region may have a structure such as an electron transport layer / electron injection layer, a hole blocking layer / electron transport layer / electron injection layer, an electron control layer / electron transport layer / electron injection layer, or a buffer layer / electron transport layer / electron injection layer, which are stacked in this order from the light emitting layer.

[0200] The electron transport region (e.g., a buffer layer, a hole blocking layer, an electron modulating layer, or an electron transport layer in the electron transport region) is preferably made of at least one π-electron deficient nitrogen-containing C 1 -C 60 Metal-free compounds containing ring groups may also be included.

[0201] For example, the electron transport region may include a compound represented by formula 601 below. [Chemical formula 601] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21

[0202] In the above formula 601, Ar 601 and L 601 are, independently of each other, at least one R 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 60 is a heterocyclic group, xe11 is 1, 2 or 3, xe1 is 0, 1, 2, 3, 4 or 5, R 601 At least one R 10a Substituted or unsubstituted C 3 -C 60 Carbocyclic group, at least one R 10a Substituted or unsubstituted 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 ) and Q 601 ~Q 603 The explanations regarding Q and Q in this specification are as follows. 1 Refer to the explanation regarding xe21 is 1, 2, 3, 4 or 5, The Ar 601 , L 601 and R 601 At least one of the 10a Substituted or unsubstituted π-electron deficient nitrogen-containing C 1 -C 60 It can be a cyclic group.

[0203] For example, in the above formula 601, when xe11 is 2 or more, 2 or more Ar 601 can be linked to each other via a single bond.

[0204] As another example, in the formula 601, Ar 601 At least one R 10a The anthracene group may be a substituted or unsubstituted anthracene group.

[0205] As yet another example, the electron transport region may include a compound represented by formula 601-1:

[0206] [Chemical formula 601-1] JPEG2025011064000056.jpg33170

[0207] In the above chemical formula 601-1, X 614 is N or C(R 614 ) and X 615 is N or C(R 615 ) and X 616 is N or C(R 616) and X 614 ~X 616 At least one of is N, L 611 ~L 613 The explanations regarding the above are given in L 601 Refer to the explanation regarding For the explanation of xe611 to xe613, please refer to the explanation of xe1. R 611 ~R 613 For the explanation of 601 Refer to the explanation regarding R 614 ~R 616 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, at least one R 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 60 It can be a heterocyclic group.

[0208] For example, in the chemical formulae 601 and 601-1, xe1 and xe611 to xe613 are each independently 0, 1 or 2.

[0209] The electron transport region may be one of the following 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, NTAZ, or any combination thereof:

[0210] JPEG2025011064000057.jpg184170JPEG2025011064000058.jpg250170JPEG2025011064000059.jpg97170

[0211] The thickness of the electron transport region is about 100 Å to about 5000 Å, for example, about 160 Å to about 4000 Å. When the electron transport region includes a buffer layer, a hole blocking layer, an electron adjusting layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron adjusting layer is, independently of one another, about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å, and the thickness of the electron transport layer is about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the buffer layer, the hole blocking layer, the electron adjusting layer, the electron transport layer, and / or the electron transport region satisfies the above-mentioned range, the required electron transport properties can be obtained without a substantial increase in the driving voltage.

[0212] The electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material in addition to the materials described above.

[0213] 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 a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and the metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion.

[0214] The ligands coordinated to the metal ions of the alkali metal complexes and alkaline earth metal complexes may, independently of one another, comprise hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

[0215] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, the following compounds ET-D1 (LiQ) or ET-D2:

[0216] JPEG2025011064000060.jpg42170

[0217] The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 150. The electron injection layer may be in direct contact with the second electrode 150.

[0218] The electron injection layer may have i) a single layer structure consisting of a single layer made of a single material, ii) a single layer structure consisting of a single layer containing a plurality of different materials, or iii) a multilayer structure having a plurality of layers containing a plurality of different materials.

[0219] The electron injection layer may comprise 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.

[0220] The alkali metals may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metals may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metals may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.

[0221] The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may include oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), tellurides, or any combination thereof, of the alkali metals, the alkaline earth metals, and the rare earth metals, respectively.

[0222] The alkali metal-containing compound is Li 2 O, Cs 2 OK2 It may contain alkali metal oxides such as O, alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, or any combination thereof. The alkaline earth metal-containing compound is BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying 0 < x < 1), Ba x Ca 1-x O (where x is a real number satisfying 0 < x < 1), etc. The rare earth metal-containing compound may contain 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 3 Or any combination thereof. Alternatively, the rare earth metal-containing compound may contain lanthanide metal tellurides. Examples of the lanthanide metal tellurides are LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La 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 2Te 3 , Yb 2 Te 3 , Lu 2 Te 3 etc. may be included.

[0223] The alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may include i) one of an alkali metal, alkaline earth metal, and rare earth metal ion as described above, and ii) a ligand bound to the metal ion, such as hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

[0224] The electron injection layer may consist solely 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, or may further contain an organic material (e.g., a compound represented by chemical formula 601).

[0225] According to one embodiment, the electron injection layer is composed of i) an alkali metal-containing compound (e.g., an alkali metal halide) or ii) a) an alkali metal-containing compound (e.g., an alkali metal halide) and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, the electron injection layer is a co-deposited KI:Yb layer, a co-deposited RbI:Yb layer, a co-deposited LiF:Yb layer, etc.

[0226] When the electron injection layer further comprises an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkaline earth metal-containing compound, rare earth metal-containing compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof is uniformly or non-uniformly dispersed in a matrix comprising the organic material.

[0227] The thickness of the electron injection layer is about 1 Å to about 100 Å, or about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the above-mentioned range, the required electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0228] 2nd electrode 150 The second electrode 150 may be disposed on the intermediate layer 130. The second electrode 150 may be a cathode, which is an electron injection electrode. In this case, the material for the second electrode 150 may be a metal, an alloy, an electrically conductive compound, or any combination thereof, each having a low work function.

[0229] 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.

[0230] The second electrode 150 may have a single-layer structure having a single layer, or a multi-layer structure having a plurality of layers.

[0231] Capping Layer A first capping layer is disposed on the outer side of the first electrode 110, and / or a second capping layer is disposed on the outer side of the second electrode 150. Specifically, 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 this 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 this 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 this order.

[0232] Light generated in the light-emitting layer in the intermediate layer 130 of the light-emitting element 10 is extracted to the outside through the first electrode 110, which is a semi-transparent electrode or a transparent electrode, and the first capping layer, and light generated in the light-emitting layer in the intermediate layer 130 of the light-emitting element 10 is extracted to the outside through the second electrode 150, which is a semi-transparent electrode or a transparent electrode, and the second capping layer.

[0233] The first and second capping layers may improve external light emitting efficiency according to the principle of constructive interference, thereby improving the light extraction efficiency of the light emitting device 10 and the light emitting efficiency of the light emitting device 10.

[0234] Each of the first and second capping layers may include a material having a refractive index (at 589 nm) of 1.6 or greater.

[0235] The first and second capping layers may be, independently of each other, an organic capping layer containing an organic material, an inorganic capping layer containing an inorganic material, or an organic-inorganic composite capping layer containing an organic material and an inorganic material.

[0236] At least one of the first and second capping layers may independently comprise a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound are optionally substituted with a substituent group including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof.

[0237] According to one embodiment, at least one of the first capping layer and the second capping layer may, independently of each other, comprise an amine group-containing compound.

[0238] For example, at least one of the first capping layer and the second capping layer may, independently of each other, comprise a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.

[0239] According to yet another embodiment, at least one of the first and second capping layers may comprise, independently of each other, one of the compounds HT28-HT33, one of the compounds CP1-CP6 below, β-NPB, or any compound thereof:

[0240] JPEG2025011064000061.jpg134170

[0241] film The amine-containing compound represented by Chemical Formula 1 is also included in various films. Thus, according to another aspect, there is provided a film containing the amine-containing compound represented by Chemical Formula 1. The film is, for example, an optical member (or light control means) (e.g., a color filter, a color conversion member, a capping layer, a light extraction efficiency improving layer, a selective light absorption layer, a polarizing layer, a quantum dot-containing layer, etc.), a light-shielding member (e.g., a light reflection layer, a light absorption layer, etc.), a protective member (e.g., an insulating layer, a dielectric layer, etc.), etc.

[0242] electronic equipment The light-emitting element is also included in various electronic devices, such as a light-emitting device and an authentication device.

[0243] The electronic device (e.g., light-emitting device) may further include i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer in addition to the light-emitting element. The color filter and / or the color conversion layer may be disposed in at least one traveling direction of light emitted from the light-emitting element. For example, the light emitted from the light-emitting element may be blue light or white light. For the description of the light-emitting element, please refer to the above. According to one embodiment, the color conversion layer may include quantum dots. The quantum dots are, for example, quantum dots as described herein.

[0244] The electronic device includes a first substrate, the first substrate including a plurality of sub-pixel regions, the color filter including a plurality of color filter regions corresponding to the plurality of sub-pixel regions, and the color conversion layer including a plurality of color conversion regions corresponding to the plurality of sub-pixel regions.

[0245] A pixel defining layer is disposed between the plurality of sub-pixel regions to define each of the sub-pixel regions.

[0246] The color filter may further include a plurality of color filter regions and a light-shielding pattern arranged between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light-shielding pattern arranged between the plurality of color conversion regions.

[0247] The color filter regions (or the color conversion regions) include a first region that emits a first color light, a second region that emits a second color light, and / or a third region that emits a third color light, and the first color light, the second color light, and / or the third color light may have different maximum emission wavelengths. For example, the first color light is red light, the second color light is green light, and the third color light is blue light. For example, the color filter regions (or the color conversion regions) may include quantum dots. Specifically, the first region includes red quantum dots, the second region includes green quantum dots, and the third region does not include quantum dots. For the description of quantum dots, please refer to the description in this specification. The first region, the second region, and / or the third region may further include a scatterer.

[0248] For example, the light emitting element may emit a first light, the first region may absorb the first light and emit a 1-1 color light, the second region may absorb the first light and emit a 2-1 color light, and the third region may absorb the first light and emit a 3-1 color light. In this case, the 1-1 color light, the 2-1 color light, and the 3-1 color light may have different maximum emission wavelengths. Specifically, the first light is blue light, the 1-1 color light is red light, the 2-1 color light is green light, and the 3-1 color light is blue light.

[0249] The electronic device may further include a thin film transistor in addition to the light emitting element as described above. The thin film transistor may include a source electrode, a drain electrode, and an active layer, and 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 element.

[0250] The thin film transistor may further include a gate electrode and a gate insulating film.

[0251] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, or the like.

[0252] The electronic device may further include a sealing part for sealing the light emitting element. The sealing part is disposed between the color filter and / or color conversion layer and the light emitting element. The sealing part allows light from the light emitting element to be extracted to the outside while simultaneously blocking the penetration of outside air and moisture into the light emitting element. The sealing part may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing part may be a thin film sealing layer including one or more organic layers and / or inorganic layers. When the sealing part is a thin film sealing layer, the electronic device is flexible.

[0253] In addition to the color filter and / or color conversion layer, various functional layers may be further disposed on the sealing part depending on the application of the electronic device. Examples of the functional layer may include a touch screen layer, a polarizing layer, etc. The touch screen layer is a decompression type touch screen layer, an electrostatic type touch screen layer, or an infrared type touch screen layer. The authentication device is, for example, a biometric authentication device that authenticates an individual using biometric information (e.g., fingertip, pupil, etc.).

[0254] The authentication device may further include a biometric information collecting means in addition to the light emitting element as described above.

[0255] The electronic devices can be applied to various displays, light sources, lighting, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game consoles, medical equipment (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram display devices, ultrasonic diagnostic devices, and endoscopic display devices), fish finders, various measuring instruments, gauges (e.g., gauges for vehicles, aircraft, and ships), projectors, and the like.

[0256] electronic equipment The light emitting device is also included in various electronic devices.

[0257] For example, the electronic device including the light emitting element may be one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, an advertising board, indoor or outdoor lighting and / or signaling lights, 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 telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a 3D display, a virtual reality or augmented reality display, a vehicle, a video wall including tiled multiple displays, a theater or stadium screen, a phototherapy device, and a sign.

[0258] Since the light emitting device has excellent light emitting efficiency and long life, the electronic device including the light emitting device can have characteristics such as high brightness, high resolution, and low power consumption.

[0259] Description of Figures 4 and 5 FIG. 4 is a cross-sectional view of a light emitting device according to one embodiment of the present invention.

[0260] The light emitting device of FIG. 4 includes a substrate 100, a thin film transistor (TFT), a light emitting element, and an encapsulant 300 that seals the light emitting element.

[0261] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be disposed on the substrate 100. The buffer layer 210 may serve to prevent impurities from penetrating through the substrate 100 and provide a flat surface on the upper surface of the substrate 100.

[0262] A thin film transistor (TFT) may be disposed on the buffer layer 210. The thin film transistor (TFT) includes an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.

[0263] The active layer 220 may comprise an inorganic semiconductor, such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and includes a source region, a drain region, and a channel region.

[0264] A gate insulating layer 230 for insulating the active layer 220 from a gate electrode 240 may be disposed on the active layer 220 , and a gate electrode 240 may be disposed on the gate insulating layer 230 .

[0265] An interlayer insulating layer 250 may be disposed on the gate electrode 240. The interlayer insulating layer 250 is disposed between the gate electrode 240 and the source electrode 260, and between the gate electrode 240 and the drain electrode 270, and serves to insulate them.

[0266] A source electrode 260 and a drain electrode 270 may be disposed on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose a source region and a drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may be disposed to contact the exposed source region and the drain region of the active layer 220.

[0267] The thin film transistor (TFT) is electrically connected to the light emitting element to drive the light emitting element, and is covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. A light emitting element is provided on the passivation layer 280. The light emitting element includes a first electrode 110, an intermediate layer 130, and a second electrode 150.

[0268] The first electrode 110 may be disposed on the passivation layer 280. The passivation layer 280 may be disposed to expose a predetermined area of ​​the drain electrode 270 without covering the entire drain electrode 270, and the first electrode 110 may be disposed to be connected to the exposed drain electrode 270.

[0269] A pixel defining layer 290 including an insulating material may be disposed on the first electrode 110. The pixel defining layer 290 exposes a predetermined region of the first electrode 110, and the intermediate layer 130 may be formed on the exposed region. The pixel defining layer 290 may be a polyimide or polyacrylic organic film. Although not shown in FIG 4, some or more layers of the intermediate layer 130 may extend to an upper portion of the pixel defining layer 290 and be disposed in the form of a common layer.

[0270] A second electrode 150 may be disposed on the intermediate layer 130, and a capping layer 170 may be further formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.

[0271] An encapsulant 300 may be disposed on the capping layer 170. The encapsulant 300 is disposed on the light emitting device and serves to protect the light emitting device from moisture and oxygen. The encapsulant 300 may include an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof, an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), an epoxy resin (e.g., aliphatic glycidyl ether (AGE), etc.), or any combination thereof, or a combination of an inorganic film and an organic film.

[0272] FIG. 5 is a cross-sectional view of a light emitting device according to another embodiment of the present invention.

[0273] The light emitting device of Fig. 5 is similar to the light emitting device of Fig. 4, except that a light blocking pattern 500 and a functional region 400 are further disposed on the upper part of the encapsulation part 300. The functional region 400 may be i) a color filter region, ii) a color conversion region, or iii) a combination of a color filter region and a color conversion region. According to an embodiment, the light emitting device included in the light emitting device of Fig. 5 may be a tandem light emitting device.

[0274] Explanation of Figure 6 6 is a perspective view showing an electronic device 1 including a light emitting device according to an embodiment of the present invention. The electronic device 1 is a device for displaying moving images or still images, and may be a portable electronic device such as a mobile phone, a smartphone, a tablet PC (personal computer), a mobile communication terminal, an electronic organizer, an electronic book, a PMP (portable multimedia player), a navigation system, or an UMPC (Ultra Mobile PC), as well as a television, a laptop, a monitor, a billboard, or an Internet of Things (IoT), or may be a part thereof. The electronic device 1 may also be a wearable device such as a smart watch, a watch phone, a glasses-type display, or a head mounted display (HMD), or may be a part thereof. Of course, the present invention is not limited thereto. For example, the electronic device 1 may be an instrument panel, a center fascia of an automobile, a CID (Center Information Display) arranged on a dashboard, a room mirror display replacing a side mirror of an automobile, an entertainment display for a rear seat of an automobile or a display arranged on the back of a front seat, a head up display (HUD) installed in front of a vehicle or projected on a windshield, or a computer generated hologram augmented reality head up display (CGH AR HUD). For convenience of explanation, FIG. 6 shows a case where the electronic device 1 is a smartphone.

[0275] The electronic device 1 includes a display area DA and a non-display area NDA outside the display area DA. The display device can realize an image through an array of a plurality of pixels arranged two-dimensionally in the display area DA.

[0276] The non-display area NDA is an area that does not display an image and may entirely surround the display area DA. Drivers for providing electrical signals and power to display elements arranged in the display area DA may be arranged in the non-display area NDA. Pads, which are areas to which electronic elements, printed circuit boards, etc. can be electrically connected, may be arranged in the non-display area NDA.

[0277] The electronic device 1 has a length in the x-axis direction and a length in the y-axis direction that are different from each other. For example, as shown in FIG. 6, the length in the x-axis direction is shorter than the length in the y-axis direction. As another example, the length in the x-axis direction and the length in the y-axis direction are the same. As yet another example, the length in the x-axis direction is longer than the length in the y-axis direction.

[0278] Description of FIG. 7 and FIG. 8A to FIG. 8C FIG. 7 is a schematic diagram illustrating the exterior of a vehicle 1000 as an electronic device including a light emitting device according to an embodiment of the present invention.

[0279] 8A to 8C are diagrams illustrating the interior of a vehicle 1000 according to various embodiments of the present invention.

[0280] 7, 8A, 8B, and 8C, the vehicle 1000 refers to various devices that move objects such as humans, goods, or animals from an origin to a destination. The vehicle 1000 includes vehicles that run on roads or railroads, ships that travel on seas or rivers, and airplanes that fly in the blue sky by utilizing the action of the air.

[0281] The vehicle 1000 can travel on a road or a railroad track. The vehicle 1000 can move in a predetermined direction by rotating at least one wheel. For example, the vehicle 1000 includes a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a motor vehicle, a bicycle, and a train that travels on a railroad track.

[0282] The vehicle 1000 includes a body having an interior and exterior, and a chassis on which mechanical devices required for running are installed, which is the remaining part excluding the body. The exterior of the body includes a front panel, a bonnet, a roof panel, a rear panel, a trunk, and fillers provided at the boundaries between the doors. The chassis of the vehicle 1000 includes a power generation device, a power transmission device, a running device, a steering device, a braking device, a suspension device, a transmission, a fuel device, front and rear wheels, left and right wheels, etc.

[0283] The vehicle 1000 includes a side window glass 1100, a front window glass 1200, a side mirror 1300, a cluster 1400, a center fascia 1500, a passenger dashboard 1600, and a display device 2.

[0284] The side window glass 1100 and the front window glass 1200 are also separated by a filler disposed between the side window glass 1100 and the front window glass 1200 .

[0285] The side window glass 1100 may be installed on a side of the vehicle 1000. In one embodiment, the side window glass 1100 is installed on a door of the vehicle 1000. A plurality of side window glasses 1100 are provided and face each other. In one embodiment, the side window glass 1100 includes a first side window glass 1110 and a second side window glass 1120. In one embodiment, the first side window glass 1110 is disposed adjacent to the cluster 1400. The second side window glass 1120 is disposed adjacent to the passenger dashboard 1600.

[0286] In an embodiment, the side window glass 1100 may be spaced apart from each other in the x direction or the -x 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 direction or the -x direction. That is, a virtual line L connecting the side window glass 1100 extends in the x direction or the -x direction. For example, the virtual line L connecting the first side window glass 1110 and the second side window glass 1120 extends in the x direction or the -x direction.

[0287] The front windshield glass 1200 may be installed at the front of the vehicle 1000. The front windshield glass 1200 may be disposed between the side window glasses 1100 facing each other.

[0288] The side mirror 1300 can provide a field of view behind the vehicle 1000. The side mirror 1300 can be installed on the exterior of the vehicle body. In one embodiment, a plurality of side mirrors 1300 are provided. One of the plurality of side mirrors 1300 is disposed on the outer side of the first side window glass 1110. The other of the plurality of side mirrors 1300 is disposed on the outer side of the second side window glass 1120.

[0289] Cluster 1400 may be located in front of the steering wheel and may include a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge, a turn signal, a warning light, a seat belt warning light, an odometer, a odometer recorder, an automatic transmission selector lever indicator light, a door ajar warning light, an engine oil warning light, and / or a low fuel warning light.

[0290] The center fascia 1500 includes a control panel on which a plurality of buttons for adjusting the audio system, the air conditioning system, and the seat heaters are arranged. The center fascia 1500 is disposed on one side of the cluster 1400.

[0291] The passenger dashboard 1600 may be separated from the cluster 1400 by the center fascia 1500. In one embodiment, the cluster 1400 is disposed corresponding to the driver's seat (not shown), and the passenger dashboard 1600 is disposed corresponding to the passenger seat (not shown). In one embodiment, the cluster 1400 is adjacent to the first side window glass 1110, and the passenger dashboard 1600 is adjacent to the second side window glass 1120.

[0292] In one embodiment, the display device 2 includes a display panel 3, and the display panel 3 can display an image. The display device 2 can be disposed inside the vehicle 1000. In one embodiment, the display device 2 is disposed between opposing side window glasses 1100. The display device 2 is disposed in at least one of the cluster 1400, the center fascia 1500, and the passenger dashboard 1600.

[0293] The display device 2 includes an organic light emitting display, an inorganic light emitting display, a quantum dot display, etc. Hereinafter, an organic light emitting display including a light emitting element according to the present invention will be described as an example of the display device 2 according to an embodiment of the present invention, but various types of display devices as described above can be used in the embodiment of the present invention.

[0294] 8A, the display device 2 may be disposed on the center fascia 1500. In one embodiment, the display device 2 may display navigation information. In one embodiment, the display device 2 may display information related to audio, video, or vehicle settings.

[0295] 8B, the display device 2 may be disposed in a cluster 1400. In this case, the cluster 1400 may display driving information, etc., using the display device 2. That is, the cluster 1400 may be realized in a digital manner. The digital cluster 1400 may display vehicle information and driving information as images. For example, the needle and gauge of the tachometer and various warning light icons may be displayed by digital signals.

[0296] 8C , the display device 2 may be disposed on the passenger side dashboard 1600. The display device 2 may be embedded in the passenger side dashboard 1600 or may be located on the passenger side dashboard 1600. In one embodiment, the display device 2 disposed on the passenger side dashboard 1600 may display an image related to the information displayed on the cluster 1400 and / or the information displayed on the center fascia 1500. In another embodiment, the display device 2 disposed on the passenger side dashboard 1600 may display information different from the information displayed on the cluster 1400 and / or the information displayed on the center fascia 1500.

[0297] Manufacturing method Each layer included in the hole transport region, the light emitting layer, and the electron transport region may be formed in a predetermined region using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, ink jet printing, laser printing, and Laser Induced Thermal Imaging (LITI) method.

[0298] When each layer included in the hole transport region, the light emitting layer, and each layer included in the electron transport region are formed by vacuum deposition, the deposition conditions are, for example, a deposition temperature of about 100 to about 500° C., a deposition temperature of about 10 -8 ~about 10 -3 The degree of vacuum of torr and the deposition rate within the range of about 0.01 to about 100 Å / sec can be selected taking into consideration the material contained in the layer to be formed and the structure of the layer to be formed.

[0299] Definition of Terms In this specification, C 3 -C 60 The carbocyclic group means a ring group having 3 to 60 carbon atoms and consisting only of carbon atoms as ring-forming atoms, 1 -C 60 The heterocyclic group means a ring group having 1 to 60 carbon atoms and further containing a heteroatom as a ring-forming atom in addition to carbon. 3 -C 60 Carbocyclic groups and C 1 -C 60 Each heterocyclic group may be a monocyclic group consisting of one ring, or a polycyclic group in which two or more rings are fused together. 1 -C 60 The heterocyclic group has 3 to 61 ring atoms.

[0300] In the present specification, the ring group is 3 -C 60 Carbocyclic groups and C 1 -C 60 Any of the heterocyclic groups is included.

[0301] In this specification, π-electron excess C 3 -C 60 The cyclic group means a cyclic group having 3 to 60 carbon atoms that does not contain *-N=*' as a ring-forming moiety, and is a π-electron deficient nitrogen-containing C 1 -C 60 The cyclic group means a heterocyclic group having 1 to 60 carbon atoms containing *-N=*' as a ring-forming moiety.

[0302] for example, Said C 3 -C 60The carbocyclic group is i) a group T1, or ii) a fused ring group in which two or more groups T1 are fused to each other (e.g., a cyclopentadiene group, an adamantane group, a norbornane group, a benzene group, a pentalene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a perylene group, a pentaphene group, a heptalene group, a naphthacene group, a picene group, a hexacene group, a pentacene group, a rubicene group, a coronene group, an ovalene group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, an indenophenanthrene group, or an indenoanthracene group); Said C 1 -C 60The heterocyclic group is i) a group T2, ii) a fused ring group in which two or more groups T2 are fused to each other, or iii) a fused ring group in which one or more groups T2 and one or more groups T1 are fused to 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 naphthoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, group, 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, a benzothiazole group, a benzisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoxazole group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoxazole group, a pyrimidine group, a pyrazine group, a pyridine ... azadibenzosilole group, azadibenzothiophene group, azadibenzofuran group, etc.), The π-electron excess C 3 -C 60 The ring group is i) a group T1, ii) a fused ring group in which two or more groups T1 are fused to each other, iii) a group T3, iv) a fused ring group in which two or more groups T3 are fused to each other, or v) a fused ring group in which one or more groups T3 and one or more groups T1 are fused to each other (for example, the above-mentioned C 3 -C 60carbocyclic group, 1H-pyrrole group, silole group, borole group, 2H-pyrrole group, 3H-pyrrole group, thiophene group, furan group, indole group, benzoindole group, naphthoindole group, isoindole group, benzisoindole group, naphthoindole group, benzosilole group, benzothiophene group, benzofuran group, carbazole group, dibenzosilole group, dibenzothiophene group, dibenzofuran group, indenocarbazole group, indolocarbazole group, benzofurocarbazole group, benzothienocarbazole group, benzosilolocarbazole group, benzoindolocarbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthothiophene group, benzonaphthosilole group, benzofurodibenzofuran group, benzofurodibenzothiophene group, benzothienodibenzothiophene group, etc.); The π-electron-deficient nitrogen-containing C 1 -C 60 The ring group is i) a group T4, ii) a fused ring group in which two or more groups T4 are fused to each other, iii) a fused ring group in which one or more groups T4 and one or more groups T1 are fused to each other, iv) a fused ring group in which one or more groups T4 and one or more groups T3 are fused to each other, or v) a fused ring group in which one or more groups T4, one or more groups T1 and one or more groups T3 are fused to each other (e.g., 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, azadibenzofuran group, etc.); the group T1 is 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 a 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 benzene group; the group T2 is a furan group, a thiophene group, a 1H-pyrrole group, a silole group, a borole 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 azasilole 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 imidazolidine 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; the group T3 is a furan group, a thiophene group, a 1H-pyrrole group, a silole group, or a borole group; The group T4 is 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 azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group.

[0303] In this specification, the ring group, C 3 -C 60 carbocyclic group, C 1 -C 60 Heterocyclic groups, π-electron-rich C 3 -C 60 Ring group or π-electron deficient nitrogen-containing C1 -C 60 The term cyclic group may be a group fused to any cyclic group, a monovalent group, or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) depending on the structure of the chemical formula in which the term is used. For example, a "benzene group" is a benzo group, a phenyl group, a phenylene group, etc., which can be easily understood by a person skilled in the art based on the structure of the chemical formula containing the "benzene group".

[0304] For example, monovalent C 3 -C 60 Carbocyclic groups and monovalent C 1 -C 60 Examples of heterocyclic groups are C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 It may include heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups.

[0305] Divalent C 3 -C 60 Carbocyclic groups and divalent C 1 -C 60 Examples of heterocyclic groups are C 3 -C 10 Cycloalkylene group, C 1 -C 10 Heterocycloalkylene group, C 3 -C 10 Cycloalkenylene group, C 1 -C 10 Heterocycloalkenylene group, C 6 -C 60 Arylene group, C 1 -C 60 It may include heteroarylene groups, divalent non-aromatic fused polycyclic groups, and divalent non-aromatic fused heteropolycyclic groups.

[0306] In this specification, C 1 -C 60 The alkyl group means a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group.

[0307] In this specification, C 1 -C 60 The alkylene group is 1 -C 60 It means a divalent group having the same structure as an alkyl group.

[0308] In this specification, C 2 -C 60 The alkenyl group is C 2 -C 60 It means a monovalent hydrocarbon group containing one or more carbon-carbon double bonds in the middle or at the end of the alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, and a butenyl group.

[0309] In this specification, C 2 -C 60 The alkenylene group is 2 -C 60 It means a divalent group having the same structure as an alkenyl group.

[0310] In this specification, C 2 -C 60 The alkynyl group is C 2 -C 60It means a monovalent hydrocarbon group containing one or more carbon-carbon triple bonds in the middle or at the end of the alkyl group, and specific examples thereof include an ethynyl group, a propynyl group, and the like.

[0311] In this specification, C 2 -C 60 The alkynylene group is 2 -C 60 It means a divalent group having the same structure as an alkynyl group.

[0312] In this specification, C 1 -C 60 The alkoxy group is -OA. 101 (Here, A 101 is the above C 1 -C 60 Specific examples of the aryl group include methoxy, ethoxy, and isopropyloxy groups.

[0313] In this specification, C 3 -C 10 A cycloalkyl group means a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group.

[0314] In this specification, C 3 -C 10 The cycloalkylene group is 3 -C 10 It means a divalent group having the same structure as a cycloalkyl group.

[0315] In this specification, C 1 -C 10The heterocycloalkyl group means a monovalent ring group having 1 to 10 carbon atoms which further contains at least one heteroatom as a ring-forming atom in addition to carbon atoms, and specific examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group.

[0316] In this specification, C 1 -C 10 The heterocycloalkylene group is 1 -C 10 It means a divalent group having the same structure as a heterocycloalkyl group.

[0317] In this specification, C 3 -C 10 The cycloalkenyl group means a monovalent ring group having 3 to 10 carbon atoms and having at least one carbon-carbon double bond in the ring but not having aromaticity. Specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group.

[0318] In this specification, C 3 -C 10 The cycloalkenylene group is 3 -C 10 It means a divalent group having the same structure as a cycloalkenyl group.

[0319] In this specification, C 1 -C 10 The heterocycloalkenyl group is a monovalent ring group having 1 to 10 carbon atoms, which further contains at least one heteroatom as a ring-forming atom in addition to carbon atoms, and has at least one double bond in the ring. 1 -C 10 Specific examples of heterocycloalkenyl groups include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like.

[0320] In this specification, C 1 -C 10The heterocycloalkenylene group is 1 -C 10 It means a divalent group having the same structure as a heterocycloalkenyl group.

[0321] In this specification, C 6 -C 60 The aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Specific examples of the aryl group include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, and an ovalenyl group.

[0322] In this specification, C 6 -C 60 An arylene group refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms.

[0323] Said C 6 -C 60 Aryl groups and C 6 -C 60 When an arylene group contains two or more rings, said two or more rings are fused together.

[0324] In this specification, C 1 -C 60 The heteroaryl group means a monovalent group that contains at least one heteroatom as a ring-forming atom in addition to carbon atoms and has a heterocyclic aromatic system having 1 to 60 carbon atoms. 1 -C 60Specific examples of heteroaryl groups include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, and a naphthyridinyl group.

[0325] In this specification, C 1 -C 60 The heteroarylene group means a divalent group which contains at least one heteroatom as a ring-forming atom in addition to carbon atoms and has a heterocyclic aromatic system having 1 to 60 carbon atoms.

[0326] Said C 1 -C 60 Heteroaryl groups and C 1 -C 60 When a heteroarylene group contains more than one ring, the two or more rings are fused together.

[0327] In this specification, a monovalent non-aromatic condensed polycyclic group refers to a monovalent group (e.g., having 8 to 60 carbon atoms) in which two or more rings are condensed with each other, the ring atoms are only carbon, and the entire molecule has non-aromaticity. Specific examples of the monovalent non-aromatic condensed polycyclic group include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, an indenoanthracenyl group, and the like.

[0328] In this specification, a divalent non-aromatic condensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group described above.

[0329] As used herein, a monovalent non-aromatic condensed heteropolycyclic group refers to a monovalent group (e.g., having 1 to 60 carbon atoms) in which two or more rings are condensed with each other and which further contains at least one heteroatom as a ring-forming atom other than carbon atoms, and in which the entire molecule is non-aromatic. Specific examples of the monovalent non-aromatic hetero-condensed polycyclic group include a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphthoindolyl group, an isoindolyl group, a benzisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl 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, and a thiadiazolyl group. group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indenocarbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthosilolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, a benzothienodibenzothiophenyl group, and the like.

[0330] In this specification, a divalent non-aromatic condensed heteropolycyclic group means a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group described above.

[0331] In this specification, C 6 -C 60 The aryloxy group is -OA. 102 (Here, A 102 is the above C 6 -C 60aryl group).

[0332] In this specification, C 6 -C 60 The arylthio group is -SA 103 (Here, A 103 is the above C 6 -C 60 aryl group).

[0333] In this specification, C 7 -C 60 The arylalkyl group is -A 104 A 105 (Here, A 104 is C 1 -C 54 is an alkylene group, 105 is C 6 -C 59 aryl group).

[0334] In this specification, C 2 -C 60 The heteroarylalkyl group is -A 106 A 107 (Here, A 106 is C 1 -C 59 is an alkylene group, 107 is C 1 -C 59 Heteroaryl groups are shown.

[0335] As used herein, "R 10a "teeth, deuterium (-D), -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, or a nitro group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C 3 -C 60 carbocyclic group, C 1 -C 60 Heterocyclic groups, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60Arylalkyl groups, C 2 -C 60 Heteroarylalkyl groups, -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, substituted or unsubstituted, 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, or C 1 -C 60 Alkoxy groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 60 carbocyclic group, C 1 -C 60 Heterocyclic groups, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl groups, C 2 -C 60 Heteroarylalkyl groups, -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, substituted or unsubstituted, 3 -C 60 carbocyclic group, C 1 -C 60 Heterocyclic groups, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group, or C 2 -C 60 Heteroarylalkyl groups; or -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 ); may also be used.

[0336] In this specification, Q 1 ~Q 3 , Q 11 ~Q 13 , Q 21 ~Q 23 and Q 31 ~Q 33 are, independently of each other, hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; C 1 -C 60 Alkyl group; C 2 -C 60 Alkenyl group; C 2 -C 60 Alkynyl group; C 1 -C 60 Alkoxy group; or deuterium, -F, cyano group, C 1 -C 60 Alkyl group, C 1-C 60 C, substituted or unsubstituted with alkoxy groups, phenyl groups, biphenyl groups, or any combination thereof 3 -C 60 carbocyclic group, C 1 -C 60 Heterocyclic groups, C 7 -C 60 Arylalkyl group, or C 2 -C 60 It may be a heteroarylalkyl group.

[0337] As used herein, heteroatom refers to any atom other than a carbon atom. Examples of said heteroatoms include O, S, N, P, Si, B, Ge, Se, or any combination thereof.

[0338] As used herein, third row transition metals include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), and gold (Au), among others.

[0339] As used herein, "Ph" means a phenyl group, "Me" means a methyl group, "Et" means an ethyl group, and "tert-Bu" or "Bu t " means a tert-butyl group and "OMe" means a methoxy group.

[0340] In the present specification, the term "biphenyl group" means a "phenyl group substituted with a phenyl group". The "biphenyl group" is a group in which the substituent is "C 6 -C 60 It belongs to the "substituted phenyl group" which is an "aryl group."

[0341] In the present specification, the term "terphenyl group" means a "phenyl group substituted with a biphenyl group". The "terphenyl group" is a group in which the substituent is "C 6 -C 60 Aryl-substituted C 6 -C 60 It belongs to the "substituted phenyl group" which is an "aryl group."

[0342] In this specification, unless otherwise defined, * and *' refer to bond sites to adjacent atoms in the formula or moiety.

[0343] In this specification, the x-axis, y-axis, and z-axis are not limited to the three axes on a Cartesian coordinate system, but are also interpreted in a broad sense including the three axes. For example, the x-axis, y-axis, and z-axis can refer to different directions that are mutually orthogonal, but are not mutually orthogonal.

[0344] Organic Light Emitting Diode FIG. 1 is a cross-sectional view showing an organic light-emitting diode according to one embodiment of the present invention.

[0345] Referring to FIG. 1, the organic light emitting diode includes an anode 10, a cathode 70, an emitting layer 40 disposed between the two electrodes, a hole conducting layer 20 disposed between the anode 10 and the emitting layer 40, and an electron conducting layer 50 disposed between the emitting layer 40 and the cathode 70. The hole conducting layer 20 includes a hole transport layer 25 that transports holes and a hole injection layer 23 that facilitates hole injection. The electron conducting layer 50 includes an electron transport layer 55 that transports electrons and an electron injection layer 53 that facilitates electron injection. In some embodiments, a hole blocking layer may be disposed between the emitting layer 40 and the electron transport layer 55. Also, an electron blocking layer may be disposed between the emitting layer 40 and the hole transport layer 25. However, the present invention is not limited thereto, and the electron transport layer 55 may function as a hole blocking layer, and the hole transport layer 25 may function as an electron blocking layer.

[0346] 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 combine to form excitons, and the excitons transition to the ground state to emit light.

[0347] The light-emitting layer 40 may be made of a single light-emitting material, or may include a host material and a dopant material. The single light-emitting material or the light-emitting dopant material may be a compound represented by any one of the above-mentioned 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 may be significantly improved. The thermally activated delayed fluorescent material has a form in which an electron-donating group and an electron-withdrawing group are linked to benzene, and the electron-withdrawing group is located at the ortho position to the electron-donating group. Therefore, the difference between the singlet energy and the triplet energy may be reduced to less than 0.3 eV. The thermally activated delayed fluorescent material may more efficiently promote the transition from the triplet excited state to the singlet excited state by heat (at room temperature or device operating temperature), thereby improving the quantum efficiency. In some embodiments, a suitable combination of one or more of red, green, and blue emission colors may be realized by suitable or appropriate introduction of the electron-donating group and the electron-withdrawing group.

[0348] The host material may be selected from the group consisting of mCP (N,N-dicarbazolyl-3,5-benzene), Alq3, CBP (4,4'-N,N'-dicarbazole-biphenyl), 9,10-di(naphthalen-2-yl)anthracene, TPBI (1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene), TBADN (3-tert-butyl-9,10-di(naphth-2-yl)anthracene), E3 (see chemical formula below), and BeBq2 (see chemical formula below).

[0349] JPEG2025011064000062.jpg36170

[0350] The hole injection layer 23 and / or the hole transport layer 25 are layers having a HOMO level between the work function level of the anode 10 and the HOMO level of the light emitting layer 40, and have a function of improving the efficiency of injection or transport of holes from the anode 10 to the light emitting layer 40. The electron injection layer 53 and / or the electron transport layer 55 are layers having a LUMO level between the work function level of the cathode 70 and the LUMO level of the light emitting layer 40, and have a function of improving the efficiency of injection or transport of electrons from the cathode 70 to the light emitting layer 40. The anode 10 can be a conductive metal oxide, a metal, a metal alloy, or a carbon material. The conductive metal oxide is at least one selected from the group consisting of ITO (indium tin oxide), FTO (fluorine tin oxide), ATO (antimony tin oxide), SnO2, ZnO, or a combination thereof. The metal or metal alloy suitable for the anode 10 is Au or CuI. The carbon material is graphite, graphene, or carbon nanotubes.

[0351] The hole injection layer 23 or the hole transport layer 25 may include a material that is commonly used as a hole transport material, and a single layer may include different hole transport materials or layers of different hole transport materials may include different hole transport materials. Examples of hole transport materials include mCP (N,N-dicarbazolyl-3,5-benzene); PEDOT:PSS (poly(3,4-ethylenedioxythiophene):polystyrenesulfonate); 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; copper(II) 1,10,15,20-tetraphenyl-4,4'-diaminobiphenyl; Porphyrin compound derivatives such as phenyl-21H,23H-porphyrin; 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'-tris[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 amine and styrylamine compounds; polysilane; etc. Such hole transporting materials can also act as an electron blocking layer.

[0352] The hole blocking layer serves to prevent or reduce the diffusion of triplet excitons or holes toward the cathode 70 and may be selected from appropriate hole blocking materials, such as oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives.

[0353] The electron transport layer 55 may be made of a material selected from the group consisting of TSPO1 (diphenylphosphine oxide-4-(triphenylsilyl)phenyl), tris(8-quinolinolato)aluminum (Alq3), 2,5-diarylsilole derivatives (PyPySPyPy), perfluoro compounds (PF-6P), COTs (octasubstituted cyclooctatetraenes), TAZ (see formula below), Bphen (4,7-diphenyl-1,10-phenanthroline), BCP (see formula below), and BAlq (see formula below).

[0354] JPEG2025011064000063.jpg42170

[0355] The electron injection layer 53 can be, for example, LiF, NaCl, CsF, Li2O, BaO, BaF2, Liq (lithium quinolate).

[0356] The cathode 70 is a conductive film having a lower work function than the anode 10, and is made of aluminum, magnesium, calcium, sodium, potassium, indium, yttrium, lithium, silver, lead, cesium, or the like, or a combination of two or more of these metals.

[0357] The anode 10 and the cathode 70 may be formed using a sputtering method, a vapor phase deposition method, an ion beam deposition method, etc. 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 one another by a deposition method or a coating method such as spraying, spin coating, dipping, printing, doctor blade, or electrophoresis.

[0358] The organic light emitting diode may be disposed on a substrate that is disposed on either the anode 10 or the cathode 70. That is, the anode 10 may be formed on the substrate before the cathode 70, or the cathode 70 may be formed before the anode 10.

[0359] The substrate is a light-transmitting substrate as a flat plate member, and in this 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), etc. However, the present invention is not limited thereto, and the substrate may be a metal substrate capable of reflecting light.

[0360] Examples of the present invention will be described below to aid in the understanding of the present invention. However, it should be understood that the following examples are provided to aid in the understanding of the present invention and are not intended to limit the scope of the present invention.

[0361] Working Example

[0362] Reaction Scheme 1 JPEG2025011064000064.jpg83170

[0363] In reaction scheme 1, the product is R 1 and R 2 Compound 1 is when both R and R are hydrogen. 1 is a methyl group, and R 2 is hydrogen, R 1 is a t-butyl group, and R 2 is hydrogen, R 1 is hydrogen and R 2 When is a methyl group, the compound is 37.

[0364] Synthesis Example 1: Synthesis of Compound 1 Phase 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 oxygen was removed from the solution by bubbling nitrogen. After oxygen was removed, the mixture was refluxed and stirred for 24 hours. The reaction solution was extracted with methylene chloride and then subjected to column chromatography using a methylene chloride / hexane mixed solvent as an eluent to obtain 15.99 g of 9-(2-bromophenyl)carbazole. 9-(2-bromophenyl)carbazole: Mass spectrometry (EI) m / z 322 [(M+H) + ]

[0365] Phase 2 9-(2-Bromophenyl)carbazole (10 g, 31.03 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborane) (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 the solution was deoxygenated by bubbling nitrogen. After deoxygenation, the mixture was refluxed and stirred for 24 hours. The reaction solution was extracted with methylene chloride, and then column chromatography was performed using a methylene chloride / hexane mixed solvent as the 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 spectrometry (EI) m / z 369[(M+H) + ]

[0366] Phase 39-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl)carbazole (3g, 8.12mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.61g, 9.75mmol), tetrakis(triphenylphosphine)palladium(0) (0.28g, 0.24mmol) were added to a mixed solvent of tetrahydrofuran (60mL) and potassium carbonate 2M solution (20mL), and then refluxed for 24 hours. The reaction solution was extracted with methylene chloride, and purified by column chromatography using a mixed solvent of methylene chloride / hexane as an eluent, and finally 3.31g of pure white solid was obtained through sublimation purification.

[0367] compound 1 : Yield 86%, mass spectrometry (EI) m / z 474[(M+H) + ]. Elemental analysis theoretical value C 33 H 22 N 4 : C, 83.52%; H, 4.67%; N, 11.81%. Measurements: 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).

[0368] Synthesis Example 2: Synthesis of Compound 2 Compound 2 was obtained in a yield of 83% by the same method as in Synthesis Example 1, except that 3,6-dimethylcarbazole was used instead of carbazole in Step 1 of Synthesis Example 1.

[0369] compound 2 :Mass spectrometry (FAB) m / z 502[(M+H) + ]. Elemental analysis theoretical value C 35 H 26 N 4 : C (83.64%) H (5.21%) N (11.15%) Measurements: C, 83.69%; H, 5.26%; N, 11.09%. 1H 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).

[0370] Synthesis Example 3: Synthesis of Compound 3 Compound 3 was obtained in a yield of 81% by the same method as in Synthesis Example 1, except that 3,6-di-t-butylcarbazole was used instead of carbazole in Step 1 of Synthesis Example 1.

[0371] compound 3 :Mass spectrometry (EI) m / z 586[(M+H) + ]. Elemental analysis theoretical value C 41 H 38 N 4 : C (83.92%) H (6.53%) N (9.55%) Measurements: 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).

[0372] Synthesis Example 4: Synthesis of Compound 37 Compound 37 was obtained in 78% yield by the same method as in 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.

[0373] compound 37 :Mass spectrometry (FAB) m / z 502[(M+H) + ]. Elemental analysis theoretical value C 35 H 26 N 4: C(83.64%)H(5.21%)N(11.15%)Measured values: 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).

[0374] Synthesis Example 5: Synthesis of Compound 22

[0375] Reaction Scheme 2-1 JPEG2025011064000065.jpg32170

[0376] Phase 1 : Diphenylamine (10.0 g, 59.09 mmol), 1,2-dibromobenzene (27.88 g, 118.19 mmol), sodium tert-butoxide (6.814 g, 70.908 mmol), palladium acetate (0.663 g, 2.95 mmol) and tri-tert-butylphosphine (1.19 g, 5.91 mmol) were dissolved in toluene (300 mL) and oxygen was removed from the solution by bubbling nitrogen. After oxygen was removed, the mixture was refluxed and stirred for 24 hours. The reaction solution was extracted with methylene chloride and then subjected to column chromatography using a methylene chloride / hexane mixed solvent as an eluent to obtain 12.21 g of intermediate 22-1.

[0377] Intermediate 22-1 :Mass spectrometry (EI) m / z 324[(M+H) + ]

[0378] Reaction Scheme 2-2 JPEG2025011064000066.jpg42170

[0379] Phase 2: Intermediate 22-1 (10g, 30.84mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborane) (11.74g, 46.26mmol), potassium acetate (9.08g, 92.52mmol) and 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (0.76g, 0.93mmol) were dissolved in 1,4-dioxane (180mL), and oxygen was removed from the solution by bubbling nitrogen. After removing oxygen, the mixture was refluxed and stirred for 24 hours. The reaction solution was extracted with methylene chloride, and column chromatography was performed using a methylene chloride / hexane mixed solvent as an eluent to obtain 4.58g of intermediate 22-2.

[0380] Intermediate 22-2 :Mass spectrometry (EI) m / z 371[(M+H) + ].

[0381] Reaction Scheme 2-3 JPEG2025011064000067.jpg39170

[0382] Phase 3 : Intermediate 22-2 (3 g, 8.08 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.59 g, 9.75 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.28 g, 0.24 mmol) were added to a mixed solvent of tetrahydrofuran (60 mL) and potassium carbonate 2M solution (20 mL) and refluxed for 24 hours. The reaction solution was extracted with methylene chloride and purified by column chromatography using a mixed solvent of methylene chloride / hexane as an eluent, and finally 3.08 g of pure white solid compound 22 was obtained through sublimation purification.

[0383] compound 22 : Yield 86%, mass spectrometry (EI) m / z 476[(M+H) + ]. Elemental analysis theoretical value C 33 H 24 N 4: C, 83.17%; H, 5.08%; N, 11.76%. Measurements: C, 82.16%; H, 5.12%; N, 11.77%. 1 H 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).

[0384] Synthesis Example 6: Synthesis of Compound 23

[0385] Reaction Scheme 3 JPEG2025011064000068.jpg42170

[0386] Compound 23 was obtained in 78% yield by the same method as in Synthesis Example 5, except that in Step 1 of Synthesis Example 5, di-p-tolylamine was used instead of diphenylamine, and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)-N,N-di-p-tolylaniline was obtained in Step 2 and used in Step 3.

[0387] compound 23 :Mass spectrometry (EI) m / z 504[(M+H) + ]. Elemental analysis theoretical value C 35 H 28 N 4 : C (83.30%) H (5.59%) N (11.10%) Measurements: 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).

[0388] Synthesis Example 7: Synthesis of Compound 36

[0389] Reaction Scheme 4-1 JPEG2025011064000069.jpg39170

[0390] (2-(carbazol-9-yl)phenyl)boronic 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 methylene chloride, and then column chromatography was performed using a methylene chloride / hexane mixed solvent as an eluent to obtain 7.99 g of intermediate 36-1.

[0391] Intermediate 36-1 :Mass spectrometry (EI) m / z 432[(M+H) + ].

[0392] Reaction Scheme 4-2 JPEG2025011064000070.jpg34170

[0393] Intermediate 36-1 (3 g, 6.94 mmol) and copper cyanide (2.18 g, 24.31 mmol) were dissolved in N-methyl-2-pyrrolidone (50 mL), and oxygen was removed from the solution by bubbling nitrogen. After oxygen was removed, the mixture was refluxed and stirred for 24 hours. The reaction solution was extracted with methylene chloride, and column chromatography was performed using a methylene chloride / hexane mixed solvent as an eluent to obtain 2.49 g of compound 36.

[0394] compound 36 :Mass spectrometry (EI) m / z 423[(M+H) + ]. Elemental analysis theoretical value C 28 H 17 N 5 : C (79.42%) H (4.05%) N (16.54%) Measurements: 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).

[0395] Reaction Scheme 5 JPEG2025011064000071.jpg81170

[0396] In reaction scheme 5, the product is R 1 and R 2 Compound 61 is when both R and R are hydrogen. 1 is hydrogen and R 2 When is a methyl group, the compound is 63.

[0397] Synthesis Example 8: Synthesis of Compound 61 Phase 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) and potassium carbonate (7.74g, 56.03mmol) were dissolved in toluene (120mL), ethanol (60mL) and distilled water (90mL), and oxygen was removed from the solution by bubbling nitrogen. After removing oxygen, the mixture was stirred at room temperature for 1 hour, refluxed and stirred at 130°C for 15 hours. Then, the solvent was removed using a rotary evaporator, and the reaction solution was vacuum dried. The dried mixture was extracted with methylene chloride, and then column chromatography was carried out using a mixed solvent of methylene chloride / hexane as an eluent to obtain 5.4 g of 2-(2-fluorophenyl)-4,6-diphenyl-1,3,5-triazine.

[0398] 2-(2-fluorophenyl)-4,6-diphenyl-1,3,5-triazine: Mass Spectroscopy (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).

[0399] Phase 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 dimethylformamide (100 mL) and refluxed at 160° C. for 24 hours. The reaction solution was extracted with methylene chloride, and then purified by column chromatography using a methylene chloride / hexane mixed solvent as an eluent. Finally, 0.63 g of yellow solid compound 61 was obtained through sublimation purification.

[0400] compound 61 : Yield 49.5%, mass spectrometry (EI) m / z 424[(M+H) + ]. Elemental analysis theoretical value C 29 H 20 N 4 : C (82.05%) H (4.75%) N (13.20%) Measurements: 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).

[0401] Synthesis Example 9: Synthesis of Compound 63 2-(2-fluorophenyl)-4,6-diphenyl-1,3,5-triazine (1.50 g, 4.58 mmol) obtained in step 1 of Synthesis Example 8, 3-methylindole (1.50 g, 11.45 mmol) and sodium tert-butoxide (1.10 g, 11.45 mmol) were added to a dimethylformamide (100 mL) solvent in a similar manner to step 2 of Synthesis Example 8 to obtain 1.17 g of compound 63.

[0402] compound 63 : Yield 58.07%, mass spectrometry (EI) m / z 438[(M+H) + ]. Elemental 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).

[0403] Synthesis Example 10: Synthesis of Compound 52

[0404] Reaction Scheme 6 JPEG2025011064000072.jpg39170

[0405] 2-(2-Fluorophenyl)-4,6-diphenyl-1,3,5-triazine (1.00 g, 3.05 mmol), 5H-benzofuro[3,2-c]carbazole (0.98 g, 3.82 mmol), and sodium hydride (0.10 g, 3.90 mmol) were mixed in dimethylformamide (100 mL) and refluxed at 160° C. for 24 hours. The reaction solution was extracted with methylene chloride, and then purified by column chromatography using a methylene chloride / hexane mixed solvent as an eluent. Finally, 1.35 g of yellow solid compound 52 was obtained through sublimation purification.

[0406] compound 52 : Yield 78.4%, mass spectrometry (EI) m / z 565[(M+H) + ]. 1H 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).

[0407] Synthesis Example 11: Synthesis of Compound 67

[0408] Reaction Scheme 7 JPEG2025011064000073.jpg45170

[0409] 9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbazole (8.0g, 27.9mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (3.0g, 13.3mmol), and tetrakis(triphenylphosphine)palladium(0) (1.53g, 1.33mmol) were added to a mixture of tetrahydrofuran (100mL) and potassium carbonate 2M solution (40mL) and refluxed for 24 hours. The reaction solution was extracted with methylene chloride, and then purified by column chromatography using a mixture of methylene chloride / hexane as the eluent. Finally, a pure white solid was obtained through sublimation purification in a yield of 71%.

[0410] compound 67 :Mass spectrometry (EI) m / z 639[(M+H) + ]. Elemental analysis theoretical value C 45 H 29 N 5 : C(84.48%)H(4.57%)N(10.95%)Measurement 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).

[0411] Synthesis Example 12: Synthesis of Compound 83

[0412] Reaction Equation 8 JPEG2025011064000074.jpg58170

[0413] 9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbazole (15.4g, 53.7mmol), cyanuric chloride (3.0g, 16.3mmol), and tetrakis(triphenylphosphine)palladium(0) (2.82g, 2.44mmol) were added to a mixture of tetrahydrofuran (100mL) and 2M potassium carbonate solution (40mL) and refluxed for 24 hours. The reaction solution was extracted with methylene chloride and then purified by column chromatography using a mixture of methylene chloride / hexane as the eluent, and finally a pure white solid was obtained through sublimation purification in a yield of 37%.

[0414] compound 83 :Mass spectrometry (EI) m / z 803[(M+H) + ]. Elemental analysis theoretical value C 57 H 36 N 6 : C(85.05%)H(4.51%)N(10.44%)Measurement 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).

[0415] Manufacturing Example 1: Manufacturing of delayed fluorescent organic light-emitting diode

[0416] (ITO / PEDOT:PSS / TAPC / mCP / mCP:Compound 1 / TSPO1 / TPBi / LiF / Al) The glass substrate on which the anode (ITO) was evaporated was ultrasonically cleaned for 30 minutes using pure water and isopropyl alcohol. The cleaned ITO substrate was surface-treated using short-wavelength ultraviolet light, after which PEDOT:PSS (poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate)) was spin-coated to form a 60-nm-thick hole injection layer. Then, TAPC (1,1-bis[4-[N,N'-di(p-tolyl)amino]phenyl]cyclohexane) was applied at 1×10 -6 The hole transport layer was formed by evaporation at a rate of 0.1 nm / s under a pressure of 1000 torr. Then, mCP (N,N-dicarbazolyl-3,5-benzene) was evaporated at 1 × 10 -6 The deposition was performed at a rate of 0.1 nm / s at a pressure of 1000 torr to form a 10 nm exciton blocking layer. -6 Under a pressure of 1000 torr, the host material mCP was co-deposited at a speed of 0.1 nm / s and the delayed fluorescent dopant material compound 1 synthesized in Synthesis Example 1 was co-deposited at a speed of 0.005 nm / s to form an emission layer doped with 5% dopant in the host. TSPO1 (diphenylphosphine oxide-4-(triphenylsilyl)phenyl) and TPBi (1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene) were co-deposited at a speed of 1×10 -6 The layers are then evaporated at a rate of 0.1 nm / s under a pressure of 1000 MPa to form an exciton blocking layer of 5 nm and an electron transport layer of 30 nm. Then, LiF, an electron injection material, is evaporated at a rate of 1×10 -6 The deposition was performed at a rate of 0.01 nm / s under a pressure of 1000 torr to form a 1 nm electron injection layer. -6 Al was evaporated at a rate of 0.5 nm / sec at a pressure of 100 torr to form a cathode, forming an organic light-emitting diode. After the device was formed, it was encapsulated using a CaO moisture absorbent and a glass cover slip.

[0417] 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, and CIE 1931 color coordinates of x=0.15 and y=0.22 at a voltage of 6 V, which indicates that the device has excellent or suitable blue light emission properties. Such results exceed the limit of 5% (20% light extraction efficiency), which is the maximum external quantum efficiency obtained from a general fluorescent device, and are also direct evidence that triplet energy is converted into singlet energy. This is due to intersystem crossing, which is a characteristic of thermally activated delayed fluorescent materials.

[0418] Manufacturing Example 2: Manufacturing of delayed fluorescent organic light-emitting diode

[0419] (ITO / PEDOT:PSS / TAPC / mCP / mCP:Compound 2 / TSPO1 / TPBi / LiF / Al) An organic light emitting diode was prepared in substantially the same manner as in Preparation Example 1, except that Compound 2 prepared in Synthesis Example 2 was used as a delayed fluorescent dopant material.

[0420] The organic light-emitting diode according to Preparation Example 2, which uses Compound 2 as an emitting dopant material, has a quantum efficiency of 14.7%, a current efficiency of 30.9 cd / A, a power efficiency of 14.9 lm / W, and CIE 1931 color coordinates of x=0.17 and y=0.34 at a voltage of 6 V, which indicates that the blue light emission property is excellent or suitable.

[0421] Manufacturing Example 3: Manufacturing of delayed fluorescent organic light-emitting diode

[0422] (ITO / PEDOT:PSS / TAPC / mCP / mCP:Compound 3 / TSPO1 / TPBi / LiF / Al) An organic light emitting diode was prepared in substantially the same manner as in Preparation Example 1, except that Compound 3 prepared in Synthesis Example 3 was used as a delayed fluorescent dopant material.

[0423] The organic light-emitting diode according to Preparation Example 3, which uses Compound 3 as an emitting dopant material, has a quantum efficiency of 12.3%, a current efficiency of 24.0 cd / A, a power efficiency of 12.6 lm / W, and CIE 1931 color coordinates of x=0.16 and y=0.30 at a voltage of 6 V, which indicates that it has excellent or suitable blue light emission properties.

[0424] Manufacturing Example 4: Manufacturing of delayed fluorescent organic light-emitting diode

[0425] (ITO / PEDOT:PSS / TAPC / mCP / mCP:Compound 37 / TSPO1 / TPBi / LiF / Al) An organic light emitting diode was prepared in substantially the same manner as in Preparation Example 1, except that the compound 37 synthesized in Synthesis Example 4 was used as a delayed fluorescent dopant material.

[0426] The organic light-emitting diode according to Preparation Example 4, which uses Compound 37 as a light-emitting dopant material, has a quantum efficiency of 11.5%, a current efficiency of 29.1 cd / A, a power efficiency of 13.8 lm / W, and CIE 1931 color coordinates of x=0.16 and y=0.20 at a voltage of 6 V, which indicates that it has excellent or suitable blue light emission properties.

[0427] Manufacturing Example 5: Manufacturing of delayed fluorescent organic light-emitting diode

[0428] (ITO / PEDOT:PSS / TAPC / mCP / mCP:Compound 22 / TSPO1 / TPBi / LiF / Al) An organic light emitting diode was prepared in substantially the same manner as in Preparation Example 1, except that the compound 22 synthesized in Synthesis Example 5 was used as a delayed fluorescent dopant material.

[0429] The organic light-emitting diode according to Preparation Example 5, which uses compound 22 as a light-emitting dopant material, has a quantum efficiency of 17.2%, a current efficiency of 45.0 cd / A, a power efficiency of 31.4 lm / W, and CIE 1931 color coordinates of x=0.21 and y=0.45 at a voltage of 9V, which indicates that it has excellent or suitable blue light emission properties.

[0430] Production Example 6: Production of delayed fluorescent organic light-emitting diode

[0431] (ITO / PEDOT:PSS / TAPC / mCP / mCP:Compound 52 / TSPO1 / TPBi / LiF / Al) An organic light emitting diode was prepared in substantially the same manner as in Preparation Example 1, except that the compound 52 synthesized in Synthesis Example 10 was used as a delayed fluorescent dopant material.

[0432] The organic light-emitting diode according to Preparation Example 6, which uses compound 52 as a light-emitting dopant material, has a quantum efficiency of 12.5%, a current efficiency of 19.8 cd / A, a power efficiency of 17.8 lm / W, and CIE 1931 color coordinates of x=0.15 and y=0.20 at a voltage of 9 V, which indicates that it has excellent or suitable blue light emission properties.

[0433] Manufacturing Example 7: Manufacturing of delayed fluorescent organic light-emitting diode

[0434] (ITO / PEDOT:PSS / TAPC / mCP / mCP:Compound 23 / TSPO1 / TPBi / LiF / Al) An organic light emitting diode was prepared in substantially the same manner as in Preparation Example 1, except that the compound 23 synthesized in Synthesis Example 6 was used as a delayed fluorescent dopant material.

[0435] The organic light-emitting diode according to Preparation Example 7, which uses compound 23 as a light-emitting dopant material, has a quantum efficiency of 16.3%, a current efficiency of 54.6 cd / A, a power efficiency of 32.8 lm / W, and CIE 1931 color coordinates of x=0.35 and y=0.58 at a voltage of 9V, which indicates that it has excellent or suitable blue light emission properties.

[0436] Production Example 8: Production of delayed fluorescent organic light-emitting diode

[0437] (ITO / PEDOT:PSS / TAPC / mCP / mCP:Compound 36 / TSPO1 / TPBi / LiF / Al) An organic light emitting diode was prepared in substantially the same manner as in Preparation Example 1, except that the compound 36 synthesized in Synthesis Example 7 was used as a delayed fluorescent dopant material.

[0438] The organic light-emitting diode according to Preparation Example 8, which uses Compound 36 as a light-emitting dopant material, has a quantum efficiency of 11.7%, a current efficiency of 26.9 cd / A, a power efficiency of 10.4 lm / W, and CIE 1931 color coordinates of x=0.55 and y=0.45 at a voltage of 6 V, which indicates that it has excellent or suitable blue light emission properties.

[0439] Manufacturing Example 9: Manufacturing of delayed fluorescent organic light-emitting diode

[0440] (ITO / PEDOT:PSS / TAPC / mCP / mCP:Compound 67 / TSPO1 / TPBi / LiF / Al) An organic light emitting diode was prepared in substantially the same manner as in Preparation Example 1, except that the compound 67 synthesized in Synthesis Example 11 was used as a delayed fluorescent dopant material.

[0441] The organic light-emitting diode according to Preparation Example 9, which uses Compound 67 as a light-emitting dopant material, has a quantum efficiency of 12.2%, a current efficiency of 18.5 cd / A, a power efficiency of 6.47 lm / W, and CIE 1931 color coordinates of x=0.17 and y=0.21 at a voltage of 8 V, which indicates that it has excellent or suitable blue light emission properties.

[0442] Production Example 10: Production of delayed fluorescent organic light-emitting diode

[0443] (ITO / PEDOT:PSS / TAPC / mCP / mCP:Compound 83 / TSPO1 / TPBi / LiF / Al) An organic light emitting diode was prepared in substantially the same manner as in Preparation Example 1, except that the compound 83 synthesized in Synthesis Example 12 was used as a delayed fluorescent dopant material.

[0444] The organic light-emitting diode according to Preparation Example 10, which uses Compound 83 as a light-emitting dopant material, has a quantum efficiency of 14.9%, a current efficiency of 23.0 cd / A, a power efficiency of 9.57 lm / W, and CIE 1931 color coordinates of x=0.15 and y=0.22 at a voltage of 8 V, which indicates that it has excellent or suitable blue light emission properties.

[0445] Comparative Example 1: Fabrication of delayed fluorescent organic light-emitting diode

[0446] (ITO / PEDOT:PSS / TAPC / mCP / mCP:CC2TA / TSPO1 / TPBi / LiF / Al) An organic light emitting diode was prepared substantially similarly to Preparation Example 1, except that 2,4-bis3-(9H-carbazol-9-yl)-9H-carbazol-9-yl-6-phenyl-1,3,5-triazine (CC2TA) reported in the paper (APPLIED PHYSICS LETTERS 101,093306(2012)) was used as a delayed fluorescent dopant material.

[0447] The organic light-emitting diode according to Comparative Example 1 using CC2TA as an emitting dopant material had a quantum efficiency of 11.5%, a current efficiency of 29.1 cd / A, a power efficiency of 13.8 lm / W, and CIE 1931 color coordinates of x=0.20 and y=0.44 at a voltage of 6 V, which indicates excellent or suitable blue light emission properties.

[0448] Using the thermally activated delayed fluorescent compounds in Preparation Examples 1 to 10, 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. 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 obtained from a general fluorescent element, indicating that the thermally activated delayed fluorescent compound according to the present invention facilitates efficient reverse intersystem crossing from the triplet state to the singlet state. In some embodiments, the organic light-emitting diode according to Comparative Example 1 using CC2TA, which is known as an existing delayed fluorescent emitting material, exhibits a quantum efficiency of 11.5%, while the organic light-emitting diodes according to Examples 2 to 10 exhibit very high or the same quantum efficiency. In particular, the green light-emitting device (Preparation Example 5) exhibits a high quantum efficiency of 17% or more, and exhibits superior or suitable luminescence characteristics compared to existing fluorescent elements.

[0449] Evaluation example 1 Table 1 shows the values ​​calculated by molecular calculation techniques for Compound 1 prepared by Synthesis Example 1, Comparative Compound A, and Comparative Compound B. The molecular calculations were performed using the Gaussian 09 program through the B3LYP method according to density functional theory for the 6-31 G* basis set.

[0450] [Table 1]

[0451] Referring to Table 1, it can be seen that Comparative Compound A or B has a similar form to Compound 1, but the electron donating group carbazole and the electron withdrawing group diphenyltriazine are in the meta position in Comparative Compound A and in the para position in Comparative Compound B. As a result of calculation, it was shown that as the positions of carbazole and diphenyltriazine move from ortho to meta and from meta to para, the singlet energy gradually increases and the triplet energy gradually decreases. As a result, it was shown that the energy difference between the singlet state and the triplet state is the smallest in the ortho form. The smaller the energy difference between the singlet state and the triplet state, the easier the reverse intersystem crossing (RISC) and the better the thermally activated delayed fluorescence properties.

[0452] FIG. 2 shows the molecular orbital distribution of Compound 1 prepared by Synthesis Example 1, Comparative Compound A and Comparative Compound B. The molecular orbital distribution was calculated using the Gaussian 09 program through the B3LYP method according to density functional theory using the 6-31 G* basis set.

[0453] In order to effectively show fluorescence properties, the overlap between HOMO and LUMO must be at a certain level. As a result of calculations, it was predicted that the HOMO and LUMO of ortho-, meta-, and para-types are overlapped on the central linking unit benzene, and the fluorescence properties of ortho-type materials are similar to those of other types of materials. These results indicate that ortho-type materials can upconvert triplet excitons formed during electroluminescence into singlet excitons through RISC more effectively than meta- and para-type materials, and the singlet excitons can show effective fluorescence emission.

[0454] Synthesis Example 13: Synthesis of Compound 93

[0455] Reaction Scheme 9 JPEG2025011064000076.jpg63170

[0456] Synthesis of intermediate 93-1: 9H-Carbazole-1,2,3,4,5,6,7,8-d8 (CAS#=38537-24-5, (2eq)) was dissolved in THF and reacted with nBuLi at 0°C, followed by dropwise addition of cyanuric chloride. The mixture was then stirred at 70°C overnight to obtain intermediate 93-1, which was confirmed by MS.

[0457] C 27 D 16 ClN 5 M+1 462.3

[0458] Synthesis of intermediate 93-2: 9H-Carbazole-1,2,3,4,5,6,7,8-d (1eq), 1-Bromo-2-fluorobenzene (1.5eq) and K 3 PO 4 (2 eq) was dissolved in DMF (N,N-dimethylformamide) and stirred overnight at 160° C. The intermediate 93-2 was confirmed by MS.

[0459] C 18 H 4 D 8 BrN M+1:330.2

[0460] Synthesis of intermediate 93-3: Intermediate 93-2 (1 eq) was dissolved in THF (tetrahydrofuran) and reacted with nBuLi (1.2 eq) at -78°C. After 1 hour, trimethylborate was added dropwise. The mixture was then gradually heated to room temperature to obtain intermediate 93-3. The intermediate 93-3 was confirmed by MS.

[0461] C 18 H 6 D 8 BNO 2 M+1 295.3

[0462] Synthesis of compound 93: 2.1 g of the intermediate 93-1, 1.6 g of the intermediate 93-3, 0.21 g of tetrakis(triphenylphosphine)palladium, and 1.6 g of potassium carbonate were placed in a reaction vessel, dissolved in 40 mL of toluene, 10 mL of ethanol, and 10 mL of distilled water, and then refluxed for 24 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate, and the collected organic layer was dried over magnesium sulfate, and the solvent was evaporated. The residue obtained by evaporation was separated and purified by silica gel column chromatography to obtain 1.8 g (yield 59%) of compound 93. The compound 93 was confirmed by LC-MS.

[0463] C 45 H 4 D 24 N 6 M+1:677.4

[0464] Synthesis Example 14: Synthesis of Compound 94

[0465] Reaction Scheme 10 JPEG2025011064000077.jpg48170

[0466] Synthesis of intermediate 94-1: 9H-Carbazole-1,2,3,4,5,6,7,8-d (1eq), 1-Bromo-2-fluorobenzene-3,4,5,6-d4 (1.5eq, CAS#=50592-35-3) and K 3 PO 4 (2 eq) was dissolved in DMF and stirred overnight at 160° C. The intermediate 94-1 was confirmed by MS.

[0467] C 18 D 12 BrN M+1:334.0

[0468] Synthesis of intermediate 94-2: Intermediate 94-1 (1 eq) was dissolved in THF and reacted with nBuLi (1.2 eq) at -78°C. After 1 hour, trimethylborate (1.4 eq) was added dropwise. The mixture was then gradually warmed to room temperature to obtain intermediate 94-2. The intermediate 94-2 was confirmed by MS.

[0469] C 18 H 2 D 12 BNO 2 M+1:301.2

[0470] Synthesis of compound 94: 3.7g of the intermediate 93-1, 2.9g of the intermediate 94-2, 0.37g of tetrakis(triphenylphosphine)palladium and 2.8g of potassium carbonate were placed in a reaction vessel, dissolved in 80mL of toluene, 20mL of ethanol and 20mL of distilled water, and then refluxed for 24 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate, and the collected organic layer was dried over magnesium sulfate, and the solvent was evaporated. The residue obtained by evaporation was separated and purified by silica gel column chromatography to obtain 3.3g (yield 61%) of compound 94. The compound 94 was confirmed by LC-MS.

[0471] C 45 D 28 N 6 M+1:681.4

[0472] Synthesis Example 15: Synthesis of Compound 98

[0473] Reaction Scheme 11 JPEG2025011064000078.jpg59170

[0474] Synthesis of intermediate 98-1: 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, which was confirmed by MS.

[0475] C 13 HD 7 N 2 M+1:200.21

[0476] Synthesis of intermediate 98-2: Intermediate 93-1 was reacted with 2-fluorophenylboronic acid (CAS#=1993-03-9) under Pd catalysis and basic conditions to give intermediate 98-2, which was confirmed by MS.

[0477] C 33 H 4 D 16 FN 5 M+1:522.29

[0478] Synthesis of compound 98: 1.3 g of the intermediate 98-1, 3.1 g of the intermediate 98-2, 3.1 g of potassium phosphate and 50 mL 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, and the collected organic layer was dried over magnesium sulfate, and the solvent was evaporated. The residue obtained by evaporation was separated and purified by silica gel column chromatography to obtain 2.6 g (yield 63%) of compound 98. The compound 98 was confirmed by LC-MS.

[0479] C 46 H 4 D 23 N 7 M+1:701.34

[0480] Synthesis Example 16: Synthesis of Compound 104

[0481] Reaction Scheme 12 JPEG2025011064000079.jpg43170

[0482] Synthesis of intermediate 104-1: 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 Pd catalyst and basic conditions to obtain intermediate 104-1. The intermediate 104-1 was confirmed by MS.

[0483] C 21 H 4 D 10 FN3 M+1:338.21

[0484] Synthesis of compound 104: Intermediate 104-1 4.1g, Intermediate 98-1 2.7g, K 3 PO 4 6.4g and 50mL of DMF were 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 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 (72% yield) of compound 104. Compound 104 was confirmed by LC-MS.

[0485] C 34 H 4 D 17 N 5 M+1:517.27

[0486] Synthesis Example 17: Synthesis of Compound 105

[0487] Reaction Scheme 13 JPEG2025011064000080.jpg84170

[0488] Synthesis of intermediate 105-1: 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. The intermediate 105-1 was confirmed by MS.

[0489] C 13 HD 7 N 2 M+1:200.13

[0490] Synthesis of compound 105: Intermediate 104-1 3.7g, Intermediate 105-1 2.4g, K 3 PO 45.8g and DMF were added to a RBF and stirred at 120°C for 12 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate, and the collected organic layer was dried over magnesium sulfate, and the solvent was evaporated. The residue obtained by evaporation was separated and purified by silica gel column chromatography to obtain 2.9g (yield 51%) of compound 105. The compound 105 was confirmed by LC-MS.

[0491] C 34 H 4 D 17 N 5 M+1:517.28

[0492] Synthesis Example 18: Synthesis of Compound 114

[0493] Reaction Scheme 14 JPEG2025011064000081.jpg121170

[0494] Synthesis of intermediate 114-1: Carbazole-d8 (CAS#=38537-24-5) was reacted with nBuLi and then with cyanuric chloride to give intermediate 114-1, which was confirmed by MS.

[0495] C 15 D 8 Cl 2 N 4 M+1:323.08

[0496] Synthesis of intermediate 114-2: Intermediate 114-1 and intermediate 93-3 were reacted under Pd catalyst and basic conditions to obtain intermediate 114-2, which was confirmed by MS.

[0497] C 33 H 4 D 16 ClN 5 M+1:538.19

[0498] Synthesis of intermediate 114-3: Intermediate 114-2 was reacted with 2-fluorophenylboronic acid (CAS#=1993-03-9) under Pd catalysis and basic conditions to give intermediate 114-3, which was confirmed by MS.

[0499] C 39 H 8 D 16 FN 5 M+1:598.31

[0500] Synthesis of compound 114: Intermediate 114-3 2.1g, Intermediate 105-1 0.77g, K 3 PO 4 1.9g and 50mL of DMF were added to a RBF and stirred at 120°C for 12 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate, and the collected organic layer was dried over magnesium sulfate, and the solvent was evaporated. The residue obtained by evaporation was separated and purified by silica gel column chromatography to obtain 2.1g (77% yield) of compound 114. Compound 114 was confirmed by LC-MS.

[0501] C 52 H 8 D 23 N 7 M+1:777.31

[0502] Synthesis Example 19: Synthesis of Compound 116

[0503] Reaction Scheme 15 JPEG2025011064000082.jpg99170

[0504] Synthesis of intermediate 116-1: 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. The intermediate 116-1 was confirmed by MS.

[0505] C 18 HD 12N M+1:256.21

[0506] Synthesis of compound 116: Intermediate 114-3 2.1g, Intermediate 116-1 1g, K 3 PO 4 1.9g and 30mL of DMF were added to a RBF and stirred at 120°C overnight. After the reaction was completed, the reaction solution was extracted with ethyl acetate, and the collected organic layer was dried over 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. The compound 116 was confirmed by LC-MS.

[0507] C 51 H 4 D 28 N 6 M+1:757.42

[0508] Synthesis Example 20: Synthesis of Compound 120

[0509] Reaction Scheme 16 JPEG2025011064000083.jpg83170

[0510] Synthesis of compound 120: 3.1g of intermediate 114-1, 7.3g of intermediate 94-2, 0.48g of tetrakis(triphenylphosphine)palladium and 3.6g of potassium carbonate were placed in a reaction vessel, dissolved in 80mL of toluene, 20mL of ethanol and 20mL of distilled water, and then refluxed for 24 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate, and the collected organic layer was dried over magnesium sulfate, and the solvent was evaporated. The residue obtained by evaporation was separated and purified by silica gel column chromatography to obtain 5.0g (yield 64%) of compound 120. The compound 120 was confirmed by LC-MS.

[0511] C 51 D 32 N 6 M+1:761.49

[0512] Synthesis Example 21: Synthesis of Compound 121

[0513] Reaction Scheme 17 JPEG2025011064000084.jpg70170

[0514] Synthesis of intermediate 121-1: Intermediate 114-1 and intermediate 94-2 were reacted under Pd catalyst and basic conditions to obtain intermediate 121-1, which was confirmed by MS.

[0515] C 33 D 20 ClN 5 M+1:542.29

[0516] Synthesis of intermediate 121-2: Carbazole-d8 (CAS#=38537-24-5) and 1,3-dibromo-2-fluorobenzene-4,5,6-d3 (CAS#=2768654-61-9) were reacted under basic conditions to obtain intermediate 121-2, which was confirmed by MS.

[0517] C 18 D 11 Br 2 N M+1:410.98

[0518] Synthesis of intermediate 121-3: Intermediate 121-2 and phenylboronic acid-5 (CAS#=215527-70-1) were reacted under Pd catalysis and basic conditions to obtain intermediate 121-3, which was confirmed by MS.

[0519] C 24 D 16 BrN M+1:414.13

[0520] Synthesis of intermediate 121-4: Intermediate 121-3 was reacted with nBuLi (1.2 eq) at -78 °C. The reaction solution was then added with B(OMe) 3(1.4eq) was reacted to obtain intermediate 121-4, which was confirmed by MS.

[0521] C 24 H 2 D 16 BNO 2 M+1:380.23

[0522] Synthesis of compound 121: 4.5g of intermediate 121-1, 3.8g of intermediate 121-4, 0.38g of tetrakis(triphenylphosphine)palladium and 2.9g of potassium carbonate were placed in a reaction vessel, dissolved in 80mL of toluene, 20mL of ethanol and 20mL of distilled water, and then refluxed for 24 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate, and the collected organic layer was dried over magnesium sulfate, and the solvent was evaporated. The residue obtained by evaporation was separated and purified by silica gel column chromatography to obtain 3.6g (yield 52%) of compound 121. The compound 121 was confirmed by LC-MS.

[0523] C 57 D 36 N 6 M+1:841.51

[0524] Synthesis Example 22: Synthesis of Compound 122

[0525] Reaction Scheme 18 JPEG2025011064000085.jpg73170

[0526] Synthesis of compound 122: 2.9g of intermediate 114-1, 7.5g of intermediate 121-4, 0.41g of tetrakis(triphenylphosphine)palladium and 3.1g of potassium carbonate were placed in a reaction vessel, dissolved in 80mL of toluene, 20mL of ethanol and 20mL of distilled water, and then refluxed for 24 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate, and the collected organic layer was dried over magnesium sulfate, and the solvent was evaporated. The residue obtained by evaporation was separated and purified by silica gel column chromatography to obtain 5.9g (71% yield) of compound 122. The compound 122 was confirmed by LC-MS.

[0527] C 63 D 40 N 6 M+1:921.57

[0528] Evaluation example 2 Table 2 shows the values ​​calculated by molecular calculation techniques for the compounds prepared in Synthesis Examples 13 to 22 and the comparative compounds C1 to C4. The molecular calculations were performed using the Gaussian 09 program through the B3LYP method according to density functional theory for the 6-31 G* basis set.

[0529] [Table 2] JPEG2025011064000087.jpg220170

[0530] Referring to Table 2, comparative compounds C1, C2, C3 and C4 have a similar form to the compound represented by Chemical Formula 2 according to the present invention, but the electron donating group and the electron withdrawing group are at the meta position in comparative compounds C2 and C3, and at the para position in comparative compounds C1 and C4, and comparative compounds C1 to C4 do not contain deuterium. As a result of calculation, it was shown that the ortho type has the smallest energy difference between the singlet state and the triplet state. The smaller the energy difference between the singlet state and the triplet state, the easier the reverse intersystem crossing (RISC) becomes, and the better the thermally activated delayed fluorescence properties become.

[0531] In order to effectively show fluorescence properties, the overlap between HOMO and LUMO must be at a certain level. As a result of calculations, it was predicted that the HOMO and LUMO of ortho-, meta-, and para-types are overlapped on the central linking unit benzene, and the fluorescence properties of ortho-type materials are similar to those of other types of materials. These results indicate that ortho-type materials can upconvert triplet excitons formed during electroluminescence into singlet excitons through RISC more effectively than meta- and para-type materials, and the singlet excitons can show effective fluorescence emission.

[0532] In the compound represented by Chemical Formula 2 according to the present invention, an electron donating group and an electron withdrawing group are introduced at the ortho-position of the benzene ring. In addition, the compound represented by Chemical Formula 2 according to the present invention is R 1 , R 2 , R 17 and R 18 At least one of the groups contains deuterium or R 22 ~R 25 At least one of the compounds contains deuterium. 1 The level is high, and the dopant excitons can be effectively blocked, resulting in a ΔE ST Therefore, the light emitting device including the compound has excellent characteristics in terms of driving voltage and maximum quantum efficiency.

[0533] Production Example 11: Production of Light-Emitting Device Anode: Corning 15 Ω / cm 2 A (1,200 Å) ITO glass substrate was cut to a size of 50 mm × 50 mm × 0.5 mm, ultrasonically cleaned using isopropyl alcohol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet light and ozone, and the glass substrate was placed in a vacuum deposition apparatus.

[0534] First, HATCN was formed on the substrate as a hole injection layer to a thickness of 100 Å, and then BCFN, a first hole transport material, was vacuum deposited to a thickness of 600 Å, and SiCzCz, a hole transport material, was vacuum deposited to a thickness of 50 Å as a second hole transport compound to form a hole transport layer.

[0535] On the hole transport layer, SiCzCz and Compound 93 as hosts, and PtON-TBBI as a phosphorescent dopant were simultaneously deposited in a weight ratio of 60:27:13 to form a light emitting layer having a thickness of 350 Å.

[0536] Then, mSiTrz was deposited on the light-emitting layer to a thickness of 50 Å as a first electron transport layer, and then mSiTrz and LiQ were simultaneously deposited in a ratio of 1:1 as a second electron transport layer to form an electron transport layer to a thickness of 350 Å. LiF, an alkali metal halide, was deposited on the electron transport layer to a thickness of 15 Å as an electron injection layer, and Al was vacuum-deposited to a thickness of 80 Å to form a LiF / Al electrode, thereby manufacturing an organic light-emitting device.

[0537] JPEG2025011064000088.jpg114170

[0538] Production Examples 12 to 20 and Comparative Examples 2 to 5 A light emitting device was manufactured in substantially the same manner as in Preparation Example 11, except that the compound in Table 2 below was used instead of Compound 93 when forming the light emitting layer.

[0539] Evaluation example 3 In order to evaluate the characteristics of the organic light-emitting devices manufactured in Manufacturing Examples 11 to 20 and Comparative Examples 2 to 5, a current density of 10 mA / cm 2 The driving voltage and maximum quantum efficiency were measured at 1000 s and the results are shown in Table 3.

[0540] The driving voltage and current density of the organic light-emitting element were measured using a source meter (Keithley Instruments, 2400 series), and the maximum quantum efficiency was measured using an external quantum efficiency measurement device C9920-2-12 manufactured by Hamamatsu Photonics. In evaluating the maximum quantum efficiency, the luminance / current density was measured using a luminance meter with calibrated wavelength sensitivity, and the maximum quantum efficiency was calculated assuming an angular luminance distribution (Lambertian) assuming a perfect diffuse reflection surface. The characteristic evaluation results of the organic light-emitting element are shown in Table 3 below.

[0541] [Table 3]

[0542] JPEG2025011064000090.jpg244170

[0543] It can be seen from Table 3 that the light emitting devices according to Examples 11 to 20 have superior characteristics in terms of driving voltage and maximum quantum efficiency compared to the light emitting devices according to Comparative Examples 2 to 5.

[0544] According to the embodiment, the light emitting device can have excellent characteristics in terms of driving voltage and maximum quantum efficiency by including the compound represented by Chemical Formula 2. In addition, the light emitting device can be used to manufacture high quality electronic devices and electronic equipment.

[0545] The present invention is not limited to the above-mentioned embodiments and the accompanying drawings. Although the exemplary embodiments and advantages thereof have been described in more detail herein, it should be understood that one or more suitable modifications, substitutions and alterations can be made in the present invention without departing from the scope of the present invention.

Claims

1. A luminescent material represented by Chemical Formula 2: [Chemical formula 2] In the above Chemical Formula 2, R １ and R ２ are each independently a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C6-C30 aralkyl group, or a substituted or unsubstituted C3-C30 heteroaryl group; R １ and R ２ optionally, together with the nitrogen to which they are attached, form a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heteroaryl group; R １７ and R １８ are each independently a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C30 alkyloxy group, a substituted or unsubstituted C3-C30 aryloxy group, a C1-C9 alkylsilyl group, or a substituted or unsubstituted -NR ａ R ｂ and R ａ and R ｂ are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group, or a substituted or unsubstituted C3-C30 heteroaryl group; R ａ and R ｂ optionally, together with the nitrogen to which they are attached, form a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heteroaryl group; R ２２ ~R ２５ are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted C4-C6 aryl group, or a substituted or unsubstituted C1-C3 alkyl group; Here, R １ , R ２ , R １７ and R １８ At least one selected from contains deuterium, or R ２２ ~R ２５ At least one selected from is deuterium.

2. In the above formula 2, R １ and R ２ The luminescent material of claim 1 , wherein, together with the nitrogen to which they are attached, form a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heteroaryl group.

3. In the above formula 2, R １ and R ２ and A1 to A2 form, together with the nitrogen to which they are attached, a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heteroaryl group represented by any one of the following structural formulae A1 to A6 and A9 to A19: In the structural formulas A1 to A6 and A9 to A19, R １１ ~R １４ are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C2 alkyl group, or a substituted or unsubstituted C6-C30 aryl group; Sub １ and Sub ２ are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C9 alkyloxy group, a substituted or unsubstituted -NR ｃ R ｄ , 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, a substituted or unsubstituted sulfone group, a substituted or unsubstituted C5-C30 arylsilyl group, a substituted or unsubstituted C5-C30 arylthio group, a substituted or unsubstituted C5-C30 aryloxy group, a substituted or unsubstituted C5-C30 arylamine group, or a substituted or unsubstituted C5-C30 aralkyl group; R ｃ and R ｄ are each independently selected from the group consisting of a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group, and a substituted or unsubstituted C3-C30 heteroaryl group; R ｃ and R ｄ optionally, together with the nitrogen to which they are attached, form a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heteroaryl group; Sub １ and Sub ２ are, independently of each other, selectively fused to the entity to which they are attached to form a substituted or unsubstituted ring group, or a substituted or unsubstituted aryl group.

4. In the above formula 2, R １ and R ２ and together with the nitrogen to which they are attached, form a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heteroaryl group represented by any one of the following structural formulas A1 to A45: In the structural formulas A1 to A45, R １１ ~R １４ are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C2 alkyl group, or a substituted or unsubstituted C6-C30 aryl group; Sub １ ~Sub ４ are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C9 alkyloxy group, a substituted or unsubstituted C6-C30 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. In the structural formulas A1 to A45, Sub １ ~Sub ４ The luminescent material of claim 4 , wherein each of the is independently hydrogen, deuterium, a halogen group, or a cyano group.

6. In the above formula 2, R １７ and R １８ are each independently a cyano group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, or a substituted or unsubstituted -NR ａ R ｂ and R ａ and R ｂ are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group, or a substituted or unsubstituted C3-C30 heteroaryl group; R ａ and R ｂ Optionally, together with the nitrogen to which they are attached, form a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heteroaryl group.

7. In the above formula 2, R １７ and R １８ The luminescent material according to claim 1, wherein the triazine group substituted with is represented by any one of the structural formulas B1 to B13, B50 and B51: In the structural formulas B1 to B13, B50 and B51, R １１ and R １２ are each independently hydrogen, deuterium, or a substituted or unsubstituted C1-C2 alkyl group; Sub ５ and Sub ６ are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C9 alkyloxy group, a substituted or unsubstituted -NR ｅ R ｆ , 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, a substituted or unsubstituted sulfone group, a substituted or unsubstituted C5-C30 arylthio group, a substituted or unsubstituted C5-C30 aryloxy group, a substituted or unsubstituted C5-C30 arylamine group, or a substituted or unsubstituted C5-C30 aralkyl group; ５ and Sub ６ are, independently of each other, optionally fused to the entity to which they are attached to form a substituted or unsubstituted ring group, or a substituted or unsubstituted aryl group; R ｅ and R ｆ are each independently selected from the group consisting of a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C6-C30 aralkyl group, and a substituted or unsubstituted C3-C30 heteroaryl group; R ｅ and R ｆ optionally, together with the nitrogen to which they are attached, form a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted heteroaryl group.

8. In the above formula 2, R １７ and R １８ The luminescent material according to claim 1, wherein the triazine group substituted with is represented by any one of the structural formulas B8 to B12, B50 and B51: In the structural formulas B8 to B12, B50 and B51, R １１ and R １２ are each independently hydrogen, deuterium, or a substituted or unsubstituted C1-C2 alkyl group; Sub ５ and Sub ６ are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C9 alkyloxy 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, a substituted or unsubstituted sulfone group, a substituted or unsubstituted C5-C30 arylthio group, a substituted or unsubstituted C5-C30 aryloxy group, a substituted or unsubstituted C5-C30 arylamine group, or a substituted or unsubstituted C5-C30 aralkyl group; ５ and Sub ６ are, independently of each other, selectively fused to the entity to which they are attached to form a substituted or unsubstituted ring group, or a substituted or unsubstituted aryl group.

9. In the above formula 2, R １７ and R １８ The luminescent material according to claim 1, wherein the triazine group substituted with is represented by any one of the structural formulas B12 and B50 to B54: In the structural formulas B12 and B50 to B54, Sub ５ ~Sub ８ are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group.

10. In the above formula 2, R ２２ ~R ２５ The luminescent material of claim 1 , wherein, independently of each other, are hydrogen or deuterium.

11. The luminescent material according to claim 1, wherein the luminescent material represented by the chemical formula 2 is any one of the following compounds 93 to 122:

12. A first electrode; a second electrode facing the first electrode; an intermediate layer disposed between the first electrode and the second electrode and including a light-emitting layer; A light-emitting device comprising a light-emitting material represented by the following Chemical Formula 2: [Chemical formula 2] In the above Chemical Formula 2, R １ and R ２ are each independently a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C6-C30 aralkyl group, or a substituted or unsubstituted C3-C30 heteroaryl group; R １ and R ２ optionally, together with the nitrogen to which they are attached, form a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heteroaryl group; R １７ and R １８ are each independently a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C30 alkyloxy group, a substituted or unsubstituted C3-C30 aryloxy group, a C1-C9 alkylsilyl group, or a substituted or unsubstituted -NR ａ R ｂ and R ａ and R ｂ are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group, or a substituted or unsubstituted C3-C30 heteroaryl group; R ａ and R ｂ optionally, together with the nitrogen to which they are attached, form a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heteroaryl group; R ２２ ~R ２５ are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted C4-C6 aryl group, or a substituted or unsubstituted C1-C3 alkyl group; Here, R １ , R ２ , R １７ and R １８ At least one selected from contains deuterium, or R ２２ ~R ２５ At least one selected from is deuterium.

13. The light-emitting device according to claim 12 , wherein the light-emitting layer comprises a light-emitting material represented by Chemical Formula 2.

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

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

16. a first capping layer disposed on an outer side of the first electrode; a second capping layer disposed on an outer side of the second electrode, The light emitting device of claim 12 , wherein the first capping layer or the second capping layer comprises the luminescent material represented by Chemical Formula 2.

17. An electronic device comprising the light-emitting element according to claim 12.

18. a thin film transistor electrically connected to the light emitting device; 20. The electronic device of claim 17, further comprising a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.

19. An electronic device comprising the light-emitting device according to claim 12.

20. 20. The electronic device of claim 19, wherein the electronic device is a flat panel display, a curved display, a computer monitor, a medical monitor, a television, an advertising board, an interior or exterior lighting and / or signaling 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 telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a 3D display, a virtual reality or augmented reality display, a vehicle, a video wall including tiled multiple displays, a theater or stadium screen, a phototherapy device, or a sign.

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