Light-emitting element, fused polycyclic compound for light-emitting element, and display device including light-emitting element

Abstract

Embodiments provide a fused polycyclic compound, a light-emitting element including the fused polycyclic compound, and a display device including the light-emitting element. The light emitting element includes a first electrode, a second electrode disposed on the first electrode, and an emission layer disposed between the first electrode and the second electrode. The emission layer includes a fused polycyclic compound represented by Formula 1 and explained in the specification. [Formula 1] # imgabs0 #

Description

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0092717 filed in the Korean Intellectual Property Office on July 17, 2023, the entire contents of which are incorporated herein by reference. Technical Field

[0002] Disclosed are a light-emitting element, a condensed polycyclic compound used for the light-emitting element, and a display device including the light-emitting element. Background Art

[0003] Active development of organic electroluminescent displays as image displays continues. The organic electroluminescent display is different from a liquid crystal display and is a so-called self-luminous display in which holes and electrons injected from the first electrode and the second electrode are recombined in the emission layer so that the light-emitting material including the organic compound in the emission layer emits light to achieve display.

[0004] When organic electroluminescent devices are applied to displays, it is necessary to reduce driving voltage and increase emission efficiency and lifetime of the organic electroluminescent devices, and materials for organic electroluminescent devices that can stably achieve these characteristics need to be continuously developed.

[0005] In order to realize high-efficiency organic electroluminescent devices, phosphorescence emission technology using triplet energy or fluorescence emission technology using the phenomenon of generating singlet excitons by collision of triplet excitons (triplet-triplet annihilation, TTA) is being developed. Development currently involves thermally activated delayed fluorescence (TADF) materials using the delayed fluorescence phenomenon.

[0006] It will be understood that this background section is intended, in part, to provide a useful background for understanding the technology. However, this background section may also include ideas, concepts or realizations that are not part of what was known or understood by a person skilled in the relevant art prior to the corresponding effective filing date of the subject matter disclosed herein. Summary of the invention

[0007] Disclosed is a light emitting element having improved emission efficiency and element lifetime.

[0008] Disclosed is a fused polycyclic compound that can improve the emission efficiency and device life of a light-emitting device.

[0009] Disclosed is a display device having excellent display quality by including a light emitting element having improved emission efficiency and lifetime.

[0010] The embodiment provides a light emitting element, which may include a first electrode, a second electrode disposed on the first electrode, and an emission layer disposed between the first electrode and the second electrode and including a first compound represented by Formula 1.

[0011] [Formula 1]

[0012]

[0013] In formula 1, R 1 To R 10 each independently may be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

[0014] In addition to R a1 To R a3 At least one of them may be independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

[0015] R a1 To R a3 each independently may be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

[0016] R b , R 11 and R 12 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and may be optionally combined with adjacent groups to form a ring,

[0017] Ar 1 It may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and m1, n1 and n2 may each independently be an integer of 0 to 4.

[0018] In an embodiment, the first compound may be represented by one of Formula 2-1 to Formula 2-3.

[0019] [Formula 2-1]

[0020]

[0021] [Formula 2-2]

[0022]

[0023] [Formula 2-3]

[0024]

[0025] In Formula 2-1 to Formula 2-3, Y 1 To Y 3 Each may independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0026] In Formula 2-1 to Formula 2-3, Ar 1 , R 1 To R 12 , R a1 To R a3 , R b , m1, n1 and n2 may be the same as defined in Formula 1.

[0027] In an embodiment, the first compound may be represented by Formula 3.

[0028] [Formula 3]

[0029]

[0030] In formula 3, in addition to R b1 To R b4 At least one of them may be independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

[0031] R b1 To R b4Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and may be optionally combined with adjacent groups to form a ring.

[0032] In formula 3, Ar 1 , R 1 To R 12 , R a1 To R a3 , n1 and n2 may be the same as defined in Formula 1.

[0033] In an embodiment, the first compound may be represented by Formula 4-1 or Formula 4-2.

[0034] [Formula 4-1]

[0035]

[0036] [Formula 4-2]

[0037]

[0038] In Formula 4-1 and Formula 4-2, R c1 To R c3 , R d , R e , R f and R g1 To R g3 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and may be optionally combined with adjacent groups to form a ring,

[0039] m2 may be an integer from 0 to 4, and m3 and m4 may each independently be an integer from 0 to 5, and

[0040] Among them, in formula 4-1, R c1 To R c3 At least one of them may be each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0041] In Formula 4-1 and Formula 4-2, R 1 To R 12 , R a1 To R a3 , R b , m1, n1 and n2 may be the same as defined in Formula 1.

[0042] In an embodiment, the first compound may be represented by Formula 5.

[0043] [Formula 5]

[0044]

[0045] In formula 5, except for Z 1 To Z 5 At least one of them may be independently a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms or a group represented by one of Formula A-1 to Formula A-5,

[0046] Z 1 To Z 5 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms.

[0047] [Formula A-1]

[0048]

[0049] [Formula A-2]

[0050]

[0051] [Formula A-3]

[0052]

[0053] [Formula A-4]

[0054]

[0055] [Formula A-5]

[0056]

[0057] In Formula A-1 to Formula A-5, X 1 Can be O, S, Se, N (Q 11 ) or C(Q 12 )(Q 13); and Q 1 To Q 13 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

[0058] m11 to m13 and m18 to m20 may each independently be an integer from 0 to 5; m14, m15, and m17 may each independently be an integer from 0 to 4; and m16 may be an integer from 0 to 3.

[0059] In formula 5, Ar 1 , R 1 To R 3 , R 8 , R 10 To R 12 , R a1 To R a3 , R b , m1, n1 and n2 may be the same as defined in Formula 1.

[0060] In an embodiment, Z 1 To Z 5 At least one of them may be independently a group selected from Substituent Group 1.

[0061] [Substituent Group 1]

[0062]

[0063]

[0064]

[0065]

[0066] In an embodiment, the first compound may be represented by Formula 6-1 or Formula 6-2.

[0067] [Formula 6-1]

[0068]

[0069] [Formula 6-2]

[0070]

[0071] In equation 6-1 and equation 6-2, A 1a and A 1bA may be independently cyano, substituted or unsubstituted amine, substituted or unsubstituted silyl, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms; 2 It may be a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms; B 1 To B 8 and C 1 To C 8 can each independently be a hydrogen atom or a deuterium atom; and Ar 1a It may be a group represented by Formula B-1 or Formula B-2.

[0072] [Formula B-1]

[0073]

[0074] [Formula B-2]

[0075]

[0076] In Formula B-1 and Formula B-2, R c1 To R c3 , R d , R e , R f and R g1 To R g3 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and may be optionally combined with adjacent groups to form a ring,

[0077] m2 may be an integer from 0 to 4; and m3 and m4 may each independently be an integer from 0 to 5,

[0078] Among them, in formula B-1, R c1 To R c3 At least one of them may be each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0079] In equations 6-1 and 6-2, R 11 , R 12 , R a1 To Ra3 , R b , m1, n1 and n2 may be the same as defined in Formula 1.

[0080] In an embodiment, the first compound may be represented by Formula 7-1 or Formula 7-2.

[0081] [Formula 7-1]

[0082]

[0083] [Formula 7-2]

[0084]

[0085] In equations 7-1 and 7-2, R 13 , R 14 , R c1 To R c3 and R d They may all independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and may optionally be combined with adjacent groups to form a ring; and n13, n14 and m2 may all independently be integers from 0 to 4.

[0086] In Formula 7-1 and Formula 7-2, Ar 1 , R 1 To R 5 , R 7 To R 12 , R a1 To R a3 , R b , m1, n1 and n2 may be the same as defined in Formula 1.

[0087] In an embodiment, the emission layer may further include at least one of a second compound represented by Formula HT-1, a third compound represented by Formula ET-1, and a fourth compound represented by Formula D-1.

[0088] [Formula HT-1]

[0089]

[0090] In formula HT-1, M 1 To M 8 can be independently N or C (R 51 );L 1Y may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms; a Can be a direct key, C(R 52 )(R 53 ) or Si(R 54 )(R 55 );Ar a may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and

[0091] R 51 To R 55 Each of them may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms, and may be optionally combined with adjacent groups to form a ring.

[0092] [Formula ET-1]

[0093]

[0094] In formula ET-1, Z a To Z c At least one of them can be N; Z a To Z c The rest of the parts in may be independently C(R 56 );R 56 It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring carbon atoms; b1 to b3 may each independently be an integer of 0 to 10,

[0095] Ar b To Ar d L and L may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms; and L 2 To L 4 Each of them may independently be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0096] [Formula D-1]

[0097]

[0098] In formula D-1, Q 1 To Q 4 may be independently C or N; C1 to C4 may be independently a substituted or unsubstituted hydrocarbon ring of 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring of 2 to 30 ring carbon atoms; L 11 To L 13 Can be directly connected, *-O-*, *-S-*, a substituted or unsubstituted alkylene group of 1 to 20 carbon atoms, a substituted or unsubstituted arylene group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring carbon atoms; b11 to b13 may all independently be 0 or 1; R 61 To R 66 Each of d1 to d4 is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted sulfenyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms; and d1 to d4 are each independently an integer from 0 to 4.

[0099] An embodiment provides a display device, which may include: a circuit layer, which is arranged on a substrate layer; and a display device layer, which is arranged on the circuit layer and includes a light-emitting element, wherein the light-emitting element may include a first electrode, a second electrode arranged on the first electrode, and an emission layer arranged between the first electrode and the second electrode and including a first compound represented by Formula 1.

[0100] [Formula 1]

[0101]

[0102] In formula 1, R 1 To R 10 each independently may be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

[0103] In addition to Ra1 To R a3 At least one of them may be independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

[0104] R a1 To R a3 each independently may be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

[0105] R b , R 11 and R 12 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and may be optionally combined with adjacent groups to form a ring,

[0106] Ar 1 It may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and m1, n1 and n2 may each independently be an integer of 0 to 4.

[0107] In an embodiment, the light emitting element may further include a capping layer disposed on the second electrode; and a refractive index of the capping layer with respect to light in a wavelength range of about 550 nm to about 660 nm may be greater than or equal to about 1.6.

[0108] In an embodiment, the display device may further include a light control layer, which is arranged on the display device layer and includes quantum dots. The light-emitting element can emit a first color light, and the light control layer may include: a first light control unit, including a first quantum dot that converts the first color light into a second color light, and the second color light is in a wavelength region larger than the first color light; a second light control unit, including a second quantum dot that converts the first color light into a third color light, and the third color light is in a wavelength region larger than the first color light and the second color light; and a third light control unit that transmits the first color light.

[0109] In an embodiment, the display device may further include a color filter layer disposed on the light control layer, and the color filter layer may include: a first filter transmitting the second color light; a second filter transmitting the third color light; and a third filter transmitting the first color light.

[0110] The embodiments provide fused polycyclic compounds which may be represented by Formula 1 explained herein.

[0111] In an embodiment, the fused polycyclic compound may be represented by Formula 4-1 or Formula 4-2 explained herein.

[0112] In an embodiment, the fused polycyclic compound may be represented by Formula 5 explained herein.

[0113] In an embodiment, the fused polycyclic compound may be represented by Formula 6-1 or Formula 6-2 explained herein.

[0114] In an embodiment, the fused polycyclic compound may be represented by Formula 7-1 or Formula 7-2 explained herein.

[0115] In an embodiment, R 1 To R 10 At least one of may each independently be a group selected from Substituent Group 1 explained herein.

[0116] In an embodiment, the condensed polycyclic compound may be selected from Compound Group 1 explained below.

[0117] It will be understood that the above embodiments have been described in a generic and illustrative sense only and not for purposes of limitation, and that the disclosure is not limited to the above embodiments. BRIEF DESCRIPTION OF THE DRAWINGS

[0118] The accompanying drawings are included to provide a further understanding of the embodiments, and are incorporated into and constitute a part of this specification. The accompanying drawings illustrate the disclosed embodiments and their principles. The above and other aspects and features of the disclosure will become more apparent by describing the disclosed embodiments in detail with reference to the accompanying drawings, in which:

[0119] Figure 1 is a schematic plan view of a display device according to an embodiment;

[0120] Figure 2 is a schematic cross-sectional view of a display device according to an embodiment;

[0121] Figure 3 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0122] Figure 4 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0123] Figure 5 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0124] Figure 6 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0125] Figure 7 and Figure 8 are schematic cross-sectional views of display devices according to embodiments;

[0126] Fig. 9 is a schematic cross-sectional view of a display device according to an embodiment;

[0127] Fig.10 is a schematic cross-sectional view of a display device according to an embodiment; and

[0128] Fig.11 is a schematic perspective view of a car in which a display device is provided according to an embodiment. DETAILED DESCRIPTION

[0129] The disclosure will now be described more fully hereinafter with reference to the accompanying drawings, in which embodiments are shown. However, the disclosure may be implemented in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that the disclosure will be thorough and complete and will fully convey the scope of the disclosure to those skilled in the art.

[0130] In the drawings, the size, thickness, ratio, and dimensions of elements may be exaggerated for ease of description and clarity. The same reference numerals and / or the same reference signs refer to the same elements throughout.

[0131] In the description, it will be understood that when an element (or region, layer, portion, etc.) is referred to as being "on," "connected to," or "coupled to" another element, the element may be directly on, directly connected to, or directly coupled to the other element, or one or more intervening elements may be present between the element and the other element. In a similar sense, when an element (or region, layer, portion, etc.) is described as "covering" another element, the element may directly cover the other element, or one or more intervening elements may be present between the element and the other element.

[0132] In the description, when an element is "directly on," "directly connected to," or "directly coupled to" another element, there are no intervening elements. For example, "directly on" may mean that two layers or two elements are disposed without an additional element (such as an adhesive element) therebetween.

[0133] As used herein, expressions used in the singular such as “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.

[0134] As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. For example, "A and / or B" may be understood to mean "A, B, or A and B". The terms "and" and "or" may be used in either a conjunctive or disjunctive sense and may be understood to be equivalent to "and / or".

[0135] In the specification and claims, for the purpose of its meaning and interpretation, the term "at least one of..." is intended to include the meaning of "at least one selected from the group consisting of..." For example, "at least one of A, B, and C" may be understood to mean only A, only B, only C, or any combination of two or more of A, B, and C (such as ABC, ACC, BC, or CC). When the term "at least one of..." follows a list of elements, it modifies the entire list of elements and does not modify the individual elements of the list.

[0136] It will be understood that, although the terms first, second, etc. can be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Therefore, without departing from the disclosed teachings, the first element can be referred to as the second element. Similarly, without departing from the disclosed scope, the second element can be referred to as the first element.

[0137] For ease of description, spatially relative terms "below," "under," "below," "above," "on," etc. may be used herein to describe the relationship between one element or component and another element or component as shown in the drawings. It will be understood that, in addition to the orientation depicted in the drawings, the spatially relative terms are intended to cover different orientations of the device in use or operation. For example, in the case where the device shown in the drawings is flipped, a device that is "below" or "below" another device may be placed "above" the other device. Therefore, the illustrative term "below" may include both a lower position and an upper position. The device may also be positioned in other directions, so the spatially relative terms may be interpreted differently depending on the orientation.

[0138] As used herein, the term "about" or "approximately" includes the stated value and means within an acceptable range of deviation of the recited value as determined by one of ordinary skill in the art, taking into account the measurement in question and the errors associated with the measurement of the recited quantity (e.g., limitations of the measurement system). For example, "about" can mean within one or more standard deviations, or within ±20%, ±10%, or ±5% of the recited value.

[0139] It should be understood that the terms "comprises," "having," "including" and variations thereof are intended to indicate the presence of stated features, integers, steps, operations, elements, components or combinations thereof in the disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components or combinations thereof.

[0140] Unless otherwise defined or implied herein, all terms (including technical and scientific terms) used have the same meaning as those commonly understood by those skilled in the art to which the present disclosure belongs. It will also be understood that terms (such as those defined in commonly used dictionaries) should be interpreted as having a meaning consistent with their meaning in the context of the relevant art, and should not be interpreted in an idealized or overly formalized meaning unless clearly defined in the specification.

[0141] In the specification, the term "substituted or unsubstituted" can describe a group that is unsubstituted or substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, an amine group, a silyl group, an oxy group, a sulfenyl group, a sulfonyl group, a carbonyl group, a boron group, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkynyl group, a hydrocarbon ring group, an aryl group, and a heterocyclic group. Each of the substituents listed above can itself be substituted or unsubstituted. For example, a biphenyl group can be interpreted as an aryl group, or it can be interpreted as a phenyl group substituted with a phenyl group.

[0142] In the specification, the phrase "bonded to an adjacent group to form a ring" may be interpreted as a group bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. The hydrocarbon ring may be aliphatic or aromatic. The heterocyclic ring may be aliphatic or aromatic. The hydrocarbon ring and the heterocyclic ring may each independently be monocyclic or polycyclic. The ring formed by the adjacent groups bonded to each other may itself be connected to another ring to form a spiro structure.

[0143] In the specification, the term "adjacent group" may be interpreted as a substituent that replaces an atom directly connected to an atom substituted with a corresponding substituent, another substituent that replaces an atom substituted with a corresponding substituent, or a substituent that is spatially located at the closest position to the corresponding substituent. For example, the two methyl groups in 1,2-dimethylbenzene may be interpreted as "adjacent groups" to each other, and the two ethyl groups in 1,1-diethylcyclopentane may be interpreted as "adjacent groups" to each other. For example, the two methyl groups in 4,5-dimethylphenanthrene may be interpreted as "adjacent groups" to each other.

[0144] In the specification, examples of the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0145] In the specification, the alkyl group may be linear or branched. The carbon number in the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of the alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-decyl The invention also includes but is not limited to alkyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heonicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, and the like, but the embodiments are not limited thereto.

[0146] In the specification, the cycloalkyl group may be a cyclic alkyl group. The carbon number in the cycloalkyl group may be 3 to 50, 3 to 30, 3 to 20, or 3 to 10. Examples of cycloalkyl groups may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, 1-adamantyl, 2-adamantyl, isobornyl, bicycloheptyl, etc., but embodiments are not limited thereto.

[0147] In the specification, alkenyl can be a hydrocarbon group including at least one carbon-carbon double bond in the middle or at the end of an alkyl group having 2 or more carbon atoms. The alkenyl can be linear or branched. The number of carbon atoms in the alkenyl is not particularly limited, but can be 2 to 30, 2 to 20 or 2 to 10. Examples of alkenyl can include vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl, styrylvinyl, etc., but embodiments are not limited thereto.

[0148] In the specification, alkynyl can be a hydrocarbon group including at least one carbon-carbon triple bond in the middle or at the end of an alkyl group having 2 or more carbon atoms. Alkynyl can be straight chain or branched. Although the number of carbon atoms is not particularly limited, it can be 2 to 30, 2 to 20 or 2 to 10. Examples of alkynyl can include ethynyl, propynyl, etc., but are not limited thereto.

[0149] In the specification, the hydrocarbon ring group may be any functional group or substituent derived from an aliphatic hydrocarbon ring. The hydrocarbon ring group may be a saturated hydrocarbon ring group having 5 to 20 ring-forming carbon atoms.

[0150] In the specification, an aryl group may be any functional group or substituent derived from an aromatic hydrocarbon ring. An aryl group may be monocyclic or polycyclic. The number of ring carbon atoms in the aryl group may be 6 to 60, 6 to 50, 6 to 40, 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentaphenyl, hexaphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Base, etc., but the embodiment is not limited thereto.

[0151] In the specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. Examples of the substituted fluorenyl group are as follows, but the embodiment is not limited thereto.

[0152]

[0153] In the specification, the heterocyclic group herein can be any functional group or substituent derived from a ring containing at least one of B, O, N, P, Si, S and Se as a heteroatom. The heterocyclic group can be aliphatic or aromatic. The aromatic heterocyclic group can be a heteroaryl. The aliphatic heterocycle and the aromatic heterocycle can each independently be monocyclic or polycyclic.

[0154] In the specification, the heterocyclic group may contain at least one of B, O, N, P, Si, Se and S as a heteroatom. If the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heterocyclic group may be monocyclic or polycyclic, and the heterocyclic group may be a heteroaryl. The number of ring carbon atoms in the heterocyclic group may be 2 to 60, 2 to 50, 2 to 40, 2 to 30, 2 to 20 or 2 to 10.

[0155] In the specification, the aliphatic heterocyclic group may include at least one of B, O, N, P, Si, Se, and S as a heteroatom. The number of ring carbon atoms in the aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of the aliphatic heterocyclic group may include an oxirane group, an oxirane group, a pyrrolidinyl group, a piperidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, a thiol group, a tetrahydropyranyl group, a 1,4-dioxanyl group, and the like, but the embodiment is not limited thereto.

[0156] In the specification, the heteroaryl group may contain at least one of B, O, N, P, Si, Se and S as a heteroatom. If the heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heteroaryl group may be monocyclic or polycyclic. The number of ring carbon atoms in the heteroaryl group may be 2 to 60, 2 to 50, 2 to 40, 2 to 30, 2 to 20 or 2 to 10. Examples of heteroaryl groups may include thienyl, furanyl, pyrrolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazine, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothiphenyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiadiazolyl, phenothiazinyl, dibenzothirolyl, dibenzofuranyl, and the like, but embodiments are not limited thereto.

[0157] In the specification, the above description of the aryl group may be applied to the arylene group, except that the arylene group may be a divalent group. The above description of the heteroaryl group may be applied to the heteroarylene group, except that the heteroarylene group may be a divalent group.

[0158] In the specification, the silyl group may be an alkylsilyl group or an arylsilyl group. Examples of the silyl group may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but the embodiment is not limited thereto.

[0159] In the specification, the number of carbon atoms in the carbonyl group is not particularly limited, but may be 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group may have one of the following structures, but the embodiment is not limited thereto.

[0160]

[0161] In the specification, the number of carbon atoms in the sulfinyl group and the sulfonyl group is not particularly limited, but may be 1 to 30. The sulfinyl group may include an alkylsulfinyl group or an arylsulfinyl group. The sulfonyl group may include an alkylsulfonyl group or an arylsulfonyl group.

[0162] In the specification, the thio group may include an alkylthio group or an arylthio group. The thio group may be a sulfur atom bonded to an alkyl group or an aryl group as defined above. Examples of the thio group may include a methylthio group, an ethylthio group, a propylthio group, a pentylthio group, a hexylthio group, an octylthio group, a dodecylthio group, a cyclopentylthio group, a cyclohexylthio group, a phenylthio group, a naphthylthio group, but the embodiment is not limited thereto.

[0163] In the specification, the oxy group may be an oxygen atom bonded to an alkyl group or an aryl group as defined above. The oxy group may be an alkoxy group or an aryloxy group. The alkoxy group may be linear, branched or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. Examples of oxy groups may include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, etc., but embodiments are not limited thereto.

[0164] In the specification, a boryl group may be a boron atom bonded to an alkyl group or an aryl group as defined above. A boryl group may be an alkyl boryl group or an aryl boryl group. Examples of boryl groups may include dimethyl boryl group, methyl boryl group, tert-butyl methyl boryl group, diphenyl boryl group, phenyl boryl group, etc., but embodiments are not limited thereto.

[0165] In the specification, the number of carbon atoms in the amine group is not particularly limited, but can be 1 to 30. The amine group may include an alkylamine group or an arylamine group. Examples of the amine group may include methylamine group, dimethylamine group, anilino group, diphenylamine group, naphthylamine group, 9-methyl-anthrylamine group, etc., but the embodiment is not limited thereto.

[0166] In the specification, the alkyl group in the alkoxy group, the alkylthio group, the alkylsulfinyl group, the alkylsulfonyl group, the alkylaryl group, the alkylamino group, the alkylboryl group, the alkylsilyl group or the alkylamine group may be the same as the examples of the alkyl group described above.

[0167] In the specification, the aryl group in the aryloxy group, the arylthio group, the arylsulfinyl group, the arylsulfonyl group, the arylamino group, the arylboryl group, the arylsilyl group or the arylamine group may be the same as exemplified in the above-mentioned aryl group.

[0168] In the specification, a direct key may be a single key.

[0169] In this manual, the symbol and “-*” both indicate the binding site with the adjacent atom.

[0170] Hereinafter, embodiments will be described with reference to the accompanying drawings.

[0171] Figure 1 is a schematic plan view showing an example of a display device DD. Figure 2 is a schematic cross-sectional view of a display device DD according to the embodiment. Figure 2 It is shown along Figure 1 A schematic cross-sectional view of a portion taken along line II'.

[0172] The display device DD may include a display panel DP and an optical layer PP disposed on the display panel DP on a third direction axis DR3. The display panel DP includes light emitting elements ED-1, ED-2, and ED-3. The display device DD may include each of a plurality of light emitting elements ED-1, ED-2, and ED-3. The optical layer PP may be disposed on the display panel DP to control light reflected from external light at the display panel DP. The optical layer PP may include, for example, a polarizing layer or a color filter layer. Although not shown in the drawings, in an embodiment, the optical layer PP may be omitted from the display device DD.

[0173] The base substrate BL may be disposed on the optical layer PP. The base substrate BL may provide a base surface on which the optical layer PP is disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiment is not limited thereto, and the base substrate BL may include an inorganic layer, an organic layer, or a composite material layer. Although not shown in the drawings, in an embodiment, the base substrate BL may be omitted.

[0174] The display device DD according to the embodiment may further include a filling layer (not shown). The filling layer (not shown) may be disposed between the display device layer DP-ED and the base substrate BL. The filling layer (not shown) may be an organic material layer. The filling layer (not shown) may include at least one of an acrylic resin, a siloxane resin, and an epoxy resin.

[0175] The display panel DP may include a base layer BS, a circuit layer DP-CL disposed on the base layer BS, and a display device layer DP-ED. The display device layer DP-ED may include a pixel defining film PDL, light emitting elements ED-1, ED-2, and ED-3 disposed between portions of the pixel defining film PDL, and an encapsulation layer TFE disposed on the light emitting elements ED-1, ED-2, and ED-3.

[0176] The base layer BS may provide a base surface on which the display device layer DP-ED is disposed. The base layer BS may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiment is not limited thereto, and the base layer BS may be an inorganic layer, an organic layer, or a composite material layer.

[0177] In an embodiment, the circuit layer DP-CL is disposed on the base layer BS, and the circuit layer DP-CL may include transistors (not shown). Each of the transistors (not shown) may include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-CL may include a switching transistor and a driving transistor for driving the light emitting elements ED-1, ED-2, and ED-3 of the display device layer DP-ED.

[0178] The light emitting elements ED-1, ED-2 and ED-3 may each have a configuration according to the method described later. Figures 3 to 6 The light emitting elements ED-1, ED-2 and ED-3 may each include a first electrode EL1, a hole transport region HTR, an emission layer EML-R, EML-G or EML-B, an electron transport region ETR and a second electrode EL2.

[0179] Figure 2 An embodiment is shown in which the emission layers EML-R, EML-G, and EML-B of the light emitting elements ED-1, ED-2, and ED-3 are disposed in the opening OH defined in the pixel defining film PDL, and the hole transport region HTR, the electron transport region ETR, and the second electrode EL2 are all disposed as a common layer for all of the light emitting elements ED-1, ED-2, and ED-3. However, the embodiment is not limited thereto. Although Figure 2Although not shown in the figure, in an embodiment, the hole transport region HTR and the electron transport region ETR may be provided by being patterned inside the opening OH defined in the pixel defining film PDL. For example, in an embodiment, the hole transport region HTR, the emission layers EML-R, EML-G and EML-B, and the electron transport region ETR of the light emitting elements ED-1, ED-2, and ED-3 may be provided by being patterned by an inkjet printing method.

[0180] The encapsulation layer TFE may cover the light emitting elements ED-1, ED-2 and ED-3. The encapsulation layer TFE may seal the light emitting elements ED-1, ED-2 and ED-3. The encapsulation layer TFE may be a thin film encapsulation layer. The encapsulation layer TFE may be formed by stacking a single layer or a plurality of layers. The encapsulation layer TFE may include at least one insulating layer. The encapsulation layer TFE according to the embodiment may include at least one inorganic film (hereinafter, encapsulation-inorganic film). The encapsulation layer TFE according to the embodiment may also include at least one organic film (hereinafter, encapsulation-organic film) and at least one encapsulation-inorganic film.

[0181] The encapsulation-inorganic film may protect the light-emitting elements ED-1, ED-2, and ED-3 from moisture and / or oxygen, and the encapsulation-organic film may protect the light-emitting elements ED-1, ED-2, and ED-3 from foreign matter (such as dust particles). The encapsulation-inorganic film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, aluminum oxide, etc., but the embodiment is not particularly limited thereto. The encapsulation-organic film may include an acrylic compound, an epoxy compound, etc. The encapsulation-organic film may include a photopolymerizable organic material, but the embodiment is not particularly limited thereto.

[0182] The encapsulation layer TFE may be disposed on the second electrode EL2 , and may be disposed to fill the opening OH.

[0183] Reference Figure 1 and Figure 2 , the display device DD may include a non-light emitting area NPXA and light emitting areas PXA-R, PXA-G, and PXA-B. The light emitting areas PXA-R, PXA-G, and PXA-B may each be an area that emits light generated by the light emitting elements ED-1, ED-2, and ED-3. In a plan view, the light emitting areas PXA-R, PXA-G, and PXA-B may be spaced apart from each other.

[0184] The light-emitting regions PXA-R, PXA-G, and PXA-B may all be regions separated by a pixel-defining film PDL. The non-light-emitting region NPXA may be a region between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B, which corresponds to the pixel-defining film PDL. In an embodiment, the light-emitting regions PXA-R, PXA-G, and PXA-B may correspond to pixels. The pixel-defining film PDL may separate the light-emitting elements ED-1, ED-2, and ED-3. The emission layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 may be disposed in an opening OH defined in the pixel-defining film PDL and separated from each other.

[0185] The light emitting regions PXA-R, PXA-G, and PXA-B may be arranged into a plurality of groups according to the colors of the lights generated from the light emitting elements ED-1, ED-2, and ED-3. Figure 1 and Figure 2 In the display device DD of the embodiment shown in , three light emitting regions PXA-R, PXA-G and PXA-B emitting red light, green light and blue light respectively are shown as examples. For example, the display device DD may include a red light emitting region PXA-R, a green light emitting region PXA-G and a blue light emitting region PXA-B separated from each other.

[0186] In the display device DD according to the embodiment, the light emitting elements ED-1, ED-2 and ED-3 may emit light having wavelengths different from each other. For example, in the embodiment, the display device DD may include a first light emitting element ED-1 emitting red light, a second light emitting element ED-2 emitting green light, and a third light emitting element ED-3 emitting blue light. For example, the red light emitting region PXA-R, the green light emitting region PXA-G, and the blue light emitting region PXA-B of the display device DD may correspond to the first light emitting element ED-1, the second light emitting element ED-2, and the third light emitting element ED-3, respectively.

[0187] However, the embodiment is not limited thereto, and the first to third light emitting elements ED-1, ED-2, and ED-3 may emit light in the same wavelength range, or at least one light emitting element may emit light in a wavelength range different from that of the other light emitting elements. For example, the first to third light emitting elements ED-1, ED-2, and ED-3 may all emit blue light.

[0188] The light emitting regions PXA-R, PXA-G, and PXA-B in the display device DD according to the embodiment may be arranged in a stripe configuration. Figure 1, the red light emitting region PXA-R, the green light emitting region PXA-G, and the blue light emitting region PXA-B may be arranged along the second direction axis DR2. In another embodiment, the red light emitting region PXA-R, the green light emitting region PXA-G, and the blue light emitting region PXA-B may be arranged in this repeating order along the first direction axis DR1.

[0189] Figure 1 and Figure 2 It is shown that the light emitting regions PXA-R, PXA-G, and PXA-B have similar areas to each other, but the embodiment is not limited thereto. Therefore, the light emitting regions PXA-R, PXA-G, and PXA-B may be different in size or shape from each other according to the wavelength range of the emitted light. The areas of the light emitting regions PXA-R, PXA-G, and PXA-B may be areas in a plane view defined by the first direction axis DR1 and the second direction axis DR2.

[0190] The arrangement of the light emitting regions PXA-R, PXA-G and PXA-B is not limited to Figure 1 , and the order of arranging the red light emitting area PXA-R, the green light emitting area PXA-G, and the blue light emitting area PXA-B may be provided in various combinations according to the display quality characteristics required in the display device DD. For example, the light emitting areas PXA-R, PXA-G, and PXA-B may be arranged in a pentile configuration (such as ) or in a diamond shape (such as Diamond )arrangement.

[0191] The areas of the light emitting regions PXA-R, PXA-G, and PXA-B may be different in size from each other. For example, in an embodiment, the area of ​​the green light emitting region PXA-G may be smaller than the area of ​​the blue light emitting region PXA-B, but the embodiment is not limited thereto.

[0192] In the following, Figures 3 to 6 1 and 2 are schematic cross-sectional views of a light emitting element ED according to an embodiment. The light emitting element ED according to the embodiment may include a first electrode EL1, a second electrode EL2 disposed opposite to the first electrode EL1, and at least one functional layer disposed between the first electrode EL1 and the second electrode EL2. The light emitting element ED according to the embodiment may include a fused polycyclic compound to be explained later in at least one functional layer.

[0193] The light emitting element ED may include a hole transport region HTR, an emission layer EML, an electron transport region ETR, etc. stacked in sequence as at least one functional layer. Figure 3, the light emitting element ED of the embodiment may include a first electrode EL1, a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode EL2 which are sequentially stacked.

[0194] and Figure 3 compared to, Figure 4 Schematic cross-sectional view of a light emitting element ED is shown, wherein the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Figure 3 compared to, Figure 5 A schematic cross-sectional view of a light emitting element ED is shown, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL and a hole blocking layer HBL. Figure 4 compared to, Figure 6 A schematic cross-sectional view of a light emitting element ED including a cover layer CPL disposed on the second electrode EL2 is shown.

[0195] The light emitting element ED according to the embodiment may include a fused polycyclic compound to be explained later in at least one functional layer. In the light emitting element ED according to the embodiment, at least one of the hole transport region HTR, the emission layer EML, and the electron transport region ETR may include the fused polycyclic compound of the embodiment. For example, in the light emitting element ED, the emission layer EML may include a fused polycyclic compound.

[0196] The first electrode EL1 may have conductivity. The first electrode EL1 may be formed of a metal material, a metal alloy, or a conductive compound. The first electrode EL1 may be an anode or a cathode. However, the embodiment is not limited thereto. For example, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode. The first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, Zn, their oxides, their compounds, or their mixtures.

[0197] If the first electrode EL1 is a transmissive electrode, the first electrode EL1 may include a transparent metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). If the first electrode EL1 is a transflective electrode or a reflective electrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, a compound thereof, a mixture thereof (e.g., a mixture of Ag and Mg), or a material having a multilayer structure such as LiF / Ca (a stacking structure of LiF and Ca), LiF / Al (a stacking structure of LiF and Al). In an embodiment, the first electrode EL1 may have a multilayer structure including a reflective film or a transflective film formed of the above materials and a transparent conductive film formed of ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but the embodiment is not limited thereto. In an embodiment, the first electrode EL1 may include the above metal material, a combination of at least two of the above metal materials, an oxide of the above metal material, etc. The thickness of the first electrode EL1 may be about 1000 Å. to about For example, the thickness of the first electrode EL1 may be in the range of about to about within the range.

[0198] The hole transport region HTR is disposed on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, a buffer layer (not shown), an emission auxiliary layer (not shown), and an electron blocking layer EBL. The thickness of the hole transport region HTR may be, for example, about 1000 Å. to about within the range.

[0199] The hole transport region HTR may be a layer composed of a single material, a layer including different materials, or a structure including a plurality of layers including different materials.

[0200] For example, the hole transport region HTR may have a single layer structure of a hole injection layer HIL or a hole transport layer HTL, or may have a single layer structure formed of a hole injection material and a hole transport material. In other embodiments, the hole transport region HTR may have a single layer structure formed of different materials, or may have a structure in which a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / buffer layer (not shown), a hole injection layer HIL / buffer layer (not shown), a hole transport layer HTL / buffer layer (not shown), or a hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL is stacked in the order stated in their respective order from the first electrode EL1, but the embodiment is not limited thereto.

[0201] The hole transport region HTR may be formed using various methods such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and a laser induced thermal imaging (LITI) method.

[0202] The hole transport region HTR may include a compound represented by Formula H-1:

[0203] [Formula H-1]

[0204]

[0205] In formula H-1, L 1 and L 2 L may be independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. a and b may be independently an integer from 0 to 10. When a or b is 2 or more, multiple L 1 or more L 2 Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0206] In formula H-1, Ar 1 and Ar 2 and Ar may be independently substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms or substituted or unsubstituted heteroaryl groups having 2 to 30 ring carbon atoms. 3 It may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0207] In an embodiment, the compound represented by formula H-1 may be a monoamine compound. In another embodiment, the compound represented by formula H-1 may be wherein Ar1 To Ar 3 In another embodiment, the compound represented by formula H-1 may be a diamine compound wherein Ar 1 and Ar 2 At least one of the carbazole compounds includes a substituted or unsubstituted carbazole group, or wherein Ar 1 and Ar 2 At least one of the fluorene compounds includes a substituted or unsubstituted fluorenyl group.

[0208] The compound represented by Formula H-1 may be any compound selected from Compound Group H. However, the compounds listed in Compound Group H are merely examples, and the compound represented by Formula H-1 is not limited to the compounds represented by Compound Group H:

[0209] [Compound Group H]

[0210]

[0211]

[0212] The hole transport region HTR may include a phthalocyanine compound (such as copper phthalocyanine), N 1 ,N 1 '-([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 ,N 4 -dimethylphenylbenzene-1,4-diamine) (DNTPD), 4,4',4"-[tri(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-tri(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tri[N-(2-naphthyl)-N-phenylamino]triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (PA NI / DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetrakis(pentafluorophenyl)borate], dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexanitrile (HAT-CN), etc.

[0213] The hole transport region HTR may include a carbazole derivative (such as N-phenylcarbazole or polyvinylcarbazole), a fluorene derivative, a triphenylamine derivative (such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD) or 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA)), N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylene-bis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 1,3-bis(N-carbazolyl)benzene (mCP), and the like.

[0214] The hole transport region HTR may include 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), 9-phenyl-9H-3,9′-bicarbazole (CCP), 1,3-bis(1,8-dimethyl-9H-carbazole-9-yl)benzene (mDCP), or the like.

[0215] The hole transport region HTR may include the above-mentioned compound of the hole transport region HTR in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.

[0216] The thickness of the hole transport region HTR can be about to about For example, the thickness of the hole transport region HTR may be in the range of about to about When the hole transport region HTR includes the hole injection layer HIL, the hole injection layer HIL may have, for example, a thickness of about to about When the hole transport region HTR includes the hole transport layer HTL, the hole transport layer HTL may have a thickness in the range of about To date For example, when the hole transport region HTR includes the electron blocking layer EBL, the electron blocking layer EBL may have a thickness in the range of about to about If the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy the above range, satisfactory hole transport properties may be achieved without significantly increasing the driving voltage.

[0217] In addition to the above materials, the hole transport region HTR may further include a charge generating material to increase conductivity. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generating material may be, for example, a p-dopant. The p-dopant may include at least one of a halogenated metal compound, a quinone derivative, a metal oxide, and a cyano compound, but the embodiment is not limited thereto. For example, the p-dopant may include a halogenated metal compound (such as CuI or RbI), a quinone derivative (such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F 4 -TCNQ)), metal oxides (such as tungsten oxide or molybdenum oxide), cyano compounds (such as dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexanitrile (HAT-CN) or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropyl]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile (NDP9)), etc., but the embodiments are not limited thereto.

[0218] As described above, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR may further include at least one of a buffer layer (not shown) and an electron blocking layer EBL. The buffer layer (not shown) may compensate for the resonance distance according to the wavelength of light emitted from the emission layer EML, and the light emission efficiency may be increased accordingly. The material that may be included in the hole transport region HTR may be included in the buffer layer (not shown). The electron blocking layer EBL is a layer that may prevent electron injection from the electron transport region ETR to the hole transport region HTR.

[0219] The emission layer EML may be disposed on the hole transport region HTR. The emission layer EML may have, for example, approximately to about For example, the emission layer EML may have a thickness of about to about The emission layer EML may be a layer composed of a single material, a layer including different materials, or a structure including a plurality of layers including different materials.

[0220] The light emitting element ED according to the embodiment may include a fused polycyclic compound represented by Formula 1 in at least one functional layer disposed between the first electrode EL1 and the second electrode EL2. In the light emitting element ED according to the embodiment, the emission layer EML may include the fused polycyclic compound. In the embodiment, the emission layer EML may include the fused polycyclic compound as a dopant. The fused polycyclic compound according to the embodiment may be a dopant material of the emission layer EML. In the specification, the fused polycyclic compound according to the embodiment may be referred to as a first compound.

[0221] According to the embodiment, the fused polycyclic compound may include a structure in which a plurality of aromatic rings are fused via a boron atom and a nitrogen atom. According to the embodiment, the fused polycyclic compound may include a structure in which a plurality of aromatic rings are fused via a boron atom and two nitrogen atoms. According to the embodiment, the fused polycyclic compound may include a structure in which a plurality of aromatic rings are fused via a boron atom, a first nitrogen atom, and a second nitrogen atom. For example, according to the embodiment, the fused polycyclic compound may include a fused ring formed by fusing a plurality of aromatic rings via a boron atom, a first nitrogen atom, and a second nitrogen atom.

[0222] The fused polycyclic compound according to the embodiment may have a structure including the first to third aromatic rings fused together via a boron atom, a first nitrogen atom, and a second nitrogen atom. The first to third aromatic rings may be connected to the boron atom, the first aromatic ring and the third aromatic ring may be connected to each other via the first nitrogen atom, and the second aromatic ring and the third aromatic ring may be connected to each other via the second nitrogen atom. In the specification, the boron atom, the first nitrogen atom, the second nitrogen atom, and the fused structure formed by fusing the first to third aromatic rings via the boron atom, the first nitrogen atom, and the second nitrogen atom may be referred to as a "fused ring core".

[0223] In an embodiment, the first to third aromatic rings may be independently substituted or unsubstituted monocyclic aromatic hydrocarbon rings of 6 to 30 ring-forming carbon atoms. The first to third aromatic rings may be independently 6-membered aromatic hydrocarbon rings. For example, the first to third aromatic rings may be benzene rings.

[0224] The fused polycyclic compound according to the embodiment may include a first substituent connected to the fused ring core. The first substituent may be connected to the first nitrogen atom of the fused ring core. The first substituent may include a first dibenzofuran moiety and a first sub-substituent connected to the first dibenzofuran moiety. The first sub-substituent may be an aryl group of 6 to 30 ring-forming carbon atoms substituted or unsubstituted or a heteroaryl group of 2 to 30 ring-forming carbon atoms substituted or unsubstituted. The first substituent may be connected to the first nitrogen atom of the fused ring core via a carbon atom at position 4 of the first dibenzofuran moiety. The first sub-substituent may be connected to a benzene ring connected to the first nitrogen atom among the two benzene rings constituting the first dibenzofuran moiety. The carbon atom at position 4 of the first dibenzofuran moiety may be connected to the first nitrogen atom, and the first sub-substituent may be connected to at least one of the remaining carbons at positions 1 to 3. For example, the first nitrogen atom may be connected to the carbon atom at position 4 of the first dibenzofuran moiety, and the first sub-substituent may be connected to any one of the remaining carbon atoms at positions 1 to 3. In another embodiment, the first nitrogen atom can be connected to the carbon atom at the 4-position of the first dibenzofuran moiety, and the first substituent can be connected to two of the remaining carbon atoms at positions 1 to 3. In another embodiment, the first nitrogen atom can be connected to the carbon atom at the 4-position of the first dibenzofuran moiety, and the first substituent can be connected to each of the carbon atoms at positions 1 to 3. The first dibenzofuran moiety can be directly connected to the first nitrogen atom. For example, the first dibenzofuran moiety can be directly connected to the first nitrogen atom without a separate connecting portion. In the specification, the first substituent can be referred to as an "aromatic substituent".

[0225] The carbon numbering of the first dibenzofuran moiety is shown in Formula D.

[0226] [Formula D]

[0227]

[0228] Regarding the carbon numbering of the first dibenzofuran moiety, the first dibenzofuran moiety can be arranged so that the oxygen atom (O) is located at the top as in Formula D, the numbering starts in a clockwise order from the carbon atom at the meta position relative to the oxygen atom among the carbon atoms constituting the left benzene ring, and the carbon atoms at the condensation position are excluded from the numbering.

[0229] For example, the fused polycyclic compound according to the embodiment may include a second substituent connected to an aromatic ring among the aromatic rings constituting the fused ring core. The second substituent is an electron donor substituent and may include a carbazole moiety. The second substituent may be connected to the first aromatic ring. The second substituent may be connected to the first aromatic ring at a para position relative to the boron atom.

[0230] The fused polycyclic compound according to an embodiment may be represented by Formula 1.

[0231] [Formula 1]

[0232]

[0233] The fused polycyclic compound according to the embodiment represented by Formula 1 may include a structure in which three aromatic rings are fused via a boron atom, a first nitrogen atom, and a second nitrogen atom. In the specification, in Formula 1, R 1 To R 3 The benzene ring of the substituent represented by may correspond to the first aromatic ring, and is substituted by R 4 To R 7 The benzene ring of the substituent represented by may correspond to the second aromatic ring, and may be substituted therewith by R 8 To R 10 The benzene ring of the substituent represented by may correspond to the third aromatic ring. a1 To R a3 and R b The heterocyclic ring of the substituent represented by may correspond to the first substituent. 11 and R 12 The heterocyclic ring represented by the substituent may correspond to the above-mentioned second substituent.

[0234] In formula 1, R 1 To R 10 Each of them may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, R 1 To R 10 Each of them may independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted n-propyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzoselenophene group, a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted triphenylsilyl group.

[0235] In the embodiment, in Formula 1, R 1 To R 10 At least one of each may independently be a group selected from Substituent Group 1 which will be explained later.

[0236] In formula 1, in addition to R a1 To R a3 In addition to the fact that at least one of them may be independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R a1 To R a3 Each of them may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, R a1 To R a3 Each of them may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted carbazolyl group.

[0237] In the embodiment, in Formula 1, R a1 To R a3 At least one of may be a substituted or unsubstituted aromatic group having 6 to 30 ring carbon atoms. a1 To R a3 At least one of may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0238] In formula 1, R b , R 11 and R 12 Each of them may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and may be optionally combined with adjacent groups to form a ring. For example, R b may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group; and R 11 and R 12 Each of them may independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted dibenzofuranyl group.

[0239] In formula 1, Ar 1It may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 It may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted dibenzofuranyl group.

[0240] In Formula 1, m1, n1, and n2 may each independently be an integer of 0 to 4. In Formula 1, if m1, n1, and n2 are 0, the fused polycyclic compound of the embodiment may be unreacted by R b , R 11 and R 12 m1, n1 and n2 are 4 and R b , R 11 and R 12 The case where all of R are hydrogen atoms may be the same as the case where m1, n1 and n2 are 0 respectively. If m1, n1 and n2 are integers of 2 or more, then the plurality of R b , R 11 and R 12 Each of the R can be the same, or multiple R b , R 11 and R 12 At least one of them may be different.

[0241] In the embodiment, in Formula 1, Ar 1 It may be a group represented by one of Formulae X-1 to X-5.

[0242] [Formula X-1]

[0243]

[0244] [Formula X-2]

[0245]

[0246] [Formula X-3]

[0247]

[0248] [Formula X-4]

[0249]

[0250] [Formula X-5]

[0251]

[0252] In formula X-1, Z a Can be O or S. For example, Z a It can be O.

[0253] In Formula X-1 to Formula X-5, R c To R r Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and may be optionally combined with adjacent groups to form a ring.

[0254] In Formula X-1 to Formula X-5, a1, a5, a8 and a12 can each independently be an integer from 0 to 3; a2, a6, a10, a13 and a15 can each independently be an integer from 0 to 4; and a3, a4, a7, a9, a11, a14 and a16 can each independently be an integer from 0 to 5.

[0255] In Formula X-1 to Formula X-5, if a1 to a16 are 0, the fused polycyclic compounds of the embodiments may be respectively unreacted by R c To R r a1, a5, a8 and a12 are 3 and all R c , R g , R j and R n The case where all of them are hydrogen atoms can be the same as the case where a1, a5, a8 and a12 are 0. a2, a6, a10, a13 and a15 are 4 and all R d , R h , R l , R o and R q The case where all of them are hydrogen atoms may be the same as the case where a2, a6, a10, a13 and a15 are 0. a3, a4, a7, a9, a11, a14 and a16 are 5 and all R e , R f , R i , R k , R m , R p and R r The case where all of them are hydrogen atoms may be the same as the case where a3, a4, a7, a9, a11, a14 and a16 are 0 respectively. If a1 to a16 are integers of 2 or more, then the plurality of R c To R r Each of the R can be the same, or multiple R c To R r At least one of them may be different.

[0256] In an embodiment, the first compound represented by Formula 1 may be represented by one of Formula 2-1 to Formula 2-3.

[0257] [Formula 2-1]

[0258]

[0259] [Formula 2-2]

[0260]

[0261] [Formula 2-3]

[0262]

[0263] Formula 2-1 to Formula 2-3 represent the following: a1 To R a3 Formula 2-1 represents that R a1 Formula 1 may be an aryl group or a heteroaryl group. Formula 2-2 represents a a2 Formula 1 may be an aryl group or a heteroaryl group. Formula 2-3 represents a group in which R a3 The group of Formula 1 may be an aryl group or a heteroaryl group.

[0264] In Formula 2-1 to Formula 2-3, Y 1 To Y 3 and Y may be independently substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms or substituted or unsubstituted heteroaryl groups having 2 to 30 ring carbon atoms. 1 To Y 3 Each of them may be independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. 1 To Y 3 Each of them independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0265] In Formula 2-1 to Formula 2-3, Ar 1 , R 1 To R 12 , R a1 To R a3 , R b , m1, n1 and n2 may be the same as described in Formula 1.

[0266] In an embodiment, the first compound may be represented by Formula 3.

[0267] [Formula 3]

[0268]

[0269] In formula 3, in addition to R b1 To Rb4 In addition to the fact that at least one of them may be independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R b1 To R b4 Each of them may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and may be optionally combined with adjacent groups to form a ring. For example, R b1 To R b4 Each of them may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.

[0270] In the embodiment, in Formula 3, R b1 To R b4 At least one of them may be independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted carbazolyl group.

[0271] In formula 3, Ar 1 , R 1 To R 12 , R a1 To R a3 , n1 and n2 may be the same as described in Formula 1.

[0272] In an embodiment, the first compound may be represented by Formula 4-1 or Formula 4-2.

[0273] [Formula 4-1]

[0274]

[0275] [Formula 4-2]

[0276]

[0277] Formula 4-1 and Formula 4-2 represent embodiments in which the third substituent can be connected to the second nitrogen atom of the fused ring core of Formula 1. The fused polycyclic compound according to the embodiment may further include a third substituent connected to the fused ring core. The third substituent may include a dibenzofuran moiety or a terphenyl moiety. Formula 4-1 represents the case where a dibenzofuran moiety is included as the third substituent. Formula 4-2 represents the case where a terphenyl moiety is included as the third substituent.

[0278] In an embodiment, the third substituent may include a dibenzofuran moiety. For example, the third substituent may include a second dibenzofuran moiety and a second substituent connected to the second dibenzofuran moiety. The second substituent may be an aryl of 6 to 30 ring-forming carbon atoms substituted or unsubstituted or a heteroaryl of 2 to 30 ring-forming carbon atoms substituted or unsubstituted. The third substituent may be connected to the second nitrogen atom of the fused ring core via the carbon at position 4 of the second dibenzofuran moiety. The second substituent may be connected to the benzene ring connected to the second nitrogen atom among the two benzene rings constituting the second dibenzofuran moiety. For example, the carbon at position 4 of the second dibenzofuran moiety may be connected to the second nitrogen atom, and the second substituent may be connected to at least one of the remaining carbons at positions 1 to 3. The carbon numbering of the first substituent may be the same as the carbon numbering of the second dibenzofuran moiety.

[0279] In another embodiment, the third substituent may include a terphenyl moiety. For example, the third substituent may include a connection structure of three benzene moieties. For example, the third substituent may include a first benzene moiety connected to the second nitrogen atom of the fused ring core and a second benzene moiety and a third benzene moiety substituted at a specific position of the first benzene moiety. For example, the third substituent may include a first benzene moiety connected to the second nitrogen atom of the fused ring core and a second benzene moiety and a third benzene moiety connected to a carbon atom at an ortho position relative to the second nitrogen atom among the carbon atoms constituting the first benzene moiety.

[0280] In Formula 4-1 and Formula 4-2, R c1 To R c3 , R d , R e , R f and R g1 To R g3 Each of them may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and may be optionally combined with adjacent groups to form a ring. For example, R c1 To R c3 and R are independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group. d It may be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group. e and R fand R are independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group. g1 To R g3 They may each independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted tert-butyl group.

[0281] In Formula 4-1, m2 may be an integer from 0 to 4. In Formula 4-1, if m2 is 0, the fused polycyclic compound of the embodiment may not be R d In formula 4-1, m2 is 4 and all R d The case where m2 is a hydrogen atom may be the same as the case of Formula 4-1 where m2 is 0. If m2 is an integer of 2 or more, then the plurality of R d Can be all the same, or multiple R d At least one of them may be different.

[0282] In Formula 4-2, m3 and m4 may each independently be an integer of 0 to 5. In Formula 4-2, if m3 and m4 are 0, the fused polycyclic compound of the embodiment may be unreacted by R e and R f Replace. m3 and m4 are 5 and all R e and R f The case where m3 and m4 are both hydrogen atoms may be the same as the case where m3 and m4 are 0. If m3 and m4 are integers of 2 or more, then the plurality of R e and R f Each of the R can be the same, or multiple R e and R f At least one of them may be different.

[0283] In formula 4-1, R c1 To R c3 At least one of them may be independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. c1 To R c3 At least one of them may be each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0284] In Formula 4-1 and Formula 4-2, R 1 To R 12 , R a1 To R a3 , R b , m1, n1 and n2 may be the same as described in Formula 1.

[0285] In an embodiment, the first compound may be represented by Formula 5.

[0286] [Formula 5]

[0287]

[0288] In formula 5, except for Z 1 To Z 5 At least one of them may be independently a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms or a group represented by one of Formula A-1 to Formula A-5, Z 1 To Z 5 Each of them may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, Z 1 To Z 5 Each of them may independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted n-propyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzoselenophene group, a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted triphenylsilyl group.

[0289] In the embodiment, in Formula 5, Z 2 and Z 3 At least one of the above may be independently a group represented by one of Formulas A-1 to A-5. For example, in Formula 5, Z 2 It may be a group represented by one of Formulas A-1 to A-5. As another example, in Formula 5, Z 3 It may be a group represented by one of Formula A-1 to Formula A-5.

[0290] In the embodiment, in Formula 5, Z 2 , Z 3 and Z 5 At least one of them may be independently a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms or a group represented by one of Formulas A-1 to A-5. For example, in Formula 5, Z 2 and Z 5 and Z are independently substituted or unsubstituted methyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, or a group represented by one of Formulas A-1 to A-5. 3 and Z5 Each may independently be a substituted or unsubstituted methyl group, a substituted or unsubstituted n-propyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, or a group represented by one of Formula A-1 to Formula A-5.

[0291] [Formula A-1]

[0292]

[0293] [Formula A-2]

[0294]

[0295] [Formula A-3]

[0296]

[0297] [Formula A-4]

[0298]

[0299] [Formula A-5]

[0300]

[0301] In Formula A-1 to Formula A-5, X 1 It can be O, S, Se, N (Q 11 ) or C(Q 12 )(Q 13 ).

[0302] In Formula A-1 to Formula A-5, Q 1 To Q 13 Q may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 To Q 13 Each of them may independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted triphenylsilyl group, or a substituted or unsubstituted phenyl group.

[0303] In Formula A-1 to Formula A-5, m11 to m13 and m18 to m20 may each independently be an integer of 0 to 5; m14, m15, and m17 may each independently be an integer of 0 to 4; and m16 may be an integer of 0 to 3.

[0304] In Formula A-1 to Formula A-5, if m11 to m20 are 0, the fused polycyclic compounds of the embodiments may be respectively un-Q1 To Q 10 Replace. m11 to m13 and m18 to m20 are 5 and all Q 1 To Q 3 and Q 8 To Q 10 The case where all of them are hydrogen atoms can be the same as the case where m11 to m13 and m18 to m20 are 0 respectively. m14, m15 and m17 are 4 and all Q 4 , Q 5 and Q 7 The case where all of them are hydrogen atoms can be the same as the case where m14, m15 and m17 are 0 respectively. m16 is 3 and all Q 6 The case where m11 to m20 are 2 or more can be the same as the case where m16 is 0. 1 To Q 10 Each of the Q 1 To Q 10 At least one of them may be different.

[0305] In formula 5, Ar 1 , R 1 To R 3 , R 8 , R 10 To R 12 , R a1 To R a3 , R b , m1, n1 and n2 may be the same as described in Formula 1.

[0306] In an embodiment, Z 1 To Z 5 At least one of them may be independently a group selected from Substituent Group 1.

[0307] [Substituent Group 1]

[0308]

[0309]

[0310]

[0311]

[0312] In an embodiment, the first compound may be represented by Formula 6-1 or Formula 6-2.

[0313] [Formula 6-1]

[0314]

[0315] [Formula 6-2]

[0316]

[0317] In equation 6-1 and equation 6-2, A 1a and A 1b Each of A and B may be independently a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1a and A 1b and A and B may be independently cyano, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted triphenylsilyl. 1a and A 1b Each may be independently a group selected from Substituent Group 1.

[0318] In equation 6-1 and equation 6-2, A 2 It may be a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms. 2 It may be a substituted or unsubstituted methyl group, a substituted or unsubstituted n-propyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzoselenophene group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenyl group. In the embodiment, in Formula 6-1 and Formula 6-2, A 2 It may be a group selected from Substituent Group 1.

[0319] In equation 6-1 and equation 6-2, B 1 To B 8 and C 1 To C 8 Each may independently be a hydrogen atom or a deuterium atom.

[0320] In Formula 6-1 and Formula 6-2, Ar 1a It may be a group represented by Formula B-1 or Formula B-2.

[0321] [Formula B-1]

[0322]

[0323] [Formula B-2]

[0324]

[0325] In Formula B-1 and Formula B-2, R c1 To R c3 , R d , R e , R f and R g1 To R g3 Each of them may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and may be optionally combined with adjacent groups to form a ring. For example, R c1 To R c3 and R are independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group. d It may be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group. e and R f and R are independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group. g1 To R g3 They may each independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted tert-butyl group.

[0326] In Formula B-1, m2 may be an integer from 0 to 4. In Formula B-1, if m2 is 0, the fused polycyclic compound of the embodiment may not be R d In formula B-1, m2 is 4 and all R d The case where m2 is a hydrogen atom may be the same as the case where m2 is 0. If m2 is an integer of 2 or more, then the plurality of R d Can be all the same, or multiple R d At least one of them may be different.

[0327] In Formula B-2, m3 and m4 may each independently be an integer of 0 to 5. In Formula B-2, if m3 and m4 are 0, the fused polycyclic compound of the embodiment may be unreacted by R e and R f Replace. m3 and m4 are 5 and all R e and R fThe case where m3 and m4 are both hydrogen atoms may be the same as the case where m3 and m4 are 0. If m3 and m4 are integers of 2 or more, then the plurality of R e and R f Each of the R can be the same, or multiple R e and R f At least one of them may be different.

[0328] In formula B-1, R c1 To R c3 At least one of them may be independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. c1 To R c3 At least one of them may be each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0329] In equations 6-1 and 6-2, R 11 , R 12 , R a1 To R a3 , R b , m1, n1 and n2 may be the same as described in Formula 1.

[0330] In an embodiment, the first compound may be represented by Formula 7-1 or Formula 7-2.

[0331] [Formula 7-1]

[0332]

[0333] [Formula 7-2]

[0334]

[0335] The fused polycyclic compound according to the embodiment may further include a fourth substituent that may be connected to the aromatic ring of the fused core. The fourth substituent may be an electron donor substituent and may include a carbazole moiety. The fourth substituent may be connected to the second aromatic ring of the fused core. The fourth substituent may be connected to the second aromatic ring at a para position relative to the boron atom. In Formula 7-1 and Formula 7-2, R 13 and R 14 The heterocyclic ring may correspond to the fourth substituent.

[0336] In equations 7-1 and 7-2, R 13 , R 14 , R c1 To R c3 and R dEach of them may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and may be optionally combined with adjacent groups to form a ring. For example, R 13 and R 14 Each of them may independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.

[0337] In Formula 7-1 and Formula 7-2, n13, n14 and m2 may be independently integers of 0 to 4. In Formula 7-1 and Formula 7-2, if n13, n14 and m2 are 0, the fused polycyclic compound of the embodiment may be unreacted by R 13 , R 14 and R d n13, n14 and m2 are 4 and all R 13 , R 14 and R d The case where n13, n14 and m2 are all hydrogen atoms may be the same as the case where n13, n14 and m2 are 0. If n13, n14 and m2 are integers of 2 or more, then the plurality of R 13 , R 14 and R d Each of the R can be the same, or multiple R 13 , R 14 and R d At least one of them may be different.

[0338] In Formula 7-1 and Formula 7-2, Ar 1 , R 1 To R 5 , R 7 To R 12 , R a1 To R a3 , R b , m1, n1 and n2 may be the same as described in Formula 1.

[0339] In an embodiment, the fused polycyclic compound represented by Formula 1 may include at least one deuterium atom as a substituent. In an embodiment, in the fused polycyclic compound represented by Formula 1, at least one hydrogen atom may be optionally substituted with a deuterium atom.

[0340] In an embodiment, the condensed polycyclic compound may be any compound selected from compound group 1. At least one functional layer included in the light emitting element ED according to an embodiment may each independently include at least one condensed polycyclic compound selected from compound group 1. In an embodiment, in the light emitting element ED, at least one functional layer (e.g., emission layer EML) may include at least one condensed polycyclic compound selected from compound group 1.

[0341] [Compound Group 1]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355] In specific compounds proposed in compound group 1, D is a deuterium atom.

[0356] The fused polycyclic compound according to the embodiment represented by Formula 1 has a structure in which the first substituent is linked to the fused ring core, and may achieve high efficiency and long life, and may have advantages that the emission wavelength may be blue-shifted and the emission wavelength may be precisely controlled at the same time.

[0357] The fused polycyclic compound according to the embodiment may include a "fused ring core" of five rings formed by fusing the first aromatic ring to the third aromatic ring via a boron atom, a first nitrogen atom, and a second nitrogen atom. In an embodiment, the fused polycyclic compound may include a first substituent connected to the first nitrogen atom of the fused ring core and a second substituent connected to the first aromatic ring of the fused ring core. The fused polycyclic compound represented by Formula 1 according to the embodiment may include a first substituent and a second substituent, and may achieve high emission efficiency and increased lifetime.

[0358] The first substituent may include a first dibenzofuran moiety connected to an aromatic substituent. The carbon atom at position 4 of the first dibenzofuran moiety may be connected to the first nitrogen atom of the fused ring core, and at least one of the remaining carbon atoms at positions 1 to 3 may be connected to an aromatic substituent. The fused polycyclic compound according to the embodiment may show high steric bulkiness due to the specific connection structure of the first substituent, and may effectively protect the triangular planar structure of the boron atom in the fused ring core, and therefore, the stability of the material may be improved during the operation of the light-emitting element. The boron atom has an electron-deficient property due to the empty p orbital, and may form a bond with another nucleophilic reagent to be converted into a tetrahedral structure. This change in tetrahedral configuration may cause degradation of the light-emitting element. According to an embodiment, in the fused polycyclic compound, since the first substituent is introduced into the fused ring core, the empty p orbital of the boron atom may be effectively protected, and the degradation of the light-emitting element caused by the structural deformation of the boron atom may be prevented.

[0359] In an embodiment, in a fused polycyclic compound, intermolecular interactions can be suppressed by the steric hindrance effect of the first substituent, so that the formation of agglomerates, exciplexes or exciplexes can be controlled, and the emission efficiency can be increased. Since the fused polycyclic compound according to the embodiment represented by Formula 1 has a large structure, the intermolecular distance can be increased, and the Dexter energy transfer can be reduced. Dexter energy transfer is a phenomenon of transferring triplet excitons between molecules, and if the distance between molecules is short, the Dexter energy transfer increases, and according to the increase in triplet concentration, the Dexter energy transfer may become a factor that increases the quenching phenomenon. According to an embodiment, in a fused polycyclic compound, the intermolecular distance between adjacent molecules increases due to large steric hindrance, the Dexter energy transfer can be suppressed, and the lifetime degradation caused by the increase in triplet concentration can be suppressed. Therefore, if the fused polycyclic compound according to the embodiment is applied to the emission layer EML, the emission efficiency can be increased, and the element life can be improved.

[0360] In an embodiment, the fused polycyclic compound may have a structure in which a dibenzofuran moiety having a large electronegativity is connected to a fused ring core at a specific position, and the emission wavelength is blue-shifted to achieve high color purity. Therefore, in the fused polycyclic compound according to an embodiment, by including a first substituent and changing the type of substituent connected to the fused ring core and / or the first substituent, the emission wavelength can be blue-shifted while accurately controlling the emission wavelength. For example, the fused polycyclic compound according to an embodiment can control the target emission wavelength in a wavelength region within a range of about 430nm to about 490nm without significantly changing the optical properties and physical properties.

[0361] If the fused polycyclic compound according to the embodiment is applied to a light emitting element, high efficiency and long life can be achieved due to a synergistic effect according to the connection positions of dibenzofuran and the first nitrogen atom and the introduction of a specific substituent of the dibenzofuran moiety.

[0362] In an embodiment, the fused polycyclic compound may have a structure in which a second substituent is connected to a fused ring including a boron atom and a nitrogen atom. The second substituent may include a carbazole moiety and may be directly connected to the first aromatic ring forming the fused ring. Therefore, the fused polycyclic compound according to the embodiment may display multiple resonances at a wide plate-type skeleton and allow the highest occupied molecular orbital (HOMO) state and the lowest unoccupied molecular orbital (LUMO) state in the molecule to be easily separated, and therefore may be used as a delayed fluorescence emission material. The fused polycyclic compound according to the embodiment may have a reduced difference (ΔE) between the lowest triplet excitation energy level (T1 energy level) and the lowest singlet excitation energy level (S1 energy level) due to the structure. ST ), therefore, if used as a delayed fluorescence emission material, the emission efficiency of the light-emitting element ED can be even further improved.

[0363] In an embodiment, the fused polycyclic compound may include a first substituent, and its synthesis may be easily performed, and process efficiency may be improved. As a method for spatially protecting boron, an ortho-terphenyl moiety represented by the following formula T may be introduced. However, in the case of ortho-terphenyl, due to its spatial structure, this moiety may not be easy to synthesize. As a method for synthesizing a fused polycyclic compound having boron at the center, a coupling reaction (such as borylation and Ullmann reaction) may be used. Boration may include a transfer metalation reaction for modifying the CH bond of an aromatic ring to CB and a subsequent cyclization reaction for forming a fused ring. The Ullmann reaction is a coupling reaction between an aryl halide and an arylamine, and can be used as a reaction for replacing the corresponding substituent at the fused ring core. For the borylation of a polycyclic compound in which ortho-terphenyl is introduced, the borylation using a nucleophilic reagent (such as BuLi) is difficult due to its spatial structure, and the use of expensive BI 3During the Ullmann reaction, a large amount of reagents is required due to the steric structure of o-terphenyl, and there may be a disadvantage associated with increased costs.

[0364] [Formula T]

[0365]

[0366] In the specification, in the fused ring core with a boron atom and two nitrogen atoms at the center, the structure in which the first substituent can be connected to at least one of the nitrogen atoms on both sides can show an excellent boron protection effect, and its structure can be easily synthesized. The first substituent can be connected to at least one of the two nitrogen atoms constituting the fused ring core. In the fused polycyclic compound according to an embodiment, since the first substituent can be connected to the fused ring core at a specific position, it is possible to show a steric bulkiness similar to that of the polycyclic compound in which the ortho-terphenyl is substituted at the nitrogen atoms on both sides, and improved synthesis can be achieved. When compared with the polycyclic compound of the related art in which ortho-terphenyl is introduced, the boronization of the polycyclic compound in which the first substituent is introduced can allow the use of a nucleophilic reagent (such as BuLi) for boronization, and the amount of reactants during the Ullmann reaction can be reduced, thereby reducing manufacturing costs and improving process efficiency.

[0367] In an embodiment, the emission spectrum of the fused polycyclic compound represented by Formula 1 may have a full width at half maximum (FWHM) in the range of about 10 nm to 50 nm. For example, the emission spectrum of the fused polycyclic compound may have a FWHM in the range of about 20 nm to 40 nm. Since the emission spectrum of the first dopant according to the embodiment represented by Formula 1 has a full width at half maximum in the above range, if applied to a light-emitting element, the emission efficiency can be improved. If used as a material for a blue light-emitting element, the element life can be improved.

[0368] In an embodiment, the fused polycyclic compound represented by Formula 1 may be a material for emitting thermally activated delayed fluorescence. In an embodiment, the fused polycyclic compound represented by Formula 1 may be a thermally activated delayed fluorescence dopant having a difference (ΔE) between the lowest triplet excitation energy level (T1 level) and the lowest singlet excitation energy level (S1 level) of less than or equal to about 0.6 eV. ST ). The fused polycyclic compound according to the embodiment represented by Formula 1 may be a thermally activated delayed fluorescence dopant having a difference (ΔE) between the lowest triplet excitation energy level (T1 level) and the lowest singlet excitation energy level (S1 level) of less than or equal to about 0.2 eV. ST ). However, the embodiment is not limited thereto.

[0369] In an embodiment, the fused polycyclic compound represented by Formula 1 may include a first substituent and a second substituent in the compound. By controlling the number and position of substitution of the first substituent and the second substituent, the singlet energy level and triplet energy level of the entire compound may be appropriately controlled. Thus, the fused polycyclic compound may exhibit improved thermally activated delayed fluorescence properties.

[0370] The fused polycyclic compound according to the embodiment represented by Formula 1 may be a light-emitting material having a central wavelength in the range of about 430 nm to about 490 nm. For example, the fused polycyclic compound according to the embodiment represented by Formula 1 may be a blue thermally activated delayed fluorescence (TADF) dopant. However, the embodiment is not limited thereto, and if the fused polycyclic compound is used as a light-emitting material, the first dopant may be used as a dopant material (such as a red emission dopant or a green emission dopant) that emits light in various wavelength regions.

[0371] In an embodiment, in the light emitting element ED, the emission layer EML may emit delayed fluorescence. For example, the emission layer EML may emit thermally activated delayed fluorescence (TADF).

[0372] In an embodiment, the emission layer EML of the light emitting element ED may emit blue light. For example, the emission layer EML of the light emitting element ED may emit blue light having a wavelength less than or equal to about 490 nm. However, the embodiment is not limited thereto, and the emission layer EML may emit green light or red light.

[0373] The fused polycyclic compound according to the embodiment may be included in the emission layer EML. The fused polycyclic compound according to the embodiment may be included in the emission layer EML as a dopant material. The fused polycyclic compound according to the embodiment may be a thermally activated delayed fluorescence emission material. The fused polycyclic compound according to the embodiment may be used as a thermally activated delayed fluorescence dopant. For example, in the light-emitting element ED, the emission layer EML may include at least one fused polycyclic compound selected from compound group 1 as a thermally activated delayed fluorescence dopant. However, the use of the fused polycyclic compound according to the embodiment is not limited thereto.

[0374] In an embodiment, the emission layer EML may include a plurality of compounds. The emission layer EML according to an embodiment may include a fused polycyclic compound represented by Formula 1 as a first compound and at least one of a second compound represented by Formula HT-1, a third compound represented by Formula ET-1, and a fourth compound represented by Formula D-1.

[0375] In an embodiment, the emission layer EML may include the first compound represented by Formula 1, and may further include at least one of the second compound represented by Formula HT-1 and the third compound represented by Formula ET-1.

[0376] In an embodiment, the emission layer EML may further include a second compound represented by Formula HT-1. In an embodiment, the second compound may be used as a hole transport host material in the emission layer EML.

[0377] [Formula HT-1]

[0378]

[0379] In formula HT-1, M 1 To M 8 can be independently N or C (R 51 ). For example, M 1 To M 8 can be independently C(R 51 As another example, M 1 To M 8 One of them can be N, and M 1 To M 8 The rest of the parts may be independently C(R 51 ).

[0380] In formula HT-1, L 1 It may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. 1 It may be a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent carbazole group, etc., but the embodiment is not limited thereto.

[0381] In formula HT-1, Y a Can be a direct key, C(R 52 )(R 53 ) or Si(R 54 )(R 55 ). For example, the two benzene aromatic rings bonded to the nitrogen atom in formula HT-1 can be connected via a direct bond, In formula HT-1, if Y a is a direct bond, the substituent represented by Formula HT-1 may include a carbazole moiety.

[0382] In formula HT-1, Ar a It may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. a It may be a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted biphenyl group, etc., but the embodiment is not limited thereto.

[0383] In formula HT-1, R 51 To R 55 Each of them may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms, and may be optionally combined with adjacent groups to form a ring. For example, R 51 To R 55 can be independently a hydrogen atom or a deuterium atom. 51 To R 55 Each may independently be an unsubstituted methyl group or an unsubstituted phenyl group.

[0384] In the embodiment, the second compound represented by Formula HT-1 may be selected from Compound Group 2. In the embodiment, in the light emitting element ED, the second compound may include at least one compound selected from Compound Group 2.

[0385] [Compound Group 2]

[0386]

[0387]

[0388]

[0389] In compound group 2, D may be a deuterium atom, and Ph may be a substituted or unsubstituted phenyl group. For example, in compound group 2, Ph may be an unsubstituted phenyl group.

[0390] In an embodiment, the emission layer EML may further include a third compound represented by Formula ET-1. In an embodiment, the third compound may be used as an electron transport host material in the emission layer EML.

[0391] [Formula ET-1]

[0392]

[0393] In formula ET-1, Z a To Z c At least one of them can be N, and Z a To Z c The rest of the parts can be independently C(R 56 ). For example, Z a To Z c At least one of them can be N, and Z aTo Z c The rest of the parts in may be independently C(R 56 ). Therefore, the third compound represented by Formula ET-1 may include a pyridine moiety. As another example, Z a To Z c At least two of them can both be N, and Z a To Z c The rest of the can be C(R 56 ). Therefore, the third compound represented by Formula ET-1 may include a pyrimidine moiety. As another example, Z a To Z c Both may be N. Therefore, the third compound represented by Formula ET-1 may include a triazine moiety.

[0394] In formula ET-1, R 56 It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms.

[0395] In Formula ET-1, b1 to b3 may each independently be an integer of 0 to 10.

[0396] In formula ET-1, Ar b To Ar d and R and R are independently hydrogen atoms, deuterium atoms, substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted aryl groups of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl groups of 2 to 30 ring carbon atoms. b To Ar d Each of them independently may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted carbazolyl group.

[0397] In formula ET-1, L 2 To L 4 Each of b1 to b3 is independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. 2 To L 4 Each of them may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0398] In the embodiment, the third compound represented by Formula ET-1 may be selected from Compound Group 3. In the embodiment, in the light emitting element ED, the third compound may include at least one compound selected from Compound Group 3.

[0399] [Compound Group 3]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407] In compound group 3, D may be a deuterium atom, and Ph may be an unsubstituted phenyl group.

[0408] In an embodiment, the emission layer EML may include a second compound and a third compound, and the second compound and the third compound may form an exciplex. In the emission layer EML, the exciplex may be formed by a hole transport host and an electron transport host. The triplet energy level of the exciplex formed by the hole transport host and the electron transport host may correspond to the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the electron transport host and the highest occupied molecular orbital (HOMO) energy level of the hole transport host.

[0409] For example, the absolute value of the triplet energy level (T1) of the exciplex formed by the hole transport host and the electron transport host may be in the range of about 2.4 eV to about 3.0 eV. The triplet energy level of the exciplex may have a value smaller than the energy gap of each host material. The exciplex may have a triplet energy level equal to or less than about 3.0 eV (which is the energy gap between the hole transport host and the electron transport host).

[0410] In an embodiment, the emission layer EML may include a fourth compound in addition to the first compound, the second compound, and the third compound. The fourth compound may be used as a phosphorescence sensitizer in the emission layer EML. Since energy may be transferred from the fourth compound to the first compound, light emission may occur.

[0411] The emission layer EML may include an organic metal complex including platinum (Pt) as a central metal atom and a ligand bonded to the central metal atom as a fourth compound. In an embodiment, the emission layer EML may further include a compound represented by Formula D-1 as a fourth compound.

[0412] [Formula D-1]

[0413]

[0414] In formula D-1, Q 1 To Q 4 can all independently be C or N.

[0415] In Formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring of 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring of 2 to 30 ring carbon atoms.

[0416] In formula D-1, L 11 To L 13 Can be directly connected, *-O-*, *-S-*, a substituted or unsubstituted alkylene group of 1 to 20 carbon atoms, a substituted or unsubstituted arylene group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring carbon atoms. 11 To L 13 In the above, “—*” indicates a bond connected to one of C1 to C4.

[0417] In formula D-1, b11 to b13 may each independently be 0 or 1. If b11 is 0, C1 and C2 may not be directly connected to each other. If b12 is 0, C2 and C3 may not be directly connected to each other. If b3 is 0, C3 and C4 may not be directly connected to each other.

[0418] In formula D-1, R 61 To R 66 Each of them may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms, and may be optionally combined with adjacent groups to form a ring. For example, R 61 To R 66 Each may independently be a substituted or unsubstituted methyl group or a substituted or unsubstituted tert-butyl group.

[0419] In Formula D-1, d1 to d4 may each independently be an integer of 0 to 4. In Formula D-1, if d1 to d4 are all 0, the fourth compound may be unreacted by R 61 To R 64 d1 to d4 are 4 and R 61 To R 64The case where d1 to d4 are hydrogen atoms may be the same as the case where d1 to d4 are 0. If d1 to d4 are integers of 2 or more, then the plurality of R 61 To R 64 Each of the R can be the same, or multiple R 61 To R 64 At least one of them may be different.

[0420] In an embodiment, in Formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring represented by any one of Formulas C-1 to C-4.

[0421]

[0422] In Formula C-1 to Formula C-4, P 1 Can be c-* or C(R 74 ), P 2 Can be N—* or N(R 81 ), P 3 Can be N—* or N(R 82 ), and P 4 Can be c-* or C(R 88 ).

[0423] In Formula C-1 to Formula C-4, R 71 To R 88 Each may independently be a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and may optionally combine with an adjacent group to form a ring.

[0424] In Formula C-1 to Formula C-4, represents a bond to Pt, and —* represents a bond to an adjacent ring group (C1 to C4) or a linker (L 11 To L 13 ) key.

[0425] In an embodiment, the emission layer EML may include a first compound represented by Formula 1, and may further include at least one of a second compound, a third compound, and a fourth compound. In an embodiment, the emission layer EML may include the first compound, the second compound, and the third compound. In the emission layer EML, the second compound and the third compound may form an exciplex, in which energy transfer to the first compound may occur and light emission may occur.

[0426] In another embodiment, the emission layer EML may include a first compound, a second compound, a third compound, and a fourth compound. In the emission layer EML, the second compound and the third compound may form an exciplex, in which energy may be transferred from the exciplex to the fourth compound and the first compound, and light emission may occur. In an embodiment, the fourth compound may be a sensitizer. In the light-emitting element ED, the fourth compound included in the emission layer EML may be used as a sensitizer, and energy may be transferred from the host to the first compound as a light-emitting dopant. For example, the fourth compound used as an auxiliary dopant may accelerate the energy transfer to the first compound as a light-emitting dopant, thereby increasing the emission ratio of the first compound. Therefore, the efficiency of the emission layer EML may be improved. If the energy transferred to the first compound increases, the excitons formed in the emission layer EML may not accumulate, but may emit light quickly, so that the degradation of the device may be reduced. Therefore, the life of the light-emitting element ED may be increased.

[0427] The light emitting element ED may include a first compound, a second compound, a third compound, and a fourth compound, and the emission layer EML may include a combination of two host materials and two dopant materials. In the light emitting element ED, the emission layer EML may include the second compound and the third compound as two different hosts, the first compound emitting delayed fluorescence, and the fourth compound including an organic metal complex, so the light emitting element ED may exhibit excellent emission efficiency properties.

[0428] In the embodiment, the fourth compound represented by Formula D-1 may be selected from Compound Group 4. In the embodiment, in the light emitting element ED, the fourth compound may include at least one compound selected from Compound Group 4.

[0429] [Compound Group 4]

[0430]

[0431]

[0432] In compound group 4, D may be a deuterium atom.

[0433] In an embodiment, the light emitting element ED may include a plurality of emission layers EML. The plurality of emission layers EML may be arranged as a stack so that the light emitting element ED including the plurality of emission layers EML may emit white light. The light emitting element ED including the plurality of emission layers EML may be a light emitting device having a series structure. If the light emitting element ED includes a plurality of emission layers EML, at least one emission layer EML may include a first compound represented by Formula 1. For example, if the light emitting element ED includes a plurality of emission layers EML, at least one emission layer EML may include a first compound, a second compound, a third compound, and a fourth compound.

[0434] In the light emitting element ED according to the embodiment, if the emission layer EML includes a first compound, a second compound, a third compound, and a fourth compound, the amount of the first compound may be in the range of about 0.1 wt % to about 5 wt % based on the total weight of the first compound, the second compound, the third compound, and the fourth compound. However, the embodiment is not limited thereto. If the amount of the first compound satisfies the above range, energy transfer from the second compound and the third compound to the first compound may be increased, and therefore, emission efficiency and device life may be increased.

[0435] In the emission layer EML, the total amount of the second compound and the third compound may be the remaining amount of the total weight of the first compound, the second compound, the third compound, and the fourth compound excluding the amount of the first compound and the fourth compound. For example, based on the total weight of the first compound, the second compound, the third compound, and the fourth compound, the total amount of the second compound and the third compound may be in the range of about 65 wt % to about 95 wt %.

[0436] Within the combined amount of the second compound and the third compound in the emission layer EML, a weight ratio of the second compound to the third compound may be in the range of about 3:7 to about 7:3.

[0437] If the total amount of the second compound and the third compound satisfies the above range and ratio, the charge balance property in the emission layer EML can be improved, and the emission efficiency and device life can be improved. If the total amount of the second compound and the third compound deviates from the above range and ratio, the charge balance in the emission layer EML may not be achieved, so that the luminous efficiency may be reduced, and the device may be more easily degraded.

[0438] If the emission layer EML includes a fourth compound, the amount of the fourth compound may be in the range of about 4 wt % to 30 wt % based on the total weight of the first compound, the second compound, the third compound, and the fourth compound in the emission layer EML. However, the embodiment is not limited thereto. If the amount of the fourth compound satisfies the above range, the energy transfer from the host to the first compound as a light-emitting dopant can be increased, and the emission ratio can be improved. Therefore, the emission efficiency of the emission layer EML can be improved. If the amounts of the first compound, the second compound, the third compound, and the fourth compound included in the emission layer EML satisfy the above range and ratio, excellent emission efficiency and long life can be achieved.

[0439] In the light emitting element ED, the emission layer EML may further include anthracene derivatives, pyrene derivatives, fluoranthene derivatives, Derivatives, dihydrobenzanthracene derivatives or benzo[9,10]phenanthrene derivatives. For example, the emission layer EML may include anthracene derivatives or pyrene derivatives.

[0440] In such Figures 3 to 6 In the light emitting element ED according to the embodiment shown in FIG. 1 , the emission layer EML may further include a host and a dopant of the related art in addition to the above-mentioned host and dopant.

[0441] In an embodiment, the emission layer EML may include a compound represented by Formula E-1. The compound represented by Formula E-1 may be used as a fluorescent host material.

[0442] [Formula E-1]

[0443]

[0444] In formula E-1, R 31 To R 40 Each of them may be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 10 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and may be optionally combined with adjacent groups to form a ring. In an embodiment, R 31 To R 40 It may combine with an adjacent group to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated heterocyclic ring, or an unsaturated heterocyclic ring.

[0445] In Formula E-1, c and d may each independently be an integer of 0 to 5.

[0446] In an embodiment, the compound represented by Formula E-1 may be any compound selected from Compound E1 to Compound E19.

[0447]

[0448]

[0449] In an embodiment, the emission layer EML may include a compound represented by Formula E-2a or Formula E-2b. The compound represented by Formula E-2a or Formula E-2b may be used as a phosphorescent host material.

[0450] [Formula E-2a]

[0451]

[0452] In formula E-2a, a may be an integer from 0 to 10; La may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. On the other hand, if "a" is an integer of 2 or more, a plurality of La may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0453] In formula E-2a, A 1 To A 5 can be independently N or C (R i ). In Formula E-2a, R a To R i Each of them may be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and may optionally be combined with adjacent groups to form a ring. For example, R a To R i It may combine with an adjacent group to form a hydrocarbon ring or a heterocyclic ring including N, O, S, etc. as a ring-constituting atom.

[0454] In formula E-2a, A 1 To A 5 Two or three of them can be N, and A 1 To A 5 The rest of the parts in may be independently C(R i ).

[0455] [Formula E-2b]

[0456]

[0457] In Formula E-2b, Cbz1 and Cbz2 may each independently be an unsubstituted carbazolyl group or a carbazolyl group substituted with an aromatic group having 6 to 30 ring carbon atoms. b It may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In Formula E-2b, b may be an integer from 0 to 10, and if b is 2 or more, multiple L b The groups may each independently be a substituted or unsubstituted arylene group of 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group of 2 to 30 ring carbon atoms.

[0458] The compound represented by Formula E-2a or Formula E-2b may be any one compound selected from Compound Group E-2. However, the compounds shown in Compound Group E-2 are merely examples, and the compounds represented by Formula E-2a or Formula E-2b are not limited to Compound Group E-2.

[0459] [Compound Group E-2]

[0460]

[0461]

[0462] The emission layer EML may also include common materials in the related field as a host material. For example, the emission layer EML may include at least one of bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide (POPCPA), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-bis(N-carbazolyl)benzene (mCP), 2,8-bis(diphenylphosphino)dibenzo[b,d]furan (PPF), 4,4',4"-tri(carbazol-9-yl)triphenylamine (TCTA), and 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi) as a host material. However, the embodiment is not limited thereto. For example, tris(8-hydroxyquinoline)aluminum (Alq 3 )、9,10-di(naphthalene-2-yl)anthracene (ADN), 2-tert-butyl-9,10-di(naphthalene-2-yl)anthracene (TBADN), distyryl arylide (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH 2), hexaphenylcyclotrisiloxane (DPSiO 3 ), octaphenylcyclotetrasiloxane (DPSiO 4 ) etc. can be used as the main material.

[0463] In an embodiment, the emission layer EML may include a compound represented by Formula Ma. The compound represented by Formula Ma may be used as a phosphorescent dopant material.

[0464] [Formula Ma]

[0465]

[0466] In formula Ma, Y 1 To Y 4 and Z 1 To Z 4 can be independently C(R 1 ) or N; and R 1 To R 4 Can be hydrogen atom, deuterium atom, substituted or unsubstituted amine group, substituted or unsubstituted sulfenyl group, substituted or unsubstituted oxy group, substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms or substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and can be combined with adjacent groups to form a ring. In formula Ma, m can be 0 or 1, and n can be 2 or 3. In formula Ma, if m is 0, n can be 3, and if m is 1, n can be 2.

[0467] The compound represented by the formula Ma may be any compound selected from the group consisting of compounds M-a1 to M-a25. However, compounds M-a1 to M-a25 are merely examples, and the compound represented by the formula Ma is not limited to the compounds represented by compounds M-a1 to M-a25.

[0468]

[0469]

[0470]

[0471] In an embodiment, the emission layer EML may further include a compound represented by any one of Formulas Fa to Fc. The compound represented by one of Formulas Fa to Fc may be used as a fluorescent dopant material.

[0472] [Formula]

[0473]

[0474] In formula Fa, R a To R j The two of them may be independently substituted with *—NAr 1 Ar 2 Represents a group. a To R j Not by*—NAr 1 Ar 2 The remaining parts of the group substituted by the represented group can be independently hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted amine groups, substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted aryl groups of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl groups of 2 to 30 ring carbon atoms. 1 Ar 2 In the group represented by 1 and Ar 2 and Ar may be independently substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms or substituted or unsubstituted heteroaryl groups having 2 to 30 ring carbon atoms. 1 and Ar 2 At least one of may be a heteroaryl group including O or S as a ring-forming atom.

[0475] [Formula Fb]

[0476]

[0477] In formula Fb, R a and R b Each of Ar and Ar may be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms, and may optionally be combined with adjacent groups to form a ring. 1 To Ar 4 and Ar may be independently substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms or substituted or unsubstituted heteroaryl groups having 2 to 30 ring carbon atoms. 1 To Ar 4 At least one of may be a heteroaryl group including O or S as a ring-forming atom.

[0478] In Formula Fb, U and V may each independently be a substituted or unsubstituted hydrocarbon ring of 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring of 2 to 30 ring carbon atoms.

[0479] In formula Fb, the number of rings represented by U and V may be 0 or 1 independently. If the number of U or V is 1, the fused ring may be present at the portion indicated by U or V, and if the number of U or V is 0, the fused ring may not be present at the portion indicated by U or V. If the number of U is 0 and the number of V is 1, or if the number of U is 1 and the number of V is 0, the fused ring of the fluorene core of formula Fb may be a cyclic compound with four rings. If the number of both U and V is 0, the fused ring of the fluorene core of formula Fb may be a cyclic compound with three rings. If the number of both U and V is 1, the fused ring of the fluorene core of formula Fb may be a cyclic compound with five rings.

[0480] [Formula Fc]

[0481]

[0482] In Formula Fc, A 1 and A 2 can be independently O, S, Se or N (R m ), and R m It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 To R 11 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and may be optionally combined with adjacent groups to form a ring.

[0483] In Formula Fc, A 1 and A 2 Can each independently combine with a substituent of an adjacent ring to form a fused ring. For example, if A 1 and A 2 are independently N(R m ), then A 1 Can be used with R 4 or R 5 combine to form a ring. For example, A 2 Can be used with R 7 or R 8 Combine to form a ring.

[0484] In an embodiment, the emission layer EML may include styryl derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalene-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi) and 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi)), perylene and its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenylbenzene and 1,4-bis(N,N-diphenylamino)pyrene), etc. as dopant materials in the related art.

[0485] The emission layer EML may include a phosphorescent dopant material of the related art. For example, the phosphorescent dopant may use a metal complex including iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) or thulium (Tm). For example, bis (4,6-difluorophenylpyridine-N, C2') pyridine carboxylate iridium (III) (FIrpic), bis (2,4-difluorophenylpyridine)-tetra (1-pyrazolyl) borate iridium (III) (FIr6) or octaethylporphyrin platinum (PtOEP) may be used as a phosphorescent dopant. However, the embodiment is not limited thereto.

[0486] The emission layer EML may include quantum dots.

[0487] In the specification, quantum dots may be crystals of semiconductor compounds. Quantum dots may emit light in various emission wavelengths depending on the size of the crystals. Quantum dots may emit light in various emission wavelengths by controlling the element ratio in the quantum dot compound.

[0488] The diameter of the quantum dot can be, for example, about 1 nm to about 10 nm.

[0489] Quantum dots can be synthesized by chemical bath deposition, metal organic chemical vapor deposition, molecular beam epitaxy or similar processes.

[0490] Chemical bath deposition is a method of mixing an organic solvent and a precursor material and growing quantum dot particle crystals. During the growth of the quantum dot particle crystals, the organic solvent can be used as a dispersant that coordinates on the surface of the quantum dot particle crystals and can control the growth of the quantum dot particle crystals. Therefore, when compared with vapor deposition methods including metal organic chemical vapor deposition (MOCVD) and molecular beam epitaxy (MBE), chemical bath deposition can be more advantageous and can control the growth of quantum dot particle crystals through a low-cost process.

[0491] In an embodiment, the emission layer EML may include a quantum dot material. The quantum dot may be a II-VI group compound, an I-II-VI group compound, an II-IV-VI group compound, an I-II-IV-VI group compound, a III-VI group compound, an I-III-VI group compound, a III-V group compound, a III-II-V group compound, an IV-VI group compound, a II-IV-V group compound, a group IV element, a group IV compound, or any combination thereof.

[0492] Examples of II-VI compounds may include: binary compounds selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof; ternary compounds selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, Cd ZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof; a quaternary compound selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and mixtures thereof; or any combination thereof. Examples of II-VI compounds may also include Group I metals and / or Group IV elements. Examples of I-II-VI compounds may include CuSnS or CuZnS, and II-IV-VI compounds may include ZnSnS, etc. Examples of I-II-IV-VI compounds may include a group consisting of Cu 2 ZnSnS 2 , Cu 2 ZnSnS 4 , Cu 2 ZnSnSe 4 、Ag 2 ZnSnS 2 and any mixture thereof.

[0493] Examples of III-VI compounds may include: binary compounds such as In 2 S 3 andIn 2 Se 3 ; Ternary compounds such as InGaS 3 and InGaSe 3 ; or any combination thereof.

[0494] Examples of I-III-VI group compounds may include: ternary compounds selected from AgInS, AgInS 2 、CuInS、CuInS 2 、AgGaS 2 、CuGaS 2 、CuGaO 2 、AgGaO 2 、AgAlO 2 and mixtures thereof; quaternary compounds such as AgInGaS 2 and CuInGaS 2 ; or any combination thereof.

[0495] Examples of III-V compounds may include: binary compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; ternary compounds selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof; quaternary compounds selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof; or any combination thereof. In an embodiment, the III-V compound may also include a Group II metal. For example, InZnP or the like may be selected as the III-II-V group compound.

[0496] Examples of IV-VI Group compounds may include: binary compounds selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe and mixtures thereof; ternary compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe and mixtures thereof; quaternary compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe and mixtures thereof; or any combination thereof.

[0497] Examples of II-IV-V group compounds may include ternary compounds selected from the group consisting of ZnSnP, ZnSnP2 、ZnSnAs 2 、ZnGeP 2 、ZnGeAs 2 、CdSnP 2 、CdGeP 2 and any mixture thereof.

[0498] Examples of Group IV elements may include Si, Ge, and any mixture thereof. Examples of Group IV compounds may include a binary compound selected from the group consisting of SiC, SiGe, and any mixture thereof.

[0499] Each element included in a multi-element compound (such as a binary compound, a ternary compound, or a quaternary compound) may be present in the particle at a uniform concentration or at a non-uniform concentration. For example, the formula may represent the elements included in the compound, but the element ratio in the compound may vary. For example, AgInGaS 2 Can represent AgIn x Ga 1-x S 2 (x is a real number between 0 and 1).

[0500] In an embodiment, a binary compound, a ternary compound, or a quaternary compound may be present in a particle at a uniform concentration, or may be present in the same particle in a partially different concentration distribution state. In an embodiment, a core / shell structure in which one quantum dot encapsulates another quantum dot may be feasible. Quantum dots having a core / shell structure may have a concentration gradient in which the concentration of the material present in the shell decreases toward the core.

[0501] In an embodiment, the quantum dot may have the above-mentioned core / shell structure including a core containing nanocrystals and a shell surrounding the core. The shell of the quantum dot may be used as a protective layer for preventing chemical deformation of the core to maintain semiconductor properties and / or may be used as a charged layer for imparting electrophoretic properties to the quantum dot. The shell may have a single layer or multiple layers. Examples of the shell of the quantum dot may include metal oxides, non-metal oxides, semiconductor compounds, or any combination thereof.

[0502] Examples of metal oxides or non-metal oxides may include binary compounds such as SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3 , Mn 3 O 4 , CuO, FeO, Fe 2 O 3 , Fe 3 O4 , CoO, Co 3 O 4 and NiO; ternary compounds such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 and CoMn 2 O 4 ; or any combination thereof, but the embodiments are not limited thereto.

[0503] Examples of semiconductor compounds may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc., but embodiments are not limited thereto.

[0504] The quantum dots may have a full width at half maximum (FWHM) of an emission wavelength spectrum equal to or less than about 45 nm. For example, the quantum dots may have a FWHM of an emission wavelength spectrum equal to or less than about 40 nm. For example, the quantum dots may have a FWHM of an emission wavelength spectrum equal to or less than about 30 nm. Within any of the above ranges, color purity or color reproducibility may be improved. Light emitted via such quantum dots may be emitted in all directions, so that a wide viewing angle may be improved.

[0505] The shape of the quantum dot can be a shape commonly used in the relevant field without specific limitation. For example, the quantum dot can have a spherical shape, a pyramidal shape, a multi-arm shape or a cubic shape, and the quantum dot can be in the form of nanoparticles, nanotubes, nanowires, nanofibers, nanoplates, etc.

[0506] When the size of the quantum dot or the ratio of the elements in the quantum dot compound is adjusted, the band gap can be controlled accordingly to obtain light of various wavelengths from the quantum dot emission layer. Therefore, by using quantum dots as described above (e.g., using quantum dots of different sizes or with different element ratios in the quantum dot compound), a light-emitting device that emits light of various wavelengths can be obtained. For example, the size of the quantum dot or the ratio of the elements in the quantum dot compound can be adjusted to emit red light, green light and / or blue light. For example, quantum dots can be configured to emit white light by combining light of various colors.

[0507] In the light emitting element ED according to the embodiment, as Figures 3 to 6As shown in each of the above, the electron transport region ETR may be disposed on the emission layer EML. The electron transport region ETR may include at least one of the hole blocking layer HBL, the electron transport layer ETL, and the electron injection layer EIL. However, the embodiment is not limited thereto.

[0508] The electron transport region ETR may be a layer composed of a single material, a layer including different materials, or a structure having a plurality of layers including different materials.

[0509] For example, the electron transport region ETR may have a single layer structure of an electron injection layer EIL or an electron transport layer ETL, or may have a single layer structure formed using an electron injection material and an electron transport material. In other embodiments, the electron transport region ETR may have a single layer structure formed of a plurality of different materials, or an electron transport layer ETL / electron injection layer EIL or a hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL structure stacked from the emission layer EML without limitation. The thickness of the electron transport region ETR may be, for example, about 100 Å to 200 Å. to about within the range.

[0510] The electron transport region ETR may be formed using various methods such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and a laser induced thermal imaging (LITI) method.

[0511] In the light emitting element ED according to the embodiment, the electron transport region ETR may include a compound represented by Formula ET-2.

[0512] [Formula ET-2]

[0513]

[0514] In formula ET-2, X 1 To X 3 At least one of them can be N, and X 1 To X 3 The rest of the parts in may be independently C(R a ). In formula ET-2, R a It can be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms. 1 To Ar 3Each of them may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0515] In Formula ET-2, a to c may each independently be an integer from 0 to 10. In Formula ET-2, L 1 To L 3 Each of a to c is independently 2 or more, and L may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. 1 To L 3 Each of them may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0516] The electron transport region ETR may include an anthracene-based compound. However, the embodiment is not limited thereto, and the electron transport region ETR may include, for example, tris(8-hydroxyquinoline)aluminum (Alq 3 ), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-di Phenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole ( t Bu-PBD), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinoline-10-hydroxy)beryllium (Bebq 2 ), 9,10-di(naphthalene-2-yl)anthracene (ADN), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB), 4'-(4-(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)naphthalen-1-yl)-[1,1'-biphenyl]-4-carbonitrile (CNNPTRZ), or any mixture thereof without limitation.

[0517] In an embodiment, the electron transport region ETR may include any one of the compounds in compound group 3 .

[0518] In an embodiment, the electron transport region ETR may include at least one of compounds ET1 to ET36.

[0519]

[0520]

[0521]

[0522]

[0523] The electron transport region ETR may include: a metal halide such as LiF, NaCl, CsF, RbCl, RbI, CuI, and KI; a lanthanide metal such as Yb; or a co-deposited material of a metal halide and a lanthanide metal. For example, the electron transport region ETR may include KI:Yb, RbI:Yb, LiF:Yb, etc. as a co-deposited material. The electron transport region ETR may include a metal oxide such as Li 2 O and BaO) or 8-hydroxy-quinoline lithium (Liq). However, the embodiment is not limited thereto. The electron transport region ETR may also include a mixture material of an electron transport material and an insulating organic metal salt. The organic metal salt may be a material having an energy band gap greater than or equal to about 4 eV. For example, the organic metal salt may include, for example, a metal acetate, a metal benzoate, a metal acetoacetate, a metal acetylacetonate, or a metal stearate.

[0524] In addition to the above materials, the electron transport region ETR may include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1), and 4,7-diphenyl-1,10-phenanthroline (Bphen). However, the embodiment is not limited thereto.

[0525] The electron transport region ETR may include a compound of the electron transport region ETR in at least one of the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.

[0526] If the electron transport region ETR includes an electron transport layer ETL, the thickness of the electron transport layer ETL may be about 1000 nm. to about For example, the electron transport layer ETL may have a thickness of about to about If the thickness of the electron transport layer ETL satisfies any one of the above ranges, satisfactory electron transport properties can be obtained without significantly increasing the driving voltage. If the electron transport region ETR includes an electron injection layer EIL, the thickness of the electron injection layer EIL can be about to about For example, the thickness of the electron injection layer EIL can be about to about If the thickness of the electron injection layer EIL satisfies any one of the above ranges, satisfactory electron injection properties can be obtained without causing a significant increase in driving voltage.

[0527] The second electrode EL2 may be disposed on the electron transport region ETR. The second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anode, but the embodiment is not limited thereto. For example, if the first electrode EL1 is an anode, the second electrode EL2 may be a cathode, and if the first electrode EL1 is a cathode, the second electrode EL2 may be an anode.

[0528] The second electrode EL2 may be a transmissive electrode, a transflective electrode, or a reflective electrode. If the second electrode EL2 is a transmissive electrode, the second electrode EL2 may include a transparent metal oxide (eg, ITO, IZO, ZnO, ITZO, etc.).

[0529] If the second electrode EL2 is a transflective electrode or a reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, W, compounds thereof, mixtures thereof (e.g., AgMg, AgYb or MgYb), or a material having a multilayer structure such as LiF / Ca or LiF / Al. In an embodiment, the second electrode EL2 may have a multilayer structure including a reflective layer or a transflective layer formed of the above materials and a transparent conductive layer formed of ITO, IZO, ZnO, ITZO, etc. For example, the second electrode EL2 may include the above metal materials, a combination of two or more metal materials selected from the above metal materials, or an oxide of the above metal materials.

[0530] Although not shown in the drawings, the second electrode EL2 may be electrically connected to the auxiliary electrode. If the second electrode EL2 is electrically connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

[0531] In an embodiment, the light emitting element ED may further include a cover layer CPL disposed on the second electrode EL2. The cover layer CPL may be a multi-layer or a single layer.

[0532] In an embodiment, the cover layer CPL may include an organic layer or an inorganic layer. For example, if the cover layer CPL includes an inorganic material, the inorganic material may include an alkali metal compound (such as LiF), an alkaline earth metal compound (such as MgF 2 )、SiON、SiN x 、SiO y wait.

[0533] For example, if the cover layer CPL includes an organic material, the organic material may include 2,2'-dimethyl-N,N'-di[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl-4,4'-diamine (α-NPD), NPB, TPD, m-MTDATA, Alq 3 , CuPc, N4,N4,N4',N4'-tetrakis(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), etc., or epoxy resin or acrylate such as methacrylate. In an embodiment, the cover layer CPL may include at least one of compounds P1 to P5, but embodiments are not limited thereto.

[0534]

[0535]

[0536] The refractive index of the cover layer CPL may be greater than or equal to about 1.6. For example, the refractive index of the cover layer CPL with respect to light in a wavelength range of about 550 nm to about 660 nm may be greater than or equal to about 1.6.

[0537] Figures 7 to 10 are schematic cross-sectional views of display devices DD-a, DD-TD, DD-b, and DD-c according to the embodiments. Figures 7 to 10 In explaining the display device according to the embodiment, the above reference will not be explained. Figures 1 to 6 Features have been described, and different features will be described.

[0538] Reference Figure 7 , the display device DD-a according to the embodiment may include a display panel DP including a display device layer DP-ED, a light control layer CCL disposed on the display panel DP, and a color filter layer CFL.

[0539] exist Figure 7 In the embodiment shown in , the display panel DP may include a base layer BS, a circuit layer DP-CL disposed on the base layer BS, and a display device layer DP-ED, and the display device layer DP-ED may include a light emitting element ED.

[0540] The light emitting element ED may include a first electrode EL1, a hole transport region HTR disposed on the first electrode EL1, an emission layer EML disposed on the hole transport region HTR, an electron transport region ETR disposed on the emission layer EML, and a second electrode EL2 disposed on the electron transport region ETR. Figure 7 The structure of the light emitting element shown in the figure can be the same as that described herein according to Figures 3 to 6 The structure of one of the light emitting elements is the same as the structure of the other.

[0541] The emission layer EML of the light emitting element ED included in the display device DD-a according to the embodiment may include the above-described condensed polycyclic compound according to the described embodiment.

[0542] Reference Figure 7 , the emission layer EML can be set in the opening OH defined in the pixel defining film PDL. For example, the emission layer EML separated by the pixel defining film PDL and correspondingly provided to each of the light-emitting regions PXA-R, PXA-G and PXA-B can emit light in the same wavelength region. In the display device DD-a, the emission layer EML can emit blue light. Although not shown in the drawings, in an embodiment, the emission layer EML can be set as a common layer for each of the light-emitting regions PXA-R, PXA-G and PXA-B.

[0543] The light control layer CCL may be disposed on the display panel DP. The light control layer CCL may include a light converter. The light converter may be a quantum dot or a phosphor. The light converter may convert the wavelength of the provided light and emit the resulting light. For example, the light control layer CCL may be a layer including quantum dots or a layer including phosphors.

[0544] The light-control layer CCL may include a plurality of light-control parts CCP1, CCP2, and CCP3. The light-control parts CCP1, CCP2, and CCP3 may be separated from each other.

[0545] Reference Figure 7 , the separation pattern BMP may be disposed between the separated light-control parts CCP1, CCP2, and CCP3, but the embodiment is not limited thereto. Figure 7 , the separation pattern BMP is illustrated as not overlapping the light-control parts CCP1 , CCP2 , and CCP3 , but edges of the light-control parts CCP1 , CCP2 , and CCP3 may overlap at least a portion of the separation pattern BMP.

[0546] The light control layer CCL may include a first light control part CCP1, a second light control part CCP2, and a third light control part CCP3, the first light control part CCP1 including a first quantum dot QD1 that converts the first color light provided from the light emitting element ED into the second color light, the second light control part CCP2 including a second quantum dot QD2 that converts the first color light into the third color light, and the third light control part CCP3 transmits the first color light. In an embodiment, the first light control part CCP1 may provide red light as the second color light, and the second light control part CCP2 may provide green light as the third color light. The third light control part CCP3 may transmit and provide blue light as the first color light provided from the light emitting element ED. For example, the first quantum dot QD1 may be a red quantum dot, and the second quantum dot QD2 may be a green quantum dot. The quantum dots QD1 and QD2 may both be quantum dots as described herein.

[0547] The light control layer CCL may further include a scatterer SP. The first light control part CCP1 may include first quantum dots QD1 and scatterers SP, the second light control part CCP2 may include second quantum dots QD2 and scatterers SP, and the third light control part CCP3 may not include quantum dots but may include scatterers SP.

[0548] The scatterer SP may be inorganic particles. For example, the scatterer SP may include TiO 2 、ZnO、Al 2 O 3 、SiO 2 and hollow silica. The scatterer SP may include TiO 2 、ZnO、Al 2 O 3 、SiO 2 and hollow silica, or the scatterer SP may be selected from TiO 2 、ZnO、Al 2 O 3 、SiO 2 and a mixture of two or more materials in hollow silica.

[0549] The first light control part CCP1, the second light control part CCP2, and the third light control part CCP3 may each include matrix resins BR1, BR2, and BR3 that disperse quantum dots QD1 and QD2 and scatterers SP. In an embodiment, the first light control part CCP1 may include first quantum dots QD1 and scatterers SP dispersed in the first matrix resin BR1, the second light control part CCP2 may include second quantum dots QD2 and scatterers SP dispersed in the second matrix resin BR2, and the third light control part CCP3 may include scatterers SP dispersed in the third matrix resin BR3.

[0550] The matrix resins BR1, BR2 and BR3 may all be media in which quantum dots QD1 and QD2 and scatterers SP are dispersed, and may be composed of various resin compositions, which may generally be referred to as binders. For example, the matrix resins BR1, BR2 and BR3 may be acrylic resins, urethane resins, siloxane resins, epoxy resins, etc. The matrix resins BR1, BR2 and BR3 may be transparent resins. In an embodiment, the first matrix resin BR1, the second matrix resin BR2 and the third matrix resin BR3 may be the same or different from each other.

[0551] The light control layer CCL may include a blocking layer BFL1. The blocking layer BFL1 may play a role in blocking the penetration of moisture and / or oxygen (hereinafter, referred to as "moisture / oxygen"). The blocking layer BFL1 may block the light control parts CCP1, CCP2, and CCP3 from being exposed to moisture / oxygen. The blocking layer BFL1 may cover the light control parts CCP1, CCP2, and CCP3. The color filter layer CFL, which will be explained later, may include a blocking layer BFL2 disposed on the light control parts CCP1, CCP2, and CCP3.

[0552] The barrier layers BFL1 and BFL2 may each include at least one inorganic layer. For example, the barrier layers BFL1 and BFL2 may be formed by including an inorganic material. For example, the barrier layers BFL1 and BFL2 may each independently include silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide and silicon oxynitride or a metal film that ensures light transmittance. The barrier layers BFL1 and BFL2 may also include an organic layer. The barrier layers BFL1 and BFL2 may be composed of a single layer or a plurality of layers.

[0553] In the display device DD-a, the color filter layer CFL may be disposed on the light-controlling layer CCL. The color filter layer CFL may be disposed (eg, directly disposed) on the light-controlling layer CCL. For example, the blocking layer BFL2 may be omitted.

[0554] The color filter layer CFL may include filters CF1, CF2, and CF3. The first to third filters CF1, CF2, and CF3 may each be disposed to correspond to the red, green, and blue light emitting regions PXA-R, PXA-G, and PXA-B, respectively.

[0555] The color filter layer CFL may include a first filter CF1 transmitting a second color light, a second filter CF2 transmitting a third color light, and a third filter CF3 transmitting the first color light. For example, the first filter CF1 may be a red filter, the second filter CF2 may be a green filter, and the third filter CF3 may be a blue filter. The filters CF1, CF2, and CF3 may each include a polymer photosensitive resin and a pigment or dye. The first filter CF1 may include a red pigment or dye, the second filter CF2 may include a green pigment or dye, and the third filter CF3 may include a blue pigment or dye.

[0556] However, the embodiment is not limited thereto, and the third filter CF3 may not include a pigment or dye. The third filter CF3 may include a polymer photosensitive resin and may not include a pigment or dye. The third filter CF3 may be transparent. The third filter CF3 may be formed using a transparent photosensitive resin.

[0557] In an embodiment, the first filter CF1 and the second filter CF2 may both be yellow filters. The first filter CF1 and the second filter CF2 may be provided in one body without distinction.

[0558] Although not shown in the drawings, the color filter layer CFL may further include a light blocking portion (not shown). The light blocking portion (not shown) may be a black matrix. The light blocking portion (not shown) may include an organic light blocking material or an inorganic light blocking material containing a black pigment or a black dye. The light blocking portion (not shown) may prevent a light leakage phenomenon and divide the boundaries between the adjacent filters CF1, CF2, and CF3.

[0559] The base substrate BL may be disposed on the color filter layer CFL. The base substrate BL may provide a base surface on which the color filter layer CFL, the light control layer CCL, etc. are disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiment is not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Although not shown in the drawings, in an embodiment, the base substrate BL may be omitted.

[0560] Figure 8is a schematic cross-sectional view of a portion of a display device DD-TD according to an embodiment. In the display device DD-TD according to an embodiment, the light emitting element ED-BT may include a plurality of light emitting structures OL-B1, OL-B2, and OL-B3. The light emitting element ED-BT may include a first electrode EL1 and a second electrode EL2 disposed opposite to each other. The plurality of light emitting structures OL-B1, OL-B2, and OL-B3 may be stacked in sequence in the thickness direction and disposed between the first electrode EL1 and the second electrode EL2. The light emitting structures OL-B1, OL-B2, and OL-B3 may each include an emission layer EML ( Figure 7 ) and an emission layer EML ( Figure 7 ) of the hole transport region HTR( Figure 7 ) and the electron transport region ETR ( Figure 7 ).

[0561] For example, the light emitting elements ED-BT included in the display devices DD-TD may be light emitting elements having a tandem structure including a plurality of emission layers EML.

[0562] exist Figure 8 In the embodiment shown in , the light emitted from the light emitting structures OL-B1, OL-B2 and OL-B3 may all be blue light. However, the embodiment is not limited thereto, and the wavelength regions of the light emitted from the light emitting structures OL-B1, OL-B2 and OL-B3 may be different from each other. For example, the light emitting element ED-BT including a plurality of light emitting structures OL-B1, OL-B2 and OL-B3 emitting light in different wavelength regions may emit white light.

[0563] The charge generation layers CGL1 and CGL2 may be disposed between adjacent light emitting structures OL-B1, OL-B2, and OL-B3. The charge generation layers CGL1 and CGL2 may each independently include a p-type charge generation layer and / or an n-type charge generation layer.

[0564] At least one of the light emitting structures OL-B1, OL-B2 and OL-B3 included in the display devices DD-TD may include the above-described condensed polycyclic compound according to the embodiment. For example, at least one of the emission layers EML included in the light emitting elements ED-BT may include a condensed polycyclic compound.

[0565] Fig. 9 is a schematic cross-sectional view of a display device DD-b according to the embodiment. Fig.10 is a schematic cross-sectional view of a display device DD-c according to the embodiment.

[0566] Fig. 9is a schematic cross-sectional view of a display device DD-b according to an embodiment. The display device DD-b may include light emitting elements ED-1, ED-2, and ED-3 formed by stacking two emission layers. Figure 2 Compared with the display device DD shown in Fig. 9 The difference of the embodiment shown in at least is that the first to third light-emitting elements ED-1, ED-2 and ED-3 each include two emission layers stacked in the thickness direction. In each of the first to third light-emitting elements ED-1, ED-2 and ED-3, the two emission layers can emit light in the same wavelength region.

[0567] The first light-emitting element ED-1 may include a first red emission layer EML-R1 and a second red emission layer EML-R2. The second light-emitting element ED-2 may include a first green emission layer EML-G1 and a second green emission layer EML-G2. The third light-emitting element ED-3 may include a first blue emission layer EML-B1 and a second blue emission layer EML-B2. The emission auxiliary part OG may be arranged between the first red emission layer EML-R1 and the second red emission layer EML-R2, between the first green emission layer EML-G1 and the second green emission layer EML-G2, and between the first blue emission layer EML-B1 and the second blue emission layer EML-B2.

[0568] The emission auxiliary part OG may be a single layer or a multilayer. The emission auxiliary part OG may include a charge generation layer. For example, the emission auxiliary part OG may include an electron transport region, a charge generation layer, and a hole transport region that may be stacked in this order. The emission auxiliary part OG may be provided as a common layer for all of the first to third light-emitting elements ED-1, ED-2, and ED-3. However, the embodiment is not limited thereto, and the emission auxiliary part OG may be patterned and provided in an opening OH defined in the pixel defining film PDL.

[0569] The first red emission layer EML-R1, the first green emission layer EML-G1, and the first blue emission layer EML-B1 may be disposed between the electron transport region ETR and the emission auxiliary portion OG. The second red emission layer EML-R2, the second green emission layer EML-G2, and the second blue emission layer EML-B2 may be disposed between the emission auxiliary portion OG and the hole transport region HTR.

[0570] For example, the first light-emitting element ED-1 may include a first electrode EL1, a hole transport region HTR, a second red emission layer EML-R2, an emission auxiliary portion OG, a first red emission layer EML-R1, an electron transport region ETR, and a second electrode EL2 stacked in this order. The second light-emitting element ED-2 may include a first electrode EL1, a hole transport region HTR, a second green emission layer EML-G2, an emission auxiliary portion OG, a first green emission layer EML-G1, an electron transport region ETR, and a second electrode EL2 stacked in this order. The third light-emitting element ED-3 may include a first electrode EL1, a hole transport region HTR, a second blue emission layer EML-B2, an emission auxiliary portion OG, a first blue emission layer EML-B1, an electron transport region ETR, and a second electrode EL2 stacked in this order.

[0571] The optical auxiliary layer PL may be disposed on the display device layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL may be disposed on the display panel DP and may control light reflected from external light at the display panel DP. Although not shown in the drawings, in an embodiment, the optical auxiliary layer PL may be omitted from the display device DD-b.

[0572] Included in Fig. 9 At least one emission layer in the display device DD-b of the embodiment shown in FIG. 2 may include the fused polycyclic compound of the above embodiment. For example, at least one of the first blue emission layer EML-B1 and the second blue emission layer EML-B2 may include the fused polycyclic compound according to the embodiment.

[0573] and Figure 8 and Fig. 9 on the contrary, Fig.10The display device DD-c shown in the figure is different at least in that it includes four light emitting structures OL-B1, OL-B2, OL-B3 and OL-C1. The light emitting element ED-CT may include a first electrode EL1 and a second electrode EL2 disposed oppositely and first to fourth light emitting structures OL-B1, OL-B2, OL-B3 and OL-C1 stacked in sequence in the thickness direction between the first electrode EL1 and the second electrode EL2. The third light emitting structure OL-B3, the second light emitting structure OL-B2, the first light emitting structure OL-B1 and the fourth light emitting structure OL-C1 may be stacked in this order in the thickness direction. The charge generation layers CGL1, CGL2 and CGL3 may all be disposed between the first to fourth light emitting structures OL-B1, OL-B2, OL-B3 and OL-C1. For example, the first charge generation layer CGL1 may be disposed between the first light emitting structure OL-B1 and the fourth light emitting structure OL-C1. The second charge generation layer CGL2 may be disposed between the first light emitting structure OL-B1 and the second light emitting structure OL-B2. The third charge generation layer CGL3 may be disposed between the second light emitting structure OL-B2 and the third light emitting structure OL-B3.

[0574] Among the four light emitting structures, the first to third light emitting structures OL-B1, OL-B2, and OL-B3 may each emit blue light, and the fourth light emitting structure OL-C1 may emit green light. However, the embodiment is not limited thereto, and the first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may emit light in different wavelength regions from each other.

[0575] The charge generation layers CGL1 , CGL2 , and CGL3 may each independently include a p-type charge generation layer and / or an n-type charge generation layer.

[0576] At least one of the light emitting structures OL-B1, OL-B2, OL-B3 and OL-C1 included in the display device DD-c according to the embodiment may include the above-mentioned condensed polycyclic compound. For example, in the embodiment, at least one of the light emitting structures OL-B1, OL-B2 and OL-B3 may include the above-mentioned condensed polycyclic compound.

[0577] In an embodiment, the light emitting element ED may include a polycyclic compound represented by Formula 1 in at least one functional layer disposed between the first electrode EL1 and the second electrode EL2, and may exhibit excellent emission efficiency and improved life characteristics. For example, the polycyclic compound may be included in the emission layer EML of the light emitting element ED, and the light emitting element ED may exhibit long life characteristics.

[0578] In an embodiment, the electronic device may include a display device including a plurality of light emitting elements and a control unit for controlling the display device. The electronic device according to the embodiment may be a device activated according to an electrical signal. The electronic device may include a display device according to various embodiments. For example, the electronic device may include a television, a monitor, a large display device (such as an external billboard), but examples of electronic devices may also include small and medium-sized display devices (such as personal computers, laptop computers, personal digital terminals, display devices for automobiles, game consoles, portable electronic devices, and cameras).

[0579] Fig.11 is a schematic perspective view of an automobile AM ​​in which first to fourth display devices DD-1, DD-2, DD-3 and DD-4 are provided. At least one of the first to fourth display devices DD-1, DD-2, DD-3 and DD-4 may have a configuration according to the reference Figure 1 , Figure 2 and Figures 7 to 10 The described embodiment shows a structure of one of the display devices DD, DD-a, DD-TD, DD-b, and DD-c.

[0580] Fig.11 A schematic perspective view of the interior of the automobile AM ​​is shown, but this is only an example, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may be provided on other transport devices such as bicycles, motorcycles, trains, ships, and airplanes. At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may have a structure according to one of the display devices DD, DD-TD, DD-a, DD-b, and DD-c, and according to an embodiment, may be introduced into a personal computer, a laptop computer, a personal digital terminal, a game console, a portable electronic device, a television, a monitor, an external billboard, etc. However, these are provided only as examples, and the display device may be included in other electronic devices.

[0581] At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include a reference Figures 3 to 6 The light emitting element ED according to the embodiment is explained. The light emitting element ED according to the embodiment may include the fused polycyclic compound according to the embodiment. At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include the light emitting element ED including the fused polycyclic compound according to the embodiment, and may show improved display life.

[0582] Reference Fig.11The automobile AM ​​may include a steering wheel HA and a transmission device GR for operation of the automobile AM. The automobile AM ​​may include a front window GL disposed to face the driver.

[0583] The first display device DD-1 may be disposed in a first area overlapping the steering wheel HA. For example, the first display device DD-1 may be a digital cluster that displays first information of the automobile AM. The first information may include a first scale showing the driving speed of the automobile AM, a second scale showing the engine speed (e.g., as revolutions per minute (RPM)), and an image showing the fuel status. The first scale and the second scale may be represented by digital images.

[0584] The second display device DD-2 can be arranged in a second area facing the driver's seat and overlapping with the front window GL. The driver's seat can be a seat provided with a steering wheel HA. For example, the second display device DD-2 can be a head-up display (HUD) showing the second information of the automobile AM. The second display device DD-2 can be optically transparent. The second information can include a digital value showing the driving speed of the automobile AM, and can also include information containing the current time. Although not shown in the accompanying drawings, the second information of the second display device DD-2 can be projected and displayed on the front window GL.

[0585] The third display device DD-3 may be disposed in a third area adjacent to the transmission device GR. For example, the third display device DD-3 may be a central information display (CID) for the automobile AM ​​that is disposed between the driver's seat and the passenger seat and that displays the third information. The passenger seat may be a seat that is separated from the driver's seat, and the transmission device GR is disposed between the passenger seat and the driver's seat. The third information may include information about road conditions (e.g., navigation information), playing music or radio, playing dynamic images (or images), the temperature in the automobile AM, and the like.

[0586] The fourth display device DD-4 may be disposed in a fourth area separated from the steering wheel HA and the transmission device GR and adjacent to the side of the automobile AM. For example, the fourth display device DD-4 may be a digital rearview mirror that displays the fourth information. The fourth display device DD-4 may display an external image of the automobile AM ​​captured by a camera module CM disposed outside the automobile AM. The fourth information may include an external image of the automobile AM.

[0587] The first to fourth information as described herein are examples, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may also display information about the interior and exterior of the automobile AM. The first to fourth information may include information different from each other. However, the embodiment is not limited thereto, and a portion of the first to fourth information may include the same information.

[0588] Hereinafter, a condensed polycyclic compound according to an embodiment and a light emitting element according to an embodiment will be explained with reference to examples and comparative examples. The examples described below are provided only as illustrations to help understand the disclosure, and the scope thereof is not limited thereto.

[0589] [Example]

[0590] 1. Synthesis of fused polycyclic compounds

[0591] The synthesis method of the fused polycyclic compound according to the embodiment will be explained by describing the synthesis method for compound 10, compound 20, compound 21, compound 27, compound 30, compound 40, compound 50, compound 62 and compound 73. The synthesis method of the fused polycyclic compound as explained below is provided only as an example, and the synthesis method of the fused polycyclic compound according to the embodiment is not limited to the following example.

[0592] (1) Synthesis of Compound 10

[0593] (Synthesis of Intermediate 10-a)

[0594]

[0595] Under argon atmosphere, 1,3-dibromo-5-(tert-butyl)benzene (10 g, 34 mmol), 3-phenyldibenzo[b,d]furan-4-amine (17.7 g, 68 mmol), pd 2 dba 3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (P(t-Bu) 3 , 1.6 mL, 3.8 mmol) and sodium tert-butoxide (NatBuO, 11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 10-a (white solid, 16 g, 74%).

[0596] ESI-LCMS:[M] + :C 46 H 36 N 2 O 2 .648.2842.

[0597] (Synthesis of Intermediate 10-b)

[0598]

[0599] Under argon atmosphere, intermediate 10-a (16 g, 25 mmol), 1-chloro-3-iodobenzene-2,4,5,6-d4 (12 g, 50 mmol), Pd 2 dba 3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 10-b (white solid, 15 g, 70%).

[0600] ESI-LCMS:[M] + :C 58 H 34 D 8 Cl 2 N 2 O 2 .876.0310.

[0601] (Synthesis of Intermediate 10-c)

[0602]

[0603] Under argon atmosphere, intermediate 10-b (15 g, 17 mmol) was added to a 1 L flask and dissolved in 200 mL of o-dichlorobenzene, to which BBr was added. 3(1.5 equivalents). The reaction solution was stirred at about 140 degrees for about 12 hours. After cooling, triethylamine was added to quench the reaction, the solvent was removed under reduced pressure, and the reaction mixture was stirred for about 12 hours at about 140 degrees. 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 10-c (yellow solid, 3.8 g, 21%).

[0604] ESI-LCMS:[M] + :C 58 H 33 D 6 BCl 2 N 2 O 2 .882.2099.

[0605] (Synthesis of Compound 10)

[0606]

[0607] Under argon atmosphere, intermediate 10-c (3.8 g, 4.3 mmol), 3-(phenyl-d5)-9H-carbazole-1,2,4,5,6,7,8-d7 (2.2 g, 8.6 mmol), Pd 2 dba 3 (0.06 g, 0.12 mmol), tri-tert-butylphosphine (0.06 mL, 0.24 mmol) and sodium tert-butoxide (0.5 g, 5.1 mmol) were added to a 1 L flask and dissolved in 100 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Compound 10 (yellow solid, 4.2 g, 74%).

[0608] ESI-LCMS:[M] + :C 94 H 33 D 30 BN 4 O 2 .1320.6907

[0609] 1H-NMR (CDCl 3): d=7.98(d,4H),7.78(d,2H),7.69(d,2H),7.54(d,2H),7.43(m,10H),7.04(d,4H),6.92(s,2H),1.39(s,18H).

[0610] (2) Synthesis of Compound 20

[0611] (Synthesis of Intermediate 20-a)

[0612]

[0613] Under argon atmosphere, 1,3-dibromo-5-(tert-butyl)benzene (10 g, 34 mmol), 2-phenyldibenzo[b,d]furan-1,3,6,7,8,9-d6-4-amine (18 g, 68 mmol), Pd 2 dba 3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 20-a (white solid, 17.3 g, 77%).

[0614] ESI-LCMS:[M] + :C 46 H 24 D 12 N 2 O 2 .660.3512.

[0615] (Synthesis of Intermediate 20-b)

[0616]

[0617] Under argon atmosphere, intermediate 20-a (17 g, 25.7 mmol), 1-chloro-3-iodobenzene-2,4,5,6-d4 (12 g, 50 mmol), Pd 2 dba 3(1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 20-b (white solid, 16.6 g, 73%).

[0618] ESI-LCMS:[M] + :C 58 H 22 D 20 Cl 2 N 2 O 2 .888.3935.

[0619] (Synthesis of Intermediate 20-c)

[0620]

[0621] Under argon atmosphere, intermediate 20-b (16 g, 18 mmol) was added to a 1 L flask and dissolved in 200 mL of o-dichlorobenzene, to which BBr was added. 3 (1.5 equivalents). The reaction solution was stirred at about 140 degrees for about 12 hours. After cooling, triethylamine was added to quench the reaction, the solvent was removed under reduced pressure, and the reaction mixture was stirred for about 12 hours at about 140 degrees. 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 20-c (yellow solid, 3.7 g, 23%).

[0622] ESI-LCMS:[M] + :C 58 H 21 D 18 BCl 2 N 2 O 2 .894.6033.

[0623] (Synthesis of Compound 20)

[0624]

[0625] Under argon atmosphere, intermediate 20-c (3.7 g, 4.1 mmol), 3-phenyl-9H-carbazole-1,2,4,5,6,7,8-d7 (2.1 g, 8.2 mmol), Pd 2 dba 3 (0.06 g, 0.12 mmol), tri-tert-butylphosphine (0.06 mL, 0.24 mmol) and sodium tert-butoxide (0.5 g, 5.1 mmol) were added to a 1 L flask and dissolved in 100 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4% paraformaldehyde and hexane as a developing solution to obtain Compound 20 (yellow solid, 4 g, 75%).

[0626] ESI-LCMS:[M] + :C 94 H 31 D 32 BN 4 O 2 .1322.7170

[0627] 1H-NMR (CDCl 3 ): d=7.45(m,20H),7.01(s,2H),1.32(s,18H).

[0628] (3) Synthesis of Compound 21

[0629] (Synthesis of Intermediate 21-a)

[0630]

[0631] Under argon atmosphere, 1,3-dibromo-5-(tert-butyl)benzene (10 g, 34 mmol), 1,3-diphenyldibenzo[b,d]furan-2,6,7,8,9-d5-4-amine (23 g, 68 mmol), Pd 2 dba 3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 21-a (white solid, 20 g, 72%).

[0632] ESI-LCMS:[M] + :C 58 H 34 D 10 N 2 O 2 .810.4104.

[0633] (Synthesis of Intermediate 21-b)

[0634]

[0635] Under argon atmosphere, intermediate 21-a (20 g, 25 mmol), 1-chloro-3-iodobenzene-2,4,5,6-d4 (12 g, 50 mmol), Pd 2 dba 3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 21-b (white solid, 18 g, 70%).

[0636] ESI-LCMS:[M] + :C 70 H 32 D 18 Cl 2 N 2 O 2 .1038.4471.

[0637] (Synthesis of Intermediate 21-c)

[0638]

[0639] Under argon atmosphere, intermediate 21-b (18 g, 17 mmol) was added to a 1 L flask and dissolved in 200 mL of o-dichlorobenzene, to which BBr was added. 3 (1.5 equivalents). The reaction solution was stirred at about 140 degrees for about 12 hours. After cooling, triethylamine was added to quench the reaction, the solvent was removed under reduced pressure, and the reaction mixture was stirred for about 12 hours at about 140 degrees. 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4%> H2SO4 and hexane as a developing solution to obtain Intermediate 21-c (yellow solid, 4 g, 22%).

[0640] ESI-LCMS:[M] + :C 70 H 31 D 16 BCl 2 N 2 O 2 .1044.4001.

[0641] (Synthesis of Compound 21)

[0642]

[0643] Under argon atmosphere, intermediate 21-c (4 g, 3.8 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.3 g, 7.6 mmol), Pd 2 dba 3 (0.06 g, 0.12 mmol), tri-tert-butylphosphine (0.06 mL, 0.24 mmol) and sodium tert-butoxide (0.5 g, 5.1 mmol) were added to a 1 L flask and dissolved in 100 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4% paraformaldehyde and hexane as a developing solution to obtain Compound 21 (yellow solid, 3.5 g, 71%).

[0644] ESI-LCMS:[M] + :C 94 H 31 D 32 BN 4 O 2 .1322.7170

[0645] 1H-NMR (CDCl 3 ): d=7.51(m,20H),6.98(s,2H),1.34(s,18H).

[0646] (4) Synthesis of Compound 27

[0647] (Synthesis of Intermediate 27-a)

[0648]

[0649] Under argon atmosphere, 1,3-dibromo-5-(tert-butyl)benzene (10 g, 34 mmol), 3,7-diphenyldibenzo[b,d]furan-1,2,6,8,9-d5-4-amine (23 g, 68 mmol), Pd 2 dba 3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 27-a (white solid, 22.8 g, 83%).

[0650] ESI-LCMS:[M] + :C 58 H 34 D 10 N 2 O 2 .810.4030.

[0651] (Synthesis of Intermediate 27-b)

[0652]

[0653] Under argon atmosphere, intermediate 27-a (22 g, 27 mmol), 1-chloro-3-iodobenzene-2,4,5,6-d4 (13 g, 54 mmol), Pd 2 dba 3(1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 27-b (white solid, 15 g, 54%).

[0654] ESI-LCMS:[M] + :C 70 H 32 D 18 Cl 2 N 2 O 2 .1038.4414.

[0655] (Synthesis of Intermediate 27-c)

[0656]

[0657] Under argon atmosphere, intermediate 27-b (15 g, 14.5 mmol) was added to a 1 L flask and dissolved in 150 mL of o-dichlorobenzene, to which BBr was added. 3 (1.5 equivalents). The reaction solution was stirred at about 140 degrees for about 12 hours. After cooling, triethylamine was added to quench the reaction, the solvent was removed under reduced pressure, and the reaction mixture was stirred for about 12 hours at about 140 degrees. 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 27-c (yellow solid, 3.3 g, 22%).

[0658] ESI-LCMS:[M] + :C 70 H 31 D 16 BCl 2 N 2 O 2 .1044.4136.

[0659] (Synthesis of Compound 27)

[0660]

[0661] Under argon atmosphere, intermediate 27-c (3.3 g, 3.1 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.1 g, 6.2 mmol), Pd 2 dba 3 (0.06 g, 0.12 mmol), tri-tert-butylphosphine (0.06 mL, 0.24 mmol) and sodium tert-butoxide (0.5 g, 5.1 mmol) were added to a 1 L flask and dissolved in 100 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4% paraformaldehyde and hexane as a developing solution to obtain Compound 27 (yellow solid, 3.1 g, 77%).

[0662] ESI-LCMS:[M] + :C 94 H 31 D 32 BN 4 O 2 .1322.7007

[0663] 1H-NMR (CDCl 3 ): d=7.51(m,20H),7.06(s,2H),1.32(s,9H).

[0664] (5) Synthesis of Compound 30

[0665] (Synthesis of Intermediate 30-a)

[0666]

[0667] Under argon atmosphere, 1,3-dibromo-5-(tert-butyl)benzene (10 g, 34 mmol), 2,8-diphenyldibenzo[b,d]furan-1,3,6,7,9-d5-4-amine (23 g, 68 mmol), Pd 2 dba 3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 30-a (white solid, 22 g, 80%).

[0668] ESI-LCMS:[M] + :C 58 H 34 D 10 N 2 O 2 .810.3337.

[0669] (Synthesis of Intermediate 30-b)

[0670]

[0671] Under argon atmosphere, intermediate 30-a (22 g, 27 mmol), 1-chloro-3-iodobenzene-2,4,5,6-d4 (13 g, 54 mmol), Pd 2 dba 3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 30-b (white solid, 16 g, 57%).

[0672] ESI-LCMS:[M] + :C 70 H 32 D 18 Cl 2 N 2 O 2 .1038.4814.

[0673] (Synthesis of Intermediate 30-c)

[0674]

[0675] Under argon atmosphere, intermediate 30-b (15 g, 14.5 mmol) was added to a 1 L flask and dissolved in 150 mL of o-dichlorobenzene, to which BBr was added. 3 (1.5 equivalents). The reaction solution was stirred at about 140 degrees for about 12 hours. After cooling, triethylamine was added to quench the reaction, the solvent was removed under reduced pressure, and the reaction mixture was stirred for about 12 hours at about 140 degrees. 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 30-c (yellow solid, 2.87 g, 19%).

[0676] ESI-LCMS:[M] + :C 70 H 31 D 16 BCl 2 N 2 O 2 .1044.1113.

[0677] (Synthesis of Compound 30)

[0678]

[0679] Under argon atmosphere, intermediate 30-c (2.5 g, 2.4 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.84 g, 4.8 mmol), Pd 2 dba 3 (0.06 g, 0.12 mmol), tri-tert-butylphosphine (0.06 mL, 0.24 mmol) and sodium tert-butoxide (0.5 g, 5.1 mmol) were added to a 1 L flask and dissolved in 100 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4% paraformaldehyde and hexane as a developing solution to obtain Compound 30 (yellow solid, 2.3 g, 73%).

[0680] ESI-LCMS:[M] + :C 94 H 31 D 32 BN 4 O 2 .1322.6952

[0681] 1H-NMR (CDCl 3 ): d=7.43(m,20H),6.96(s,2H),1.38(s,9H).

[0682] (6) Synthesis of Compound 40

[0683] (Synthesis of Intermediate 40-a)

[0684]

[0685] Under argon atmosphere, 1,3-dibromo-5-(tert-butyl)benzene (10 g, 34 mmol), 1-(tert-butyl)-3-(phenyl-d5)-dibenzo[b,d]furan-2,6,7,8,9-d5-4-amine (22 g, 68 mmol), Pd 2 dba 3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 40-a (white solid, 19 g, 73%).

[0686] ESI-LCMS:[M] + :C 54 H 32 D 20 N 2 O 2 .780.5234.

[0687] (Synthesis of Intermediate 40-b)

[0688]

[0689] Under argon atmosphere, intermediate 40-a (19 g, 24 mmol), 1-chloro-3-iodobenzene-2,4,5,6-d4 (12 g, 50 mmol), Pd 2 dba 3(1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 40-b (white solid, 17.6 g, 72%).

[0690] ESI-LCMS:[M] + :C 66 H 30 D 28 Cl 2 N 2 O 2 .1008.5635.

[0691] (Synthesis of Intermediate 40-c)

[0692]

[0693] Under argon atmosphere, intermediate 40-b (17.6 g, 17 mmol) was added to a 1 L flask and dissolved in 200 mL of o-dichlorobenzene, to which BBr was added. 3 (1.5 equivalents). The reaction solution was stirred at about 140 degrees for about 12 hours. After cooling, triethylamine was added to quench the reaction, the solvent was removed under reduced pressure, and the reaction mixture was stirred for about 12 hours at about 140 degrees. 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 40-c (yellow solid, 3.7 g, 21%).

[0694] ESI-LCMS:[M] + :C 66 H 29 D 26 BCl 2 N 2 O 2 .1014.5437.

[0695] (Synthesis of Compound 40)

[0696]

[0697] Under argon atmosphere, intermediate 40-c (3.7 g, 3.6 mmol), 3-(phenyl-d5)-9H-carbazole-1,2,4,5,6,7,8-d7 (1.9 g, 7.2 mmol), Pd 2 dba 3 (0.06 g, 0.12 mmol), tri-tert-butylphosphine (0.06 mL, 0.24 mmol) and sodium tert-butoxide (0.5 g, 5.1 mmol) were added to a 1 L flask and dissolved in 100 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4% paraformaldehyde and hexane as a developing solution to obtain Compound 40 (yellow solid, 3.7 g, 70%).

[0698] ESI-LCMS:[M] + :C 102 H 29 D 50 BN 4 O 2 .1452.3694

[0699] (7) Synthesis of Compound 50

[0700] (Synthesis of Intermediate 50-a)

[0701]

[0702] Under argon atmosphere, 2-(3,5-dibromophenyl)-dibenzo[b,d]furan (10 g, 25 mmol), 2-phenyldibenzo[b,d]furan-1,3,6,7,8,9-d6-4-amine (13 g, 50 mmol), Pd 2 dba 3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 50-a (white solid, 14.5 g, 75%).

[0703] ESI-LCMS:[M] + :C 54 H 22 D 12 N 2 O 3 .770.3233.

[0704] (Synthesis of Intermediate 50-b)

[0705]

[0706] Under argon atmosphere, intermediate 50-a (14 g, 18 mmol), 1-chloro-3-iodobenzene-2,4,5,6-d4 (12 g, 50 mmol), Pd 2 dba 3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 50-b (white solid, 12.7 g, 70%).

[0707] ESI-LCMS:[M] + :C 66 H 20 D 20 Cl 2 N 2 O 3 .998.3711.

[0708] (Synthesis of Intermediate 50-c)

[0709]

[0710] Under argon atmosphere, intermediate 50-b (12 g, 12 mmol) was added to a 1 L flask and dissolved in 150 mL of o-dichlorobenzene, to which BBr was added. 3(1.5 equivalents). The reaction solution was stirred at about 140 degrees for about 12 hours. After cooling, triethylamine was added to quench the reaction, the solvent was removed under reduced pressure, and the reaction mixture was stirred for about 12 hours at about 140 degrees. 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 50-c (yellow solid, 2.9 g, 24%).

[0711] ESI-LCMS:[M] + :C 66 H 19 D 18 BCl 2 N 2 O 3 .1004.7348.

[0712] (Synthesis of Compound 50)

[0713]

[0714] Under argon atmosphere, intermediate 50-c (2.9 g, 2.8 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.1 g, 5.6 mmol), Pd 2 dba 3 (0.06 g, 0.12 mmol), tri-tert-butylphosphine (0.06 mL, 0.24 mmol) and sodium tert-butoxide (0.5 g, 5.1 mmol) were added to a 1 L flask and dissolved in 100 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4% paraformaldehyde and hexane as a developing solution to obtain Compound 50 (yellow solid, 2.6 g, 73%).

[0715] ESI-LCMS:[M] + :C 90 H 19 D 34 BN 4 O 3 .1282.6137

[0716] 1H-NMR (CDCl 3): d=7.98(d,1H),7.80(m,3H),7.43(m,10H),7.32(m,3H),6.99(s,2H).

[0717] (8) Synthesis of Compound 62

[0718] (Synthesis of Intermediate 62-a)

[0719]

[0720] Under argon atmosphere, N-(3-bromo-5-(tert-butyl)phenyl)-5'-(tert-butyl)-[1,1':3',1"-terphenyl]-2'-amine (10 g, 20 mmol), 1-chloro-3-iodobenzene-2,4,5,6-d4 (4.7 g, 20 mmol), Pd 2 dba 3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 62-a (white solid, 9.2 g, 74%).

[0721] ESI-LCMS:[M] + :C 38 H 33 D 4 BrClN.625.2033.

[0722] (Synthesis of Intermediate 62-b)

[0723]

[0724] Under argon atmosphere, intermediate 62-a (9 g, 14 mmol), 1-(tert-butyl)-3-phenyldibenzo[b,d]furan-2,6,7,8,9-d5-4-amine (4.6 g, 14 mmol), Pd 2 dba 3(1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 62-b (white solid, 8.5 g, 70%).

[0725] ESI-LCMS:[M] + :C 60 H 48 D 9 C1N 2 O.865.4763.

[0726] (Synthesis of Intermediate 62-c)

[0727]

[0728] Under argon atmosphere, intermediate 62-b (8.5 g, 10 mmol), 1-chloro-3-iodobenzene-2,4,5,6-d4 (2.4 g, 10 mmol), Pd 2 dba 3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 62-c (white solid, 7.1 g, 73%).

[0729] ESI-LCMS:[M] + :C 66 H 47 D 13 Cl 2 N 2 O.981.2047.

[0730] (Synthesis of Intermediate 62-d)

[0731]

[0732] Under argon atmosphere, intermediate 62-c (7 g, 7.1 mmol) was added to a 1 L flask and dissolved in 150 mL of o-dichlorobenzene, to which BBr was added. 3 (1.5 equivalents). The reaction solution was stirred at about 140 degrees for about 12 hours. After cooling, triethylamine was added to quench the reaction, the solvent was removed under reduced pressure, and the reaction mixture was stirred for about 12 hours at about 140 degrees. 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 62-d (yellow solid, 1.8 g, 26%).

[0733] ESI-LCMS:[M] + :C 66 H 46 D 11 BCl 2 N 2 O.985.4677.

[0734] (Synthesis of Compound 62)

[0735]

[0736] Under argon atmosphere, intermediate 62-d (1.8 g, 1.8 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.6 g, 3.6 mmol), Pd 2 dba 3 (0.06 g, 0.12 mmol), tri-tert-butylphosphine (0.06 mL, 0.24 mmol) and sodium tert-butoxide (0.5 g, 5.1 mmol) were added to a 1 L flask and dissolved in 100 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4% paraformaldehyde and hexane as a developing solution to obtain Compound 62 (yellow solid, 1.7 g, 76%).

[0737] ESI-LCMS:[M] + :C 90 H46 D 27 BN 4 O.1263.6761

[0738] 1H-NMR (CDCl 3 ): d=7.44(s,2H),7.43(m,11H),7.08(m,4H),6.93(s,2H).

[0739] (9) Synthesis of Compound 73

[0740] (Synthesis of Intermediate 73-a)

[0741]

[0742] Under argon atmosphere, 1,3-dibromo-5-(tert-butyl)benzene (10 g, 34 mmol), 1-(tert-butyl)-3-(phenyl-d5)dibenzo[b,d]furan-2,6,7,8,9-d5-4-amine (22 g, 68 mmol), Pd 2 dba 3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 73-a (white solid, 19 g, 72%).

[0743] ESI-LCMS:[M] + :C 54 H 32 D 20 N 2 O 2 .780.5320.

[0744] (Synthesis of Intermediate 73-b)

[0745]

[0746] Under argon atmosphere, intermediate 73-a (19 g, 24 mmol), 1-chloro-3-iodobenzene-2,4,5,6-d4 (5.9 g, 24 mmol), Pd 2 dba3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 73-b (white solid, 14 g, 65%).

[0747] ESI-LCMS:[M] + :C 60 H 31 D 24 C1N 2 O 2 .894.5535.

[0748] (Synthesis of Intermediate 73-c)

[0749]

[0750] Under argon atmosphere, intermediate 73-b (14 g, 15 mmol), 3-bromo-4'-iodo-1,1'-biphenyl-2',3',5',6'-d4 (5.7 g, 15 mmol), Pd 2 dba 3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 73-c (white solid, 13 g, 77%).

[0751] ESI-LCMS:[M] + :C 72 H 34 D 28 BrClN2 O 2 .1128.5403.

[0752] (Synthesis of Intermediate 73-d)

[0753]

[0754] Under argon atmosphere, intermediate 73-c (13 g, 11.5 mmol) was added to a 1 L flask and dissolved in 150 mL of o-dichlorobenzene, to which BBr was added. 3 (1.5 equivalents). The reaction solution was stirred at about 140 degrees for about 12 hours. After cooling, triethylamine was added to quench the reaction, the solvent was removed under reduced pressure, and the reaction mixture was stirred for about 12 hours at about 140 degrees. 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 73-d (yellow solid, 3.1 g, 24%).

[0755] ESI-LCMS:[M] + :C 72 H 33 D 26 BBrCl 2 O 2 .1134.5237.

[0756] (Synthesis of Intermediate 73-e)

[0757]

[0758] Under argon atmosphere, intermediate 73-d (3 g, 2.6 mmol), triphenylsilane (0.7 g, 2.6 mmol), Pd 2 dba 3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5 g, 120 mmol) were added to a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solution to obtain Intermediate 73-e (white solid, 1.8 g, 54%).

[0759] ESI-LCMS:[M] +:C 90 H 48 D 26 BCN 2 O 2 Si.1314.6953.

[0760] (Synthesis of Compound 73)

[0761]

[0762] Under argon atmosphere, intermediate 73-e (1.8 g, 1.4 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.24 g, 1.4 mmol), Pd 2 dba 3 (0.06 g, 0.12 mmol), tri-tert-butylphosphine (0.06 mL, 0.24 mmol) and sodium tert-butoxide (0.5 g, 5.1 mmol) were added to a 1 L flask and dissolved in 100 mL of o-xylene, and the reaction solution was stirred at about 140 degrees for about 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extracted, and the organic layer was collected and precipitated with anhydrous MgSO 4 The solvent in the filtered solution was removed under reduced pressure, and the mixture was dried and filtered using silica gel and CH 2 Cl 2 The solid thus obtained was separated and purified by column chromatography using 4% paraformaldehyde and hexane as a developing solution to obtain Compound 73 (yellow solid, 1.5 g, 74%).

[0763] ESI-LCMS:[M] + :C 102 H 48 D 34 BN 3 O 2 Si.1453.8490

[0764] 1H-NMR (CDCl 3 ): d=7.88(s,1H),7.64(d,2H),7.46(m,4H),7.35(m,11H),6.95(s,2H),1.35(s,18H),1.22(s,9H).

[0765] 2. Manufacturing and evaluation of light-emitting components

[0766] The light-emitting element of the embodiment including the fused polycyclic compound of the embodiment in the emission layer was manufactured by the following method. The fused polycyclic compounds of Example Compound 10, Example Compound 20, Example Compound 21, Example Compound 27, Example Compound 30, Example Compound 40, Example Compound 50, Example Compound 62 and Example Compound 73 were used as the dopant material of the emission layer to manufacture the light-emitting elements of Examples 1 to 9. Comparative Examples 1 to 8 correspond to the light-emitting elements manufactured using Comparative Compounds C1 to C8 as the dopant material of the emission layer.

[0767] [Example Compounds]

[0768]

[0769] [Comparative Compounds]

[0770]

[0771]

[0772] (Manufacturing of Light Emitting Devices)

[0773] In order to manufacture the light emitting elements of the examples and the comparative examples, a layer of about 15 Ω / cm 2 A glass substrate of an ITO electrode (product of Corning Co.) was cut into a size of about 50 mm×50 mm×0.7 mm, ultrasonically cleaned using isopropyl alcohol and pure water for about 5 minutes each, exposed to ultraviolet rays for about 30 minutes, cleaned by exposure to ozone to form an anode, and the anode was installed in a vacuum deposition device.

[0774] NPD is deposited on the anode to form a A hole injection layer having a thickness of about 1000 nm was formed, and compound H-1-19 was deposited on the hole injection layer to form a hole injection layer having a thickness of about 1000 nm. CzSi is deposited on the hole transport layer to form a hole transport layer having a thickness of about The thickness of the emission auxiliary layer is .

[0775] A host mixture obtained by mixing the second compound and the third compound according to the example in a ratio of about 1:1, the fourth compound, and the example compound or the comparative compound were co-deposited in a weight ratio of about 85:14:1 to form a TSPO1 is deposited on the emission layer to form an emission layer having a thickness of about TPBi is deposited on the hole blocking layer to form a hole blocking layer having a thickness of about An electron transport layer with a thickness of about 1000 nm is formed, and LiF is deposited on the electron transport layer to form a The electron injection layer having a thickness of about A second electrode with a thickness of about 100 mm is formed on the second electrode to form a LiF / Al electrode. The thickness of the covering layer.

[0776] All layers were formed by vacuum deposition. Among the compounds in compound group 2, compound HT1 was used as the second compound. Among the compounds in compound group 3, compound ETH66 was used as the third compound. Among the compounds in compound group 4, compound AD-39 was used as the fourth compound.

[0777] The compounds used to produce the light-emitting elements of Examples and Comparative Examples are shown below. The following materials were used after purchasing commercially available products and performing sublimation purification.

[0778]

[0779] (Evaluation of Physical Properties of Compounds of Examples and Comparative Examples)

[0780] In Table 1, physical properties of Compound 10, Compound 20, Compound 21, Compound 27, Compound 30, Compound 40, Compound 50, Compound 62, and Compound 73 as example compounds and Comparative Compounds C1 to C8 as comparative compounds were evaluated and shown.

[0781] In Table 1, the highest occupied molecular orbital (HOMO) energy level, absorption wavelength (λ Abs ) and emission wavelength (λ emi ), Stokes shift, quarter width of maximum (FWQM) and emission efficiency (photoluminescence quantum yield, PLQY).

[0782] [Table 1]

[0783]

[0784] Referring to Table 1, it can be confirmed that the compounds of Examples 1 to 9 show smaller Stokes shift and higher photoluminescence quantum yield (PLQY) than the compounds of Comparative Examples 1 to 8. Considering the quarter full width peak (FWQM), it can be confirmed that the quarter full width peaks of the example compounds included in Examples 1 to 9 are smaller than the quarter full width peaks of Comparative Compounds C1 to C8 included in Comparative Examples 1 to 8.

[0785] It can be confirmed that the example compounds show emission wavelength (λ emi) blue-shifted wavelength and color purity close to neutral blue. If compared with Examples 1 to 9, it can be confirmed that the emission wavelengths of Comparative Compounds C5 and Comparative Compounds C6 included in Comparative Examples 5 and Comparative Examples 6 are red-shifted. The difference between the example compounds and Comparative Compounds C5 and Comparative Compounds C6 is the connection position of the dibenzofuran moiety to the nitrogen atom. Comparative Compounds C5 and Comparative Compounds C6 include a dibenzofuran moiety that is connected to a fused ring core but not via the carbon at the 4-position of the dibenzofuran moiety but via the carbon at the 2-position or 3-position and is connected to the nitrogen atom, and is red-shifted compared to the example compounds. The example compounds have a structure in which the carbon at the 4-position of the dibenzofuran moiety is connected to the nitrogen atom of the fused ring core, and the emission wavelength can be blue-shifted, and therefore, high color purity can be displayed in the blue light wavelength region. By changing the type of substituents connected to the fused ring core, precise control of the target emission wavelength can be achieved without significantly changing the optical properties and physical properties.

[0786] (Evaluation of properties of light-emitting element)

[0787] The element efficiency and element life of the light-emitting elements manufactured by using Compound 10, Compound 20, Compound 21, Compound 27, Compound 30, Compound 40, Compound 50, Compound 62 and Compound 73 and Comparative Compound C1 to Comparative Compound C8 are evaluated. In Table 2, the evaluation results of the light-emitting elements of Examples 1 to 9 and Comparative Examples 1 to Comparative Examples 8 are shown. In order to evaluate the properties of the light-emitting elements manufactured in the examples and comparative examples, the driving voltage and current density were measured using a V7000 OLED IVL test system (Polaronix). In order to evaluate the properties of the light-emitting elements manufactured in Examples 1 to 9 and Comparative Examples 1 to Comparative Examples 8, the driving voltage and current density were measured at about 10 mA / cm 2 The driving voltage and efficiency (cd / A) at a current density of about 10 mA / cm 2 When the device was continuously driven at a current density of 1.5 Å, the time taken for the luminance to deteriorate by about 95% from the initial value was set as the relative element life (T95) based on Comparative Example 1 for evaluation.

[0788] [Table 2]

[0789]

[0790] Referring to the results of Table 2, it can be confirmed that, when compared with the comparative example, the example of the light-emitting element using the fused polycyclic compound of the embodiment of the inventive concept as the light-emitting material shows improved emission efficiency and life characteristics. The example compound includes a first substituent connected to the nitrogen atom constituting the fused ring core, and the boron atom can be effectively protected, and high efficiency and long life can be achieved. The example compound introduces a first substituent, suppresses intermolecular interactions, can control the formation of excimers or excimer complexes, and can increase the emission efficiency. The red shift of the emission wavelength can be suppressed. In the example compound, due to the structure with large steric hindrance, the distance between adjacent molecules is increased, and Dexter energy transfer is suppressed, and the degradation of life due to the increase in triplet concentration can be suppressed.

[0791] When compared with the examples, Comparative Examples 1, 2, 6 and 7 show results of reduced element life and efficiency. Comparative Compounds C1, C2, C6 and C7 used in Comparative Examples 1, 2, 6 and 7 have a structure in which a dibenzofuran moiety is linked to a condensed ring core, but do not include an aromatic substituent linked to the dibenzofuran moiety as in the examples, and the steric protection effect of the boron atom in the plate-type structure of the condensed ring core is deteriorated, and it is difficult to suppress the intermolecular interaction effect. In the case of Comparative Compound C6, it can be confirmed that, when compared with the example compounds, the dibenzofuran moiety is not linked to the nitrogen atom through the carbon at the 4-position but through the carbon at the 2-position or the 3-position to induce a red shift.

[0792] Considering Comparative Example 3, Comparative Compound C3 has a fused ring structure having a boron atom and two nitrogen atoms at the center, but does not include the first substituent and the second substituent proposed in the inventive concept in the fused ring skeleton, and when applied to a light-emitting element, it can be confirmed that the emission efficiency and lifetime are reduced compared with the example.

[0793] Considering comparative example 4, comparative compound C4 includes a fused ring structure fused via a boron atom and two nitrogen atoms, but does not include the first substituent and the second substituent proposed in the inventive concept in the fused ring skeleton, and it can be confirmed that the emission efficiency and lifespan are reduced compared to the example. The comparative compound C4 used in comparative example 4 has a structure in which an alkyl group is partially substituted in dibenzofuran, but the steric hindrance effect of the alkyl group is insufficient, and when applied to a light-emitting element, it is believed that the emission efficiency and lifespan are reduced compared to the example. Since comparative compound C4 does not include the second substituent proposed in the inventive concept, the multiple resonance effect and the boron atom protection effect may be reduced compared to the example compound.

[0794] When compared with the examples, Comparative Example 5 shows the results of reduced element life and efficiency. Comparative compound C5 used in Comparative Example 5 has a structure in which a dibenzofuran moiety substituted with a phenyl group is connected to a condensed ring core, but it can be confirmed that the emission efficiency and life are reduced compared with the examples. Comparative compound C5 has a structure in which a phenyl group is connected to a benzene ring that is not connected to a nitrogen atom among the benzene rings constituting the dibenzofuran moiety, and it is difficult to show a sufficient steric hindrance effect when compared with the example compounds, and when applied to a light-emitting element, it is believed that the emission efficiency and life characteristics are reduced.

[0795] When compared with the examples, Comparative Example 8 shows reduced efficiency (specifically, significantly reduced lifespan). Comparative compound C8 included in Comparative Example 8 has a fused structure of a five-membered heterocyclic ring including a sulfur (S) atom in the fused ring core. If the five-membered heterocyclic ring is fused with the fused ring core as in Comparative Compound C8, the chemical stability may be reduced, and therefore, if applied to a light-emitting element, the emission efficiency and element lifespan may be reduced.

[0796] The light emitting element according to the embodiment may show improved element properties of high efficiency and long life.

[0797] The condensed polycyclic compound according to the embodiment may be included in an emission layer of a light emitting element, and may contribute to an increase in efficiency and lifetime of the light emitting element.

[0798] The display device of the embodiment can show excellent display quality.

[0799] Embodiments have been disclosed herein, and although terms are employed, they are used and interpreted in a general and descriptive sense only and not for purposes of limitation. In some cases, as will be apparent to one of ordinary skill in the art, features, characteristics, and / or elements described in connection with an embodiment may be used alone or in combination with features, characteristics, and / or elements described in connection with other embodiments, unless otherwise specifically stated. Accordingly, one of ordinary skill in the art will appreciate that various changes in form and details may be made without departing from the spirit and scope of the disclosure as set forth in the claims.

Claims

1. A fused polycyclic compound, wherein the fused polycyclic compound is represented by Formula 1: [Formula 1] in, In formula 1, R1 to R 10 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, In addition to R a1 To R a3 At least one of them is independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R a1 To R a3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R b , R 11 and R 12 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and are optionally combined with adjacent groups to form a ring, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and m1, n1 and n2 are each independently an integer from 0 to 4.

2. The fused polycyclic compound according to claim 1, wherein The fused polycyclic compound is represented by one of Formula 2-1 to Formula 2-3: [Formula 2-1] [Formula 2-2] [Formula 2-3] Among them, in Formula 2-1 to Formula 2-3, Y1 to Y3 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and Ar1, R1 to R 12 , R a1 To R a3 , R b , m1, n1 and n2 are the same as defined in Formula 1.

3. The fused polycyclic compound according to claim 1, wherein The fused polycyclic compound is represented by Formula 3: [Formula 3] Among them, in formula 3, In addition to R b1 To R b4 At least one of them is independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R b1 To R b4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and are optionally combined with adjacent groups to form a ring, and Ar1, R1 to R 12 , R a1 To R a3 , n1 and n2 are the same as defined in Formula 1.

4. The fused polycyclic compound according to claim 1, wherein The fused polycyclic compound is represented by Formula 4-1 or Formula 4-2: [Formula 4-1] [Formula 4-2] Among them, in formula 4-1 and formula 4-2, R c1 To R c3 , R d , R e , R f and R g1 To R g3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and are optionally combined with adjacent groups to form a ring, m2 is an integer from 0 to 4, and m3 and m4 are each independently an integer from 0 to 5, Among them, in formula 4-1, R c1 To R c3 At least one of them is independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and Among them, in formula 4-1 and formula 4-2, R1 to R 12 , R a1 To R a3 , R b , m1, n1 and n2 are the same as defined in Formula 1.

5. The fused polycyclic compound according to claim 1, wherein The fused polycyclic compound is represented by Formula 5: [Formula 5] Among them, in formula 5, Except that at least one of Z1 to Z5 is independently a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms or a group represented by one of Formula A-1 to Formula A-5, Z1 to Z5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, [Formula A-1] [Formula A-2] [Formula A-3] [Formula A-4] [Formula A-5] Among them, in Formula A-1 to Formula A-5, X1 is O, S, Se, N (Q 11 ) or C(Q 12 )(Q 13 ), Q1 to Q 13 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, m11 to m13 and m18 to m20 are each independently an integer from 0 to 5, m14, m15 and m17 are each independently an integer from 0 to 4, and m16 is an integer from 0 to 3, and Among them, in formula 5, Ar1, R1 to R3, R8, R 10 To R 12 , R a1 To R a3 , R b , m1, n1 and n2 are the same as defined in Formula 1.

6. The fused polycyclic compound according to claim 5, wherein At least one of Z1 to Z5 is independently a group selected from Substituent Group 1: [Substituent Group 1] 7. The fused polycyclic compound according to claim 1, wherein The fused polycyclic compound is represented by Formula 6-1 or Formula 6-2: [Formula 6-1] [Formula 6-2] Among them, in formula 6-1 and formula 6-2, A 1a and A 1b are independently cyano, substituted or unsubstituted amine, substituted or unsubstituted silyl, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, A2 is a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms, B1 to B8 and C1 to C8 are each independently a hydrogen atom or a deuterium atom, and Ar 1a is a group represented by formula B-1 or formula B-2: [Formula B-1] [Formula B-2] Among them, in formula B-1 and formula B-2, R c1 To R c3 , R d , R e , R f and R g1 To R g3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and are optionally combined with adjacent groups to form a ring, m2 is an integer from 0 to 4, and m3 and m4 are each independently an integer from 0 to 5, Wherein, in formula B-1, R c1 To R c3 At least one of them is independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and Among them, in formula 6-1 and formula 6-2, R 11 , R 12 , R a1 To R a3 , R b , m1, n1 and n2 are the same as defined in Formula 1.

8. The fused polycyclic compound according to claim 1, wherein The fused polycyclic compound is represented by Formula 7-1 or Formula 7-2: [Formula 7-1] [Formula 7-2] Among them, in formula 7-1 and formula 7-2, R 13 , R 14 , R c1 To R c3 and R d are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and are optionally combined with adjacent groups to form a ring, n13, n14 and m2 are each independently an integer from 0 to 4, and Ar1, R1 to R5, R7 to R 12 , R a1 To R a3 , R b , m1, n1 and n2 are the same as defined in Formula 1.

9. The fused polycyclic compound according to claim 1, wherein The fused polycyclic compound is selected from compound group 1: [Compound Group 1] 10. A light emitting element, comprising: a first electrode; A second electrode, disposed on the first electrode; as well as An emission layer is provided between the first electrode and the second electrode and includes the condensed polycyclic compound according to any one of claims 1 to 9 as a first compound.

11. The light emitting element according to claim 10, wherein The emission layer further includes at least one of a second compound represented by Formula HT-1, a third compound represented by Formula ET-1, and a fourth compound represented by Formula D-1: [Formula HT-1] Among them, in formula HT-1, M1 to M8 are independently N or C (R 51 ), L1 is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, Y a It is a direct key, C(R 52 )(R 53 ) or Si(R 54 )(R 55 ), Ar a is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and R 51 To R 55 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms, and optionally combines with adjacent groups to form a ring; [Formula ET-1] Among them, in formula ET-1, Z a To Z c At least one of them is N, Z a To Z c The rest of the parts are independently C(R 56 ), R 56 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring carbon atoms, b1 to b3 are each independently an integer from 0 to 10, Ar b To Ar d are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms, and L2 to L4 are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms; and [Formula D-1] Wherein, in formula D-1, Q1 to Q4 are independently C or N, C1 to C4 are each independently a substituted or unsubstituted hydrocarbon ring of 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring of 2 to 30 ring carbon atoms, L 11 To L 13 are independently direct bonds, *—O—*, *—S-*, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, b11 to b13 are independently 0 or 1, R 61 To R 66 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring carbon atoms, and d1 to d4 are each independently an integer from 0 to 4.

12. A display device, comprising: A circuit layer is disposed on the substrate layer; as well as The display device layer is disposed on the circuit layer and includes a light emitting element, wherein: The light emitting element includes: a first electrode; a second electrode provided on the first electrode; and an emission layer provided between the first electrode and the second electrode and including the condensed polycyclic compound according to any one of claims 1 to 9.

13. The display device according to claim 12, wherein: The light emitting element further includes a capping layer disposed on the second electrode, and The cover layer has a refractive index greater than or equal to 1.6 with respect to light in a wavelength range of 550 nm to 660 nm.

14. The display device according to claim 12, wherein: The display device further includes a light control layer, which is disposed on the display device layer and includes quantum dots. The light emitting element emits light of a first color, and The light control layer comprises: a first light control unit including a first quantum dot that converts the first color light into a second color light in a wavelength region greater than the first color light; a second light control unit including a second quantum dot that converts the first color light into a third color light in a wavelength region larger than the first color light and the second color light; and The third light control unit transmits the first color light.

15. The display device according to claim 14, wherein: The display device further includes a color filter layer, the color filter layer being disposed on the light control layer, and The color filter layer comprises: a first filter, transmitting the second color light; a second filter that transmits the third color light; and The third filter transmits the first color light.

Images