Light-emitting element, fused polycyclic compound, and display device

Abstract

Embodiments provide a fused polycyclic compound, a light-emitting element, and a display device. 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 and including the fused polycyclic compound. Said fused polycyclic compound is represented by Formula 1 described in the specification: [Formula 1] # imgabs0 #

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0129446 filed in the Korean Intellectual Property Office on September 26, 2023, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present disclosure relates to a light-emitting element, a condensed polycyclic compound used in the light-emitting element, and a display device including the light-emitting element. Background Art

[0004] Active development of organic electroluminescent display devices as image display devices continues. Compared with liquid crystal display devices, organic electroluminescent display devices are so-called self-luminescent display devices 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.

[0005] When organic electroluminescent devices are applied to display devices, organic electroluminescent devices having lower driving voltage, improved emission efficiency and longer lifespan are required, and materials for organic electroluminescent devices capable of stably achieving such characteristics need to be continuously developed.

[0006] In order to realize an organic electroluminescent device with high efficiency, technologies are being developed regarding phosphorescence emission using triplet energy or regarding fluorescence emission using a phenomenon in which singlet excitons are generated by collision of triplet excitons (triplet-triplet annihilation, TTA). Development currently involves thermally activated delayed fluorescence (TADF) materials using a delayed fluorescence phenomenon.

[0007] It should be understood that this background section is intended, in part, to provide a useful background for understanding the present technology. However, this background section may also include ideas, concepts, or perceptions that were not part of what was known or understood by a person skilled in the relevant art before the corresponding effective filing date of the subject matter disclosed herein. Summary of the invention

[0008] The present disclosure provides a light emitting element having improved emission efficiency and element life.

[0009] The present disclosure provides a fused polycyclic compound capable of improving the emission efficiency and device life of a light-emitting device.

[0010] The present disclosure provides a display device having excellent display quality by including a light emitting element having improved emission efficiency and lifetime.

[0011] The light emitting element according to the embodiment 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:

[0012] [Formula 1]

[0013]

[0014] In formula 1, A 1 To A 5 , R a and R 1 To R 7 Each of the above groups 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 cycloalkyl group having 3 to 20 ring 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, or may be combined with an adjacent group to form a ring; n1 may be an integer from 0 to 3; A 1 To A 5 At least one of them may be independently a group represented by Formula 2; Ar 1 and Ar 2 One of them may be a group represented by Formula 3-1; and Ar 1 and Ar 2 The remaining one of may be a group represented by Formula 3-2.

[0015] [Formula 2]

[0016]

[0017] In formula 2, Ar a To Ar c Each may independently be 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; and -* is a position for connection to Formula 1.

[0018] [Formula 3-1]

[0019]

[0020] [Formula 3-2]

[0021]

[0022] In Formula 3-1 and Formula 3-2, R8 To R 14 and Z 1 To Z 3 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 of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring 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, or may be combined with adjacent groups to form a ring; a1 to a3 may independently be an integer of 0 to 5; and -* is the position connected to Formula 1.

[0023] In an embodiment, the first compound may be represented by Formula 4-1 or Formula 4-2:

[0024] [Formula 4-1]

[0025]

[0026] [Formula 4-2]

[0027]

[0028] In Formula 4-1 and Formula 4-2, Ar 1 ,Ar 2 , R 1 To R 7 , R a , A 1 To A 5 and n1 are the same as those defined in Formula 1.

[0029] In an embodiment, the first compound may be represented by Formula 5:

[0030] [Formula 5]

[0031]

[0032] In formula 5, Ar 1 ,Ar 2 , R 1 To R 7 , R a 、n1、A 1 , A 2 , A 4 , A 5 ,Ar a ,Ar b and Ar c Same as defined in Equation 1 and Equation 2.

[0033] In an embodiment, the first compound may be represented by one of Formula 6-1 to Formula 6-3:

[0034] [Formula 6-1]

[0035]

[0036] [Formula 6-2]

[0037]

[0038] [Formula 6-3]

[0039]

[0040] In equations 6-1 to 6-3, Z 4 It can 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 of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring 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, or it can be combined with adjacent groups to form a ring; and a4 can be an integer from 0 to 5.

[0041] In equations 6-1 to 6-3, R 1 To R 14 , R a , A 1 To A 5 , Z 1 To Z 3 , n1 and a1 to a3 are the same as those defined in Formula 1, Formula 3-1 and Formula 3-2.

[0042] In an embodiment, the first compound may be represented by Formula 7-1 or Formula 7-2: [Formula 7-1]

[0043]

[0044] [Formula 7-2]

[0045]

[0046] In equations 7-1 and 7-2, R b1 To R b3Each of m1 to m3 may independently represent a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring 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, or may be combined with adjacent groups to form a ring; m1 to m3 may independently represent an integer of 0 to 5; Z 4 It can 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 of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring 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, or it can be combined with adjacent groups to form a ring; and a4 can be an integer from 0 to 5.

[0047] In equations 7-1 and 7-2, R 1 To R 13 , R a , A 1 , A 2 , A 4 , A 5 , Z 1 To Z 3 , n1 and a1 to a3 are the same as those defined in Formula 1, Formula 3-1 and Formula 3-2.

[0048] In an embodiment, R 6 may be 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 R 5 and R 7 They may each independently be a hydrogen atom or a deuterium atom.

[0049] In an embodiment, the first compound may be represented by Formula 8-1 or Formula 8-2:

[0050] [Formula 8-1]

[0051]

[0052] [Formula 8-2]

[0053]

[0054] In equations 8-1 and 8-2, R b4 It can 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 of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring 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; m4 can be an integer from 0 to 5; Z 4 It can 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 of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring 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, or it can be combined with adjacent groups to form a ring; and a4 can be an integer from 0 to 5.

[0055] In equations 8-1 and 8-2, R 1 To R 5 , R 7 To R 13 , R a , A 1 To A 5 , Z 1 To Z 3 , n1 and a1 to a3 are the same as those defined in Formula 1, Formula 3-1 and Formula 3-2.

[0056] In an embodiment, the first compound may be represented by Formula 9-1 or Formula 9-2:

[0057] [Formula 9-1]

[0058]

[0059] [Formula 9-2]

[0060]

[0061] In equations 9-1 and 9-2, R 2a and R 3a Each may be independently a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, or a group represented by Formula A-1 or Formula A-2:

[0062] [Formula A-1]

[0063]

[0064] [Formula A-2]

[0065]

[0066] In Formula A-1 and Formula A-2, R c1 To R c3 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 oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amine 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, or may be combined with adjacent groups to form a ring; m11 may be an integer from 0 to 5; and m12 and m13 may each independently be an integer from 0 to 4.

[0067] In formulas 9-1 and 9-2, Ar 1 ,Ar 2 , R 1 To R 7 , A 1 To A 5 , R a and n1 are the same as those defined in Formula 1.

[0068] In the embodiment, in Formula 1, Ar 1 and Ar 2 may be each independently a group selected from Substituent Group 1:

[0069] [Substituent Group 1]

[0070]

[0071] 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:

[0072] [Formula HT-1]

[0073]

[0074] In formula HT-1, M 1 To M 8 can be N or C (R 51 );L 1 Y may be a directly linked, 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 directly connected, 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 R 51 To R 55 Each of the groups 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 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 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms, or may be combined with adjacent groups to form a ring.

[0075] [Formula ET-1]

[0076]

[0077] In formula ET-1, Z a To Z c At least one of them can be N; Z a To Z c The remaining groups may each independently be C(R 56 );R 56 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 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring carbon atoms; b1 to b3 can each independently be an integer of 0 to 10; Ar b To Ar d 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 be independently a directly linked, 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.

[0078] [Formula D-1]

[0079]

[0080] In formula D-1, Q1 To Q 4 may be each independently C or N; C1 to C4 may be each independently a substituted or unsubstituted hydrocarbon ring of 5 to 30 ring carbon atoms, or a substituted or unsubstituted heterocycle 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 each independently be 0 or 1; R 61 To R 66 Each of d1 to d4 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 d1 to d4 may independently be an integer of 0 to 4.

[0081] The display device according to the embodiment may include a circuit layer provided on a base layer and a display element layer provided on the circuit layer and including a light emitting element, wherein:

[0082] The light emitting element 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 described herein.

[0083] In an embodiment, the light emitting element may include a plurality of emission layers; and at least one of the plurality of emission layers may include the first compound.

[0084] In an embodiment, the display device may further include a light control layer arranged on the display element layer and including quantum dots, wherein the light emitting element can emit a first color light; and the light control layer may include a first light control part, a second light control part and a third light control part, the first light control part includes a first quantum dot, the first quantum dot converts the first color light into a second color light in a wavelength region longer than the wavelength region of the first color light, the second light control part includes a second quantum dot, the second quantum dot converts the first color light into a third color light in a wavelength region longer than the wavelength region of the first color light and the second color light, and the third light control part transmits the first color light.

[0085] In an embodiment, the display device may further include a color filter layer disposed on the light control layer, wherein the color filter layer may include a first color filter transmitting the second color light, a second color filter transmitting the third color light, and a third color filter transmitting the first color light.

[0086] The fused polycyclic compound according to an embodiment may be represented by Formula 1 described herein.

[0087] In an embodiment, the fused polycyclic compound represented by Formula 1 may be represented by Formula 4-1 or Formula 4-2 described herein.

[0088] In an embodiment, the fused polycyclic compound represented by Formula 1 may be represented by Formula 7-1 or Formula 7-2 described herein.

[0089] In an embodiment, the fused polycyclic compound represented by Formula 1 may be represented by Formula 8-1 or Formula 8-2 described herein.

[0090] In an embodiment, the fused polycyclic compound represented by Formula 1 may be represented by Formula 9-1 or Formula 9-2 described herein.

[0091] In an embodiment, the condensed polycyclic compound represented by Formula 1 may be selected from Compound Group 1 described below.

[0092] It should be understood that the above embodiments are described in a general and illustrative sense only and not for limiting purposes, and the present disclosure is not limited to the above embodiments. BRIEF DESCRIPTION OF THE DRAWINGS

[0093] 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 embodiments of the present disclosure and principles thereof. The above and other aspects and features of the present disclosure will become more apparent by describing the embodiments of the present disclosure in detail with reference to the accompanying drawings, in which:

[0094] Figure 1 is a schematic plan view of a display device according to an embodiment;

[0095] Figure 2 is a schematic cross-sectional view of a display device according to an embodiment;

[0096] Figure 3 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0097] Figure 4 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0098] Figure 5 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0099] Figure 6 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0100] Figure 7 is a schematic cross-sectional view of a display device according to an embodiment;

[0101] Figure 8 is a schematic cross-sectional view of a display device according to an embodiment;

[0102] Fig. 9 is a schematic cross-sectional view of a display device according to an embodiment;

[0103] Fig.10 is a schematic cross-sectional view of a display device according to an embodiment; and

[0104] Fig.11 is a schematic perspective view of a vehicle including a display device according to an embodiment. DETAILED DESCRIPTION

[0105] The present disclosure will now be described more fully hereinafter with reference to the accompanying drawings, in which embodiments are shown. However, the present disclosure may be implemented in different forms and should not be construed as being limited to the embodiments set forth herein. Instead, these embodiments are provided so that the present disclosure will be thorough and complete, and will fully convey the scope of the present disclosure to those skilled in the art.

[0106] 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 reference letters refer to the same elements throughout.

[0107] In the specification, it will be understood that when an element (or region, layer, component, etc.) is referred to as being "on" another element, "connected to" or "coupled to" another element, the element may be directly on, directly connected to or coupled to the other element, or one or more intervening elements may be present between them. In a similar sense, when an element (or region, layer, component, 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 them.

[0108] In the specification, 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 between them.

[0109] As used herein, expressions such as “a”, “an” and “the” used in the singular are intended to include the plural forms as well, unless the context clearly indicates otherwise.

[0110] 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 a conjunctive or disjunctive sense and may be understood to be equivalent to "and / or".

[0111] 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, AC, BC, or AB. When the term "at least one of" precedes or follows a list of elements, it modifies the entire list of elements, rather than the individual elements in the list.

[0112] It will be understood that, although the terms first, second, etc. can be used in this article 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 teaching of the present disclosure, the first element can be referred to as the second element. Similarly, without departing from the scope of the present disclosure, the second element can be referred to as the first element.

[0113] For ease of description, spatially relative terms such as "below", "below", "lower", "above", or "upper" may be used herein to describe the relationship between one element or component and another element or component as shown in the figure. It will be understood that, in addition to the orientation depicted in the drawings, spatially relative terms are intended to cover different orientations of the device in use or operation. For example, in the case of flipping the device shown in the drawings, a device that is "below" or "below" another device may be "above" another device. Therefore, the exemplary term "below" may include both a lower position and an upper position. The device may also be oriented in other directions, and therefore the spatially relative terms may be interpreted differently depending on the orientation.

[0114] As used herein, the term "about" or "approximately" includes the stated value and means within an acceptable range of deviation of the stated value 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 stated quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations, or within ±20%, ±10%, or ±5% of the stated value.

[0115] It should be understood that the terms “comprises / comprising,” “inclues / including,” “have / having,” and “contains / containing” and the like are intended to specify the presence of stated features, integers, steps, operations, elements, components, or combinations thereof in the present disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.

[0116] 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 be further understood that, unless explicitly defined in the specification, 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 ideal or overly formal sense.

[0117] In the specification, the term "substituted or unsubstituted" can describe a group substituted or unsubstituted by at least one substituent, and the substituent is selected from the group consisting of deuterium atoms, halogen atoms, cyano groups, nitro groups, amino groups, amido groups, silyl groups, oxy groups, sulfenyl groups, sulfinyl groups, sulfonyl groups, carbonyl groups, boron groups, phosphine oxide groups, phosphine sulfide groups, alkyl groups, alkenyl groups, alkynyl groups, hydrocarbon ring groups, aryl groups and heterocyclic groups. Each substituent listed above can itself be substituted or unsubstituted. For example, biphenyl can be interpreted as an aryl group, or it can be interpreted as a phenyl substituted by a phenyl group.

[0118] In the specification, the term "combined with adjacent groups to form a ring" can be interpreted as a group that is bonded with an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. The hydrocarbon ring can be aliphatic or aromatic. The heterocyclic ring can be aliphatic or aromatic. The hydrocarbon ring and the heterocyclic ring can each independently be a monocyclic or polycyclic ring. The ring formed by the adjacent groups combined with each other can itself be connected to another ring to form a spirocyclic structure.

[0119] In the specification, the term "adjacent group" may be interpreted as a substituent that replaces an atom directly connected to the atom substituted by the corresponding substituent, as another substituent that replaces the atom substituted by the corresponding substituent, or as a substituent that is spatially located closest 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.

[0120] In the specification, examples of the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0121] In the specification, the alkyl group may be linear or branched. The number of carbon atoms 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.

[0122] In the specification, the cycloalkyl group may be a cyclic alkyl group. The number of carbon atoms 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, norbornenyl, 1-adamantyl, 2-adamantyl, isobornenyl, bicycloheptyl, etc., but embodiments are not limited thereto.

[0123] In the specification, alkenyl may 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 may be linear or branched. The number of carbon atoms in the alkenyl is not particularly limited, and may be 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl may include vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl, styrylvinyl, etc., but embodiments are not limited thereto.

[0124] In the specification, the alkynyl group may 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. The alkynyl group may be straight chain or branched. The number of carbon atoms in the alkynyl group is not particularly limited, and may be 2 to 30, 2 to 20, or 2 to 10. Examples of the alkynyl group may include ethynyl, propynyl, etc., but embodiments are not limited thereto.

[0125] In the specification, the hydrocarbon ring group may be any functional group or substituent derived from an aliphatic hydrocarbon ring. For example, the hydrocarbon ring group may be a saturated hydrocarbon ring group having 5 to 20 ring-forming carbon atoms.

[0126] In the specification, aryl can be any functional group or substituent derived from an aromatic hydrocarbon ring. Aryl can be monocyclic or polycyclic. The number of ring carbon atoms in the aryl can be 6 to 60, 6 to 50, 6 to 40, 6 to 30, 6 to 20 or 6 to 15. Examples of aryl can include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentaphenyl, hexaphenyl, triphenylenyl, pyrenyl, benzofluoranthenyl, Base, etc., but the embodiment is not limited thereto.

[0127] In the specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro ring structure. Examples of the substituted fluorenyl group may include the groups shown below. However, the embodiment is not limited thereto.

[0128]

[0129] In the specification, the heterocyclic group can be any functional group or substituent derived from a ring including 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.

[0130] In the specification, the heterocyclic group may include at least one of B, O, N, P, Si, S and Se as a heteroatom. If the heterocyclic group includes 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.

[0131] In the specification, the aliphatic heterocyclic group may include at least one of B, O, N, P, Si, S and Se 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 aliphatic heterocyclic groups may include oxirane group, thiirane group, pyrrolidinyl, piperidinyl, tetrahydrofuranyl, tetrahydrothienyl, thianyl, tetrahydropyranyl, 1,4-dioxanyl, etc., but embodiments are not limited thereto.

[0132] In the specification, the heteroaryl group may include at least one of B, O, N, P, Si, S and Se as a heteroatom. If the heteroaryl group includes 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, diphenylthiazolyl, dibenzofuranyl, and the like, but embodiments are not limited thereto.

[0133] In the specification, the above description of the aryl group may be applied to the arylene group, except that the arylene group is a divalent group. In the specification, the above description of the heteroaryl group may be applied to the heteroarylene group, except that the heteroarylene group is a divalent group.

[0134] 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.

[0135] 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.

[0136]

[0137] In the specification, the number of carbon atoms in the sulfinyl group or the sulfonyl group is not particularly limited, and may be 1 to 30. The sulfinyl group may be an alkylsulfinyl group or an arylsulfinyl group. The sulfonyl group may be an alkylsulfonyl group or an arylsulfonyl group.

[0138] In the specification, the thio group may be 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 methylthio, ethylthio, propylthio, pentylthio, hexylthio, octylthio, dodecylthio, cyclopentylthio, cyclohexylthio, phenylthio, naphthylthio, etc., but the embodiment is not limited thereto.

[0139] In the specification, the oxy group can be an oxygen atom bonded to an alkyl or aryl group as defined above. The oxy group can be an alkoxy group or an aryloxy group. The alkoxy group can be linear, branched or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, and can be, for example, 1 to 20 or 1 to 10. Examples of oxy groups can include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, etc., but embodiments are not limited thereto.

[0140] 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, tert-butyl methyl boryl, diphenyl boryl, phenyl boryl, etc., but embodiments are not limited thereto.

[0141] In the specification, the number of carbon atoms in the amine group is not particularly limited, and may be 1 to 30. The amine group may be 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-methylanthrylamine group, etc., but the embodiment is not limited thereto.

[0142] In the specification, the alkyl group in the alkylthio group, the alkylsulfinyloxy group, the alkylaryl group, the alkylamino group, the alkylboryl group, the alkylsilyl group, or the alkylamine group may be the same as exemplified in the above-described alkyl group.

[0143] In the specification, the aryl group in the aryloxy group, the arylthio group, the arylthiooxy group, the arylamino group, the arylboryl group, the arylsilyl group, or the arylamine group may be the same as exemplified in the above-described aryl group.

[0144] In the specification, a direct connection may be a single bond.

[0145] In this manual, the symbol and -* each represent a bond to an adjacent atom in the corresponding formula or moiety.

[0146] Hereinafter, embodiments will be described with reference to the accompanying drawings.

[0147] Figure 1 is a schematic plan view of a display device DD according to the embodiment. Figure 2 is a schematic cross-sectional view of a display device DD according to an embodiment. Figure 2 It is shown along Figure 1 Schematic cross-sectional view of the portion taken along the dotted line II'.

[0148] The display device DD may include a display panel DP and an optical layer PP disposed on the display panel DP. The display panel DP may include light emitting elements ED-1, ED-2, and ED-3. The display device DD may include 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 reflection of 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.

[0149] 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.

[0150] 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.

[0151] The display panel DP may include a base layer BS, a circuit layer DP-CL provided 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.

[0152] 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 include an inorganic layer, an organic layer, or a composite material layer.

[0153] In an embodiment, the circuit layer DP-CL may be disposed on the base layer BS, and the circuit layer DP-CL may include transistors (not shown). The transistors (not shown) may each 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.

[0154] The light emitting elements ED-1, ED-2 and ED-3 may each have Figures 3 to 6 The structure of the light-emitting element ED of the embodiment of any of the figures will be described later. 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.

[0155] 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 each provided as a common layer for the light emitting elements ED-1, ED-2 and ED-3. However, the embodiment is not limited thereto. Although Figure 2 Although not shown in the figure, in an embodiment, the hole transport region HTR and the electron transport region ETR may each be provided by patterning in the opening OH defined in the pixel definition 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 each be provided by patterning via an inkjet printing method.

[0156] The encapsulation layer TFE may cover the light emitting elements ED-1, ED-2 and ED-3. The encapsulation layer TFE may seal the display device layer DP-ED. The encapsulation layer TFE may be a thin film encapsulation layer. The encapsulation layer TFE may be formed of a single layer or multiple 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 referred to as an encapsulation inorganic film). In an embodiment, the encapsulation layer TFE may include at least one organic film (hereinafter referred to as an encapsulation organic film) and at least one encapsulation inorganic film.

[0157] The encapsulated inorganic film protects the display device layer DP-ED from moisture and / or oxygen, and the encapsulated organic film protects the display device layer DP-ED from foreign matter such as dust particles. The encapsulated inorganic film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, or aluminum oxide, etc., but the embodiment is not limited thereto. The encapsulated organic film may include an acrylic compound or an epoxy compound, etc. The encapsulated organic film may include a photopolymerizable organic material, but the embodiment is not limited thereto.

[0158] The encapsulation layer TFE may be disposed on the second electrode EL2 , and may be disposed to fill the opening OH.

[0159] refer to 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, respectively. In a plan view, the light emitting areas PXA-R, PXA-G, and PXA-B may be spaced apart from each other.

[0160] The light-emitting regions PXA-R, PXA-G, and PXA-B may be regions each separated from each other 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, and it may correspond to the pixel defining film PDL. In an embodiment, the light-emitting regions PXA-R, PXA-G, and PXA-B may each correspond to a pixel. 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 the opening OH defined in the pixel defining film PDL and separated from each other.

[0161] The light emitting regions PXA-R, PXA-G, and PXA-B may be arranged into 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 that emit 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 that are different from each other.

[0162] 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.

[0163] However, the embodiment is not limited thereto, and the first light emitting element ED-1, the second light emitting element ED-2, and the third light emitting element 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 the remaining light emitting elements. For example, the first light emitting element ED-1, the second light emitting element ED-2, and the third light emitting element ED-3 may each emit blue light.

[0164] 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, respectively. 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.

[0165] Figure 1 and Figure 2 It is shown that the light emitting regions PXA-R, PXA-G, and PXA-B all have similar areas, but the embodiment is not limited thereto. In an embodiment, 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 area of ​​the light emitting regions PXA-R, PXA-G, and PXA-B may be an area defined by the first direction axis DR1 and the second direction axis DR2 in a plan view. The third direction axis DR3 may be perpendicular to a plane defined by the first direction axis DR1 and the second direction axis DR2.

[0166] The arrangement of the light emitting regions PXA-R, PXA-G, and PXA-B is not limited to Figure 1 , and the order in which the red light emitting regions PXA-R, the green light emitting regions PXA-G, and the blue light emitting regions PXA-B are arranged may be provided in various combinations according to the display quality characteristics required by the display device DD. For example, the light emitting regions PXA-R, PXA-G, and PXA-B may be arranged in a five-tile configuration (such as ) or in a diamond configuration (such as Diamond )arrangement.

[0167] 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.

[0168] In the following, Figures 3 to 6 Each is a schematic cross-sectional view of a light emitting element ED according to an embodiment. The embodiment provides a light emitting element ED that may include a first electrode EL1, a second electrode EL2 disposed on 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 may include a fused polycyclic compound according to an embodiment to be described later in at least one functional layer.

[0169] In an embodiment, the light emitting element ED may include a hole transport region HTR, an emission layer EML, an electron transport region ETR, etc., as at least one functional layer. Figure 3 In the embodiment shown in , the light emitting element ED 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 .

[0170] and Figure 3 compared to, Figure 4 is a schematic cross-sectional view of a light emitting element ED according to an embodiment, 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 is a schematic cross-sectional view of a light emitting element ED according to an embodiment, 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 2 is a schematic cross-sectional view of a light emitting element ED according to an embodiment, the light emitting element ED including a cover layer CPL provided on the second electrode EL2 .

[0171] The light emitting element ED according to the embodiment may include a fused polycyclic compound according to the embodiment to be described later in at least one functional layer. In the light emitting element ED, 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 according to the embodiment. For example, in the light emitting element ED, the emission layer EML may include the fused polycyclic compound.

[0172] The first electrode EL1 has 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. In an embodiment, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a semi-transmissive reflective electrode, or a reflective electrode. The first electrode EL1 may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, Zn, oxides thereof, compounds thereof, and mixtures thereof.

[0173] 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 semi-transmissive reflective 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, or 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) or LiF / Al (a stacking structure of LiF and Al). In another embodiment, the first electrode EL1 may have a multilayer structure including a reflective film or a semi-transmissive reflective 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, or an oxide of the above metal materials. 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.

[0174] A hole transport region HTR may be provided 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.

[0175] 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.

[0176] In an embodiment, 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 an embodiment, 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 are stacked from the first electrode EL1 in their respective stated order, but the embodiment is not limited thereto.

[0177] 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.

[0178] In the light emitting element ED according to the embodiment, the hole transport region HTR may include a compound represented by Formula H-1:

[0179] [Formula H-1]

[0180]

[0181] In formula H-1, L 1 and L 2 Each of L is independently a directly connected, 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 H-1, a and b are independently an integer of 0 to 10. When a or b is 2 or more, multiple L 1 Group or multiple L 2 The groups may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0182] In formula H-1, Ar 1 and Ar 2 and Ar 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. 3It 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.

[0183] 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 Ar 1 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 may be a carbazole compound in which Ar 1 and Ar 2 At least one of the fluorene compounds includes a substituted or unsubstituted fluorenyl group.

[0184] 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 Compound Group H:

[0185] [Compound Group H]

[0186]

[0187]

[0188] 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 (P ANI / 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], dipyrazine[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HATCN), etc.

[0189] The hole transport region HTR may include carbazole derivatives such as 1,3-bis(N-carbazolyl)benzene (mCP), N-phenylcarbazole or polyvinylcarbazole, fluorene derivatives, triphenylamine derivatives 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'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), etc.

[0190] 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.

[0191] The hole transport region HTR may include the above-mentioned compound of the hole transport region in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.

[0192] The thickness of the hole transport region HTR may 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 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 about 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.

[0193] 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-containing compound, but the embodiment is not limited thereto. For example, the p-dopant may include: a metal halide compound such as CuI or RbI; a quinone derivative such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ); a metal oxide such as tungsten oxide or molybdenum oxide; a cyano-containing compound such as dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexanitrile (HATCN) or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropylene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile (NDP9), etc., but the embodiments are not limited thereto.

[0194] 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 thus the light emission efficiency may be improved. The material that may be included in the hole transport region HTR may be used as a material in the buffer layer (not shown). The electron blocking layer EBL may prevent electrons from being injected from the electron transport region ETR into the hole transport region HTR.

[0195] The emission layer EML may be disposed on the hole transport region HTR. The emission layer EML may have a thickness of about 100 nm. To about For example, the emission layer EML may have a thickness in the range 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.

[0196] 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, the emission layer EML may include the fused polycyclic compound according to the embodiment. In the embodiment, the emission layer EML may include the fused polycyclic compound as a dopant. The fused polycyclic compound may be a dopant material of the emission layer EML. In the description, the fused polycyclic compound according to the embodiment may be referred to as a first compound.

[0197] The fused polycyclic compound may include a fused ring core in which five rings are fused together, wherein the fused ring core includes a boron atom, two nitrogen atoms and an aryl group. In an embodiment, the fused ring core of the fused polycyclic compound may have five rings, wherein three substituted or unsubstituted benzene rings are connected to each other via a boron atom and two nitrogen atoms. In the fused ring core, three benzene rings are connected to each other with a boron atom as the central atom, and in the three benzene rings, the first benzene ring and the second benzene ring may be connected to each other via a nitrogen atom, and the third benzene ring may be connected to the second benzene ring via another nitrogen atom. The boron atom and the two nitrogen atoms may all be connected to the second benzene ring.

[0198] The aryl group included in the fused polycyclic compound can be connected to the first benzene ring. The aryl group can be directly connected to the first benzene ring without a separate connecting portion. The aryl group can be a monocyclic or polycyclic aromatic hydrocarbon ring. For example, the aryl group can be a six-membered monocyclic aromatic hydrocarbon ring. In the specification, the first benzene ring of the fused ring core and the aryl group connected to the first benzene ring can be referred to as a "diaryl moiety".

[0199] The fused polycyclic compound according to the embodiment may include a silyl group as a substituent. The silyl group may be substituted by a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. The silyl group may be connected to the fused ring core via the aryl group.

[0200] The fused polycyclic compound according to the embodiment may include a first substituent and a second substituent as sterically hindered substituents in the molecular structure. The first substituent and the second substituent may each be connected to the nitrogen atom of the fused ring core. The first substituent may be connected to one of the nitrogen atoms of the fused ring core, and the second substituent may be connected to the remaining nitrogen atoms. The first substituent may include a benzene moiety, a first sub-substituent and a second sub-substituent, and the first sub-substituent and the second sub-substituent are substituted at the carbon atom at the specific position of the benzene moiety. The first substituent may be connected to the nitrogen atom of the fused ring core, and may include the first sub-substituent and the second sub-substituent, each of which is connected to the ortho position relative to the nitrogen atom. The first sub-substituent and the second sub-substituent may each independently be substituted or unsubstituted aryl groups of 6 to 30 ring-forming carbon atoms. The second substituent may include a benzene moiety and a third sub-substituent substituted at the carbon atom at the specific position of the benzene moiety. The second substituent may be connected to the remaining nitrogen atoms of the fused ring core, and may have a structure in which the third sub-substituent is connected to the ortho position relative to the remaining nitrogen atoms. The third substituent may be a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms.

[0201] The fused polycyclic compound according to an embodiment may be represented by Formula 1:

[0202] [Formula 1]

[0203]

[0204] The fused polycyclic compound according to the embodiment represented by Formula 1 may include a fused ring core formed by fusing five rings with a boron atom, a first nitrogen atom, and a second nitrogen atom, and an aryl group connected to the fused ring core. The fused polycyclic compound may include a silyl group connected to the fused ring core via an aryl group. In the specification, in Formula 1, the fused polycyclic compound including R a The benzene ring of the substituent represented by may correspond to the first benzene ring, including the benzene ring represented by R 1 To R 4 The benzene ring of the substituent represented by may correspond to the third benzene ring and include R 5 To R 7 The benzene ring of the substituent represented by may correspond to the second benzene ring. 1 To A 5 The benzene ring of the substituent represented by may correspond to an aryl group.

[0205] In formula 1, A 1 To A 5 , R a and R 1 To R 7Each of the above groups may be 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 cycloalkyl group having 3 to 20 ring 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, or may be combined with adjacent groups to form a ring. For example, A 1 To A 5 R may be independently a hydrogen atom, or a substituted or unsubstituted silyl group; a may be a hydrogen atom; and R 1 To R 7 Each independently may be a hydrogen atom, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.

[0206] In an embodiment, R 6 may be 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 R 5 and R 7 can be independently a hydrogen atom or a deuterium atom. 6 may be a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group, and R 5 and R 7 Each may be a hydrogen atom.

[0207] In Formula 1, n1 may be an integer from 0 to 3. If n1 is 0, the fused polycyclic compound may not be a Substitution. n1 is 3 and three R a The case where all the groups are hydrogen atoms can be the same as the case where n1 is 0. If n1 is 2 or more, then multiple R a The groups may all be identical, or at least one of them may be different from the remaining groups.

[0208] In formula 1, A 1 To A 5 At least one of may be independently a group represented by Formula 2. In an embodiment, A 1 To A 5 One of them may be a group represented by Formula 2, and A 1 To A 5 The remaining groups in can be independently hydrogen atoms or deuterium atoms. 3 may be a group represented by Formula 2; and A1 , A 2 , A 4 and A 5 They may each independently be a hydrogen atom or a deuterium atom.

[0209] In formula 1, Ar 1 and Ar 2 One of them may be a group represented by Formula 3-1; and Ar 1 and Ar 2 The remaining one of the groups may be a group represented by Formula 3-2.

[0210] [Formula 2]

[0211]

[0212] In formula 2, Ar a To Ar c Each of them may be independently 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. a To Ar c Each independently may be substituted or unsubstituted phenyl.

[0213] In Formula 2, -* is the position for connection with Formula 1.

[0214] [Formula 3-1]

[0215]

[0216] [Formula 3-2]

[0217]

[0218] In Formula 3-1 and Formula 3-2, R 8 To R 14 and Z 1 To Z 3 Each of R and R 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 cycloalkyl group having 3 to 20 ring 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, or may be combined with adjacent groups to form a ring. For example, R 8 To R 14may each independently be a hydrogen atom, a substituted or unsubstituted methyl group, a deuterated methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group; and Z 1 To Z 3 Can be each independently a hydrogen atom, a substituted or unsubstituted tert-butyl group or a substituted or unsubstituted phenyl. In the specification, the term "deuterated methyl" can be interpreted as making at least one hydrogen atom of the methyl group be substituted by a deuterium atom. In the deuterated methyl group, the methyl group can be monosubstituted, disubstituted or completely substituted by deuterium.

[0219] In Formula 3-1 and Formula 3-2, a1 to a3 may each independently be an integer of 0 to 5. When a1 to a3 are each 0, the fused polycyclic compound may not be respectively 1 To Z 3 a1 to a3 are all 5 and Z 1 To Z 3 The case where each of the five groups is a hydrogen atom may be the same as the case where each of a1 to a3 is 0. If each of a1 to a3 is 2 or more, then Z 1 To Z 3 The respective multiple groups may all be the same, or at least one of them may be different from the remaining groups.

[0220] In Formula 3-1 and Formula 3-2, -* is the position for connection with Formula 1.

[0221] In an embodiment, the group represented by Formula 3-2 may be represented by Formula 3-2-a.

[0222] [Formula 3-2-a]

[0223]

[0224] In formula 3-2-a, Z 4 It 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 of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring 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, or it may be combined with adjacent groups to form a ring. For example, Z 4 It may be a hydrogen atom, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.

[0225] In Formula 3-2-a, a4 may be an integer from 0 to 5. If a4 is 0, the fused polycyclic compound may not be Z 4Replace. a4 is 5 and five Z 4 The case where all the groups are hydrogen atoms may be the same as the case where a4 is 0. If a4 is 2 or more, then multiple Z 4 The groups may all be identical, or at least one of them may be different from the remaining groups.

[0226] In formula 3-2-a, Z 3 , a3 and R 11 To R 13 Same as defined in formula 3-2.

[0227] The fused polycyclic compound according to the embodiment includes a structure in which an aromatic group is linked to a fused ring core, and may exhibit improved thermally activated delayed fluorescence properties.

[0228] The compound showing the thermally activated delayed fluorescence property undergoes intersystem crossing (ICS) of the energy transition from the lowest singlet energy level to the lowest excited triplet energy level, and then undergoes reverse intersystem crossing (RISC) of the transition from the lowest excited triplet energy level to the lowest excited singlet energy level, and then undergoes delayed fluorescence by transitioning from the lowest excited singlet energy level to the ground state. The mechanism of thermally activated delayed fluorescence can also include energy transitions of higher triplet energy levels (Tn levels) during intersystem crossing (ICS) and reverse intersystem crossing (RISC).

[0229] In a light-emitting element using thermally activated delayed fluorescence emission, an important factor indicating low efficiency and short life is a low reverse intersystem crossing rate in an emitter based on thermally activated delayed fluorescence (TADF). According to the El-sayed rule, the spin-orbit coupling constant between the lowest excited singlet energy level (S1) and the lowest excited triplet energy level (T1) is close to 0, and a direct transition between the lowest excited singlet energy level (S1) and the lowest excited triplet energy level (T1) may not occur easily, and therefore, a complex intersystem crossing mechanism involving transitions of higher excited triplet energy levels (Tn, where n is 2 or greater) is used. Under such conditions, exciton quenching may occur, such as collisions of accumulated triplet excitons, and thus may lead to degradation of the efficiency and life of the organic light-emitting device. Therefore, if the high-energy triplet excitons accumulated in the emitter transition at a fast rate, the emission efficiency and life can be improved.

[0230] According to an embodiment, the reverse intersystem crossing rate of the fused polycyclic compound can be increased by the local excited triplet energy level ( 3 In the fused polycyclic compound according to the embodiment, the local excited triplet energy level ( 3LE) can be formed between the lowest excited triplet energy level (T1) and the second excited triplet energy level (T2). Therefore, the reverse intersystem crossing (RISC) between the lowest excited triplet energy level (T1) and the lowest excited singlet energy level (S1) can be generated by the local excited triplet energy level ( 3 LE) mediated to increase the rate of reverse intersystem crossing. For example, if the locally excited triplet level ( 3 LE) is between the lowest excited triplet energy level (T1) and the second excited triplet energy level (T2), then the exciton energy can be increased through T1→ 3 The path of LE→S1 transitions quickly, and therefore, the rate of reverse intersystem crossing can be increased to improve the emission efficiency.

[0231] In the fused polycyclic compound according to the embodiment, the local excited triplet energy level ( 3 The spin-orbit coupling constant between the lowest excited triplet energy level (T1) and the lowest singlet energy level (S1) can be greater than the spin-orbit coupling constant between the lowest excited triplet energy level (T1) and the lowest singlet energy level (S1). Because the transition probability between the triplet state and the singlet state depends on the strength of the spin-orbit interaction, the fused polycyclic compound with an increased spin-orbit coupling constant can have an increased reverse intersystem crossing rate.

[0232] The fused polycyclic compound according to the embodiment includes a silyl group as a substituent. The silyl group can be connected to the fused ring core via an aryl group. The fused polycyclic compound includes a silyl group with a large volume to increase the intermolecular distance, prevent Dexter energy transfer, and improve the performance of the element. In the molecule, the orbital will not expand in the silyl group, and the optical properties such as the absorption wavelength and the emission wavelength will not be affected. Therefore, the emission efficiency and life characteristics can be improved while maintaining the excellent optical properties of the molecule itself. Compared with other substituents, the silyl group has good thermal stability and can help improve the stability of the material.

[0233] The fused polycyclic compound according to the embodiment can effectively maintain the triangular planar structure of the boron atom by the steric hindrance effect caused by the first substituent and the second substituent. Because the boron atom has an electron-deficient property due to the empty p orbital, it can form a bond with other nucleophiles to change the triangular face structure into a tetrahedral structure, which can cause degradation of the light-emitting element. According to the embodiment, the fused polycyclic compound represented by Formula 1 includes a first substituent and a second substituent in the fused ring core, and can effectively protect the empty p orbital of the boron atom, and therefore, can prevent degradation due to molecular structure deformation.

[0234] In the fused polycyclic compound according to the embodiment, the intermolecular interaction is suppressed by the steric hindrance effect caused by the first substituent and the second substituent, and the formation of aggregates, excimers and excimers can be controlled, and therefore, the emission efficiency can be improved. Because the fused polycyclic compound has a bulky structure, the intermolecular distance can be increased to reduce Dexter energy transfer, and therefore, the concentration increase of triplet excitons in the fused polycyclic compound can be suppressed. Because the high concentration of triplet excitons can remain in an excited state for a long time, it may cause the decomposition of the compound, may cause the generation of hot excitons with high energy caused by triplet-triplet annihilation (TTA), and may cause the breakage of the adjacent compound structure. Triplet-triplet annihilation is a bimolecular reaction, and rapidly depletes triplet excitons for luminescence, and therefore, non-radiative transitions may cause a reduction in emission efficiency. Since the intermolecular distance can be increased due to the first substituent and the second substituent in the fused polycyclic compound, Dexter energy transfer can be suppressed, and the degradation of the device life caused by the increase in the concentration of triplet excitons can be suppressed. Therefore, if the fused polycyclic compound is applied to the emission layer EML of the light-emitting element ED, the emission efficiency can be improved, and the element life can also be extended.

[0235] In an embodiment, the fused polycyclic compound represented by Formula 1 may be represented by Formula 4-1 or Formula 4-2.

[0236] [Formula 4-1]

[0237]

[0238] [Formula 4-2]

[0239]

[0240] In Formula 4-1 and Formula 4-2, Ar 1 ,Ar 2 , R 1 To R 7 , R a , A 1 To A 5 and n1 are the same as those defined in Formula 1.

[0241] In an embodiment, the fused polycyclic compound represented by Formula 1 may be represented by Formula 5.

[0242] [Formula 5]

[0243]

[0244] Formula 5 represents a case where the bonding position of the group represented by Formula 2 and Formula 1 is further limited.

[0245] In formula 5, Ar 1 ,Ar 2 , R 1 To R 7 , R a 、n1、A 1 , A 2 , A 4 , A 5 ,Ar a ,Ar b and Ar c Same as defined in Equation 1 and Equation 2.

[0246] In an embodiment, the fused polycyclic compound represented by Formula 1 may be represented by one of Formula 6-1 to Formula 6-3.

[0247] [Formula 6-1]

[0248]

[0249] [Formula 6-2]

[0250]

[0251] [Formula 6-3]

[0252]

[0253] In formula 6-3, Z 4 It 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 of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring 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, or it may be combined with adjacent groups to form a ring. For example, Z 4 It may be a hydrogen atom, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.

[0254] In Formula 6-3, a4 may be an integer from 0 to 5. If a4 is 0, the fused polycyclic compound may not be Z 4 Replace. a4 is 5 and five Z 4 The case where all the groups are hydrogen atoms may be the same as the case where a4 is 0. If a4 is 2 or more, then multiple Z 4 The groups may all be identical, or at least one of them may be different from the remaining groups.

[0255] In equations 6-1 to 6-3, R1 To R 14 , R a , A 1 To A 5 , Z 1 To Z 3 , n1 and a1 to a3 are the same as those defined in Formula 1, Formula 3-1 and Formula 3-2.

[0256] In an embodiment, the fused polycyclic compound represented by Formula 1 may be represented by Formula 7-1 or Formula 7-2.

[0257] [Formula 7-1]

[0258]

[0259] [Formula 7-2]

[0260]

[0261] In equations 7-1 and 7-2, R b1 To R b3 Each of the R and R groups may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro 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 cycloalkyl group having 3 to 20 ring 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, or may be combined with adjacent groups to form a ring. For example, R b1 To R b3 Each may be a hydrogen atom.

[0262] In Formula 7-1 and Formula 7-2, m1 to m3 may each independently be an integer of 0 to 5. If m1 to m3 are each 0, the fused polycyclic compound may not be respectively R b1 To R b3 m1 to m3 are each 5 and R b1 To R b3 The case where each of the five groups in is a hydrogen atom may be the same as the case where each of m1 to m3 is 0. If each of m1 to m3 is 2 or more, then R b1 To R b3 The multiple groups of each of may all be the same, or at least one of them may be different from the remaining groups.

[0263] In equations 7-1 and 7-2, Z 4It 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 of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring 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, or it may be combined with adjacent groups to form a ring. For example, Z 4 It may be a hydrogen atom, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.

[0264] In Formula 7-1 and Formula 7-2, a4 may be an integer from 0 to 5. If a4 is 0, the fused polycyclic compound may not be Z 4 Replace. a4 is 5 and five Z 4 The case where all the groups are hydrogen atoms may be the same as the case where a4 is 0. If a4 is 2 or more, then multiple Z 4 The groups may all be identical, or at least one of them may be different from the remaining groups.

[0265] In equations 7-1 and 7-2, R 1 To R 13 , R a , A 1 , A 2 , A 4 , A 5 , Z 1 To Z 3 , n1 and a1 to a3 are the same as those defined in Formula 1, Formula 3-1 and Formula 3-2.

[0266] In an embodiment, the fused polycyclic compound represented by Formula 1 may be represented by Formula 8-1 or Formula 8-2.

[0267] [Formula 8-1]

[0268]

[0269] [Formula 8-2]

[0270]

[0271] In formula 8-2, R b4It 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 cycloalkyl group having 3 to 20 ring 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 b4 It may be a hydrogen atom or a substituted or unsubstituted tert-butyl group.

[0272] In Formula 8-2, m4 may be an integer from 0 to 5. If m4 is 0, the fused polycyclic compound may not be b4 Replace. m4 is 5 and five R b4 The case where all the groups are hydrogen atoms can be the same as the case where m4 is 0. If m4 is 2 or greater, then multiple R b4 The groups may all be identical, or at least one of them may be different from the remaining groups.

[0273] In equations 8-1 and 8-2, Z 4 It 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 of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring 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, or it may be combined with adjacent groups to form a ring. For example, Z 4 It may be a hydrogen atom, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.

[0274] In Formula 8-1 and Formula 8-2, a4 may be an integer from 0 to 5. If a4 is 0, the fused polycyclic compound may not be Z 4 Replace. a4 is 5 and five Z 4 The case where all the groups are hydrogen atoms may be the same as the case where a4 is 0. If a4 is 2 or more, then multiple Z 4 The groups may all be identical, or at least one of them may be different from the remaining groups.

[0275] In equations 8-1 and 8-2, R 1 To R 5 , R 7 To R 13 , R a , A 1 To A 5 , Z1 To Z 3 , n1 and a1 to a3 are the same as those defined in Formula 1, Formula 3-1 and Formula 3-2.

[0276] In an embodiment, the fused polycyclic compound represented by Formula 1 may be represented by Formula 9-1 or Formula 9-2.

[0277] [Formula 9-1]

[0278]

[0279] [Formula 9-2]

[0280]

[0281] In equations 9-1 and 9-2, R 2a and R 3a Each of them may be independently a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, or a group represented by Formula A-1 or Formula A-2. 2a and R 3a Each independently may be a substituted or unsubstituted tert-butyl group, or a group represented by Formula A-1 or Formula A-2.

[0282] [Formula A-1]

[0283]

[0284] [Formula A-2]

[0285]

[0286] In Formula A-1 and Formula A-2, R c1 To R c3 Each of R and R 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 oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amine 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, or may be combined with adjacent groups to form a ring. For example, R c1 To R c3 They may each independently be a hydrogen atom, a deuterium atom, a deuterated methyl group, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.

[0287] In Formula A-1, m11 may be an integer from 0 to 5. When m11 is 0, the fused polycyclic compound may not be c1 Replace. m11 is 5 and five Rc1 The case where all the groups are hydrogen atoms can be the same as the case where m11 is 0. If m11 is 2 or greater, then multiple R c1 The groups may all be identical, or at least one of them may be different from the remaining groups.

[0288] In formula A-2, m12 and m13 may each independently be an integer of 0 to 4. If m12 and m13 are each 0, the fused polycyclic compound may not be separated by R c2 and R c3 m12 and m13 are each 4 and R c2 and R c3 The case where each of the multiple groups in is a hydrogen atom may be the same as the case where m12 and m13 are each 0. If m12 and m13 are each 2 or greater, then the multiple R c2 Groups and multiple R c3 The groups may all be identical, or at least one of them may be different from the remaining groups.

[0289] In formulas 9-1 and 9-2, Ar 1 ,Ar 2 , R 1 To R 7 , A 1 To A 5 , R a and n1 are the same as those defined in Formula 1.

[0290] In an embodiment, the fused polycyclic compound represented by Formula 1 may be represented by one of Formulas 10-1 to 10-3.

[0291] [Formula 10-1]

[0292]

[0293] [Formula 10-2]

[0294]

[0295] [Formula 10-3]

[0296]

[0297] In Formula 10-1 to Formula 10-3, R d1 To R d4Each of R and R 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 oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amine 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, or may be combined with adjacent groups to form a ring. For example, R d1 To R d4 They may each independently be a hydrogen atom, a deuterium atom, a deuterated methyl group, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.

[0298] In Formula 10-1, m21 and m22 may each independently be an integer of 0 to 4. If m21 and m22 are each 0, the fused polycyclic compound may not be separated by R d1 and R d2 m21 and m22 are each 4 and the four R d1 Groups and the Four Rs d2 The case where the groups are all hydrogen atoms may be the same as the case where m21 and m22 are each 0. If m21 and m22 are each 2 or greater, then multiple R d1 Groups and multiple R d2 The groups may all be identical, or at least one of them may be different from the remaining groups.

[0299] In Formula 10-2 and Formula 10-3, m23 and m24 may each independently be an integer of 0 to 5. If m23 and m24 are each 0, the fused polycyclic compound may not be respectively R d3 and R d4 m23 and m24 are each 5 and five R d3 Groups and the Five Rs d4 The case where the groups are all hydrogen atoms can be the same as the case where m23 and m24 are each 0. If m23 and m24 are each 2 or more, then multiple R d3 Groups and multiple R d4 The groups may all be identical, or at least one of them may be different from the remaining groups.

[0300] In equations 10-1 to 10-3, Z 4It 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 of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring 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, or it may be combined with adjacent groups to form a ring. For example, Z 4 It may be a hydrogen atom, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.

[0301] In Formula 10-1 to Formula 10-3, a4 may be an integer from 0 to 5. If a4 is 0, the fused polycyclic compound may not be Z 4 Replace. a4 is 5 and five Z 4 The case where all the groups are hydrogen atoms may be the same as the case where a4 is 0. If a4 is 2 or more, then multiple Z 4 The groups may all be identical, or at least one of them may be different from the remaining groups.

[0302] In Formula 10-1 to Formula 10-3, R 1 To R 13 , A 1 To A 5 , R a 、n1、Z 1 To Z 3 and a1 to a3 are the same as those defined in Formula 1, Formula 3-1, and Formula 3-2.

[0303] In the embodiment, in Formula 1, Ar 1 and Ar 2 Each may be independently a group selected from Substituent Group 1.

[0304] [Substituent Group 1]

[0305]

[0306]

[0307] In an embodiment, the condensed polycyclic compound represented by Formula 1 may include at least one deuterium atom as a substituent. The condensed polycyclic compound represented by Formula 1 according to an embodiment may have a structure in which at least one hydrogen atom is substituted with a deuterium atom.

[0308] In the embodiment, the condensed polycyclic compound may be any compound selected from compound group 1. In the embodiment, in the light emitting element ED (see Figure 3), at least one functional layer (eg, an emission layer EML (see Figure 3 )) may include at least one condensed polycyclic compound selected from Compound Group 1.

[0309] [Compound Group 1]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325] In compound group 1, D represents a deuterium atom.

[0326] 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 10nm to 50nm. For example, the emission spectrum of the fused polycyclic compound represented by Formula 1 may have a FWHM in the range of about 20nm to 40nm. Because the emission spectrum of the fused polycyclic compound represented by Formula 1 has the range of the full width at half maximum described above, when the light-emitting element includes the fused polycyclic compound, the emission efficiency of the light-emitting element can be improved. If a fused polycyclic compound is used as a material for a blue light-emitting element, the element life can be improved.

[0327] In an embodiment, the fused polycyclic compound according to the embodiment may be a material for emitting thermally activated delayed fluorescence. In an embodiment, the fused polycyclic compound may be a material for emitting thermally activated delayed fluorescence. ST ) is equal to or less than about 0.6 eV. For example, the fused polycyclic compound may be a thermally activated delayed fluorescent dopant having a difference (ΔE) between the lowest triplet excitation energy level (T1) and the lowest singlet excitation energy level (S1). ST ) is equal to or less than about 0.2 eV of the thermally activated delayed fluorescent dopant. However, the embodiment is not limited thereto.

[0328] In an embodiment, the fused polycyclic compound may include a first substituent and a second substituent as described above. By adjusting the substituents of the first substituent and the second substituent and their respective bonding positions, the singlet energy level and the triplet energy level can be appropriately controlled in the entire fused polycyclic compound. Therefore, the fused polycyclic compound according to the embodiment can exhibit improved thermally activated delayed fluorescence properties.

[0329] The fused polycyclic compound may be a luminescent material having a central wavelength in the range of about 430 nm to about 490 nm. For example, the fused polycyclic compound 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 the luminescent material, the fused polycyclic compound may be used as a dopant material emitting light in various wavelength regions, such as a red emission dopant or a green emission dopant.

[0330] 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).

[0331] 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 center wavelength equal to or less than about 490 nm. However, the embodiment is not limited thereto, and the emission layer EML may emit green light or red light.

[0332] A fused polycyclic compound may be included in the emission layer EML. The fused polycyclic compound may be included in the emission layer EML as a dopant material. The fused polycyclic compound may be a thermally activated delayed fluorescent material. The fused polycyclic compound may be used as a thermally activated delayed fluorescent 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 delayed fluorescent dopant. However, the use of the fused polycyclic compound is not limited thereto.

[0333] In an embodiment, the emission layer EML may include a plurality of compounds. In an embodiment, the emission layer EML 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.

[0334] 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.

[0335] 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.

[0336] [Formula HT-1]

[0337]

[0338] In formula HT-1, M 1 To M 8 can be N or C (R 51 ). For example, M 1 To M 8 can be independently C(R 51 ). In another example, M 1 To M 8 Any one of can be N, and M 1 To M 8 The remaining groups in may be independently C(R 51 ).

[0339] In formula HT-1, L 1 It may be a directly linked, 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 connection, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted divalent carbazole group, etc., but the embodiment is not limited thereto.

[0340] In formula HT-1, Y a Can be directly connected, C(R 52 )(R 53 ) or Si(R 54 )(R 55 ). For example, the two rings connected to the nitrogen atom of formula HT-1 can be connected directly, In formula HT-1, if Ya For direct attachment, the second compound represented by Formula HT-1 may include a carbazole moiety.

[0341] 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, or a substituted or unsubstituted biphenyl group, but the embodiment is not limited thereto.

[0342] In formula HT-1, 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 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 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, or may be 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 independently may be an unsubstituted methyl group or an unsubstituted phenyl group.

[0343] 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.

[0344] [Compound Group 2]

[0345]

[0346]

[0347]

[0348] In compound group 2, D represents a deuterium atom, and Ph represents a substituted or unsubstituted phenyl group. For example, in compound group 2, Ph may represent an unsubstituted phenyl group.

[0349] 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.

[0350] [Formula ET-1]

[0351]

[0352] In formula ET-1, Z a To Z c At least one of them can each be N, and Z a To Z c The remaining groups in may be independently C(R 56 ). For example, Z a To Z c One of them can be N, and Z a To Z c The remaining groups 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 each be N, and Z a To Z c The remaining groups in 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 Each may be N. Therefore, the third compound represented by Formula ET-1 may include a triazine moiety.

[0353] 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.

[0354] In Formula ET-1, b1 to b3 may each independently be an integer of 0 to 10.

[0355] In formula ET-1, Ar b To Ar d and R and R are each independently 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. b To Ar d Each independently may be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.

[0356] In formula ET-1, L 2 To L 4Each of L and L may be independently a directly linked, 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 the plurality of groups may be each independently 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.

[0357] 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.

[0358] [Compound Group 3]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366] In compound group 3, D represents a deuterium atom, and Ph represents an unsubstituted phenyl group.

[0367] 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.

[0368] 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 band gap of each host material. The triplet energy level of the exciplex may be less than or equal to about 3.0 eV, which is the energy band gap between the hole transport host and the electron transport host.

[0369] In an embodiment, the emission layer EML may further 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. Energy may be transferred from the fourth compound to the first compound, thereby achieving light emission.

[0370] 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 fourth compound represented by Formula D-1.

[0371] [Formula D-1]

[0372]

[0373] In formula D-1, Q 1 To Q 4 They may each independently be C or N.

[0374] In Formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 ring carbon atoms.

[0375] In formula D-1, L 11 To L 13 Can be directly connected, *-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. 11 To L 13 In the formula (a), -* indicates a bond to one of C1 to C4.

[0376] In formula D-1, b11 to b13 may each independently be 0 or 1. When b11 is 0, C1 and C2 may not be directly connected. If b12 is 0, C2 and C3 may not be directly connected. If b13 is 0, C3 and C4 may not be directly connected to each other.

[0377] In formula D-1, R 61 To R 66Each 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 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 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, or may be combined with adjacent groups to form a ring. For example, R 61 To R 66 Each independently may be a substituted or unsubstituted methyl group, or a substituted or unsubstituted tert-butyl group.

[0378] In Formula D-1, d1 to d4 may each independently be an integer of 0 to 4. If d1 to d4 are each 0, the fourth compound may not be respectively 61 To R 64 d1 to d4 are 4 and R 61 To R 64 The case where each of the four groups is a hydrogen atom may be the same as the case where each of d1 to d4 is 0. If each of d1 to d4 is 2 or more, then R 61 To R 64 The respective multiple groups may all be the same, or at least one of them may be different from the remaining groups.

[0379] 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.

[0380]

[0381] 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 ).

[0382] In Formula C-1 to Formula C-4, R 71 To R 88 Each may be independently 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, or may be combined with an adjacent group to form a ring.

[0383] In Formula C-1 to Formula C-4, represents a bond with Pt, and -* represents a bond with an adjacent ring group (C1 to C4) or with a connecting portion (L 11 To L 13 ) key.

[0384] In an embodiment, the emission layer EML may include a first compound represented by Formula 1, and 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, and energy may be transferred from the exciplex to the first compound, thereby achieving light emission.

[0385] 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, and energy may be transferred from the exciplex to the fourth compound and the first compound, thereby achieving luminescence. 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 for transferring energy from a host (e.g., an exciplex host) to a first compound as a light-emitting dopant. For example, the fourth compound used as an auxiliary dopant may accelerate energy transfer to the first compound used 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 transfer to the first compound increases, the excitons formed in the emission layer EML will not accumulate and light may be emitted quickly, thereby reducing the degradation of the light-emitting element ED. Therefore, the life of the light-emitting element ED may be extended.

[0386] 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, and therefore, the light emitting element ED may exhibit excellent emission efficiency properties.

[0387] 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.

[0388] [Compound Group 4]

[0389]

[0390]

[0391] In compound group 4, D represents a deuterium atom.

[0392] In an embodiment, the light emitting element ED may include a plurality of emission layers. The plurality of emission layers may be provided as a stack so that the light emitting element ED including the plurality of emission layers may emit white light. The light emitting element ED including the plurality of emission layers may be a light emitting element having a series structure. If the light emitting element ED includes a plurality of emission layers, 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, at least one emission layer EML may include a first compound, a second compound, a third compound, and a fourth compound.

[0393] In the light emitting element ED, 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.

[0394] 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 except for 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 combined amount of the second compound and the third compound may be in the range of about 65 wt % to about 95 wt %.

[0395] 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.

[0396] If the 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 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 emission efficiency may be reduced, and the device may be easily degraded.

[0397] If the emission layer EML includes a fourth compound, the amount of the fourth compound in the emission layer EML 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. 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 may be increased, so that the emission ratio may be improved. Therefore, the emission efficiency of the emission layer EML may 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 may be achieved.

[0398] In the light emitting element ED, the emission layer EML may further include anthracene derivatives, pyrene derivatives, fluoranthene derivatives, Derivatives, dihydrobenzanthracene derivatives or triphenylene derivatives. For example, the emission layer EML may include anthracene derivatives or pyrene derivatives.

[0399] In such Figures 3 to 6 In the light emitting element ED according to the embodiment shown in each of the drawings, 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.

[0400] 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.

[0401] [Formula E-1]

[0402]

[0403] In formula E-1, R 31 To R 40 Each of R and R may independently be 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 having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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, or may be combined with adjacent groups to form a ring. For example, 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.

[0404] In Formula E-1, c and d may each independently be an integer of 0 to 5.

[0405] In an embodiment, the compound represented by Formula E-1 may be any compound selected from Compound E1 to Compound E19.

[0406]

[0407]

[0408] 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.

[0409] [Formula E-2a]

[0410]

[0411] In formula E-2a, a may be an integer from 0 to 10; and L a It may be a directly linked, 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. If a is 2 or more, then multiple L a 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.

[0412] In formula E-2a, A 1 To A 5 can be N or C (R i ). In Formula E-2a, R a To R i Each of them may independently be 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, or may 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.

[0413] In formula E-2a, A 1 To A 5 Two or three of them can each be N, and A 1 To A 5 The remaining groups in may be independently C(R i ).

[0414] [Formula E-2b]

[0415]

[0416] In Formula E-2b, Cbz1 and Cbz2 may each independently be an unsubstituted carbazole group or a carbazole group substituted with an aromatic group having 6 to 30 ring carbon atoms. b It may be a directly linked, 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. If b is 2 or greater, then the plurality of 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.

[0417] The compound represented by Formula E-2a or Formula E-2b may be any 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.

[0418] [Compound Group E-2]

[0419]

[0420]

[0421]

[0422] The emission layer EML may also include a material of the related art as a host material. For example, the emission layer EML may include at least one of the following as a host material: 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(diphenylphosphoryl)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). However, the embodiment is not limited thereto. For example, tris(8-hydroxyquinolinyl)aluminum (Alq 3), 9,10-di(naphthalene-2-yl)anthracene (ADN), 2-tert-butyl-9,10-di(naphthalene-2-yl)anthracene (TBADN), distyrene (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 (UGH2), hexaphenylcyclotrisiloxane (DPSiO 3 ), octaphenylcyclotetrasiloxane (DPSiO 4 ) etc. can be used as the main material.

[0423] 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.

[0424] [Formula]

[0425]

[0426] 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 each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted sulfenyl 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, or combine 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.

[0427] The compound represented by the formula Ma may be any compound selected from the group consisting of the compounds M-a1 to M-a25. However, the compounds M-a1 to M-a25 are merely examples, and the compound represented by the formula Ma is not limited to the compounds M-a1 to M-a25.

[0428]

[0429]

[0430]

[0431] In an embodiment, the emission layer EML may further include a compound represented by one of Formulas Fa to Fc. The compound represented by one of Formulas Fa to Fc may be used as a fluorescent dopant material.

[0432] [Formula]

[0433]

[0434] In the formula Fa, R a To R j The two of them can be independently represented by *-NAr 1 Ar 2 The group represented by R is substituted. a To R j The unresolved *-NAr 1 Ar 2 The remaining groups substituted by the groups represented can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine 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.

[0435] In *-NAr 1 Ar 2 In the group represented by 1 and Ar 2 and Ar 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. 1 and Ar 2 At least one of them may each independently be a heteroaryl group including O or S as a ring-forming atom.

[0436] [Formula Fb]

[0437]

[0438] 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, or may be combined with adjacent groups to form a ring. 1 To Ar 4and Ar 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. 1 To Ar 4 At least one of them may each independently be a heteroaryl group including O or S as a ring-forming atom.

[0439] 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.

[0440] In formula Fb, the number of rings represented by U and V (hereinafter, referred to as the number of U, the number of V) may be 0 or 1 independently of each other. If the number of U or V is 1, a fused ring may be present at the portion indicated by U or V, and if the number of U or V is 0, a 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 U and V is each 0, the fused ring of the fluorene core of formula Fb may be a cyclic compound with three rings. If the number of U and V is each 1, the fused ring of the fluorene core of formula Fb may be a cyclic compound with five rings.

[0441] [Formula Fc]

[0442]

[0443] 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 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 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 having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or may be combined with adjacent groups to form a ring.

[0444] In Formula Fc, A 1 and A2 Can each independently combine with the substituents of the adjacent ring to form a fused ring. For example, if A 1 and A 2 Each independently is 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.

[0445] In an embodiment, the emission layer EML may include a styryl derivative (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 or its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene or its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenylbenzene and 1,4-bis(N,N-diphenylamino)pyrene), and the like as a dopant material of the related art.

[0446] The emission layer EML may include a phosphorescent dopant material of the related art. For example, the phosphorescent dopant may include 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') iridium (III) picolinate (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.

[0447] In an embodiment, the emissive layer may include quantum dots.

[0448] In the specification, quantum dots may be crystals of semiconductor compounds. The quantum dots may emit light in various emission wavelengths depending on the size of the crystals. By controlling the element ratio of the quantum dot compound, the quantum dots may emit light in various emission wavelengths.

[0449] The diameter of a quantum dot may be, for example, in the range of about 1 nm to about 10 nm.

[0450] Quantum dots can be synthesized by chemical bath deposition, metal organic chemical vapor deposition, molecular beam epitaxy, or by similar processes.

[0451] Chemical bath deposition is a method of mixing an organic solvent and a precursor material and growing quantum dot particle crystals. While growing the crystals, the organic solvent can be used as a dispersant coordinated on the surface of the quantum dot crystals, and the growth of the crystals can be controlled. Therefore, when compared to vapor deposition methods such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE), chemical bath deposition may be more advantageous and the growth of quantum dot particles can be controlled through a low-cost process.

[0452] In an embodiment, the emission layer EML may include a quantum dot material. The quantum dot may be a II-VI compound, a III-VI compound, an I-III-VI compound, a III-V compound, a III-II-V compound, a IV-VI compound, a IV element, a IV compound, or any combination thereof.

[0453] 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, CdZ nTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof; and 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.

[0454] In an embodiment, the II-VI group compound may further include a group I metal and / or a group IV element. Examples of the I-II-VI group compound may include CuZnS, etc. Examples of the II-IV-VI group compound may include ZnSnS, etc. Examples of the I-II-IV-VI group compound may include a group selected from Cu 2 ZnSnS 2 , Cu 2 ZnSnS 4 , Cu 2 ZnSnSe 4 、Ag 2ZnSnS 2 and mixtures thereof constitute a group of quaternary compounds.

[0455] 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.

[0456] 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.

[0457] 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. Examples of the III-II-V group compound may include InZnP and the like.

[0458] Examples of IV-VI 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.

[0459] Examples of II-IV-V group compounds may include compounds selected from ZnSnP, ZnSnP 2 、ZnSnAs 2 、ZnGeP 2 、ZnGeAs 2 、CdSnP 2 、CdGeP 2 and mixtures thereof constitute a group of ternary compounds.

[0460] Examples of the Group IV element may include Si, Ge, and mixtures thereof. Examples of the Group IV compound may include a binary compound selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0461] 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, a formula may indicate the elements included in the compound, but the ratio of the elements in the compound may vary. For example, AgInGaS 2 Can indicate AgIn x Ga 1-x S 2 (where x is a real number between 0 and 1).

[0462] The binary, ternary or quaternary compound may be present in the particle at a uniform concentration, or may be present in the particle in a partially different concentration distribution state. In an embodiment, the quantum dot may have a core / shell structure in which one quantum dot surrounds another quantum dot. The interface between the core and the shell may have a concentration gradient in which the concentration of the element present in the shell decreases toward the core.

[0463] In an embodiment, the quantum dot may have the above-mentioned core-shell structure, which includes a core having nanocrystals and a shell surrounding the core. The shell of the quantum dot may be used as a protective layer to prevent chemical changes in the core to maintain semiconductor properties, and / or may be used as a charging layer to impart electrophoretic properties to the quantum dot. The shell may have a single-layer structure or a multi-layer structure. Examples of the shell of the quantum dot may include metal oxides, non-metal oxides, semiconductor compounds, or any combination thereof.

[0464] 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 O 4 , CoO, Co 3 O 4 and NiO; or ternary compounds such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 and CoMn 2 O 4 However, the embodiments are not limited thereto.

[0465] 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.

[0466] The quantum dots may have a full width at half maximum (FWHM) of an emission spectrum equal to or less than about 45 nm. For example, the quantum dots may have a FWHM of an emission spectrum equal to or less than about 40 nm. For example, the quantum dots may have a FWHM of an emission 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 by quantum dots may be emitted in all directions, thereby improving light viewing angle properties.

[0467] The shape of the quantum dot can be any shape used in the related art. For example, the quantum dot can have a spherical shape, a pyramidal shape, a multi-arm shape or a cubic shape, or the quantum dot can be in the form of nanoparticles, nanotubes, nanowires, nanofibers, nanoplates, etc.

[0468] When the size of the quantum dot or the element ratio of the quantum dot compound is adjusted, the energy 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 element that emits light of various wavelengths can be realized. For example, the size of the quantum dot or the element ratio of 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.

[0469] In such Figures 3 to 6 In the light emitting element ED according to the embodiment shown in each of the drawings, 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.

[0470] The electron transport region ETR 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.

[0471] 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 of 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 different materials, or may have a structure in which an electron transport layer ETL / electron injection layer EIL or a hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL are stacked from the emission layer EML in their respective stated order, but the embodiment is not limited thereto. The thickness of the electron transport region ETR may be, for example, about 1000 Å. To about within the range.

[0472] 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.

[0473] In the light emitting element ED according to the embodiment, the electron transport region ETR may include a compound represented by Formula ET-2.

[0474] [Formula ET-2]

[0475]

[0476] In formula ET-2, X 1 To X 3 At least one of may each be N; and X 1 To X 3 The remaining groups in may be independently C(R a ). In formula ET-2, R a 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 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms. 1 To Ar 3 Each 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.

[0477] In Formula ET-2, a to c may each independently be an integer of 0 to 10. In Formula ET-2, L 1 To L 3 Each of L and L is independently a directly linked, 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 the plurality of groups may be each independently 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.

[0478] 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-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (B phen), 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 (tBu-PBD), bis(2-methyl-8-hydroxyquinolinolato-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(10-hydroxybenzoquinolinolato)beryllium (Bebq 2 ), 9,10-di(naphthalene-2-yl)anthracene (ADN), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB), CNNPTRZ (4'-(4-(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)naphthalene-1-yl)-[1,1'-biphenyl]-4-carbonitrile), or mixtures thereof, but are not limited thereto.

[0479] In an embodiment, the electron transport region ETR may include a compound selected from compound group 3.

[0480] In an embodiment, the electron transport region ETR may include at least one compound selected from the group consisting of compounds ET1 to ET36.

[0481]

[0482]

[0483]

[0484]

[0485] In an embodiment, 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 halide such as Li 2O and BaO metal oxide, or 8-hydroxy-quinoline lithium (Liq). However, the embodiment is not limited thereto. The electron transport region ETR can also be formed by a mixture material of an electron transport material and an insulating organic metal salt. The insulating organic metal salt can be a material having an energy band gap equal to or greater than about 4eV. For example, the insulating organic metal salt can include a metal acetate, a metal benzoate, a metal acetoacetate, a metal acetylacetonate, or a metal stearate.

[0486] In addition to the aforementioned 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.

[0487] 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.

[0488] 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 thickness of the electron transport layer ETL can be about To about If the thickness of the electron transport layer ETL satisfies any 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 of the above ranges, satisfactory electron injection properties can be obtained without causing a significant increase in driving voltage.

[0489] 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.

[0490] The second electrode EL2 may be a transmissive electrode, a semi-transmissive reflective electrode or a reflective electrode. If the second electrode EL2 is a transmissive electrode, the second electrode EL2 may include a transparent metal oxide such as ITO, IZO, ZnO, ITZO or the like.

[0491] If the second electrode EL2 is a semi-transmissive reflective 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, a compound thereof, or a mixture 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 semi-transmissive reflective 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 aforementioned metal material, a combination of two or more metal materials selected from the aforementioned metal materials, or an oxide of the aforementioned metal material.

[0492] 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.

[0493] 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.

[0494] 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 alkali metal compound such as MgF 2 Alkaline earth metal compounds, SiON, SiN x 、SiO y wait.

[0495] 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 may include epoxy resins or acrylate resins such as methacrylate. In an embodiment, the cover layer CPL may include at least one of compounds P1 to P5, but the embodiment is not limited thereto.

[0496]

[0497]

[0498] The refractive index of the cover layer CPL may be equal to or greater than about 1.6. For example, with respect to light in a wavelength range of about 550 nm to about 660 nm, the refractive index of the cover layer CPL may be equal to or greater than about 1.6.

[0499] Figures 7 to 10 Each is a schematic cross-sectional view of a display device according to an embodiment. Figures 7 to 10 In the description of the display device according to the embodiment shown in FIG. 1 , the above description of the display device according to the embodiment will not be repeated. Figures 1 to 6 The features described, and the different features will be explained.

[0500] refer to Figure 7 The display device DD-a according to the embodiment may include a display panel DP, a light control layer CCL disposed on the display panel DP, and a color filter layer CFL, and the display panel DP includes a display device layer DP-ED.

[0501] exist Figure 7 In the embodiment shown in , the display panel DP includes a base layer BS, a circuit layer DP-CL provided 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.

[0502] 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. In an embodiment, Figure 7 The structure of the light emitting element ED shown in FIG. 1 can be the same as that described above according to Figures 3 to 6 The structure of the light emitting element ED in one of the above is the same.

[0503] The emission layer EML of the light emitting element ED included in the display device DD-a according to the embodiment may include the condensed polycyclic compound according to the embodiment as described above.

[0504] refer to Figure 7, the emission layer EML may be disposed 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 provided to each of the light emitting regions PXA-R, PXA-G, and PXA-B accordingly may emit light in the same wavelength region. In the display device DD-a, the emission layer EML may emit blue light. Although not shown in the drawings, in an embodiment, the emission layer EML may be provided as a common layer for each of the light emitting regions PXA-R, PXA-G, and PXA-B.

[0505] 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.

[0506] The light-controlling layer CCL may include light-controlling parts CCP1, CCP2, and CCP3. The light-controlling parts CCP1, CCP2, and CCP3 may be spaced apart from each other.

[0507] refer to Figure 7 , the separation pattern BMP may be disposed between the light-controlling parts CCP1, CCP2, and CCP3 that are spaced apart from each other, but the embodiment is not limited thereto. Figure 7 , it is shown that the separation pattern BMP does not overlap with the light-controlling portions CCP1 , CCP2 , and CCP3 , but edges of the light-controlling portions CCP1 , CCP2 , and CCP3 may overlap with at least a portion of the separation pattern BMP.

[0508] 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 includes a first quantum dot QD1 that converts a first color light provided from the light emitting element ED into a second color light, the second light control part CCP2 includes a second quantum dot QD2 that converts the first color light into a third color light, and the third light control part CCP3 transmits the first color light.

[0509] 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 each be a quantum dot as described above.

[0510] The light control layer CCL may further include a scatterer SP. The first light control part CCP1 may include first quantum dots QD1 and a scatterer SP, the second light control part CCP2 may include second quantum dots QD2 and a scatterer SP, and the third light control part CCP3 may not include quantum dots but may include a scatterer SP.

[0511] The scatterer SP may be inorganic particles. For example, the scatterer SP may include TiO 2 、ZnO、Al 2 O 3 and SiO 2 The scatterer SP may include TiO 2 、ZnO、Al 2 O 3 and SiO 2 (such as hollow silica), or may be selected from TiO 2 、ZnO、Al 2 O 3 and SiO 2 A mixture of two or more materials in a hollow silica.

[0512] The first light control part CCP1, the second light control part CCP2, and the third light control part CCP3 may each include base resins BR1, BR2, and BR3 in which quantum dots QD1 and QD2 and scatterers SP are dispersed. In an embodiment, the first light control part CCP1 may include first quantum dots QD1 and scatterers SP dispersed in the first base resin BR1, the second light control part CCP2 may include second quantum dots QD2 and scatterers SP dispersed in the second base resin BR2, and the third light control part CCP3 may include scatterers SP dispersed in the third base resin BR3.

[0513] The matrix resins BR1, BR2 and BR3 are the medium in which the quantum dots QD1 and QD2 and the scatterers SP are dispersed, and may be composed of various resin compositions that may generally be referred to as adhesives. 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 each be a transparent resin. 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.

[0514] The light control layer CCL may include a blocking layer BFL1. The blocking layer BFL1 may block 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 described later, may include a blocking layer BFL2 disposed on the light control parts CCP1, CCP2, and CCP3.

[0515] The barrier layers BFL1 and BFL2 may each independently include at least one inorganic layer. For example, the barrier layers BFL1 and BFL2 may each independently include 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, silicon oxynitride, or a metal film that ensures light transmittance. The barrier layers BFL1 and BFL2 may each independently further include an organic layer. The barrier layers BFL1 and BFL2 may each be formed by a single layer or by a multilayer.

[0516] In the display device DD-a, the color filter layer CFL may be disposed on the light control layer CCL. In an embodiment, the color filter layer CFL may be directly disposed on the light control layer CCL. For example, the blocking layer BFL2 may be omitted.

[0517] The color filter layer CFL may include color filters CF1, CF2, and CF3. The first, second, and third color filters CF1, CF2, and CF3 may be disposed to correspond to the red, green, and blue light emitting regions PXA-R, PXA-G, and PXA-B, respectively.

[0518] The color filter layer CFL may include a first color filter CF1 that transmits a second color light, a second color filter CF2 that transmits a third color light, and a third color filter CF3 that transmits the first color light. For example, the first color filter CF1 may be a red color filter, the second color filter CF2 may be a green color filter, and the third color filter CF3 may be a blue color filter. The color filters CF1, CF2, and CF3 may each include a polymer photosensitive resin and a pigment or dye. The first color filter CF1 may include a red pigment or dye, the second color filter CF2 may include a green pigment or dye, and the third color filter CF3 may include a blue pigment or dye.

[0519] However, the embodiment is not limited thereto, and the third color filter CF3 may not include a pigment or dye. The third color filter CF3 may include a polymer photosensitive resin and may not include a pigment or dye. The third color filter CF3 may be transparent. The third color filter CF3 may be formed of a transparent photosensitive resin.

[0520] In an embodiment, the first color filter CF1 and the second color filter CF2 may each be a yellow color filter. The first filter CF1 and the second filter CF2 may be provided as one body without distinction.

[0521] 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, each of which includes a black pigment or a black dye. The light blocking portion (not shown) may prevent light leakage and may separate the boundaries between the adjacent color filters CF1, CF2, and CF3.

[0522] 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 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.

[0523] Figure 8 is 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 light emitting structures OL-B1, OL-B2, and OL-B3.

[0524] The light emitting element ED-BT may include a first electrode EL1 and a second electrode EL2 facing each other and light emitting structures OL-B1, OL-B2, and OL-B3 stacked in a thickness direction between the first electrode EL1 and the second electrode EL2. The light emitting structures OL-B1, OL-B2, and OL-B3 may each include a hole transport region HTR, an emission layer EML (see Figure 7 ) and electron transport region ETR.

[0525] For example, the light emitting elements ED-BT included in the display devices DD-TD may be light emitting elements having a tandem structure and including a plurality of emission layers.

[0526] exist Figure 8In the embodiment shown in , the light emitted from the light emitting structures OL-B1, OL-B2, and OL-B3 may each be blue light. However, the embodiment is not limited thereto, and the light emitted from each of the light emitting structures OL-B1, OL-B2, and OL-B3 may have a wavelength range different from each other. For example, the light emitting element ED-BT including the light emitting structures OL-B1, OL-B2, and OL-B3 emitting light having a wavelength range different from each other may emit white light.

[0527] The charge generation layers CGL1 and CGL2 may each be disposed between adjacent light emitting structures among the 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.

[0528] At least one of the light emitting structures OL-B1, OL-B2, and OL-B3 in the display devices DD-TD may include the condensed polycyclic compound according to the embodiment. For example, at least one of the emission layers included in the light emitting elements ED-BT may include the condensed polycyclic compound.

[0529] 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.

[0530] refer to Fig. 9 , the display device DD-b according to the embodiment may include light emitting elements ED-1, ED-2, and ED-3 in which two emission layers are stacked. Figure 2 Compared with the display device DD shown in Fig. 9 The embodiment shown in the embodiment is different at least in that the first light-emitting element ED-1, the second light-emitting element ED-2 and the third light-emitting element ED-3 each include two emission layers stacked in the thickness direction. In each of the first light-emitting element ED-1, the second light-emitting element ED-2 and the third light-emitting element ED-3, the two emission layers can emit light in the same wavelength region.

[0531] 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 portion OG may be disposed 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.

[0532] 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 stacked in the following order. The emission auxiliary part OG may be provided as a common layer for each of the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3. However, the embodiment is not limited thereto, and the emission auxiliary part OG may be provided by patterning in the opening OH defined in the pixel defining film PDL.

[0533] 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, respectively. 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, respectively.

[0534] 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 the following 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 the following 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 the following order.

[0535] 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 the reflection of the display panel DP to external light. Although not shown in the drawings, in an embodiment, the optical auxiliary layer PL may be omitted from the display device DD-b.

[0536] Included in Fig. 9 At least one emission layer in the display device DD-b shown in FIG. 1 may include the condensed polycyclic compound according to the embodiment described above. For example, in the embodiment, at least one of the first blue emission layer EML-B1 and the second blue emission layer may include a condensed polycyclic compound.

[0537] and Figure 8 and Fig. 9 compared to, Fig.10 A display device DD-c is shown, which differs 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 facing each other and a first light emitting structure OL-B1, a second light emitting structure OL-B2, a third light emitting structure OL-B3, and a fourth light emitting structure OL-C1 stacked in the thickness direction between the first electrode EL1 and the second electrode EL2. In an embodiment, 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 the order stated in the thickness direction.

[0538] The charge generation layers CGL1, CGL2, and CGL3 may be respectively disposed between adjacent light emitting structures among the first light emitting structure OL-B1, the second light emitting structure OL-B2, the third light emitting structure OL-B3, and the fourth light emitting structure 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. For example, 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. For example, 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.

[0539] Among the four light emitting structures, the first light emitting structure OL-B1, the second light emitting structure OL-B2, and the third light emitting structure 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 light emitting structure OL-B1, the second light emitting structure OL-B2, the third light emitting structure OL-B3, and the fourth light emitting structure OL-C1 may emit light having different wavelengths from each other.

[0540] The charge generation layers CGL1, CGL2, and CGL3 disposed between adjacent light emitting structures among the first, second, third, and fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may each independently include a p-type charge generation layer and / or an n-type charge generation layer.

[0541] In the display device DD-c, at least one of the first light emitting structure OL-B1, the second light emitting structure OL-B2, the third light emitting structure OL-B3, and the fourth light emitting structure OL-C1 may each independently include a fused polycyclic compound according to the embodiment as described herein. For example, in the embodiment, at least one of the first light emitting structure OL-B1, the second light emitting structure OL-B2, the third light emitting structure OL-B3, and the fourth light emitting structure OL-C1 may each independently include a fused polycyclic compound.

[0542] The light emitting element ED according to the embodiment may include the fused polycyclic compound according to the embodiment in at least one functional layer disposed between the first electrode EL1 and the second electrode EL2, thereby exhibiting excellent emission efficiency and improved lifespan characteristics. For example, the emission layer EML of the light emitting element ED may include the fused polycyclic compound, and the light emitting element ED may exhibit a long lifespan.

[0543] In an embodiment, the electronic device may include a display device and a control portion, the display device including a plurality of light emitting elements, and the control portion controlling the display device. The electronic device may be a device activated according to an electrical signal. The electronic device may include a display device according to various embodiments. Examples of electronic devices may include large display devices such as televisions, monitors, or billboards, and medium or small display devices such as personal computers, laptop computers, personal digital terminals, display devices for vehicles, game consoles, portable electronic devices, or cameras.

[0544] Fig.11 is a schematic perspective view of a vehicle AM ​​including a first display device DD-1, a second display device DD-2, a third display device DD-3, and a fourth display device DD-4 according to an embodiment. At least one of the first display device DD-1, the second display device DD-2, the third display device DD-3, and the fourth display device DD-4 may have a display device according to the above reference Figure 1 , Figure 2 and Figures 7 to 10 The structure of one of the display devices DD, DD-TD, DD-a, DD-b and DD-c is described.

[0545] exist Fig.11In the embodiment, the vehicle AM ​​is shown as a car, but this is only an example, and the first display device DD-1, the second display device DD-2, the third display device DD-3, and the fourth display device DD-4 may be provided in various vehicles such as bicycles, motorcycles, trains, ships, or airplanes. In the embodiment, at least one of the first display device DD-1, the second display device DD-2, the third display device DD-3, and the fourth display device DD-4, each having a structure according to one of the display devices DD, DD-TD, DD-a, DD-b, and DD-c, may be included in a personal computer, a laptop computer, a personal digital terminal, a game console, a portable electronic device, a television, a monitor, or a billboard, etc. However, these are only suggested as examples, and the display device may be included in other electronic devices.

[0546] At least one of the first display device DD-1, the second display device DD-2, the third display device DD-3, and the fourth display device DD-4 may each independently include a Figures 3 to 6 The light emitting element ED according to the embodiment is described in any of the drawings in FIG. The light emitting element ED may include the fused polycyclic compound according to the embodiment. At least one of the first display device DD-1, the second display device DD-2, the third display device DD-3, and the fourth display device DD-4 may include the light emitting element ED including the fused polycyclic compound according to the embodiment, thereby exhibiting an extended display life.

[0547] refer to Fig.11 The vehicle AM ​​may include a steering wheel HA and a shift lever GR for operation of the vehicle AM. The vehicle AM ​​may include a front window GL disposed to face the driver.

[0548] 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 vehicle AM. The first information may include a first scale indicating the travel speed of the vehicle AM, a second scale indicating the engine speed (e.g., as revolutions per minute (RPM)), a fuel gauge, and the like. The first scale and the second scale may be represented by digital images.

[0549] 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) that displays the second information of the vehicle AM. The second display device DD-2 can be optically transparent. The second information may include a digital number indicating the driving speed of the vehicle AM, and may also include information such as the current time. Although not shown in the accompanying drawings, in an embodiment, the second information of the second display device DD-2 can be displayed by projecting onto the front window GL.

[0550] The third display device DD-3 may be disposed in a third area adjacent to the shift lever GR. For example, the third display device DD-3 may be a central information display (CID) for the vehicle AM ​​disposed between the driver's seat and the passenger seat and displaying the third information. The passenger seat may be a seat spaced apart from the driver's seat, and the shift lever GR may be disposed between the driver's seat and the passenger seat. The third information may include information on traffic or road conditions (e.g., navigation information), playing music or radio, displaying images or videos, or the temperature in the vehicle AM.

[0551] The fourth display device DD-4 may be disposed in a fourth area spaced apart from the steering wheel HA and the shift lever GR and adjacent to one side of the vehicle AM. For example, the fourth display device DD-4 may be a digital side mirror that displays the fourth information. The fourth display device DD-4 may display an image of the exterior of the vehicle AM ​​captured by a camera module CM disposed outside the vehicle AM. The fourth information may include an image of the exterior of the vehicle AM.

[0552] The first to fourth information described above are provided only as examples, and the first display device DD-1, the second display device DD-2, the third display device DD-3, and the fourth display device DD-4 may also display information about the interior and exterior of the vehicle AM. The first to fourth information may include information different from each other. However, the embodiment is not limited thereto, and part of the first to fourth information may include the same information.

[0553] Hereinafter, a fused polycyclic compound according to an embodiment and a light emitting element according to an embodiment will be described with reference to examples and comparative examples. The examples described below are provided only as illustrations to help understand the present disclosure, and the scope thereof is not limited thereto.

[0554] [Example]

[0555] 1. Synthesis of fused polycyclic compounds

[0556] The synthesis method of the fused polycyclic compound according to the embodiment will be explained by the synthesis method of the described compound 2, compound 3, compound 34, compound 66, compound 78, compound 83, compound 101, compound 107, compound 113 and compound 117. The synthesis method of the fused polycyclic compound described 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.

[0557] (1) Synthesis of Compound 2

[0558] Compound 2 according to the example can be synthesized by, for example, the following reaction.

[0559] (Synthesis of Intermediate 2-a)

[0560]

[0561] Under argon atmosphere, 1,3-dibromo-5-(tert-butyl)benzene (2 equivalents), 5'-(tert-butyl)-[1,1':3',1"-terphenyl]-2'-amine (1 equivalent), Pd 2 (dba) 3 A compound of 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP, 0.1 equivalent) and sodium tert-butoxide (3 equivalents) was dissolved in toluene, and the reaction solution was stirred at about 100° C. for about 12 hours. After cooling, water and ethyl acetate were added, extraction was performed, and the organic layer was collected and filtered through MgSO 4 The filtrate was dried and filtered. The solvent was removed under reduced pressure and the filtrate was purified by using CH 2 Cl 2 The solid thus obtained was purified and separated by column chromatography using 4,4-dihydro-1,4-dihydro-2-pyrrolidone and hexane as a developing solvent to obtain Intermediate 2-a (yield: 65%). The compound thus obtained was identified as Intermediate 2-a by electrospray ionization-liquid chromatography-mass spectrometry (ESI-LCMS).

[0562] ESI-LCMS: [M] + :C 32 H 34 BrN, 511.1870.

[0563] (Synthesis of Intermediate 2-b)

[0564]

[0565] Under an argon atmosphere, intermediate 2-a (1 equivalent), 1-chloro-3-iodobenzene (1.5 equivalents), cuprous iodide (1 equivalent), 1,10-phenanthroline (1 equivalent) and potassium carbonate (3 equivalents) were added to a 1L flask and dissolved in N,N-dimethylformamide (DMF), and the reaction solution was stirred at about 160° C. for about 12 hours. After cooling, water and ethyl acetate were added, extraction was performed, and the organic layer was collected and filtered through MgSO 4 The filtrate was dried and filtered. The solvent was removed under reduced pressure and the filtrate was purified by using CH 2 Cl 2 The solid thus obtained was purified and separated by column chromatography using 4% paraformaldehyde and hexane as a developing solvent, thereby obtaining Intermediate 2-b (yield: 42%). The compound thus obtained was identified as Intermediate 2-b by ESI-LCMS.

[0566] ESI-LCMS: [M] + :C 38 H 37 BrClN, 621.1798.

[0567] (Synthesis of Intermediate 2-c)

[0568]

[0569] Under argon atmosphere, intermediate 2-b (1 equivalent), 5'-(tert-butyl)-[1,1':3',1"-terphenyl]-2'-amine (1.1 equivalent), Pd 2 (dba) 3 (0.05 equivalent), tri-tert-butylphosphine (0.1 equivalent) and sodium tert-butoxide (3 equivalents) were added and dissolved in toluene, and the reaction solution was stirred at about 110° C. for about 12 hours. After cooling, water and ethyl acetate were added, extraction was performed, and the organic layer was collected and filtered through MgSO 4 The filtrate was dried and filtered. The solvent was removed under reduced pressure and the filtrate was purified by using CH 2 Cl 2 The solid thus obtained was purified and separated by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene)2 and hexane as a developing solvent, thereby obtaining Intermediate 2-c (yield: 72%). The compound thus obtained was identified as Intermediate 2-c by ESI-LCMS.

[0570] ESI-LCMS: [M] + :C 60 H 59 C1N 2 , 842.4360.

[0571] (Synthesis of Intermediate 2-d)

[0572]

[0573] Under an argon atmosphere, intermediate 2-c (1 equivalent), iodobenzene (1.5 equivalents), cuprous iodide (1 equivalent), 1,10-phenanthroline (1 equivalent) and potassium carbonate (3 equivalents) were added to a 1 L flask and dissolved in DMF, and the reaction solution was stirred at about 160° C. for about 12 hours. After cooling, water and ethyl acetate were added, extraction was performed, and the organic layer was collected and filtered through MgSO 4 The solvent of the filtrate was removed under reduced pressure and the mixture was purified by using CH 2 Cl 2 The solid thus obtained was purified and separated by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene)2 and hexane as a developing solvent, thereby obtaining Intermediate 2-d (yield: 53%). The compound thus obtained was identified as Intermediate 2-d by ESI-LCMS.

[0574] ESI-LCMS: [M] + :C 66 H 63 C1N 2 , 918.4680.

[0575] (Synthesis of Intermediate 2-e)

[0576]

[0577] Under argon atmosphere, intermediate 2-d (1 equivalent) was added to a 500 mL flask, dissolved in o-dichlorobenzene, and cooled with water-ice, and BBr was slowly added dropwise thereto. 3 (5 eq.), followed by stirring at about 180 °C for about 12 h. After cooling, triethylamine (5 eq.) was added to quench the reaction, and water and CH 2 Cl 2 Extraction was performed, and the organic layer was collected and filtered through MgSO 4 The filtrate was dried and filtered. The solvent was removed under reduced pressure and the filtrate was purified by using CH 2 Cl 2 The solid thus obtained was purified and separated by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solvent, thereby obtaining Intermediate 2-e (yellow solid, yield: 23%). The compound thus obtained was identified as Intermediate 2-e by ESI-LCMS.

[0578] ESI-LCMS: [M] + :C 66 H 60 BCN 2 , 926.4538.

[0579] (Synthesis of Intermediate 2-f)

[0580]

[0581] Under an argon atmosphere, intermediate 2-e (1 equivalent) was added to a 500 mL flask, dissolved in dichloromethane, and cooled with water-ice, and N-bromosuccinimide (NBS, 1 equivalent) was slowly added dropwise thereto, followed by stirring at room temperature for about 2 hours. 2 Cl 2 Extraction was performed, and the organic layer was collected and filtered through MgSO 4 The filtrate was dried and filtered. The solvent was removed under reduced pressure and the filtrate was purified by using CH 2 Cl 2 The solid thus obtained was purified and separated by column chromatography using 4,4-dihydro-1,4-dihydro-2-nitropropene and hexane as a developing solvent, thereby obtaining Intermediate 2-f (yield, 68%). The compound thus obtained was identified as Intermediate 2-f by ESI-LCMS.

[0582] ESI-LCMS: [M] + :C 66 H 59 BBrCl 2 , 1004.3640.

[0583] (Synthesis of Intermediate 2-g)

[0584]

[0585] Under argon atmosphere, intermediate 2-f (1 equivalent), (4-(triphenylsilyl)phenyl)boronic acid (1.2 equivalents), Pd(PPh 3 ) 4 (0.03 eq.) and potassium carbonate (2 eq.) and dissolved in toluene:ethanol:H 2 O (5:1:2), and the reaction solution was stirred at about 100° C. for about 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction, and the organic layer was collected and filtered through MgSO 4 The filtrate was dried and filtered. The solvent was removed under reduced pressure and the filtrate was purified by using CH 2 Cl 2 The solid thus obtained was purified and separated by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solvent, thereby obtaining Intermediate 2-g (yield: 70%). The compound thus obtained was identified as Intermediate 2-g by ESI-LCMS.

[0586] ESI-LCMS: [M] + :C 90 H 78 BCN2 Si, 1260.5716.

[0587] (Synthesis of Compound 2)

[0588]

[0589] Under argon atmosphere, intermediate 2-g (1 equivalent), 9H-carbazole-1,2,3,4,5,6,7,8-D8 (1.2 equivalents), Pd 2 (dba) 3 (0.05 equivalent), tri-tert-butylphosphine (0.1 equivalent) and sodium tert-butoxide (3 equivalents) were added and dissolved in o-xylene, and the reaction solution was stirred at about 140° C. for about 12 hours. After cooling, water and ethyl acetate were added, extraction was performed, and the organic layer was collected and filtered through MgSO 4 The filtrate was dried and filtered. The solvent was removed under reduced pressure and the filtrate was purified by using CH 2 Cl 2 The solid thus obtained was purified and separated by column chromatography using 1,4-dihydro- ... 1 The compound thus obtained was identified as Compound 2 by H-NMR) and ESI-LCMS.

[0590] 1 H-NMR (400MHz, CDCl 3 ):d=9.15(d,1H),9.12(s,1H),7.89-7.80(m,4H),7.75-7.65(m,4H),7.43-7.40(s,4H),7.38-7.28(m, 15H),7.20-7.12(m,12H),7.08-6.99(m,8H),6.20-6.18(s,2H),1.41-1.39(s,18H),1.35-1.32(s,9H).

[0591] ESI-LCMS: [M] + :C 102 H 78 D 8 BN 3 Si, 1399.7186.

[0592] (2) Synthesis of Compound 3

[0593] Compound 3 according to the example can be synthesized by, for example, the following reaction.

[0594] (Synthesis of Intermediate 3-a)

[0595]

[0596] According to the synthesis method for synthesizing intermediate 2-a, 5'-phenyl-[1,1':3',1"-terphenyl]-2'-amine was used instead of 5'-(tert-butyl)-[1,1':3',1"-terphenyl]-2'-amine to synthesize intermediate 3-a (yield: 56%). The solid thus obtained was identified as intermediate 3-a by ESI-LCMS.

[0597] ESI-LCMS: [M] + :C 34 H 30 BrN, 531.1562.

[0598] (Synthesis of Intermediate 3-b)

[0599]

[0600] According to the same method for synthesizing Intermediate 2-b, Intermediate 3-b was synthesized using Intermediate 3-a instead of Intermediate 2-a (yield: 69%). The solid thus obtained was identified as Intermediate 3-b by ESI-LCMS.

[0601] ESI-LCMS: [M] + :C 40 H 33 BrClN, 641.1485.

[0602] (Synthesis of Intermediate 3-c)

[0603]

[0604] According to the same method for synthesizing intermediate 2-c, intermediate 3-b was used instead of intermediate 2-b and 5'-phenyl-[1,1':3',1"-terphenyl]-2'-amine was used instead of 5'-(tert-butyl)-[1,1':3',1"-terphenyl]-2'-amine to synthesize intermediate 3-c (yield: 72%). The solid thus obtained was identified as intermediate 3-c by ESI-LCMS.

[0605] ESI-LCMS: [M] + :C 64 H 51 C1N 2 , 882.3741.

[0606] (Synthesis of Intermediate 3-d)

[0607]

[0608] According to the same method for synthesizing Intermediate 2-d, Intermediate 3-d was synthesized using Intermediate 3-c instead of Intermediate 2-c (yield: 71%). The solid thus obtained was identified as Intermediate 3-d by ESI-LCMS.

[0609] ESI-LCMS: [M] + :C 70 H 55 C1N 2 , 958.4054.

[0610] (Synthesis of Intermediate 3-e)

[0611]

[0612] According to the same method for synthesizing Intermediate 2-e, Intermediate 3-e was synthesized using Intermediate 3-d instead of Intermediate 2-d (yield: 20%). The solid thus obtained was identified as Intermediate 3-e by ESI-LCMS.

[0613] ESI-LCMS: [M] + :C 70 H 52 BCN 2 , 966.3912.

[0614] (Synthesis of Intermediate 3-f)

[0615]

[0616] According to the same method for synthesizing Intermediate 2-f, Intermediate 3-f was synthesized using Intermediate 3-e instead of Intermediate 2-e (yield: 51%). The solid thus obtained was identified as Intermediate 3-f by ESI-LCMS.

[0617] ESI-LCMS: [M] + :C 70 H 51 BBrCl 2 , 1044.3017.

[0618] (Synthesis of Intermediate 3-g)

[0619]

[0620] According to the same method for synthesizing Intermediate 2-g, Intermediate 3-g was synthesized using Intermediate 3-f instead of Intermediate 2-f (yield: 68%). The solid thus obtained was identified as Intermediate 3-g by ESI-LCMS.

[0621] ESI-LCMS: [M]+ :C 94 H 70 BCN 2 Si, 1300.5090.

[0622] (Synthesis of Compound 3)

[0623]

[0624] According to the same method used to synthesize compound 2, compound 3 (yellow solid, yield: 63%) was synthesized using intermediate 3-g instead of intermediate 2-g. 1 The yellow solid thus obtained was identified as Compound 3 by H-NMR and ESI-LCMS.

[0625] 1 H-NMR (400MHz, CDCl 3 ):d=9.14(d,1H),9.11(s,1H),7.85-7.80(m,4H),7.72-7.68(m,4H),7.44-7.43(s,4H),7.40-7.25(m, 15H),7.20-7.12(m,12H),7.10-7.02(m,8H),7.00-6.88(m,10H),6.19-6.18(s,2H),1.35-1.32(s,9H).

[0626] ESI-LCMS: [M] + :C 106 H 70 D 8 BN 3 Si, 1439.6560.

[0627] (3) Synthesis of compound 34

[0628] Compound 34 according to the example can be synthesized by, for example, the following reaction.

[0629] (Synthesis of Compound 34)

[0630]

[0631] According to the same method used to synthesize compound 2, compound 34 (yellow solid, yield: 72%) was synthesized using 3,6-di-tert-butyl-9H-carbazole instead of 9H-carbazole-1,2,3,4,5,6,7,8-D8. 1 The yellow solid thus obtained was identified as Compound 34 by H-NMR and ESI-LCMS.

[0632] 1H-NMR (400MHz, CDCl 3 ):d=9.15(d,1H),9.12(s,1H),8.45-8.33(m,6H),7.89-7.80(m,4H),7.75-7.65(m,4H),7.43-7.40(s,4H),7.38-7.28(m, 15H),7.20-7.12(m,12H),7.08-6.99(m,8H),6.20-6.18(s,2H),1.50-1.48(s,18H)1.41-1.39(s,18H),1.35-1.32(s,9H).

[0633] ESI-LCMS: [M] + :C 110 H 102 D 8 BN 3 Si, 1503.7685.

[0634] (4) Synthesis of Compound 66

[0635] Compound 66 according to the example can be synthesized by, for example, the following reaction.

[0636] (Synthesis of Intermediate 66-a)

[0637]

[0638] Under argon atmosphere, 1,3-dibromo-5-iodobenzene (3 equivalents), phenylboronic acid (1.0 equivalent), Pd(PPh 3 ) 4 (0.03 eq.) and potassium carbonate (2 eq.) and dissolved in THF:H 2 O (3:1), and the reaction solution was stirred at about 70° C. for about 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction, and the organic layer was collected and filtered through MgSO 4 The filtrate was dried and filtered. The solvent was removed under reduced pressure and the filtrate was purified by using CH 2 Cl 2 The solid thus obtained was purified and separated by column chromatography using 4,4-dihydro-1,4-bis(2-nitropropene) and hexane as a developing solvent, thereby obtaining Intermediate 66-a (yield: 60%). The compound thus obtained was identified as Intermediate 66-a by ESI-LCMS.

[0639] ESI-LCMS: [M] + :C 12 H 8 Br 2 , 310.8993.

[0640] (Synthesis of Intermediate 66-b)

[0641]

[0642] According to the same method for synthesizing Intermediate 2-a, Intermediate 66-b was synthesized using Intermediate 66-a instead of 1,3-dibromo-5-(tert-butyl)benzene (yield: 68%). The solid thus obtained was identified as Intermediate 66-b by ESI-LCMS.

[0643] ESI-LCMS: [M] + :C 34 H 30 BrN, 531.1562.

[0644] (Synthesis of Intermediate 66-c)

[0645]

[0646] According to the same method for synthesizing Intermediate 2-b, Intermediate 66-c was synthesized using Intermediate 66-b instead of Intermediate 2-a (yield: 67%). The solid thus obtained was identified as Intermediate 66-c by ESI-LCMS.

[0647] ESI-LCMS: [M] + :C 40 H 33 BrClN, 641.1485.

[0648] (Synthesis of Intermediate 66-d)

[0649]

[0650] According to the same method for synthesizing Intermediate 2-c, Intermediate 66-d was synthesized using Intermediate 66-c instead of Intermediate 2-b (yield: 75%). The solid thus obtained was identified as Intermediate 66-d by ESI-LCMS.

[0651] ESI-LCMS: [M] + :C 62 H 55 C1N 2 , 862.4054.

[0652] (Synthesis of Intermediate 66-e)

[0653]

[0654] According to the same method for synthesizing Intermediate 2-d, Intermediate 66-e was synthesized using Intermediate 66-d instead of Intermediate 2-c (yield: 63%). The solid thus obtained was identified as Intermediate 66-e by ESI-LCMS.

[0655] ESI-LCMS: [M] + :C 68 H 59 C1N 2 , 938.4367.

[0656] (Synthesis of Intermediate 66-f)

[0657]

[0658] According to the same method for synthesizing Intermediate 2-e, Intermediate 66-f (yellow solid, yield: 30%) was synthesized using Intermediate 66-e instead of Intermediate 2-d. The solid thus obtained was identified as Intermediate 66-f by ESI-LCMS.

[0659] ESI-LCMS: [M] + :C 68 H 56 BCN 2 , 946.4225.

[0660] (Synthesis of Intermediate 66-g)

[0661]

[0662] According to the same method for synthesizing Intermediate 2-f, Intermediate 66-g was synthesized using Intermediate 66-f instead of Intermediate 2-e (yield: 52%). The solid thus obtained was identified as Intermediate 66-g by ESI-LCMS.

[0663] ESI-LCMS: [M] + :C 68 H 55 BBrCl 2 , 1024.3330.

[0664] (Synthesis of Intermediate 66-h)

[0665]

[0666] According to the same method for synthesizing Intermediate 2-g, Intermediate 66-h was synthesized using Intermediate 66-g instead of Intermediate 2-f (yield: 66%). The solid thus obtained was identified as Intermediate 66-h by ESI-LCMS.

[0667] ESI-LCMS: [M] + :C 92 H 74 BCN 2 Si, 1280.5403.

[0668] (Synthesis of Compound 66)

[0669]

[0670] According to the same method used to synthesize compound 2, compound 66 (yellow solid, yield: 70%) was synthesized using intermediate 66-h instead of intermediate 2-g. 1 The yellow solid thus obtained was identified as Compound 66 by H-NMR and ESI-LCMS.

[0671] 1 H-NMR (400MHz, CDCl 3 ):d=9.10(d,1H),9.02(s,1H),7.87-7.83(m,4H),7.77-7.71(m,8H),7.68-7.62(m,5H),7.48 -7.38(m,15H),7.24-7.15(m,12H),7.11-7.01(m,8H),6.30-6.27(s,2H),1.40-1.38(s,18H).

[0672] ESI-LCMS: [M] + :C 104 H 74 D 8 BN 3 Si, 1419.6874.

[0673] (5) Synthesis of Compound 78

[0674] Compound 78 according to the example can be synthesized by, for example, the following reaction.

[0675] (Synthesis of Intermediate 78-a)

[0676]

[0677] According to the same method for synthesizing Intermediate 66-a, Intermediate 78-a was synthesized using (3,5-di-tert-butylphenyl)boronic acid instead of phenylboronic acid (yield: 62%). The solid thus obtained was identified as Intermediate 78-a by ESI-LCMS.

[0678] ESI-LCMS: [M] + :C 20 H 24 Br2 , 424.2200.

[0679] (Synthesis of Intermediate 78-b)

[0680]

[0681] According to the same method for synthesizing Intermediate 2-a, Intermediate 78-b was synthesized using Intermediate 78-a instead of 1,3-dibromo-5-(tert-butyl)benzene (yield: 70%). The solid thus obtained was identified as Intermediate 78-b by ESI-LCMS.

[0682] ESI-LCMS: [M] + :C 42 H 46 BrN, 643.2813.

[0683] (Synthesis of Intermediate 78-c)

[0684]

[0685] According to the same method for synthesizing Intermediate 2-b, Intermediate 78-c was synthesized using Intermediate 78-b instead of Intermediate 2-a (yield: 65%). The solid thus obtained was identified as Intermediate 78-c by ESI-LCMS.

[0686] ESI-LCMS: [M] + :C 48 H 49 BrClN, 754.2737.

[0687] (Synthesis of Intermediate 78-d)

[0688]

[0689] According to the same method for synthesizing Intermediate 2-c, Intermediate 78-d was synthesized using Intermediate 78-c instead of Intermediate 2-b (yield: 75%). The solid thus obtained was identified as Intermediate 78-d by ESI-LCMS.

[0690] ESI-LCMS: [M] + :C 70 H 71 C1N 2 , 974.5306.

[0691] (Synthesis of Intermediate 78-e)

[0692]

[0693] According to the same method for synthesizing Intermediate 2-d, Intermediate 78-e was synthesized using Intermediate 78-d instead of Intermediate 2-c (yield: 69%). The solid thus obtained was identified as Intermediate 78-e by ESI-LCMS.

[0694] ESI-LCMS: [M] + :C 76 H 75 C1N 2 , 1050.5619.

[0695] (Synthesis of Intermediate 78-f)

[0696]

[0697] According to the same method for synthesizing Intermediate 2-e, Intermediate 78-f was synthesized using Intermediate 78-e instead of Intermediate 2-d (yield: 34%). The solid thus obtained was identified as Intermediate 78-f by ESI-LCMS.

[0698] ESI-LCMS: [M] + :C 76 H 72 BCN 2 , 1058.5477.

[0699] (Synthesis of Intermediate 78-g)

[0700]

[0701] According to the same method for synthesizing Intermediate 2-f, Intermediate 78-g was synthesized using Intermediate 78-f instead of Intermediate 2-e (yield: 52%). The solid thus obtained was identified as Intermediate 78-g by ESI-LCMS.

[0702] ESI-LCMS: [M] + :C 76 H 71 BBrCl 2 , 1136.4582.

[0703] (Synthesis of Intermediate 78-h)

[0704]

[0705] According to the same method for synthesizing Intermediate 2-g, Intermediate 78-h was synthesized using Intermediate 78-g instead of Intermediate 2-f (yield: 69%). The solid thus obtained was identified as Intermediate 78-h by ESI-LCMS.

[0706] ESI-LCMS: [M] + :C 92 H 74 BCN 2 Si, 1280.5403.

[0707] (Synthesis of Compound 78)

[0708]

[0709] According to the same method used to synthesize compound 2, compound 78 was synthesized using intermediate 78-h instead of intermediate 2-g and 3,6-bis(methyl-D3)-9H-carbazole instead of 9H-carbazole-1,2,3,4,5,6,7,8-D8 (yield: 72%). 1 The yellow solid thus obtained was identified as Compound 78 by H-NMR and ESI-LCMS.

[0710] 1 H-NMR (400MHz, CDCl 3 ):d=9.05(d,1H),9.03(s,1H),8.53-8.32(m,6H),7.76-7.70(m,4H),7.65-7.59(m,8H),7.57-7.53(m,5H),7.50- 7.40(m,15H),7.23-7.16(m,10H),7.12-7.05(m,8H),6.45-6.43(s,2H),1.50-1.47(S,18H),1.40-1.38(s,18H).

[0711] ESI-LCMS: [M] + :C 114 H 96 D 6 BN 3 Si, 1557.8313.

[0712] (6) Synthesis of Compound 83

[0713] Compound 83 according to the example can be synthesized by, for example, the following reaction.

[0714] (Synthesis of Intermediate 83-a)

[0715]

[0716] According to the same method for synthesizing Intermediate 2-d, Intermediate 83-a was synthesized using Intermediate 3-a instead of Intermediate 2-c (yield: 68%). The solid thus obtained was identified as Intermediate 83-a by ESI-LCMS.

[0717] ESI-LCMS: [M] + :C 40 H 34 BrN, 607.1875.

[0718] (Synthesis of Intermediate 83-b)

[0719]

[0720] According to the same method for synthesizing intermediate 2-c, intermediate 83-a was used instead of intermediate 2-b and 5'-phenyl-[1,1':3',1"-terphenyl]-2'-amine was used instead of 5'-(tert-butyl)-[1,1':3',1"-terphenyl]-2'-amine to synthesize intermediate 83-b (yield: 75%). The solid thus obtained was identified as intermediate 83-b by ESI-LCMS.

[0721] ESI-LCMS: [M] + :C 64 H 52 N 2 , 848.4130.

[0722] (Synthesis of Intermediate 83-c)

[0723]

[0724] According to the same method for synthesizing Intermediate 2-d, Intermediate 83-c was synthesized using Intermediate 83-b instead of Intermediate 2-c and using 4-iodobiphenyl instead of iodobenzene (yield: 65%). The solid thus obtained was identified as Intermediate 83-c by ESI-LCMS.

[0725] ESI-LCMS: [M] + :C 76 H 60 N 2 , 1000.4756.

[0726] (Synthesis of Intermediate 83-d)

[0727]

[0728] According to the same method for synthesizing Intermediate 2-e, Intermediate 83-d (yellow solid, yield: 31%) was synthesized using Intermediate 83-c instead of Intermediate 2-d. The solid thus obtained was identified as Intermediate 83-d by ESI-LCMS.

[0729] ESI-LCMS: [M] + :C 76 H57 BN 2 , 1008.4615.

[0730] (Synthesis of Intermediate 83-e)

[0731]

[0732] According to the same method for synthesizing Intermediate 2-f, Intermediate 83-e was synthesized using Intermediate 83-d instead of Intermediate 2-e (yield: 51%). The solid thus obtained was identified as Intermediate 83-e by ESI-LCMS.

[0733] ESI-LCMS: [M] + :C 76 H 56 BnB 2 , 1086.3720.

[0734] (Synthesis of Compound 83)

[0735]

[0736] According to the same method used to synthesize Intermediate 2-g, Compound 83 was synthesized using Intermediate 83-e instead of Intermediate 2-f (yield: 65%). 1 The yellow solid thus obtained was identified as Compound 83 by H-NMR and ESI-LCMS.

[0737] 1 H-NMR (400MHz, CDCl 3 ):d=9.16(d,1H),9.14(s,1H),7.88-7.84(m,4H),7.80-7.75(m,6H),7.60-7.57(s,4H),7.50-7.40(m, 17H),7.27-7.15(m,12H),7.13-7.04(m,8H),7.03-6.89(m,11H),6.50-6.48(s,2H),1.35-1.32(s,9H).

[0738] ESI-LCMS: [M] + :C 100 H 75 BN 2 Si, 1342.5793.

[0739] (7) Synthesis of Compound 101

[0740] Compound 101 according to the example can be synthesized by, for example, the following reaction.

[0741] (Synthesis of Intermediate 101-a)

[0742]

[0743] According to the same method for synthesizing Intermediate 2-d, Intermediate 101-a was synthesized using 1-bromo-3-iodobenzene instead of iodobenzene (yield: 63%). The solid thus obtained was identified as Intermediate 101-a by ESI-LCMS.

[0744] ESI-LCMS: [M] + :C 66 H 66 BrClN 2 , 996.3785.

[0745] (Synthesis of Intermediate 101-b)

[0746]

[0747] According to the same method for synthesizing Intermediate 2-e, Intermediate 101-b (yellow solid, yield: 25%) was synthesized using Intermediate 101-a instead of Intermediate 2-d. The solid thus obtained was identified as Intermediate 101-b by ESI-LCMS.

[0748] ESI-LCMS: [M] + :C 66 H 59 BBrCl 2 , 1004.3643.

[0749] (Synthesis of Intermediate 101-c)

[0750]

[0751] According to the same method for synthesizing Intermediate 2-g, Intermediate 101-c was synthesized using Intermediate 101-b instead of Intermediate 2-f (yield: 68%). The solid thus obtained was identified as Intermediate 101-c by ESI-LCMS.

[0752] ESI-LCMS: [M] + :C 90 H 78 BCN 2 Si, 1260.5716.

[0753] (Synthesis of Compound 101)

[0754]

[0755] According to the same method used to synthesize Compound 2, Compound 101 (yellow solid, yield: 70%) was synthesized using Intermediate 101-c instead of Intermediate 2-g. 1 The yellow solid thus obtained was identified as Compound 101 by H-NMR and ESI-LCMS.

[0756] 1 H-NMR (400MHz, CDCl 3 ):d=9.18(d,1H),9.10(d,1H),7.90-7.86(m,4H),7.78-7.72(m,4H),7.58-7.51(s,4H),7.40-7.28(m, 15H),7.21-7.10(m,12H),7.08-6.98(m,8H),6.53-6.50(s,2H),1.41-1.39(s,18H),1.35-1.32(s,9H).

[0757] ESI-LCMS: [M] + :C 102 H 78 D 8 BN 3 Si, 1399.7186.

[0758] (8) Synthesis of Compound 107

[0759] Compound 107 according to the example can be synthesized by, for example, the following reaction.

[0760] (Synthesis of Intermediate 107-a)

[0761]

[0762] According to the same method for synthesizing Intermediate 2-g, Intermediate 107-a was synthesized using (3-(triphenylsilyl)phenyl)boronic acid instead of (4-(triphenylsilyl)phenyl)boronic acid (yield: 70%). The solid thus obtained was identified as Intermediate 107-a by ESI-LCMS.

[0763] ESI-LCMS: [M] + :C 90 H 78 BCN 2 Si, 1260.5716.

[0764] (Synthesis of Compound 107)

[0765]

[0766] According to the same method used to synthesize Compound 2, Compound 107 (yellow solid, yield: 68%) was synthesized using Intermediate 107-a instead of Intermediate 2-g. 1 The yellow solid thus obtained was identified as Compound 107 by H-NMR and ESI-LCMS.

[0767] 1 H-NMR (400MHz, CDCl 3 ):d=9.15(d,1H),9.12(s,1H),7.89-7.80(m,4H),7.75-7.65(m,4H),7.43-7.40(s,4H),7.38-7.28(m, 15H),7.20-7.12(m,12H),7.08-6.99(m,8H),6.20-6.18(s,2H),1.41-1.39(s,18H),1.35-1.32(s,9H).

[0768] ESI-LCMS: [M] + :C 102 H 78 D 8 BN 3 Si, 1399.7186.

[0769] (9) Synthesis of Compound 113

[0770] Compound 113 according to the example can be synthesized by, for example, the following reaction.

[0771] (Synthesis of Intermediate 113-a)

[0772]

[0773] Intermediate 113-a was synthesized according to the same method used for Intermediate 2-a, using 5-(tert-butyl)-[1,1'-biphenyl]-2-amine instead of 5'-(tert-butyl)-[1,1':3',1"-terphenyl]-2'-amine (yield: 54%). The solid thus obtained was identified as Intermediate 113-a by ESI-LCMS.

[0774] ESI-LCMS: [M] + :C 36 H 30 BrN, 435.1562.

[0775] (Synthesis of Intermediate 113-b)

[0776]

[0777] According to the same method for synthesizing Intermediate 2-b, Intermediate 113-b was synthesized using Intermediate 113-a instead of Intermediate 2-a (yield: 85%). The solid thus obtained was identified as Intermediate 113-b by ESI-LCMS.

[0778] ESI-LCMS: [M] + :C 32 H 33 BrClN, 545.1485.

[0779] (Synthesis of Intermediate 113-c)

[0780]

[0781] According to the same method for synthesizing Intermediate 2-c, Intermediate 113-c was synthesized using Intermediate 113-b instead of Intermediate 2-b (yield: 71%). The solid thus obtained was identified as Intermediate 113-c by ESI-LCMS.

[0782] ESI-LCMS: [M] + :C 54 H 55 C1N 2 , 766.4054.

[0783] (Synthesis of Intermediate 113-d)

[0784]

[0785] According to the same method for synthesizing Intermediate 2-d, Intermediate 113-d was synthesized using Intermediate 113-c instead of Intermediate 2-c (yield: 62%). The solid thus obtained was identified as Intermediate 113-d by ESI-LCMS.

[0786] ESI-LCMS: [M] + :C 60 H 59 C1N 2 , 842.4367.

[0787] (Synthesis of Intermediate 113-e)

[0788]

[0789] According to the same method for synthesizing Intermediate 2-e, Intermediate 113-e (yellow solid, yield: 26%) was synthesized using Intermediate 113-d instead of Intermediate 2-d. The solid thus obtained was identified as Intermediate 113-e by ESI-LCMS.

[0790] ESI-LCMS: [M] + :C 60 H 56 BCN 2 , 850.4225.

[0791] (Synthesis of Intermediate 113-f)

[0792]

[0793] According to the same method for synthesizing Intermediate 2-f, Intermediate 113-f was synthesized using Intermediate 113-e instead of Intermediate 2-e (yield: 53%). The solid thus obtained was identified as Intermediate 113-f by ESI-LCMS.

[0794] ESI-LCMS: [M] + :C 60 H 55 BClBrN 2 , 928.3330.

[0795] (Synthesis of Intermediate 113-g)

[0796]

[0797] According to the same method for synthesizing Intermediate 2-g, Intermediate 113-g was synthesized using Intermediate 113-f instead of Intermediate 2-f (yield: 64%). The solid thus obtained was identified as Intermediate 113-g by ESI-LCMS.

[0798] ESI-LCMS: [M] + :C 84 H 74 BCN 2 Si, 1184.5403.

[0799] (Synthesis of Compound 113)

[0800]

[0801] According to the same method used to synthesize Compound 2, Compound 113 (yellow solid, yield: 70%) was synthesized using Intermediate 113-g instead of Intermediate 2-g. 1 The yellow solid thus obtained was identified as Compound 113 by H-NMR and ESI-LCMS.

[0802] 1 H-NMR (400MHz, CDCl 3):d=9.15(d,1H),9.12(s,1H),7.89-7.80(m,4H),7.75-7.65(m,4H),7.43-7.40(s,4H),7.38-7.28(m, 15H),7.20-7.12(m,12H),7.08-6.99(m,8H),6.20-6.18(s,2H),1.41-1.39(s,18H),1.35-1.32(s,9H).

[0803] ESI-LCMS: [M] + :C 102 H 78 D 8 BN 3 Si, 1399.7186.

[0804] (10) Synthesis of Compound 117

[0805] Compound 117 according to the example can be synthesized by, for example, the following reaction.

[0806] (Synthesis of Intermediate 117-a)

[0807]

[0808] Under an argon atmosphere, in a 1L flask, the compound 2-bromodibenzo[b,d]furan (1 equivalent) was dissolved in THF (excess), the temperature was lowered to about -78°C, and 2.5M n-butyllithium (0.95 equivalent) was added dropwise thereto to produce Intermediate 1. In another flask, 1,4-dibromobenzene (1 equivalent) was dissolved in THF (excess), the temperature was lowered to about -78°C, 2.5M n-butyllithium (1 equivalent) was added dropwise thereto, and then stirred for about 3 hours, and dichlorodiphenylsilane (1 equivalent) was added thereto. The intermediate 1 synthesized above was added thereto, the temperature was slowly raised to room temperature, and the mixture was stirred for about 10 hours. After the reaction was completed, water and ethyl acetate were added, extraction was performed, and the organic layer was collected and filtered through MgSO 4 The filtrate was dried and filtered. The solvent was removed under reduced pressure and the filtrate was purified by using CH 2 Cl 2 The solid thus obtained was purified and separated by column chromatography using 4% paraformaldehyde and hexane as a developing solvent, thereby obtaining Intermediate 117-a (yield: 38%). The compound thus obtained was identified as Intermediate 117-a by ESI-LCMS.

[0809] ESI-LCMS: [M] + :C 30 H 21 BrOSi, 504.0545.

[0810] (Synthesis of Intermediate 117-b)

[0811]

[0812] Under an argon atmosphere, intermediate 117-a (1 equivalent), bis(pinacolato) diboron (1.2 equivalents), bis(triphenylphosphine) palladium(II) dichloride (0.03 g) and potassium carbonate (2 equivalents) were added to a 2L flask and dissolved in 1,4-dioxane, and the reaction solution was stirred at about 120° C. for about 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added, extraction was performed, and the organic layer was collected and filtered through MgSO 4 The filtrate was dried and filtered. The solvent was removed under reduced pressure and the filtrate was purified by using CH 2 Cl 2 The solid thus obtained was purified and separated by column chromatography using 4% paraformaldehyde and hexane as a developing solvent, thereby obtaining Intermediate 117-b (yield: 70%). The compound thus obtained was identified as Intermediate 117-b by ESI-LCMS.

[0813] ESI-LCMS: [M] + :C 36 H 33 BO 3 Si, 552.2292.

[0814] (Synthesis of Intermediate 117-c)

[0815]

[0816] According to the same method for synthesizing Intermediate 2-g, Intermediate 117-c was synthesized using Intermediate 117-b instead of (4-(triphenylsilyl)phenyl)boronic acid (yield: 68%). The solid thus obtained was identified as Intermediate 117-c by ESI-LCMS.

[0817] ESI-LCMS: [M] + :C 96 H 80 BCN 2 OSi, 1350.5821.

[0818] (Synthesis of Compound 117)

[0819]

[0820] According to the same method used to synthesize Compound 2, Compound 117 (yellow solid, yield: 71%) was synthesized using Intermediate 117-c instead of Intermediate 2-g.1 The yellow solid thus obtained was identified as Compound 117 by H-NMR and ESI-LCMS.

[0821] 1 H-NMR (400MHz, CDCl 3 ):d=9.11(d,1H),9.09(s,1H),7.90-7.80(m,8H),7.75-7.64(m,4H),7.55-7.52(s,4H),7.42-7.25(m, 15H),7.20-7.12(m,10H),7.08-6.99(m,8H),6.60-6.57(s,2H),1.41-1.39(s,18H),1.35-1.32(s,9H).

[0822] ESI-LCMS: [M] + :C 108 H 80 D 8 BN 3 OSi, 1489.7292.

[0823] 2. Fabrication and evaluation of light-emitting elements

[0824] The light-emitting element according to the embodiment including the fused polycyclic compound according to the embodiment in the emission layer is manufactured by the following method. The light-emitting elements of Examples 1 to 10 are manufactured using Compound 2, Compound 3, Compound 34, Compound 66, Compound 78, Compound 83, Compound 101, Compound 107, Compound 113 and Compound 117 as dopant materials for the emission layer, respectively. Comparative Examples 1 to 5 correspond to light-emitting elements manufactured using Comparative Compounds C1 to C5 as dopant materials for the emission layer.

[0825] [Example Compounds]

[0826]

[0827]

[0828] [Comparative Compounds]

[0829]

[0830] (Manufacturing of light-emitting elements)

[0831] In order to manufacture the light emitting elements of the examples and comparative examples, a layer of about 15 Ω / cm 2A glass substrate of an ITO electrode (product of Corning Co.) was cut into a size of approximately 50 mm×50 mm×0.7 mm, cleaned using isopropyl alcohol and pure water with ultrasound for approximately 5 minutes each, exposed to ultraviolet rays for approximately 30 minutes, cleaned by exposure to ozone to form an anode, and the anode was mounted in a vacuum evaporation device.

[0832] On the anode, NPD is deposited to form a On the hole injection layer, compound H-1-1 is deposited to form a hole injection layer having a thickness of about On the hole transport layer, CzSi is deposited to form a hole transport layer having a thickness of about The thickness of the electron blocking layer is .

[0833] A mixed body obtained by mixing the second compound according to the embodiment and the third compound in a ratio of about 1:1, the fourth compound, and the example compound or the comparative compound are formed by co-depositing in a weight ratio of about 85:14:1 On the emission layer, compound ETH2 from compound group 3 is deposited to form an emission layer having a thickness of about On the hole blocking layer, a carbon nanotube having a thickness of about 1000 nm was formed by co-depositing CNNPTRZ:Liq at a weight ratio of about 4.0:6.0. On the electron transport layer, Yb is deposited to form an electron transport layer having a thickness of about On the electron injection layer, Mg is deposited to form an electron injection layer having a thickness of about A cathode with a thickness of , thereby manufacturing a light-emitting element.

[0834] All layers were formed by a vacuum deposition method. Compound HT35 from compound group 2 was used as the second compound, compound ETH66 from compound group 3 was used as the third compound, and compound AD-38 from compound group 4 was used as the fourth compound.

[0835] Compounds used for manufacturing light-emitting elements of Examples and Comparative Examples are shown below. The following materials were used after purchasing commercial products and performing sublimation purification.

[0836]

[0837]

[0838] (Evaluation of properties of light-emitting element)

[0839] The element efficiency and element life of the light-emitting elements manufactured by using Compound 2, Compound 3, Compound 34, Compound 66, Compound 78, Compound 83, Compound 101, Compound 107, Compound 113 and Compound 117 and Comparative Compounds C1 to C5 are evaluated. In Table 1, the evaluation results of the light-emitting elements of Examples 1 to 10 and Comparative Examples 1 to 5 are shown. In the evaluation results of the properties of the examples and comparative examples shown in Table 1, 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 10 and Comparative Examples 1 to 5, Keithley MU 236 and a luminance meter PR650 were used to measure the brightness at about 1000 cd / m 2 The driving voltage (V), emission efficiency (cd / A) and emission wavelength (nm) at a current density of . The time consumed to reach about 95% brightness compared to the initial brightness was measured as the lifetime (T95), and the relative lifetime was calculated based on the light-emitting element of Comparative Example 1, and the results are shown in Table 1.

[0840] [Table 1]

[0841]

[0842]

[0843] Referring to Table 1, it can be confirmed that the light emitting element of the example using the condensed polycyclic compound according to the embodiment as the light emitting material shows improved emission efficiency and lifetime characteristics compared with the comparative example.

[0844] The exemplary fused polycyclic compounds each include a structure in which a phenyl group is connected to a fused ring core, and can exhibit improved thermally activated delayed fluorescence properties. In the fused polycyclic compound, a local excited triplet energy level ( 3 LE) can be used as a medium to increase the reverse intersystem crossing rate between the excited triplet energy level and the singlet excited energy level. Reverse intersystem crossing (RISC) occurs through the local excited triplet energy level ( 3 LE) mediated, the exciton energy can be transferred through T1→ 3The path of LE→S1 moves quickly, and accordingly, the reverse intersystem crossing (RISC) rate can be increased to improve the emission efficiency. The fused polycyclic compound according to the embodiment includes a silyl group having a large volume as a substituent, thereby increasing the intermolecular distance, thereby preventing Dexter energy transfer, and thus, improving the element performance. In addition, because the fused polycyclic compound according to the embodiment includes the first substituent and the second substituent as described above, the boron atom can be effectively protected, the intermolecular interaction can be suppressed, and the formation of quasi-molecules or excited complexes can be controlled, thereby improving the emission efficiency. Because the light-emitting element according to the embodiment includes the fused polycyclic compound according to the embodiment as a light-emitting dopant of a thermally activated delayed fluorescence (TADF) light-emitting element, high element efficiency and improved life characteristics can be achieved in the blue wavelength region.

[0845] Compared with the examples, Comparative Example 1 shows the results of deteriorated element life and efficiency. Comparative Compound C1 included in Comparative Example 1 includes a fused polycyclic heterocycle having one boron atom and two nitrogen atoms at the center, but does not include an aromatic group connected to the fused polycyclic heterocycle. Therefore, it is difficult to expect that the condensed polycyclic heterocycle can be obtained by locally exciting the triplet energy level ( 3 Compared with the exemplary compounds, the comparative compound C1 does not include a silyl group and the first and second substituents described above, and the protective effect of the boron atom may be deteriorated, and intermolecular interactions may not be sufficiently prevented.

[0846] Compared with the example, Comparative Example 2 and Comparative Example 5 each showed results of degraded element life and efficiency. Comparative Compound C2 and Comparative Compound C5 included in Comparative Example 2 and Comparative Example 5 each include a phenyl group connected to a fused polycyclic heterocyclic ring, but do not include a silyl group and a second substituent as described above. Therefore, compared with the example compound, the boron atom may not be sufficiently protected, and Dexter energy transfer may not be sufficiently controlled.

[0847] Compared with the examples, the comparative example 3 showed the results of deteriorated element life and efficiency. Compared with the example compounds, the comparative compound C3 included in the comparative example 3 is different from the example compounds in that a carbazole group, not a phenyl group, is connected to the condensed ring core. Therefore, it is difficult to expect that the comparative compound C3 shows an increase effect of the reverse intersystem crossing rate compared with the examples.

[0848] When Comparative Example 4 is compared with Example 1, it can be confirmed that Comparative Example 4 shows degraded element life and efficiency compared with Example 1. Comparative Compound C4 included in Comparative Example 4 is different from Compound 2 included in Example 1 in having a structure in which a methyl group is substituted at the ortho position of the phenyl group relative to the nitrogen atom of the condensed ring core instead of a phenyl group. In terms of thermal stability, a methyl group is a very weak substituent, and if a methyl group is introduced as a substituent instead of a phenyl group, it is very poor in terms of material stability, and the steric hindrance effect may be insufficient compared with a phenyl group, and it will be weak in terms of protection of a boron atom and control of Dexter energy transfer.

[0849] The fused polycyclic compound according to the embodiment can be used in the emission layer, and can help improve efficiency and lifespan. The fused polycyclic compound according to the embodiment includes a fused ring core having a boron atom and a first nitrogen atom and a second nitrogen atom, and includes an aromatic group connected at a specific position of the fused ring core, and thus can show improved thermally activated delayed fluorescence properties. The fused polycyclic compound according to the embodiment includes a silyl group connected to the aromatic group and a first substituent and a second substituent connected to the first nitrogen atom and the second nitrogen atom, respectively, and can have excellent optical properties and high material stability. Therefore, if the fused polycyclic compound according to the embodiment is introduced into the emission layer of the light-emitting element, high emission efficiency and long life can be achieved.

[0850] The light emitting element according to the embodiment may show improved element properties of high efficiency and long life.

[0851] The condensed polycyclic compound according to the embodiment may be included in an emission layer of a light emitting element and may contribute to improving efficiency and lifetime of the light emitting element.

[0852] The display device according to the embodiment can show excellent display quality.

[0853] 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 conjunction with an embodiment may be used alone or in combination with features, characteristics, and / or elements described in conjunction with other embodiments, unless otherwise specifically stated. Therefore, one of ordinary skill in the art will understand that various changes in form and detail may be made without departing from the spirit and scope of the present 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 Among them, in formula 1, A1 to A5, R a and R1 to R7 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 of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring 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, or are combined with adjacent groups to form a ring, n1 is an integer from 0 to 3, At least one of A1 to A5 is each independently a group represented by Formula 2, One of Ar1 and Ar2 is a group represented by Formula 3-1, and The other one of Ar1 and Ar2 is a group represented by Formula 3-2: Formula 2 Among them, in formula 2, Ar a To Ar c are each independently 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 - * is the position connected to formula 1; Formula 3-1 Formula 3-2 Among them, in formula 3-1 and formula 3-2, R8 to R 14 and Z1 to Z3 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 of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring 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, or are combined with adjacent groups to form a ring, a1 to a3 are each independently an integer from 0 to 5, and -* is the position connected to formula 1.

2. 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, Ar1, Ar2, R1 to R7, R a , A1 to A5 and n1 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 5: Formula 5 Among them, in formula 5, Ar1, Ar2, R1 to R7, R a ,n1,A1,A2,A4,A5,Ar a ,Ar b and Ar c Same as defined in Equation 1 and Equation 2.

4. The fused polycyclic compound according to claim 1, wherein The fused polycyclic compound is represented by one of Formula 6-1 to Formula 6-3: Formula 6-1 Formula 6-2 Formula 6-3 Among them, in Formula 6-1 to Formula 6-3, Z4 is 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 of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring 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, or is combined with an adjacent group to form a ring, a4 is an integer from 0 to 5, and R1 to R 14 , R a , A1 to A5, Z1 to Z3, n1 and a1 to a3 are the same as those defined in Formula 1, Formula 3-1 and Formula 3-2.

5. 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 b1 To R b3 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro 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 cycloalkyl group having 3 to 20 ring 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, or combines with adjacent groups to form a ring, m1 to m3 are each independently an integer from 0 to 5, Z4 is 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 of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring 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, or is combined with an adjacent group to form a ring, a4 is an integer from 0 to 5, and R1 to R 13 , R a , A1, A2, A4, A5, Z1 to Z3, n1 and a1 to a3 are the same as those defined in Formula 1, Formula 3-1 and Formula 3-2.

6. The fused polycyclic compound according to claim 1, wherein R6 is 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 R5 and R7 are each independently a hydrogen atom or a deuterium atom.

7. The fused polycyclic compound according to claim 1, wherein The fused polycyclic compound is represented by Formula 8-1 or Formula 8-2: Formula 8-1 Formula 8-2 Among them, in formula 8-1 and formula 8-2, R b4 is 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 cycloalkyl group having 3 to 20 ring 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, m4 is an integer from 0 to 5, Z4 is 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 of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring 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, or is combined with an adjacent group to form a ring, a4 is an integer from 0 to 5, and R1 to R5, R7 to R 13 , R a , A1 to A5, Z1 to Z3, n1 and a1 to a3 are the same as those defined in Formula 1, Formula 3-1 and Formula 3-2.

8. The fused polycyclic compound according to claim 1, wherein The fused polycyclic compound is represented by Formula 9-1 or Formula 9-2: Formula 9-1 Formula 9-2 Among them, in formula 9-1 and formula 9-2, Ar1, Ar2, R1 to R7, A1 to A5, R a and n1 are the same as those defined in Equation 1, and R 2a and R 3a Each is independently a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, or a group represented by Formula A-1 or Formula A-2: Formula A-1 Formula A-2 Among them, in formula A-1 and formula A-2, R c1 To R c3 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 oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amine 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, or combines with adjacent groups to form a ring, m11 is an integer from 0 to 5, and m12 and m13 are each independently an integer of 0 to 4.

9. The fused polycyclic compound according to claim 1, wherein In Formula 1, Ar1 and Ar2 are each independently a group selected from Substituent Group 1: Substituent Group 1 10. The fused polycyclic compound according to claim 1, wherein The fused polycyclic compound represented by Formula 1 is selected from Compound Group 1: Compound Group 1 11. A light emitting element, wherein: The light emitting element comprises: a first electrode; a second electrode disposed on the first electrode; and 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 10 as a first compound.

12. The light emitting element according to claim 11, 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 each independently N or C (R 51 ), L1 is a directly linked, 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 For direct connection, 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, or 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 remaining groups in are each independently C(R 56 ), R 56 is 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, 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 directly linked, 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; Formula D-1 Wherein, in formula D-1, Q1 to Q4 are each 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 Each is independently connected to the direct connection, *-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 are each independently 0 or 1, R 61 To R 66 each independently represents 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 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 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, and d1 to d4 are each independently an integer of 0 to 4.

13. A display device, wherein: The display device comprises: A circuit layer is disposed on the substrate layer; and The display element layer is disposed on the circuit layer and includes a light emitting element, wherein: The light emitting element comprises: a first electrode; a second electrode disposed on the first electrode; and 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 10 as a first compound.

14. The display device according to claim 13, wherein: The light emitting element comprises a plurality of emission layers, and At least one of the plurality of emission layers includes the first compound.

15. The display device according to claim 13, wherein: The display device further comprises: a light control layer, which is disposed on the display element layer and comprises quantum dots, wherein: The light emitting element emits light of a first color, and The light control layer comprises: a first light control portion including a first quantum dot that converts the first color light into a second color light in a wavelength region longer than that of the first color light; a second light control portion including a second quantum dot that converts the first color light into a third color light in a wavelength region longer than those of the first color light and the second color light; and The third light control part transmits the first color light.

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

Images