Heterocyclic Compound and Organic Light-Emitting Device Comprising the Same

Abstract

The present application relates to an organic light-emitting device, which includes a heterocyclic compound represented by Formula 1 #imgabs0# In Formula 1, X is O or S, one of R1 to R8 is a group represented by Formula 2-1, and one of the remaining groups is a group represented by Formula 2-2, where when X is O, one of R1, R2, R4, R5, R7, and R8 is a group represented by Formula 2-1.

Description

[0001] Cross - reference to related applications

[0002] This application claims the priority and benefit of Korean Patent Application No. 10 - 2019 - 0113526, filed with the Korean Intellectual Property Office on September 16, 2019, the entire content of which is incorporated herein by reference. Technical field

[0003] One or more aspects of embodiments of the present disclosure relate to heterocyclic compounds and organic light - emitting devices including the heterocyclic compounds. Background art

[0004] An organic light - emitting device is a self - emitting device that produces full - color images and may also have a wide viewing angle, high contrast, short response time, and excellent characteristics in terms of brightness, driving voltage, and / or response speed.

[0005] Examples of organic light - emitting devices may include a first electrode disposed on a substrate, and a hole - transport region, an emission layer, an electron - transport region, and a second electrode sequentially disposed on the first electrode. Holes provided by the first electrode may move to the emission layer through the hole - transport region, and electrons provided by the second electrode may move to the emission layer through the electron - transport region. Charge carriers (e.g., holes and electrons) recombine in the emission layer to generate excitons. These excitons may transition from an excited state to a ground state, thereby generating light. Summary of the invention

[0006] One or more aspects of embodiments of the present disclosure relate to novel heterocyclic compounds and organic light - emitting devices including the heterocyclic compounds.

[0007] Other aspects will be set forth in part in the following description, and in part will be obvious from the description, or may be learned by practice of the presented embodiments of the present disclosure.

[0008] One or more exemplary embodiments of the present disclosure provide a heterocyclic compound represented by Formula 1:

[0009] Formula 1

[0010]

[0011]

[0012] In Formula 1, Formula 2 - 1, and Formula 2 - 2,

[0013] X is O or S,

[0014] Each of R1 to R8 is independently selected from the group represented by Formula 2-1, the group represented by Formula 2-2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2),

[0015] One selected from R1 to R8 is a group represented by Formula 2-1, and one selected from the remaining groups is a group represented by Formula 2-2, wherein when X is O, one selected from R1, R2, R4, R5, R7 and R8 is a group represented by Formula 2-1,

[0016] R 11 to R 18 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10Cycloalkenyl group, substituted or unsubstituted C1-C 10 Heterocycloalkenyl group, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio group, substituted or unsubstituted C1-C 60 Heteroaryl group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2),

[0017] Two adjacent groups among R1 to R8 and two adjacent groups among R 11 to R 18 are optionally connected to each other to form a ring,

[0018] Ar1 to Ar3 are each independently a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group,

[0019] Ar2 and Ar3 are optionally connected to each other via a single bond, -C(Q4)(Q5)-, -Si(Q4)(Q5)-, -O-, -S-, -N(Q4)-, -B(Q4)-, -C(=O)-, -S(=O)2-, -S(=O)(Q4)(Q5)- or -P(=O)(Q4)- to form a fused heterocycle,

[0020] L 11 to L 13 are each independently a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group,

[0021] a11 to a13 are each independently an integer from 0 to 3,

[0022] When a11 is 0, *-(L 11 ) a11 -*' represents a single bond. When a12 is 0, *-(L 12 ) a12 -*' represents a single bond. And when a13 is 0, *-(L 13 ) a13 -*' represents a single bond.

[0023] The substituted C5-C 60Carbocyclic group, the substituted C1-C 60 Heterocyclic group, the substituted C1-C 60 Alkyl group, the substituted C2-C 60 Alkenyl group, the substituted C2-C 60 Alkynyl group, the substituted C1-C 60 Alkoxy group, the substituted C3-C 10 Cycloalkyl group, the substituted C1-C 10 Heterocycloalkyl group, the substituted C3-C 10 Cycloalkenyl group, the substituted C1-C 10 Heterocycloalkenyl group, the substituted C6-C 60 Aryl group, the substituted C6-C 60 Aryloxy group, the substituted C6-C 60 Arylthio group, the substituted C1-C 60 Heteroaryl group, at least one substituent of the substituted monovalent non-aromatic fused polycyclic group and the substituted monovalent non-aromatic fused heteropolycyclic group is selected from:

[0024] Deuterium, -F, -Cl, -Br, -I, hydroxy group, cyano group, nitro group, amidino group, hydrazino group, hydrazone group, C1-C 60 Alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group and C1-C 60 Alkoxy group;

[0025] Each is independently selected from deuterium, -F, -Cl, -Br, -I, hydroxy group, cyano group, nitro group, amidino group, hydrazino group, hydrazone group, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q11 ), -S(=O)2(Q 11 ), and -P(=O)(Q 11 )(Q 12 ), where at least one of the substituents is a C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, and C1-C 60 alkoxy group;

[0026] C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C1-C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, biphenyl group, and terphenyl group;

[0027] Each is independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazone group, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C1-C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, biphenyl group, terphenyl group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ), and -P(=O)(Q21 )(Q 22 ) in at least one substituted C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C1-C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, biphenyl group and terphenyl group; and

[0028] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ),

[0029] Q1 to Q5, Q 11 to Q 13 、Q 21 to Q 23 and Q 31 to Q 33 each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy group, cyano group, nitro group, amidino group, hydrazino group, hydrazone group, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C6-C 60 aryl group substituted with a C1-C 60 alkyl group, C1-C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, biphenyl group and terphenyl group, and

[0030] * represents a bonding site to the group represented by Formula 1, and *' represents a bonding site to an adjacent atom.

[0031] One or more exemplary embodiments of the present disclosure provide an organic light-emitting device including: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the organic layer contains at least one heterocyclic compound represented by Formula 1. BRIEF DESCRIPTION OF THE DRAWINGS

[0032] The above and other aspects, features, and advantages of certain embodiments of the present disclosure will become more apparent from the following description in conjunction with the accompanying drawings, in which:

[0033] Figures 1 to 4 Each is a schematic diagram of the structure of an organic light-emitting device according to an embodiment. DETAILED DESCRIPTION

[0034] The present disclosure will now be described more fully with reference to the accompanying drawings, in which exemplary embodiments of the present disclosure are shown. The same reference numerals throughout the drawings denote the same elements, and redundant descriptions thereof may be omitted. The terms used herein are for the purpose of describing particular exemplary embodiments only and are not intended to limit the exemplary embodiments described herein.

[0035] As used herein, the singular forms "a", "an", and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. It should also be understood that the terms "includes", "including", "comprises", and / or "comprising", when used in this specification, specify the presence of the stated features, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more other features, steps, operations, elements, components, and / or groups thereof.

[0036] As used herein, expressions such as "at least one of", "one of", and "selected from" when preceding a list of elements modify the entire list of elements and not a single element of the list. As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. Further, the use of "may" when describing embodiments of the present disclosure refers to "one or more embodiments of the present disclosure".

[0037] One or more exemplary embodiments of the present disclosure provide a heterocyclic compound represented by Formula 1:

[0038] Formula 1

[0039]

[0040]

[0041] In Formula 1, Formula 2-1 and Formula 2-2, X, R1 to R8, R 11 to R 18 , L 11 to L 13 , a11 to a13 and Ar1 to Ar3 will be described in more detail.

[0042] X in Formula 1 can be O or S.

[0043] R1 to R8 in Formula 1 can each independently be selected from the group represented by Formula 2-1, the group represented by Formula 2-2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2), and

[0044] One selected from R1 to R8 can be the group represented by Formula 2-1, and one selected from the remaining groups can be the group represented by Formula 2-2, wherein when X is O, one selected from R1, R2, R4, R5, R7 and R8 can be the group represented by Formula 2-1.

[0045] In one embodiment, in Formula 1, X can be O, one of R1, R2, and R4 can be a group represented by Formula 2-1, and one of R5 to R8 can be a group represented by Formula 2-2.

[0046] For example, in Formula 1, when X is O, R1 can be a group represented by Formula 2-1, and R5 can be a group represented by Formula 2-2; R1 can be a group represented by Formula 2-1, and R6 can be a group represented by Formula 2-2; R1 can be a group represented by Formula 2-1, and R7 can be a group represented by Formula 2-2; R1 can be a group represented by Formula 2-1, and R8 can be a group represented by Formula 2-2; R2 can be a group represented by Formula 2-1, and R5 can be a group represented by Formula 2-2; R2 can be a group represented by Formula 2-1, and R6 can be a group represented by Formula 2-2; R2 can be a group represented by Formula 2-1, and R7 can be a group represented by Formula 2-2; R2 can be a group represented by Formula 2-1, and R8 can be a group represented by Formula 2-2; R4 can be a group represented by Formula 2-1, and R5 can be a group represented by Formula 2-2; R4 can be a group represented by Formula 2-1, and R6 can be a group represented by Formula 2-2; R4 can be a group represented by Formula 2-1, and R7 can be a group represented by Formula 2-2; or R4 can be a group represented by Formula 2-1, and R8 can be a group represented by Formula 2-2.

[0047] In one or more embodiments, in Formula 1, X can be S, one of R1 to R4 can be a group represented by Formula 2-1, and one of R5 to R8 can be a group represented by Formula 2-2.

[0048] For example, in Formula 1, when X is S, R1 can be a group represented by Formula 2-1, and R5 can be a group represented by Formula 2-2; R1 can be a group represented by Formula 2-1, and R6 can be a group represented by Formula 2-2; R1 can be a group represented by Formula 2-1, and R7 can be a group represented by Formula 2-2; R1 can be a group represented by Formula 2-1, and R8 can be a group represented by Formula 2-2; R2 can be a group represented by Formula 2-1, and R5 can be a group represented by Formula 2-2; R2 can be a group represented by Formula 2-1, and R6 can be a group represented by Formula 2-2; R2 can be a group represented by Formula 2-1, and R7 can be a group represented by Formula 2-2; R2 can be a group represented by Formula 2-1, and R8 can be a group represented by Formula 2-2; R3 can be a group represented by Formula 2-1, and R5 can be a group represented by Formula 2-2; R3 can be a group represented by Formula 2-1, and R6 can be a group represented by Formula 2-2; R3 can be a group represented by Formula 2-1, and R7 can be a group represented by Formula 2-2; R3 can be a group represented by Formula 2-1, and R8 can be a group represented by Formula 2-2; R4 can be a group represented by Formula 2-1, and R5 can be a group represented by Formula 2-2; R4 can be a group represented by Formula 2-1, and R6 can be a group represented by Formula 2-2; R4 can be a group represented by Formula 2-1, and R7 can be a group represented by Formula 2-2; or R4 can be a group represented by Formula 2-1, and R8 can be a group represented by Formula 2-2.

[0049] In one or more embodiments, in Formula 1, X can be O, one of R1, R2, and R4 can be a group represented by Formula 2-1, and one of R1 to R4 that is not a group represented by Formula 2-1 can be a group represented by Formula 2-2.

[0050] For example, in Formula 1, when X is O, R1 can be a group represented by Formula 2-1, and R2 can be a group represented by Formula 2-2; R1 can be a group represented by Formula 2-1, and R3 can be a group represented by Formula 2-2; R1 can be a group represented by Formula 2-1, and R4 can be a group represented by Formula 2-2; R2 can be a group represented by Formula 2-1, and R1 can be a group represented by Formula 2-2; R2 can be a group represented by Formula 2-1, and R3 can be a group represented by Formula 2-2; R2 can be a group represented by Formula 2-1, and R4 can be a group represented by Formula 2-2; R4 can be a group represented by Formula 2-1, and R1 can be a group represented by Formula 2-2; R4 can be a group represented by Formula 2-1, and R2 can be a group represented by Formula 2-2; or R4 can be a group represented by Formula 2-1, and R3 can be a group represented by Formula 2-2.

[0051] In one or more embodiments, in Formula 1, X can be S, one selected from R1 to R4 can be a group represented by Formula 2-1, and one selected from the remaining groups can be a group represented by Formula 2-2.

[0052] For example, in Formula 1, when X is S, R1 can be a group represented by Formula 2-1, and R2 can be a group represented by Formula 2-2; R1 can be a group represented by Formula 2-1, and R3 can be a group represented by Formula 2-2; R1 can be a group represented by Formula 2-1, and R4 can be a group represented by Formula 2-2; R2 can be a group represented by Formula 2-1, and R1 can be a group represented by Formula 2-2; R2 can be a group represented by Formula 2-1, and R3 can be a group represented by Formula 2-2; R2 can be a group represented by Formula 2-1, and R4 can be a group represented by Formula 2-2; R3 can be a group represented by Formula 2-1, and R1 can be a group represented by Formula 2-2; R3 can be a group represented by Formula 2-1, and R2 can be a group represented by Formula 2-2; R3 can be a group represented by Formula 2-1, and R4 can be a group represented by Formula 2-2; R4 can be a group represented by Formula 2-1, and R1 can be a group represented by Formula 2-2; R4 can be a group represented by Formula 2-1, and R2 can be a group represented by Formula 2-2; or R4 can be a group represented by Formula 2-1, and R3 can be a group represented by Formula 2-2.

[0053] In one embodiment, R1 to R8 in Formula 1 can each independently be selected from:

[0054] The group represented by Formula 2-1, the group represented by Formula 2-2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazone group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, a n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, a n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, a n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, a n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group; and

[0055] a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, a n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, a n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, a n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, a n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, and -I, but the embodiments of the present disclosure are not limited thereto.

[0056] In some embodiments, among R1 to R8, the groups not represented by Formula 2-1 or Formula 2-2 may each be hydrogen.

[0057] R in Formula 2-1 11 to R 18 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazone group, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10Heterocyclic alkenyl group, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio group, substituted or unsubstituted C1-C 60 Heteroaryl group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2).

[0058] In one embodiment, R 11 to R 18 can each independently be selected from:

[0059] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec-decyl group and tert-decyl group; and

[0060] Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec-decyl group and tert-decyl group each substituted with at least one selected from deuterium, -F, -Cl, -Br and -I, but the embodiments of the present disclosure are not limited thereto.

[0061] For example, R 11 to R 18 can each independently be selected from:

[0062] Hydrogen, deuterium, -F, -Cl, -Br, -I, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec-decyl group and tert-decyl group; and

[0063] Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec-decyl group and tert-decyl group, each substituted with at least one selected from deuterium, -F, -Cl, -Br and -I.

[0064] In some embodiments, for example, R 11 to R 18 can each independently be selected from:

[0065] Hydrogen, deuterium, -F, -Cl, -Br, -I, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, isohexyl group, sec-hexyl group and tert-hexyl group; and

[0066] Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, isohexyl group, sec-hexyl group and tert-hexyl group, each substituted with at least one selected from deuterium, -F, -Cl, -Br and -I.

[0067] In Formula 1 and Formula 2-1, two adjacent groups among R1 to R8 and R 11 to R 18Two adjacent groups in can optionally be connected to each other to form a ring.

[0068] In one embodiment, two adjacent groups among R1 to R8 and R 11 to R 18 Two adjacent groups in can optionally be connected to each other to form a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group.

[0069] L in Formula 2-2 11 to L 13 can each independently be a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group.

[0070] In one embodiment, L 11 to L 13 can each independently be selected from:

[0071] benzene group, pentacene group, indene group, naphthalene group, azulene group, heptacene group, indacene group, acenaphthylene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, pyrene group, group, tetracene group, picene group, perylene group, pyrrole group, thiophene group, furan group, silole group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, triazine group, benzofuran group, benzothiophene group, dibenzofuran group, dibenzothiophene group, carbazole group, benzosilole group, dibenzosilole group, quinoline group, isoquinoline group, benzimidazole group, imidazopyridine group and imidazopyrimidine group;

[0072] each being independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, C1-C 20 alkyl group, C1-C 20 alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, pentacenyl group, indenyl group, naphthyl group, azulenyl group, heptacenyl group, indacenyl group, acenaphthylenyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, pyrenyl group, A base group, a tetracenyl group, a picene group, a perylene group, a pyrrolyl group, a thienyl group, a furyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, a benzosilolyl group, a dibenzosilolyl group, a quinolinyl group, an isoquinolinyl group, a benzimidazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), and -P(=O)(Q 31 )(Q 32 ) in which at least one is substituted, a pentalene group, an indene group, a naphthalene group, a azulene group, a heptalene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a pyrene group, a group, a tetracene group, a picene group, a perylene group, a pyrrole group, a thiophene group, a furan group, a silole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a triazine group, a benzofuran group, a benzothiophene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a benzosilole group, a dibenzosilole group, a quinoline group, an isoquinoline group, a benzimidazole group, an imidazopyridinyl group, and an imidazopyrimidinyl group,

[0073] However, the embodiments of the present disclosure are not limited thereto, and

[0074] Q 31 to Q 33 can each independently be selected from a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, and a pyridyl group.

[0075] For example, L 11 to L 13 can each independently be a group represented by one selected from Formulas 3-1 to 3-39:

[0076]

[0077]

[0078]

[0079] In Formulas 3-1 to 3-39,

[0080] Y1 can be O, S, C(Z3)(Z4), N(Z3), or Si(Z3)(Z4),

[0081] Z1 to Z4 can each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorene group, a spiro-bifluorene group, a benzo[fluorene group, a dibenzo[fluorene group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a pyrenyl group, a [group name], a tetracenyl group, a pyrrolyl group, a thiophenyl group, a furyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a benzofuryl group, a benzothiophenyl group, a dibenzofuryl group, a dibenzothiophenyl group, a carbazolyl group, a benzosilolyl group, a dibenzosilolyl group, a quinolinyl group, an isoquinolinyl group, a benzimidazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and -Si(Q 31 )(Q 32 )(Q 33 ),

[0082] Q 31 to Q 33 can each independently be selected from a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, and a pyridyl group,

[0083] Z3 and Z4 can optionally be linked to form a substituted or unsubstituted C5-C 10 carbocyclic group or a substituted or unsubstituted C1-C 10 heterocyclic group,

[0084] d2 can be an integer from 0 to 2,

[0085] d3 can be an integer from 0 to 3,

[0086] d4 can be an integer from 0 to 4,

[0087] d5 can be an integer from 0 to 5,

[0088] d6 can be an integer from 0 to 6,

[0089] d8 can be an integer from 0 to 8, and

[0090] * and *' each represent a connection site to an adjacent atom.

[0091] In Formula 2-2, a11 to a13 can each independently be an integer from 0 to 3. When a11 is 0, *-(L 11 ) a11 -*' represents a single bond. When a12 is 0, *-(L 12 ) a12 -*' represents a single bond, and when a13 is 0, *-(L 13 ) a13 -*' represents a single bond.

[0092] In some embodiments, for example, a11 can be 0.

[0093] Ar1 to Ar3 in Formula 2-1 and Formula 2-2 can each independently be a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group.

[0094] In one embodiment, Ar1 to Ar3 can each independently be selected from:

[0095] benzene group, pentacene group, indene group, naphthalene group, azulene group, heptacene group, indacene group, acenaphthylene group, fluorene group, spiro-cyclopentane-fluorene group, spiro-bifluorene group, benzo[b]fluorene group, dibenzo[b,d]fluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, pyrene group, group, tetracene group, picene group, perylene group, pyrrole group, thiophene group, furan group, silole group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, triazine group, benzofuran group, benzothiophene group, dibenzofuran group, dibenzothiophene group, carbazole group, benzosilole group, dibenzosilole group, quinoline group, isoquinoline group, benzimidazole group, imidazo[1,2-a]pyridine group, and imidazo[1,2-a]pyrimidine group;

[0096] each independently substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, C1-C 20Alkyl group, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, pentacenyl group, indenyl group, naphthyl group, azulene group, heptacenyl group, indacenyl group, acenaphthylenyl group, fluorenyl group, spiro-cyclopentane-fluorenyl group, spiro-difluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, pyrenyl group, yl group, tetracenyl group, picenyl group, perylenyl group, pyrrolyl group, thienyl group, furyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, carbazolyl group, benzosilolyl group, dibenzosilolyl group, quinolinyl group, isoquinolinyl group, benzimidazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), and -P(=O)(Q 31 )(Q 32 ), and at least one substituted benzene group, pentacene group, indene group, naphthalene group, azulene group, heptacene group, indacene group, acenaphthylene group, fluorene group, spiro-cyclopentane-fluorene group, spiro-difluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, pyrene group, yl group, tetracene group, picene group, perylene group, pyrrole group, thiophene group, furan group, silole group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, triazine group, benzofuran group, benzothiophene group, dibenzofuran group, dibenzothiophene group, carbazole group, benzosilole group, dibenzosilole group, quinoline group, isoquinoline group, benzimidazole group, imidazopyridine group, and imidazopyrimidine group,

[0097] Q 31 to Q 33 can each independently be selected from C1-C 20Alkyl group, C1-C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, and pyridyl group.

[0098] For example, Ar1 to Ar3 may each independently be a group represented by one selected from Formula 4-1 to Formula 4-24:

[0099]

[0100] In Formulas 4-1 to 4-24,

[0101] Y 31 may be O, S, C(Z 35 )(Z 36 ), N(Z 35 ) or Si(Z 35 )(Z 36 ),

[0102] Z 31 to Z 36 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, C1-C 20 alkyl group, C1-C 20 alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-cyclopentane-fluorenyl group, spiro-difluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, pyrenyl group, yl group, tetracenyl group, pyrrolyl group, thienyl group, furyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, carbazolyl group, benzosilolyl group, dibenzosilolyl group, quinolinyl group, isoquinolinyl group, benzimidazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and -Si(Q 31 )(Q 32 )(Q 33 ),

[0103] Q 31 to Q 33 may each independently be selected from C1-C 20 alkyl group, C1-C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, and pyridyl group,

[0104] e3 can be an integer from 0 to 3,

[0105] e4 can be an integer from 0 to 4,

[0106] e5 can be an integer from 0 to 5,

[0107] e6 can be an integer from 0 to 6,

[0108] e7 can be an integer from 0 to 7,

[0109] e8 can be an integer from 0 to 8,

[0110] e9 can be an integer from 0 to 9, and

[0111] * represents the connection site to adjacent atoms.

[0112] In one embodiment, Ar1 to Ar3 can each independently be selected from:

[0113] benzene group, naphthalene group, fluorene group, spiro-cyclopentane-fluorene group, spiro-difluorene group, benzofluorene group, dibenzofluorene group, dibenzofuran group, dibenzothiophene group, carbazole group, and dibenzosilole group; and

[0114] each independently substituted by at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, C1-C 20 alkyl group, C1-C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, spiro-cyclopentane-fluorenyl group, spiro-difluorenyl group, benzofluorenyl group, dibenzofluorenyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, dibenzosilolyl group, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ) of benzene group, naphthalene group, fluorene group, spiro-cyclopentane-fluorene group, spiro-difluorene group, benzofluorene group, dibenzofluorene group, dibenzofuran group, dibenzothiophene group, carbazole group, and dibenzosilole group,

[0115] Q 31 to Q 33may each independently be selected from C1-C 20 alkyl groups, C1-C 20 alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, and pyridyl groups.

[0116] In one embodiment, Ar1 in Formula 2-1 may be a benzene group, and

[0117] Ar2 and Ar3 in Formula 2-2 may each independently be selected from:

[0118] benzene groups, naphthalene groups, fluorene groups, spiro-cyclopentane-fluorene groups, spiro-difluorene groups, benzo-fluorene groups, dibenzo-fluorene groups, dibenzo-furan groups, dibenzo-thiophene groups, carbazole groups, and dibenzo-silole groups; and

[0119] benzene groups, naphthalene groups, fluorene groups, spiro-cyclopentane-fluorene groups, spiro-difluorene groups, benzo-fluorene groups, dibenzo-fluorene groups, dibenzo-furan groups, dibenzo-thiophene groups, carbazole groups, and dibenzo-silole groups each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl groups, cyano groups, C1-C 20 alkyl groups, C1-C 20 alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, spiro-cyclopentane-fluorenyl groups, spiro-difluorenyl groups, benzo-fluorenyl groups, dibenzo-fluorenyl groups, dibenzo-furanyl groups, dibenzo-thiophenyl groups, carbazolyl groups, dibenzo-silolyl groups, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), and -P(=O)(Q 31 )(Q 32 ), where Q 31 to Q 33 may each independently be selected from C1-C 20 alkyl groups, C1-C 20 alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, and pyridyl groups, but the embodiments of the present disclosure are not limited thereto.

[0120] Ar2 and Ar3 in Formula 2-2 may optionally be connected to each other via a single bond, -C(Q4)(Q5)-, -Si(Q4)(Q5)-, -O-, -S-, -N(Q4)-, -B(Q4)-, -C(=O)-, -S(=O)2-, -S(=O)(Q4)(Q5)- or -P(=O)(Q4)- to form a fused heterocycle.

[0121] For example, Ar2 and Ar3 may optionally be connected to each other via a single bond to form a fused heterocycle. For example, when each of Ar2 and Ar3 is a phenyl group, Ar2 and Ar3 may optionally be connected to each other via a single bond to form a carbazole group.

[0122] In one embodiment, the heterocyclic compound may be selected from Compound 1 to Compound 348:

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138] Because the heterocyclic compound represented by Formula 1 has excellent charge transport ability, the heterocyclic compound represented by Formula 1 can be suitably used as a hole transport material.

[0139] In addition, when the heterocyclic compound represented by Formula 1 has a structure in which the ninth carbon atom of fluorene is connected to the first position, the second position, or the fourth position of dibenzofuran or dibenzothiophene, the distance within the molecule (e.g., between moieties) becomes narrow, thereby obtaining the effect of stable structure.

[0140] In addition, since the heterocyclic compound represented by Formula 1 includes a dibenzofuran or dibenzothiophene structure, the glass transition temperature (Tg) of the compound can be relatively high. Therefore, the heat resistance to Joule heating of the compound when driving an organic light-emitting device including the heterocyclic compound can be improved, thereby obtaining the characteristic of long service life.

[0141] In addition, since the heterocyclic compound represented by Formula 1 has a structure in which the ninth carbon atom of the fluorenyl group represented by Formula 2-1 is directly connected to the nucleus (e.g., a dibenzofuran nucleus or a dibenzothiophene nucleus), the stability of the nucleus can be improved and the thermal stability of the heterocyclic compound can be improved, thereby obtaining the characteristic of long service life.

[0142] In addition, since the heterocyclic compound represented by Formula 1 includes the group represented by Formula 2-1 and the group represented by Formula 2-2, the heterocyclic compound represented by Formula 1 can have an energy level suitable for hole transport from the first electrode or the second electrode to the emission layer, thereby obtaining the characteristics of high efficiency and long service life.

[0143] By referring to the following examples, suitable synthesis methods for the heterocyclic compound represented by Formula 1 will be apparent to those of ordinary skill in the art.

[0144] At least one of the heterocyclic compounds represented by Formula 1 can be used between a pair of electrodes of an organic light-emitting device. For example, the heterocyclic compound can be included in the emission layer. In one or more embodiments, the heterocyclic compound represented by Formula 1 can be used as a material for a covering layer located outside a pair of electrodes of an organic light-emitting device.

[0145] One or more embodiments of the present disclosure provide an organic light-emitting device including: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer and at least one heterocyclic compound represented by Formula 1.

[0146] As used herein, the expression “(the organic layer) includes at least one heterocyclic compound” can refer to a case where “(the organic layer) includes the same heterocyclic compound represented by Formula 1 (e.g., the same compound)” and a case where “(the organic layer) includes two or more different heterocyclic compounds represented by Formula 1”.

[0147] For example, the organic layer may contain only Compound 1 (e.g., a single compound) as the heterocyclic compound. Here, Compound 1 may be present only in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may contain Compound 1 and Compound 2 (e.g., a first compound and a second compound) as the heterocyclic compounds. In this regard, Compound 1 and Compound 2 may be present in the same (e.g., identical) layer (e.g., both Compound 1 and Compound 2 may be present in the emission layer either both or simultaneously), or may be present in different layers (e.g., Compound 1 may be present in the emission layer and Compound 2 may be present in the hole transport layer).

[0148] In one embodiment,

[0149] the first electrode of the organic light-emitting device may be an anode,

[0150] the second electrode of the organic light-emitting device may be a cathode,

[0151] the organic layer may contain at least one heterocyclic compound represented by Formula 1,

[0152] the organic layer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,

[0153] the hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof, and

[0154] the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0155] In one embodiment, the hole transport region may contain a heterocyclic compound.

[0156] In one or more embodiments, the hole transport region includes a hole transport layer that contains a heterocyclic compound.

[0157] In one or more embodiments, the emission layer may contain a heterocyclic compound.

[0158] In one embodiment, the hole transport region may contain a p-dopant having a lowest unoccupied molecular orbital (LUMO) energy level of -3.5 eV or less than -3.5 eV.

[0159] For example, the p-dopant may include at least one selected from quinone derivatives, metal oxides, and compounds containing a cyano group.

[0160] For example, the hole transport region may include a hole transport layer, and the hole transport layer may contain a p-dopant, or the hole transport region may include a hole injection layer, and the hole injection layer may contain a p-dopant.

[0161] In one embodiment, the electron transport region of the organic light emitting device may contain an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0162] In one embodiment, the emissive layer may contain at least one compound selected from styryl-based compounds, anthracene-based compounds, pyrene-based compounds, spiro-bifluorene-based compounds, carbazole-based compounds, benzimidazole-based compounds, phosphine oxide-based compounds, dibenzofuran-based compounds, silicon-based compounds, and triazine-based compounds.

[0163] In one embodiment, the emissive layer may be a first emissive layer configured to emit light of a first color,

[0164] The organic light emitting device may further include, between the first electrode and the second electrode, i) at least one second emissive layer configured to emit light of a second color, or ii) at least one second emissive layer configured to emit light of a second color and at least one third emissive layer configured to emit light of a third color,

[0165] The maximum emission wavelength of the first color light, the maximum emission wavelength of the second color light, and the maximum emission wavelength of the third color light are the same as or different from each other, and

[0166] The first color light and the second color light may be emitted in the form of a mixed light, or the first color light, the second color light, and the third color light may be emitted in the form of a mixed light.

[0167] As used herein, the term "organic layer" may refer to a single layer and / or multiple layers disposed between the first electrode and the second electrode of the organic light emitting device. The materials included in the "organic layer" are not limited to organic materials.

[0168] For example, the organic light emitting device may have i) a stacked structure including a first electrode, an organic layer, a second electrode, and a second cover layer (stacked in this specified order), ii) a stacked structure including a first cover layer, a first electrode, an organic layer, and a second electrode (stacked in this specified order), or iii) a stacked structure including a first cover layer, a first electrode, an organic layer, a second electrode, and a second cover layer (stacked in this specified order), and at least one of the first cover layer and the second cover layer may contain the heterocyclic compound.

[0169] ​Figure 1 Description]

[0170] Figure 1 is a cross-sectional schematic view of an organic light-emitting device 10 according to an embodiment. The organic light-emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.

[0171] Hereinafter, the structure of the organic light-emitting device 10 according to an embodiment and a method of manufacturing the organic light-emitting device 10 will be described in conjunction with Figure 1 Description of the organic light-emitting device 10 according to an embodiment and a method of manufacturing the organic light-emitting device 10.

[0172] [First electrode 110]

[0173] In Figure 1 , a substrate may be additionally provided under the first electrode 110 or above the second electrode 190. The substrate may be a glass substrate and / or a plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and / or water resistance.

[0174] The first electrode 110 may be formed by depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be selected from materials having a high work function to facilitate hole injection.

[0175] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material for forming the first electrode may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and combinations thereof, but the embodiments of the present disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material for forming the first electrode may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but the embodiments of the present disclosure are not limited thereto.

[0176] The first electrode 110 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited thereto.

[0177] [Organic layer 150]

[0178] The organic layer 150 is disposed on the first electrode 110. The organic layer 150 may include an emission layer.

[0179] The organic layer 150 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 190.

[0180] [Hole transport region in the organic layer 150]

[0181] The hole transport region may have i) a single-layer structure including a single layer containing a single material, ii) a single-layer structure including a single layer containing a plurality of different materials, or iii) a multi-layer structure having a plurality of layers containing a plurality of different materials.

[0182] The hole transport region may include at least one layer selected from a hole injection layer, a hole transport layer, an emission assisting layer, and an electron blocking layer.

[0183] For example, the hole transport region may have a single-layer structure including a single layer containing a plurality of different materials, or a multi-layer structure having a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, where the constituent layers of each structure are sequentially stacked in a specified order from the first electrode 110, but the structure of the hole transport region is not limited thereto.

[0184] The hole transport region may contain a heterocyclic compound represented by Formula 1.

[0185] In one embodiment, the hole transport region may contain at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), the compound represented by Formula 201, and the compound represented by Formula 202:

[0186]

[0187] Formula 201

[0188]

[0189] Formula 202

[0190]

[0191] In Formulas 201 and 202,

[0192] L 201 to L 204 may each independently be selected from substituted or unsubstituted C3-C 10 cycloalkanediyl groups, substituted or unsubstituted C1-C 10 heterocycloalkanediyl groups, substituted or unsubstituted C3-C 10 cycloalkenediyl groups, substituted or unsubstituted C1-C 10 heterocycloalkenediyl groups, substituted or unsubstituted C6-C 60 arylene groups, substituted or unsubstituted C1-C 60 heteroarylene groups, substituted or unsubstituted divalent non-aromatic fused polycyclic groups, and substituted or unsubstituted divalent non-aromatic fused heteropolycyclic groups,

[0193] L 205 may be selected from *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C1-C 20 alkanediyl groups, substituted or unsubstituted C2-C 20 alkenediyl groups, substituted or unsubstituted C3-C 10 cycloalkanediyl groups, substituted or unsubstituted C1-C 10 heterocycloalkanediyl groups, substituted or unsubstituted C3-C 10 cycloalkenediyl groups, substituted or unsubstituted C1-C 10 heterocycloalkenediyl groups, substituted or unsubstituted C6-C 60 arylene groups, substituted or unsubstituted C1-C 60 heteroarylene groups, substituted or unsubstituted divalent non-aromatic fused polycyclic groups, and substituted or unsubstituted divalent non-aromatic fused heteropolycyclic groups,

[0194] xa1 to xa4 may each independently be an integer from 0 to 3,

[0195] xa5 may be an integer from 1 to 10, and

[0196] R 201 to R 204 and Q 201 may each independently be selected from substituted or unsubstituted C3-C 10 cycloalkyl groups, substituted or unsubstituted C1-C 10 heterocycloalkyl groups, substituted or unsubstituted C3-C 10 cycloalkenyl groups, substituted or unsubstituted C1-C 10 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60Aryl group, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio group, substituted or unsubstituted C1-C 60 Heteroaryl group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

[0197] In one embodiment, in Formula 202, R 201 and R 202 may optionally be connected to each other via a single bond, a dimethyl-methylene group or a diphenyl-methylene group, and R 203 and R 204 may optionally be connected to each other via a single bond, a dimethyl-methylene group or a diphenyl-methylene group.

[0198] In one or more embodiments, in Formulas 201 and 202,

[0199] L 201 to L 205 may each independently be selected from:

[0200] Phenylene group, pentalenylene group, indenylene group, naphthylene group, azulylene group, heptalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-bifluorenylene group, benzo-fluorenylene group, dibenzo-fluorenylene group, phenalenylene group, phenanthrylene group, anthrylene group, fluoranthenylene group, benzophenanthrylene group, pyrenylene group, sub- yl group, terrylene group, picenylene group, perylenylene group, quaterrylene group, hexacenylene group, pentacenylene group, rubicenylene group, coronenylene group, ovalenylene group, thienylene group, furylene group, carbazolylene group, indolylene group, isoindolylene group, benzofurylene group, benzothienylene group, dibenzofurylene group, dibenzothienylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group and pyridinylene group; and

[0201] Each independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 alkyl group, C1-C 20 alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, substituted by C1-C 10An alkyl group-substituted phenyl group, a phenyl group substituted with -F, a pentalenyl group, an indenyl group, a naphthyl group, a azulene group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorene group, a spiro-bifluorene group, a benzo[b]fluorene group, a dibenzo[b,d]fluorene group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a benzo[a]phenanthrenyl group, a pyrenyl group, a group, a tetraphenyl group, a picene group, a perylene group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a rubicene group, a coronene group, an ovalene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridyl group, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ) and at least one of a substituted phenylene group, a subpentalenyl group, a subindenyl group, a subnaphthyl group, a subazulene group, a subheptalenyl group, a subindacenyl group, a subacenaphthyl group, a subfluorene group, a spiro-subbifluorene group, a subbenzo[b]fluorene group, a subdibenzo[b,d]fluorene group, a subphenalenyl group, a subphenanthrenyl group, a subanthracenyl group, a subfluoranthenyl group, a subbenzo[a]phenanthrenyl group, a subpyrenyl group, a sub group, a subtetraphenyl group, a subpicene group, a subperylene group, a subpentaphenyl group, a subhexaphenyl group, a subpentacene group, a subrubicene group, a subcoronene group, a subovalene group, a subthienyl group, a subfuryl group, a subcarbazolyl group, a subindolyl group, a subisoindolyl group, a subbenzofuranyl group, a subbenzothienyl group, a subdibenzo[bf]uranyl group, a subdibenzo[b,d]thienyl group, a subbenzocarbazolyl group, a subdibenzo[b,d]carbazolyl group, a subdibenzo[b,d]silolyl group and a subpyridyl group, and

[0202] Q 31 to Q 33 can each independently be selected from a C1-C 10 alkyl group, a C1-C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group.

[0203] In one or more embodiments, xa1 to xa4 can each independently be 0, 1 or 2.

[0204] In one or more embodiments, xa5 can be 1, 2, 3 or 4.

[0205] In one or more embodiments, R 201 through R 204 and Q 201 may each independently be selected from:

[0206] phenyl group, biphenyl group, terphenyl group, pentaphenylenyl group, indenyl group, naphthyl group, azulene group, heptaphenylenyl group, indacenyl group, acenaphthylenyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, benzo[a]phenanthrenyl group, pyrenyl group, group, tetraphenyl group, picenyl group, perylenyl group, pentaphenyl group, hexaphenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, thienyl group, furyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, and pyridyl group; and

[0207] each independently being selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 alkyl group, C1-C 20 alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, phenyl group substituted with C1-C 10 alkyl group, phenyl group substituted with -F, pentaphenylenyl group, indenyl group, naphthyl group, azulene group, heptaphenylenyl group, indacenyl group, acenaphthylenyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, benzo[a]phenanthrenyl group, pyrenyl group, group, tetraphenyl group, picenyl group, perylenyl group, pentaphenyl group, hexaphenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, thienyl group, furyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridyl group, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32at least one of the substituted phenyl group, biphenyl group, terphenyl group, pentacenyl group, indenyl group, naphthyl group, azulene group, heptacenyl group, indacenyl group, acenaphthyl group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, benzophenanthrenyl group, pyrenyl group, group, tetraphenyl group, picene group, perylene group, pentaphenyl group, hexaphenyl group, pentacene group, rubicene group, coronene group, ovalene group, thiophene group, furan group, carbazole group, indole group, isoindole group, benzofuran group, benzothiophene group, dibenzofuran group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzosilole group and pyridyl group, and

[0208] Q 31 to Q 33 may each independently be the same as those described above.

[0209] In one or more embodiments, R selected from Formula 201 201 to R 203 at least one of which may each independently be selected from:

[0210] fluorene group, spiro-bifluorene group, carbazole group, dibenzofuran group and dibenzothiophene group; and

[0211] each independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazone group, C1-C 20 alkyl group, C1-C 20 alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, phenyl group substituted with C1-C 10 alkyl group, phenyl group substituted with -F, naphthyl group, fluorene group, spiro-bifluorene group, carbazole group, dibenzofuran group and dibenzothiophene group, fluorene group, spiro-bifluorene group, carbazole group, dibenzofuran group and dibenzothiophene group substituted with at least one of

[0212] However, the embodiments of the present disclosure are not limited thereto.

[0213] In one or more embodiments, in Formula 202, i) R 201 and R 202 may be connected to each other via a single bond, and / or ii) R 203 and R 204Can be connected to each other via a single key.

[0214] In one or more embodiments, R selected from Formula 202 201 to R 204 at least one of which may be selected from:

[0215] a carbazolyl group; and

[0216] selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazone group, C1-C 20 alkyl group, C1-C 20 alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, phenyl group substituted with a C1-C 10 alkyl group, phenyl group substituted with -F, naphthyl group, fluorenyl group, spiro-bifluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group, and a carbazolyl group substituted with at least one of them,

[0217] However, the embodiments of the present disclosure are not limited thereto.

[0218] The compound represented by Formula 201 may be represented by Formula 201A:

[0219] Formula 201A

[0220]

[0221] In one embodiment, the compound represented by Formula 201 may be represented by Formula 201A(1), but the embodiments of the present disclosure are not limited thereto:

[0222] Formula 201A(1)

[0223]

[0224] In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A-1, but the embodiments of the present disclosure are not limited thereto:

[0225] Formula 201A-1

[0226]

[0227] In one embodiment, the compound represented by Formula 202 may be represented by Formula 202A:

[0228] Formula 202A

[0229]

[0230] In one or more embodiments, the compound represented by Formula 202 may be represented by Formula 202A-1:

[0231] Formula 202A-1

[0232]

[0233] In Formulas 201A, 201A(1), 201A-1, 202A, and 202A-1,

[0234] L 201 to L 203 , xa1 to xa3, xa5, and R 202 to R 204 may each be understood by referring to the corresponding descriptions presented herein,

[0235] R 211 and R 212 may each be understood by referring to the description presented regarding R 203 and,

[0236] R 213 to R 217 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxy group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C 10 alkyl group, a phenyl group substituted with -F, a pentaphenylenyl group, an indenyl group, a naphthyl group, an azulene group, a heptaphenylenyl group, an indacenyl group, an acenaphthylenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthryl group, an anthryl group, a fluoranthenyl group, a benzo[a]phenanthryl group, a pyrenyl group, a perylenyl group, a tetraphenylenyl group, a picenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridyl group.

[0237] The hole transport region may include at least one compound selected from Compounds HT1 to HT39, but embodiments of the present disclosure are not limited thereto:

[0238]

[0239]

[0240]

[0241] The hole transport region may have a thickness of about to about (e.g., about to about ). When the hole transport region includes at least one selected from a hole injection layer and a hole transport layer, the hole injection layer may have a thickness of about to about (e.g., about to about ), and the hole transport layer may have a thickness of about to about (e.g., about to about ). When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in the driving voltage.

[0242] The emission assisting layer can increase the light emission efficiency by compensating for the optical resonance distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block or reduce the flow of electrons from the electron transport region. The emission assisting layer and the electron blocking layer can include the materials described above.

[0243] [p-dopant]

[0244] In addition to these materials, the hole transport region may further include a charge generation material for improving the conductive properties. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region.

[0245] The charge generation material may be, for example, a p-dopant.

[0246] In one embodiment, the p-dopant may have a LUMO energy level of -3.5 eV or less than -3.5 eV.

[0247] The p-dopant may include at least one selected from quinone derivatives, metal oxides, and compounds containing a cyano group, but the embodiments of the present disclosure are not limited thereto.

[0248] In one embodiment, the p-dopant may include at least one selected from the following:

[0249] Quinone derivatives (such as tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ));

[0250] Metal oxides (such as tungsten oxide and / or molybdenum oxide);

[0251] 1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and

[0252] A compound represented by Formula 221,

[0253] However, the embodiments of the present disclosure are not limited thereto:

[0254]

[0255]

[0256] Formula 221

[0257]

[0258] In Formula 221,

[0259] R 221 to R 223 may each independently be selected from substituted or unsubstituted C3-C 10 cycloalkyl groups, substituted or unsubstituted C1-C 10 heterocycloalkyl groups, substituted or unsubstituted C3-C 10 cycloalkenyl groups, substituted or unsubstituted C1-C 10 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C1-C 60 heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic groups, wherein at least one selected from R 221 to R 223 may have at least one substituent selected from a cyano group, -F, -Cl, -Br, -I, a C1-C 20 alkyl group substituted with -F, a C1-C 20 alkyl group substituted with -Cl, a C1-C 20 alkyl group substituted with -Br, and a C1-C 20 alkyl group substituted with -I.

[0260] [Emission layer in organic layer 150]

[0261] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer can be patterned into a red emission layer, a green emission layer, or a blue emission layer according to sub-pixels. In one or more embodiments, the emission layer can have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, wherein the two or more layers can be in contact with each other or can be spaced apart from each other. In one or more embodiments, the emission layer can contain two or more materials selected from a material that emits red light, a material that emits green light, and a material that emits blue light, wherein the two or more materials are mixed with each other in a single layer to emit white light.

[0262] The emission layer can contain a host and a dopant. The dopant can include at least one selected from a phosphorescent dopant and a fluorescent dopant.

[0263] In the emission layer, based on 100 parts by weight of the host, the dopant can be contained in an amount of about 0.01 part by weight to about 15 parts by weight, but the embodiments of the present disclosure are not limited thereto.

[0264] The emission layer can have a thickness of about to about (e.g., about to about ). When the thickness of the emission layer is within this range, excellent light emission characteristics can be obtained without a significant increase in the driving voltage.

[0265] [Host in the emission layer]

[0266] In one or more embodiments, the host can include a compound represented by Formula 301:

[0267] Formula 301

[0268] [Ar 301 xb11 -[(L 301 ) xb1 -R 301 xb21 .

[0269] In Formula 301,

[0270] Ar 301 can be a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group,

[0271] xb11 can be 1, 2, or 3,

[0272] L 301 can be selected from substituted or unsubstituted C3-C​​10 A cycloalkylidene group, a substituted or unsubstituted C1-C 10 A heterocycloalkylidene group, a substituted or unsubstituted C3-C 10 A cycloalkenylidene group, a substituted or unsubstituted C1-C 10 A heterocycloalkenylidene group, a substituted or unsubstituted C6-C 60 An arylidene group, a substituted or unsubstituted C1-C 60 A heteroarylidene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, and a substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group,

[0273] xb1 can be an integer from 0 to 5,

[0274] R 301 can be selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O)2(Q 301 ) and -P(=O)(Q 301 )(Q 302 ),

[0275] xb21 can be an integer from 1 to 5, and

[0276] Q 301 to Q 303 may each independently be selected from C1-C 10 alkyl groups, C1-C 10 alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups, but the embodiments of the present disclosure are not limited thereto.

[0277] In one embodiment, Ar in Formula 301 301 may be selected from:

[0278] naphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenalenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, benzophenanthrenyl groups, pyrenyl groups, groups, tetracenyl groups, picenyl groups, perylenyl groups, pentacenyl groups, indenoanthracenyl groups, dibenzofuranyl groups, and dibenzothiophenyl groups; and

[0279] each naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, benzophenanthrenyl group, pyrenyl group, 20 alkyl groups, C1-C 20 alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), and -P(=O)(Q 31 )(Q 32 ) substituted with at least one of and groups, tetracenyl groups, picenyl groups, perylenyl groups, pentacenyl groups, indenoanthracenyl groups, dibenzofuranyl groups, and dibenzothiophenyl groups, and

[0280] Q 31 to Q 33 may each independently be selected from C1-C 10 alkyl groups, C1-C 10 alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups, but the embodiments of the present disclosure are not limited thereto.

[0281] When xb11 in Formula 301 is 2 or greater than 2, two or more than two Ars 301 can be connected to each other via a single bond.

[0282] In one or more embodiments, the compound represented by Formula 301 can be represented by Formula 301-1 or Formula 301-2:

[0283] Formula 301-1

[0284]

[0285] Formula 301-2

[0286]

[0287] In Formula 301-1 and Formula 301-2,

[0288] A 301 to A 304 can each independently be selected from benzene, naphthalene, phenanthrene, fluoranthene, benzophenanthrene, pyrene, pyridine, pyrimidine, indene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, indole, carbazole, benzocarbazole, dibenzocarbazole, furan, benzofuran, dibenzofuran, naphthofuran, benzonaphthofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthothiophene, benzonaphthothiophene and dinaphthothiophene,

[0289] X 301 can be O, S or N-[(L 304 ) xb4 -R 304 ,

[0290] R 311 to R 314 can each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ),

[0291] xb22 and xb23 can each independently be 0, 1, or 2,

[0292] L 301 , xb1, R 301 and Q 31 to Q 33 can each be understood by referring to the corresponding descriptions presented herein,

[0293] L 302 to L 304 can each be understood by referring to the description presented regarding L 301 presented,

[0294] xb2 to xb4 can each be understood by referring to the description presented regarding xb1, and

[0295] R 302 to R 304 can each be understood by referring to the description presented regarding R 301 presented.

[0296] For example, L 301 to L 304 in Formula 301, Formula 301-1, and Formula 301-2 can each independently be selected from:

[0297] a phenylene group, a naphthylene group, a fluorene group, a spiro-bifluorene group, a benzo[a]fluorene group, a dibenzo[a,h]fluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a benzo[a]phenanthrene group, a pyrene group, a group, a perylene group, a pentacene group, a hexacene group, a tetracene group, a thiophene group, a furan group, a carbazole group, an indole group, an isoindole group, a benzofuran group, a benzothiophene group, a dibenzofuran group, a dibenzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzosilole group, a pyridine group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a thiadiazole group, an oxadiazole group, a pyrazine group, a pyrimidine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; and

[0298] Each is independently selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C1-C 20 alkyl group, C1-C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, anthryl group, fluoranthenyl group, benzophenanthryl group, pyrenyl group, perylenyl group, pentaphenyl group, hexaphenyl group, quinquephenyl group, thienyl group, furyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), and -P(=O)(Q 31 )(Q 32 ), and at least one of the substituted phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrylene group, anthrylene group, fluoranthenylene group, benzophenanthrylene group, pyrenylene group, sub- A base group, a perylene diimide group, a pentacene diimide group, a hexacene diimide group, a pentacenequinone diimide group, a thiophene diimide group, a furan diimide group, a carbazole diimide group, an indole diimide group, an isoindole diimide group, a benzofuran diimide group, a benzothiophene diimide group, a dibenzofuran diimide group, a dibenzothiophene diimide group, a benzocarbazole diimide group, a dibenzocarbazole diimide group, a dibenzosilole diimide group, a pyridine diimide group, an imidazole diimide group, a pyrazole diimide group, a thiazole diimide group, an isothiazole diimide group, an oxazole diimide group, an isoxazole diimide group, a thiadiazole diimide group, an oxadiazole diimide group, a pyrazine diimide group, a pyrimidine diimide group, a pyridazine diimide group, a triazine diimide group, a quinoline diimide group, an isoquinoline diimide group, a benzoquinoline diimide group, a phthalazine diimide group, a naphthyridine diimide group, a quinoxaline diimide group, a quinazoline diimide group, a cinnoline diimide group, a phenanthridine diimide group, an acridine diimide group, a phenanthroline diimide group, a phenazine diimide group, a benzimidazole diimide group, an isobenzothiazole diimide group, a benzoxazole diimide group, an isobenzoxazole diimide group, a triazole diimide group, a tetrazole diimide group, an imidazopyridine diimide group, an imidazopyrimidine diimide group, and an azacarbazole diimide group, and

[0299] Q 31 to Q 33 may each independently be the same as those described above.

[0300] In one embodiment, R in Formula 301, Formula 301-1, and Formula 301-2 301 to R 304 may each independently be selected from:

[0301] a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorene group, a spiro-bifluorene group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a benzo[a]phenanthrenyl group, a pyrenyl group, Group, perylene group, pentaphenyl group, hexaphenyl group, pentacene group, thiophene group, furan group, carbazole group, indole group, isoindole group, benzofuran group, benzothiophene group, dibenzofuran group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzosilole group, pyridine group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, thiadiazole group, oxadiazole group, pyrazine group, pyrimidine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, imidazopyridine group, imidazopyrimidine group, and azacarbazole group; and

[0302] each independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazone group, C1-C 20 alkyl group, C1-C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthryl group, anthracenyl group, fluoranthenyl group, benzophenanthryl group, pyrenyl group, Group, perylene group, pentaphenyl group, hexaphenyl group, pentacene group, thiophene group, furan group, carbazole group, indole group, isoindole group, benzofuran group, benzothiophene group, dibenzofuran group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzosilole group, pyridine group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, thiadiazole group, oxadiazole group, pyrazine group, pyrimidine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, imidazopyridine group, imidazopyrimidine group, azacarbazole group, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), and -P(=O)(Q 31 )(Q 32 ), at least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro - bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, benzophenanthryl group, pyrenyl group, -yl group, perylenyl group, pentaphenyl group, hexaphenyl group, quaterphenyl group, thienyl group, furyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridyl group, imidazopyrimidinyl group, and azacarbazolyl group, and

[0303] Q 31 to Q 33 can each independently be the same as those described above.

[0304] In one or more embodiments, the host may include an alkaline earth metal complex. For example, the host may be selected from Be complexes (e.g., compound H55) and Mg complexes. In some embodiments, the host may include Zn complexes.

[0305] The host may include at least one selected from 9,10 - bis(2 - naphthyl)anthracene (ADN), 2 - methyl - 9,10 - bis(naphthalen - 2 - yl)anthracene (MADN), 9,10 - bis(2 - naphthyl)-2 - tert - butyl - anthracene (TBADN), 4,4′ - bis(N - carbazolyl)-1,1′ - biphenyl (CBP), 1,3 - bis - 9 - carbazolylbenzene (mCP), 1,3,5 - tris(carbazol - 9 - yl)benzene (TCP), and compounds H1 to H55, but the embodiments of the present disclosure are not limited thereto:

[0306]

[0307]

[0308]

[0309] [Phosphorescent dopant contained in the emission layer in the organic layer 150]

[0310] The phosphorescent dopant may include an organometallic complex represented by Formula 401:

[0311] Formula 401

[0312] M(L 401 ) xc1 (L 402 ) xc2 ,

[0313] Formula 402

[0314]

[0315] In Formula 401 and Formula 402,

[0316] M may be selected from iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), and thulium (Tm),

[0317] L 401 may be selected from the ligands represented by Formula 402, and xc1 may be 1, 2, or 3, where, when xc1 is 2 or greater than 2, two or more L 401 may be the same as or different from each other,

[0318] L 402 may be an organic ligand, and xc2 may be an integer from 0 to 4, where, when xc2 is 2 or greater than 2, two or more L 402 may be the same as or different from each other,

[0319] X 401 to X 404 may each independently be nitrogen or carbon,

[0320] X 401 and X 403 may be connected to each other via a single bond or a double bond, and X 402 and X 404 may be connected to each other via a single bond or a double bond,

[0321] A 401 and A 402 may each independently be selected from C5-C 60A carbocyclic group or a C1-C 60 heterocyclic group,

[0322] X 405 can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )(-*', *-C(Q 411 )(Q 412 )(-*', *-C(Q 411 )=C(Q 412 )(-*', *-C(Q 411 )=*' or * = C = *', where Q 411 and Q 412 can be hydrogen, deuterium, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group,

[0323] X 406 can be a single bond, O or S,

[0324] R 401 and R 402 can each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxy group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C 20 alkyl group, a substituted or unsubstituted C1-C 20 alkoxy group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group and a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 401 )(Q 402 )(Q 403 ), -N(Q 401 )(Q 402 ), -B(Q 401 )(Q 402 ), -C(=O)(Q 401 ), -S(=O)2(Q401 ) and -P(=O)(Q 401 )(Q 402 ), where Q 401 to Q 403 can each independently be selected from C1-C 10 alkyl groups, C1-C 10 alkoxy groups, C6-C 20 aryl groups and C1-C 20 heteroaryl groups,

[0325] xc11 and xc12 can each independently be an integer from 0 to 10, and

[0326] * and *' in Formula 402 each represent the attachment site to M in Formula 401.

[0327] In one embodiment, A in Formula 402 401 and A 402 can each independently be selected from benzene groups, naphthalene groups, fluorene groups, spiro-bifluorene groups, indene groups, pyrrole groups, thiophene groups, furan groups, imidazole groups, pyrazole groups, thiazole groups, isothiazole groups, oxazole groups, isoxazole groups, pyridine groups, pyrazine groups, pyrimidine groups, pyridazine groups, quinoline groups, isoquinoline groups, benzoquinoline groups, quinoxaline groups, quinazoline groups, carbazole groups, benzimidazole groups, benzofuran groups, benzothiophene groups, isobenzothiophene groups, benzoxazole groups, isobenzoxazole groups, triazole groups, tetrazole groups, oxadiazole groups, triazine groups, dibenzofuran groups and dibenzothiophene groups.

[0328] In one or more embodiments, in Formula 402, i) X 401 can be nitrogen and X 402 can be carbon, or ii) X 401 and X 402 can each simultaneously (e.g., concurrently) be nitrogen.

[0329] In one or more embodiments, R in Formula 402 401 and R 402 can each independently be selected from:

[0330] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl groups, cyano groups, nitro groups, amidino groups, hydrazino groups, hydrazone groups, C1-C 20 alkyl groups and C1-C 20 alkoxy groups;

[0331] A C1-C alkyl group and a C1-C alkoxy group each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazone group, a phenyl group, a naphthyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, and a norbornenyl group; 20 A C1-C 20 alkoxy group;

[0332] A cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorene group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

[0333] A cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorene group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazone group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorene group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

[0334] -Si(Q 401 )(Q 402 )(Q 403 ), -N(Q 401 )(Q 402 ), -B(Q 401 )(Q 402 ), -C(=O)(Q 401 ), -S(=O)2(Q 401 ), and -P(=O)(Q 401 )(Q 402 ), and

[0335] Q 401 to Q 403 may each independently be selected from C1-C 10 alkyl groups, C1-C 10 alkoxy groups, phenyl groups, biphenyl groups, and naphthyl groups, but the embodiments of the present disclosure are not limited thereto.

[0336] In one or more embodiments, when xc1 in Formula 401 is 2 or greater than 2, two or more of the L 401 in two of the A 401 may optionally be connected to each other via X 407 serving as a linking group, or two or more of the L 401 in two of the A 402 may optionally be connected to each other via X 408 serving as a linking group (see Compounds PD1 to PD4 and Compound PD7). X 407 and X 408 may each independently be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 413 )-*', *-C(Q 413 )(Q 414 )-*' or *-C(Q 413 )=C(Q 414 )-*' (where Q 413 and Q 414 may each independently be hydrogen, deuterium, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group), but is not limited thereto.

[0337] L in Formula 401 402 may be a monovalent organic ligand, a divalent organic ligand, or a trivalent organic ligand. For example, L 402 may be selected from halogens, diketones (e.g., acetylacetonates), carboxylic acids (e.g., picolinates), -C(=O), isonitriles, -CN, and phosphorus compounds (e.g., phosphines or phosphites), but the embodiments of the present disclosure are not limited thereto.

[0338] In one or more embodiments, the phosphorescent dopant may be selected from, for example, Compounds PD1 to PD25, but the embodiments of the present disclosure are not limited thereto:

[0339]

[0340]

[0341] [Fluorescent dopant in the emission layer]

[0342] The fluorescent dopant may include an arylamine compound or a styrylamine compound.

[0343] The fluorescent dopant may include a compound represented by Formula 501:

[0344] Formula 501

[0345]

[0346] In Formula 501,

[0347] Ar 501 may be a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group,

[0348] L 501 to L 503 may each independently be selected from a substituted or unsubstituted C3-C 10 subcycloalkyl group, a substituted or unsubstituted C1-C 10 subheterocycloalkyl group, a substituted or unsubstituted C3-C 10 subcycloalkenyl group, a substituted or unsubstituted C1-C 10 subheterocycloalkenyl group, a substituted or unsubstituted C6-C 60 subaryl group, a substituted or unsubstituted C1-C 60 subheteroaryl group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group and a substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group,

[0349] xd1 to xd3 may each independently be an integer from 0 to 3,

[0350] R 501 and R 502 may each independently be selected from a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C1-C 60Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic groups, and

[0351] xd4 can be an integer from 1 to 6.

[0352] In one embodiment, Ar in Formula 501 501 can be selected from:

[0353] naphthalene groups, heptalene groups, fluorene groups, spiro-bifluorene groups, benzofluorene groups, dibenzofluorene groups, phenalene groups, phenanthrene groups, anthracene groups, fluoranthene groups, benzo[a]phenanthrene groups, pyrene groups, groups, tetracene groups, picene groups, perylene groups, pentacene groups, indeno[1,2,3-cd]anthracene groups, and indeno[1,2,3-cd]phenanthrene groups; and

[0354] each naphthalene group, heptalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, benzo[a]phenanthrene group, pyrene group, 20 alkyl group, C1-C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group, and naphthyl group, which are each substituted by at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazone group, C1-C groups, tetracene groups, picene groups, perylene groups, pentacene groups, indeno[1,2,3-cd]anthracene groups, and indeno[1,2,3-cd]phenanthrene groups.

[0355] In one or more embodiments, L in Formula 501 501 to L 503 can each independently be selected from:

[0356] phenylene groups, naphthylene groups, fluorenylene groups, spiro-bifluorenylene groups, benzofluorenylene groups, dibenzofluorenylene groups, phenanthrylene groups, anthrylene groups, fluoranthenylene groups, benzo[a]phenanthrylene groups, pyrenylene groups, sub- groups, perylenylene groups, pentaphenylene groups, hexacenylene groups, pentacenylene groups, thiophene groups, furan groups, carbazolyl groups, indolyl groups, isoindolyl groups, benzofuran groups, benzothiophene groups, dibenzofuran groups, dibenzothiophene groups, benzocarbazolyl groups, dibenzocarbazolyl groups, dibenzosilolyl groups, and pyridyl groups; and

[0357] each deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazone group, C1-C 20 alkyl group, C1-C20 alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro - difluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, anthryl group, fluoranthenyl group, benzophenanthryl group, pyrenyl group, at least one of the groups, perylenyl group, pentaphenyl group, hexaphenyl group, quinquephenyl group, thienyl group, furyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuryl group, benzothienyl group, dibenzofuryl group, dibenzothienyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridyl group substituted phenylene group, naphthylene group, fluorenylene group, spiro - difluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrylene group, anthrylene group, fluoranthenylene group, benzophenanthrylene group, pyrenylene group, group, perylenylene group, pentaphenylene group, hexaphenylene group, quinquephenylene group, thienylene group, furylene group, carbazolylene group, indolylene group, isoindolylene group, benzofurylene group, benzothienylene group, dibenzofurylene group, dibenzothienylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group and pyridinylene group.

[0358] In one or more embodiments, R in Formula 501 501 and R 502 can each independently be selected from:

[0359] phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro - difluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, anthryl group, fluoranthenyl group, benzophenanthryl group, pyrenyl group, group, perylenyl group, pentaphenyl group, hexaphenyl group, quinquephenyl group, thienyl group, furyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuryl group, benzothienyl group, dibenzofuryl group, dibenzothienyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridyl group; and

[0360] each independently selected from deuterium, -F, -Cl, -Br, -I, hydroxy group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1 - C 20 alkyl group, C1 - C 20An alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-difluorenyl group, a benzo[h]fluorenyl group, a dibenzo[h,k]fluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a benzo[a]phenanthryl group, a pyrenyl group, a perylenyl group, a pentaphenyl group, a sexiphenyl group, a quaterphenyl group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzo[c]carbazolyl group, a dibenzo[c,g]carbazolyl group, a dibenzosilolyl group, a pyridyl group and -Si(Q 31 )(Q 32 )(Q 33 ) and at least one of the substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[h]fluorenyl group, dibenzo[h,k]fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, benzo[a]phenanthryl group, pyrenyl group, a perylenyl group, a pentaphenyl group, a sexiphenyl group, a quaterphenyl group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzo[c]carbazolyl group, a dibenzo[c,g]carbazolyl group, a dibenzosilolyl group and a pyridyl group, and

[0361] Q 31 to Q 33 can each independently be selected from a C1-C 10 alkyl group, a C1-C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group.

[0362] In one or more embodiments, xd4 in Formula 501 can be 2, but the embodiments of the present disclosure are not limited thereto.

[0363] For example, the fluorescent dopant can be selected from Compound FD1 to Compound FD22:

[0364]

[0365]

[0366]

[0367] In one or more embodiments, the fluorescent dopant can be selected from the following compounds, but the embodiments of the present disclosure are not limited thereto:

[0368]

[0369] [Electron transport region in organic layer 150]

[0370] The electron transport region may have i) a single-layer structure including a single layer containing a single material, ii) a single-layer structure including a single layer containing a plurality of different materials, or iii) a multi-layer structure having a plurality of layers containing a plurality of different materials.

[0371] The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but the embodiments of the present disclosure are not limited thereto.

[0372] For example, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the constituent layers of each structure are stacked in a prescribed order from the emission layer. However, the embodiments of the structure of the electron transport region are not limited thereto.

[0373] The electron transport region (e.g., the buffer layer, hole blocking layer, electron control layer, and / or electron transport layer in the electron transport region) may contain a metal-free compound containing at least one nitrogen-containing ring depleted in π electrons.

[0374] "Nitrogen-containing ring depleted in π electrons" means a C1-C 60 heterocyclic group having at least one *-N=*' moiety as a ring-forming moiety.

[0375] For example, "nitrogen-containing ring depleted in π electrons" may be i) a 5- to 7-membered hetero-monocyclic group having at least one *-N=*' moiety, ii) a hetero-polycyclic group in which two or more 5- to 7-membered hetero-monocyclic groups each having at least one *-N=*' moiety are fused to each other, or iii) a hetero-polycyclic group in which at least one 5- to 7-membered hetero-monocyclic group having at least one *-N=*' moiety is fused to at least one C5-C 60 carbocyclic group.

[0376] Non-limiting examples of nitrogen-containing rings with π-electron depletion include imidazole groups, pyrazole groups, thiazole groups, isothiazole groups, oxazole groups, isoxazole groups, pyridine groups, pyrazine groups, pyrimidine groups, pyridazine groups, indazole groups, purine groups, quinoline groups, isoquinoline groups, benzoquinoline groups, phthalazine groups, naphthyridine groups, quinoxaline groups, quinazoline groups, cinnoline groups, phenanthridine groups, acridine groups, phenanthroline groups, phenazine groups, benzimidazole groups, isobenzothiazole groups, benzoxazole groups, isobenzoxazole groups, triazole groups, tetrazole groups, oxadiazole groups, triazine groups, thiadiazole groups, imidazopyridine groups, imidazopyrimidine groups, and azacarbazole groups, but are not limited thereto.

[0377] For example, the electron transport region may include a compound represented by Formula 601:

[0378] Formula 601

[0379] [Ar 601 xe11 -[(L 601 ) xe1 -R 601 xe21 .

[0380] In Formula 601,

[0381] Ar 601 may be a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group,

[0382] xe11 may be 1, 2, or 3,

[0383] L 601 may be selected from substituted or unsubstituted C3-C 10 subcycloalkyl groups, substituted or unsubstituted C1-C 10 subheterocycloalkyl groups, substituted or unsubstituted C3-C 10 subcycloalkenyl groups, substituted or unsubstituted C1-C 10 subheterocycloalkenyl groups, substituted or unsubstituted C6-C 60 subaryl groups, substituted or unsubstituted C1-C 60 subheteroaryl groups, substituted or unsubstituted divalent non-aromatic fused polycyclic groups, and substituted or unsubstituted divalent non-aromatic fused heteropolycyclic groups;

[0384] xe1 may be an integer from 0 to 5,

[0385] R 601 may be selected from substituted or unsubstituted C3-C 10 cycloalkyl groups, substituted or unsubstituted C1-C​​10 Heterocycloalkyl group, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C1-C 10 Heterocycloalkenyl group, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio group, substituted or unsubstituted C1-C 60 Heteroaryl group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 601 )(Q 602 )(Q 603 ), -C(=O)(Q 601 ), -S(=O)2(Q 601 ), and -P(=O)(Q 601 )(Q 602 ),

[0386] Q 601 to Q 603 can each independently be a C1-C 10 alkyl group, a C1-C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group, and

[0387] xe21 can be an integer from 1 to 5.

[0388] In one embodiment, at least one of the xe11 Ar 601 groups and the xe21 R 601 groups can contain a nitrogen-containing ring with π-electron depletion.

[0389] In one embodiment, Ar in Formula 601 601 can be selected from:

[0390] benzene group, naphthalene group, fluorene group, spiro-bifluorene group, benzo[fluorene group, dibenzo[fluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, benzo[phenanthrene group, pyrene group, Group, tetracene group, picene group, perylene group, pentacene group, indenoanthracene group, dibenzofuran group, dibenzothiophene group, carbazole group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, and azacarbazole group; and

[0391] each independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 alkyl group, C1-C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -S(=O)2(Q 31 ), and -P(=O)(Q 31 )(Q 32 ), and at least one of the substituted benzene group, naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, benzo[a]pyrene group, Group, tetracene group, picene group, perylene group, pentacene group, indenoanthracene group, dibenzofuran group, dibenzothiophene group, carbazole group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, and azacarbazole group, and

[0392] Q 31 to Q 33 may each independently be selected from C1-C 10 alkyl group, C1-C 10 alkoxy group, phenyl group, biphenyl group, terphenyl group, and naphthyl group.

[0393] When xe11 in Formula 601 is 2 or greater than 2, two or more than two Ars 601 groups can be connected to each other via a single bond.

[0394] In one or more embodiments, Ar in Formula 601 601 can be an anthracene group.

[0395] In one or more embodiments, the compound represented by Formula 601 can be represented by Formula 601-1:

[0396] Formula 601-1

[0397]

[0398] In Formula 601-1,

[0399] X 614 can be N or C(R 614 ), X 615 can be N or C(R 615 ), X 616 can be N or C(R 616 ), and at least one selected from X 614 to X 616 can be N,

[0400] L 611 to L 613 can each be understood by referring to the description presented regarding L 601 presented,

[0401] xe611 to xe613 can each be understood by referring to the description presented regarding xe1,

[0402] R 611 to R 613 can each be understood by referring to the description presented regarding R 601 presented, and

[0403] R 614 to R 616 can each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

[0404] In one embodiment, L in Formulas 601 and 601-1 601 and L 611 to L613 may be independently selected from:

[0405] a phenylene group, a naphthylene group, a fluorene group, a spiro-bifluorene group, a benzo[a]fluorene group, a dibenzo[a,h]fluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a benzo[a]phenanthrene group, a pyrene group, a chrysene group, a perylene group, a pentacene group, a hexacene group, a quinquacene group, a thiophene group, a furan group, a carbazole group, an indole group, an isoindole group, a benzofuran group, a benzothiophene group, a dibenzofuran group, a dibenzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzosilole group, a pyridine group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a thiadiazole group, an oxadiazole group, a pyrazine group, a pyrimidine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; and

[0406] each independently selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorene group, a spiro-bifluorene group, a benzo[a]fluorene group, a dibenzo[a,h]fluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a benzo[a]phenanthrene group, a pyrene group, At least one of a phenyl group, a perylene group, a pentaphenyl group, a sexiphenyl group, a quaterphenyl group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group substituted phenyl group, naphthylene group, fluorene group, spiro-bifluorene group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, anthryl group, fluoranthenyl group, benzophenanthryl group, pyrenyl group, sub- A phenyl group, a perylene group, a pentaphenyl group, a sexiphenyl group, a quaterphenyl group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group,

[0407] However, the embodiments of the present disclosure are not limited thereto.

[0408] In one or more embodiments, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 may each independently be 0, 1, or 2.

[0409] In one or more embodiments, R in Formula 601 and Formula 601-1 601 and R 611 to R 613 may each independently be selected from:

[0410] phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, anthryl group, fluoranthenyl group, benzo[a]phenanthryl group, pyrenyl group, anthra[2,1,9-def:6,5,10-d'e'f']dithieno[3,2-b:2',3'-d']s-indacenyl group, perylenyl group, pentaphenyl group, hexaphenyl group, quinquephenyl group, thienyl group, furyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridyl group, imidazopyrimidinyl group and azacarbazolyl group;

[0411] each independently being selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 alkyl group, C1-C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, anthryl group, fluoranthenyl group, benzo[a]phenanthryl group, pyrenyl group, a phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorene group, spiro-bifluorene group, benzo[b]fluorene group, dibenzo[b,d]fluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[a]phenanthrene group, pyrene group, substituted by at least one of a radical group, perylene radical group, pentaphenyl group, sexiphenyl group, quaterphenyl group, thiophene radical group, furan radical group, carbazole radical group, indole radical group, isoindole radical group, benzofuran radical group, benzothiophene radical group, dibenzofuran radical group, dibenzothiophene radical group, benzocarbazole radical group, dibenzocarbazole radical group, dibenzosilole radical group, pyridine radical group, imidazole radical group, pyrazole radical group, thiazole radical group, isothiazole radical group, oxazole radical group, isoxazole radical group, thiadiazole radical group, oxadiazole radical group, pyrazine radical group, pyrimidine radical group, pyridazine radical group, triazine radical group, quinoline radical group, isoquinoline radical group, benzoquinoline radical group, phthalazine radical group, naphthyridine radical group, quinoxaline radical group, quinazoline radical group, cinnoline radical group, phenanthridine radical group, acridine radical group, phenanthroline radical group, phenazine radical group, benzimidazole radical group, isobenzothiazole radical group, benzoxazole radical group, isobenzoxazole radical group, triazole radical group, tetrazole radical group, imidazopyridine radical group, imidazopyrimidine radical group, and azacarbazole radical group a radical group, perylene radical group, pentaphenyl group, sexiphenyl group, quaterphenyl group, thiophene radical group, furan radical group, carbazole radical group, indole radical group, isoindole radical group, benzofuran radical group, benzothiophene radical group, dibenzofuran radical group, dibenzothiophene radical group, benzocarbazole radical group, dibenzocarbazole radical group, dibenzosilole radical group, pyridine radical group, imidazole radical group, pyrazole radical group, thiazole radical group, isothiazole radical group, oxazole radical group, isoxazole radical group, thiadiazole radical group, oxadiazole radical group, pyrazine radical group, pyrimidine radical group, pyridazine radical group, triazine radical group, quinoline radical group, isoquinoline radical group, benzoquinoline radical group, phthalazine radical group, naphthyridine radical group, quinoxaline radical group, quinazoline radical group, cinnoline radical group, phenanthridine radical group, acridine radical group, phenanthroline radical group, phenazine radical group, benzimidazole radical group, isobenzothiazole radical group, benzoxazole radical group, isobenzoxazole radical group, triazole radical group, tetrazole radical group, imidazopyridine radical group, imidazopyrimidine radical group, and azacarbazole radical group; and

[0412] -S(=O)2(Q 601 ), and -P(=O)(Q 601 )(Q 602 ), and

[0413] Q 601 and Q 602 can each independently be the same as those described above.

[0414] The electron transport region may include at least one compound selected from Compound ET1 to Compound ET36, but the embodiments of the present disclosure are not limited thereto:

[0415]

[0416]

[0417]

[0418]

[0419] In one or more embodiments, the electron transport region may include at least one compound selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ:

[0420]

[0421] The buffer layer, hole blocking layer, and electron control layer may each have a thickness of about to about (e.g., about to about ). When the thicknesses of the buffer layer, hole blocking layer, and electron control layer are each within these ranges, the hole blocking layer and electron control layer may each have excellent hole blocking characteristics and electron control characteristics without a significant increase in the driving voltage.

[0422] The electron transport layer may have a thickness of about to about (e.g., about to about ). When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a significant increase in the driving voltage.

[0423] In addition to the materials described above, the electron transport region (e.g., the electron transport layer in the electron transport region) may further include a metal-containing material.

[0424] The metal-containing material may include at least one selected from alkali metal complexes and alkaline earth metal complexes. The alkali metal complex may contain metal ions selected from lithium (Li) ions, sodium (Na) ions, potassium (K) ions, rubidium (Rb) ions, and cesium (Cs) ions, and the alkaline earth metal complex may contain metal ions selected from beryllium (Be) ions, magnesium (Mg) ions, calcium (Ca) ions, strontium (Sr) ions, and barium (Ba) ions. The ligand coordinated to the metal ions of the alkali metal complex or alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.

[0425] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium hydroxyquinoline, LiQ) or compound ET-D2:

[0426]

[0427] The electron transport region may include an electron injection layer to facilitate electron injection from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.

[0428] The electron injection layer may have i) a single-layer structure including a single layer containing a single material, ii) a single-layer structure including a single layer containing a plurality of different materials, or iii) a multi-layer structure having a plurality of layers containing a plurality of different materials.

[0429] The electron injection layer may contain an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0430] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal may be Li, Na, or Cs. In one or more than one embodiment, the alkali metal may be Li or Cs, but the embodiments of the present disclosure are not limited thereto.

[0431] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

[0432] The rare earth metal may be selected from scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb), and gadolinium (Gd).

[0433] The alkali metal compounds, alkaline earth metal compounds, and rare earth metal compounds may be selected from oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of alkali metals, alkaline earth metals, and rare earth metals.

[0434] The alkali metal compounds may be selected from alkali metal oxides (e.g., Li2O, Cs2O, and / or K2O) and alkali metal halides (e.g., LiF, NaF, CsF, KF, LiI, NaI, CsI, and / or KI). In one embodiment, the alkali metal compounds may be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, but the embodiments of the present disclosure are not limited thereto.

[0435] The alkaline earth metal compounds may be selected from alkaline earth metal oxides (e.g., BaO, SrO, CaO, Ba x Sr 1-x O(0 < x < 1) and / or Ba x Ca 1-x O(0 < x < 1)). In one embodiment, the alkaline earth metal compounds may be selected from BaO, SrO, and CaO, but the embodiments of the present disclosure are not limited thereto.

[0436] The rare earth metal compounds may be selected from YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, and TbF3. In one embodiment, the rare earth metal compounds may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but the embodiments of the present disclosure are not limited thereto.

[0437] The alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may respectively contain metal ions selected from alkali metals, alkaline earth metals, and rare earth metals as described above, and the ligands coordinated with the metal ions of the alkali metal complexes, alkaline earth metal complexes, or rare earth metal complexes may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.

[0438] The electron injection layer may include the following (e.g., consist of the following): an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described above. In one or more embodiments, the electron injection layer may further comprise an organic material. When the electron injection layer further comprises an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or a combination thereof may be uniformly or non-uniformly dispersed in a matrix comprising the organic material.

[0439] The electron injection layer may have a thickness of about to about (e.g., about to about ). When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics can be obtained without a significant increase in the driving voltage.

[0440] [Second electrode 190]

[0441] The second electrode 190 may be disposed on the organic layer 150 having the structure described above. The second electrode 190 may be a cathode, which is an electron injection electrode, and in this regard, the material used to form the second electrode 190 may be selected from metals, alloys, conductive compounds, and combinations thereof each having a relatively low work function.

[0442] The second electrode 190 may comprise at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, and IZO, but the embodiments of the present disclosure are not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0443] The second electrode 190 may have a single-layer structure, or a multi-layer structure including two or more layers.

[0444] Figures 2 to 4 description]

[0445] Figure 2 is a schematic diagram of an organic light-emitting device 20 according to an embodiment. The organic light-emitting device 20 includes a first cover layer 210, a first electrode 110, an organic layer 150, and a second electrode 190, which are sequentially stacked in this prescribed order. Figure 3 ​FIG. 0 is a schematic view of an organic light-emitting device 30 according to an embodiment. The organic light-emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second cover layer 220, which are sequentially stacked in this specified order. Figure 4 FIG. 1 is a schematic view of an organic light-emitting device 40 according to an embodiment. The organic light-emitting device 40 includes a first cover layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second cover layer 220, which are sequentially stacked in this specified order.

[0446] Regarding Figures 2 to 4 , the first electrode 110, the organic layer 150, and the second electrode 190 can each be understood by referring to the descriptions presented regarding Figure 1 presented.

[0447] In the organic layer 150 of each of the organic light-emitting devices 20 and 40, the light generated in the emission layer can pass through the first electrode 110 and the first cover layer 210 toward the outside, where the first electrode 110 is a semi-transmissive electrode or a transmissive electrode. In the organic layer 150 of each of the organic light-emitting devices 30 and 40, the light generated in the emission layer can pass through the second electrode 190 and the second cover layer 220 toward the outside, where the second electrode 190 is a semi-transmissive electrode or a transmissive electrode.

[0448] The first cover layer 210 and the second cover layer 220 can increase the external light-emitting efficiency of the device according to the principle of constructive interference.

[0449] The first cover layer 210 and the second cover layer 220 can each independently be an organic cover layer containing an organic material, an inorganic cover layer containing an inorganic material, or a composite cover layer containing an organic material and an inorganic material.

[0450] At least one selected from the first cover layer 210 and the second cover layer 220 can each independently contain at least one material selected from carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds, and amine-based compounds can optionally be substituted with substituents containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one selected from the first cover layer 210 and the second cover layer 220 can each independently contain a heterocyclic compound.

[0451] In one embodiment, at least one selected from the first cover layer 210 and the second cover layer 220 can each independently contain a compound represented by Formula 201 or a compound represented by Formula 202.

[0452] In one or more embodiments, at least one selected from the first cover layer 210 and the second cover layer 220 may each independently include a compound selected from Compound HT28 to Compound HT33 and Compound CP1 to Compound CP5, but the embodiments of the present disclosure are not limited thereto.

[0453]

[0454] Above, an organic light emitting device according to an embodiment has been described, but the embodiments of the present disclosure are not limited thereto. Figures 1 to 4 The layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region may each be formed in a certain (e.g., set or predetermined) region using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.

[0455] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, depending on the material to be included in the layer and the structure of the layer to be formed, the deposition may be performed at a deposition temperature of about 100 °C to about 500 °C, a vacuum degree of about 10

[0456] Torr to about 10 -8 Torr and a deposition rate of about -3 Torr to about to about .

[0457] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by spin coating, depending on the material to be included in the layer and the structure of the layer to be formed, the spin coating may be performed at a coating rate of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80 °C to about 200 °C.

[0458] [Device]

[0459] The organic light emitting device may be included in any suitable device. For example, the device may be a light emitting device, a verification device, or an electronic device.

[0460] In addition to the organic light emitting device, the light emitting device may further include a thin film transistor. Here, the thin film transistor may include a source electrode, an active layer, and a drain electrode, wherein the first electrode of the organic light emitting device may be electrically connected to the source electrode or the drain electrode of the thin film transistor. The light emitting device may be used in various suitable displays, light sources, etc.

[0461] The verification device may be, for example, a biometric verification device for verifying an individual using biometric information of a biometric body (e.g., a fingertip, a pupil, etc.).

[0462] In addition to the organic light-emitting device, the verification device may further include a biometric information collector.

[0463] The electronic device may be applied to a personal computer (e.g., a mobile personal computer), a mobile phone, a digital camera, an electronic notepad, an electronic dictionary, an electronic game console, a medical instrument (e.g., an electronic thermometer, a sphygmomanometer, a blood glucose meter, a pulse measuring device, a pulse wave measuring device, an electrocardiogram (ECG) monitor, an ultrasonic diagnostic device, or an endoscope monitor), a fish finder, various measuring instruments, meters (e.g., meters for vehicles, aircraft, and ships), a projector, etc., but the embodiments of the present disclosure are not limited thereto.

[0464] [General Definition of Substituents]

[0465] As used herein, the term "C1-C 60 alkyl group" refers to a straight-chain or branched-chain aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, and a hexyl group. In some embodiments, the C1-C 60 alkyl group may be a C1-C 30 alkyl group, a C1-C 20 alkyl group, or a C1-C 10 alkyl group. As used herein, the term "C1-C 60 alkylene group" refers to a divalent group having a structure substantially the same as that of the C1-C 60 alkyl group.

[0466] As used herein, the term "C2-C 60 alkenyl group" refers to a hydrocarbon group having at least one carbon-carbon double bond in the middle or at the end of the C2-C 60 alkyl group, and non-limiting examples thereof include a vinyl group, an allyl group, and a butenyl group. In some embodiments, the C2-C 60 alkenyl group may be a C2-C 30 alkenyl group, a C2-C 20 alkenyl group, or a C2-C 10 alkenyl group. As used herein, the term "C2-C 60 alkenylene group" refers to a divalent group having a structure substantially the same as that of the C2-C 60 alkenyl group.

[0467] As used herein, the term "C2-C 60 alkynyl group" refers to a group in which there is at least one carbon-carbon triple bond in the middle or at the end of the C2-C 60A hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the end of the alkyl group, and non-limiting examples thereof include ethynyl group and propargyl group. In some embodiments, C2-C 60 The alkynyl group can be C2-C 30 alkynyl group, C2-C 20 alkynyl group or C2-C 10 alkynyl group. As used herein, the term "C2-C 60 alkynylene group" refers to a divalent group having substantially the same structure as the C2-C 60 alkynyl group.

[0468] As used herein, the term "C1-C 60 alkoxy group" refers to a monovalent group represented by -OA 101 (where A 101 is a C1-C 60 alkyl group), and non-limiting examples thereof include methoxy group, ethoxy group and isopropoxy group.

[0469] As used herein, the term "C3-C 10 cycloalkyl group" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and cycloheptyl group. As used herein, the term "C3-C 10 cycloalkylene group" refers to a divalent group having substantially the same structure as the C3-C 10 cycloalkyl group.

[0470] As used herein, the term "C1-C 10 heterocycloalkyl group" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as ring-forming atoms (e.g., 1 to 5 or 1 to 3 atoms, e.g., 1, 2, 3, 4 or 5 heteroatoms) and 1 to 10 carbon atoms, and non-limiting examples thereof include 1,2,3,4-oxadiazolyl group, tetrahydrofuryl group and tetrahydrothienyl group. As used herein, the term "C1-C 10 heterocycloalkylene group" refers to a divalent group having substantially the same structure as the C1-C 10 heterocycloalkyl group.

[0471] As used herein, the term "C3-C 10 cycloalkenyl group" refers to a monovalent monocyclic group having 3 to 10 carbon atoms, at least one carbon-carbon double bond and no aromaticity in its ring, and non-limiting examples thereof include cyclopentenyl group, cyclohexenyl group and cycloheptenyl group. As used herein, the term "C3-C 10"Subcycloalkenyl group" means a divalent group having a structure substantially the same as that of a C3-C 10 cycloalkenyl group.

[0472] As used herein, the term "C1-C 10 heterocycloalkenyl group" means a monovalent monocyclic group having in its ring at least one heteroatom selected from N, O, Si, P, and S (e.g., 1 to 5 or 1 to 3 atoms, e.g., 1, 2, 3, 4, or 5 heteroatoms), 1 to 10 carbon atoms, and at least one double bond. C1-C 10 Non-limiting examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxadiazolyl groups, 2,3-dihydrofuranyl groups, and 2,3-dihydrothienyl groups. As used herein, the term "C1-C 10 subheterocycloalkenyl group" means a divalent group having a structure substantially the same as that of a C1-C 10 heterocycloalkenyl group.

[0473] As used herein, the term "C6-C 60 aryl group" means a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms, and as used herein, the term "C6-C 60 arylene group" means a divalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms. C6-C 60 Non-limiting examples of aryl groups include phenyl groups, naphthyl groups, anthracenyl groups, phenanthryl groups, pyrenyl groups, and yl groups. In some embodiments, the C6-C 60 aryl group can be a C6-C 30 aryl group, a C6-C 24 aryl group, or a C6-C 18 aryl group. When the C6-C 60 aryl group or the C6-C 60 arylene group contains two or more rings, the rings can be fused to each other.

[0474] As used herein, the term "C1-C 60 heteroaryl group" means a monovalent group having a carbocyclic aromatic system containing, in addition to 1 to 60 carbon atoms, at least one heteroatom selected from N, O, Si, P, and S (e.g., 1 to 5 or 1 to 3 atoms, e.g., 1, 2, 3, 4, or 5 heteroatoms) as a ring-forming atom. As used herein, the term "C1-C 60"Hetarylene group" refers to a divalent group of a carbocyclic aromatic system having at least one heteroatom selected from N, O, Si, P, and S (e.g., 1 to 5 or 1 to 3 atoms, e.g., 1, 2, 3, 4, or 5 heteroatoms) in addition to 1 to 60 carbon atoms as ring-forming atoms. C1-C 60 Non-limiting examples of heteroaryl groups include pyridyl groups, pyrimidinyl groups, pyrazinyl groups, pyridazinyl groups, triazinyl groups, quinolinyl groups, and isoquinolinyl groups. In some embodiments, C1-C 60 The heteroaryl group can be a C1-C 30 heteroaryl group, a C1-C 24 heteroaryl group, or a C1-C 18 heteroaryl group. When the C1-C 60 heteroaryl group and the C1-C 60 hetarylene group contain two or more than two rings, the rings can be fused to each other.

[0475] As used herein, the term "C6-C 60 aryloxy group" refers to -OA 102 (where A 102 is a C6-C 60 aryl group), and as used herein, the term "C6-C 60 arylthio group" refers to -SA 103 (where A 103 is a C6-C 60 aryl group).

[0476] As used herein, the term "monovalent non-aromatic fused polycyclic group" refers to a monovalent group (e.g., having 8 to 60 carbon atoms, e.g., 8 to 30 or 8 to 24 carbon atoms) having two or more than two rings fused to each other, having only carbon atoms as ring-forming atoms, and not having aromaticity in its entire molecular structure. Non-limiting examples of monovalent non-aromatic fused polycyclic groups are fluorenyl groups. As used herein, the term "divalent non-aromatic fused polycyclic group" refers to a divalent group having substantially the same structure as the monovalent non-aromatic fused polycyclic group.

[0477] As used herein, the term "monovalent non-aromatic fused heteropolycyclic group" refers to a monovalent group (e.g., having 1 to 60 carbon atoms, such as 1 to 30 or 1 to 24 carbon atoms) that has two or more rings fused to each other, has at least one heteroatom selected from N, O, Si, P, and S (e.g., 1 to 5 or 1 to 3 atoms, such as 1, 2, 3, 4, or 5 heteroatoms) as ring-forming atoms, and does not have aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic fused heteropolycyclic group are carbazolyl groups. As used herein, the term "divalent non-aromatic fused heteropolycyclic group" refers to a divalent group having a structure substantially the same as that of the monovalent non-aromatic fused heteropolycyclic group.

[0478] As used herein, the term "C5-C 60 carbocyclic group" refers to a monocyclic group or polycyclic group having 5 to 60 carbon atoms, wherein the ring-forming atoms are only carbon atoms. As used herein, the term "C5-C 60 carbocyclic group" refers to an aromatic carbocyclic group or a non-aromatic carbocyclic group. The C5-C 60 carbocyclic group can be a ring (e.g., benzene), a monovalent group (e.g., phenyl group), or a divalent group (e.g., phenylene group). In one or more embodiments, depending on the number of substituents attached to the C5-C 60 carbocyclic group, the C5-C 60 carbocyclic group can be a trivalent group or a tetravalent group. In some embodiments, the C5-C 60 carbocyclic group can be a C5-C 30 carbocyclic group, a C5-C 24 carbocyclic group, or a C5-C 18 carbocyclic group.

[0479] As used herein, the term "C1-C 60 heterocyclic group" refers to a group having a structure substantially the same as that of the C5-C 60 carbocyclic group, but in addition to carbon (the number of carbon atoms can be 1 to 60, such as 1 to 30 or 1 to 24 carbon atoms), at least one heteroatom selected from N, O, Si, P, and S (e.g., 1 to 5 or 1 to 3 atoms, such as 1, 2, 3, 4, or 5 heteroatoms) is used as a ring-forming atom.

[0480] In this specification, substituted C5-C 60 carbocyclic groups, substituted C1-C 60 heterocyclic groups, substituted C3-C 10 subcycloalkyl groups, substituted C1-C 10 subheterocycloalkyl groups, substituted C3-C 10 subcycloalkenyl groups, substituted C1-C10 Azacycloalkenyl group, substituted C6-C 60 Arylene group, substituted C1-C 60 Heteroarylene group, substituted divalent non-aromatic fused polycyclic group, substituted divalent non-aromatic fused heteropolycyclic group, substituted C1-C 60 Alkyl group, substituted C2-C 60 Alkenyl group, substituted C2-C 60 Alkynyl group, substituted C1-C6 alkoxy group, substituted C3-C 10 Cycloalkyl group, substituted C1-C 10 Heterocycloalkyl group, substituted C3-C 10 Cycloalkenyl group, substituted C1-C 10 Heterocycloalkenyl group, substituted C6-C 60 Aryl group, substituted C6-C 60 Aryloxy group, substituted C6-C 60 Arylthio group, substituted C1-C 60 At least one substituent of the heteroaryl group, substituted monovalent non-aromatic fused polycyclic group, and substituted monovalent non-aromatic fused heteropolycyclic group may be selected from:

[0481] Deuterium, -F, -Cl, -Br, -I, hydroxy group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 60 Alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group and C1-C 60 Alkoxy group;

[0482] Each independently selected from deuterium, -F, -Cl, -Br, -I, hydroxy group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11)(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 ) and -P(=O)(Q 11 )(Q 12 ) at least one substituted C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups and C1-C 60 Alkoxy groups;

[0483] C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;

[0484] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 ) and -P(=O)(Q21 )(Q 22 ) in at least one substituted C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C1-C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group; and

[0485] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ), and

[0486] Q 11 to Q 13 、Q 21 to Q 23 and Q 31 to Q 33 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazone group, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C1-C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, biphenyl group and terphenyl group.

[0487] As used herein, the term "Ph" refers to a phenyl group, the term "Me" refers to a methyl group, the term "Et" refers to an ethyl group, and the term "ter-Bu" or "Bu t " refers to a tert-butyl group, and the term "OMe" refers to a methoxy group as used herein.

[0488] As used herein, the term "biphenyl group" may refer to "a phenyl group substituted with a phenyl group". In other words, a "biphenyl group" is a substituted phenyl group having a C6-C 60 aryl group (phenyl group) as a substituent.

[0489] As used herein, the term "terphenyl group" may refer to "a phenyl group substituted with a biphenyl group". In other words, a "terphenyl group" is a substituted phenyl group having a C6-C 60 aryl group substituted with a C6-C 60 aryl group (biphenyl group) as a substituent.

[0490] As used herein, unless otherwise defined, each of * and *' refers to a bonding site to an adjacent atom in the corresponding formula.

[0491] Hereinafter, the compounds according to the embodiments and the organic light-emitting devices according to the embodiments will be described in more detail with reference to Synthesis Examples and Examples. The expression "using B in place of A" used in the description of the Synthesis Examples means using an equimolar equivalent of B in place of A.

[0492] [Examples]

[0493]

[0494] Synthesis of Intermediate C(1)-1:

[0495] 1-Bromo-6-chlorodibenz[b,d]furan (C(1)-2, 2.81 g, 1 equivalent) was dissolved in tetrahydrofuran (THF) and stirred at a temperature of -78 °C. After 30 minutes, 1 equivalent of n-BuLi was added dropwise thereto and stirred for 1 hour. Benzoyl chloride (1.4 g, 1 equivalent) was added dropwise thereto and stirred for 4 hours. The reaction was quenched with dilute hydrochloric acid, and it was extracted with dichloromethane (MC). 1.8 g of Intermediate C(1)-1 was obtained by column separation. (Yield: 60%).

[0496] Synthesis of Intermediate C(1):

[0497] Dissolve 2-bromo-1,1'-biphenyl (1.4 g, 1 equivalent) in THF and stir at a temperature of -78 °C. After 30 minutes, add 1 equivalent of n-BuLi dropwise thereto and stir for 1 hour. Add intermediate C(1)-1 (1.8 g, 1 equivalent) dropwise thereto and stir for 3 hours. Quench the reaction with dilute hydrochloric acid and extract it with MC. 1 g of intermediate C(1) was obtained by column separation. (Yield: 40%).

[0498] Synthesis of intermediate C(2):

[0499] Intermediate C(2) was synthesized in substantially the same manner as in the synthesis of intermediate C(1), except that 3-bromo-6-chlorodibenz[b,d]furan was used instead of compound C(1)-2.

[0500] Synthesis of intermediate C(3):

[0501] Intermediate C(3) was synthesized in substantially the same manner as in the synthesis of intermediate C(1), except that 4-bromo-6-chlorodibenz[b,d]furan was used instead of compound C(1)-2.

[0502] Synthesis of intermediate C(4):

[0503] Intermediate C(4) was synthesized in substantially the same manner as in the synthesis of intermediate C(1), except that 1-bromo-7-chlorodibenz[b,d]furan was used instead of compound C(1)-2.

[0504] Synthesis of intermediate C(5):

[0505] Intermediate C(5) was synthesized in substantially the same manner as in the synthesis of intermediate C(1), except that 3-bromo-7-chlorodibenz[b,d]furan was used instead of compound C(1)-2.

[0506] Synthesis of intermediate C(6):

[0507] Intermediate C(6) was synthesized in substantially the same manner as in the synthesis of intermediate C(1), except that 4-bromo-7-chlorodibenz[b,d]furan was used instead of compound C(1)-2.

[0508] Synthesis of intermediate C(7):

[0509] Intermediate C(7) was synthesized in substantially the same manner as in the synthesis of intermediate C(1), except that 1-bromo-8-chlorodibenz[b,d]furan was used instead of compound C(1)-2.

[0510] Synthesis of intermediate C(8):

[0511] Intermediate C(8) was synthesized in substantially the same manner as in the synthesis of intermediate C(1), except that 3-bromo-8-chlorodibenz[b,d]furan was used in place of compound C(1)-2.

[0512] Synthesis of intermediate C(9):

[0513] Intermediate C(9) was synthesized in substantially the same manner as in the synthesis of intermediate C(1), except that 4-bromo-8-chlorodibenz[b,d]furan was used in place of compound C(1)-2.

[0514] Synthesis Example 1: Synthesis of Compound 1

[0515]

[0516] Intermediate C(1) (1 g, 1 equivalent), diphenylamine (0.42 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalents), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-neck round-bottom flask and stirred at 90 °C for 3 hours. The mixture was worked up with MC / H2O and 0.96 g of compound 1 was obtained by column separation. (Yield: 74%).

[0517] Synthesis Example 2: Synthesis of Compound 2

[0518]

[0519] Intermediate C(1) (1 g, 1 equivalent), N-phenylnaphthalen-1-amine (0.54 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalents), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-neck round-bottom flask and stirred at 90 °C for 3 hours. The mixture was worked up with MC / H2O and 0.99 g of compound 2 was obtained by column separation. (Yield: 70%).

[0520] Synthesis Example 3: Synthesis of Compound 6

[0521]

[0522] Intermediate C(1) (1 g, 1 equivalent), 9,9-dimethyl-N-phenyl-9H-fluoren-4-amine (0.71 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalent), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-necked round-bottom flask and stirred at 90 °C for 3 h. The mixture was worked up with MC / H2O and 1.06 g of compound 6 was obtained by column separation. (Yield: 68%).

[0523] Synthesis Example 4: Synthesis of Compound 13

[0524]

[0525] Intermediate C(2) (1 g, 1 equivalent), diphenylamine (0.42 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalent), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-necked round-bottom flask and stirred at 90 °C for 3 h. The mixture was worked up with MC / H2O and 0.99 g of compound 13 was obtained by column separation. (Yield: 77%).

[0526] Synthesis Example 5: Synthesis of Compound 14

[0527]

[0528] Intermediate C(2) (1 g, 1 equivalent), N-phenylnaphthalen-1-amine (0.54 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalent), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-necked round-bottom flask and stirred at 90 °C for 3 h. The mixture was worked up with MC / H2O and 0.93 g of compound 14 was obtained by column separation. (Yield: 66%).

[0529] Synthesis Example 6: Synthesis of Compound 18

[0530]

[0531] Intermediate C(2) (1 g, 1 equivalent), 9,9-dimethyl-N-phenyl-9H-fluoren-4-amine (0.71 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalent), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-necked round-bottom flask and stirred at 90 °C for 3 h. The mixture was worked up with MC / H2O and 1.1 g of compound 18 was obtained by column separation. (Yield: 71%).

[0532] Synthesis Example 7: Synthesis of Compound 25

[0533]

[0534] Intermediate C(3) (1 g, 1 equivalent), diphenylamine (0.42 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalent), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-necked round-bottom flask and stirred at 90 °C for 3 h. The mixture was worked up with MC / H2O and 0.99 g of compound 25 was obtained by column separation. (Yield: 77%).

[0535] Synthesis Example 8: Synthesis of Compound 26

[0536]

[0537] Intermediate C(3) (1 g, 1 equivalent), N-phenylnaphthalen-1-amine (0.54 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalent), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-necked round-bottom flask and stirred at 90 °C for 3 h. The mixture was worked up with MC / H2O and 0.83 g of compound 26 was obtained by column separation. (Yield: 59%).

[0538] Synthesis Example 9: Synthesis of Compound 30

[0539]

[0540] Intermediate C(3) (1 g, 1 equivalent), 9,9-dimethyl-N-phenyl-9H-fluoren-4-amine (0.71 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalent), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-neck round-bottom flask and stirred at 90 °C for 3 h. The mixture was worked up with MC / H2O and 1.13 g of compound 30 was obtained by column separation. (Yield: 73%).

[0541] Synthesis Example 10: Synthesis of Compound 37

[0542]

[0543] Intermediate C(4) (1 g, 1 equivalent), diphenylamine (0.42 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalent), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-neck round-bottom flask and stirred at 90 °C for 3 h. The mixture was worked up with MC / H2O and 1.03 g of compound 37 was obtained by column separation. (Yield: 80%).

[0544] Synthesis Example 11: Synthesis of Compound 38

[0545]

[0546] Intermediate C(4) (1 g, 1 equivalent), N-phenylnaphthalen-1-amine (0.54 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalent), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-neck round-bottom flask and stirred at 90 °C for 3 h. The mixture was worked up with MC / H2O and 0.99 g of compound 38 was obtained by column separation. (Yield: 70%).

[0547] Synthesis Example 12: Synthesis of Compound 42

[0548]

[0549] Intermediate C(4) (1 g, 1 equiv), 9,9-dimethyl-N-phenyl-9H-fluoren-4-amine (0.71 g, 1.1 equiv), Pd2(dba)3 (0.1 g, 0.05 equiv), t-BuONa (0.65 g, 3 equiv), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-neck round-bottom flask and stirred at 90 °C for 3 h. The mixture was worked up with MC / H2O and 1.01 g of compound 42 was obtained by column separation. (Yield: 65%).

[0550] Synthesis Example 13: Synthesis of Compound 49

[0551]

[0552] Intermediate C(5) (1 g, 1 equiv), diphenylamine (0.42 g, 1.1 equiv), Pd2(dba)3 (0.1 g, 0.05 equiv), t-BuONa (0.65 g, 3 equiv), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-neck round-bottom flask and stirred at 90 °C for 3 h. The mixture was worked up with MC / H2O and 0.95 g of compound 49 was obtained by column separation. (Yield: 74%).

[0553] Synthesis Example 14: Synthesis of Compound 50

[0554]

[0555] Intermediate C(5) (1 g, 1 equiv), N-phenylnaphthalen-1-amine (0.54 g, 1.1 equiv), Pd2(dba)3 (0.1 g, 0.05 equiv), t-BuONa (0.65 g, 3 equiv), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-neck round-bottom flask and stirred at 90 °C for 3 h. The mixture was worked up with MC / H2O and 0.97 g of compound 50 was obtained by column separation. (Yield: 70%).

[0556] Synthesis Example 15: Synthesis of Compound 54

[0557]

[0558] Intermediate C(5) (1 g, 1 equivalent), 9,9-dimethyl-N-phenyl-9H-fluoren-4-amine (0.71 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalent), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-neck round-bottom flask and stirred at 90 °C for 3 h. The mixture was worked up with MC / H2O and 1.1 g of compound 54 was obtained by column separation. (Yield: 71%).

[0559] Synthesis Example 16: Synthesis of Compound 61

[0560]

[0561] Intermediate C(6) (1 g, 1 equivalent), diphenylamine (0.42 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalent), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-neck round-bottom flask and stirred at 90 °C for 3 h. The mixture was worked up with MC / H2O and 0.92 g of compound 61 was obtained by column separation. (Yield: 72%).

[0562] Synthesis Example 17: Synthesis of Compound 62

[0563]

[0564] Intermediate C(6) (1 g, 1 equivalent), N-phenylnaphthalen-1-amine (0.54 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalent), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-neck round-bottom flask and stirred at 90 °C for 3 h. The mixture was worked up with MC / H2O and 0.88 g of compound 62 was obtained by column separation. (Yield: 64%).

[0565] Synthesis Example 18: Synthesis of Compound 66

[0566]

[0567] Intermediate C(6) (1 g, 1 equiv), 9,9-dimethyl-N-phenyl-9H-fluoren-4-amine (0.71 g, 1.1 equiv), Pd2(dba)3 (0.1 g, 0.05 equiv), t-BuONa (0.65 g, 3 equiv), t-Bu3P (0.08 mL) and toluene (50 mL) were added to a single-neck round-bottom flask and stirred at 90 °C for 3 h. The mixture was worked up with MC / H2O and 1.07 g of compound 66 was obtained by column separation. (Yield: 69%).

[0568] Synthesis Example 19: Synthesis of Compound 73

[0569]

[0570] Intermediate C(7) (1 g, 1 equiv), diphenylamine (0.42 g, 1.1 equiv), Pd2(dba)3 (0.1 g, 0.05 equiv), t-BuONa (0.65 g, 3 equiv), t-Bu3P (0.08 mL) and toluene (50 mL) were added to a single-neck round-bottom flask and stirred at 90 °C for 3 h. The mixture was worked up with MC / H2O and 1.03 g of compound 73 was obtained by column separation. (Yield: 80%).

[0571] Synthesis Example 20: Synthesis of Compound 74

[0572]

[0573] Intermediate C(7) (1 g, 1 equiv), N-phenylnaphthalen-1-amine (0.54 g, 1.1 equiv), Pd2(dba)3 (0.1 g, 0.05 equiv), t-BuONa (0.65 g, 3 equiv), t-Bu3P (0.08 mL) and toluene (50 mL) were added to a single-neck round-bottom flask and stirred at 90 °C for 3 h. The mixture was worked up with MC / H2O and 1.02 g of compound 74 was obtained by column separation. (Yield: 72%).

[0574] Synthesis Example 21: Synthesis of Compound 78

[0575]

[0576] Intermediate C(7) (1 g, 1 equivalent), 9,9-dimethyl-N-phenyl-9H-fluoren-4-amine (0.71 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalent), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-neck round-bottom flask and stirred at 90 °C for 3 hours. The mixture was worked up with MC / H2O and 1.08 g of compound 78 was obtained by column separation. (Yield: 70%).

[0577] Synthesis Example 22: Synthesis of Compound 85

[0578]

[0579] Intermediate C(8) (1 g, 1 equivalent), diphenylamine (0.42 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalent), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-neck round-bottom flask and stirred at 90 °C for 3 hours. The mixture was worked up with MC / H2O and 1.01 g of compound 85 was obtained by column separation. (Yield: 79%).

[0580] Synthesis Example 23: Synthesis of Compound 86

[0581]

[0582] Intermediate C(8) (1 g, 1 equivalent), N-phenylnaphthalen-1-amine (0.54 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalent), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-neck round-bottom flask and stirred at 90 °C for 3 hours. The mixture was worked up with MC / H2O and 0.97 g of compound 86 was obtained by column separation. (Yield: 69%).

[0583] Synthesis Example 24: Synthesis of Compound 89

[0584]

[0585] Intermediate C(8) (1 g, 1 equivalent), 9,9-dimethyl-N-phenyl-9H-fluoren-4-amine (0.71 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalent), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-neck round-bottom flask and stirred at 90 °C for 3 hours. The mixture was worked up with MC / H2O and 1.1 g of compound 89 was obtained by column separation. (Yield: 71%).

[0586] Synthesis Example 25: Synthesis of Compound 97

[0587]

[0588] Intermediate C(9) (1 g, 1 equivalent), diphenylamine (0.42 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalent), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-neck round-bottom flask and stirred at 90 °C for 3 hours. The mixture was worked up with MC / H2O and 0.99 g of compound 97 was obtained by column separation. (Yield: 77%).

[0589] Synthesis Example 26: Synthesis of Compound 98

[0590]

[0591] Intermediate C(9) (1 g, 1 equivalent), N-phenylnaphthalen-1-amine (0.54 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalent), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-neck round-bottom flask and stirred at 90 °C for 3 hours. The mixture was worked up with MC / H2O and 0.83 g of compound 98 was obtained by column separation. (Yield: 59%).

[0592] Synthesis Example 27: Synthesis of Compound 102

[0593]

[0594] Intermediate C(9) (1 g, 1 equivalent), 9,9-dimethyl-N-phenyl-9H-fluoren-4-amine (0.71 g, 1.1 equivalents), Pd2(dba)3 (0.1 g, 0.05 equivalent), t-BuONa (0.65 g, 3 equivalents), t-Bu3P (0.08 mL), and toluene (50 mL) were added to a single-necked round-bottom flask and stirred at 90 °C for 3 hours. The mixture was worked up with MC / H2O and 1.13 g of Compound 102 was obtained by column separation. (Yield: 73%).

[0595] For the compounds synthesized according to Synthesis Examples 1 to 27 1 1H NMR and MS / FAB are shown in Table 1.

[0596] By referring to the synthesis mechanism and source materials described above, those of ordinary skill in the art can readily recognize the synthesis methods of compounds other than those shown in Table 1.

[0597] [Table 1]

[0598]

[0599]

[0600] Example 1

[0601] As the anode, Corning 15 Ω / cm 2 ITO glass substrates were cut into a size of 50 mm × 50 mm × 0.7 mm, ultrasonically treated with isopropyl alcohol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes. The ITO glass substrates were provided to a vacuum deposition apparatus.

[0602] 2-TNATA was vacuum deposited on the ITO glass substrate to form a hole injection layer with a thickness, and a hole transporting compound (Compound 1) was vacuum deposited on the hole injection layer to form a hole transporting layer with a thickness.

[0603] 9,10-bis(naphthalen-2-yl)anthracene (DNA) and 4,4'-bis[2-(4-(N,N'-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi) were co-deposited on the hole transporting layer at a weight ratio of 98:2 to form an emission layer with a thickness.

[0604] Then, Alq3 was deposited on the emission layer to form a An electron transport layer with a thickness of deposits alkali metal halide LiF on the electron transport layer to form an electron injection layer with a thickness of and deposits Al by vacuum deposition to a thickness of to form a LiF / Al electrode, thereby completing the fabrication of the organic light-emitting device.

[0605]

[0606] Examples 2 to 27 and Comparative Examples 1 to 5

[0607] An organic light-emitting device is fabricated in substantially the same manner as in Example 1, except that the hole transport layer is formed by using the compounds shown in Table 2 to replace Compound 1, respectively.

[0608] Evaluation Example 1

[0609] At a current density of 50 mA / cm 2 , the device performance (driving voltage, luminance, efficiency, and color coordinates) of each of the organic light-emitting devices fabricated according to Examples 1 to 27 and Comparative Examples 1 to 5 is measured, and the amount of time elapsed (half-life) when the luminance is 50% of the initial luminance (100%) is measured at a current density of 100 mA / cm 2 . The results are shown in Table 2.

[0610] Luminance measurement: Power is supplied by a current-voltage meter (Keithley SMU236), and the luminance is measured using a luminance meter PR650.

[0611] Efficiency measurement: Power is supplied by a current-voltage meter (Keithley SMU236), and the efficiency is measured using a luminance meter PR650.

[0612] [Table 2]

[0613]

[0614]

[0615]

[0616]

[0617] It is confirmed from Table 2 that when the exemplary compounds are used as the materials for forming the hole transport layer, the organic light-emitting device has excellent characteristics (such as low driving voltage, high luminous efficiency, high luminance, and / or long service life) compared to when using Comparative Examples 1 to 5.

[0618] It should be understood that the embodiments described herein are to be considered in a descriptive sense only and not for purposes of limitation. The description of features or aspects within each embodiment is generally to be considered applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, those of ordinary skill in the art will understand that various changes in form and detail may be made herein without departing from the spirit and scope defined by the claims and their equivalents.

Claims

1. An organic light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer; and at least one heterocyclic compound represented by Formula 1: wherein, in Formula 1, Formula 2-1 and Formula 2-2, X is O or S, Each of R1 to R8 is independently selected from a group represented by Formula 2-1, a group represented by Formula 2-2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), and -P(=O)(Q1)(Q2), one selected from R1, R2, R4, R5, R7 and R8 is a group represented by Formula 2-1, and one selected from R1 to R8 that is not a group represented by Formula 2-1 is a group represented by Formula 2-2, R 11 to R 18 each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxy group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2), Two adjacent groups among R1 to R8 and R 11 to R 18 Two adjacent groups among them are optionally connected to each other to form a ring, Ar1 to Ar3 are each independently a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group, Ar2 and Ar3 are optionally connected to each other via a single bond, -C(Q4)(Q5)-, -Si(Q4)(Q5)-, -O-, -S-, -N(Q4)-, -B(Q4)-, -C(=O)-, -S(=O)2-, -S(=O)(Q4)(Q5)- or -P(=O)(Q4)- to form a fused heterocycle, L 11 to L 13 each independently is a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group, a11 to a13 are each independently an integer from 0 to 3, When a11 is 0, *-(L 11 ) a11 -*' represents a single bond. When a12 is 0, *-(L 12 ) a12 -*' represents a single bond, and when a13 is 0, *-(L 13 ) a13 -*' represents a single bond, The substituted C5-C 60 carbocyclic group, the substituted C1-C 60 heterocyclic group, the substituted C1-C 60 alkyl group, the substituted C2-C 60 alkenyl group, the substituted C2-C 60 alkynyl group, the substituted C1-C 60 alkoxy group, the substituted C3-C 10 cycloalkyl group, the substituted C1-C 10 heterocycloalkyl group, the substituted C3-C 10 cycloalkenyl group, the substituted C1-C 10 heterocycloalkenyl group, the substituted C6-C 60 aryl group, the substituted C6-C 60 aryloxy group, the substituted C6-C 60 arylthio group, the substituted C1-C 60 heteroaryl group, at least one substituent of the substituted monovalent non-aromatic fused polycyclic group and the substituted monovalent non-aromatic fused heteropolycyclic group is selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazone group, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group and C1-C 60 alkoxy group; Each independently selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazone group, C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C1-C 60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ), and -P(=O)(Q 11 )(Q 12 ) and at least one substituted C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, and C1-C 60 alkoxy group; C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C1-C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, biphenyl group and terphenyl group; each independently selected from deuterium, -F, -Cl, -Br, -I, a hydroxy group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C 60 alkyl group, a C2-C 60 alkenyl group, a C2-C 60 alkynyl group, a C1-C 60 alkoxy group, a C3-C 10 cycloalkyl group, a C1-C 10 heterocycloalkyl group, a C3-C 10 cycloalkenyl group, a C1-C 10 heterocycloalkenyl group, a C6-C 60 aryl group, a C6-C 60 aryloxy group, a C6-C 60 arylthio group, a C1-C 60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, a biphenyl group, a terphenyl group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ), and -P(=O)(Q 21 )(Q 22 ), and at least one substituted C3-C 10 cycloalkyl group, a C1-C 10 heterocycloalkyl group, a C3-C 10 cycloalkenyl group, a C1-C 10 heterocycloalkenyl group, a C6-C 60 aryl group, a C6-C 60 aryloxy group, a C6-C 60 arylthio group, a C1-C 60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, a biphenyl group, and a terphenyl group; and -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 )和-P(=O)(Q 31 )(Q 32 ), Q1 to Q5, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxy group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C 60 alkyl group, a C2-C 60 alkenyl group, a C2-C 60 alkynyl group, a C1-C 60 alkoxy group, a C3-C 10 cycloalkyl group, a C1-C 10 heterocycloalkyl group, a C3-C 10 cycloalkenyl group, a C1-C 10 heterocycloalkenyl group, a C6-C 60 aryl group, a C6-C 60 aryl group substituted with a C1-C 60 alkyl group, a C1-C 60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, a biphenyl group and a terphenyl group, and * represents the connection site to the group represented by Formula 1, and *' represents the connection site to an adjacent atom.

2. The organic light-emitting device according to claim 1, wherein: the first electrode is an anode, the second electrode is a cathode, the organic layer contains the at least one heterocyclic compound, the organic layer further includes a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, the hole transport region includes a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer or any combination thereof, and the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer or any combination thereof.

3. The organic light-emitting device according to claim 2, wherein the hole transport region contains the at least one heterocyclic compound.

4. The organic light-emitting device according to claim 2, wherein the hole transport region includes a hole transport layer, and the hole transport layer contains the at least one heterocyclic compound.

5. The organic light-emitting device according to claim 2, wherein: the hole transport region contains a p-dopant, and the p-dopant has a lowest unoccupied molecular orbital energy level of -3.5 eV or less than -3.5 eV.

6. The organic light-emitting device according to claim 1, wherein the emission layer contains at least one compound selected from styrene-based compounds, anthracene-based compounds, pyrene-based compounds, spiro-difluorene-based compounds, carbazole-based compounds, benzimidazole-based compounds, phosphine oxide-based compounds, dibenzofuran-based compounds, silicon-based compounds and triazine-based compounds.

7. The organic light-emitting device according to claim 1, wherein: the emission layer is a first emission layer for emitting first color light, the organic light-emitting device further includes between the first electrode and the second electrode i) at least one second emission layer for emitting second color light, or ii) at least one second emission layer for emitting second color light and at least one third emission layer for emitting third color light, The maximum emission wavelength of the first color light, the maximum emission wavelength of the second color light, and the maximum emission wavelength of the third color light are the same as or different from each other, and the first color light and the second color light are emitted in the form of a mixed light, or the first color light, the second color light, and the third color light are emitted in the form of a mixed light.

8. A heterocyclic compound represented by Formula 1: Among them, In Formula 1, Formula 2-1, and Formula 2-2, X is O or S, R1 to R8 are each independently selected from the group consisting of a group represented by Formula 2-1, a group represented by Formula 2-2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxy group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2), one of R1, R2, R4, R5, R7, and R8 is a group represented by Formula 2-1, and one of R1 to R8 that is not a group represented by Formula 2-1 is a group represented by Formula 2-2, R 11 to R 18 each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxy group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2), Two adjacent groups among R1 to R8 and R 11 to R 18 Two adjacent groups among them are optionally connected to each other to form a ring, Ar1 to Ar3 are each independently a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group, Ar2 and Ar3 are optionally connected to each other via a single bond, -C(Q4)(Q5)-, -Si(Q4)(Q5)-, -O-, -S-, -N(Q4)-, -B(Q4)-, -C(=O)-, -S(=O)2-, -S(=O)(Q4)(Q5)-, or -P(=O)(Q4)- to form a fused heterocycle, L 11 to L 13 each independently is a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group, a11 to a13 are each independently an integer from 0 to 3, When a11 is 0, *-(L 11 ) a11 -*' represents a single bond. When a12 is 0, *-(L 12 ) a12 -*' represents a single bond, and when a13 is 0, *-(L 13 ) a13 -*' represents a single bond, The substituted C5-C 60 carbocyclic group, the substituted C1-C 60 heterocyclic group, the substituted C1-C 60 alkyl group, the substituted C2-C 60 alkenyl group, the substituted C2-C 60 alkynyl group, the substituted C1-C 60 alkoxy group, the substituted C3-C 10 cycloalkyl group, the substituted C1-C 10 heterocycloalkyl group, the substituted C3-C 10 cycloalkenyl group, the substituted C1-C 10 heterocycloalkenyl group, the substituted C6-C 60 aryl group, the substituted C6-C 60 aryloxy group, the substituted C6-C 60 arylthio group, the substituted C1-C 60 heteroaryl group, at least one substituent of the substituted monovalent non-aromatic fused polycyclic group and the substituted monovalent non-aromatic fused heteropolycyclic group is selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazone group, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group and C1-C 60 alkoxy group; Each independently selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C1-C 60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 ) and -P(=O)(Q 11 )(Q 12 ) where at least one of the substituents is a C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group and C1-C 60 alkoxy group; C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C1-C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, biphenyl group and terphenyl group; Each is independently selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C 60 alkyl group, a C2-C 60 alkenyl group, a C2-C 60 alkynyl group, a C1-C 60 alkoxy group, a C3-C 10 cycloalkyl group, a C1-C 10 heterocycloalkyl group, a C3-C 10 cycloalkenyl group, a C1-C 10 heterocycloalkenyl group, a C6-C 60 aryl group, a C6-C 60 aryloxy group, a C6-C 60 arylthio group, a C1-C 60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, a biphenyl group, a terphenyl group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ), and -P(=O)(Q 21 )(Q 22 ) and is substituted with at least one of a C3-C 10 cycloalkyl group, a C1-C 10 heterocycloalkyl group, a C3-C 10 cycloalkenyl group, a C1-C 10 heterocycloalkenyl group, a C6-C 60 aryl group, a C6-C 60 aryloxy group, a C6-C 60 arylthio group, a C1-C 60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, a biphenyl group, and a terphenyl group; and -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 )和-P(=O)(Q 31 )(Q 32 ), Q1 to Q5, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxy group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C 60 alkyl group, a C2-C 60 alkenyl group, a C2-C 60 alkynyl group, a C1-C 60 alkoxy group, a C3-C 10 cycloalkyl group, a C1-C 10 heterocycloalkyl group, a C3-C 10 cycloalkenyl group, a C1-C 10 heterocycloalkenyl group, a C6-C 60 aryl group, a C6-C 60 aryl group substituted with a C1-C 60 alkyl group, a C1-C 60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, a biphenyl group and a terphenyl group, and * represents the connection site to the group represented by Formula 1, and *' represents the connection site to an adjacent atom.

9. The heterocyclic compound according to claim 8, wherein X is O, one of R1, R2, and R4 is a group represented by Formula 2-1, and one of R5 to R8 is a group represented by Formula 2-2, or X is S, one of R1, R2, and R4 is a group represented by Formula 2-1, and one of R5 to R8 is a group represented by Formula 2-2.

10. The heterocyclic compound according to claim 8, wherein: X is O, one of R1, R2, and R4 is a group represented by Formula 2-1, and one of R1 to R4 that is not a group represented by Formula 2-1 is a group represented by Formula 2-2; or X is S, one of R1, R2, and R4 is a group represented by Formula 2-1, and one of R1 to R4 that is not a group represented by Formula 2-1 is a group represented by Formula 2-2.

11. The heterocyclic compound according to claim 8, wherein R1 to R8 are each independently selected from: A group represented by Formula 2-1, a group represented by Formula 2-2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazone group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, a n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, a n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, a n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, a n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group; and A methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, a n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, a n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, a n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, a n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group, each of which is substituted with at least one selected from deuterium, -F, -Cl, -Br, and -I.

12. The heterocyclic compound according to claim 8, wherein in R1 to R8, groups that are not represented by Formula 2-1 or Formula 2-2 are each hydrogen.

13. The heterocyclic compound according to claim 8, wherein R 11 to R 18 are each independently selected from: Hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazone group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, a n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, a n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, a n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, a n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group; and A methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, a n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, a n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, a n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, a n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group, each of which is substituted with at least one selected from deuterium, -F, -Cl, -Br, and -I.

14. The heterocyclic compound according to claim 8, wherein L 11 to L 13 are each independently selected from: benzene group, pentalene group, indene group, naphthalene group, azulene group, heptalene group, indacene group, acenaphthylene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, pyrene group, group, tetracene group, picene group, perylene group, pyrrole group, thiophene group, furan group, silole group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, triazine group, benzofuran group, benzothiophene group, dibenzofuran group, dibenzothiophene group, carbazole group, benzosilole group, dibenzosilole group, quinoline group, isoquinoline group, benzimidazole group, imidazopyridine group and imidazopyrimidine group; Each is independently selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentacenyl group, an indenyl group, a naphthyl group, a azulene group, a heptacenyl group, an indacenyl group, an acenaphthylenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a pyrenyl group, a group, a tetracenyl group, a picenyl group, a perylenyl group, a pyrrolyl group, a thienyl group, a furyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a benzosilolyl group, a dibenzosilolyl group, a quinolinyl group, an isoquinolinyl group, a benzimidazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), and -P(=O)(Q 31 )(Q 32 ), and at least one of the substituted phenyl group, pentacenyl group, indenyl group, naphthyl group, azulene group, heptacenyl group, indacenyl group, acenaphthylenyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, pyrenyl group, a group, a tetracenyl group, a picenyl group, a perylenyl group, a pyrrolyl group, a thienyl group, a furyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a benzosilolyl group, a dibenzosilolyl group, a quinolinyl group, an isoquinolinyl group, a benzimidazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, and Q 31 to Q 33 each independently selected from C1-C 20 alkyl groups, C1-C 20 alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups and pyridyl groups.

15. The heterocyclic compound according to claim 8, wherein: L 11 to L 13 each independently represents a group represented by one selected from Formula 3-1 to Formula 3-39: wherein, in Formulas 3-1 to 3-39, Y1 is O, S, C(Z3)(Z4), N(Z3), or Si(Z3)(Z4), Z1 to Z4 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a pyrenyl group, yl group, a tetracenyl group, a pyrrolyl group, a thienyl group, a furyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a benzosilolyl group, a dibenzosilolyl group, a quinolinyl group, an isoquinolinyl group, a benzimidazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and -Si(Q 31 )(Q 32 )(Q 33 ), Q 31 to Q 33 each independently selected from C1-C 20 alkyl groups, C1-C 20 alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups and pyridyl groups, Z3 and Z4 are optionally connected to each other to form a substituted or unsubstituted C5-C 10 carbocyclic group or a substituted or unsubstituted C1-C 10 heterocyclic group, d2 is an integer from 0 to 2, d3 is an integer from 0 to 3, d4 is an integer from 0 to 4, d5 is an integer from 0 to 5, d6 is an integer from 0 to 6, d8 is an integer from 0 to 8, and * and *' each represent a bonding site to an adjacent atom.

16. The heterocyclic compound according to claim 8, wherein a11 is 0.

17. The heterocyclic compound according to claim 8, wherein Ar1 to Ar3 are each independently selected from: benzene group, pentalene group, indene group, naphthalene group, azulene group, heptalene group, indacene group, acenaphthylene group, fluorene group, spiro-cyclopentane-fluorene group, spiro-difluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, pyrene group, group, tetracene group, picene group, perylene group, pyrrole group, thiophene group, furan group, silole group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, triazine group, benzofuran group, benzothiophene group, dibenzofuran group, dibenzothiophene group, carbazole group, benzosilole group, dibenzosilole group, quinoline group, isoquinoline group, benzimidazole group, imidazopyridine group and imidazopyrimidine group; and Each independently selected from deuterium, -F, -Cl, -Br, -I, a hydroxy group, a cyano group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentacenyl group, an indenyl group, a naphthyl group, an azulene group, a heptacenyl group, an indacenyl group, an acenaphthylenyl group, a fluorenyl group, a spiro-cyclopentane-fluorenyl group, a spiro-difluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a pyrenyl group, a group, a tetracenyl group, a picenyl group, a perylenyl group, a pyrrolyl group, a thiophenyl group, a furyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a benzosilolyl group, a dibenzosilolyl group, a quinolinyl group, an isoquinolinyl group, a benzimidazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), and -P(=O)(Q 31 )(Q 32 ), and at least one substituted benzene group, pentacene group, indene group, naphthalene group, azulene group, heptacene group, indacene group, acenaphthylene group, fluorene group, spiro-cyclopentane-fluorenyl group, spiro-difluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, pyrene group, a group, a tetracene group, a picene group, a perylene group, a pyrrole group, a thiophene group, a furan group, a silole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a triazine group, a benzofuran group, a benzothiophene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a benzosilole group, a dibenzosilole group, a quinoline group, an isoquinoline group, a benzimidazole group, an imidazopyridine group, and an imidazopyrimidine group, and Q 31 to Q 33 each independently selected from C1-C 20 alkyl groups, C1-C 20 alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups and pyridyl groups.

18. The heterocyclic compound according to claim 8, wherein Ar1 to Ar3 are each independently a group represented by one selected from Formulas 4-1 to 4-24: Among them, In Formulas 4-1 to 4-24, Y 31 is O, S, C(Z 35 )(Z 36 ), N(Z 35 ) or Si(Z 35 )(Z 36 ), where Z 31 to Z 36 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorene group, a spiro-cyclopentane-fluorene group, a spiro-difluorene group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a pyrenyl group, yl group, a tetracenyl group, a pyrrolyl group, a thienyl group, a furyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a benzosilolyl group, a dibenzosilolyl group, a quinolinyl group, an isoquinolinyl group, a benzimidazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group and -Si(Q 31 )(Q 32 )(Q 33 ), Q 31 to Q 33 each independently selected from C1-C 20 alkyl groups, C1-C 20 alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups and pyridyl groups, e3 is an integer from 0 to 3, e4 is an integer from 0 to 4, e5 is an integer from 0 to 5, e6 is an integer from 0 to 6, e7 is an integer from 0 to 7, e8 is an integer from 0 to 8, e9 is an integer from 0 to 9, and * represents a bonding site to an adjacent atom.

19. The heterocyclic compound according to claim 8, wherein: Ar1 is a phenyl group, and Ar2 and Ar3 are each independently selected from: a phenyl group, a naphthyl group, a fluorenyl group, a spiro-cyclopentane-fluorenyl group, a spiro-difluorenyl group, a benzo-fluorenyl group, a dibenzo-fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, and a dibenzosilolyl group; and Each is independently selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a spiro-cyclopentane-fluorenyl group, a spiro-difluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a dibenzosilolyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), and -P(=O)(Q 31 )(Q 32 ), and at least one of the substituted phenyl group, naphthyl group, fluorenyl group, spiro-cyclopentane-fluorenyl group, spiro-difluorenyl group, benzofluorenyl group, dibenzofluorenyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, and dibenzosilolyl group.

20. The heterocyclic compound according to claim 8, wherein the heterocyclic compound is selected from Compound 1 to Compound 348:

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