Heterocyclic compounds and organic light-emitting devices comprising the same

Abstract

Provided are a heterocyclic compound and an organic light emitting device including the same.

Description

[0001] Cross-references to related applications

[0002] This application claims the benefit of Korean Patent Application No. 10-2017-0018957, filed with the Korean Intellectual Property Office on February 10, 2017, and Korean Patent Application No. 10-2018-0013089, filed on February 1, 2018, the disclosure of which is incorporated herein by reference in its entirety. Technical Field

[0003] One or more embodiments relate to fused heterocyclic compounds and organic light-emitting devices including the fused heterocyclic compounds. Background Technology

[0004] Compared to existing devices, organic light-emitting devices are self-emissive devices, which have a relatively wide viewing angle, relatively high contrast, relatively short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed.

[0005] An organic light-emitting device may include a first electrode disposed on a substrate, and a hole transport region, an emitter layer, an electron transport region, and a second electrode sequentially disposed on the first electrode. Holes supplied by the first electrode can move through the hole transport region to the emitter layer, and electrons supplied by the second electrode can move through the electron transport region to the emitter layer. Charge carriers (such as holes and electrons) recombine in the emitter layer to generate excitons. The excitons then transition from an excited state to a ground state, thereby generating light. Summary of the Invention

[0006] One or more embodiments include heterocyclic compounds.

[0007] One or more embodiments include an organic light-emitting device containing the heterocyclic compound.

[0008] Other aspects will be set forth in part in the description which follows, and will be apparent in part from the description, or may be learned by practicing the proposed embodiments.

[0009] This disclosure provides heterocyclic compounds represented by Formula 1:

[0010] <Formula 1>

[0011]

[0012] <Formula 2>

[0013]

[0014] In Equations 1 and 2,

[0015] X1 can be a single bond, C(R)21 (R) 22 ), Si(R) 21 (R) 22 ), N(R 23 ), O or S,

[0016] X2 can be a single bond, C(R) 31 (R) 32 ), Si(R) 31 (R) 32 ), N(R 33 ), O or S,

[0017] c2 can be 0 or 1. When c2 is 0, X2 may not exist and Ar1 and Ar2 may not be connected.

[0018] L1 and L2 can be independently selected from single-bonded, substituted, or unsubstituted C3-C bonds. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0019] a1 and a2 can each be an independent integer from 1 to 5, where when a1 is 2 or greater, two or more L1s can be the same or different from each other, and when a2 is 2 or greater, two or more L2s can be the same or different from each other.

[0020] R1 to R3, R 11 To R 18 and R 21 To R 23 Each can be independently selected from groups represented by formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2) and -C(=O)(Q1),

[0021] R 31 To R 33 Each can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2) and -C(=O)(Q1),

[0022] b1 can be an integer from 0 to 3. When b1 is 2 or greater, two or more R1s can be the same or different from each other.

[0023] b2 can be an integer from 0 to 2, where when b2 is 2 or greater, two or more R2s can be the same or different from each other.

[0024] Ar1 and Ar2 can be independently selected from substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl and substituted or unsubstituted C1-C 60 Mixed aromatics,

[0025] The condition is that,

[0026] i) L1 does not have to be a single bond.

[0027] ii) When L1 is a single bond and a1 is 1, R 11 To R 18 At least one of them can be a group represented by Formula 2, or

[0028] iii) L1 is a single bond, a1 is 1 and X1 is C(R) 21 (R) 22 In the case of R, 21 and R 22 It can connect to form substituted or unsubstituted C4-C 20 The carbocyclic group may or may not be substituted C2-C 20 Heterocyclic groups,

[0029] Replacement C3-C 10 Cycloalkylene, substituted C1-C 10 Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 aryl, substituted C1-C 60 Heteroaryl groups, substituted divalent nonaromatic fused polycyclic groups, substituted divalent nonaromatic fused heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthio, substituted C1-C 60 Heteroaryl, substituted monovalent nonaromatic fused polycyclic groups, substituted monovalent nonaromatic fused heterocyclic groups, substituted C4-C 20 Carbocyclic groups and substituted C2-C 20 At least one substituent of the heterocyclic group may be selected from:

[0030] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;

[0031] Each is substituted by at least one of the following C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 ) and -P(=O)(Q 11 (Q) 12 );

[0032] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups;

[0033] Each is replaced by at least one of the following C3-C 10 cycloalkyl, C1-C 10Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) or -P(=O)(Q 21 (Q) 22 );and

[0034] -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

[0035] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23and Q 31 To Q 33 Each can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heterocyclic group, C1-C substituted with at least one of deuterium, -F and cyano. 60 Alkyl group, C6-C group substituted with at least one of deuterium, -F and cyano groups 60 Aryl, biphenyl, and terphenyl, and

[0036] * indicates a binding site with an adjacent atom.

[0037] Another aspect of this disclosure provides 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, wherein the organic layer comprises an emitting layer and at least one of the heterocyclic compounds. Attached Figure Description

[0038] These and / or other aspects will become apparent and more readily understood in conjunction with the accompanying drawings and the following description of the embodiments, wherein

[0039] Figures 1 to 4 Each is a schematic diagram of an organic light-emitting device according to an embodiment. Detailed Implementation

[0040] Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements in the description. In this respect, embodiments may take different forms and should not be construed as limited to the descriptions listed herein. Therefore, embodiments are described below only by reference to the accompanying drawings to explain aspects of this specification. As used herein, the term “and / or” includes any and all combinations of one or more of the associated listed items. For example, the expression “at least one,” when preceding a column of elements, modifies the entire column of elements without modifying any individual element within the column.

[0041] The heterocyclic compound according to the embodiments can be represented by Formula 1:

[0042] <Formula 1>

[0043]

[0044] <Formula 2>

[0045]

[0046] In Equation 1, X1 can be a single bond, C(R) 21 (R) 22 ), Si(R) 21 (R) 22 ), N(R 23 ), O or S.

[0047] In one implementation, X1 can be a single bond, C(R) 21 (R) 22 ), Si(R) 21 (R) 22 ) or O.

[0048] In Equation 2, X2 can be a single bond, C(R) 31 (R) 32 ), Si(R) 31 (R) 32 ), N(R 33 ), O or S.

[0049] In one implementation, X2 can be a single bond, C(R) 31 (R) 32 ), Si(R) 31 (R) 32 ) or O.

[0050] In Equation 2, c2 represents the quantity of X2, and c2 can be 0 or 1. When c2 is 0, X2 may not exist and Ar1 and Ar2 may not be connected.

[0051] In one implementation, c2 can be 1.

[0052] In equations 1 and 2, R1 to R3, R 11 To R 18 and R 21 To R 23 Each can be independently selected from groups represented by formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), and -C(=O)(Q1), and

[0053] R 31 To R 33 Each can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2) and -C(=O)(Q1).

[0054] In one implementation, R1 to R3, R 11 To R 18 and R 21 To R 23 Each can be selected independently from:

[0055] The groups represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20Alkyl groups, C1-C groups substituted with at least one group selected from -F and cyano groups 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, fluorenyl, spirofluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, and triazinyl; and

[0056] Each of the following is substituted with at least one of the following: phenyl, naphthyl, fluorenyl, spirofluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene. alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl and triazinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazyl, hydrazone, C1-C 20 Alkyl groups, C1-C groups substituted with at least one group selected from -F and cyano groups 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, fluorenyl, spirofluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene The compounds include pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, and triazinyl.

[0057] R 31 To R 33 Each can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl groups, C1-C groups substituted with at least one group selected from -F and cyano groups 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, fluorenyl, spirofluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, and triazinyl; and

[0058] Each of the following is substituted with at least one of the following: phenyl, naphthyl, fluorenyl, spirofluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene. alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl and triazinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazyl, hydrazone, C1-C 20 Alkyl groups, C1-C groups substituted with at least one group selected from -F and cyano groups 20 Alkyl, C1-C20 Alkoxy, phenyl, naphthyl, fluorenyl, spirofluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene The compounds are pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, and triazinyl.

[0059] In one or more embodiments, R1 to R3, R 11 To R 18 and R 21 To R 23 Each can be selected independently from:

[0060] The groups represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, -CF3, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, pyrene, alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, and triazinyl; and

[0061] Each of the following is substituted with at least one of the following: phenyl, naphthyl, fluorenyl, phenanthryl, anthraceneyl, pyrene, alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl and triazinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazyl, hydrazone, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, -CF3, phenyl, naphthyl, fluorenyl, phenanthryl, anthraceneyl, pyrene, alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, and triazinyl.

[0062] R 31 To R 33 Each can be selected independently from:

[0063] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, -CF3, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, pyrene, alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, and triazinyl; and

[0064] Each of the following is substituted with at least one of the following: phenyl, naphthyl, fluorenyl, phenanthryl, anthraceneyl, pyrene, alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl and triazinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazyl, hydrazone, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, -CF3, phenyl, naphthyl, fluorenyl, phenanthryl, anthraceneyl, pyrene, The compounds are pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, and triazinyl.

[0065] In one embodiment, R1 and R2 can each be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, -CF3, phenyl, and biphenyl.

[0066] R 11 To R 18 Each of the following groups can be independently selected: free group represented by formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, -CF3, phenyl, and biphenyl.

[0067] In one implementation, R3, R 21 To R 23 and R 31 To R 33 Each can be selected independently from:

[0068] Methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, -CF3, phenyl, naphthyl, fluorenyl, spirofluorenyl, phenanthryl, anthraceneyl, pyrene, alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, and triazinyl; and

[0069] Each of the following is substituted with at least one of the following: phenyl, naphthyl, fluorenyl, spirofluorenyl, phenanthryl, anthraceneyl, pyreneyl. alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl and triazinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazyl, hydrazone, C1-C 20 Alkyl groups, C1-C groups substituted with at least one group selected from -F and cyano groups 20 Alkyl, C1-C 20Alkoxy, phenyl, naphthyl, fluorenyl, spirofluorenyl, phenanthryl, anthraceneyl, pyrene, The compounds are pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, and triazinyl.

[0070] In Equation 1, b1 represents the number of R1s, and b1 can be an integer from 0 to 3. When b1 is 2 or greater, two or more R1s can be the same or different from each other.

[0071] In Equation 1, b2 represents the number of R2, and b2 can be an integer from 0 to 2. When b2 is 2 or greater, two or more R2 can be the same or different from each other.

[0072] In Equations 1 and 2, L1 and L2 can be independently selected from single-bonded, substituted, or unsubstituted C3-C bonds. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hypoaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0073] In one implementation, L1 and L2 can each be independently selected from:

[0074] Single bond, phenylene, naphthylene, fluorene, spiro-difluorene, spiro-fluorene-benzofluorene, benzo[fluorene], dibenzo[fluorene], phenenylene, anthracene, fluorenylene, benzo[phenanthrene], pyridylene, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzo[quinolinyl], naphthidylene, quinoxalinyl, quinazolinyl, carbazolyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, triazinyl, dibenzofuranyl and dibenzophenylthio; and

[0075] Each of the following substituted groups is selected from at least one of the following: phenylene, naphthylene, fluorene, spiro-difluorene, spiro-fluorene-benzofluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenenylene, phenanthrene, anthracene, fluorenylene, benzo[a]phenanthrene, pyridylene, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzo[a]quinolinyl, naphthinyl, quinoxalinyl, quinazolinyl, carbazolyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, triazinyl, dibenzofuranyl, and dibenzophenylthioyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzofluorenyl, benzo[fluorenyl], dibenzo[fluorenyl], phenatenyl, anthraceneyl, fluoranyl, benzo[phenanthrene], pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzo[quinolinyl], naphridyl, quinoxalinyl, quinazolinyl, carbazoyl, phenanthrynyl, acridineyl, phenanthrolinel, phenazinyl, triazinyl, dibenzofuranyl, and dibenzophenylthioyl.

[0076] In one embodiment, L1 and L2 may each be independently selected from single bonds and groups represented by formulas 3-1 to 3-28, but the embodiments of this disclosure are not limited thereto:

[0077]

[0078] In equations 3-1 to 3-28,

[0079] Y1 can be O, S, C(Z3)(Z4), N(Z5), or Si(Z6)(Z7).

[0080] Z1 to Z7 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, phenatenyl, phenanthryl, anthraceneyl, fluoranyl, benzophenanthryl, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, naphridyl, quinoxalinyl, quinazolinyl, carbazoleyl, phenanthryl, acridineyl, phenanthrololinyl, phenazinyl, triazinyl, dibenzofuranyl, and dibenzophenylthioyl

[0081] d2 can be an integer from 0 to 2, where when d2 is 2 or greater, two or more Z1s can be the same or different from each other.

[0082] d3 can be an integer from 0 to 3, where when d3 is 2 or greater, two or more Z1s can be the same or different from each other, and two or more Z2s can be the same or different from each other.

[0083] d4 can be an integer from 0 to 4, where when d4 is 2 or greater, two or more Z1s can be the same or different from each other.

[0084] d5 can be an integer from 0 to 5, where when d5 is 2 or greater, two or more Z1s can be the same or different from each other, and two or more Z2s can be the same or different from each other.

[0085] d6 can be an integer from 0 to 6, where when d6 is 2 or greater, two or more Z1s can be the same or different from each other.

[0086] d8 can be an integer from 0 to 8, where when d8 is 2 or greater, two or more Z1s can be the same or different from each other, and

[0087] * and *' indicate the binding site with adjacent atoms.

[0088] In one or more embodiments, L1 and L2 may each be independently selected from single bonds and groups represented by formulas 4-1 to 4-14, but the embodiments of this disclosure are not limited thereto:

[0089]

[0090] In Equations 4-1 to 4-14, * and *' each represent a binding site with an adjacent atom.

[0091] In Equation 1, a1 represents the number of L1s, and a1 can be an integer from 1 to 5. When a1 is 2 or greater, two or more L1s can be the same or different from each other.

[0092] In Equation 2, a2 ​​represents the number of L2s, and a2 can be an integer from 1 to 5. When a2 is 2 or greater, two or more L2s can be the same or different from each other.

[0093] In Equation 2, Ar1 and Ar2 can each be independently selected from substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl and substituted or unsubstituted C1-C 60 Mixed aromatic compounds.

[0094] In one implementation, Ar1 and Ar2 can each be independently selected from:

[0095] Phenyl, pentanyl, indene, naphthyl, azulel, heptanyl, indoleyl, acenaphthel, fluorenyl, spirofluorenyl, phenanthrenyl, anthrayl, fluoranyl, benzo[phenanthryl], pyrene, alkyl, tetraphenyl, lavany, perylene, penfenyl, hexaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinazolinyl, cenolinyl, carbazole, phenanthridine, acridineyl, phenanthrolinyl, phenazinyl, benzoxazolyl, benzimidazolyl, furanyl, benzofuranyl, phenylthio, benzophenylthio, thiazolyl, isothiazolyl, benzothiazolyl, isoxazolyl, oxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, benzoxazolyl, dibenzofuranyl, dibenzophenylthio, and benzocarbazole; and

[0096] Each of the following is substituted with at least one of the following: phenyl, pentanenyl, indene, naphthyl, azuleyl, heptenyl, indoleyl, acenaphtheyl, fluorenyl, spirofluorenyl, phenanthyl, phenanthryl, anthraceneyl, fluoranthraceneyl, benzo[a]phenanthryl, pyreneyl, alkyl, tetraphenyl, francyl, perylene, penfenyl, hexaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, inzolyl, purine, quinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, carbazole, phenanthridine, acridineyl, phenanthroxalinyl, phenazinyl, benzoxazolyl, benzimidazole alkyl, furanyl, benzofuranyl, phenylthio, benzophenylthio, thiazolyl, isothiazolyl, benzothiazolyl, isoxazolyl, oxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, benzooxazolyl, dibenzofuranyl, dibenzophenylthio and benzocarbazoleyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, C6-C 20 Aryl and C1-C 20 Mixed aromatic compounds.

[0097] In one embodiment, Ar1 and Ar2 can each be independently selected from phenyl, naphthyl, fluorenyl, spirofluorenyl, phenanthryl, anthraceneyl, pyrene, etc. alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, and triazinyl; and

[0098] Each of the following is substituted with at least one of the following: phenyl, naphthyl, fluorenyl, spirofluorenyl, phenanthryl, anthraceneyl, pyreneyl. alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl and triazinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, fluorenyl, spirofluorenyl, phenanthryl, anthraceneyl, pyrene, The compounds are pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, and triazinyl.

[0099] In one implementation, at least one of the following is satisfied in Equation 1:

[0100] i) L1 may not be a single bond;

[0101] ii) When L1 is a single bond and a1 is 1, R 11 To R 18 At least one of them can be a group represented by Formula 2; or

[0102] iii) L1 is a single bond, a1 is 1 and X1 is C(R) 21 (R) 22 In the case of R, 21 and R 22 It can connect to form substituted or unsubstituted C4-C 20 The carbocyclic group may or may not be substituted C2-C 20 Heterocyclic groups.

[0103] In one embodiment, the heterocyclic compound can be represented by formula 1-1:

[0104] <Formula 1-1>

[0105]

[0106] In Equation 1-1, X1, L1, R1 to R3, R 11 To R 18 R 21 To R 23 a1, b1, and b2 can be the same as those defined in Equation 1.

[0107] In one implementation, L1 in Equation 1 may not be a single bond.

[0108] In one implementation, when L1 in Equation 1 is a single bond and a1 is 1, R 13 and R 16 At least one of them can be represented by Equation 2.

[0109] In one embodiment, the heterocyclic compound can be represented by formula 1-2:

[0110] <Equation 1-2>

[0111]

[0112] In Equation 1-2, X can be a single bond, C(R) bond, or C(R) bond. 41 (R) 42 ), Si(R) 41 (R) 42 ), N(R 43 ), O or S.

[0113] In Equation 1-2, A1 and A2 can be independently selected from:

[0114] Phenyl, naphthyl, fluorenyl, phenanthryl, anthraceneyl, pyrene alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, and triazinyl; and

[0115] Each of the following is substituted with at least one of the following: phenyl, naphthyl, fluorenyl, phenanthryl, anthraceneyl, pyrene, alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl and triazinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, fluorenyl, spirofluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene The compounds are pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, and triazinyl.

[0116] In equation 1-2, R 41 To R 43 R 51 and R 52 Each can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2) and -C(=O)(Q1).

[0117] In Equation 1-2, b51 represents R 51 The number of R, and b51 can be an integer from 0 to 5, where when b51 is 2 or greater, two or more R 51 They can be the same as or different from each other.

[0118] In Equation 1-2, b52 represents R 52 The number of R, and b52 can be an integer from 0 to 5, where when b52 is 2 or greater, two or more R 52 They can be the same as or different from each other.

[0119] In Equation 1-2, L1, R1 to R3, R 11 To R 18 Q1 to Q3, a1, b1 and b2 can be the same as those defined in Equation 1.

[0120] In one embodiment, the heterocyclic compound represented by Formula 1 may have a band gap of about 0.3 eV or less between the singlet (S1) and triplet (T1) energy levels. ST ).

[0121] In one embodiment, the heterocyclic compound may be selected from compounds 1 to 7, but the embodiments of this disclosure are not limited thereto:

[0122]

[0123] Heterocyclic compounds can simultaneously include substituents with electron-withdrawing (EWG) and electron-donating (EDG) properties. When these substituents are introduced into appropriate positions, the energy gap (ΔE) between the singlet S1 level and the triplet T1 level of the entire compound can be appropriately controlled. st This demonstrates thermally activated delayed fluorescence (TADF).

[0124] Heterocyclic compounds can possess singlet S1 and triplet T1 energy levels that satisfy the following equation:

[0125] ΔE st =S1–T1<0.3eV.

[0126] Heterocyclic compounds can have the structure of Formula 1. In particular, intramolecular charge transfer can be achieved due to the inclusion of EWG and EDG within the heterocyclic compound. Furthermore, this structure, with steric hindrance between EWG and EDG, effectively prevents orbital overlap in the heterocyclic compound, ensuring that the singlet S1 level does not overlap with the triplet T1 level, resulting in a very low ΔE. st In this respect, even at room temperature, reverse intersystem crossing from the excited triplet state T1 to the singlet state S1 can be achieved through thermal activation, thereby exhibiting delayed fluorescence.

[0127] To increase the highest occupied molecular orbital (HOMO) distribution of EDG in the heterocyclic compound of Formula 1, electron-donating substituents can be introduced to induce thermally activated delayed fluorescence of EDG. For example, an electron-donating substituent can be introduced at the R position of the EDG (e.g., carbazole group). 13 and / or R 16 Electron-donating substituents are introduced at the site to induce thermally activated delayed fluorescence.

[0128] Furthermore, by introducing a spirocyclic structure into EDG, the likelihood of vibrational motion in heterocyclic compounds can be reduced. This also reduces the possibility of transferred electrons not emitting light, thereby improving the luminescence efficiency of heterocyclic compounds.

[0129] To control the emission region, electron-withdrawing substituents can be appropriately substituted at the nitrogen position (i.e., the R3 position) of the 1,8-naphthalimide as an EWG, thereby allowing for fine tuning of the emission wavelength into the long-wavelength region. For example, a phenyl group substituted with an EWG such as trifluoromethyl (-CF3) or cyano can be introduced at the nitrogen position of the 1,8-naphthalenedimide.

[0130] Furthermore, heterocyclic compounds can possess relatively high charge transport capabilities (e.g., holes or electrons). Therefore, in organic light-emitting devices comprising heterocyclic compounds represented by Formula 1, the exciton formation rate within the emitter layer of the organic light-emitting device can be increased, thus enabling such organic light-emitting devices to exhibit low driving voltage, high efficiency, long lifetime, and high maximum quantum efficiency.

[0131] The method for synthesizing heterocyclic compounds represented by Formula 1 will be readily apparent to those skilled in the art by referring to the following examples.

[0132] However, the present invention can be implemented in many different forms and should not be limited to the exemplary embodiments.

[0133] At least one heterocyclic compound of Formula 1 may be used or included between a pair of electrodes in an organic light-emitting device. For example, the heterocyclic compound may be included in at least one layer selected from hole transport regions, electron transport regions, and emission layers. In one or more embodiments, the heterocyclic compound of Formula 1 may be used as a material for a capping layer located outside a pair of electrodes in an organic light-emitting device.

[0134] Therefore, an organic light-emitting device is provided, comprising: 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 comprising an emitting layer, wherein the organic layer comprises at least one heterocyclic compound represented by Formula 1.

[0135] The expression “(organic layer) comprises at least one heterocyclic compound” as used herein can include cases where “(organic layer) comprises the same heterocyclic compound represented by Formula 1” and cases where “(organic layer) comprises two or more different heterocyclic compounds represented by Formula 1”.

[0136] For example, the organic layer may comprise only compound 1 as a heterocyclic compound. In this respect, compound 1 may be present in the emitting layer of the organic light-emitting device. In one or more embodiments, the organic layer may comprise both compound 1 and compound 2 as heterocyclic compounds. In this respect, compound 1 and compound 2 may be present in the same layer (e.g., both compound 1 and compound 2 may be present in the emitting layer) or in different layers (e.g., compound 1 may be present in the emitting layer, while compound 2 may be present in the electron transport layer).

[0137] In one embodiment, the first electrode of the organic light-emitting device can be the anode.

[0138] The second electrode of an organic light-emitting device can be a cathode.

[0139] The organic layer of the organic light-emitting device may further include a hole transport region between the first electrode and the emitting layer, and an electron transport region between the emitting layer and the second electrode.

[0140] The hole transport region may include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof, and

[0141] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0142] In one or more embodiments, the emitting layer of the organic light-emitting device may include a heterocyclic compound represented by Formula 1.

[0143] In one or more embodiments, the heterocyclic compound represented by Formula 1 included in the emitting layer of the organic light-emitting device may be a TADF emitter, such that the emitting layer can emit delayed fluorescence.

[0144] In one or more embodiments, the emitting layer of the organic light-emitting device may be composed of a heterocyclic compound represented by Formula 1. In one or more embodiments, the emitting layer of the organic light-emitting device may further include a body, and the amount of the heterocyclic compound represented by Formula 1 may be in the range of about 0.1 parts by weight to about 50 parts by weight, based on 100 parts by weight of the emitting layer.

[0145] The main body included in the emission layer may include at least one selected from anthracene compounds, pyrene compounds, and spirodifluorene compounds, but the embodiments disclosed herein are not limited thereto.

[0146] In one embodiment, the hole transport region of the organic light-emitting device may include a p-type dopant, wherein the p-type dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of -3.5 eV or less.

[0147] As used herein, the term "organic layer" refers to a single layer and / or multiple layers between the first and second electrodes of an organic light-emitting device. Materials included in the "organic layer" are not limited to organic materials.

[0148] Figure 1 A schematic diagram of an organic light-emitting device 10 according to an embodiment is illustrated. The organic light-emitting device 10 may include a first electrode 110, an organic layer 150, and a second electrode 190.

[0149] The following text will combine Figure 1 The structure of the organic light-emitting device 10 according to the embodiments and the method for preparing the organic light-emitting device 10 are described.

[0150] exist Figure 1 In this process, the substrate can be attached below the first electrode 110 or above the second electrode 190. The substrate can be a glass substrate or a plastic substrate, each possessing excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

[0151] The first electrode 110 can be formed by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode can be selected from materials with high work function to facilitate hole injection.

[0152] The first electrode 110 can be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material used to form the first electrode can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof, but the embodiments of this disclosure are not limited thereto. When the first electrode 110 is a semi-transparent electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used as the material used to form the first electrode 110. However, the material used to form the first electrode 110 is not limited thereto.

[0153] 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 to this.

[0154] An organic layer 150 is disposed on the first electrode 110. The organic layer 150 may include an emitter layer.

[0155] The organic layer 150 may also include a hole transport region between the first electrode 110 and the emitter layer and an electron transport region between the emitter layer and the second electrode 190.

[0156] The hole transport region may have i) a single-layer structure comprising a single layer of a single material, ii) a single-layer structure comprising a single layer of multiple different materials, or iii) a multi-layer structure comprising multiple layers of multiple different materials.

[0157] The hole transport region may include at least one layer selected from the hole injection layer, hole transport layer, emission assist layer and electron blocking layer.

[0158] For example, the hole transport region can have a single-layer structure or a multi-layer structure. The single-layer structure includes a single layer containing a variety of different materials. The multi-layer structure has a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure. For each structure, the constituent layers are stacked sequentially on the first electrode 110 in the order described above, but the structure of the hole transport region is not limited to this.

[0159] The hole transport region may include 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), PEDOT / PSS (poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate)), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), compounds represented by Formula 201, and compounds represented by Formula 202:

[0160]

[0161] <Form 201>

[0162]

[0163] <Form 202>

[0164]

[0165] In equations 201 and 202,

[0166] L 201 To L 204 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0167] L 205 It can be selected from *-O-*', *-S-*', *-N(Q) 201 )-*', substituted or unsubstituted C1-C 20 Alkylene, substituted or unsubstituted C2-C 20 alkenyl, substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0168] xa1 to xa4 can each be an integer from 0 to 3 independently.

[0169] xa5 can be an integer from 1 to 10, and

[0170] R 201 To R 204 and Q 201 Each can be independently selected from substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.

[0171] For example, in equation 202, R 201 and R 202 It can be optionally linked via a single bond, a dimethyl-methylene bond, or a diphenyl-methylene bond, and R 203 and R 204 It can be optionally linked by a single bond, a dimethyl-methylene bond, or a diphenyl-methylene bond.

[0172] In one or more embodiments, in formulas 201 and 202,

[0173] L 201 To L 205 Each can be selected independently from:

[0174] Phenylidene, pentylene, indene, naphthyl, azulene, heptylene, acenaphthene, fluorene, spiro-difluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenenenyl, phenanthrene, anthracene, fluorenyl, benzo[a]phenanthrene, pyrene, etc. alkyl, tetraphenyl, purylene, perylene, pentafenyl, hexaphenylene, pentaphenylene, rubidylene, myristyl, oleophyne, phenylthioene, furanyl, carbazolyl, indoleyl, isoydinolyl, benzofuranyl, benzobenzenthioene, dibenzofuranyl, dibenzobenzenthioene, benzocarbazolyl, dibenzocarbazolyl, dibenzosiloxanediyl and pyridyl; and

[0175] Each of the following is substituted with at least one of the following: phenylene, pentyleneylene, indenylene, naphthylene, azoxyene, heptyleneylene, acenaphtheneylene, fluoreneylene, spiro-difluoreneylene, benzo[a]fluoreneylene, dibenzo[a]fluoreneylene, phenenenylene, phenanthreneylene, anthraceneylene, fluorenylene, benzo[a]phenanthreneylene, pyreneylene, etc. alkyl, tetraphenyl, purylene, perylene, pentaphenylene, hexaphenylene, pentaphenylene, rubidylene, myristyl, oleophyne, phenylthioene, furanyl, carbazolyl, indoleyl, isoydinolyl, benzofuranyl, benzobenzenethioene, dibenzofuranyl, dibenzobenzenethioene, benzocarbazolyl, dibenzocarbazolyl, dibenzosilicyclopentadienyl and pyridylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C1-C 10 Alkyl-substituted phenyl, -F-substituted phenyl, pentanenyl, indene, naphthyl, azuleyl, heptenyl, indaneyl, acenaphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthreneyl, phenanthreneyl, anthraceneyl, fluoranyl, benzo[a]phenanthreneyl, pyreneyl alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rutinyl, keratyl, ovolenyl, phenylthio, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzobenzenethio, dibenzofuranyl, dibenzobenzenethio, benzocarbazoleyl, dibenzocarbazoleyl, dibenzosiloxanepentadienyl, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 ),and

[0176] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0177] In one or more embodiments, xa1 to xa4 can each be 0, 1 or 2 independently.

[0178] In one or more embodiments, xa5 can be 1, 2, 3 or 4.

[0179] In one or more embodiments, R 201 To R 204 and Q 201 Each of these can be independently selected from phenyl, biphenyl, terphenyl, pentanenyl, indene, naphthyl, azuleyl, heptenyl, indaneyl, acenaphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenerenoyl, phenanthryl, anthraceneyl, fluoranyl, benzo[a]phenanthryl, pyrene, etc. alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rutinyl, keratyl, ovoleyl, phenylthio, furanyl, carbazoleyl, indoleyl, isoydinoleyl, benzofuranyl, benzophenylthio, dibenzofuranyl, dibenzophenylthio, benzocarbazoleyl, dibenzocarbazoleyl, dibenzosiloxanepentadienyl and pyridyl; and

[0180] Each of the following is substituted with at least one of the following: phenyl, biphenyl, terphenyl, pentanenyl, indole, naphthyl, azuleyl, heptenyl, indoleyl, acenaphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, benzo[a]phenanthryl, pyrene, alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rutinyl, keratyl, ovolenyl, phenylthio, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzobenzenethio, dibenzofuranyl, dibenzobenzenethio, benzocarbazoleyl, dibenzocarbazoleyl, dibenzosiloxanepentadienyl and pyridyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C1-C 10 Alkyl-substituted phenyl, -F-substituted phenyl, pentanenyl, indene, naphthyl, azuleyl, heptenyl, indaneyl, acenaphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthreneyl, phenanthreneyl, anthraceneyl, fluoranyl, benzo[a]phenanthreneyl, pyreneyl alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rutinyl, keratyl, ovolenyl, phenylthio, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzobenzenethio, dibenzofuranyl, dibenzobenzenethio, benzocarbazoleyl, dibenzocarbazoleyl, dibenzosiloxanepentadienyl, pyridyl, -Si(Q) 31 (Q)32 (Q) 33 ) and -N(Q 31 (Q) 32 ),and

[0181] Q 31 To Q 33 Same as described above.

[0182] In one or more embodiments, in formula 201, R 201 To R 203 At least one of them can be independently selected from:

[0183] Fluorenyl, spiro-difluorenyl, carbazole, dibenzofuranyl and dibenzophenylthio; and

[0184] Each of the following is substituted with at least one of the following: fluorenyl, spiro-difluorenyl, carbazole, dibenzofuranyl, and dibenzophenylthioyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C1-C 10 Alkyl-substituted phenyl, -F-substituted phenyl, naphthyl, fluorenyl, spiro-difluorenyl, carbazole, dibenzofuranyl, and dibenzophenylthioyl,

[0185] However, the embodiments disclosed herein are not limited thereto.

[0186] In one or more embodiments, in formula 202, i)R 201 and R 202 It can be connected via a single key and / or ii)R 203 and R 204 It can be connected with a single button.

[0187] In one or more embodiments, in formula 202, R 201 To R 204 At least one of them can be selected from:

[0188] Carbazolyl; and

[0189] The carbazoyl group is substituted with at least one of the following: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C1-C 10Alkyl-substituted phenyl, -F-substituted phenyl, naphthyl, fluorenyl, spiro-difluorenyl, carbazole, dibenzofuranyl, and dibenzophenylthioyl,

[0190] However, the embodiments disclosed herein are not limited thereto.

[0191] The compound represented by formula 201 can also be represented by formula 201A:

[0192] <Form 201A>

[0193]

[0194] In one embodiment, the compound represented by formula 201 may be represented by formula 201A(1), but the embodiments of this disclosure are not limited thereto:

[0195] <Formula 201A(1)>

[0196]

[0197] In one embodiment, the compound represented by formula 201 may be represented by formula 201A-1, but the embodiments of this disclosure are not limited thereto:

[0198] <Formula 201A-1>

[0199]

[0200] In one embodiment, the compound represented by formula 202 can be represented by formula 202A:

[0201] <Form 202A>

[0202]

[0203] In one embodiment, the compound represented by formula 202 can be represented by formula 202A-1:

[0204] <Formula 202A-1>

[0205]

[0206] In equations 201A, 201A(1), 201A-1, 202A, and 202A-1,

[0207] L 201 To L 203 xa1 to xa3, xa5 and R 202 To R 204 It can be the same as described above.

[0208] R 211 and R 212Each can independently combine with R 203 The descriptions are the same, and

[0209] R 213 To R 217 Each can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C1-C 10 Alkyl-substituted phenyl, -F-substituted phenyl, pentanenyl, indene, naphthyl, azuleyl, heptenyl, indaneyl, acenaphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthreneyl, phenanthreneyl, anthraceneyl, fluoranyl, benzo[a]phenanthreneyl, pyreneyl alkyl, tetraphenyl, styrene, peryl, pentylene, hexaphenyl, pentaphenyl, rubidinyl, keratinyl, ovoleyl, phenylthio, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzobenzenethio, dibenzofuranyl, dibenzobenzenethio, benzocarbazolyl, dibenzocarbazolyl, dibenzosiloxanepentadienyl, and pyridyl.

[0210] The hole transport region may include at least one compound selected from compounds HT1 to HT39, but embodiments of this disclosure are not limited thereto:

[0211]

[0212]

[0213]

[0214] The thickness of the hole transport region can be approximately to approximately For example, about to approximately Within the range. When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer can be approximately... to approximately For example, about to approximately Within a certain range, and the thickness of the hole transport layer can be approximately [missing information]. to approximately For example, about to approximately Within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage when the thicknesses of the hole transport region, hole injection layer, and hole transport layer are within these ranges.

[0215] The emission assist layer can increase luminous efficiency by compensating for the optical resonant distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block the flow of electrons from the electron transport region. The emission assist layer and the electron blocking layer can include the materials described above.

[0216] In addition to these materials, the hole transport region may also include charge-generating materials to improve conductivity. The charge-generating materials may be uniformly or non-uniformly dispersed within the hole transport region.

[0217] The charge-generating material can be, for example, a p-doped agent.

[0218] In one implementation, the p-dopant may have a LUMO level of -3.5 eV or less.

[0219] p-dopers may include at least one selected from quinone derivatives, metal oxides, and cyano-containing compounds, but the embodiments disclosed herein are not limited thereto.

[0220] For example, p-dopers may include at least one selected from the following:

[0221] Quinone derivatives, such as tetracyanoquinone dimethyl ether (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl ether (F4-TCNQ);

[0222] Metal oxides, such as tungsten oxide or molybdenum oxide;

[0223] 1,4,5,8,9,12-hexaazabenzophenanthrene-hexanitrile (HAT-CN); and

[0224] The compound represented by formula 221,

[0225] However, the embodiments disclosed herein are not limited thereto:

[0226]

[0227] <Formula 221>

[0228]

[0229] In Equation 221,

[0230] R 221 To R 223 Each can be independently selected from substituted or unsubstituted C3-C. 10cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, wherein R 221 To R 223 At least one of them may have at least one substituent selected from the following: cyano, -F, -Cl, -Br, -I, C1-C substituted with -F. 20 Alkyl groups, C1-C substituted with -Cl 20 Alkyl groups, C1-C substituted with -Br 20 Alkyl groups and -I-substituted C1-C 20 alkyl.

[0231] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer can be patterned as a red emission layer, a green emission layer, or a blue emission layer according to the sub-pixels. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from red, green, and blue emission layers, wherein the two or more layers are in contact with or separated from each other. In one or more embodiments, the emission layer may include two or more materials selected from red, green, and blue luminescent materials, wherein the two or more materials are mixed with each other in a single layer to emit white light.

[0232] The emitting layer may include a host and a dopant. The dopant may include at least one selected from phosphorescent dopant and fluorescent dopant.

[0233] Based on 100 parts by weight of the main body, the amount of dopant in the emitter layer can generally be in the range of about 0.01 parts by weight to about 15 parts by weight, but the embodiments of this disclosure are not limited thereto.

[0234] The thickness of the emission layer can be approximately to approximately For example, about to approximately Within this range, excellent light-emitting characteristics can be obtained without a significant increase in driving voltage when the thickness of the emitting layer is within this range.

[0235] In one or more embodiments, the body may include a compound represented by the following formula 301:

[0236] <Formula 301>

[0237] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .

[0238] In Equation 301,

[0239] Ar 301 C5-C can be substituted or unsubstituted. 60 C1-C with or without substituted carbocyclic groups 60 Heterocyclic group,

[0240] xb11 can be 1, 2, or 3.

[0241] L 301 It can be selected from substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups;

[0242] xb1 can be an integer from 0 to 5.

[0243] R 301 It can be selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -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 ).

[0244] xb21 can be an integer from 1 to 5, and

[0245] Q 301 To Q 303 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, but the embodiments disclosed herein are not limited thereto.

[0246] In one implementation, in formula 301, Ar 301 You can choose from:

[0247] Naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthreneyl, anthraceneyl, fluoranthraceneyl, benzo[a]phenanthreneyl, pyreneyl alkyl, tetraphenyl, francyl, perylene, penfenyl, indanethenyl, dibenzofuranyl and dibenzothiophenyl; and

[0248] Each of the following is substituted with at least one of the following: naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenerenoyl, anthraceneyl, fluoranthraceneyl, benzo[a]phenanthryl, pyreneyl. alkyl, tetraphenyl, lavany, perylene, penfenyl, indoxaneyl, dibenzofuranyl and dibenzothiophene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -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

[0249] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl. However, the embodiments disclosed herein are not limited thereto.

[0250] When xb11 in Equation 301 is 2 or greater, two or more Ar301 can be connected by a single bond.

[0251] In one or more embodiments, the compound represented by formula 301 may be represented by formula 301-1 or formula 301-2:

[0252] <Formula 301-1>

[0253]

[0254] <Formula 301-2>

[0255]

[0256] In Equations 301-1 and 301-2,

[0257] A 301 To A 304 Each can be independently selected from phenyl, naphthyl, phenanthryl, fluoranyl, benzo[a]phenanthryl, pyrene, alkyl, pyridyl, pyrimidinyl, indyl, fluorenyl, spiro-difluorenyl, benzo[fluorenyl], dibenzo[fluorenyl], indolyl, carbazoleyl, benzo[carbazoleyl], dibenzo[carbazoleyl], furanyl, benzo[furanyl], dibenzo[furanyl], naphthofuranyl, benzo[naphthofuranyl], dinaphthofuranyl, thiophenyl, benzo[thiophenyl], dibenzo[thiophenyl], naphtho[thiophenyl], benzo[naphtho[thiophenyl], and dinaphtho[thiophenyl]

[0258] X 301 It can be O, S or N-[(L 304 ) xb4 -R 304 ],

[0259] R 311 To R 314 Each can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -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 ),

[0260] xb22 and xb23 can each be 0, 1, or 2 independently.

[0261] L 301 xb1, R 301 and Q 31 To Q 33 As described above,

[0262] L 302 To L 304 Each can be independently combined with L 301 The same as described.

[0263] xb2 to xb4 can each be independently identical to the one described in combination with xb1, and

[0264] R 302 To R 304 They can be used independently with R 301 same,

[0265] For example, in equations 301, 301-1, and 301-2, L 301 To L 304 Each can be selected independently from:

[0266] Phenylidene, naphthylene, fluorene, spiro-difluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluoranthracene, benzo[a]phenanthrene, pyrene, etc. Perylene, pentafenyl, hexaphenylene, pentaphenylene, phenylthioene, furanylene, carbazoylene, indoleylene, isoindoleylene, benzofuranylene, benzobenzenethioene, dibenzofuranylene, dibenzobenzenethioene, benzocarbazoylene, dibenzocarbazoylene, dibenzosiloxanediylene, pyridinylene, imidazoylene, pyrazolylene, thiazoylene, isothiazolylene, oxazolylene, isoxazolylene, thiazolylene, oxadiazoleene , pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthrene-pyridinyl, acridineyl, phenanthrene-pyridinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl; and

[0267] Each of the following is substituted with at least one of the following: phenylene, naphthylene, fluorene, spiro-difluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluoranthracene, benzo[a]phenanthrene, pyrene, etc. Perylene, pentafenyl, hexaphenylene, pentaphenylene, phenylthioene, furanyl, carbazoyl, indoleyl, isoindoleyl, benzofuranyl, benzobenzenthioene, dibenzofuranyl, dibenzobenzenthioene, benzocarbazoyl, dibenzocarbazoyl, dibenzosiloxanedienyl, pyridinyl, imidazoyl, pyrazolyl, thiazoyl, isothiazolyl, oxazolyl, isoxazolyl, thiazodiazoleyl, oxadiazoleyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridazinyl, pyridazinyl Triazinyl, quinolineyl, isoquinolineyl, benzoquinolineyl, phthalazinyl, naphthidyl, quinoxalinyl, quinoxalinyl, phenanthrynyl, acridineyl, phenanthrynyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, and zazacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranyl, benzo[a]phenanthryl, pyrene Peryl, pentylenyl, hexaphenyl, pentaphenyl, phenylthio, furanyl, carbazole, indole, isoindole, benzofuranyl, benzophenylthio, dibenzofuranyl, dibenzophenylthio, benzocarbazole, dibenzocarbazole, dibenzosilylonoprene, pyridinyl, imidazole, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -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

[0268] Q 31 To Q 33 It can be the same as described above.

[0269] In one embodiment, in formulas 301, 301-1, and 301-2, R 301 To R 304 Each can be selected independently from:

[0270] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranthraceneyl, benzo[a]phenanthryl, pyrene Peryl, pentylenyl, hexaphenyl, pentaphenyl, phenylthio, furanyl, carbazole, indole, isoindole, benzofuranyl, benzophenylthio, dibenzofuranyl, dibenzophenylthio, benzocarbazole, dibenzocarbazole, dibenzosilylonoprene, pyridinyl, imidazole, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazole, oxadiazole alkyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0271] Each of the following is substituted with at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranthraceneyl, benzo[a]phenanthryl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, phenylthio, furanyl, carbazole, indole, isoindole, benzofuranyl, benzobenzenthio, dibenzofuranyl, dibenzobenzenthio, benzocarbazole, dibenzocarbazole, dibenzosiloxanepentadienyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl Quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cenolinyl, phenanthridine, acridineyl, phenanthrolinel, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranyl, benzo[a]phenanthryl, pyrene Peryl, pentylenyl, hexaphenyl, pentaphenyl, phenylthio, furanyl, carbazole, indole, isoindole, benzofuranyl, benzophenylthio, dibenzofuranyl, dibenzophenylthio, benzocarbazole, dibenzocarbazole, dibenzosilylonoprene, pyridinyl, imidazole, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -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

[0272] Q 31 To Q 33It can be the same as described above.

[0273] 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), Mg complexes, and Zn complexes.

[0274] The main body may include at least one selected from 9,10-bis(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthyl-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(carbazolyl-9-yl)benzene (TCP) and compounds H1 to H55, but the embodiments of this disclosure are not limited thereto:

[0275]

[0276]

[0277]

[0278] Phosphorescent dopants may include those known in the art.

[0279] Fluorescent dopants may include compounds represented by Formula 1, or may include fluorescent dopants known in the art.

[0280] The electron transport region may have i) a single-layer structure comprising a single layer of a single material, ii) a single-layer structure comprising a single layer of multiple different materials, or iii) a multi-layer structure comprising multiple layers of multiple different materials.

[0281] 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 this disclosure are not limited thereto.

[0282] 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 for each structure, the constituent layers are stacked sequentially from the emitter layer. However, the implementation of the electron transport region structure is not limited to this.

[0283] The electron transport region (e.g., a buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may include a metal-free compound containing at least one nitrogen-containing ring that has depleted π electrons.

[0284] "A nitrogen-containing ring with depleted π electrons" refers to a C1-C ring with at least one *-N=*' moiety as the cyclic part. 60 Heterocyclic group.

[0285] For example, a "π-electron-depleted nitrogen-containing ring" can be i) a five- to seven-membered heteromonocyclic group having at least one *-N=*' moiety, ii) a heteropolycyclic group, wherein two or more five- to seven-membered heteromonocyclic groups each having at least one *-N=*' moiety are fused together, or iii) a heteropolycyclic group, wherein at least one five- to seven-membered heteromonocyclic group each having at least one *-N=*' moiety is fused with at least one C5-C5 carbon cyclic group.

[0286] Examples of nitrogen-containing rings that are depleted of π electrons include, but are not limited to, imidazoles, pyrazoles, thiazoles, isothiazoles, oxazoles, isoxazoles, pyridines, pyrazines, pyrimidines, pyridazines, indazoles, purines, quinoline, isoquinoline, benzoquinoline, phthalazines, naphthidine, quinoxaline, quinazoline, cyclophosphine, phenanthridine, acridine, phenanthridine, phenazine, benzimidazole, isobenzothiazole, benzoxazole, isobenzoxazole, triazoles, tetraazoles, oxadiazoles, triazines, thiadiazoles, imidazopyridines, imidazopyrimidines, and azacarbazoles.

[0287] For example, the electron transport region may include a compound represented by formula 601:

[0288] <Formula 601>

[0289] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .

[0290] In Equation 601,

[0291] Ar 601 C5-C can be substituted or unsubstituted. 60 C1-C with or without substituted carbocyclic groups 60 Heterocyclic group,

[0292] xe11 can be 1, 2, or 3.

[0293] L 601 It can be selected from substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups;

[0294] xe1 can be an integer from 0 to 5.

[0295] R 601 C3-C can be self-substituted or unsubstituted. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -Si(Q 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q) 601 ) and -P(=O)(Q 601 (Q) 602 ),

[0296] Q 601 To Q 603 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, and

[0297] xe21 can be an integer from 1 to 5.

[0298] In one implementation, the quantity of Ar is xe11 601 and R with a quantity of xe21 601 At least one of them may include a nitrogen-containing ring that has depleted π electrons.

[0299] In one implementation, the ring Ar in formula 601 601 You can choose from:

[0300] Phenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrene, anthracene, fluoranyl, benzo[a]phenanthrene, pyrene alkyl, tetraphenyl, francyl, perylene, penfenyl, indoxanthracene, dibenzofuranyl, dibenzothiopheneyl, carbazoyl, imidazoyl, pyrazolyl, thiazoyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazoleyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazoyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl and azacarbazoyl; and

[0301] Each of the following is substituted with at least one of the following: phenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthreneyl, anthraceneyl, fluoranthraceneyl, benzo[a]phenanthreneyl, pyreneyl, alkyl, tetraphenyl, francyl, perylene, penfenyl, indoxanel, dibenzofuranyl, dibenzothiophenyl, carbazole, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, zoline alkyl, phenanthridine, acridine, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q) 31 (Q) 32 (Q) 33 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 ),and

[0302] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0303] When xe11 in equation 601 is 2 or greater, two or more Ar 601 It can be connected with a single button.

[0304] In one or more embodiments, Ar in Formula 601 601 It can be anthracene-based.

[0305] In one or more embodiments, the compound represented by formula 601 may be represented by formula 601-1:

[0306] <Formula 601-1>

[0307]

[0308] In Equation 601-1,

[0309] X 614 It can be N or C(R) 614 ), X 615 It can be N or C(R) 615 ), X 616 It can be N or C(R) 616 ), and selected from X 614 To X 616 At least one of them can be N,

[0310] L 611 To L 613 Each can be independently combined with L 601 The same as described.

[0311] xe611 to xe613 can each independently be identical to the one described in conjunction with xe1.

[0312] R 611 To R 613 Each can independently combine with R 601 The descriptions are the same.

[0313] R 614 To R 616 Each can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0314] In one implementation, in formulas 601 and 601-1, L 601 and L 611 To L 613 Each can be selected independently from:

[0315] Phenylidene, naphthylene, fluorene, spiro-difluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluoranthracene, benzo[a]phenanthrene, pyrene, etc. Perylene, pentafenyl, hexaphenylene, pentaphenylene, phenylthioene, furanylene, carbazoylene, indoleylene, isoindoleylene, benzofuranylene, benzobenzenethioene, dibenzofuranylene, dibenzobenzenethioene, benzocarbazoylene, dibenzocarbazoylene, dibenzosiloxanediylene, pyridinylene, imidazoylene, pyrazolylene, thiazoylene, isothiazolylene, oxazolylene, isoxazolylene, thiazolylene, oxadiazoleene , pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthrene-pyridinyl, acridineyl, phenanthrene-pyridinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl; and

[0316] Each of the following is substituted with at least one of the following: phenylene, naphthylene, fluorene, spiro-difluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluoranthracene, benzo[a]phenanthrene, pyrene, etc. Perylene, pentafenyl, hexaphenylene, pentaphenylene, phenylthioene, furanyl, carbazoyl, indoleyl, isoindoleyl, benzofuranyl, benzobenzenthioene, dibenzofuranyl, dibenzobenzenthioene, benzocarbazoyl, dibenzocarbazoyl, dibenzosiloxanedienyl, pyridinyl, imidazoyl, pyrazolyl, thiazoyl, isothiazolyl, oxazolyl, isoxazolyl, thiazodiazoleyl, oxadiazoleyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridazinyl, pyridazinyl Triazinyl, quinolineyl, isoquinolineyl, benzoquinolineyl, phthalazinyl, naphthidyl, quinoxalinyl, quinoxalinyl, phenanthrynyl, acridineyl, phenanthrynyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, and zazacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranyl, benzo[a]phenanthryl, pyrene Peryl, pentylenyl, hexaphenyl, pentaphenyl, phenylthio, furanyl, carbazole, indole, isoindole, benzofuranyl, benzophenylthio, dibenzofuranyl, dibenzophenylthio, benzocarbazole, dibenzocarbazole, dibenzosilylopadienyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl The compounds used include, but are not limited to, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cyclolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, and azacarbazolyl, but the embodiments disclosed herein are not limited to these.

[0317] In one or more embodiments, in formulas 601 and 601-1, xe1 and xe611 to xe613 can each be 0, 1 or 2 independently.

[0318] In one or more embodiments, in formulas 601 and 601-1, R 601 and R 611 To R 613 Each can be selected independently from:

[0319] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranthraceneyl, benzo[a]phenanthryl, pyrene Peryl, pentylenyl, hexaphenyl, pentaphenyl, phenylthio, furanyl, carbazole, indole, isoindole, benzofuranyl, benzophenylthio, dibenzofuranyl, dibenzophenylthio, benzocarbazole, dibenzocarbazole, dibenzosilylonoprene, pyridinyl, imidazole, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Azolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cyclolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl;

[0320] Each of the following is substituted with at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranthraceneyl, benzo[a]phenanthryl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, phenylthio, furanyl, carbazole, indole, isoindole, benzofuranyl, benzobenzenthio, dibenzofuranyl, dibenzobenzenthio, benzocarbazole, dibenzocarbazole, dibenzosiloxanepentadienyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl Quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cenolinyl, phenanthridine, acridineyl, phenanthrolinel, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranyl, benzo[a]phenanthryl, pyrene Peryl, pentylenyl, hexaphenyl, pentaphenyl, phenylthio, furanyl, carbazole, indole, isoindole, benzofuranyl, benzophenylthio, dibenzofuranyl, dibenzophenylthio, benzocarbazole, dibenzocarbazole, dibenzosilylopyronyl, pyridinyl, imidazole, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazole, oxadiazole alkyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0321] -S(=O)2(Q 601 ) and -P(=O)(Q 601 (Q) 602 ),

[0322] Q 601 and Q 602 Same as described above.

[0323] The electron transport region may include at least one compound selected from compounds ET1 to ET36, but embodiments of this disclosure are not limited thereto:

[0324]

[0325]

[0326]

[0327] In one or more embodiments, the electron transport region may include at least one 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.

[0328]

[0329] The thickness of the buffer layer, hole blocking layer, or electronic control layer can be approximately to approximately For example, about to approximately Within these ranges, when the thicknesses of the buffer layer, hole blocking layer, and electron control layer are within these ranges, the electron blocking layer can exhibit excellent electron blocking or electron control characteristics without a significant increase in driving voltage.

[0330] The thickness of the electron transport layer can be approximately to approximately For example, about to approximately Within the aforementioned range, when the thickness of the electron transport layer is within this range, the electron transport layer can exhibit satisfactory electron transport characteristics without a significant increase in driving voltage.

[0331] In addition to the materials mentioned above, the electron transport region (e.g., the electron transport layer in the electron transport region) may also include a metallic material.

[0332] The metal-containing material may include at least one selected from alkali metal complexes and alkaline earth metal complexes. Alkali metal complexes may include metal ions selected from Li ions, Na ions, K ions, Rb ions, and Cs ions, and alkaline earth metal complexes may include metal ions selected from Be ions, Mg ions, Ca ions, Sr ions, and Ba ions. The ligands coordinating with the metal ions of the alkali metal complex or alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenidine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but the embodiments disclosed herein are not limited thereto.

[0333] For example, metal-containing materials may include Li complexes. Li complexes may include, for example, compounds ET-D1 (lithium quinoline, LiQ) or ET-D2:

[0334]

[0335] The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.

[0336] 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 including a plurality of different materials.

[0337] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0338] 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 embodiments, the alkali metal may be Li or Cs, but embodiments of the present disclosure are not limited thereto.

[0339] The alkaline earth metal may be selected from Mg, Ca, Sr and Ba.

[0340] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb and Gd.

[0341] The alkali metal compound, alkaline earth metal compound and rare earth metal compound may be selected from oxides and halides (e.g., fluorides, chlorides, bromides or iodides) of alkali metals, alkaline earth metals and rare earth metals.

[0342] The alkali metal compound may be selected from alkali metal oxides (such as Li₂O, Cs₂O or K₂O) and alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI or KI). In one embodiment, the alkali metal compound may be selected from LiF, Li₂O, NaF, LiI, NaI, CsI and KI, but embodiments of the present disclosure are not limited thereto.

[0343] The alkaline earth metal compound may be selected from alkaline earth metal oxides, such as BaO, SrO, CaO, Ba x Sr 1-x O (0<x<1) or Ba x Ca 1-x O (0<x<1). In one embodiment, the alkaline earth metal compound may be selected from BaO, SrO and CaO, but embodiments of the present disclosure are not limited thereto.

[0344] The rare earth metal compound may be selected from YbF3, ScF3, ScO3, Y2O3, Ce2O3, GdF3, and TbF3. In one embodiment, the rare earth metal compound may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, or TbI3, but the embodiments disclosed herein are not limited thereto.

[0345] Alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may respectively include the aforementioned alkali metal ions, alkaline earth metal ions, and rare earth metal ions. Furthermore, the ligands that coordinate 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, hydroxyphenidine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene. However, the embodiments disclosed herein are not limited to these.

[0346] The electron injection layer may consist of the following: alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof. In one or more embodiments, the electron injection layer may further include organic materials. When the electron injection layer further includes organic materials, the alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof may be uniformly or non-uniformly dispersed in the matrix comprising the organic material.

[0347] The thickness of the electron injection layer can be approximately to approximately For example, about to approximately Within the aforementioned range, when the thickness of the electron injection layer is within this range, the electron injection layer can exhibit satisfactory electron injection characteristics without a significant increase in driving voltage.

[0348] The second electrode 190 can be disposed on the organic layer 150 having such a structure. The second electrode 190 can be a cathode, which is an electron injection electrode, and in this respect, the material used to form the second electrode 190 can be a material with low work function, and such material can be a metal, alloy, conductive compound, or combination thereof.

[0349] The second electrode 190 may include 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 this disclosure are not limited thereto. The second electrode 190 may be a transmission electrode, a semi-transmission electrode, or a reflection electrode.

[0350] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.

[0351] Figure 2 The organic light-emitting device 20 includes a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190 stacked sequentially. Figure 3 The organic light-emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 stacked sequentially. Figure 4 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 stacked sequentially.

[0352] for Figures 2 to 4 It can be combined with reference Figure 1 The proposed description is used to understand the first electrode 110, the organic layer 150, and the second electrode 190.

[0353] In the organic layer 150 of each organic light-emitting device 20 and 40, the light generated in the emission layer can pass through the first electrode 110 (which is a semi-transparent electrode or a transmissive electrode) and the first capping layer 210 toward the outside, and in the organic layer 150 of each organic light-emitting device 30 and 40, the light generated in the emission layer can pass through the second electrode 190 (which is a semi-transparent electrode or a transmissive electrode) and the second capping layer 220 toward the outside.

[0354] According to the principle of constructive interference, the first capping layer 210 and the second capping layer 220 can increase the external luminescence efficiency.

[0355] The first capping layer 210 and the second capping layer 220 can each be an organic capping layer including organic materials, an inorganic capping layer including inorganic materials, or a composite capping layer including organic and inorganic materials.

[0356] At least one of the first capping layer 210 and the second capping layer 220 may each independently comprise at least one material selected from the following: carbocyclic compounds, heterocyclic compounds, amine compounds, porphyrin derivatives, phthalocyanine derivatives, naphthylphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds, and amine compounds may optionally be substituted with substituents containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I.

[0357] In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include an amine compound.

[0358] In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include a compound represented by formula 201 or a compound represented by formula 202.

[0359] In one or more embodiments, at least one of the first capping layer 210 and the second capping layer 220 may each independently include a compound selected from compounds HT28 to HT33 and compounds CP1 to CP5, but embodiments of this disclosure are not limited thereto:

[0360]

[0361] In the above text, it has already been combined Figure 1-4 An organic light-emitting device according to an embodiment has been described. However, the embodiments disclosed herein are not limited thereto.

[0362] The layers constituting the hole transport region, the emitter layer, and the electron transport region can be formed in a region using one or more suitable methods, selected from vacuum deposition, spin coating, casting, Langmuir-Brookett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.

[0363] When each layer constituting the hole transport region, the emitter layer, and each layer constituting the electron transport region are formed by vacuum deposition, taking into account the materials to be included in the layers to be formed and the structure of the layers to be formed, the vacuum deposition can be performed, for example, at a deposition temperature of about 100°C to about 500°C, and at a deposition temperature of about 10... -8 To about 10 -3 The vacuum pressure of Tor and about / seconds to approximately The deposition was carried out at a deposition rate of / second.

[0364] When the layers constituting the hole transport region, the emitter layer, and the electron transport region are formed by spin coating, depending on the material to be included in the layers and the structure of each layer to be formed, spin coating can be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80°C to 200°C.

[0365] As used in this article, the term "C1-C" 60 "alkyl" refers to a monovalent group of a straight-chain or branched saturated aliphatic hydrocarbon having 1 to 60 carbon atoms, and non-limiting examples include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. The term "C1-C" is used herein. 60 "alkylene" refers to C1-C 60 Alkyl groups have the same structure as divalent groups.

[0366] As used in this article, the term "C2-C" 60 "Alkenyl" refers to a group formed by the combination of C2-C... 60 A hydrocarbon group formed by substituting at least one carbon-carbon double bond into the middle or end of an alkyl group, and non-limiting examples include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" is used in this context. 60 "Alkenyl" refers to C2-C 60 Alkenes have divalent groups with the same structure.

[0367] As used in this article, the term "C2-C" 60 "Alkyne group" refers to the group formed by the combination of C2-C... 60 A hydrocarbon group formed by substituting at least one carbon-carbon triple bond into the middle or end of an alkyl group, and non-limiting examples include ethynyl and propynyl groups. As used herein, the term "C2-C" is used in this context. 60 "Immyneyl" refers to C2-C 60 The alkynyl group is a divalent group with the same structure.

[0368] As used in this article, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 Alkyl groups are monovalent groups, and non-limiting examples include methoxy, ethoxy, and isopropoxy.

[0369] As used in this article, the term "C3-C" 10 "Cycloalkyl" refers to a monocyclic saturated hydrocarbon group having 3 to 10 carbon atoms, and non-limiting examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. The term "C3-C" is used herein. 10 "Cycloalkylene" refers to C3-C 10 Cycloalkyl groups have the same divalent structure.

[0370] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom and 1 to 10 carbon atoms, and non-limiting examples include 1,2,3,4-oxatriazolyl, tetrahydrofuranyl, and tetrahydrophenylthioyl. The term "C1-C" as used herein is also used. 10 "Heterocyclic alkyl" refers to C1-C 10 Heterocyclic alkyl groups have divalent groups with the same structure.

[0371] As used in this article, the term "C3-C" 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and not being aromatic, and non-limiting examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. The term "C3-C" is used herein. 10 "Biopylene" refers to C3-C 10 Cycloalkenyl groups are divalent groups with the same structure.

[0372] As used in this article, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom, 1 to 10 carbon atoms, and at least one double bond in its ring. C1-C 10 Non-limiting examples of heterocyclic alkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl" refers to C1-C 10 Heterocyclic alkenyl groups are divalent groups with the same structure.

[0373] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system (with 6 to 60 carbon atoms), and as used herein, "C6-C" 60 "Arylene" refers to a divalent group that has a carbocyclic aromatic system (with 6 to 60 carbon atoms). C6-C 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, and Base. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, the rings can fused together.

[0374] As used in this article, the term "C1-C" 60"Heteroaryl" refers to a monovalent group that has a heterocyclic aromatic system (having at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom in addition to 1 to 60 carbon atoms). The term "C1-C" is used herein. 60 "Hypo-heteroaryl" refers to a divalent group that has a heterocyclic aromatic system (having at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom in addition to 1 to 60 carbon atoms). C1-C 60 Non-limiting examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C1-C... 60 heteroaryl and C1-C 60 When each heteroaryl group comprises two or more rings, the rings can fused together.

[0375] As used in this article, the term "C6-C" 60 "Aryloxy group" refers to -OA 102 (where A) 102 For C6-C 60 (aryl), and the term C6-C as used herein. 60 Arylthioyl group represents -SA 103 (where A) 103 For C6-C 60 Aryl).

[0376] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings fused together, with only carbon atoms as cyclic atoms, and the entire molecular structure being non-aromatic. A specific example of a monovalent nonaromatic fused polycyclic group is the fluorene group. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused polycyclic group.

[0377] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group (e.g., having 1 to 60 carbon atoms) having two or more rings fused together, having at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom in addition to carbon atoms, and whose overall molecular structure is not aromatic. An example of a monovalent nonaromatic fused heterocyclic group is the carbazoyl group. As used herein, the term "divalent nonaromatic fused heterocyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused heterocyclic group.

[0378] As used in this article, the term "C5-C" 60 A "carbocyclic group" refers to a monocyclic or polycyclic group with 5 to 60 carbon atoms, in which the cyclic atom is only a carbon atom. (C5-C) 60 The carbocyclic group can be an aromatic carbocyclic group or a non-aromatic carbocyclic group. C5-C60 The carbocyclic group can be a ring (e.g., benzene), a monovalent group (e.g., phenyl), or a divalent group (e.g., phenylene). In one or more embodiments, depending on the connection to C5-C... 60 The number of substituents in the carbocyclic group, C5-C 60 The carbon cyclic group can be a trivalent or tetravalent group.

[0379] As used in this article, the term "C1-C" 60 "Heterocyclic group" refers to a group related to C1-C 60 A carbocyclic group has the same structure, except that, in addition to carbon (the number of carbon atoms can range from 1 to 60), it uses at least one heteroatom selected from N, O, Si, P and S as the cyclic atom.

[0380] Replacement C5-C 60 Carbocyclic groups, substituted C1-C 60 Heterocyclic groups, substituted C3-C 10 Cycloalkylene, substituted C1-C 10 Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 aryl, substituted C1-C 60 Heteroaryl groups, substituted divalent nonaromatic fused polycyclic groups, substituted divalent nonaromatic fused heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthio, substituted C1-C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group may be selected from:

[0381] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;

[0382] Each is substituted by at least one of the following C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 ) and -P(=O)(Q 11 (Q) 12 );

[0383] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups;

[0384] Each is replaced by at least one of the following C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) and -P(=O)(Q 21 (Q) 22 );as well as

[0385] -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

[0386] Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, biphenyl and terphenyl.

[0387] As used herein, the term “Ph” may refer to phenyl, as used herein, the term “Me” may refer to methyl, as used herein, the term “Et” may refer to ethyl, as used herein, the terms “ter-Bu” or “But” may refer to tert-butyl, and as used herein, the term “OMe” may refer to methyloxy.

[0388] As used in this article, the term "biphenyl" refers to a phenyl group that has been substituted with a phenyl group. In other words, "biphenyl" is a phenyl group with a C6-C2 bond. 60 Aryl groups are substituted phenyl groups.

[0389] As used herein, the term "terphenyl" refers to a "phenyl group substituted with a biphenyl group." In other words, "terphenyl" is a C6-C6 aryl group with a C6-C6 substituted aryl group. 60 Aleyl group is a substituent for phenyl groups.

[0390] Unless otherwise defined, * and *' as used herein refer to the binding site with a neighboring atom in the corresponding formula.

[0391] In the following description, the compounds according to the embodiments and the organic light-emitting devices according to the embodiments will be described in detail with reference to the synthesis examples and embodiments. The expression "using B instead of A" used in the description of the synthesis examples means using the same molar equivalent of B instead of A.

[0392] [Synthesis example]

[0393] (1) Synthesis Example 1: Synthesis of Intermediate 1-1

[0394]

[0395] 2 g (7.22 mmol) of 4-bromo-1,8-naphthalene anhydride was dissolved in 30 mL of ethanol, and dimethylamine (236 mg, 7.94 mmol) was added to the solution. The reaction solution was refluxed and stirred for 3 hours. After the reaction was complete, the reaction solution was cooled to room temperature. The precipitated solid was then filtered to obtain 1.98 g (94% yield) of intermediate 1-1 as a white solid.

[0396] 1H NMR (300MHz, CDCl3) δ8.61(d,J=8.4Hz,2H),8.45(dd,J=8.4,2.1Hz,2H),8.42(s,2H),8.10(d,J=8.0Hz,2H),7.92–7.8 1(m,J=14.9,7.9Hz,4H),7.70(d,J=5.3Hz,2H),7.12(t,J=7.1Hz,2H),7.02(t,2H),6.98(t,2H),6.44(d,J=7.4Hz,2H).

[0397] (2) Synthesis Example 2: Synthesis of Intermediate 2-1

[0398]

[0399] 0.6 g (2.166 mmol) of 4-bromo-1,8-naphthalene anhydride, 3,5-bis(trifluoromethyl)aniline (3.248 mmol), and zinc acetate (3.47 mmol) were added to a round-bottom flask containing argon gas. 15 mL of quinoline was added, and the mixture was refluxed and stirred at 180 °C for 24 hours. After the reaction was complete, the reaction solution was cooled to room temperature. Extraction with water and dichloromethane was performed to obtain an organic layer. The organic layer was dried and then purified by column chromatography to remove impurities. Recrystallization from the organic layer using methanol and chloroform yielded 650 mg of product.

[0400] The following synthetic method demonstrates, by taking as an example a compound in which the methyl group at the nitrogen position of the naphthalimide (intermediate 1-1) synthesized in Synthetic Example 1 is substituted, that other aliphatic or aromatic compounds can be substituted at the nitrogen position.

[0401] (3) Synthesis Example 3: Synthesis of Compound 2

[0402]

[0403] 0.4 g (1.4 mmol) of intermediate 1-1 was dissolved in 18 mL of toluene, and 0.525 g (1.6 mmol) of 10H-spiro[acridin-9,9'-fluorene], 0.265 g (2.8 mmol) of sodium tert-butoxide, and 0.05 g (0.1 mmol) of bis(tri-tert-butylphosphine)palladium(0) were added. The reaction solution was refluxed and stirred at 100 °C for 14 hours under an argon atmosphere. After the reaction was complete, water was added, and the solution was extracted with dichloromethane. The extracted organic layer was dried over anhydrous MgSO4 to evaporate the solvent. The residue obtained was purified by silica gel column chromatography using a 1:4 mixture of ethyl acetate and n-hexane as the mobile phase. The residue was then recrystallized from dichloromethane and methanol to give 0.145 g (yield: 20%) of compound 2.

[0404] 1 H NMR (500 MHz, DMSO) δ 10.01 (d, J = 1.7 Hz, 2H), 8.81 (dd, J = 8.3, 1.8 Hz, 2H), 8.76 (d, J = 8.4 Hz, 2H).

[0405] (4) Synthesis Example 4: Synthesis of Compound 3

[0406]

[0407] 0.135 g (0.47 mmol) of intermediate 1-1 was dissolved in 5 mL of toluene, and 0.18 g (0.52 mmol) of diphenyl azasiline, 0.09 g (0.94 mmol) of sodium tert-butoxide, and 0.017 g (0.032 mmol) of bis(tri-tert-butylphosphine)palladium(0) were added. The reaction solution was refluxed and stirred at 100 °C for 14 hours under an argon atmosphere. After the reaction was complete, water was added, and the solution was extracted with dichloromethane. The extracted organic layer was dried over anhydrous MgSO4 to evaporate the solvent. The residue obtained was purified by silica gel column chromatography using a 1:4 mixture of ethyl acetate and n-hexane as the mobile phase. The residue was then recrystallized from dichloromethane and methanol to give 0.15 g (yield: 57%) of compound 3 as a yellow solid.

[0408] 1 H NMR (500 MHz, DMSO) δ 10.01 (d, J = 1.7 Hz, 2H), 8.81 (dd, J = 8.3, 1.8 Hz, 2H), 8.76 (d, J = 8.4 Hz, 2H).

[0409] The compounds synthesized according to Synthesis Example 3 and Synthesis Example 41 The H NMR results are shown in Table 1.

[0410] In addition to the compounds shown in Table 1, those skilled in the art can easily learn about other compounds by referring to the above-described synthetic methods and raw materials.

[0411] [Table 1]

[0412]

[0413] [Evaluation Example]

[0414] Example 1 and Evaluation Example 1: Characteristic Evaluation of TADF Compounds

[0415] 1,3-Bis(9H-carbazole-9-yl)benzene (mCP) and compound 2 were mixed in a 20:1 ratio, and then the mixture was dissolved in 1,2-dichloroethane. The resulting solution was spin-coated onto quartz for the following measurements:

[0416] <mcp>

[0417]

[0418] The HOMO level was measured by cyclic voltammetry (CV). The LUMO level was measured by calculating the optical band gap from the HOMO level. Additionally, the triplet T1 level was measured using 77K PL spectroscopy. The absolute photoluminescence quantum yield (AbPLQY) was measured by coating a film doped with compound 2 at a concentration of 2.5 wt%. The measurement results are shown in Table 2.

[0419] [Table 2]

[0420]

[0421] Example 2 and Evaluation Example 2:

[0422] For the compounds synthesized according to Synthesis Examples 3 and 4, AbPLQY was measured using films coated with CBP doped with each of Compound 2 and Compound 3 at a concentration of 4.8 wt%, and exciton lifetime was measured according to the time-correlated single-photon counting (TCSPC) method.

[0423] [Table 3]

[0424]

[0425] Example 3

[0426] As the ITO anode, an ITO glass substrate (25mm × 25mm, 15Ω / cm) will be used in the organic light-emitting device. 2 The glass substrate (manufactured by Samsung Corning) was ultrasonically treated sequentially with distilled water and isopropanol, followed by cleaning with exposure to ultraviolet light and ozone for approximately 30 minutes. The resulting glass substrate was then mounted on a substrate holder in a vacuum deposition apparatus. N,N'-bis(naphthyl-1-yl)-N,N'-bis(phenyl)benzidine (NPB) was deposited on the ITO electrode (anode) to form a hole transport layer with a thickness of 40 nm. CBP and compound 2 (10 wt%) were co-deposited on the hole transport layer to form an emission layer with a thickness of 20 nm, and 2,2',2”-(1,3,5-phenyltriyl)-tris(1-phenyl-1H-benzimidazole) (TPBi) was deposited on the emission layer to form an electron transport layer with a thickness of 40 nm. LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 0.7 nm, and Al was deposited on the electron injection layer to form a cathode with a thickness of 100 nm, thus completing the fabrication of the organic light-emitting device. The equipment used for deposition was a Suicel plus 200 evaporator manufactured by SunicSystem Company.

[0427] <npb>

[0428]

[0429] <cbp>

[0430]

[0431] <tpbi>

[0432]

[0433] Example 4

[0434] The organic light-emitting device was manufactured in the same manner as in Example 3, except that compound 3 was used instead of compound 2.

[0435] Evaluation Example 3

[0436] The driving voltage, efficiency, and color coordinates of each organic light-emitting device manufactured according to Examples 3 and 4 were measured as follows, and the results are shown in Table 4:

[0437] - Color coordinates: Powered by a current-voltmeter (Kethley SMU 236) and measured using a luminance meter (PR650).

[0438] -Brightness: Powered by a current-voltmeter (Kethley SMU 236) and measured using a luminance meter (PR650).

[0439] - Efficiency: Powered by a current-voltmeter (Kethley SMU 236) and measured using a luminance meter (PR650).

[0440] [Table 4]

[0441]

[0442] According to one or more embodiments, organic light-emitting devices comprising heterocyclic compounds can have low driving voltage, high efficiency, long lifetime and high maximum quantum efficiency.

[0443] It should be understood that the embodiments described herein are descriptive in nature and not for limiting purposes. The description of features or aspects in each embodiment should generally be understood as applicable to other similar features or aspects in other embodiments.

[0444] Although one or more embodiments have been described with reference to the accompanying drawings, those skilled in the art will understand that various changes in form and detail may be made therein without departing from the spirit and scope defined by the following claims.< / tpbi> < / cbp> < / npb> < / mcp>

Claims

1. A heterocyclic compound, said heterocyclic compound being represented by formula 1-2: <Equation 1-2> ， in, In Equation 1-2, X3 is a single key. A1 and A2 are each independently selected from: Phenyl, naphthyl, fluorenyl, phenanthryl, anthraceneyl, pyreneyl, and thionyl; and Each of the following is substituted with at least one of the following: phenyl, naphthyl, fluorenyl, phenanthryl, anthraceneyl, pyreneyl, and hydroxyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, fluorenyl, spirofluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene, phenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, and triazinyl. R 51 and R 52 Each group is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, and hydrazone. b51 and b52 are each independent integers from 0 to 5, where when b51 is 2 or greater, two or more R... 51 They are the same or different from each other, and when b52 is 2 or greater, two or more R 52 Whether they are the same or different, L1 is a single bond. a1 is 1. R1, R2 and R 11 To R 18 Each group is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, and hydrazone. R3 represents substituted or unsubstituted C1-C. 60 alkyl, b1 is 3, and b2 is 2. The substituted C1-C 60 At least one substituent of the alkyl group is selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 alkoxy groups; and Each is substituted by at least one of the following C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 ) and -P(=O)(Q 11 (Q) 12 ), Q 11 To Q 13 Each is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy group, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heterocyclic group, a C1-C group substituted with at least one of deuterium, -F and cyano. 60 Alkyl group, C6-C substituted with at least one of deuterium, -F and cyano groups. 60 Aryl, biphenyl, and terphenyl.

2. The heterocyclic compound of claim 1, wherein the heterocyclic compound represented by formula 1 has a band gap of 0.3 eV or less between the singlet (S1) level and the triplet (T1) level.

3. A heterocyclic compound, wherein the heterocyclic compound is compound 2: 。 4. An organic light-emitting device, comprising: First electrode; The second electrode facing the first electrode; as well as An organic layer between the first electrode and the second electrode The organic layer comprises an emission layer and at least one heterocyclic compound as described in any one of claims 1 to 3.

5. The organic light-emitting device as claimed in claim 4, wherein... The first electrode is the anode. The second electrode is a cathode, and The organic layer further includes a hole transport region between the first electrode and the emitter layer, and an electron transport region between the emitter 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.

6. The organic light-emitting device of claim 4, wherein the emitting layer comprises the heterocyclic compound.

7. The organic light-emitting device of claim 6, wherein the heterocyclic compound included in the emitting layer is a thermally activated delayed fluorescence (TADF) emitter, and The emission layer emits delayed fluorescence.

8. The organic light-emitting device as described in claim 6, The emission layer is composed of the heterocyclic compound; or The emission layer further includes a body, and based on 100 parts by weight of the emission layer, the amount of the heterocyclic compound is in the range of 0.1 parts by weight to 50 parts by weight.

9. The organic light-emitting device of claim 5, wherein the hole transport region comprises a p-dopant, wherein the lowest unoccupied molecular orbital (LUMO) level of the p-dopant is -3.5 eV or less.

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