Heterocyclic compound, organic light-emitting device including same, electronic device, and electronic equipment

Abstract

The present application provides a heterocyclic compound represented by Formula 1, an organic light-emitting device including the same, and an electronic device and an electronic device including the organic light-emitting device. The description of each variable of Formula 1 is as described in the specification. Formula 1 # imgabs0 #

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0149357 filed in the Korean Intellectual Property Office on November 1, 2023, the entire contents of which are incorporated herein by reference in their entirety. Technical Field

[0003] One or more embodiments of the present disclosure relate to a heterocyclic compound, an organic light-emitting device, an electronic device, and an electronic equipment including the same. Background Art

[0004] Among light-emitting devices, self-emissive devices have wide viewing angles, high contrast, short response times, and excellent characteristics in terms of brightness, driving voltage, and response speed.

[0005] In an example, the light-emitting device may have a structure in which a first electrode is on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially on the first electrode. Holes provided from the first electrode move toward the emission layer through the hole transport region, and electrons provided from the second electrode move toward the emission layer through the electron transport region. Carriers (such as holes and electrons) recombine in the emission layer to generate excitons. Excitons transition from an excited state to a ground state, thereby generating light. Summary of the invention

[0006] One or more embodiments of the present disclosure include a heterocyclic compound, an organic light-emitting device, an electronic device, and an electronic equipment including the same.

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

[0008] According to one or more embodiments, a heterocyclic compound represented by Formula 1 is provided.

[0009] Formula 1

[0010]

[0011] In formula 1,

[0012] a1 and a2 can each independently be 0, 1 or 2,

[0013] The sum of a1 and a2 can be 1 or greater,

[0014] X 3 and X 4 can be independently O or S,

[0015] Y 31 , Y32 , Y 41 and Y 42 can be independently deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10a A substituted monovalent non-aromatic fused polycyclic group, unsubstituted or replaced by at least one R 10aSubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) or -P(=S)(Q 1 )(Q 2 ),

[0016] Ar 1 To Ar 5 Can be independently C 5 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,

[0017] L 6 Can be N(R 61 )、P(R 61 )、O、S、C(R 62 )(R 63 ) or Si(R 62 )(R 63 ),

[0018] L 7 Can be N(R 71 )、P(R 71 )、O、S、C(R 72 )(R 73 ) or Si(R 72 )(R 73 ),

[0019] L 8 Can be N(R 81 )、P(R 81 )、O、S、C(R 82 )(R 83 ) or Si(R 82 )(R 83 ),

[0020] L 9 Can be N(R 91 )、P(R 91 )、O、S、C(R92 )(R 93 ) or Si(R 92 )(R 93 ),

[0021] Z 31 To Z 33 , Z 41 To Z 43 , R 1 To R 5 , R 61 To R 63 , R 71 To R 73 , R 81 To R 83 and R 91 To R 93 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60Arylthio, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10a A substituted monovalent non-aromatic fused polycyclic group, unsubstituted or replaced by at least one R 10a Substituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) or -P(=S)(Q 1 )(Q 2 ),

[0022] Y 31 , Y 32 , Y 41 , Y 42 , Z 31 To Z 33 , Z 41 To Z 43 , R 1 To R 5 , R 61 To R 63 , R 71 To R 73 , R 81 To R 83 and R 91 To R 93 Two or more adjacent groups (eg, two or more adjacent groups) in the formula (R) may be optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C 5 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10aSubstituted C 1 -C 60 Heterocyclic group,

[0023] n1 to n5 may each independently be an integer selected from 0 to 10,

[0024] R 10a Can be:

[0025] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro,

[0026] Each unsubstituted or substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof,

[0027] Each unsubstituted or substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60Aryloxy C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof, or

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

[0029] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy or each unsubstituted or deuterated, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl.

[0030] According to one or more embodiments, an organic light-emitting device includes a first electrode, a second electrode facing the first electrode, and an interlayer between the first electrode and the second electrode and including an emission layer, wherein the organic light-emitting device further includes at least one of the above heterocyclic compounds.

[0031] According to one or more embodiments, an electronic device includes an organic light emitting device.

[0032] According to one or more embodiments, an electronic device includes an organic light emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0033] The above and other aspects and features of certain embodiments of the present disclosure will become more apparent through the following description in conjunction with the following:

[0034] Figure 1 is a schematic cross-sectional view of a structure of an organic light-emitting device according to an embodiment;

[0035] Figure 2 is a schematic cross-sectional view of a structure of an electronic device according to an embodiment;

[0036] Figure 3is a schematic diagram of a structure of an electronic device according to another embodiment;

[0037] Figure 4 is a schematic perspective view of an electronic device including an organic light-emitting device according to an embodiment;

[0038] Figure 5 is a schematic diagram of the exterior of a vehicle as an electronic device including an organic light-emitting device according to an embodiment; and

[0039] FIG. 6A to FIG. 6C Each is a schematic diagram of the interior of a vehicle according to various embodiments. DETAILED DESCRIPTION

[0040] The embodiments illustrated in the accompanying drawings will now be described in more detail with reference to their examples, wherein the same reference numerals refer to the same elements throughout the specification. In this regard, the present embodiments may have different forms and should not be construed as being limited to the description set forth herein. Accordingly, the embodiments are described below simply by reference to the figures to explain the various aspects of the embodiments described herein. As used herein, the term "and / or" includes any and all combinations of one or more related enumerated items. Throughout this disclosure, the expression "at least one of a, b, and c" indicates only a, only b, only c, both a and b, both a and c, both b and c, all a, b, and c, or variations thereof.

[0041] According to one or more embodiments, a heterocyclic compound is provided.

[0042] The heterocyclic compound is represented by Formula 1:

[0043] Formula 1

[0044]

[0045] Among them, in formula 1,

[0046] a1 and a2 can each independently be 0, 1 or 2, and

[0047] The sum of a1 and a2 may be 1 or greater.

[0048] In an embodiment, a1 and a2 may each be 1.

[0049] In formula 1,

[0050] X 3 and X 4 can be O or S independently.

[0051] In an embodiment, X 3 and X 4 Can each be O.

[0052] In formula 1,

[0053] Y 31 , Y 32 , Y 41 and Y 42 can be independently deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10aA substituted monovalent non-aromatic fused polycyclic group, unsubstituted or replaced by at least one R 10a Substituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) or -P(=S)(Q 1 )(Q 2 ).

[0054] In an embodiment, Y 31 , Y 32 , Y 41 and Y 42 Each may not be hydrogen.

[0055] In formula 1,

[0056] Ar 1 To Ar 5 Can be independently C 5 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.

[0057] In an embodiment, Ar 1 To Ar 5 Each of the above groups may independently be phenyl, naphthyl, phenanthryl, fluoranthene, triphenylene, pyrene, 1,2-triphenylene, indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, indolyl, pyridyl, pyrimidinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, furanyl, benzofuranyl, dibenzofuranyl, naphthofuranyl, benzonaphthofuranyl, dinaphthofuranyl, thienyl, benzothienyl, dibenzothienyl, naphthiothienyl, benzonaphthothienyl or dinaphthothienyl.

[0058] In formula 1,

[0059] L 6 Can be N(R 61 )、P(R 61 )、O、S、C(R 62 )(R63 ) or Si(R 62 )(R 63 ),

[0060] L 7 Can be N(R 71 )、P(R 71 )、O、S、C(R 72 )(R 73 ) or Si(R 72 )(R 73 ),

[0061] L 8 Can be N(R 81 )、P(R 81 )、O、S、C(R 82 )(R 83 ) or Si(R 82 )(R 83 ),and

[0062] L 9 Can be N(R 91 )、P(R 91 )、O、S、C(R 92 )(R 93 ) or Si(R 92 )(R 93 ).

[0063] In an embodiment, L 6 Can be N(R 61 ), L 7 Can be N(R 71 ), L 8 Can be N(R 81 ), and L 9 Can be N(R 91 ).

[0064] In formula 1,

[0065] Z 31 To Z 33 , Z 41 To Z 43 , R 1 To R 5 , R 61 To R 63 , R 71 To R 73 , R 81 To R 83 and R 91 To R 93 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, unsubstituted or substituted by at least one R10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10a A substituted monovalent non-aromatic fused polycyclic group, unsubstituted or replaced by at least one R 10a Substituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) or -P(=S)(Q 1 )(Q 2 ),

[0066] Y 31 , Y 32 , Y 41 , Y 42 , Z 31 To Z 33 , Z 41 To Z 43 , R 1 To R 5 , R 61 To R 63 , R 71 To R 73 , R 81 To R 83 and R 91 To R 93 Two or more adjacent groups (eg, two or more adjacent groups) in the formula (R) may be optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C 5 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0067] n1 to n5 may be an integer selected from 0 to 10, each independently.

[0068] In an embodiment, Y 31 , Y 32 , Y 41 and Y 42 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 alkyl.

[0069] In an embodiment, Y 31 , Y 32 , Y 41 and Y 42Each independently may be unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, cyano, nitro or any combination thereof.

[0070] In an embodiment, R 61 To R 63 , R 71 To R 73 , R 81 To R 83 and R 91 To R 93 may be each independently unsubstituted or substituted with at least one R 10a Substituted phenyl.

[0071] In an embodiment, R 61 To R 63 , R 71 To R 73 , R 81 To R 83 and R 91 To R 93 can be independently at least one R 10a Substituted phenyl.

[0072] In an embodiment, R 61 To R 63 , R 71 To R 73 , R 81 To R 83 and R 91 To R 93 Each may be independently a group represented by one selected from Formula 2-1 to Formula 2-17:

[0073]

[0074] Among them, in Formula 2-1 to Formula 2-17,

[0075] Z 11 To Z 15 Each independently as reference R 10a described, and

[0076] *Indicates the binding site with the neighboring atoms.

[0077] In equations 2-1 to 2-17, Z 11 To Z 15 can be independently: deuterium, -F, -Cl, -Br, -I, cyano or nitro;

[0078] Each unsubstituted or substituted C 1 -C 10 Alkyl, C 2 -C 10Alkenyl or C 2 -C 10 Alkynyl: deuterium, -F, -Cl, -Br, -I, cyano, nitro or any combination thereof;

[0079] Each unsubstituted or substituted C 6 -C 30 Aryl or C 1 -C 30 Heteroaryl: deuterium, -F, -Cl, -Br, -I, cyano, nitro, C 1 -C 10 Alkyl, C 2 -C 10 Alkenyl, C 2 -C 10 Alkynyl or any combination thereof; or

[0080] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 );and

[0081] Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 10 Alkyl; C 2 -C 10 Alkenyl; C 2 -C 10 Alkynyl; C 1 -C 10 alkoxy; or each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl or any combination thereof substituted C 3 -C 30 Carbocyclic or C 1 -C 30 Heterocyclic group.

[0082] In an embodiment, Z 31 To Z 33 , Z 41To Z 43 and R 1 To R 5 Can be independently:

[0083] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 2 -C 20 Alkenyl, C 2 -C 20 Alkynyl, C 1 -C 20 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 30 Aryl, C 6 -C 30 Aryloxy, C 6 -C 30 Arylthio, C 1 -C 30 Heteroaryl, C 1 -C 30 Heteroaryloxy, C 1 -C 30 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) or -P(=S)(Q 1 )(Q 2 );or

[0084] Each of the following C 1 -C 20 Alkyl, C 2-C 20 Alkenyl, C 2 -C 20 Alkynyl, C 1 -C 20 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 30 Aryl, C 6 -C 30 Aryloxy, C 6 -C 30 Arylthio, C 1 -C 30 Heteroaryl, C 1 -C 30 Heteroaryloxy, C 1 -C 30 Heteroarylthio group, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 10 Alkyl, C 2 -C 10 Alkenyl, C 2 -C 10 Alkynyl, C 1 -C 10 Alkoxy, C 3 -C 10 Carbocyclic group, C 1 -C 10 Heterocyclic group, C 6 -C 10 Aryloxy, C 6 -C 10 arylthio or any combination thereof.

[0085] In an embodiment, Z 31 To Z 33 and Z 41 To Z 43 Can be independently:

[0086] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 10 Alkyl, C 2 -C 10 Alkenyl, C 2 -C 10 Alkynyl, C1 -C 10 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 30 Aryl, C 1 -C 30 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) or -P(=S)(Q 1 )(Q 2 ).

[0087] In an embodiment, R 1 and R 2 Can be independently:

[0088] Hydrogen, deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, C 2 -C 20 Alkenyl, C 2 -C 20 Alkynyl, C 6 -C 30 Aryl or C 1 -C 30 heteroaryl; or

[0089] Each of the following C 1 -C 20 Alkyl, C 2 -C 20 Alkenyl, C 2 -C 20 Alkynyl, C 6 -C30 Aryl or C 1 -C 30 Heteroaryl: deuterium, -F, -Cl, -Br, -I, C 1 -C 10 Alkyl, C 2 -C 10 Alkenyl, C 2 -C 10 or any combination thereof.

[0090] In an embodiment, R 1 and R 2 Two or more adjacent groups (eg, two or more adjacent groups) in the formula (R) may be optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C 5 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.

[0091] In an embodiment, R 3 , R 4 and R 5 can each independently be hydrogen, deuterium, -F, -Cl, -Br or -I.

[0092] In formula 1,

[0093] R 10a Can be:

[0094] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0095] Each unsubstituted or substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryloxy, C 1 -C 60Heteroarylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof;

[0096] Each unsubstituted or substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or

[0097] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ),and

[0098] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 alkoxy; or each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl.

[0099] In an embodiment, the heterocyclic compound represented by Formula 1 may be a compound represented by one selected from Formula 1-1 to Formula 1-3:

[0100] Formula 1-1

[0101]

[0102] Formula 1-2

[0103]

[0104] Formula 1-3

[0105]

[0106] Among them, in Formula 1-1 to Formula 1-3,

[0107] R 31 To R 33 Each independently as reference R 3 Described,

[0108] R 41 To R 43 Each independently as reference R 4 described, and

[0109] a1 and a2 are each independently 0 or 1, and Ar 1 ,Ar 2 ,Ar 5 , R 1 , R 2 , R 5 、n1、n2、n5、X 3 , X 4 , L 6 To L 9 , Y 31 , Y 32 , Y 41 , Y 42 , Z 31 To Z 33 and Z 41 To Z 43 Each is as described herein.

[0110] In an embodiment, the heterocyclic compound represented by Formula 1 may be a compound represented by Formula 1-2.

[0111] In an embodiment, the heterocyclic compound represented by Formula 1 may be a compound represented by one selected from Formula 1-1A to Formula 1-3A:

[0112] Formula 1-1A

[0113]

[0114] Formula 1-2A

[0115]

[0116] Formula 1-3A

[0117]

[0118] Wherein, in Formula 1-1A to Formula 1-3A,

[0119] R 11 To R 14 Each independently as reference R 1 Described, R 21 To R 24 Each independently as reference R 2 Described, R 31 To R 33 Each independently as reference R 3 Described, R 41 To R 43 Each independently as reference R 4 Described,

[0120] R 51 and R 52 Each independently as reference R 5 described, and

[0121] a1 and a2 are each independently 0 or 1, and X 3 , X 4 , L 6 To L 9 , Y 31 , Y 32 , Y 41 , Y 42 , Z 31 To Z 33 and Z 41 To Z 43 Each is as described herein.

[0122] In an embodiment, the heterocyclic compound represented by Formula 1 may be a compound represented by Formula 1-2A.

[0123] In an embodiment, the heterocyclic compound represented by Formula 1 may be a compound represented by one selected from Formula 1-21 to Formula 1-23:

[0124] Formula 1-21

[0125]

[0126] Formula 1-22

[0127]

[0128] Formula 1-23

[0129]

[0130] Among them, in Formula 1-21 to Formula 1-23,

[0131] R 31 To R 33 Each independently as reference R 3 Described,

[0132] R 41 To R 43 Each independently as reference R 4 described, and

[0133] Ar 1 ,Ar 2 ,Ar 5 , R 1 , R 2 , R 5 、n1、n2、n5、X 3 , X 4 , L 6 To L 9 , Y 31 , Y 32 , Y 41 , Y 42 , Z 31 To Z 33 and Z 41 To Z 43 Each is as described herein.

[0134] In an embodiment, the heterocyclic compound represented by Formula 1 may be a compound represented by Formula 1-23.

[0135] In an embodiment, the heterocyclic compound represented by Formula 1 may be one selected from Compounds 1 to 12, Compounds 14 to 16, and Compounds 18 to 27:

[0136]

[0137]

[0138] In an embodiment, the heterocyclic compound represented by Formula 1 may emit blue light. For example, the heterocyclic compound represented by Formula 1 may emit blue light having a maximum emission wavelength of about 390 nm to about 500 nm, about 410 nm to about 500 nm, about 410 nm to about 490 nm, about 430 nm to about 480 nm, about 440 nm to about 475 nm, or about 455 nm to about 470 nm. For example, the heterocyclic compound represented by Formula 1 may emit blue light having a maximum emission wavelength of about 430 nm to about 480 nm. However, the embodiment is not limited thereto. Therefore, the heterocyclic compound represented by Formula 1 can be effectively used to manufacture an organic light-emitting device that emits blue light.

[0139] The heterocyclic compound represented by Formula 1 can emit blue light with high color purity by introducing a phenoxy group or a phenylthio group. st , which has the effect of improving efficiency.

[0140] Therefore, an organic light-emitting device including the heterocyclic compound represented by Formula 1 may have characteristics of high efficiency and low driving voltage. For example, by including the heterocyclic compound represented by Formula 1 as a dopant in an emission layer, high efficiency and low driving voltage may be achieved.

[0141] The synthesis method of the heterocyclic compound represented by Formula 1 can be recognized by one of ordinary skill in the art by referring to the examples provided below.

[0142] According to one or more embodiments, an organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an interlayer between the first electrode and the second electrode and including an emission layer, wherein the organic light-emitting device further includes at least one heterocyclic compound represented by Formula 1 described herein.

[0143] In an embodiment, the interlayer may include a heterocyclic compound represented by Formula 1.

[0144] In an embodiment, the emission layer may include the heterocyclic compound represented by Formula 1.

[0145] In an embodiment, the first electrode may be an anode, the second electrode may be a cathode, and the interlayer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode. In this regard, the hole transport region may include at least one selected from a hole injection layer, a hole transport layer, a buffer layer, an emission auxiliary layer, and an electron blocking layer, and the electron transport region may include at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.

[0146] In an embodiment, the emission layer may emit blue light. The emission layer may emit blue light having a maximum emission wavelength of about 390 nm to about 500 nm, about 410 nm to about 500 nm, about 410 nm to about 490 nm, about 430 nm to about 480 nm, about 440 nm to about 475 nm, or about 455 nm to about 470 nm. In some embodiments, the emission layer may emit blue light having a maximum emission wavelength of about 390 nm to about 500 nm, for example, about 410 nm to about 490 nm.

[0147] In an embodiment, the emission layer may include a host and a dopant, and the dopant may include a heterocyclic compound represented by Formula 1.

[0148] In an embodiment, in the emission layer, the amount of the host may be greater than the amount of the dopant based on the total weight.

[0149] In an embodiment, the host may be an anthracene compound.

[0150] According to one or more embodiments, an electronic device includes an organic light emitting device.

[0151] In an embodiment, the electronic device may further include a thin film transistor. In some embodiments, the thin film transistor may include a source electrode and a drain electrode, and the first electrode of the organic light emitting device may be electrically connected to at least one selected from the source electrode and the drain electrode of the thin film transistor.

[0152] According to one or more embodiments, an electronic device includes an organic light emitting device.

[0153] The electronic device may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an interior light, an exterior light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a retractable display, a laser printer, a phone, a mobile phone, a tablet computer, a tablet phone, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a 3D display, a virtual reality display, an augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater screen, a stadium screen, a light therapy device, a sign, a car sensor, a home sensor and / or a solar cell.

[0154] Figure 1 Description

[0155] Figure 1 2 is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment. The organic light-emitting device 10 includes a first electrode 110 , an interlayer 130 , and a second electrode 150 .

[0156] In the following, reference Figure 1 A structure of an organic light-emitting device 10 and a method of manufacturing the organic light-emitting device 10 according to an embodiment are described.

[0157] First electrode 110

[0158] exist Figure 1 In the embodiment, the substrate may be additionally under the first electrode 110 and / or on the second electrode 150. As the substrate, a glass substrate and / or a plastic substrate may be used. In an embodiment, the substrate may be a flexible substrate and may include a plastic having excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.

[0159] The first electrode 110 may be formed by, for example, depositing and / 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 110 may be a high work function material that facilitates injection of holes.

[0160] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), or any combination thereof. In an embodiment, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0161] The first electrode 110 may have a single-layer structure consisting of a single layer or a multi-layer structure including a plurality of layers. In an implementation, the first electrode 110 may have a triple-layer structure of ITO / Ag / ITO.

[0162] Mezzanine 130

[0163] The interlayer 130 is on the first electrode 110. The interlayer 130 may include an emission layer.

[0164] The interlayer 130 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 150 .

[0165] In addition to various suitable organic materials, the interlayer 130 may further include metal-containing compounds and / or inorganic materials (such as quantum dots), etc.

[0166] In an embodiment, the interlayer 130 may include i) two or more emission units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer between the two or more emission units. When the interlayer 130 includes the two or more emission units and the charge generation layer, the organic light-emitting device 10 may be a tandem organic light-emitting device.

[0167] Hole transport region in interlayer 130

[0168] The hole transport region may have: i) a single-layer structure consisting of a single layer (composed of a single material), ii) a single-layer structure consisting of a single layer (composed of multiple materials different from each other), or iii) a multilayer structure including multiple layers (including multiple materials different from each other).

[0169] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof.

[0170] In an embodiment, the hole transport region may have a multi-layer structure, including 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 / emission auxiliary layer structure, wherein the constituent layers of each structure are stacked in sequence from the first electrode 110.

[0171] The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:

[0172] Formula 201

[0173]

[0174] Formula 202

[0175]

[0176] Among them, in equation 201 and equation 202,

[0177] L 201 To L 204 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0178] L 205 Can be *-O-*', *-S-*', *-N(Q 201)-*', unsubstituted or replaced by at least one R 10a Substituted C 1 -C 20 Alkylene, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 20 Alkenylene, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0179] xa1 to xa4 may each independently be an integer selected from 0 to 5,

[0180] xa5 may be an integer selected from 1 to 10,

[0181] R 201 To R 204 and Q 201 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0182] R 201 and R 202 may be optionally substituted by a single bond (eg, a single covalent bond), unsubstituted or substituted by at least one R 10a Substituted C 1 -C 5 Alkylene is either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 5 Alkenylene groups are connected to each other to form an unsubstituted or substituted R 10a Substituted C 8 -C 60 Polycyclic groups (e.g., carbazole groups) (e.g., compound HT16),

[0183] R 203 and R 204 may be optionally substituted by a single bond (eg, a single covalent bond), unsubstituted or substituted by at least one R 10a Substituted C 1 -C 5 Alkylene is either unsubstituted or substituted with at least one R 10a Substituted C 2 -C5 Alkenylene groups are connected to each other to form an unsubstituted or substituted R 10a Substituted C 8 -C 60 polycyclic groups, and

[0184] na1 may be an integer selected from 1 to 4.

[0185] In an embodiment, each of Formula 201 and Formula 202 may include at least one selected from the groups represented by Formula CY201 to Formula CY217:

[0186]

[0187] Among them, in formula CY201 to formula CY217, R 10b and R 10c Each can be referred to as R 10a Described, Cyclic 201 To Ring CY 204 Can be independently C 3 -C 20 Carbocyclic or C 1 -C 20 heterocyclic group, and at least one hydrogen in Formula CY201 to Formula CY217 may be unsubstituted or replaced by R as described herein 10a replaced.

[0188] In an embodiment, ring CY in formula CY201 to formula CY217 201 To Ring CY 204 Each independently may be phenyl, naphthyl, phenanthryl or anthracenyl.

[0189] In an embodiment, each of Formula 201 and Formula 202 may include at least one selected from the groups represented by Formula CY201 to Formula CY203.

[0190] In an embodiment, Formula 201 may include at least one selected from the group represented by Formula CY201 to Formula CY203 and at least one selected from the group represented by Formula CY204 to Formula CY217.

[0191] In an embodiment, in Formula 201, xa1 may be 1, R 201 may be a group represented by one selected from Formula CY201 to Formula CY203, xa2 may be 0, and R 202 It may be a group represented by one selected from Formula CY204 to Formula CY207.

[0192] In an embodiment, each of Formula 201 and Formula 202 may not include the group represented by Formula CY201 to Formula CY203.

[0193] In an embodiment, each of Formula 201 and Formula 202 may not include the group represented by Formula CY201 to Formula CY203 and may include at least one selected from the groups represented by Formula CY204 to Formula CY217.

[0194] In an embodiment, each of Formula 201 and Formula 202 may not include the group represented by Formula CY201 to Formula CY217.

[0195] In an embodiment, the hole transport region may include one selected from the group consisting of compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), or any combination thereof:

[0196]

[0197]

[0198]

[0199]

[0200]

[0201] The thickness of the hole transport region may be about to about For example, about to about When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be about to about For example, about to about And the thickness of the hole transport layer may be about to about For example, about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within the above ranges, appropriate or satisfactory hole transport characteristics may be obtained without significantly increasing the driving voltage.

[0202] The emission auxiliary layer can increase the luminous efficiency by compensating the optical resonance distance according to the wavelength of light emitted by the emission layer, and the electron blocking layer can block or reduce the leakage of electrons from the emission layer to the hole transport region. Materials that can be included in the hole transport region can be included in the emission auxiliary layer and the electron blocking layer.

[0203] p-dopant

[0204] In addition to these materials, the hole transport region may further include a charge generation material for improvement of conductive properties (eg, electrical conductivity properties). The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region (eg, in the form of a single layer consisting of the charge generation material).

[0205] The charge generating material may be, for example, a p-dopant.

[0206] For example, the LUMO level of the p-dopant may be less than or equal to -3.5 eV.

[0207] In an embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including the element EL1 and the element EL2, or any combination thereof.

[0208] Examples of the quinone derivative may include TCNQ and F4-TCNQ.

[0209] Examples of the cyano group-containing compound may include HAT-CN and a compound represented by Formula 221.

[0210]

[0211] Formula 221

[0212]

[0213] In formula 221,

[0214] R 221 To R 223 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 a heterocyclic group, and

[0215] Selected from R 221 To R 223 At least one of them may be independently C each substituted by 3 -C 60 Carbocyclic or C 1 -C 60Heterocyclic group: cyano; -F; -Cl; -Br; -I; C substituted by cyano, -F, -Cl, -Br, -I or any combination thereof 1 -C 20 or any combination thereof.

[0216] In a compound including an element EL1 and an element EL2, the element EL1 may be a metal, a metalloid, or a combination thereof, and the element EL2 may be a nonmetal, a metalloid, or a combination thereof.

[0217] Examples of metals may include alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt ( (e.g., tantalum, cerium, praseodymium, neodymium, promethium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, lutetium, etc.).

[0218] Examples of metalloids may include silicon (Si), antimony (Sb), and tellurium (Te).

[0219] Examples of non-metals may include oxygen (O) and halogens (eg, F, Cl, Br, I, etc.).

[0220] Examples of compounds including element EL1 and element EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, metalloid iodides, etc.), metal tellurides, or any combination thereof.

[0221] Examples of metal oxides may include tungsten oxides (eg, WO, W 2 O 3 , WO 2 , WO 3 , W 2 O 5 etc.), vanadium oxides (e.g., VO, V 2 O 3 , VO2 、V 2 O 5 etc.), molybdenum oxides (e.g., MoO, Mo 2 O 3 、MoO 2 、MoO 3 、Mo 2 O 5 etc.) and rhenium oxides (e.g., ReO 3 wait).

[0222] Examples of the metal halide may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and lanthanide metal halides.

[0223] Examples of the alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.

[0224] Examples of alkaline earth metal halides may include BeF 2 MgF 2 , CaF 2 , SrF 2 , BaF 2 、BeCl 2 MgCl 2 , CaCl 2 、SrCl 2 、BaCl 2 ,BeBr 2 MgBr 2 , CaBr 2 , SrBr 2 ,BaBr 2 ,BeI 2 MgI 2 ,CaI 2 , SrI 2 and BaI 2 .

[0225] Examples of transition metal halides may include titanium halides (eg, TiF 4 、TiCl 4 、TiBr 4 、TiI 4 etc.), zirconium halides (e.g., ZrF 4 、ZrCl 4 , ZrBr 4 , ZrI 4 etc.), hafnium halides (e.g., HfF 4 , HfCl4 , HfBr 4 , HfI 4 etc.), vanadium halides (e.g., VF 3 、VCl 3 , VBr 3 VI 3 etc.), niobium halides (e.g., NbF 3 、NbCl 3 , NbBr 3 , NbI 3 etc.), tantalum halides (e.g., TaF 3 、TaCl 3 、TaBr 3 、TaI 3 etc.), chromium halides (e.g., CrF 3 CrCl 3 CrBr 3 CrI 3 etc.), molybdenum halides (e.g., MoF 3 、MoCl 3 、MoBr 3 、MoI 3 etc.), tungsten halides (e.g., WF 3 、WCl 3 , WBr 3 , WI 3 etc.), manganese halides (e.g., MnF 2 、MnCl 2 、MnBr 2 、MnI 2 etc.), technetium halides (e.g., TcF 2 , TcCl 2 、TcBr 2 , TcI 2 etc.), rhenium halides (e.g., ReF 2 、ReCl 2 、ReBr 2 、ReI 2 etc.), ferrous halides (e.g., FeF 2 、FeCl 2 , FeBr 2 ,FeI 2 etc.), ruthenium halides (e.g., RuF 2 、RuCl 2 ,RuBr 2 , RuI 2 etc.), osmium halides (e.g., OsF 2 , OsCl 2 、OsBr 2 , OsI 2etc.), cobalt halides (e.g., CoF 2 、CoCl 2 ,CoBr 2 、CoI 2 etc.), rhodium halides (e.g., RhF 2 , RhCl 2 , RhBr 2 , RhI 2 etc.), iridium halides (e.g., IrF 2 、IrCl 2 ,IrBr 2 ,IrI 2 etc.), nickel halides (e.g., NiF 2 、NiCl 2 、NiBr 2 , NiI 2 etc.), palladium halides (e.g., PdF 2 , PdCl 2 , PdBr 2 , PdI 2 etc.), platinum halides (e.g., PtF 2 、PtCl 2 , PtBr 2 , PtI 2 etc.), cuprous halides (e.g., CuF, CuCl, CuBr, CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.), and gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.).

[0226] Examples of late transition metal halides may include zinc halides (eg, ZnF 2 、ZnCl 2 、ZnBr 2 、ZnI 2 etc.), indium halides (e.g., InI 3 etc.) and tin halides (e.g., SnI 2 wait).

[0227] Examples of lanthanide metal halides may include YbF, YbF 2 , YbF 3 、SmF 3 、YbCl、YbCl 2 YbCl 3 、SmCl 3 , YbBr, YbBr 2 , YbBr 3 、SmBr 3 、YbI、YbI 2 ,YbI 3 and SmI3 .

[0228] Examples of metalloid halides may include antimony halides (eg, SbCl 5 wait).

[0229] Examples of metal tellurides may include alkali metal tellurides (eg, Li 2 Te、Na 2 Te, K 2 Te、Rb 2 Te, Cs 2 Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g., TiTe 2 、ZrTe 2 、HfTe 2 、V 2 Te 3 , Nb 2 Te 3 、 2 Te 3 Cr 2 Te 3 、Mo 2 Te 3 , W 2 Te 3 , MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu 2 Te, CuTe, Ag 2 Te, AgTe, Au 2 Te, etc.), late transition metal tellurides (e.g., ZnTe, etc.), and lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).

[0230] Emission layer in interlayer 130

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

[0232] The emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.

[0233] The amount of the dopant in the emission layer may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.

[0234] In an embodiment, the emissive layer may include quantum dots.

[0235] In an embodiment, the emission layer may include a delayed fluorescent material. The delayed fluorescent material may act as a host or a dopant in the emission layer.

[0236] The emission layer may further include a host, an auxiliary dopant, a sensitizer, a delayed fluorescent material, or any combination thereof in addition to the heterocyclic compound represented by Formula 1. Each of the host, the auxiliary dopant, the sensitizer, the delayed fluorescent material, or any combination thereof may include at least one deuterium.

[0237] For example, the emission layer may include a heterocyclic compound represented by Formula 1 and a host. The host may be different from the heterocyclic compound represented by Formula 1, and the host may include an electron transport compound (electron transport host), a hole transport compound (hole transport host), a bipolar compound (electron transport host), or any combination thereof. The host may not include a metal. The electron transport compound, the hole transport compound, and the bipolar compound are different from each other.

[0238] In an embodiment, the emission layer includes the heterocyclic compound represented by Formula 1 and a host, and the host may include an electron transport compound and a hole transport compound.

[0239] In embodiments, the electron transport compound and the hole transport compound may form an exciplex.

[0240] The thickness of the emission layer may be about to about For example, about to about When the thickness of the emission layer is within the above range, excellent light emitting characteristics can be obtained without significantly increasing the driving voltage.

[0241] main body

[0242] In an embodiment, the host may include a compound represented by Formula 301:

[0243] Formula 301

[0244] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ]xb21 ,

[0245] Wherein, in Formula 301,

[0246] Ar 301 and L 301 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0247] xb11 can be 1, 2 or 3,

[0248] xb1 may be an integer selected from 0 to 5,

[0249] R 301 It may be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O) 2 (Q 301 ) or -P(=O)(Q 301 )(Q 302 ),

[0250] xb21 may be an integer selected from 1 to 5, and

[0251] Q 301 To Q 303 As reference Q 1 Described.

[0252] In an embodiment, when xb11 in Formula 301 is 2 or greater, two or more Ar 301 Can be linked to each other via a single bond (eg, a single covalent bond).

[0253] In an embodiment, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:

[0254] Formula 301-1

[0255]

[0256] Formula 301-2

[0257]

[0258] Among them, in Formula 301-1 and Formula 301-2,

[0259] Ring A 301 To Ring A 304 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0260] X 301 Can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),

[0261] xb22 and xb23 can each independently be 0, 1 or 2,

[0262] L 301 , xb1 and R 301 Each as described in this specification,

[0263] L 302 To L 304 Each independently as reference L 301 Described,

[0264] xb2 to xb4 are each independently as described with reference to xb1, and

[0265] R 302 To R 305 and R 311 To R 314 Each as reference R 301 Described.

[0266] In embodiments, the host may include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. In embodiments, the host may include a Be complex (eg, compound H55), a Mg complex, a Zn complex, or any combination thereof.

[0267] In an embodiment, the host may include one selected from Compound H1 to Compound H124, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), 9,10-di(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-di(9-carbazolyl)benzene (mCP), 1,3,5-tri(carbazolyl-9-yl)benzene (TCP), or any combination thereof:

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275] In an embodiment, the host may include a first host compound and a second host compound.

[0276] In embodiments, the first host compound may be a hole transporting host.

[0277] In embodiments, the second host compound may be an electron transporting host.

[0278] In an embodiment, the term “hole transport host” may be a compound including a hole transport moiety.

[0279] In an embodiment, the term “electron transport host” may be a compound including an electron transport moiety and a compound having a bipolar property.

[0280] In this article, the terms "hole transport host" and "electron transport host" can be understood according to the relative difference between the hole mobility and the electron mobility in the hole transport host and the electron transport host, respectively. For example, even when the electron transport host does not include an electron transport part, a bipolar compound that exhibits a relatively higher electron mobility than the hole transport host can also be understood as an electron transport host.

[0281] In an embodiment, the hole transport host may be represented by one selected from Formula 311-1 to Formula 311-6, and the electron transport host may be represented by one selected from Formula 312-1 to Formula 312-4 and Formula 313.

[0282] Formula 311-1

[0283]

[0284] Formula 311-2

[0285]

[0286] Formula 311-3

[0287]

[0288] Formula 311-4

[0289]

[0290] Formula 311-5

[0291]

[0292] Formula 311-6

[0293]

[0294] Formula 312-1

[0295]

[0296] Formula 312-2

[0297]

[0298] Formula 312-3

[0299]

[0300] Formula 312-4

[0301]

[0302] Formula 313

[0303]

[0304] Formula 313A

[0305]

[0306] In Formulas 311-1 to 311-6, Formulas 312-1 to 312-4, Formula 313, and Formula 313A,

[0307] Ar 301 may be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0308] A 301 To A 304 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,

[0309] X 301 Can be O, S, N[(L 304 ) xb4 -R 304 ]、C[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ] or Si[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ],

[0310] X 302 , Y 301 and Y 302 can each independently be a single bond (eg, a single covalent bond), O, S, N[(L 305 ) xb5 -R 305 ]、C[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ]、Si[(L 304 )xb4 -R 304 ][(L 305 ) xb5 -R 305 ] or S(=O) 2 ,

[0311] xb1 to xb5 can be 0, 1, 2, 3, 4, or 5.

[0312] xb6 can be 1, 2, 3, 4 or 5,

[0313] X 321 To X 328 can be independently N or C[(L 324 ) xb24 -R 324 ],

[0314] Y 321 Can be *-O-*', *-S-*', *-N[(L 325 ) xb25 -R 325 ]-*'、*-C[(L 325 ) xb25 -R 325 ][(L 326 ) xb26 -R 326 ]-*'、*-C[(L 325 ) xb25 -R 325 ]=C[(L 326 ) xb26 -R 326 ]-*'、*-C[(L 325 ) xb25 -R 325 ]=N-*'or*-N=C[(L 326 ) xb26 -R 326 ]-*',

[0315] k21 can be 0, 1 or 2. When k21 is 0, Y 321 does not exist (e.g., does not appear),

[0316] xb21 to xb26 may each independently be 0, 1, 2, 3, 4 or 5,

[0317] A 31 , A 32 and A 34 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 30 Heterocyclic group,

[0318] A 33 may be a group represented by formula 313A,

[0319] X 31 Can be N[(L 335 ) xb35 -R 335 ]、O、S、Se、C[(L 335 ) xb35 -R 335 ][(L 336 ) xb36 -R 336 ] or Si[(L 335 ) xb35 -R 335 ][(L 336 ) xb36 -R 336 ],

[0320] xb31 to xb36 may each independently be 0, 1, 2, 3, 4 or 5,

[0321] xb42 to xb44 may each independently be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10,

[0322] L 301 To L 306 , L 321 To L 326 and L 331 To L 336 Each R may be independently a single bond (eg, a single covalent bond), unsubstituted or substituted with at least one R 10a Substituted C 1 -C 20 Alkylene, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 20 Alkenylene, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 20 Alkyne, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkylene, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkylene, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkenylene, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10Heterocycloalkenylene, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylene, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroarylene, unsubstituted or substituted with at least one R 10a The substituted divalent non-aromatic fused polycyclic group is either unsubstituted or substituted with at least one R 10a a substituted divalent non-aromatic fused heteropolycyclic group,

[0323] R 301 To R 305 , R 311 To R 314 , R 321 To R 326 and R 331 To R 336 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10a A substituted monovalent non-aromatic fused polycyclic group, unsubstituted or replaced by at least one R 10a Substituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) or -P(=S)(Q 1 )(Q 2 ),

[0324] R 321 To R 326 Two or more adjacent groups (eg, two or more adjacent groups) in the formula (R) may be optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0325] R 10a Can be:

[0326] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0327] Each unsubstituted or substituted C 1-C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof;

[0328] Each unsubstituted or substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or

[0329] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ),and

[0330] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 alkoxy; or each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl.

[0331] In an embodiment, the first host compound and the second host compound may form an exciplex.

[0332] Phosphorescent dopants

[0333] In an embodiment, the emission layer may further include a phosphorescent dopant.

[0334] In an embodiment, the emission layer may further include a phosphorescent dopant, and the phosphorescent dopant may serve as a sensitizer.

[0335] The phosphorescent dopant may include at least one transition metal as a central metal.

[0336] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.

[0337] The phosphorescent dopant may be electrically neutral.

[0338] In an embodiment, the phosphorescent dopant may be an organometallic compound.

[0339] In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 401:

[0340] Formula 401

[0341] M(L 401 ) xc1 (L 402 ) xc2

[0342] Formula 402

[0343]

[0344] Among them, in equation 401 and equation 402,

[0345] M may be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),

[0346] L 401 may be a ligand represented by Formula 402, and xc1 is 1, 2 or 3, wherein when xc1 is 2 or greater, two or more L 401 may be the same or different from each other,

[0347] L 402 may be an organic ligand, and xc2 may be 0, 1, 2, 3 or 4, wherein when xc2 is 2 or greater, two or more L 402 may be the same or different from each other,

[0348] X 401 and X 402 may each independently be nitrogen or carbon,

[0349] Ring A 401 and Ring A 402 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,

[0350] T 401 It may be a single bond (eg, a single covalent bond), *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*'、*-C(Q 411 )(Q 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*'or*=C=*',

[0351] X 403 and X 404 Each of them can be independently a chemical bond (for example, a covalent bond or a coordinate bond, which can also be called a coordinate covalent bond or a coordinate bond), O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) or Si(Q413 )(Q 414 ),

[0352] Q 411 To Q 414 Each as reference Q 1 Described,

[0353] R 401 and R 402 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 20 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 20 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) or -P(=O)(Q 401 )(Q 402 ),

[0354] Q 401 To Q 403 Each as reference Q 1 Described,

[0355] xc11 and xc12 may each independently be an integer selected from 0 to 10, and

[0356] * and *' in Formula 402 each indicate a binding site with M in Formula 401.

[0357] In an embodiment, in formula 402, i) X 401 may be nitrogen, and X 402 Can be carbon, or ii) X 401 and X 402 Each of may be nitrogen.

[0358] In an embodiment, when xc1 in Formula 401 is 2 or greater, two or more L 401 The two rings A 401 Optionally, T as a linker 402 Connected together and the two rings A 402 Optionally, T as a linker 403 Connected together (see Compound PD1 to Compound PD4 and Compound PD7). 402 and T 403 Each as reference T 401 Described.

[0359] L in Formula 401 402 Can be an organic ligand. In an embodiment, L 402 It may include a halogen group, a diketone group (e.g., acetylacetonate group), a carboxylic acid group (e.g., picolinate group), -C(=O), an isonitrile group, a -CN group, a phosphorus-containing group (e.g., phosphine group, phosphite group, etc.), or any combination thereof.

[0360] The phosphorescent dopant may include, for example, one selected from Compound PD1 to Compound PD41 or any combination thereof:

[0361]

[0362]

[0363]

[0364] Fluorescent dopants

[0365] In an embodiment, the emission layer may further include a fluorescent dopant.

[0366] The fluorescent dopant may include an amine-containing compound, a styrene-containing compound, or any combination thereof.

[0367] In an embodiment, the fluorescent dopant may include a compound represented by Formula 501:

[0368] Formula 501

[0369]

[0370] Wherein, in Formula 501,

[0371] Ar 501 , L 501 To L 503 , R 501 and R 502 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0372] xd1 to xd3 may each independently be 0, 1, 2 or 3, and

[0373] xd4 can be 1, 2, 3, 4, 5 or 6.

[0374] In an embodiment, Ar in Formula 501 501 It may be a condensed ring group in which three or more monocyclic groups are condensed together (for example, anthracenyl, 1,2-triphenylenyl, pyrenyl, etc.).

[0375] In an embodiment, xd4 in equation 501 may be 2.

[0376] In an embodiment, the fluorescent dopant may include: one selected from Compound FD1 to Compound FD36; DPVBi; DPAVBi; or any combination thereof:

[0377]

[0378]

[0379]

[0380] Delayed fluorescence material

[0381] In an embodiment, the emission layer may further include a delayed fluorescent material.

[0382] Herein, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.

[0383] The delayed fluorescent material included in the emission layer may act as a host or a dopant depending on the types (or kinds) of other materials included in the emission layer.

[0384] In an embodiment, the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material may be at least about 0 eV and not more than about 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material satisfies the range as described above, up-conversion of the delayed fluorescent material from the triplet state to the singlet state may effectively occur, and thus, the luminous efficiency of the organic light-emitting device 10 may be increased.

[0385] In an embodiment, the delayed fluorescent material may include: i) at least one electron donor (eg, a π-electron-rich C 3 -C60 Cyclic groups, such as carbazolyl) and at least one electron acceptor (e.g., sulfoxide, cyano, and π-electron-deficient nitrogen-containing C 1 -C 60 cyclic groups, etc.), ii) comprising C containing at least two cyclic groups fused together and sharing boron (B) 8 -C 60 Polycyclic materials.

[0386] Examples of the delayed fluorescent material may include at least one selected from Compound DF1 to Compound DF9:

[0387]

[0388] quantum dots

[0389] The emissive layer may include quantum dots.

[0390] Herein, "quantum dot" refers to a crystal of a semiconductor compound, and may include any appropriate material capable of emitting light of various appropriate emission wavelengths depending on the size of the crystal.

[0391] The diameter of a quantum dot can be, for example, from about 1 nm to about 10 nm.

[0392] The quantum dots may be synthesized by a wet chemical process, a metal organic chemical vapor deposition (MOCVD) process, a molecular beam epitaxy (MBE) process, and / or any suitable process similar thereto.

[0393] The wet chemical process is a method that includes mixing the precursor material with an organic solvent and then growing the quantum dot particle crystal. When the quantum dot particle crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot particle crystal and controls the growth of the quantum dot particle crystal, so that the growth of the quantum dot particle crystal can be controlled by a process that is lower in cost and easier than vapor deposition methods (such as metal organic chemical vapor deposition or molecular beam epitaxy).

[0394] Quantum dots may include: Group II-VI semiconductor compounds; Group III-V semiconductor compounds; Group III-VI semiconductor compounds; Group I-III-VI semiconductor compounds; Group IV-VI semiconductor compounds; Group IV elements or compounds; or any combination thereof.

[0395] Examples of II-VI semiconductor compounds may include binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, and / or MgS; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, Cd ZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe and / or MgZnS; quaternary compounds, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and / or HgZnSTe; or any combination thereof.

[0396] Examples of III-V semiconductor compounds may include binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, and / or InSb; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, and / or InPSb; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and / or InAlPSb; or any combination thereof. In an embodiment, the III-V semiconductor compound may further include a Group II element. Examples of the Group III-V semiconductor compound further including the Group II element may include InZnP, InGaZnP, and / or InAlZnP.

[0397] Examples of III-VI semiconductor compounds may include binary compounds such as GaS, GaSe, Ga 2 Se 3 、GaTe、InS、InSe、In 2 S 3 、In 2 Se 3 and / or InTe; ternary compounds such as InGaS 3 and / or InGaSe 3 ; or any combination thereof.

[0398] Examples of Group I-III-VI semiconductor compounds may include: ternary compounds such as AgInS, AgInS 2 、CuInS、CuInS 2 、CuGaO 2 、AgGaO 2 and / or AgAlO 2 ; or any combination thereof.

[0399] Examples of Group IV-VI semiconductor compounds may include: binary compounds, such as SnS, SnSe, SnTe, PbS, PbSe and / or PbTe; ternary compounds, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe and / or SnPbTe; quaternary compounds, such as SnPbSSe, SnPbSeTe and / or SnPbSTe; or any combination thereof.

[0400] Examples of Group IV elements or compounds may include: single elements, such as Si and / or Ge; binary compounds, such as SiC and / or SiGe; or any combination thereof.

[0401] Each element included in the multi-element compound such as the binary compound, the ternary compound, and the quaternary compound may be present in the particle at a uniform concentration or a non-uniform concentration.

[0402] In an embodiment, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is uniform (or substantially uniform), or may have a core-shell dual structure. In an embodiment, the material included in the core and the material included in the shell may be different from each other.

[0403] The shell of the quantum dot can act as a protective layer to prevent or reduce the chemical denaturation of the core to maintain the semiconductor properties and / or act as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient, wherein the concentration of the element present in the shell decreases along the direction toward the center of the core.

[0404] Examples of quantum dot shells are oxides of metals, metalloids and / or non-metals, semiconductor compounds, or combinations thereof. Examples of oxides of metals, metalloids and / or non-metals may include: binary compounds, such as SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3 , Mn 3 O 4, CuO, FeO, Fe 2 O 3 , Fe 3 O 4 , CoO, Co 3 O 4 and / or NiO; ternary compounds such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 and / or CoMn 2 O 4 ; or any combination thereof. As described herein, examples of semiconductor compounds may include: Group II-VI semiconductor compounds; Group III-V semiconductor compounds; Group III-VI semiconductor compounds; Group I-III-VI semiconductor compounds; Group IV-VI semiconductor compounds; or any combination thereof. In an embodiment, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.

[0405] The quantum dots may have a FWHM of an emission wavelength spectrum of less than or equal to about 45 nm, less than or equal to about 40 nm, or, for example, less than or equal to about 30 nm. When the FWHM of the quantum dots is within these ranges, the quantum dots may have improved color purity and / or improved color reproducibility. In some embodiments, because the light emitted by the quantum dots is emitted in all (or substantially all) directions, the wide viewing angle may be improved.

[0406] In some embodiments, quantum dots can be in the form of spherical, pyramidal, multi-armed, and / or cubic nanoparticles, nanotubes, nanowires, nanofibers, and / or nanoplates.

[0407] Because the energy band gap can be adjusted by controlling the size of the quantum dots, light having various appropriate wavelength bands can be obtained from the quantum dot emission layer. Accordingly, by using quantum dots of different sizes, an organic light-emitting device that emits light of various appropriate wavelengths can be realized. In more detail, the size of the quantum dots can be selected to emit red light, green light, and / or blue light. In some embodiments, the size of the quantum dots can be configured to emit white light through a combination of various appropriate colors of light.

[0408] Electron transport region in interlayer 130

[0409] The electron transport region may have: i) a single-layer structure consisting of a single layer (composed of a single material), ii) a single-layer structure consisting of a single layer (comprising a plurality of different materials), or iii) a multi-layer structure including a plurality of layers (comprising a plurality of different materials).

[0410] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0411] In an embodiment, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the constituent layers of each structure are stacked in a prescribed order from the emission layer.

[0412] In an embodiment, the electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, and / or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π-electron-deficient nitrogen-containing C 1 -C 60 Cyclic group.

[0413] In an embodiment, the electron transport region may include a compound represented by Formula 601.

[0414] Formula 601

[0415] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21

[0416] In formula 601,

[0417] Ar 601 and L 601 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0418] xe11 can be 1, 2 or 3,

[0419] xe1 can be 0, 1, 2, 3, 4 or 5,

[0420] R 601 may be unsubstituted or substituted with at least one R 10a Substituted C3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O) 2 (Q 601 ) or -P(=O)(Q 601 )(Q 602 ),

[0421] Q 601 To Q 603 Each as reference Q 1 Described,

[0422] xe21 can be 1, 2, 3, 4, or 5, and

[0423] Ar 601 , L 601 and R 601 At least one of them may be independently unsubstituted or substituted by at least one R 10a Substituted π-electron-deficient nitrogen-containing C 1 -C 60 Cyclic group.

[0424] In an embodiment, when xe11 in Formula 601 is 2 or greater, two or more Ar 601 Can be linked together via a single bond (eg, a single covalent bond).

[0425] In an embodiment, Ar in Formula 601 601 may be unsubstituted or substituted with at least one R 10a Substituted anthracenyl.

[0426] In an embodiment, the electron transport region may include a compound represented by Formula 601-1:

[0427] Formula 601-1

[0428]

[0429] Among them, in formula 601-1,

[0430] X 614 Can be N or C(R 614 ), X 615 Can be N or C(R 615 ), X 616 Can be N or C(R 616 ), and X614 To X 616 At least one of may be N,

[0431] L 611 To L 613 Each as reference L 601 Described,

[0432] xe611 to xe613 are each as described with reference to xe1,

[0433] R 611 To R 613 Each as reference R 601 described, and

[0434] R 614 To R 616 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.

[0435] In an embodiment, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 may each independently be 0, 1, or 2.

[0436] The electron transport region may include one selected from the group consisting of Compound ET1 to Compound ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq 3 , BAlq, TAZ, NTAZ or any combination thereof:

[0437]

[0438]

[0439]

[0440]

[0441] The thickness of the electron transport region may be about to about For example, about to about When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may be about to about For example, about to about And the thickness of the electron transport layer can be about to about For example, about to about When the thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer and / or the electron transport region is within these ranges, appropriate or satisfactory electron transport characteristics may be obtained without significantly increasing the driving voltage.

[0442] In addition to the above-mentioned materials, the electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material.

[0443] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and the metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. The ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

[0444] In an embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (Liq) and / or compound ET-D2:

[0445]

[0446] The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 150. The electron injection layer may be in direct contact with the second electrode 150.

[0447] The electron injection layer may have: i) a single-layer structure consisting of a single layer (composed of a single material), ii) a single-layer structure consisting of a single layer (comprising a plurality of different materials), or iii) a multi-layer structure including a plurality of layers (comprising a plurality of different materials).

[0448] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0449] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.

[0450] The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may include oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.) and / or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.

[0451] The alkali metal-containing compound may include: alkali metal oxides, such as Li 2 O, Cs 2 O, and / or K 2 O; alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and / or KI; or any combination thereof. The alkaline earth metal-containing compound may include alkaline earth metal oxides, such as BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying 0 < x < 1) and / or Ba x Ca 1-x O (where x is a real number satisfying 0 < x < 1). The rare earth metal-containing compound may include YbF 3 、ScF 3 、Sc 2 O 3 、Y 2 O 3 、Ce 2 O 3 、GdF 3 、TbF 3 、YbI 3 、ScI 3 、TbI 3 、 or any combination thereof. In an embodiment, the rare earth metal-containing compound may include lanthanide metal tellurides. Examples of lanthanide metal tellurides may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La 2 Te 3 、Ce 2 Te 3 、Pr 2 Te 3 、Nd2 Te 3 、Pm 2 Te 3 、Sm 2 Te 3 、Eu 2 Te 3 , Gd 2 Te 3 , Tb 2 Te 3 、Dy 2 Te 3 、Ho 2 Te 3 , Er 2 Te 3 、Tm 2 Te 3 , Yb 2 Te 3 He Lu 2 Te 3 .

[0452] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may include i) one of the ions of an alkali metal, an alkaline earth metal and a rare earth metal and ii) a ligand bonded to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.

[0453] The electron injection layer may include or consist of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described above. In an embodiment, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).

[0454] In an embodiment, the electron injection layer may include or consist of: i) an alkali metal compound (e.g., an alkali metal halide), ii) a) an alkali metal compound (e.g., an alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. In an embodiment, the electron injection layer may be a KI:Yb co-deposition layer, a RbI:Yb co-deposition layer, and / or a LiF:Yb co-deposition layer, etc.

[0455] When the electron injection layer further includes an organic material, alkali metals, alkaline earth metals, rare earth metals, alkali metal-containing compounds, alkaline earth metal-containing compounds, rare earth metal-containing compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes or any combination thereof can be uniformly or non-uniformly dispersed in the matrix including the organic material.

[0456] The thickness of the electron injection layer may be about to about And for example, it can be about to about When the thickness of the electron injection layer is within the range as described above, appropriate or satisfactory electron injection characteristics may be obtained without significantly increasing the driving voltage.

[0457] The second electrode 150

[0458] The second electrode 150 is on the interlayer 130. The second electrode 150 may be a cathode as an electron injection electrode, and as a material for forming the second electrode 150, metals, alloys, conductive compounds, or any combination thereof each having a low work function may be used.

[0459] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode or a reflective electrode.

[0460] The second electrode 150 may have a single-layer structure or a multi-layer structure including a plurality of layers.

[0461] Capping layer

[0462] The first capping layer may be outside the first electrode 110 and / or the second capping layer may be outside the second electrode 150. In more detail, the organic light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are sequentially stacked in a prescribed order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150 and the second capping layer are sequentially stacked in a prescribed order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150 and the second capping layer are sequentially stacked in a prescribed order.

[0463] Light generated in the emission layer of the interlayer 130 of the organic light-emitting device 10 may be extracted toward the outside through the first electrode 110 as a semi-transmissive electrode or a transmissive electrode and the first capping layer. Light generated in the emission layer of the interlayer 130 of the organic light-emitting device 10 may be extracted toward the outside through the second electrode 150 as a semi-transmissive electrode or a transmissive electrode and the second capping layer.

[0464] The first capping layer and the second capping layer may increase external emission efficiency according to the principle of constructive interference, and accordingly, increase light extraction efficiency of the organic light-emitting device 10 , so that the light emission efficiency of the organic light-emitting device 10 may be increased.

[0465] Each of the first capping layer and the second capping layer may include a material having a refractive index of 1.6 or greater (at a wavelength of 589 nm).

[0466] The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.

[0467] At least one selected from the first capping layer and the second capping layer may each independently include a carbocyclic compound, a heterocyclic compound, an amine-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine-containing compound may be optionally substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In an embodiment, at least one selected from the first capping layer and the second capping layer may each independently include an amine-containing compound.

[0468] In an embodiment, at least one selected from the first capping layer and the second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.

[0469] In an embodiment, at least one selected from the first capping layer and the second capping layer may each independently include one selected from compounds HT28 to HT33, one selected from compounds CP1 to CP6, β-NPB or any combination thereof:

[0470]

[0471] membrane

[0472] The heterocyclic compound represented by Formula 1 may be included in various suitable films. Therefore, according to one or more embodiments, a film including the heterocyclic compound represented by Formula 1 may be provided. The film may be, for example, an optical member (or light control device) (e.g., a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorption layer, a polarization layer and / or a quantum dot content layer, etc.), a light blocking member (e.g., a light reflecting layer and / or a light absorbing layer, etc.) and / or a protective member (e.g., an insulating layer (e.g., an electrical insulating layer) and / or a dielectric layer, etc.).

[0473] Electronic devices

[0474] The organic light-emitting device may be included in various suitable electronic devices. In an embodiment, the electronic device including the organic light-emitting device may be a light-emitting device and / or an authentication device, etc.

[0475] In addition to the organic light-emitting device, the electronic device (e.g., a light-emitting device) may further include i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and / or the color conversion layer may be provided in at least one direction of travel of the light emitted from the organic light-emitting device. In an embodiment, the light emitted from the organic light-emitting device may be blue light and / or white light. The organic light-emitting device may be the same as described above. In an embodiment, the color conversion layer may include quantum dots. The quantum dots may be, for example, quantum dots as described herein.

[0476] The electronic device may include a first substrate, the first substrate may include a plurality of sub-pixel regions, the color filter may include a plurality of color filter regions respectively corresponding to the plurality of sub-pixel regions, and the color conversion layer may include a plurality of color conversion regions respectively corresponding to the plurality of sub-pixel regions.

[0477] A pixel defining film may be provided between the plurality of sub-pixel regions to define each sub-pixel region.

[0478] The color filter may further include a plurality of color filter regions and a light shielding pattern provided between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light shielding pattern provided between the plurality of color conversion regions.

[0479] A plurality of color filter regions (or a plurality of color conversion regions) may include a first region emitting a first color light, a second region emitting a second color light, and / or a third region emitting a third color light, wherein the first color light, the second color light, and / or the third color light may have different maximum emission wavelengths. In an embodiment, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In an embodiment, the plurality of color filter regions (or a plurality of color conversion regions) may include quantum dots. In more detail, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include quantum dots. A detailed description of quantum dots is provided herein. The first region, the second region, and / or the third region may each further include a scatterer (e.g., a light scatterer).

[0480] In an embodiment, the organic light-emitting device may emit a first light, the first region may absorb the first light to emit a first-1 color light, the second region may absorb the first light to emit a second-1 color light, and the third region may absorb the first light to emit a third-1 color light. In some embodiments, the first-1 color light, the second-1 color light, and the third-1 color light may have different maximum emission wavelengths. In more detail, the first light may be blue light, the first-1 color light may be red light, the second-1 color light may be green light, and the third-1 color light may be blue light.

[0481] In addition to the organic light-emitting device described above, the electronic device may further include a thin film transistor. The thin film transistor may include a source electrode, a drain electrode and an active layer, wherein any one selected from the source electrode and the drain electrode may be electrically connected to any one selected from the first electrode and the second electrode of the organic light-emitting device.

[0482] The thin film transistor may further include a gate electrode, a gate insulating film, and the like.

[0483] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, and / or an oxide semiconductor, etc.

[0484] The electronic device may further include a sealing portion that seals the organic light-emitting device. The sealing portion may be between the color filter and / or the color conversion layer and the organic light-emitting device. The sealing portion allows light from the organic light-emitting device to be extracted to the outside, and at the same time (e.g., synchronously) prevents or reduces the penetration of ambient air and / or moisture into the organic light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate and / or a plastic substrate. The sealing portion may be a thin film encapsulation layer including at least one of an organic layer and an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.

[0485] In addition to the color filter and / or color conversion layer, various appropriate functional layers may be additionally on the sealing portion according to the purpose of the electronic device. The functional layer may include a touch screen layer and / or a polarization layer, etc. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, and / or an infrared touch screen layer.

[0486] In addition to the organic light emitting device as described above, the authentication device may further include a biometric information collector. The authentication device may be, for example, a biometric authentication device that authenticates an individual by using biometric information of a living body (eg, fingertips, pupils, etc.).

[0487] The electronic device can be applied to various appropriate displays, light sources, lighting equipment, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game consoles, medical tools (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasonic diagnostic devices and / or endoscope displays), fish finders, various appropriate measuring tools, instruments (e.g., instruments for vehicles, aircraft and / or ships) and / or projectors, etc.

[0488] Electronic equipment

[0489] The organic light emitting device may be included in various suitable electronic devices.

[0490] For example, electronic equipment including an organic light-emitting device can be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a retractable display, a laser printer, a phone, a mobile phone, a tablet computer, a tablet phone, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a 3D display, a virtual reality display, an augmented reality display, a vehicle, a video wall including multiple displays tiled together, a theater screen, a stadium screen, a light therapy device, a sign, an automotive sensor, a home sensor and / or a solar cell.

[0491] Since the organic light-emitting device has excellent photoelectric characteristics, etc., an electronic device including the organic light-emitting device may have an optical sensor function, such as a fingerprint recognition sensor function.

[0492] Figure 2 and Figure 3 Description

[0493] Figure 2 is a cross-sectional view of an electronic device according to an embodiment.

[0494] Figure 2 The electronic device includes a substrate 100, a thin film transistor (TFT), an organic light emitting device, and an encapsulation portion 300 that seals the organic light emitting device.

[0495] The substrate 100 may be a flexible substrate, a glass substrate, and / or a metal substrate. The buffer layer 210 may be on the substrate 100. The buffer layer 210 may prevent or reduce penetration of impurities through the substrate 100, and may provide a flat surface on the substrate 100.

[0496] The TFT may be on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.

[0497] The active layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.

[0498] A gate insulating film 230 that electrically insulates the active layer 220 from the gate electrode 240 may be on the active layer 220 , and the gate electrode 240 may be on the gate insulating film 230 .

[0499] The interlayer insulating film 250 may be on the gate electrode 240. The interlayer insulating film 250 may be between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate (eg, electrically insulate) from each other.

[0500] Source and drain electrodes 260 and 270 may be on interlayer insulating film 250. Interlayer insulating film 250 and gate insulating film 230 may expose source and drain regions of active layer 220, and source and drain electrodes 260 and 270 may contact exposed portions of the source and drain regions of active layer 220.

[0501] The TFT may be electrically connected to the organic light-emitting device to drive the organic light-emitting device, and may be covered and protected by the passivation layer 280. The passivation layer 280 may include an inorganic insulating film (e.g., an inorganic electrical insulating film), an organic insulating film (e.g., an organic electrical insulating film), or any combination thereof. The organic light-emitting device is provided on the passivation layer 280. The organic light-emitting device may include a first electrode 110, an interlayer 130, and a second electrode 150.

[0502] The first electrode 110 may be on the passivation layer 280. The passivation layer 280 may expose a portion of the drain electrode 270 without completely covering the drain electrode 270, and the first electrode 110 may be connected to the exposed portion of the drain electrode 270.

[0503] A pixel defining film 290 including an insulating material (e.g., an electrically insulating material) may be on the first electrode 110. The pixel defining film 290 may expose a specific region of the first electrode 110, and the interlayer 130 may be formed in the exposed region of the first electrode 110. The pixel defining film 290 may be a polyimide-based organic film and / or a polyacrylic organic film. In some embodiments, at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel defining film 290 to be in the form of a common layer.

[0504] The second electrode 150 may be on the interlayer 130, and the capping layer 170 may be additionally on the second electrode 150. The capping layer 170 may cover the second electrode 150.

[0505] The encapsulation portion 300 may be on the capping layer 170. The encapsulation portion 300 may be on the organic light-emitting device to protect the organic light-emitting device from moisture and / or oxygen. The encapsulation portion 300 may include an inorganic film including silicon nitride (SiN x ), silicon oxide (SiO x ), indium tin oxide, indium zinc oxide or any combination thereof; an organic film comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyvinyl sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resin (e.g., polymethyl methacrylate and / or polyacrylic acid, etc.), epoxy resin (e.g., aliphatic glycidyl ether (AGE), etc.) or any combination thereof; or a combination of an inorganic film and an organic film.

[0506] Figure 3 is a cross-sectional view of an electronic device according to another embodiment.

[0507] Figure 3 Electronic equipment and Figure 2 The electronic device is substantially the same as the one of the embodiment of the present invention, except that the light shielding pattern 500 and the functional area 400 are additionally on the packaging portion 300. The functional area 400 may be i) a color filter area, ii) a color conversion area, or iii) a combination of a color filter area and a color conversion area. In an embodiment, Figure 3 The organic light-emitting device included in the electronic device may be a tandem organic light-emitting device.

[0508] Figure 4 Description

[0509] Figure 4Schematic perspective view of an electronic device 1 including an organic light-emitting device according to an embodiment. As a device for displaying moving images and / or still images, the electronic device 1 may be a portable electronic device, such as a mobile phone, a smart phone, a tablet personal computer (PC), a mobile communication terminal, an electronic notebook computer, an e-book, a portable multimedia player (PMP), a navigation and / or an ultra mobile PC (UMPC), and various suitable products, such as a television, a laptop computer, a monitor, a billboard and / or an Internet of Things (IOT) device. The electronic device 1 may be such a product or a part thereof. In some embodiments, the electronic device 1 may be a wearable device, such as a smart watch, a watch phone, a glasses-type display and / or a head-mounted display (HMD) or a part of a wearable device. However, the embodiments are not limited thereto. For example, the electronic device 1 may include a dashboard of a vehicle, a center console of a vehicle, a central information display on the dashboard of a vehicle, an interior rearview mirror display replacing a side mirror of a vehicle, an entertainment display for a rear seat of a vehicle, a display on a backrest of a front seat, a head-up display (HUD) mounted on the front of the vehicle and / or projected on the front windshield, or a computer generated hologram augmented reality head-up display (CGH AR HUD). For convenience of explanation, Figure 4 Explained is the case where the electronic equipment 1 is a smart phone.

[0510] The electronic equipment 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device may realize an image through a plurality of pixel arrays two-dimensionally provided in the display area DA.

[0511] The non-display area NDA is an area where no image is displayed, and may completely surround the display area DA. In the non-display area NDA, a driver for providing an electrical signal and / or power to the display element in the display area DA may be provided. In the non-display area NDA, a pad may be provided, which may be electrically connected to an electronic element and / or a printed circuit board.

[0512] In the electronic device 1, the length in the x-axis direction and the length in the y-axis direction may be different from each other. Figure 4 As shown in , the length in the x-axis direction may be less than the length in the y-axis direction. In an embodiment, the length in the x-axis direction may be the same as the length in the y-axis direction. In an embodiment, the length in the x-axis direction may be greater than the length in the y-axis direction.

[0513] Figure 5 and FIG. 6A to FIG. 6C Description

[0514] Figure 5 is a schematic diagram of the exterior of a vehicle 1000 as an electronic device including an organic light emitting device according to an embodiment. FIG. 6A to FIG. 6C Each is a schematic diagram of the interior of a vehicle 1000 according to one or more embodiments.

[0515] See also Figure 5 , Fig. 6A , Figure 6B and Figure 6C The vehicle 1000 may refer to various suitable devices for moving an object to be transported (such as a person, an object, and / or an animal) from a starting point to a destination point. The vehicle 1000 may include a vehicle traveling on roads and / or tracks, a ship moving on the sea and / or a river, and / or an airplane flying in the air using the action of air.

[0516] The vehicle 1000 may travel on roads and / or tracks. The vehicle 1000 may move in a specific direction according to the rotation of at least one wheel. In an embodiment, the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, an engineering machine, a two-wheeled vehicle, a prime mover device, a bicycle, and / or a train traveling on tracks.

[0517] The vehicle 1000 may include a body having an interior and an exterior, and a chassis in which a mechanical device useful or required for driving is installed as other parts outside the body. The exterior of the body may include a front panel, a hood, a roof panel, a rear panel, a trunk, and / or pillars provided at the boundaries between doors, etc. The chassis of the vehicle 1000 may include a power generation device, a power transmission device, a drive device, a steering device, a brake device, a suspension device, a transmission device, a fuel device, front wheels and rear wheels and / or left wheels and right wheels, etc.

[0518] The vehicle 1000 may include side window glasses 1100 , a front window glass 1200 , side view mirrors 1300 , an instrument cluster 1400 , a center console 1500 , a passenger seat instrument panel 1600 , and a display device 2 .

[0519] The side window glass 1100 and the front window glass 1200 may be divided by pillars between the side window glass 1100 and the front window glass 1200 .

[0520] The side window glass 1100 may be installed on the side of the vehicle 1000. In an embodiment, the side window glass 1100 may be installed on a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided and may face each other. In an embodiment, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In an embodiment, the first side window glass 1110 may be adjacent to the instrument cluster 1400. The second side window glass 1120 may be adjacent to the passenger seat instrument panel 1600.

[0521] In an embodiment, the side window glass 1100 may be spaced apart from each other in the x-axis direction or the -x-axis direction (the direction opposite to the x-axis direction). In an embodiment, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the x-axis direction or the -x-axis direction. In some embodiments, the imaginary straight line L connecting the side window glass 1100 may extend in the x-axis direction or the -x-axis direction. In an embodiment, the imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 to each other may extend in the x-axis direction or the -x-axis direction.

[0522] The front window glass 1200 may be installed at the front of the vehicle 1000. The front window glass 1200 may be between the side window glasses 1100 facing each other.

[0523] The side view mirror 1300 may provide a rear view of the vehicle 1000. The side view mirror 1300 may be mounted on the exterior of the vehicle body. In an embodiment, a plurality of side view mirrors 1300 may be provided. Any one selected from the plurality of side view mirrors 1300 may be outside the first side window glass 1110. Another one of the plurality of side view mirrors 1300 may be outside the second side window glass 1120.

[0524] Instrument cluster 1400 may be in front of the steering wheel. Instrument cluster 1400 may include a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge, a turn indicator, a high beam indicator, warning lights, a seat belt warning light, an odometer, a speedometer, an automatic shift lever indicator light, a door open warning light, an engine oil warning light, and / or a low fuel warning light.

[0525] The center console 1500 may include a control panel on which a plurality of buttons for adjusting an audio device, an air conditioning device, and a seat heater are provided. The center console 1500 may be on one side of the instrument cluster 1400 .

[0526] The passenger seat instrument panel 1600 may be spaced apart from the instrument cluster 1400, with the center console 1500 being between the passenger seat instrument panel 1600 and the instrument cluster 1400. In an embodiment, the instrument cluster 1400 may correspond to the driver's seat, and the passenger seat instrument panel 1600 may correspond to the passenger seat. In an embodiment, the instrument cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat instrument panel 1600 may be adjacent to the second side window glass 1120.

[0527] In an embodiment, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be inside the vehicle 1000. In an embodiment, the display device 2 may be between the side window glasses 1100 facing each other. The display device 2 may be on at least one selected from the instrument cluster 1400, the center console 1500, and the passenger seat instrument panel 1600.

[0528] The display device 2 may include an organic light emitting display, an inorganic EL display and / or a quantum dot display. Hereinafter, an organic light emitting display device including an organic light emitting device according to the present disclosure will be described as an example of the display device 2 according to an embodiment, but various suitable types (or kinds) of display devices as described above may be used in the embodiment.

[0529] See also Fig. 6A , the display device 2 may be on the center console 1500. In an embodiment, the display device 2 may display navigation information. In an embodiment, the display device 2 may display audio, video and / or information about vehicle settings.

[0530] See also Figure 6B , the display device 2 may be on the instrument cluster 1400. In some embodiments, the instrument cluster 1400 may display driving information and the like through the display device 2. In some embodiments, the instrument cluster 1400 may be implemented digitally. The instrument cluster 1400 may digitally display vehicle information and driving information as images. In an embodiment, the needle and instrument of the tachometer and various appropriate warning light icons may be displayed through digital signals.

[0531] See also Figure 6C , the display device 2 may be on the passenger seat instrument panel 1600. The display device 2 may be embedded in and / or on the passenger seat instrument panel 1600. In an embodiment, the display device 2 on the passenger seat instrument panel 1600 may display an image related to the information displayed on the instrument cluster 1400 and / or the information displayed on the center console 1500. In an embodiment, the display device 2 on the passenger seat instrument panel 1600 may display information different from the information displayed on the instrument cluster 1400 and / or the information displayed on the center console 1500.

[0532] Manufacturing method

[0533] The layer constituting the hole transport region, the emission layer and the layer constituting the electron transport region can be formed in a set or specific area by using various appropriate methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing and / or laser induced thermal imaging.

[0534] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition temperature may be about 100° C. to about 500° C., about 10 -8 To about 10 -3 Torr vacuum and about to about Deposition is carried out at a deposition rate of .

[0535] Definition of terms

[0536] As used herein, the term "C 3 -C 60 "Carbocyclic group" refers to a cyclic group consisting only of carbon as a ring atom and having 3 to 60 carbon atoms, for example, 3 -C 50 Carbocyclic group, C 3 -C 40 Carbocyclic group, C 3 -C 30 Carbocyclic group, C 3 -C 20 Carbocyclic or C 3 -C 10 Carbocyclic groups, and as used herein, the term "C 1 -C 60 The "heterocyclic group" refers to a cyclic group having 1 to 60 carbon atoms and further including heteroatoms as ring-forming atoms in addition to carbon atoms, for example, C 1 -C 50 Heterocyclic group, C 1 -C 40 Heterocyclic group, C 1 -C 30 Heterocyclic group, C 1 -C 20 Heterocyclic or C 1 -C 10 Heterocyclic group. 3 -C 60 Carbocyclic and C 1 -C 60 The heterocyclic groups may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are fused to each other. 1 -C 60 The number of ring-forming atoms of the heterocyclic group may be 3 to 61.

[0537] As used herein, the term "cyclic group" may include C 3 -C 60 Carbocyclic and C 1 -C 60 Both heterocyclic groups.

[0538] As used herein, the term "π-electron-rich C 3 -C 60 The term "cyclic group" refers to a cyclic group having 3 to 60 carbon atoms and not including *-N=*' as a ring-forming part, and the term "π-electron-deficient nitrogen-containing C 1 -C 60 The "cyclic group" refers to a heterocyclic group having 1 to 60 carbon atoms and including *-N=*' as a ring-forming part.

[0539] In an embodiment,

[0540] C 3 -C 60 The carbocyclic group may be i) a group T1 or ii) a fused ring group in which two or more groups T1 are fused to each other (e.g., cyclopentadienyl, adamantyl, norbornyl, phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylene, peryl, pentaphenanthrenyl, heptalenyl, tetracenyl, phenanthrenyl, hexenyl, pentacenyl, rubenyl, coronenyl, ovalenyl, indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl or indenoanthryl),

[0541] C 1 -C 60 The heterocyclic group may be i) a group T2, ii) a condensed ring group in which two or more groups T2 are condensed to each other, or iii) a condensed ring group in which at least one group T2 and at least one group T1 are condensed to each other (e.g., pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiorolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiorolyl, dibenzothiophenyl, dibenzofuranyl, indenocarbazolyl, indolecarbazolyl, benzofuranocarbazolyl, benzothiophenylcarbazolyl, benzothiorolocarbazolyl, benzoindolcarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, benzonaphthothiorolyl, benzofuranodibenzofuranyl , benzofuranodibenzothiophenyl, benzothiophenodibenzothiophenyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl yl, benzoquinolyl, benzisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazoline, benzoquinazolinyl, phenanthroline, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazine, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiazolyl, azadibenzothiopheneyl, azadibenzofuranyl, etc.),

[0542] Pi-electron-rich C 3 -C 60The cyclic group may be i) a group T1, ii) a fused ring group in which two or more groups T1 are fused to each other, iii) a group T3, iv) a fused ring group in which two or more groups T3 are fused to each other, or v) a fused ring group in which at least one group T3 and at least one group T1 are fused to each other (e.g., C 3 -C 60 carbocyclic group, 1H-pyrrolyl, thiolyl, borocyclopentadienyl, 2H-pyrrolyl, 3H-pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiolyl, dibenzothiophenyl, dibenzofuranyl, indenocarbazolyl, indolecarbazolyl, benzofuranocarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzoindolcarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, benzonaphthothiolyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl or benzothiophenyldibenzothiophenyl, etc.),

[0543] π-electron-deficient nitrogen-containing C 1 -C 60 The cyclic group may be i) a group T4, ii) a fused ring group in which two or more groups T4 are fused to each other, iii) a fused ring group in which at least one group T4 and at least one group T1 are fused to each other, iv) a fused ring group in which at least one group T4 and at least one group T3 are fused to each other, or v) a fused ring group in which at least one group T4, at least one group T1 and at least one group T3 are fused to each other (e.g., pyrazolyl, imidazole, triazole, oxazolyl, isoxazolyl, oxadiazole, thiazolyl, isothiazolyl, thiadiazole yl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiazolyl, azadibenzothiopheneyl, azadibenzofuranyl, and the like),

[0544] The radical T1 can be cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornane (or bicyclo[2.2.1]heptane) group, norbornyl, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane or phenyl,

[0545] The radical T2 can be furanyl, thienyl, 1H-pyrrolyl, thiolyl, borocyclopentyl, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathiolyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetraazinyl, pyrrolidinyl, imidazolidinyl, dihydropyrrolyl, piperidinyl, tetrahydropyridinyl, dihydropyridinyl, hexahydropyrimidinyl, tetrahydropyrimidinyl, dihydropyrimidinyl, piperazinyl, tetrahydropyrazinyl, dihydropyrazinyl, tetrahydropyridazinyl or dihydropyridazinyl,

[0546] The group T3 may be furyl, thienyl, 1H-pyrrolyl, thiolyl or borocyclopentadienyl, and

[0547] The group T4 can be 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathioyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl or tetrazinyl.

[0548] As used herein, the terms "cyclic group", "C 3 -C 60 Carbocyclic group, "C 1 -C 60 Heterocyclic group", "π-electron-rich C 3 -C 60 Cyclic group" or "π-electron-deficient nitrogen-containing C 1 -C 60 The "cyclic group" may refer to a group fused to any cyclic group, a monovalent group or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.). In an embodiment, the "phenyl group" may be a benzo group, a phenyl group or a phenylene group, etc., and those of ordinary skill in the art may easily understand these groups based on the structure of the formula including the "phenyl group".

[0549] In an embodiment, the unit price C 3 -C 60 Carbocyclic groups and monovalent C 1 -C 60 Examples of the heterocyclic group may include C3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group, and a divalent C 3 -C 60 Carbocyclic groups and divalent C 1 -C 60 Examples of the heterocyclic group may include C 3 -C 10 Cycloalkylene, C 1 -C 10 Heterocycloalkylene, C 3 -C 10 Cycloalkenylene, C 1 -C 10 Heterocycloalkenylene, C 6 -C 60 Arylene, C 1 -C 60 a heteroarylene group, a divalent non-aromatic fused polycyclic group, and a divalent non-aromatic fused heteropolycyclic group.

[0550] As used herein, the term "C 1 -C 60 "Alkyl" refers to a straight or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, for example, 1 -C 50 Alkyl, C 1 -C 30 Alkyl, C 1 -C 20 Alkyl or C 1 -C 10 The term "alkyl" as used herein includes methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, and tert-decyl. As used herein, the term "C 1 -C 60 "Alkylene" refers to C 1 -C 60 The alkyl group has substantially the same structure as a divalent group.

[0551] As used herein, the term "C 2 -C 60 "Alkenyl" refers to 2 -C 60 The alkyl group is a monovalent hydrocarbon group having at least one carbon-carbon double bond in the main chain (e.g., in the middle) or at the end (e.g., terminal) of the alkyl group. 2 -C 30 Alkenyl, C 2 -C 20 Alkenyl or C 2 -C 10 The term "C-alkenyl" as used herein includes vinyl, propenyl and butenyl. 2 -C 60 "Alkenylene" refers to C 2 -C 60 The alkenyl group has a divalent group having substantially the same structure.

[0552] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a C 2 -C 60 The alkyl group is a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the main chain (e.g., in the middle) or at the end (e.g., terminal) of the alkyl group. 2 -C 30 Alkynyl, C 2 -C 20 Alkynyl or C 2 -C 10 The term "C ynyl" as used herein includes ethynyl and propynyl. 2 -C 60 "Alkynylidene" refers to a C 2 -C 60 Alkynyl groups have substantially the same structure as a divalent group.

[0553] As used herein, the term "C 1 -C 60 "Alkoxy" refers to -OA 101 (A 101 C 1 -C 60 Alkyl) represented by a monovalent group, for example, C 1 -C 30 Alkoxy, C 1 -C 20 Alkoxy or C 1 -C 10 An alkoxy group, and examples thereof include a methoxy group, an ethoxy group, and an isopropoxy group.

[0554] As used herein, the term "C3 -C 10 The term "cycloalkyl" as used herein refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, and bicyclo[2.2.2]octyl. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, and bicyclo[2.2.2] 3 -C 10 "Cycloalkylene" refers to 3 -C 10 The cycloalkyl group has a divalent group having substantially the same structure.

[0555] As used herein, the term "C 1 -C 10 The term "heterocycloalkyl" as used herein refers to a monovalent cyclic group having 1 to 10 carbon atoms and further including at least one heteroatom as a ring-forming atom in addition to carbon atoms, and examples thereof include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl, tetrahydrothienyl, and the like. 1 -C 10 "Heterocycloalkylene" refers to a C 1 -C 10 The heterocycloalkyl group has substantially the same structure as a divalent group.

[0556] As used herein, the term "C 3 -C 10 The term "cycloalkenyl" as used herein refers to a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and having no aromaticity (e.g., not aromatic), and examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. 3 -C 10 "Cycloalkenylene" refers to 3 -C 10 The cycloalkenyl group has a divalent group having substantially the same structure.

[0557] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl group" refers to a monovalent cyclic group having 1 to 10 carbon atoms, further including at least one heteroatom as a ring-forming atom in addition to carbon atoms, and having at least one double bond in its ring. 1 -C 10 Examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. As used herein, the term “C 1 -C 10 "Heterocycloalkenylene" refers to a C 1 -C10 The heterocycloalkenyl group has a divalent group having substantially the same structure.

[0558] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms, for example, 6 -C 50 Aryl, C 6 -C 40 Aryl, C 6 -C 30 Aryl, C 6 -C 20 Aryl or C 6 -C 15 Aryl, and as used herein the term "C 6 -C 60 "Arylene" refers to a divalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Examples of aryl groups include phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, perylenyl, pentaphenanthrenyl, heptalenyl, tetracenyl, phenanthrenyl, hexenyl, pentacene, rubenyl, coronenyl, and ovalenyl. 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the two or more rings may be fused to each other.

[0559] As used herein, the term "C 1 -C 60 The term "heteroaryl" refers to a monovalent group having a heterocyclic aromatic system, which has 1 to 60 carbon atoms and further includes at least one heteroatom as a ring-forming atom in addition to carbon atoms, for example, C 1 -C 50 Heteroaryl, C 1 -C 40 Heteroaryl, C 1 -C 30 Heteroaryl, C 1 -C 20 Heteroaryl or C 1 -C 10 As used herein, the term "C 1 -C 60 The term "heteroarylene group" refers to a divalent group having a heterocyclic aromatic system, which has 1 to 60 carbon atoms and further includes at least one heteroatom as a ring-constituting atom in addition to carbon atoms. 1 -C 60Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, and naphthyridinyl. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include two or more rings, the two or more rings may be fused to each other.

[0560] As used herein, the term "monovalent non-aromatic fused polycyclic group" refers to a monovalent group having two or more rings fused to each other, having only carbon atoms (e.g., 8 to 60 carbon atoms) as ring-forming atoms, and having no aromaticity in its molecular structure when considered as a whole (e.g., not aromatic when considered as a whole), for example, C 8 -C 60 Monovalent non-aromatic fused polycyclic group, C 8 -C 50 Monovalent non-aromatic fused polycyclic group, C 8 -C 40 Monovalent non-aromatic fused polycyclic group, C 8 -C 30 A monovalent non-aromatic fused polycyclic group or C 8 -C 20 Monovalent non-aromatic fused polycyclic group. Examples of monovalent non-aromatic fused polycyclic groups include indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl and indenoanthryl. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic fused polycyclic group.

[0561] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group having two or more rings fused to each other, further including at least one heteroatom as a ring-constituting atom in addition to carbon atoms (e.g., 1 to 60 carbon atoms), and having no aromaticity in its molecular structure when considered as a whole (e.g., not aromatic when considered as a whole), for example, C 1 -C 60 Monovalent non-aromatic fused heteropolycyclic group, C 1 -C 50 Monovalent non-aromatic fused heteropolycyclic group, C 1 -C 40 Monovalent non-aromatic fused heteropolycyclic group, C 1 -C 30 A monovalent non-aromatic fused heteropolycyclic group or C 1 -C 20Monovalent non-aromatic condensed heteropolycyclic group. Examples of the monovalent non-aromatic condensed heteropolycyclic group include pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothioyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothioyl, dibenzothiophenyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzothioyl, azadibenzothiophenyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having substantially the same structure as a monovalent non-aromatic fused heteropolycyclic group.

[0562] As used herein, the term "C 6 -C 60 "Aryloxy" refers to -OA 102 (A 102 C 6 -C 60 Aryl), for example, C 6 -C 50 Aryloxy, C 6 -C 40 Aryloxy, C 6 -C 30 Aryloxy, C 6 -C 20 Aryloxy or C 6 -C 15 Aryloxy, and as used herein the term "C 6 -C 60 "Arylthio" refers to -SA 103 (A 103 C 6 -C 60 Aryl), for example, C 6 -C 50 Arylthio, C 6 -C 40 Arylthio, C 6 -C 30 Arylthio, C 6 -C 20 Arylthio or C6 -C 15 Arylthio.

[0563] As used herein, the term "C 7 -C 60 "Aralkyl" refers to -A 104 A 105 (A 104 C 1 -C 54 Alkylene, and A 105 C 6 -C 59 Aryl), for example, C 7 -C 50 Aralkyl, C 7 -C 40 Aralkyl, C 7 -C 30 Aralkyl, C 7 -C 20 Arylalkyl or C 7 -C 15 Aralkyl, and as used herein the term "C 2 -C 60 "Heteroaralkyl" refers to -A 106 A 107 (A 106 C 1 -C 59 Alkylene, and A 107 C 1 -C 59 Heteroaryl), for example, C 2 -C 50 Heteroarylalkyl, C 2 -C 40 Heteroarylalkyl, C 2 -C 30 Heteroarylalkyl, C 2 -C 20 Heteroaralkyl or C 2 -C 15 Heteroaralkyl.

[0564] As used herein, the term " 10a " can be:

[0565] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0566] Each unsubstituted or substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof;

[0567] Each unsubstituted or substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or

[0568] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ).

[0569] As used in this paper, Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60alkoxy; or each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl.

[0570] As used herein, the term "heteroatom" refers to any atom other than a carbon atom and a hydrogen atom. Examples of heteroatoms include O, S, N, P, Si, B, Ge, Se, or any combination thereof.

[0571] As used herein, "Ph" refers to phenyl, as used herein, "Me" refers to methyl, as used herein, "Et" refers to ethyl, as used herein, "ter-Bu" or "Bu" refers to ethyl. t " refers to a tert-butyl group, and "OMe" as used herein refers to a methoxy group.

[0572] As used herein, the term "biphenyl" refers to a "phenyl group substituted by a phenyl group". 6 -C 60 A phenyl group substituted with an aryl group as a substituent.

[0573] As used herein, the term "terphenyl" refers to a "phenyl group substituted by a biphenyl group". 6 -C 60 Aryl substituted C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.

[0574] In this article, the x-axis, y-axis, and z-axis are not limited to the three axes in the orthogonal coordinate system, and can be broadly interpreted as including these axes. For example, the x-axis, y-axis, and z-axis can refer to those axes that are orthogonal to each other, or can refer to those axes in different directions that are not orthogonal to each other.

[0575] Unless otherwise defined, *, *' and *" as used herein each refer to a binding site to an adjacent atom in the corresponding formula or moiety.

[0576] Hereinafter, the compound according to the embodiment and the organic light-emitting device according to the embodiment will be described in more detail with reference to the following synthesis examples and examples. The phrase "using B instead of A" used in describing the synthesis examples means using B instead of A with the same molar equivalent.

[0577] Example

[0578] Synthesis Example 1: Synthesis of Compound 1

[0579]

[0580] (1) Synthesis of compound [1-A]

[0581] In a three-necked flask, 1,3-dibromo-5-fluorobenzene (25 g, 98.46 mmol) and 2,6-dimethylphenol (18.0 g, 147.69 mmol) were dissolved in 100.0 ml of NMP, and potassium carbonate (40.8 g, 295.38 mmol) was added thereto, followed by stirring at 150 ° C. under reflux conditions in a nitrogen atmosphere for 12 hours. After the reaction was completed, the resulting mixture was cooled to room temperature, and 300 mL of water was added to terminate the reaction. After an extraction process was performed using water and dichloromethane, the mixture was quenched by using MgSO 4 Water was removed from the obtained organic layer. The organic layer was concentrated and separated by column chromatography using MC and hexane to obtain solid compound [1-A]. (30.9 g, 88.3%)

[0582] 1 H NMR (300 MHz, CD 2 Cl 2 ): δ7.70(m,1H),7.28(s,2H),7.15(m,1H),7.02(m,2H),2.14(s,6H).

[0583] (2) Synthesis of compound [1-B]

[0584] In a three-necked flask, compound [1-A] (21.28 g, 59.76 mmol), 2,6-dimethylaniline (7.2 g, 59.76 mmol), sodium tert-butoxide (NaOtBu) (6.89 g, 71.71 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 ) (0.547 g, 0.59 mmol) and BINAP (1.11 g, 1.79 mmol) were dissolved in 300 ml of toluene, and then refluxed at 100° C. for 6 hours. After the reaction was completed, the resulting mixture was cooled to room temperature and the solvent was concentrated, and the resulting product was separated by column chromatography using MC and hexane to obtain compound [1-B] (14.9 g, 63.2%).

[0585] 1 H NMR (300MHz, CD 2 Cl2 ): δ10.02(s,1H),7.15-7.02(m,7H),6.80(m,1H),2.15-2.12(d,12H).

[0586] (3) Synthesis of compound [1-C]

[0587] In a three-necked flask, compound [1-B] (14.0 g, 30.27 mmol), iodobenzene (9.2 g, 45.41 mmol), sodium tert-butoxide (4.3 g, 45.00 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.27 g, 0.3 mmol) and 1.0 M tri-tert-butylphosphine (P(t-Bu) 3 ) (2.96 ml, 2.96 mmol) was dissolved in 200 ml of toluene, and then refluxed at 130° C. for 7 hours. After the reaction was completed, the resulting mixture was cooled to room temperature and the solvent was concentrated, and the resulting product was separated by column chromatography using MC and hexane to obtain compound [1-C] (13.2 g, 79.2%).

[0588] 1 H NMR (300MHz, CD 2 Cl 2 ): δ7.24(m,2H),7.15-6.94(m,11H),6.80(d,1H),2.15-2.12(d,12H).

[0589] (4) Synthesis of compound [1-D]

[0590] In a three-necked flask, compound [1-C] (11.6 g, 24.55 mmol), di-o-tolylbenzene-1,3-diamine (3.54 g, 12.27 mmol), sodium tert-butoxide (7.07 g, 73.62 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.11 g, 0.12 mmol) and 1.0 M tri-tert-butylphosphine (1.2 ml, 1.2 mmol) were dissolved in 200 ml of toluene, and then refluxed for 7 hours. After the reaction was completed, the resulting mixture was cooled to room temperature and the solvent was concentrated, and the resulting product was separated by column chromatography using MC and hexane to obtain compound [1-D] (8.4 g, 64.5%).

[0591] 1 H NMR (300MHz, CD 2 Cl 2): δ7.27(s,1H),7.24(m,4H),7.19(m,2H),7.15(m,4H),7.13-7.12(m,4H),7.08(m,4H),7.05-7.02( m,8H),7.00-6.91(m,4H),6.83(s,1H),6.75(m,2H),6.52-6.54(m,6H),2.15(s,12H),2.12(s,18H).

[0592] (5) Synthesis of Compound 1

[0593] In a three-necked flask, compound [1-D] (8 g, 7.46 mmol) was dissolved in 50 ml of dichlorobenzene (o-DCB), and then BBr was added thereto. 3 (5.6 ml, 59.73 mmol), and then refluxed at 180° C. for 20 hours. After the reaction was completed, the resulting mixture was cooled to room temperature, N,N-diisopropylethylamine (0.39 g, 1.00 mmol) was added thereto at 0° C., and then 300 ml of water was added thereto to terminate the reaction. After an extraction process was performed by using water and dichloromethane, the mixture was dried by using MgSO 4 Water was removed from the organic layer. The organic layer was concentrated and separated by column chromatography using toluene and hexane, and then purified by recrystallization using toluene and acetonitrile to obtain Compound 1 (1.8 g, 22.2%).

[0594] 1 H NMR (300MHz, CD 2 Cl 2 ): δ7.24(m,2H),7.19(m,2H),7.15(m,4H),7.13-7.12(m,4H),7.08(m,4H),7.05-7.02( m,6H),7.00-6.91(m,4H),6.75(m,2H),6.52-6.54(m,6H),2.15(s,12H),2.12(s,18H).

[0595] C 76 H 64 B 2 N 4 O 2 Calculated value 1086.99 Measured value 1086.52

[0596] Synthesis Example 2: Synthesis of Compound 27

[0597]

[0598] (1) Synthesis of compound [27-A]

[0599] In a three-necked flask, 20 g of 2,6-dimethylaniline (165.594 mmol, 1.3 equivalents), 20 g of bromobenzene (127.380 mmol, 1 equivalent), 24.5 g of NaOtBu (254.76 mmol, 2.0 equivalents), 1.75 g of Pd 2 (dba) 3 (1.911 mmol, 0.015 eq.) and 2 M BINAP (3.821 mmol, 0.03 eq.) were dissolved in toluene (300 ml). The temperature was raised to 130 °C and the resulting mixture was stirred overnight. After confirming the completion of the reaction, an extraction process was performed using DCM, and the reaction mixture was quenched by using MgSO 4 Residual moisture was removed from the obtained organic layer, and the organic layer was filtered under reduced pressure to be concentrated. After column purification by using a developing solvent (Hex:DCM in a ratio of 4:1), the obtained product was cooled to obtain 21.1 g (yield: 84%) of compound [27-A].

[0600] (2) Synthesis of compound [27-B]

[0601] In a three-necked flask, 10 g of 2,6-di-tert-butylphenol (48.466 mmol, 1 equivalent), 12.3 g of 1,3-dibromo-5-fluorobenzene (48.466 mmol, 1 equivalent) and 10 g of K 2 CO 3 (72.699 mmol, 1.5 equivalents). After the temperature was raised to 160°C, the resulting mixture was stirred overnight. After the reaction was completed, an extraction process was performed using ether, and the mixture was purified by using MgSO 4 Residual moisture was removed from the obtained organic layer, and the organic layer was filtered under reduced pressure and then concentrated. After column purification by using a developing solvent (Hex:DCM in a ratio of 8:1), the obtained product was cooled to obtain 10.8 g (yield: 51%) of compound [27-B].

[0602] (3) Synthesis of compound [27-C]

[0603] In a three-necked flask, 10 g of compound [27-B] (22.716 mmol, 1 equivalent), 4.48 g of compound [27-A] (22.716 mmol, 1 equivalent), 4.4 g of NaOtBu (45.432 mmol, 2.0 equivalent), 0.31 g of Pd 2 (dba) 3(0.341mmol, 0.015eq) and xanthene (0.681mmol, 0.03eq) were dissolved in toluene (250ml). The temperature was raised to 130°C and the resulting mixture was stirred overnight. After confirming the completion of the reaction, an extraction process was performed using DCM, and the reaction mixture was dried using MgSO 4 Residual moisture was removed from the obtained organic layer, and the organic layer was filtered under reduced pressure and then concentrated. After column purification by using a developing solvent (Hex:DCM in a ratio of 4:1), the obtained product was cooled to obtain 6.9 g (yield: 55%) of compound [27-C].

[0604] (4) Synthesis of compound [27-D]

[0605] In a three-necked flask, 12.7 g of compound [27-C] (22.885 mmol, 2.2 equivalents), 3 g of N1, N3-diphenylbenzene-1, 3-diamine (10.402 mmol, 1 equivalent), 4 g of NaOtBu (41.608 mmol, 4.0 equivalents), 0.28 g of Pd 2 (dba) 3 (0.312 mmol, 0.03 eq.) and 2M P(t-Bu) 3 (0.624 mmol, 0.06 equivalent) was dissolved in toluene (200 ml). After the temperature was raised to 130°C, the resulting mixture was stirred overnight. After confirming the completion of the reaction, an extraction process was performed using DCM, and the mixture was quenched by using MgSO 4 Residual moisture was removed from the obtained organic layer, and the organic layer was filtered under reduced pressure and then concentrated. After column purification by using a developing solvent (Hex:DCM in a ratio of 4:1), the obtained product was cooled to obtain 8.8 g (yield: 69%) of a solid compound [27-D].

[0606] (5) Synthesis of Compound 27

[0607] In a three-necked flask, 1 g of compound [27-D] (0.807 mmol, 1 equivalent) was dissolved in 1,2,4-trichlorobenzene (1,2,4-TCB) (25 ml), and then 0.6 ml of BBr 3(6.456mmol, 8 equivalents) was injected therein. After the temperature was raised to 185°C, the resulting mixture was stirred overnight. After the mixture was cooled to room temperature, 2.1ml of N, N-diisopropylethylamine (12.105mmol, 15.0 equivalents) was added dropwise thereto, and then stirred at 0°C for 2 hours. After the reaction was completed, silica was placed on a silica filter, and the mixture was filtered through a silica filter under reduced pressure using toluene, and then concentrated. After column purification was performed by using a developing reagent (Hex:THF in a ratio of 7:1), a recrystallization process was performed thereon using Tol / Hex to obtain 0.19g (yield: 19%) of a transparent yellow solid compound 27.

[0608] 1 H NMR (300MHz, CD 2 Cl 2 ): δ10.574(s,1H),9.25(d,2H,J=0.03Hz),7.518-7.485(dd,6H,J=0.06Hz,J=0.02Hz),7.351-7.154(m,15H),7.025-6.979 (m,2H),6.891(s,6H),6.779(d,2H,J=0.06Hz),1.941(m,12H),1.898-1.884(m,12H),1.851-1.837(m,12H),1.292(s,18H).

[0609] C 88 H 88 B 2 N 4 O 2 Calculated value 1255.33 Measured value 1054.71

[0610] Synthesis Example 3: Synthesis of Compound 25

[0611] Compound 25 was synthesized in substantially the same manner as the synthesis of Compound 1, except that in the synthesis of Compound [1-A] of Synthesis Example 1, 2,6-diphenylphenol was used instead of 2,6-dimethylphenol.

[0612] 1 H NMR (300MHz, CD 2 Cl 2 ): δ8.05(d,4H),7.71(dd,2H),7.51-7.41(m,22H),7.29-7.00(m,22H),7.00-6.91(m,4H),6.83(s,1H),6.51-6.52(s,3H),4.23(s,2H).

[0613] C 91 H 60 B 2 N 4 O 2 Calculated value 1263.49, measured value 1263.13

[0614] Synthesis Example 4: Synthesis of Compound 26

[0615] Compound 26 was synthesized in substantially the same manner as the synthesis of Compound 1, except that in the synthesis of Compound [1-A] of Synthesis Example 1, 2,6-di-tert-butylphenol was used instead of 2,6-dimethylphenol.

[0616] 1 H NMR (300MHz, CD 2 Cl 2 ): δ7.71(dd,2H),7.41-6.94(m,31H),6.52-6.74(m,4H),6.18(d,1H),5.37(s,1H),5.29(s,1H),3.3(t,2H),2.1(m,2H),1.40(s,36H).

[0617] C 82 H 80 B 2 N 4 O 2 Calculated value 1174.65, measured value 1175.19

[0618] Example 1

[0619] As the anode, Corning 15Ω / cm 2 The ITO glass substrate was cut into a size of 50 mm×50 mm×0.7 mm, cleaned by ultrasonication using isopropyl alcohol and pure water for 5 minutes each, and then irradiated with ultraviolet rays and exposed to ozone for 30 minutes. Then, the glass substrate was loaded on a vacuum deposition apparatus.

[0620] 2-TNATA was vacuum deposited on the substrate to form a hole injection layer having a thickness of 60 nm, and then, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter referred to as NPB) as a hole transport material was vacuum deposited thereon as a hole transport layer compound to form a hole transport layer having a thickness of 30 nm.

[0621] FBH as a host and Compound 1 as a dopant were co-deposited on the hole transport layer at a weight ratio of 97:3 to form an emission layer having a thickness of 20 nm.

[0622] Then, Alq 3 An electron transport layer was deposited on the emission layer to form a thickness of 30 nm, and then, LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 1 nm.

[0623] Al is vacuum deposited on the electron injection layer to form a A LiF / Al electrode (cathode) with a thickness of is formed, thereby completing the manufacture of the organic light-emitting device.

[0624]

[0625] Examples 2 to 4 and Comparative Examples 1 to 5

[0626] An organic light-emitting device was manufactured in substantially the same manner as in Example 1, except that when forming the emission layer, each of the compounds shown in Table 1 was used as a dopant.

[0627] Evaluation Example

[0628] Evaluation Example 1: Evaluation of Characteristics of Organic Light-Emitting Device

[0629] The luminance of the organic light-emitting devices manufactured in Examples 1 to 4 and Comparative Examples 1 to 5 was measured at 1,000 cd / m by using a Keithley MU 236 and a luminance meter PR650. 2 The driving voltage (V) and efficiency (Cd / A) were measured, and the results are shown in Table 1.

[0630] Table 1

[0631]

[0632]

[0633]

[0634] From Table 1, it can be seen that the organic light-emitting devices of Examples 1 to 4 have lower driving voltages and higher efficiencies than the organic light-emitting devices of Comparative Examples 1 to 5.

[0635] According to one or more embodiments, an organic light-emitting device including the heterocyclic compound represented by Formula 1 may have high efficiency and low driving voltage. In addition, high-quality electronic devices and high-quality electronic equipment may be manufactured by using the organic light-emitting device.

[0636] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for limiting purposes. The description of the features or aspects in each embodiment should generally be considered to be applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and detail may be made therein without departing from the spirit and scope defined by the appended claims and their equivalents.

Claims

1. A heterocyclic compound represented by formula 1: Formula 1 in, In formula 1, a1 and a2 are each independently 0, 1 or 2, The sum of a1 and a2 is 1 or greater, X3 and X4 are each independently O or S, Y 31 , Y 32 , Y 41 and Y 42 are each independently deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C3-C 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 10 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C3-C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryl, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10a A substituted monovalent non-aromatic fused polycyclic group, unsubstituted or replaced by at least one R 10a a substituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2), Ar1 to Ar5 are each independently C5-C 60 Carbocyclic or C1-C 60 Heterocyclic group, L6 is N(R 61 ), P(R 61 ), O, S, C(R 62 )(R 63 ), or Si(R 62 )(R 63 ), L7 is N(R 71 )、P(R 71 )、O、S、C(R 72 )(R 73 ) or Si(R 72 )(R 73 ), L8 is N(R 81 )、P(R 81 )、O、S、C(R 82 )(R 83 ) or Si(R 82 )(R 83 ), L9 is N(R 91 )、P(R 91 )、O、S、C(R 92 )(R 93 ) or Si(R 92 )(R 93 ), Z 31 To Z 33 , Z 41 To Z 43 , R1 to R5, R 61 To R 63 , R 71 To R 73 , R 81 To R 83 and R 91 To R 93 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C3-C 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 10 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C3-C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryl, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10a A substituted monovalent non-aromatic fused polycyclic group, unsubstituted or replaced by at least one R 10a a substituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2), Y 31 , Y 32 , Y 41 , Y 42 , Z 31 To Z 33 , Z 41 To Z 43 , R1 to R5, R 61 To R 63 , R 71 To R 73 , R 81 To R 83 and R 91 To R 93 Two or more adjacent groups in the group are optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C5-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, n1 to n5 are each independently an integer selected from 0 to 10, R 10a for: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; Each unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof; Each unsubstituted or substituted C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy or C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ),and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each independently represents: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 alkoxy; or each unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C substituted by alkoxy, phenyl, biphenyl or any combination thereof 60 Carbocyclic group, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl.

2. The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by Formula 1 is a compound represented by one selected from Formula 1-1 to Formula 1-3: Formula 1-1 Formula 1-2 Formula 1-3 in, In Formula 1-1 to Formula 1-3, R 31 To R 33 Each independently as described with reference to R3 in claim 1, R 41 To R 43 Each independently as described with reference to R4 in claim 1, a1 and a2 are each independently 0 or 1, and Ar1, Ar2, Ar5, R1, R2, R5, n1, n2, n5, X3, X4, L6 to L9, Y 31 , Y 32 , Y 41 , Y 42 , Z 31 To Z 33 and Z 41 To Z 43 Each as described in claim 1.

3. The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by Formula 1 is a compound represented by one selected from Formula 1-1A to Formula 1-3A: Formula 1-1A Formula 1-2A Formula 1-3A in, In Formula 1-1A to Formula 1-3A, R 11 To R 14 Each independently as described with reference to R1 in claim 1, R 21 To R 24 Each independently as described with reference to R2 in claim 1, R 31 To R 33 Each independently as described with reference to R3 in claim 1, R 41 To R 43 Each independently as described with reference to R4 in claim 1, R 51 and R 52 Each independently as described with reference to R5 in claim 1, a1 and a2 are each independently 0 or 1, and X3, X4, L6 to L9, Y 31 , Y 32 , Y 41 , Y 42 , Z 31 To Z 33 and Z 41 To Z 43 Each as described in claim 1.

4. The heterocyclic compound according to claim 1, wherein R 61 To R 63 , R 71 To R 73 , R 81 To R 83 and R 91 To R 93 are each independently unsubstituted or substituted with at least one R 10a substituted phenyl, and R 10a As described in claim 1.

5. The heterocyclic compound according to claim 1, wherein R 61 To R 63 , R 71 To R 73 , R 81 To R 83 and R 91 To R 93 Each is independently a group represented by one selected from Formula 2-1 to Formula 2-17: in, In Formula 2-1 to Formula 2-17, Z 11 To Z 15 Each independently as in claim 1 10a described, and *Indicates the binding site with the neighboring atoms.

6. The heterocyclic compound according to claim 1, wherein Y 31 , Y 32 , Y 41 and Y 42 are each independently unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkyl, and R 10a As described in claim 1.

7. The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by Formula 1 is selected from Compound 1 to Compound 12, Compound 14 to Compound 16, and Compound 18 to Compound 27:

8. An organic light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; as well as an interlayer between the first electrode and the second electrode and including an emission layer, The organic light-emitting device further comprises at least one heterocyclic compound according to any one of claims 1 to 7. 9 . An electronic device comprising the organic light emitting device according to claim 8 .

10. An electronic device comprising the organic light-emitting device according to claim 8.

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