Light-emitting device including heterocyclic compound, electronic device including light-emitting device, electronic device including light-emitting device, and heterocyclic compound

Abstract

Light-emitting device including heterocyclic compound represented by Formula 1, electronic device including light-emitting device, electronic device including light-emitting device, and heterocyclic compound represented by Formula 1: Formula 1

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2024-0049403, filed on April 12, 2024, in the Korean Intellectual Property Office, the disclosure of which is incorporated herein by reference in its entirety. Technical Field

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

[0004] Among light-emitting devices, self-emitting devices (e.g., light-emitting devices) have relatively wide viewing angles, high contrast ratios, short response times, and excellent or appropriate characteristics in terms of brightness, driving voltage, and response speed. That is, self-emitting devices (e.g., light-emitting devices) stand out among light-emitting devices due to their wide viewing angles, high contrast ratios, fast response times, and excellent characteristics in terms of brightness, driving voltage, and response speed.

[0005] In a light-emitting device, a first electrode is arranged on a substrate, and a hole transport region, an emissive layer, an electron transport region, and a second electrode are arranged in sequence on the first electrode. Holes provided from the first electrode move toward the emissive layer through the hole transport region, and electrons provided from the second electrode move toward the emissive layer through the electron transport region. Carriers (such as holes and electrons) recombine in the emissive layer to generate excitons. The excitons transition from an excited state and decay to a ground state, thereby generating light (for example, for displaying an image). Summary of the Invention

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

[0007] Additional aspects 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 of the present disclosure, a light emitting device includes:

[0009] a first electrode;

[0010] a second electrode opposite to the first electrode (eg, facing the first electrode);

[0011] an interlayer between the first electrode and the second electrode and including an emissive layer, and

[0012] Heterocyclic compound represented by Formula 1:

[0013] Formula 1

[0014]

[0015] Formula 2C

[0016]

[0017] Wherein, in Formula 1, Formula 2A, Formula 2B and Formula 2C,

[0018] X1 can be C(R 11 ) or N, X2 can be C(R 12 ) or N, and X3 may be C(R 13 ) or N,

[0019] Z1 may be a group represented by any one selected from Formula 2A, Formula 2B, and Formula 2C (for example, one selected therefrom),

[0020] Y1 may be unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Alkylene, unsubstituted or substituted with at least one R 10a Substituted C3-C 30 Cycloalkylene is either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocycloalkylene, wherein Y1 may not include (eg, may exclude) any unsubstituted or replaced by at least one R 10a substituted adamantyl groups,

[0021] Ar1 to Ar3 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by 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 C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by at least one R 10aSubstituted 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 C7-C 60 Aralkyl, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2),

[0022] L1 to L4 may each independently be unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 heterocyclic group,

[0023] n1 to n4 may each independently be an integer selected from 0 to 4, wherein if (for example, when) n1 is 0, then *-(L1) n1 -*' may be a single bond, if (for example, when) n2 is 0, then *-(L2) n2 -*' may be a single bond, if (for example, when) n3 is 0, then *-(L3) n3 -*' may be a single bond, and if (for example, when) n4 is 0, then *-(L4) n4 -*' can be a single key,

[0024] R1 and R2 can each independently be deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by 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 C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by at least one R 10aSubstituted 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 C7-C 60 Aralkyl, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2),

[0025] a4 and b4 may each independently be an integer selected from 0 to 4, and a6 and b6 may each independently be an integer selected from 0 to 6,

[0026] If (for example, when) Z1 is a group represented by Formula 2A, then the sum of a4 and b4 may be 1 or greater,

[0027] If (for example, when) a4 is 2 or greater or if (for example, when) a6 is 2 or greater, two or more R1 may be optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 30 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 heterocyclic group,

[0028] If (for example, when) b4 is 2 or greater or if (for example, when) b6 is 2 or greater, two or more R2 may be optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 30 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 heterocyclic group,

[0029] R1 and R2 may each independently optionally be bonded to L3, L4 or Ar3 to form an unsubstituted or substituted group. 10a Substituted C3-C 30 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 heterocyclic group,

[0030] R 11 to R 13 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by at least one R 10a Substituted C1-C 60Alkyl, 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 C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by at least one R 10a Substituted C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 arylthio, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2),

[0031] R 10a Can be:

[0032] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, or nitro;

[0033] Each unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy or C1-C 60 Alkylthio: 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, 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)(Q11 )、-S(=O)2(Q 11 ),-P(=O)(Q 11 )(Q 12 ) or any combination thereof;

[0034] Each unsubstituted or substituted C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroarylalkyl: 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

[0035] -O(Q 31 )、-S(Q 31 )、-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 ),

[0036] Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each of them can be independently: 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; C1-C 60 Alkylthio; each unsubstituted or deuterated, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, C1-C 60 C3-C substituted by alkylthio, phenyl, biphenyl or any combination thereof 60 Carbocyclic or C1-C 60 Heterocyclic group; C7-C 60 Aralkyl; or C2-C 60 heteroarylalkyl, and

[0037] * and *' each indicate a bonding site to an adjacent atom.

[0038] According to one or more embodiments of the present disclosure, an electronic device includes the light emitting device of one or more embodiments of the present disclosure.

[0039] According to one or more embodiments of the present disclosure, electronic equipment includes the light emitting device according to one or more embodiments of the present disclosure.

[0040] According to one or more embodiments of the present disclosure, a heterocyclic compound represented by Formula 1 is provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0041] The accompanying drawings are included to provide a further understanding of the present disclosure and are incorporated into and constitute a part of this disclosure. The accompanying drawings illustrate embodiments of the present disclosure and, together with the description, serve to explain the principles of the present disclosure. The above and other aspects, features, and advantages of certain embodiments of the present disclosure will become more apparent from the following description taken in conjunction with the accompanying drawings, in which:

[0042] Figure 1 is a schematic cross-sectional view of the structure of a light emitting device according to one or more embodiments of the present disclosure;

[0043] Figure 2 is a schematic cross-sectional view of a structure of a light emitting device according to one or more embodiments of the present disclosure;

[0044] Figure 3is a schematic cross-sectional view of a structure of a light emitting device according to one or more embodiments of the present disclosure;

[0045] Figure 4 is a block diagram of an electronic device according to one embodiment;

[0046] Figure 5 is a schematic diagram of an electronic device according to one or more embodiments;

[0047] Figure 6 is a schematic perspective view of an electronic device including a light emitting device according to one or more embodiments of the present disclosure;

[0048] Figure 7 is a schematic diagram of the exterior of a vehicle as an electronic device including a light emitting device according to one or more embodiments of the present disclosure; and

[0049] Figures 8A to 8C Each is a schematic diagram of the interior of a vehicle as an electronic equipment including a light emitting device according to one or more embodiments of the present disclosure. DETAILED DESCRIPTION

[0050] The embodiments of the present invention will now be described in more detail with reference to their examples in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout the present disclosure, and for the sake of brevity, their repeated description may not be provided. In this regard, the present embodiments may have different forms and should not be interpreted as being limited to the description set forth herein. Accordingly, the embodiments of the present invention are described only with reference to the accompanying drawings to explain aspects of the present invention. As used herein, the terms "and / or" or "or" may include any and all combinations of one or more related enumerated items. Throughout the present disclosure, when expressions such as "at least one of...", "one of...", and "selected from" are before / after a list of elements, they modify the entire list of elements without modifying the individual elements of the list. For example, "at least one of a, b, and c," "selected from at least one of a, b, and c," "selected from at least one of a to c," etc. may indicate only a, only b, only c, (e.g., simultaneously) both a and b, (e.g., simultaneously) both a and c, (e.g., simultaneously) both b and c, all a, b, and c, or variations thereof. As used herein, “ / ” may be interpreted as “and” or “or” depending on the circumstances.

[0051] According to one or more embodiments of the present disclosure, the heterocyclic compound is represented by Formula 1:

[0052] Formula 1

[0053]

[0054] Wherein, in Formula 1, X1 can be C(R 11) or N, X2 can be C(R 12 ) or N, and X3 may be C(R 13 ) or N.

[0055] In one or more embodiments, at least one selected from X1 to X3 may be N.

[0056] In one or more embodiments, at least two selected from X1 to X3 may each be N.

[0057] In one or more embodiments, X1 to X3 may each be N.

[0058] In Formula 1, Z1 may be a group represented by any one selected from Formula 2A, Formula 2B, and Formula 2C:

[0059]

[0060] Formula 2C

[0061]

[0062] Wherein, in Formula 2A, Formula 2B and Formula 2C, Y1 may be unsubstituted or replaced by at least one R 10a Substituted C1-C 30 Alkylene, unsubstituted or substituted with at least one R 10a Substituted C3-C 30 Cycloalkylene is either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocycloalkylene, wherein Y1 may not include (eg, may exclude) any unsubstituted or replaced by at least one R 10a Substituted adamantyl.

[0063] For example, Y1 may not include (eg, may exclude) any unsubstituted or replaced by at least one R 10a Replaced Represents the group.

[0064] In one or more embodiments, Y1 may be unsubstituted or replaced by at least one R 10a Substituted C1-C 10 Alkylene, unsubstituted or substituted with at least one R 10a Substituted C3-C9 cycloalkylene or unsubstituted or replaced by at least one R 10a Substituted C1-C9 heterocycloalkylene.

[0065] In one or more embodiments, Y1 may be unsubstituted or replaced by at least one R 10a Substituted C1-C 10The alkylene group may alternatively be a group represented by any one selected from Formula 3-1 to Formula 3-15:

[0066]

[0067]

[0068] Among them, in formula 3-1 to formula 3-15,

[0069] R 10a Same as described in this article,

[0070] c6 may be an integer selected from 0 to 6,

[0071] c10 may be an integer selected from 0 to 10, and

[0072] * and *' each indicate a bonding site to an adjacent atom.

[0073] In Formula 1, Ar1 to Ar3 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by 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 C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by 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 C7-C 60 Aralkyl, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2), and

[0074] R10a and Q1 to Q3 are each the same as described herein.

[0075] In one or more embodiments, Ar1 to Ar3 may each independently be:

[0076] Each unsubstituted or substituted phenyl, biphenyl, (C1-C 10 alkyl) phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrene, 1,2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, phthalazinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, phenyl isothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl or azadibenzothiorol: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl) phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolyl quinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phthalazinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 ),-P(=O)(Q31 )(Q 32 ) or any combination thereof; or

[0077] -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), or -P(=O)(Q1)(Q2), and

[0078] Q1 to Q3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 Alkoxy; C1-C 60 Alkylthio; each unsubstituted or deuterated, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, C1-C 60 C3-C substituted by alkylthio, phenyl, biphenyl or any combination thereof 60 Carbocyclic or C1-C 60 Heterocyclic group; C7-C 60 Aralkyl; or C2-C 60 Heteroaralkyl.

[0079] In one or more embodiments, Ar1 to Ar3 may each independently be a group represented by any one selected from Formula 4-1 to Formula 4-6:

[0080]

[0081] Among them, in formula 4-1 to formula 4-6,

[0082] R 10a Same as described in this article,

[0083] d4 may be an integer selected from 0 to 4,

[0084] d5 may be an integer selected from 0 to 5,

[0085] d7 may be an integer selected from 0 to 7, and

[0086] *Indicates the bonding site to the adjacent atom.

[0087] In one or more embodiments, at least one selected from Ar1 to Ar3 may be replaced by -F, cyano, -P(=O)(Q1)(Q2), or any combination thereof.

[0088] In one or more embodiments, Ar3 may not include (eg, may exclude) any triazine groups.

[0089] In Formula 1, L1 to L4 may each independently be unsubstituted or replaced by at least one R 10a Substituted C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group.

[0090] In one or more embodiments, L1 to L4 may each independently be:

[0091] Each is unsubstituted or substituted with at least one R 10a Substituted phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, cyclopentadienyl, furanyl, thienyl, thiaryl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzothiaryl, dibenzothiaryl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothiaryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phthalazinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl oxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, dibenzooxasilanyl, dibenzothiasilanyl, dibenzodihydroazasilanyl, dibenzodihydrodisilazane, dibenzodihydrosilanyl, dibenzodioxane, dibenzooxathiasilanyl, dibenzoxazinyl, dibenzopyranyl, dibenzodithiazinyl, dibenzothiopyranyl, dibenzocyclohexadienyl, dibenzodihydropyridinyl or dibenzodihydropyrazinyl.

[0092] In one or more embodiments, L4 may not include (eg, may exclude) any triazine groups.

[0093] In Formula 1, n1 to n4 may each independently be an integer selected from 0 to 4, wherein if (for example, when) n1 is 0, then *-(L1) n1 -*' may be a single bond, if (for example, when) n2 is 0, then *-(L2) n2 -*' may be a single bond, if (for example, when) n3 is 0, then *-(L3) n3 -*' may be a single bond, and if (for example, when) n4 is 0, then *-(L4) n4 -*' can be a single bond.

[0094] In Formula 2A, Formula 2B and Formula 2C, R1 and R2 can each independently be deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by 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 C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by 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 C7-C 60 Aralkyl, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2).

[0095] In one or more embodiments, in Formula 2A, Formula 2B, and Formula 2C, R1 and R2 may each independently be:

[0096] Deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy or C1-C 20 alkylthio;

[0097] C1-C 20 Alkyl, C1-C 20 Alkoxy or C1-C 20 Alkylthio: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 10alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof;

[0098] each unsubstituted or substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, phthalazinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl , benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, phthalazinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 ),-P(=O)(Q 31 )(Q 32 ) or any combination thereof; or

[0099] -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), or -P(=O)(Q1)(Q2), and

[0100] Q1 to Q3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; cyano; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 Alkoxy; C1-C 60 Alkylthio; each unsubstituted or deuterated, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, C1-C 60 C3-C substituted by alkylthio, phenyl, biphenyl or any combination thereof 60 Carbocyclic or C1-C 60 Heterocyclic group; C7-C 60 Aralkyl; or C2-C 60 Heteroaralkyl.

[0101] In one or more embodiments, in Formula 2A, Formula 2B, and Formula 2C, a4 and b4 may each independently be an integer selected from 0 to 4, and a6 and b6 may each independently be an integer selected from 0 to 6, wherein, if (for example, when) Z1 is a group represented by Formula 2A, the sum of a4 and b4 may be 1 or greater.

[0102] In Formula 2A, Formula 2B, and Formula 2C, if (for example, when) a4 is 2 or greater or if (for example, when) a6 is 2 or greater, two or more R1 may be optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C3-C 30 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic group.

[0103] In Formula 2A, Formula 2B, and Formula 2C, if (for example, when) b4 is 2 or greater (when) or if (for example, when) b6 is 2 or greater (when), two or more R2 may be optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 30 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic group.

[0104] In Formula 1, Formula 2A, Formula 2B and Formula 2C, R1 and R2 may each independently optionally bond to L3, L4 or Ar3 to form an unsubstituted or substituted group. 10a Substituted C3-C 30 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic group.

[0105] In formula 1, R 11 to R 13 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by 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 C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by at least one R 10a Substituted C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2).

[0106] In one or more embodiments, in Formula 1, R 11 to R 13 Can be independently:

[0107] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy or C1-C 20 alkylthio;

[0108] C1-C 20Alkyl, C1-C 20 Alkoxy or C1-C 20 Alkylthio: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof;

[0109] each unsubstituted or substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, phthalazinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl , benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, phthalazinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33)、-N(Q 31 )(Q 32 ),-P(=O)(Q 31 )(Q 32 ) or any combination thereof; or

[0110] -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), or -P(=O)(Q1)(Q2), and

[0111] Q1 to Q3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; cyano; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 Alkoxy; C1-C 60 Alkylthio; each unsubstituted or deuterated, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, C1-C 60 C3-C substituted by alkylthio, phenyl, biphenyl or any combination thereof 60 Carbocyclic or C1-C 60 Heterocyclic group; C7-C 60 Aralkyl; or C2-C 60 Heteroaralkyl.

[0112] In one or more embodiments, in Formula 1, *-(L3) n3 -Z1-(L4) n4 The group represented by -* may be a group represented by any one selected from Formula 5-1 to Formula 5-10:

[0113]

[0114]

[0115] Among them, in formula 5-1 to formula 5-10,

[0116] T1 can be O, S, N (R 10b ) or C(R 10b )(R 10c ),

[0117] e6 may be an integer selected from 0 to 6,

[0118] e8 may be an integer selected from 0 to 8,

[0119] e10 may be an integer selected from 0 to 10,

[0120] R 10b and R 10c Each independently and with reference R 10a Same as described,

[0121] Y1, R1, R2, a4, b4, a6, b6, and R 10a each being the same as described herein, and

[0122] *Indicates the bonding site to the adjacent atom.

[0123] In one or more embodiments, the heterocyclic compound represented by Formula 1 may have an asymmetric structure.

[0124] Unless otherwise specified, R 10a Can be:

[0125] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, or nitro;

[0126] Each unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy or C1-C 60 Alkylthio: 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, 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;

[0127] Each unsubstituted or substituted C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C60 Heteroarylalkyl: 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

[0128] -O(Q 31 )、-S(Q 31 )、-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 ).

[0129] Unless otherwise specified, Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each of them can be independently: 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; C1-C 60Alkylthio; each unsubstituted or deuterated, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, C1-C 60 C3-C substituted by alkylthio, phenyl, biphenyl or any combination thereof 60 Carbocyclic or C1-C 60 Heterocyclic group; C7-C 60 Aralkyl; or C2-C 60 Heteroaralkyl.

[0130] In Formula 1, Formula 2A, Formula 2B, and Formula 2C, R1 and R2 may each independently be:

[0131] Deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy or C1-C 20 alkylthio;

[0132] C1-C 20 Alkyl, C1-C 20 Alkoxy or C1-C 20 Alkylthio: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof;

[0133] each unsubstituted or substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, phthalazinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl , benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 20 Alkyl, C1-C20 Alkoxy, C1-C 20 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, phthalazinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 ),-P(=O)(Q 31 )(Q 32 ) or any combination thereof; or

[0134] -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), or -P(=O)(Q1)(Q2), and

[0135] Q1 to Q3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; cyano; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 Alkoxy; C1-C 60 Alkylthio; each unsubstituted or deuterated, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, C1-C 60 C3-C substituted by alkylthio, phenyl, biphenyl or any combination thereof 60 Carbocyclic or C1-C 60 Heterocyclic group; C7-C 60 Aralkyl; or C2-C 60 Heteroaralkyl.

[0136] In one or more embodiments, the heterocyclic compound represented by Formula 1 may be any one selected from Compound 1 to Compound 1092:

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228] The heterocyclic compound represented by Formula 1 may have a structure including a triazine group or a pyrimidine group, thereby having high intermolecular interaction due to increased π-π interaction. As a result, the heterocyclic compound represented by Formula 1 may have high electron transport capability.

[0229] In addition, in the heterocyclic compound represented by Formula 1, sp can be introduced to inhibit or reduce the π-π interaction. 3 Carbon can increase the intermolecular distance, thereby controlling or selecting the electron mobility and refractive index, and can be 3 The lowest unoccupied molecular orbital (LUMO) energy level of the heterocyclic compound is variously changed by adjusting the position of carbon. As a result, a suitable or appropriate energy level can be obtained between the electron transport layer and the emission layer, so that the exciton generation efficiency in the emission layer can be increased.

[0230] In addition, the heterocyclic compound represented by Formula 1 may not include (eg, may exclude) any adamantyl group in Y1, thereby having high electron transport capability and thermal rigidity compared to a compound including an adamantyl group.

[0231] In addition, in the heterocyclic compound represented by Formula 1, if (for example, when) Z1 is a group represented by Formula 2A, the sum of a4 and b4 may be 1 or greater, and therefore, compared with the compound in which Z1 is a group represented by Formula 2A and the sum of a4 and b4 is 0, the electron transport ability can be controlled or selected by adjusting the substituents of R1 and / or R2, so that the charge balance can be effectively improved.

[0232] Accordingly, if (eg, when) the heterocyclic compound represented by Formula 1 is applied to a light-emitting device (eg, applied to an electron transport region of a light-emitting device), high light emission efficiency and long device life can be achieved.

[0233] By referring to the synthesis examples and / or embodiments provided herein, one of ordinary skill in the art can recognize methods for synthesizing the heterocyclic compound represented by Formula 1.

[0234] According to one or more embodiments of the present disclosure, at least one heterocyclic compound represented by Formula 1 can be used in a light-emitting device (e.g., an organic light-emitting device). Accordingly, a light-emitting device is provided, comprising: a first electrode; a second electrode opposite to (e.g., facing) the first electrode; an interlayer between the first electrode and the second electrode and including an emissive layer; and a heterocyclic compound represented by Formula 1.

[0235] In one or more embodiments,

[0236] The first electrode of the light emitting device may be an anode,

[0237] The second electrode of the light emitting device may be a cathode,

[0238] The interlayer may further include a hole transport region between the first electrode and the emissive layer and an electron transport region between the emissive layer and the second electrode,

[0239] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof, and

[0240] 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.

[0241] In one or more embodiments, the heterocyclic compound represented by Formula 1 may be included between the first and second electrodes of the light emitting device. Accordingly, the heterocyclic compound represented by Formula 1 may be included in the interlayer of the light emitting device, for example, in the electron transport region of the interlayer.

[0242] In one or more embodiments, the electron transport layer may include the heterocyclic compound represented by Formula 1.

[0243] In one or more embodiments, the emissive layer in the interlayer of the light-emitting device may include a dopant and a host. The emissive layer may emit red light, green light, blue light, and / or white light (e.g., combined white light). For example, in one or more embodiments, the emissive layer may emit blue light. The blue light may have a maximum emission wavelength (e.g., a wavelength of a maximum emission peak) in the range of, for example, about 400 nanometers (nm) to about 490 nm.

[0244] In one or more embodiments, the blue light may have a maximum emission wavelength in the range of about 430 nm to about 480 nm, about 430 nm to about 475 nm, about 440 nm to about 475 nm, about 450 nm to about 475 nm, about 430 nm to about 470 nm, about 440 nm to about 470 nm, about 450 nm to about 470 nm, about 430 nm to about 465 nm, about 440 nm to about 465 nm, about 450 nm to about 465 nm, about 430 nm to about 460 nm, about 440 nm to about 460 nm, or about 450 nm to about 460 nm.

[0245] In one or more embodiments, the host may include a heterocyclic compound represented by Formula 1. For example, in one or more embodiments, the heterocyclic compound represented by Formula 1 may serve as the host.

[0246] In one or more embodiments, the emission layer in the interlayer of the light-emitting device may include a dopant and a host, the dopant may include a transition metal compound, the transition metal compound may include a transition metal and m ligands, m may be an integer selected from 1 to 6, the m ligands may be the same as or different from each other, at least one of the m ligands and the transition metal may be connected to each other via a carbon-transition metal bond, and the carbon-transition metal bond may be a coordination bond. For example, in one or more embodiments, at least one of the m ligands (e.g., selected from) may be a carbene ligand (e.g., a carbene ligand in Ir(pmp)3, etc.). The transition metal may be, for example, iridium, platinum, osmium, palladium, rhodium and / or gold, etc. The dopant may emit blue light. More details about the emission layer and the dopant may be independently the same as described herein.

[0247]

[0248] In one or more embodiments, the emission layer in the interlayer of the light emitting device may include a dopant and a host, and the host may include a nitrogen-containing C1-C 60 The second compound of the heterocyclic group and the third compound including the group represented by Formula 32 described herein and the dopant may emit blue light. The second compound and the third compound in the light-emitting device may be different from each other.

[0249] In one or more embodiments, the second compound and the third compound can form an exciplex.

[0250] In one or more embodiments, the second compound may include a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, or any combination thereof.

[0251] In one or more embodiments, the second compound may include a compound represented by Formula 31:

[0252] Formula 31

[0253]

[0254] Wherein, in formula 31,

[0255] L 51 To L 53 Each independently may be a single bond, unsubstituted or substituted by at least one R 10a Substituted C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 heterocyclic group,

[0256] b51 to b53 may each independently be an integer selected from 1 to 5,

[0257] X 54 Can be N or C(R 54 ), X 55 Can be N or C(R 55 ), X 56 Can be N or C(R 56 ), and selected from X 54 To X 56 At least one of may be N, and

[0258] R 51 to R 56 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by at least one R 10a Substituted C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60Alkenyl, 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 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by 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 C7-C 60 Aralkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 heteroarylalkyl, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1), or -P(═O)(Q1)(Q2).

[0259] R 10a and Q1 to Q3 are each the same as described herein.

[0260] Formula 32

[0261]

[0262] In Equation 32,

[0263] CycloCY 71 and CY 72 Can be independently π-electron-rich C3-C 60 a cyclic group or a pyridyl group,

[0264] X 71 can be a single bond, or a linking group comprising O, S, N, B, C, Si, or any combination thereof, and

[0265] * indicates a bonding site to any atom contained in the remaining portion other than the group represented by Formula 32 in the third compound.

[0266] In one or more embodiments, the third compound may not include (eg, may exclude) the compound represented by Formula 3A described herein.

[0267] In one or more embodiments, the following compounds may be excluded from the third compound:

[0268]

[0269] In one or more embodiments, the third compound may include a compound represented by Formula 3A, a compound represented by Formula 3B, a compound represented by Formula 3C, a compound represented by Formula 3D, a compound represented by Formula 3E, or any combination thereof:

[0270]

[0271]

[0272] Wherein, in Formula 3A to Formula 3E,

[0273] CycloCY 71 To Ring CY 74 Can be independently π-electron-rich C3-C 60 a cyclic group or a pyridyl group,

[0274] X 82 Can be single bond, O, S, N[(L 82 ) b82 -R 82 ]、B[(L 82 ) b82 -R 82 ]、C(R 82a )(R 82b ) or Si(R 82a )(R 82b ),

[0275] X 83 Can be single bond, O, S, N[(L 83 ) b83 -R 83 ]、B[(L 83 ) b83 -R 83 ]、C(R 83a )(R 83b ) or Si(R 83a )(R 83b ),

[0276] X 84 Can be O, S, N[(L 84 ) b84 -R 84 ]、B[(L 84 ) b84 -R 84 ]、C(R 84a )(R 84b ) or Si(R84a )(R 84b ),

[0277] X 85 Can be C or Si,

[0278] L 81 To L 85 Each of them can be independently a single bond, *-C(Q4)(Q5)-*', *-Si(Q4)(Q5)-*', unsubstituted or replaced by at least one R 10a Substituted π-electron-rich C3-C 60 The cyclic group is either unsubstituted or substituted with at least one R 10a Substituted pyridyl, wherein Q4 and Q5 are each independently the same as described with reference to Q1,

[0279] b81 to b85 may each independently be an integer selected from 1 to 5,

[0280] R 71 to R 74 、R 81 to R 85 、R 82a 、R 82b 、R 83a 、R 83b 、R 84a and R 84b can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by 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 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by 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 C7-C 60 Aralkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C60 heteroarylalkyl, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1), or -P(═O)(Q1)(Q2),

[0281] a71 to a74 may each independently be an integer selected from 0 to 20, and

[0282] R 10a and Q1 to Q3 are each the same as described herein.

[0283] In one or more embodiments, the emission layer in the interlayer of the light-emitting device may include a dopant and a host, and the dopant may include a transition metal compound, a delayed fluorescent material, or any combination thereof. The delayed fluorescent material may be a compound in which the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material is at least 0 eV but not more than about 0.5 eV (or at least 0 eV but not more than about 0.3 eV).

[0284] In one or more embodiments, the delayed fluorescent material may be a compound including at least one cyclic group including (eg, simultaneously including) both boron (B) and nitrogen (N) as ring-constituting atoms.

[0285] In one or more embodiments, the delayed fluorescent material may be a C8-C 60 Compounds with polycyclic groups, containing C8-C 60 The compound of the polycyclic group includes two or more cyclic groups fused to each other while sharing boron (B). In other words, the delayed fluorescent material may be C8-C 60 In one or more embodiments, the C8-C 60 Polycyclic compounds include two or more cyclic groups fused together and sharing a boron (B) atom.

[0286] In one or more embodiments, the delayed fluorescent material may include a fused ring in which at least one third ring is fused with at least one fourth ring, for example, to form a fused ring including four or more rings.

[0287] The third ring of the delayed fluorescent material may be cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, adamantyl, norbornenyl, norbornyl, bicyclo[1.1.1]pentanyl, bicyclo[2.1.1]hexanyl, bicyclo[2.2.2]octyl, phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl, and

[0288] The fourth ring of the delayed fluorescent material may be 1,2-azaborinyl, 1,3-azaborinyl, 1,4-azaborinyl, 1,2-dihydro-1,2-azaborinyl, 1,4-oxaborinyl, 1,4-thiaborinyl or 1,4-dihydroborinyl. In other words, the delayed fluorescent material described in one or more embodiments may be characterized by a fused ring structure in which at least one third ring is combined with at least one fourth ring to form a structure having four or more rings. The third ring may be selected from various groups such as cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, adamantyl, norbornenyl, norbornyl, bicyclo[1.1.1]pentanyl, bicyclo[2.1.1]hexanyl, bicyclo[2.2.2]octyl, phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl. The fourth ring can be any one of (eg, selected from) 1,2-azaboraphenyl, 1,3-azaboraphenyl, 1,4-azaboraphenyl, 1,2-dihydro-1,2-azaboraphenyl, 1,4-oxaboraphenyl, 1,4-thiaboraphenyl, and 1,4-dihydroboraphenyl.

[0289] In one or more embodiments, the delayed fluorescent material may include a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof:

[0290]

[0291] Among them, in formula 502 and formula 503,

[0292] Ring A 501 To Ring A 504 Can be independently C3-C 60 Carbocyclic or C1-C 60 heterocyclic group,

[0293] Y 505 Can be O, S, N (R 505 )、B(R 505 )、C(R 505a )(R 505b ) or Si(R 505a )(R 505b ),

[0294] Y 506 Can be O, S, N (R 506 )、B(R 506 )、C(R 506a )(R 506b ) or Si(R 506a )(R 506b ),

[0295] Y507 Can be O, S, N (R 507 )、B(R 507 )、C(R 507a )(R 507b ) or Si(R 507a )(R 507b ),

[0296] Y 508 Can be O, S, N (R 508 )、B(R 508 )、C(R 508a )(R 508b ) or Si(R 508a )(R 508b ),

[0297] Y 51 and Y 52 may be each independently B, P(=O) or S(=O),

[0298] R 500a 、R 500b 、R 501 to R 508 、R 505a 、R 505b 、R 506a 、R 506b 、R 507a 、R 507b 、R 508a and R 508b can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by 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 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by 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 C7-C60 Aralkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 heteroarylalkyl, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2), and

[0299] a501 to a504 may each independently be an integer selected from 0 to 20.

[0300] R 10a and Q1 to Q3 are each the same as described herein.

[0301] In one or more embodiments, the light emitting device may satisfy at least one selected from Conditions 1 to 4:

[0302] Condition 1

[0303] The lowest unoccupied molecular orbital (LUMO) energy level (eV) of the third compound is greater than the LUMO energy level (eV) of the transition metal compound.

[0304] Condition 2

[0305] LUMO energy level (eV) of the transition metal compound > LUMO energy level (eV) of the second compound

[0306] Condition 3

[0307] The highest occupied molecular orbital (HOMO) energy level (eV) of the transition metal compound is greater than the HOMO energy level (eV) of the third compound.

[0308] Condition 4

[0309] The HOMO energy level (eV) of the third compound is greater than the HOMO energy level (eV) of the second compound.

[0310] In the present disclosure, each of the HOMO energy level and the LUMO energy level of each of the transition metal-containing compound, the second compound, and the third compound may be a negative value and may be measured according to an appropriate method.

[0311] In one or more embodiments, the absolute value of the difference between the LUMO energy level of the transition metal-containing compound and the LUMO energy level of the second compound may be at least about 0.1 eV but at most, for example, not greater than about 1.0 eV, the absolute value of the difference between the LUMO energy level of the transition metal-containing compound and the LUMO energy level of the third compound may be at least about 0.1 eV but at most, for example, not greater than about 1.0 eV, the absolute value of the difference between the HOMO energy level of the transition metal-containing compound and the HOMO energy level of the second compound may be about 1.25 eV or less (e.g., at least about 0.2 eV but at most, for example, not greater than about 1.25 eV), and the absolute value of the difference between the HOMO energy level of the transition metal-containing compound and the HOMO energy level of the third compound may be about 1.25 eV or less (e.g., at least about 0.2 eV but at most, for example, not greater than about 1.25 eV).

[0312] When the relationship between the LUMO energy level and the HOMO energy level satisfies the conditions described above, a balance between holes and electrons injected into the emission layer can be achieved.

[0313] In one or more embodiments, the electron transport region of the light emitting device may include a hole blocking layer, and the hole blocking layer may include a phosphine oxide-containing compound, a silicon-containing compound, or any combination thereof. For example, the hole blocking layer may directly contact the emission layer.

[0314] In one or more embodiments, the light emitting device may include a capping layer disposed outside the first electrode (eg, disposed on the first electrode) and / or a capping layer disposed outside the second electrode (eg, disposed on the second electrode).

[0315] In one or more embodiments, the light-emitting device may further include at least one of a first capping layer on the surface of the first electrode (e.g., arranged on the surface of the first electrode) and a second capping layer on the surface of the second electrode (e.g., arranged on the surface of the second electrode), and at least one of the first capping layer and the second capping layer may include the heterocyclic compound represented by Formula 1. More details about the first capping layer and / or the second capping layer may be the same as those described herein.

[0316] In one or more embodiments, a light emitting device may include:

[0317] a first capping layer on a surface of the first electrode (e.g., disposed on a surface of the first electrode) and including a heterocyclic compound represented by Formula 1;

[0318] a second capping layer on a surface of the second electrode (eg, disposed on a surface of the second electrode) and including the heterocyclic compound represented by Formula 1; or

[0319] a first capping layer and a second capping layer.

[0320] As used herein, the expression "(the interlayer and / or the capping layer) includes at least one heterocyclic compound represented by Formula 1" may include embodiments in which "(the interlayer and / or the capping layer) includes the same heterocyclic compound represented by Formula 1" and embodiments in which "(the interlayer and / or the capping layer) includes two or more different heterocyclic compounds each represented by Formula 1".

[0321] In one or more embodiments, the interlayer and / or the capping layer may include only Compound 1 as the heterocyclic compound represented by Formula 1. In this regard, Compound 1 may be present in the electron transport region of the light-emitting device. In one or more embodiments, the interlayer may include Compound 1 and Compound 2 as heterocyclic compounds represented by Formula 1. In this regard, Compound 1 and Compound 2 may be present in the same layer (for example, Compound 1 and Compound 2 may both be (for example, simultaneously) present in the electron transport region), or may be present in layers of different layers (for example, Compound 1 may be present in the electron transport region, and Compound 2 may be present in the hole transport region).

[0322] The term "interlayer" as used herein refers to a single layer and / or multiple layers disposed between a first electrode and a second electrode of a light-emitting device.

[0323] According to one or more embodiments of the present disclosure, an electronic device may include a light-emitting device. The electronic device may further include a thin film transistor. For example, in one or more embodiments, the electronic device may further include a thin film transistor, the thin film transistor including a source electrode and a drain electrode, and the first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode. In one or more embodiments, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof. More details about the electronic device may be the same as described herein.

[0324] According to one or more embodiments of the present disclosure, the electronic equipment may include a light-emitting device. For example, the electronic equipment may 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 computer, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays spliced ​​together, a theater screen, a stadium screen, a light therapy device, and at least one of a sign. More details about the electronic equipment may be the same as described herein.

[0325] Figure 1 Description

[0326] Figure 1 1 is a schematic cross-sectional view of a structure of a light emitting device 10 according to one or more embodiments. The light emitting device 10 may include a first electrode 110 , an interlayer 130 , and a second electrode 150 .

[0327] Below, we will refer to Figure 1 The structure of the light emitting device 10 and a method of manufacturing the light emitting device 10 according to one or more embodiments are described.

[0328] First electrode 110

[0329] exist Figure 1 In one or more embodiments, a substrate may be additionally provided and arranged below the first electrode 110 and / or on the second electrode 150. A glass substrate or a plastic substrate may be used as the substrate. In one or more embodiments, the substrate may be a flexible substrate and may include a plastic having excellent or appropriate heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.

[0330] The first electrode 110 may be formed on a substrate by, for example, depositing or sputtering a material for forming the first electrode 110. 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 hole injection.

[0331] The first electrode 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. In one or more embodiments, if (for example, when) the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In one or more embodiments, if (for example, when) the first electrode 110 is a transflective 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.

[0332] The first electrode 110 may have a single-layer structure including a single layer (eg, consisting of a single layer) or a multi-layer structure including a plurality of layers. For example, in some embodiments, the first electrode 110 may have a triple-layer structure of ITO / Ag / ITO.

[0333] Interlayer 130

[0334] The interlayer 130 may be disposed on the first electrode 110. The interlayer 130 may include an emission layer.

[0335] In one or more embodiments, 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 .

[0336] In one or more embodiments, the interlayer 130 may further include, for example, a heterocyclic compound represented by Formula 1, a metal-containing compound (such as an organometallic compound), and / or an inorganic material (such as quantum dots), in addition to one or more appropriate organic materials.

[0337] In one or more embodiments, 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 disposed between the two or more emission units. When the interlayer 130 includes the two or more emission units and the charge generation layer as described above, the light-emitting device 10 may be a tandem light-emitting device.

[0338] Hole transport region in interlayer 130

[0339] The hole transport region may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material (e.g., consisting of) a single layer, ii) a single-layer structure including (e.g., consisting of) a single layer including a plurality of materials different from each other, or iii) a multilayer structure including (including a plurality of materials different from each other) a plurality of layers.

[0340] 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.

[0341] In one or more embodiments, the hole transport region may have a multi-layer structure, which includes a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure or a hole injection layer / hole transport layer / emission assisting layer structure, wherein the constituent layers of each structure are stacked in sequence starting from the first electrode 110 in the order described.

[0342] In one or more embodiments, the hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:

[0343] Formula 201

[0344]

[0345] Formula 202

[0346]

[0347] Among them, in Equation 201 and Equation 202,

[0348] L 201 To L 204 may be independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 heterocyclic group,

[0349] L 205 Can be *-O-*', *-S-*', *-N(Q 201 )-*', unsubstituted or replaced by at least one R 10a Substituted C1-C 20 Alkylene, unsubstituted or substituted with at least one R 10a Substituted C2-C 20 Alkenylene, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 heterocyclic group,

[0350] xa1 to xa4 may each independently be an integer selected from 0 to 5,

[0351] xa5 may be an integer selected from 1 to 10,

[0352] R 201 to R 204 and Q 201 may be independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 heterocyclic group,

[0353] R 201 and R 202 may be optionally substituted by a single bond, unsubstituted or by at least one R 10a Substituted C1-C5 alkylene or unsubstituted or replaced by at least one R 10a The substituted C2-C5 alkenylene groups are linked to each other to form an unsubstituted or substituted R 10a Replaced C8-C 60 Polycyclic groups (e.g., carbazolyl, etc.) (e.g., see compound HT16, etc.),

[0354] R 203 and R 204 may be optionally substituted by a single bond, unsubstituted or by at least one R 10a Substituted C1-C5 alkylene or unsubstituted or replaced by at least one R 10a The substituted C2-C5 alkenylene groups are linked to each other to form an unsubstituted or substituted R 10a Replaced C8-C 60 polycyclic groups, and

[0355] na1 may be an integer selected from 1 to 4.

[0356] In one or more embodiments, each of Formula 201 and Formula 202 may include at least one selected from the group represented by Formula CY201 to Formula CY217:

[0357]

[0358] Among them, in formula CY201 to formula CY217, R 10b and R 10c Can be independently compared with reference R 10a Same as described, CY 201 To Ring CY 204 Can be independently C3-C 20 Carbocyclic or C1-C 20 heterocyclic group, and at least one hydrogen in Formula CY201 to Formula CY217 may be unsubstituted or replaced by R 10a replace.

[0359] In one or more embodiments, in Formula CY201 to Formula CY217, ring CY 201 To Ring CY 204 Each independently may be phenyl, naphthyl, phenanthryl or anthracenyl.

[0360] In one or more embodiments, each of Formula 201 and Formula 202 may include at least one selected from the group represented by Formulas CY201 to CY203.

[0361] In one or more embodiments, Formula 201 may include at least one selected from the group represented by Formulas CY201 to CY203 and at least one selected from the group represented by Formulas CY204 to CY217.

[0362] In one or more embodiments, in Formula 201, xa1 may be 1, R 201 may be a group represented by any one selected from Formula CY201 to Formula CY203, xa2 may be 0, and R 202It may be a group represented by any one selected from Formula CY204 to Formula CY207.

[0363] In one or more embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) any of the groups represented by Formula CY201 to Formula CY203.

[0364] In one or more embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) any 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.

[0365] In one or more embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) any of the groups represented by Formula CY201 to Formula CY217.

[0366] In one or more embodiments, the hole transport region may include: (for example, selected from) at least one of Compound HT1 to Compound HT46; 4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA); 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA); 4,4',4"-tris[N-(2-naphthyl)-N-phenylamino]triphenylamine (2-TNATA); N,N'-di(1-naphthyl)-N,N'-diphenyl-benzidine (NPB (NPD)); β-NPB; N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diphenylamine; amine (TPD); spiroTPD; spiroNPB; methylated NPB; 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC); 4,4'-bis[N,N'-(3-methylphenyl)amino]-3,3'-dimethylbiphenyl (HMTPD); 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA); polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA); poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS); polyaniline / camphorsulfonic acid (PANI / CSA); polyaniline / poly(4-styrenesulfonate) (PANI / PSS); or any combination thereof:

[0367]

[0368]

[0369]

[0370]

[0371]

[0372] The thickness of the hole transport region can 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 can be in the range of 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, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.

[0373] The emission-assisting layer can increase luminous efficiency by compensating for the optical resonance distance according to the wavelength of light emitted by the emission layer, and the electron blocking layer can prevent electrons from leaking from the emission layer to the hole transport region. The emission-assisting layer and the electron blocking layer may include materials that can be included in the hole transport region.

[0374] p-dopant

[0375] In one or more embodiments, in addition to one or more of the above materials, the hole transport region may further include a charge generation material for improved conductive properties. The charge generation material may be dispersed uniformly (e.g., substantially uniformly) or non-uniformly (e.g., in the form of a single layer including (e.g., consisting of) the charge generation material) in the hole transport region.

[0376] The charge generating material may be, for example, a p-dopant.

[0377] In one or more embodiments, the p-dopant may have a LUMO energy level of −3.5 eV or less.

[0378] In one or more embodiments, 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.

[0379] Non-limiting examples of the quinone derivative may include tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), and the like.

[0380] Non-limiting examples of the cyano group-containing compound may include dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) and / or a compound represented by Formula 221, etc.:

[0381]

[0382] Where, in formula 221,

[0383] R 221 to R 223 may be independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 heterocyclic group, and

[0384] Selected from R 221 to R 223 At least one of them can be independently C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group: cyano; -F; -Cl; -Br; -I; C1-C1-C1-substituted by cyano, -F, -Cl, -Br, -I or any combination thereof 20 or any combination thereof.

[0385] In a compound including element EL1 and element EL2, element EL1 may be a metal, a metalloid, or any combination thereof, and element EL2 may be a nonmetal, a metalloid, or any combination thereof.

[0386] Non-limiting examples of metals may include: alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), and / or cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), and / or 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 ( Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag) and / or gold (Au), etc.); late transition metals (e.g., zinc (Zn), indium (In) and / or tin (Sn), etc.); and / or lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb) and / or lutetium (Lu), etc.), etc.

[0387] Non-limiting examples of metalloids may include silicon (Si), antimony (Sb), and / or tellurium (Te), among others.

[0388] Non-limiting examples of the non-metal may include oxygen (O) and / or halogen (eg, F, Cl, Br, and / or I, etc.), and the like.

[0389] Non-limiting examples of compounds including element EL1 and element EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides and / or metal iodides, etc.), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides and / or metalloid iodides, etc.), metal tellurides, or any combination thereof.

[0390] Non-limiting examples of metal oxides may include tungsten oxide (e.g., WO, W2O3, WO2, WO3 and / or W2O5, etc.), vanadium oxide (e.g., VO, V2O3, VO2 and / or V2O5, etc.), molybdenum oxide (e.g., MoO, Mo2O3, MoO2, MoO3 and / or Mo2O5, etc.) and / or rhenium oxide (e.g., ReO3, etc.), etc.

[0391] Non-limiting examples of the metal halide may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and / or lanthanide metal halides, among others.

[0392] Non-limiting examples of alkali metal halides may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and / or CsI, among others.

[0393] Non-limiting examples of alkaline earth halides may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2 and / or BaI2, etc.

[0394] Non-limiting examples of transition metal halides may include titanium halides (e.g., TiF4, TiCl4, TiBr4, and / or TiI4, etc.), zirconium halides (e.g., ZrF4, ZrCl4, ZrBr4, and / or ZrI4, etc.), hafnium halides (e.g., HfF4, HfCl4, HfBr4, and / or HfI4, etc.), vanadium halides (e.g., VF3, VCl3, VBr3, and / or VI3, etc.), niobium halides (e.g., NbF3, NbCl3, NbBr3, and / or NbI3, etc.), tantalum halides (e.g., TaF3, TaCl3, TaBr3, etc.), 3 and / or TaI3, etc.), chromium halides (e.g., CrF3, CrCl3, CrBr3 and / or CrI3, etc.), molybdenum halides (e.g., MoF3, MoCl3, MoBr3 and / or MoI3, etc.), tungsten halides (e.g., WF3, WCl3, WBr3 and / or WI3, etc.), manganese halides (e.g., MnF2, MnCl2, MnBr2 and / or MnI2, etc.), technetium halides (e.g., TcF2, TcCl2, TcBr2 and / or TcI2, etc.), rhenium halides (e.g., ReF2, ReCl2, ReBr2 and / or Re I2, etc.), iron (II) halides (e.g., FeF2, FeCl2, FeBr2 and / or FeI2, etc.), ruthenium halides (e.g., RuF2, RuCl2, RuBr2 and / or RuI2, etc.), osmium halides (e.g., OsF2, OsCl2, OsBr2 and / or OsI2, etc.), cobalt halides (e.g., CoF2, CoCl2, CoBr2 and / or CoI2, etc.), rhodium halides (e.g., RhF2, RhCl2, RhBr2 and / or RhI2, etc.), iridium halides (e.g., IrF2, IrCl2, IrBr2 and / or Or IrI2, etc.), nickel halides (e.g., NiF2, NiCl2, NiBr2 and / or NiI2, etc.), palladium halides (e.g., PdF2, PdCl2, PdBr2 and / or PdI2, etc.), platinum halides (e.g., PtF2, PtCl2, PtBr2 and / or PtI2, etc.), cuprous (I) halides (e.g., CuF, CuCl, CuBr and / or CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr and / or AgI, etc.) and / or gold halides (e.g., AuF, AuCl, AuBr and / or AuI, etc.), etc.

[0395] Non-limiting examples of late transition metal halides may include zinc halides (e.g., ZnF2, ZnCl 2、 ZnBr2 and / or ZnI2, etc.), indium halide (e.g., InI3, etc.) and / or tin halide (e.g., SnI2, etc.), etc.

[0396] Non-limiting examples of lanthanide metal halides may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3 and / or SmI3, etc.

[0397] Non-limiting examples of the metalloid halide may include antimony halide (eg, SbCl 5 , etc.), and the like.

[0398] Non-limiting examples of metal tellurides may include alkali metal tellurides (e.g., Li2Te, Na2Te, K2Te, Rb2Te and / or Cs2Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe and / or BaTe, etc.), transition metal tellurides (e.g., TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, F eTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe and / or Au2Te, etc.), late transition metal tellurides (e.g., ZnTe, etc.) and / or lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe and / or LuTe, etc.), etc.

[0399] Emission layer in interlayer 130

[0400] When the light-emitting device 10 is a full-color 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 the sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer and a blue emission layer, wherein the two or more layers are in contact with each other or separated from each other to emit white light (e.g., combined white light). In one or more embodiments, the emission layer may include two or more materials selected from 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 (e.g., combined white light).

[0401] The emissive layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.

[0402] The amount of the dopant in the emission layer may be in the range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.

[0403] In one or more embodiments, the emissive layer may include quantum dots.

[0404] In one or more embodiments, 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.

[0405] The thickness of the emission layer can be about to about (For example, about to about When the thickness of the emission layer is within the above range, excellent or appropriate light emitting characteristics can be obtained without significantly increasing the driving voltage.

[0406] main body

[0407] In one or more embodiments, the host may include a compound represented by Formula 301:

[0408] Formula 301

[0409] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 ,

[0410] Wherein, in formula 301,

[0411] Ar 301 and L 301 may be independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 heterocyclic group,

[0412] xb11 can be 1, 2 or 3,

[0413] xb1 may be an integer selected from 0 to 5,

[0414] R 301 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by 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 60Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-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 ),

[0415] xb21 may be an integer selected from 1 to 5, and

[0416] Q 301 To Q 303 Each may independently be the same as described with reference to Q1.

[0417] In one or more embodiments, if (for example, when) xb11 in Formula 301 is 2 or greater, then two or more Ar 301 can be connected to each other via a single bond.

[0418] In one or more embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:

[0419]

[0420] In Formula 301-1 and Formula 301-2,

[0421] Ring A 301 To Ring A 304 may be independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 heterocyclic group,

[0422] X 301 Can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305),

[0423] xb22 and xb23 can each independently be 0, 1 or 2,

[0424] L 301 , xb1 and R 301 each being the same as described herein,

[0425] L 302 To L 304 Can be independently compared with reference L 301 Same as described,

[0426] xb2 to xb4 may each independently be the same as described with reference to xb1, and

[0427] R 302 to R 305 and R 311 to R 314 Can be independently compared with reference R 301 Same as described.

[0428] In one or more embodiments, the host may include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. For example, in some embodiments, the host may include a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.

[0429] In one or more embodiments, the host may include: (e.g., selected from) at least one of Compounds H1 to H128; 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(carbazol-9-yl)benzene (mCP); 1,3,5-tri(carbazol-9-yl)benzene (TCP); or any combination thereof:

[0430]

[0431]

[0432]

[0433]

[0434]

[0435]

[0436]

[0437] Phosphorescent dopants

[0438] The phosphorescent dopant may include at least one transition metal as a central metal.

[0439] 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.

[0440] The phosphorescent dopant may be electrically neutral.

[0441] In one or more embodiments, the phosphorescent dopant may include an organometallic compound represented by Formula 401:

[0442] Formula 401

[0443] M(L 401 ) xc1 (L 402 ) xc2

[0444] Formula 402

[0445]

[0446] Among them, in formula 401 and formula 402,

[0447] 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)),

[0448] L 401 may be a ligand represented by Formula 402, and xc1 may be 1, 2, or 3, wherein if (for example, when) xc1 is 2 or greater, two or more L 401 may be substantially the same as or different from each other,

[0449] L 402 may be an organic ligand, and xc2 may be 0, 1, 2, 3, or 4, wherein, if (for example, when) xc2 is 2 or greater, two or more L 402 may be substantially the same as or different from each other,

[0450] X 401 and X 402 may each independently be nitrogen or carbon,

[0451] Ring A 401 and Ring A 402 Can be independently C3-C 60 Carbocyclic or C1-C 60 heterocyclic group,

[0452] T 401 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*'、*-C(Q 411 )(Q 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*' or *=C=*',

[0453] X 403 and X 404 can be independently a chemical bond (eg, a covalent bond or a coordination bond), O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ),

[0454] Q 411 To Q 414 can be independently the same as described with reference to Q1,

[0455] R 401 and R 402 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by at least one R 10a Substituted C1-C 20 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 20 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-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 ),

[0456] Q 401 To Q403 can be independently the same as described with reference to Q1,

[0457] xc11 and xc12 may each independently be an integer selected from 0 to 10, and

[0458] * and *' in Formula 402 each indicate a bonding site to M in Formula 401.

[0459] In one or more embodiments, 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.

[0460] In one or more embodiments, if (eg, when) xc1 in equation 401 is 2 or greater, then two or more L 401 Ring A 401 The two of them may be optionally connected via T as a linking group 402 connected to each other, and / or two or more L 401 Ring A 402 The two of them may be optionally connected via T as a linking group 403 Connected to each other (see Compound PD1 to Compound PD4 and Compound PD7). 402 and T 403 Each combined with T 401 Same as described.

[0461] In formula 401, L 402 It can be an organic ligand. For example, L 402 It may include a halogen, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), a -C(=O) group, an isonitrile group, a -CN group, a phosphorus-containing group (e.g., a phosphine group and / or a phosphite group, etc.), or any combination thereof.

[0462] The phosphorescent dopant may include, for example, at least one of Compound PD1 to Compound PD39 (for example, any one selected therefrom) or any combination thereof:

[0463]

[0464]

[0465]

[0466] Fluorescent dopants

[0467] In one or more embodiments, the fluorescent dopant may include an amine-containing compound, a styryl-containing compound, or any combination thereof.

[0468] In one or more embodiments, the fluorescent dopant may include a compound represented by Formula 501:

[0469] Formula 501

[0470]

[0471] Wherein, in formula 501,

[0472] Ar 501 , L 501 To L 503 、R 501 and R 502 may be independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 heterocyclic group,

[0473] xd1 to xd3 may each independently be 0, 1, 2 or 3, and

[0474] xd4 can be 1, 2, 3, 4, 5 or 6.

[0475] In one or more embodiments, Ar in Formula 501 501 It may be a condensed ring group in which three or more monocyclic groups are condensed to each other (for example, anthracenyl, 1,2-triphenylenyl and / or pyrenyl, etc.).

[0476] In one or more embodiments, xd4 in equation 501 may be 2.

[0477] In one or more embodiments, the fluorescent dopant may include: at least one of Compound FD1 to Compound FD37 (for example, any one selected therefrom); 4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl (DPVBi); 4,4'-bis[4-(N,N-diphenylamino)phenylvinyl]biphenyl (DPAVBi); or any combination thereof:

[0478]

[0479]

[0480]

[0481] Delayed fluorescence materials

[0482] In one or more embodiments, the emission layer may include a delayed fluorescent material (compound).

[0483] Herein, the delayed fluorescent material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.

[0484] The delayed fluorescent material included in the emission layer may act as a host or a dopant depending on the type or kind of other materials included in the emission layer.

[0485] In one or more embodiments, the difference (e.g., the absolute value of 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 but at most (e.g., not greater 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 is within the above range, upconversion of the delayed fluorescent material from the triplet state to the singlet state may occur efficiently, and thus, the light-emitting device 10 may have improved luminous efficiency.

[0486] In one or more embodiments, the delayed fluorescent material may include: i) at least one electron donor (eg, a π-electron-rich C3-C 60 Cyclic groups, such as carbazolyl, etc.) and at least one electron acceptor (e.g., sulfoxide, cyano and / or π-electron-deficient nitrogen-containing C1-C 60 heterocyclic group, etc.), ii) including C8-C 60 Polycyclic materials, the C8-C 60 The polycyclic group includes two or more cyclic groups fused to each other while sharing boron (B), and / or iii) and the like.

[0487] Non-limiting examples of the delayed fluorescent material may include (eg, selected from) at least one of Compound DF1 to Compound DF14:

[0488]

[0489]

[0490] quantum dots

[0491] In one or more embodiments, the emissive layer may include quantum dots.

[0492] The term "quantum dot" as used herein refers to a crystal of a semiconductor compound and may include any material capable of emitting light at one or more appropriate emission wavelengths depending on the size of the crystal.

[0493] The diameter of a quantum dot can be, for example, in the range of about 1 nm to about 10 nm. In the present disclosure, when a dot, a plurality of dots, or a dot particle is spherical, "diameter" indicates the particle size or average particle size, and when the particle is non-spherical, "diameter" indicates the major axis length or average major axis length. The diameter of the particle can be measured using a scanning electron microscope or a particle size analyzer. For example, a HORIBA, LA-950 laser particle size analyzer can be used as a particle size analyzer. When the size of the particle is measured using a particle size analyzer, the average particle size is referred to as D 50 . D 50 It refers to the average diameter of the particles whose cumulative volume corresponds to 50% by volume in a particle size distribution (e.g., cumulative distribution), and refers to the value of the particle size corresponding to 50% starting from the smallest particle when the total number of particles is 100% in a distribution curve accumulated in order from the smallest particle size to the largest particle size.

[0494] Quantum dots can be synthesized by a wet chemical process, a metal organic chemical vapor deposition (MOCVD) process, a molecular beam epitaxy (MBE) process, or any similar process.

[0495] The wet chemical process is a method that includes mixing a quantum dot precursor material with an organic solvent and then growing quantum dot particle crystals. As the quantum dot particle crystals grow, the organic solvent naturally acts as a dispersant that coordinates on the surface of the quantum dot particle crystals and controls the growth of the quantum dot particle crystals. This allows the growth of quantum dot crystal particles to be controlled or selected through a process that is less expensive and easier than vapor deposition methods such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).

[0496] The 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.

[0497] Non-limiting 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, etc.; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, Cd ... dZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe and / or MgZnS, etc.; quaternary compounds, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and / or HgZnSTe, etc.; or any combination thereof.

[0498] Non-limiting examples of Group 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 GaNPs, GaNAs, GaNSb, GaPAs, GaPSb, AlNPs, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNPs, InAlP, InNAs, InNSb, InPAs, and / or InPSb; quaternary compounds such as GaAlNPs, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNPs, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNPs, InAlNAs, InAlNSb, InAlPAs, and / or InAlPSb; or any combination thereof. In one or more embodiments, the Group III-V semiconductor compound may further include a Group II element. Non-limiting examples of the Group III-V semiconductor compound further including a Group II element may include InZnP, InGaZnP, and / or InAlZnP, among others.

[0499] Non-limiting examples of III-VI semiconductor compounds may include: binary compounds, such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3 and / or InTe, etc.; ternary compounds, such as InGaS3 and / or InGaSe3, etc.; or any combination thereof.

[0500] Non-limiting examples of Group I-III-VI semiconductor compounds may include: ternary compounds such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2 and / or AgAlO2, etc.; or any combination thereof.

[0501] Non-limiting examples of Group IV-VI semiconductor compounds may include: binary compounds, such as SnS, SnSe, SnTe, PbS, PbSe and / or PbTe, etc.; ternary compounds, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe and / or SnPbTe, etc.; quaternary compounds, such as SnPbSSe, SnPbSeTe and / or SnPbSTe, etc.; or any combination thereof.

[0502] The 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.

[0503] 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 substantially uniform concentration or a non-uniform concentration.

[0504] In one or more embodiments, the quantum dots may have a single structure (wherein the concentration of each element in the quantum dots is substantially uniform) or may have a core-shell dual structure. For example, the material included in the core and the material included in the shell may be different from each other.

[0505] The shell of a quantum dot can act as a protective layer to prevent chemical denaturation of the core to maintain semiconductor properties and / or 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, where the concentration of the element present in the shell decreases toward the center of the core.

[0506] Examples of quantum dot shells may include metal oxides, metalloid oxides, or non-metal oxides, semiconductor compounds, and / or combinations thereof (e.g., any suitable combination thereof). Non-limiting examples of metal oxides, metalloid oxides, or non-metal oxides may include binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and / or NiO, etc.; ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, and / or CoMn2O4, etc.; or any combination thereof. Examples of semiconductor compounds may include Group II-VI semiconductor compounds as described herein; 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. For example, semiconductor compounds suitable as shells 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.

[0507] The quantum dots may have an emission spectrum with a full width at half maximum (FWHM) of about 45 nm or less, about 40 nm or less, or, for example, about 30 nm or less. When the FWHM of the emission spectrum of the quantum dots is within these ranges, the quantum dots may have improved color purity or improved color reproducibility. In addition, because the light emitted by the quantum dots is emitted in all directions, a wide viewing angle may be improved.

[0508] Additionally, quantum dots may be in the form of spherical nanoparticles, pyramidal nanoparticles, multi-armed nanoparticles, cubic nanoparticles, nanotubes, nanowires, nanofibers, and / or nanoplates, among others.

[0509] Because the band gap of quantum dots can be adjusted by controlling their size, light having one or more appropriate wavelength bands can be obtained from the quantum dot emission layer. Accordingly, by using quantum dots of different sizes, a light-emitting device that emits light in one or more appropriate wavelength bands can be implemented. For example, the size of the quantum dots can be selected to ensure that the quantum dots emit red, green, and / or blue light. In addition, quantum dots of appropriate size (diameter) can be configured to emit white light using a combination of one or more appropriate colors of light.

[0510] Electron transport region in interlayer 130

[0511] The electron transport region may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material (e.g., consisting of) a single layer, ii) a single-layer structure including (e.g., consisting of) a single layer including multiple materials different from each other, or iii) a multilayer structure including (including) multiple layers of multiple materials different from each other.

[0512] 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.

[0513] In one or more embodiments, 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 sequentially starting from the emission layer in the order described.

[0514] In one or more embodiments, the electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, 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 C1-C 60 Heterocyclic group.

[0515] In one or more embodiments, the electron transport region may include a compound represented by Formula 601:

[0516] Formula 601

[0517] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 ,

[0518] Wherein, in formula 601,

[0519] Ar 601 and L 601 may be independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 heterocyclic group,

[0520] xe11 can be 1, 2 or 3,

[0521] xe1 can be 0, 1, 2, 3, 4 or 5,

[0522] R 601It may be unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-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 ),

[0523] Q 601 To Q 603 can be independently the same as described with reference to Q1,

[0524] xe21 can be 1, 2, 3, 4, or 5, and

[0525] Selected from Ar 601 , L 601 and R 601 At least one of them may be independently unsubstituted or replaced by at least one R 10a Substituted π-electron-deficient nitrogen-containing C1-C 60 Heterocyclic group.

[0526] In one or more embodiments, if (for example, when) xe11 in Formula 601 is 2 or greater, then two or more Ar 601 can be connected to each other via a single bond.

[0527] In one or more embodiments, Ar in Formula 601 601 It may be unsubstituted or substituted with at least one R 10a substituted anthracenyl.

[0528] In one or more embodiments, the electron transport region may include a compound represented by Formula 601-1:

[0529] Formula 601-1

[0530]

[0531] Among them, in formula 601-1,

[0532] 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 selected from X 614To X 616 At least one of may be N,

[0533] L 611 To L 613 Can be independently compared with reference L 601 Same as described,

[0534] xe611 to xe613 can each independently be the same as described with reference to xe1,

[0535] R 611 to R 613 Can be independently compared with reference R 601 Same as described, and

[0536] R 614 to R 616 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group.

[0537] In one or more embodiments, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 may each independently be 0, 1, or 2.

[0538] In one or more embodiments, the electron transport region may include: (for example, selected from) at least one of Compound ET1 to Compound ET45; 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP); 4,7-diphenyl-1,10-phenanthroline (Bphen); tris(8-hydroxyquinolinolato)aluminum (Alq3); bis(2-methyl-8-hydroxyquinolinolato-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq); 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ); 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ); or any combination thereof:

[0539]

[0540]

[0541]

[0542]

[0543] The thickness of the electron transport region can 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 in the range of about to about (For example, about to about ), and the thickness of the electron transport layer can be in the range of 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 the above range, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.

[0544] In one or more embodiments, the electron transport region (eg, the electron transport layer in the electron transport region) may further include a metal-containing material in addition to one or more of the above materials.

[0545] 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 Li ion, Na ion, K ion, Rb ion, or Cs ion, and the metal ion of the alkaline earth metal complex may be Be ion, Mg ion, Ca ion, Sr ion, or Ba ion. The ligand coordinated to the metal ion of the alkali metal complex or the metal ion of 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.

[0546] In one or more embodiments, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (Liq) or compound ET-D2:

[0547]

[0548] In one or more embodiments, 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 directly contact the second electrode 150.

[0549] The electron injection layer may have: i) a single-layer structure including a single layer (e.g., consisting of a single layer) that includes a single material (e.g., consisting of a single material), ii) a single-layer structure including a single layer (e.g., consisting of a single layer) that includes multiple materials different from each other, or iii) a multi-layer structure including multiple layers (including multiple materials different from each other).

[0550] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0551] 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.

[0552] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may respectively include oxides, halides (e.g., fluorides, chlorides, bromides, and / or iodides, etc.) or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.

[0553] The alkali metal compound may include: alkali metal oxides, such as Li2O, Cs2O, and / or K2O, etc.; alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and / or KI, etc.; or any combination thereof. The alkaline earth metal 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 the condition 0 < x < 1) and / or Ba x Ca 1-x O (where x is a real number satisfying the condition 0 < x < 1), etc. The rare earth metal compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In one or more embodiments, the rare earth metal compound may include lanthanide metal tellurides. Non-limiting examples of lanthanide metal tellurides may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, and / or Lu2Te3, etc.

[0554] The alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex may respectively include i) one of the metal ions of the alkali metal, one of the metal ions of the alkaline earth metal, and one of the metal ions of the rare earth metal, and ii) a ligand bonded to the metal ion (e.g., the corresponding metal ion), for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

[0555] In one or more embodiments, as described above, the electron injection layer may include (e.g., 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. In one or more embodiments, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).

[0556] In one or more embodiments, the electron injection layer may include (e.g., consist of) the following: i) an alkali metal-containing compound (e.g., an alkali metal halide), or ii) a) an alkali metal-containing compound (e.g., an alkali metal halide) and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, in one or more embodiments, 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.

[0557] When the electron injection layer further includes an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkaline earth metal-containing compound, rare earth metal-containing compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or any combination thereof can be uniformly (e.g., substantially uniformly) or non-uniformly dispersed in the matrix including the organic material.

[0558] The thickness of the electron injection layer can be about to about (For example, about to about When the thickness of the electron injection layer is within the above range, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.

[0559] Second electrode 150

[0560] The second electrode 150 is disposed on the interlayer 130 having the structure described above. The second electrode 150 may be a cathode serving as an electron injection electrode and may be formed using metals, alloys, conductive compounds, or any combination thereof each having a low work function.

[0561] 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 transflective electrode, or a reflective electrode.

[0562] The second electrode 150 may have a single-layer structure or a multi-layer structure including a plurality of layers.

[0563] Capping layer

[0564] The first capping layer may be disposed outside the first electrode 110 (e.g., on the first electrode 110), and / or the second capping layer may be disposed outside the second electrode 150 (e.g., on the second electrode 150). For example, in one or more embodiments, the 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 stacked in sequence in the order recited, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in sequence in the order recited, 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 stacked in sequence in the order recited.

[0565] In one or more embodiments, light generated in the emission layer of the interlayer 130 of the light-emitting device 10 can be extracted to the outside through the first electrode 110 as a transflective electrode or a transmissive electrode and the first capping layer. In one or more embodiments, light generated in the emission layer of the interlayer 130 of the light-emitting device 10 can be extracted to the outside through the second electrode 150 as a transflective electrode or a transmissive electrode and the second capping layer.

[0566] The first capping layer and the second capping layer can increase the external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light emitting device 10 can be increased, so that the light emitting efficiency of the light emitting device 10 can be improved.

[0567] Each of the first capping layer and the second capping layer may include a material having a refractive index of 1.6 or greater (eg, at 589 nm).

[0568] 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.

[0569] At least one of the first capping layer and the second capping layer may each independently (e.g., 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 each be optionally substituted with a substituent comprising O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In one or more embodiments, at least one of the first capping layer and the second capping layer may (e.g., the first capping layer and the second capping layer may each independently) include an amine-containing compound.

[0570] In one or more embodiments, at least one of the first capping layer and the second capping layer may (eg, the first capping layer and the second capping layer may each independently) include the compound represented by Formula 201, the compound represented by Formula 202, or any combination thereof.

[0571] In one or more embodiments, at least one of the first capping layer and the second capping layer may (for example, the first capping layer and the second capping layer may each independently) include: (for example, selected from) at least one of compounds HT28 to HT33; (for example, selected from) at least one of compounds CP1 to CP6; β-NPB; or any combination thereof:

[0572]

[0573] membrane

[0574] One or more suitable films may include the heterocyclic compound represented by Formula 1. Accordingly, one or more aspects of the embodiments of the present disclosure relate to a film including the heterocyclic compound represented by Formula 1. The film may be, for example, an optical member (or light control element) (e.g., a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancing layer, a selective light absorption layer, a polarizing layer and / or a quantum dot-containing 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 and / or a dielectric layer, etc.), etc.

[0575] electronic devices

[0576] The light emitting device may be included in one or more suitable electronic devices. For example, the electronic device including the light emitting device may be a light emitting device and / or an authentication device.

[0577] In one or more embodiments, in addition to the 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 arranged in at least one direction in which the light emitted from the light-emitting device travels. For example, in one or more embodiments, the light emitted from the light-emitting device may be blue light or white light (e.g., a combined white light). The details regarding the light-emitting device may be the same as described herein. In one or more embodiments, the color conversion layer may include quantum dots. The quantum dots may be, for example, as described herein.

[0578] 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.

[0579] A pixel defining film may be disposed between the plurality of sub-pixel regions to define each of the plurality of sub-pixel regions.

[0580] In one or more embodiments, the color filter may further include a plurality of color filter regions and a light shielding pattern disposed 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 disposed between the plurality of color conversion regions.

[0581] The plurality of color filter regions (or color conversion regions) may include: a first region configured to emit a first color of light; a second region configured to emit a second color of light; and / or a third region configured to emit a third color of light, wherein the first, second, and / or third color of light may have different maximum emission wavelengths. For example, in one or more embodiments, the first color of light may be red light, the second color of light may be green light, and the third color of light may be blue light. For example, in one or more embodiments, the plurality of color filter regions (or color conversion regions) may include quantum dots. For example, the first region may include red quantum dots to emit red light, the second region may include green quantum dots to emit green light, and the third region may not include (e.g., may exclude) quantum dots. Details regarding the quantum dots may be the same as described herein. Each of the first, second, and / or third regions may further include a scatterer.

[0582] In one or more embodiments, a light-emitting device may emit a first light, a first region may be configured to absorb the first light to emit a first-first color light, a second region may be configured to absorb the first light to emit a second-first color light, and a third region may be configured to absorb the first light to emit a third-first color light. In this regard, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. For example, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.

[0583] In one or more embodiments, in addition to the 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 one selected from the source electrode and the drain electrode may be electrically connected to the first electrode or the second electrode of the light-emitting device.

[0584] The thin film transistor may further include a gate electrode and / or a gate insulating film, etc.

[0585] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, and / or an oxide semiconductor, among others.

[0586] In one or more embodiments, the electronic device may further include a sealing portion for sealing the light-emitting device. The sealing portion may be arranged between the color filter and / or the color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside, and at the same time (e.g., synchronously) prevents ambient air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate 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.

[0587] In one or more embodiments, in addition to the color filter and / or color conversion layer, various functional layers may be disposed on the sealing portion depending on the intended use of the electronic device. Non-limiting examples of these functional layers include a touch screen layer and / or a polarizing layer. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer.

[0588] 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 and / or pupils, etc.) In addition to the light emitting device as described above, the authentication device may further include a biometric information collector.

[0589] Electronic devices (eg, light emitting devices) can be applied to various electronic equipment.

[0590] In one or more embodiments, the electronic device may be applied to one or more of a display, a light source, a lighting device, a personal computer (e.g., a mobile personal computer), a mobile phone, a digital camera, an electronic notepad, an electronic dictionary, an electronic game console, a medical tool (e.g., an electronic thermometer, a blood pressure monitor, a blood glucose meter, a pulse measuring device, a pulse wave measuring device, an electrocardiogram display, an ultrasound diagnostic device, or an endoscope display), a fish finder, one or more appropriate measuring tools, an instrument (e.g., an instrument for vehicles, aircraft, and ships), and a projector, etc.

[0591] electronic equipment

[0592] The electronic device may be applied to various electronic devices. Therefore, the light emitting device may be included in one or more appropriate electronic devices.

[0593] In one or more embodiments, the light emitting device may be applied to various electronic devices. The electronic devices may include the light emitting device and may further include a module or device having another function in addition to the light emitting device.

[0594] In one or more embodiments, the electronic equipment including the light emitting device may be at least one of 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 stretchable display, a laser printer, a telephone, a mobile phone, a tablet computer, a tablet phone computer, a 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 with multiple displays stitched together, a theater screen, a stadium screen, a light therapy device, and a sign.

[0595] The light emitting device may have excellent or appropriate light emitting efficiency and a long device life, and thus, electronic equipment including the light emitting device may have characteristics such as high brightness, high resolution, and low power consumption.

[0596] Figure 2 and Figure 3 Description

[0597] Figure 2 is a schematic cross-sectional view of the structure of a light emitting device according to one or more embodiments of the present disclosure.

[0598] Figure 2 The light emitting apparatus may include a substrate 100, a thin film transistor (TFT), a light emitting device, and a sealing portion 300 that seals the light emitting device.

[0599] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be on the substrate 100. The buffer layer 210 may prevent or reduce impurities from penetrating through the substrate 100 and may provide a flat surface on the substrate 100.

[0600] 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.

[0601] 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.

[0602] A gate insulating film 230 for insulating 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 .

[0603] An interlayer insulating film 250 may be on the gate electrode 240. The interlayer insulating film 250 may be disposed between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate each other.

[0604] The source electrode 260 and the drain electrode 270 may be on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may be arranged to contact the exposed portions of the source region and the drain region of the active layer 220, respectively.

[0605] The TFT may be electrically connected to the light-emitting device to drive the light-emitting device and may be covered and protected by the passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The light-emitting device may be provided on the passivation layer 280. The light-emitting device may include a first electrode 110, an interlayer 130, and a second electrode 150.

[0606] The first electrode 110 may be on the passivation layer 280. The passivation layer 280 may be arranged to expose a portion of the drain electrode 270 without completely covering the drain electrode 270, and the first electrode 110 may be arranged to be connected to the exposed portion of the drain electrode 270.

[0607] A pixel defining film 290 comprising an insulating material may be on the first electrode 110. The pixel defining film 290 may expose a specific area of ​​the first electrode 110, and the interlayer 130 may be formed in the exposed area of ​​the first electrode 110. The pixel defining film 290 may be a polyimide-based organic film or a polyacrylic organic film. In one or more embodiments, at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel defining film 290 to form a common layer. For example, at least some layers of the interlayer 130 may extend beyond the top of the pixel defining film 290 to form a common layer.

[0608] The second electrode 150 may be on the interlayer 130, and the capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.

[0609] The sealing portion 300 may be on the capping layer 170. The sealing portion 300 may be disposed on the light emitting device to protect the light emitting device from moisture and / or oxygen. The sealing portion 300 may include an inorganic film including silicon nitride (SiN x , for example, Si3N4), silicon oxide (SiO x , for example, SiO2), indium tin oxide, indium zinc oxide or any combination thereof; an organic film comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (for example, polymethyl methacrylate and / or polyacrylic acid, etc.), an epoxy resin (for example, aliphatic glycidyl ether (AGE), etc.) or any combination thereof; or any combination of an inorganic film and an organic film.

[0610] Figure 3 is a schematic cross-sectional view of the structure of a light emitting device according to one or more embodiments of the present disclosure.

[0611] Figure 3 Light-emitting devices and Figure 2 The light emitting device is substantially the same as that of FIG. 1 , except that the light shielding pattern 500 and the functional region 400 are additionally arranged on the sealing portion 300. The functional region 400 may be i) a color filter region, ii) a color conversion region, or iii) a combination of a color filter region and a color conversion region. In one or more embodiments, Figure 3 The light-emitting device included in the light-emitting apparatus may be a series light-emitting device.

[0612] Figure 4 Description

[0613] Figure 4 FIG is a block diagram of an electronic device 1 according to an embodiment. Figure 4 According to one embodiment, the electronic device 1 may include a light emitting module 11 , a processor 12 , a memory 13 and a power supply module 14 .

[0614] The processor 12 may include at least one of a central processing unit (CPU), an application processor (AP), a graphics processing unit (GPU), a communication processor (CP), an image signal processor (ISP), and a controller.

[0615] The memory 13 can store data information required for the operation of the processor 12 or the light module 11. When the processor 12 executes the application stored in the memory 13, the video data signal and / or the input control signal are transmitted to the light module 11, which processes the received signal to output the video information through the display screen.

[0616] The power module 14 may include a power module such as a power adapter or a battery, and a power conversion module that converts power provided by the power module to generate power required for the operation of the electronic device 1 .

[0617] At least one of the components of the electronic device 1 described above may be included in the light-emitting device according to the aforementioned embodiment. Furthermore, some of the individual modules functionally included in a single module may be incorporated into the light-emitting device, while others may be provided separately from the light-emitting device. For example, the light-emitting device may include the light-emitting module 11, and the processor 12, memory 13, and power supply module 14 may be provided as separate devices within the electronic device 1 rather than as part of the light-emitting device.

[0618] Figure 5 Description

[0619] Figure 5 is a schematic diagram of an electronic device according to one or more embodiments.

[0620] refer to Figure 5 , electronic equipment to which electronic devices (e.g., light-emitting devices) are applied include not only image display electronic equipment such as smart phones 1_1a, tablet personal computers 1_1b, laptop computers 1_1c, TVs 1_1d, and desktop monitors 1_1e, but also wearable electronic equipment including light-emitting modules such as smart glasses 1_2a, head-mounted displays 1_2b, and smart watches 1_2c, and vehicle electronic equipment 1_3 including light-emitting modules such as instrument panels, center consoles, center information displays (CIDs) placed on the instrument panels, and interior mirror displays.

[0621] Figure 6 Description

[0622] Figure 6Schematic perspective view of an electronic device 1 including a light-emitting device according to one or more embodiments of the present disclosure. As an electronic device that displays moving images 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 or ultra-mobile personal computer (UMPC)) and one or more appropriate products (such as a television, a laptop computer, a monitor, a billboard or an Internet of Things (IoT) device). The electronic device 1 may be such a product or a part thereof. In one or more embodiments, the electronic device 1 may be a wearable device (such as a smart watch, a watch phone, a glasses-type or glasses-like display or a head-mounted display (HMD)) or a part of a wearable device. However, the embodiments of the present disclosure are not limited thereto. For example, in one or more embodiments, the electronic device 1 may include a dashboard, a center console, or a center information display (CID) arranged on the dashboard of the vehicle, an interior mirror display replacing the side mirrors of the vehicle, an entertainment display for the rear seats of the vehicle, a display arranged on the backrest of its front seat, a head-up display (HUD) installed in front of the vehicle or projected on its front windshield, or a computer-generated hologram augmented reality head-up display (CGH AR HUD). For convenience of explanation, Figure 6 One or more embodiments are explained in which the electronic device 1 is a smartphone.

[0623] The electronic equipment 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device of the electronic equipment 1 may implement an image through an array of a plurality of pixels two-dimensionally arranged in the display area DA.

[0624] The non-display area NDA is an area where no image is displayed and may completely surround the display area DA (e.g., surround the display area DA). A driver for providing electrical signals or power to display elements arranged in the display area DA may be arranged in the non-display area NDA. Pads that can be electrically connected to electronic components or a printed circuit board may also be arranged in the non-display area NDA.

[0625] In the electronic device 1, the length in the x-axis direction and the length (eg, width) in the y-axis direction may be different from each other. Figure 6 As shown in FIG, the length in the x-axis direction may be smaller than the length in the y-axis direction (e.g., width). In one or more embodiments, the length in the x-axis direction may be substantially the same as the length in the y-axis direction (e.g., width). In one or more embodiments, the length in the x-axis direction may be larger than the length in the y-axis direction (e.g., width).

[0626] Figure 7and Figures 8A to 8C Description

[0627] Figure 7 is a schematic diagram of the exterior of a vehicle 1000 as an electronic device including a light emitting device according to one or more embodiments. Figures 8A to 8C Each is a schematic diagram of the interior of a vehicle 1000 according to one or more embodiments.

[0628] refer to Figure 7 、 Figure 8A 、 Figure 8B and Figure 8C The vehicle 1000 may refer to one or more suitable devices for moving an object to be transported (such as a person, object, or animal) from a starting point to a destination point. The vehicle 1000 may include a vehicle that travels on roads or tracks, a ship that moves on the ocean or river, and / or an airplane that flies in the air using air motion.

[0629] In one or more embodiments, vehicle 1000 may travel on roads or tracks. Vehicle 1000 may move in a specific direction based on the rotation of at least one of its wheels. For example, vehicle 1000 may include a three-wheeled or four-wheeled vehicle, construction machinery, a two-wheeled vehicle, a prime mover, a bicycle, or a train traveling on tracks.

[0630] Vehicle 1000 may include a vehicle body having an interior and an exterior, and a chassis in which mechanical equipment required for driving is mounted as other components in addition to the vehicle body. The exterior of the vehicle body may include a front panel, a hood, a roof panel, a rear panel, a trunk, and / or pillars provided at the boundaries between the doors. The chassis of 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 system, and / or front and rear wheels.

[0631] The vehicle 1000 may include side windows 1100 , a front window 1200 , side mirrors 1300 , an instrument panel 1400 , a center console 1500 , a passenger seat instrument panel 1600 , and a display device 2 .

[0632] The side window glass 1100 and the front window glass 1200 may be separated by pillars disposed between the side window glass 1100 and the front window glass 1200 .

[0633] A side window glass 1100 may be mounted on the side of the vehicle 1000. In one or more embodiments, the side window glass 1100 may be mounted on a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided, and the plurality of side window glasses 1100 may face each other. In one or more embodiments, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In one or more embodiments, the first side window glass 1110 may be positioned adjacent to the instrument panel 1400. The second side window glass 1120 may be positioned adjacent to the passenger seat instrument panel 1600.

[0634] In one or more embodiments, the side window glasses 1100 may be spaced and / or separated (e.g., spaced or separated) from each other in the x-direction or the -x-direction (the direction opposite to the x-direction). For example, the first side window glass 1110 and the second side window glass 1120 may be spaced and / or separated (e.g., spaced or separated) from each other in the x-direction or the -x-direction. For example, the imaginary straight line L connecting the side window glasses 1100 may extend in the x-direction or the -x-direction. For example, in one or more embodiments, the imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 may extend in the x-direction or the -x-direction.

[0635] The front window glass 1200 may be mounted at the front of the vehicle 1000. The front window glass 1200 may be disposed between the side window glasses 1100 that are opposed to each other (eg, face each other).

[0636] Side-view mirror 1300 can provide a rear view of vehicle 1000. Side-view mirror 1300 can be mounted on the exterior of vehicle 1000. In one or more embodiments, a plurality of side-view mirrors 1300 can be provided. Any one of the plurality of side-view mirrors 1300 can be positioned outside first side window glass 1110. Another one of the plurality of side-view mirrors 1300 can be positioned outside second side window glass 1120.

[0637] Instrument panel 1400 may be arranged in front of the steering wheel and may include a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge, a turn signal indicator, a high beam indicator, warning lights, a seat belt warning light, an odometer, a driving recorder, an automatic gear selection indicator, a door open warning light, an engine oil warning light, and / or a low fuel warning light.

[0638] 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 / or a seat heater are arranged. The center console 1500 may be arranged on one side of the instrument panel 1400 .

[0639] Passenger-seat instrument panel 1600 may be spaced and / or separated (e.g., spaced apart or separated) from instrument panel 1400, and center console 1500 may be disposed between instrument panel 1400 and passenger-seat instrument panel 1600. In one or more embodiments, instrument panel 1400 may be disposed corresponding to the driver's seat, and passenger-seat instrument panel 1600 may be disposed corresponding to the passenger seat. In one or more embodiments, instrument panel 1400 may be adjacent to first side window glass 1110, and passenger-seat instrument panel 1600 may be adjacent to second side window glass 1120.

[0640] In one or more embodiments, 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 arranged inside the vehicle 1000. In one or more embodiments, the display device 2 may be arranged between the side windows 1100 that are opposite to each other (e.g., facing each other). The display device 2 may be arranged on at least one of the instrument panel 1400, the center console 1500, and the passenger seat instrument panel 1600.

[0641] The display device 2 may include an organic light-emitting display device, an inorganic electroluminescent display device, and / or a quantum dot display device, etc. Hereinafter, as the display device 2 according to one or more embodiments, an organic light-emitting display device including a light-emitting device according to the present disclosure will be described as an example, but one or more appropriate types (kinds) of display devices as described above may be used in the embodiments.

[0642] refer to Figure 8A In one or more embodiments, the display device 2 may be disposed on the center console 1500. In one or more embodiments, the display device 2 may display navigation information. In one or more embodiments, the display device 2 may display information regarding audio settings, video settings, or vehicle settings.

[0643] refer to Figure 8B In one or more embodiments, the display device 2 may be disposed on the instrument panel 1400. In these embodiments, the instrument panel 1400 may display driving information, etc., via the display device 2. For example, the instrument panel 1400 may digitally display driving information, etc. In one or more embodiments, the instrument panel 1400 may digitally display vehicle information and driving information as images. For example, the tachometer needle and gauge, as well as one or more appropriate warning light icons, may be displayed via digital signals.

[0644] refer to Figure 8CIn one or more embodiments, the display device 2 may be disposed on the passenger seat instrument panel 1600. The display device 2 may be embedded in the passenger seat instrument panel 1600 or disposed on the passenger seat instrument panel 1600. In one or more embodiments, the display device 2 disposed on the passenger seat instrument panel 1600 may display images related to the information displayed on the instrument panel 1400 and / or the information displayed on the center console 1500. In one or more embodiments, the display device 2 disposed on the passenger seat instrument panel 1600 may display information different from the information displayed on the instrument panel 1400 and / or the information displayed on the center console 1500.

[0645] Manufacturing method

[0646] A layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region can each be formed in a specific region by using one or more appropriate methods (such as vacuum deposition, spin coating, casting, Langmuir-Brockett (LB) deposition, inkjet printing, laser printing, and / or laser induced thermal imaging, etc.).

[0647] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are each formed by vacuum deposition, the deposition may be performed at a deposition temperature in the range of about 100° C. to about 500° C., at a temperature in the range of about 10° C. to about 500° C., or at a temperature in the range of about 10° C. to about 500° C. depending on the materials included in the layers to be formed and the structures of the layers to be formed. -8 About 10 -3 The vacuum degree is about 1000 torr and the range is about / second to about / s deposition rate.

[0648] Definition of terms

[0649] As used herein, the term "C3-C 60 "Carbocyclyl" refers to a cyclic group that includes (e.g., consists of) carbon atoms as the only ring-forming atoms and has 3 to 60 carbon atoms, for example, C3-C 50 Carbocyclic group, C3-C 40 Carbocyclic group, C3-C 30 Carbocyclic group, C3-C 20 Carbocyclic or C3-C 10 Carbocyclic groups, and as used herein, the term "C1-C 60 The "heterocyclic group" refers to a cyclic group having 1 to 60 carbon atoms and further including heteroatoms as ring atoms in addition to carbon atoms, for example, C1-C 50 Heterocyclic group, C1-C 40 Heterocyclic group, C1-C 30 Heterocyclic group, C1-C 20 Heterocyclic or C1-C 10Heterocyclic group. C3-C 60 Carbocyclic and C1-C 60 The heterocyclic groups may each be: a monocyclic group comprising (e.g., consisting of) one (e.g., exactly one) ring; or a polycyclic group in which two or more rings are fused to each other. 60 The number of ring-forming atoms of the heterocyclic group can be 3 to 61.

[0650] As used herein, the term "cyclic group" may (for example, simultaneously) include C3-C 60 Carbocyclic and C1-C 60 Both heterocyclic groups.

[0651] As used herein, the term "π-electron-rich C3-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 C1-C 60 The term "heterocyclic group" refers to a heterocyclic group having 1 to 60 carbon atoms and including *-N=*' as a ring-forming portion.

[0652] For example,

[0653] C3-C 60 The carbocyclic group may be i) a T1 group or ii) a fused ring group in which two or more T1 groups are fused to each other (e.g., cyclopentadienyl, adamantyl, norbornyl, phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, perylenyl, pentaphenanthrenyl, heptalenyl, tetracenyl, phenanthrenyl, hexenacenyl, pentacenaphthenyl, rubenyl, coronenyl, ovalenyl, indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthrenyl, or indenoanthryl),

[0654] C1-C 60The heterocyclic group may be i) a T2 group, ii) a fused ring group in which two or more T2 groups are fused to each other, or iii) a fused ring group in which at least one T2 group and at least one T1 group are fused to each other (e.g., pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiorolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiorolyl, dibenzothiophenyl, dibenzofuranyl, indenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzothiorolocarbazolyl, benzindololcarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, benzonaphthothiorolyl, benzofuranodibenzofuran ... dibenzothiophene, benzothienodibenzothiophene, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzo quinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiazolyl, azadibenzothiophene and / or azadibenzofuranyl, etc.),

[0655] π-electron-rich C3-C 60 The cyclic group may be i) a T1 group, ii) a fused ring group in which two or more T1 groups are fused to each other, iii) a T3 group, iv) a fused ring group in which two or more T3 groups are fused to each other, or v) a fused ring group in which at least one T3 group and at least one T1 group are fused to each other (e.g., C3-C 60 carbocyclyl, 1H-pyrrolyl, thiolyl, borocyclopentadienyl, 2H-pyrrolyl, 3H-pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiolyl, benzothiolyl, benzofuranyl, carbazolyl, dibenzothiolyl, dibenzothiolyl, dibenzofuranyl, indenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothienocarbazolyl, benzothiololocarbazolyl, benzoindololocarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, benzonaphthothiolyl, benzofuranodibenzofuranyl, benzofuranodibenzothienyl and / or benzothienodibenzothienyl, etc.),

[0656] π-electron-deficient nitrogen-containing C1-C 60The heterocyclic group may be i) a T4 group, ii) a fused ring group in which two or more T4 groups are fused to each other, iii) a fused ring group in which at least one T4 group and at least one T1 group are fused to each other, iv) a fused ring group in which at least one T4 group and at least one T3 group are fused to each other, or v) a fused ring group in which at least one T4 group, at least one T1 group and at least one T3 group are fused to each other (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, , benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiazolyl, azadibenzothiophenyl and / or azadibenzofuranyl, etc.),

[0657] The T1 group can be cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornane (or bicyclo[2.2.1]heptane), norbornenyl, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane or phenyl,

[0658] The T2 group 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, tetrazinyl, pyrrolidinyl, imidazolidinyl, dihydropyrrolyl, piperidinyl, tetrahydropyridinyl, dihydropyridinyl, hexahydropyrimidinyl, tetrahydropyrimidinyl, dihydropyrimidinyl, piperazinyl, tetrahydropyrazinyl, dihydropyrazinyl, tetrahydropyridazinyl or dihydropyridazinyl,

[0659] The T3 group may be a furyl group, a thienyl group, a 1H-pyrrolyl group, a thiol group or a borocyclopentadienyl group, and

[0660] The T4 group can be 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathiazolyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl or tetrazinyl.

[0661] As used herein, the terms "cyclic group", "C3-C 60 Carbocyclic group", "C1-C 60 Heterocyclic group", "π-electron-rich C3-C 60 Cyclic groups" and "π-electron-deficient nitrogen-containing C1-C 60 The term "heterocyclic group" refers to a monovalent group or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) fused to a cyclic group (e.g., combined with a cyclic group) according to the structure of the formula using the corresponding term. For example, "phenyl" may be benzo, phenyl and / or phenylene, etc., which can be easily understood by those skilled in the art based on the structure of the formula including "phenyl".

[0662] Unit price C3-C 60 Carbocyclic groups and monovalent C1-C 60 Non-limiting examples of heterocyclic groups may include C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group, and divalent C3-C 60 Carbocyclic groups and divalent C1-C 60 Non-limiting examples of heterocyclic groups may include C3-C 10 Cycloalkylene, C1-C 10 Heterocycloalkylene, C3-C 10 Cycloalkenylene, C1-C 10 Heterocycloalkenylene, C6-C 60 Arylene, C1-C 60 heteroarylene group, a divalent non-aromatic fused polycyclic group, and a divalent non-aromatic fused heteropolycyclic group.

[0663] As used herein, the term "C1-C 60 "Alkyl" refers to a straight or branched chain aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, for example, C1-C 50 Alkyl, C1-C 30 Alkyl, C1-C 20 Alkyl or C1-C 10Alkyl, and non-limiting examples thereof may include 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 / or tert-decyl, etc. As used herein, the term “C1-C 60 "Alkylene" refers to a C1-C 60 The alkyl group has a divalent group having substantially the same structure.

[0664] As used herein, the term "C2-C 60 "Alkenyl" refers to a C2-C 60 A monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the end of the alkyl group, for example, C2-C 30 Alkenyl, C2-C 20 Alkenyl or C2-C 10 The term "C2-C4-alkenyl" as used herein may include vinyl, propenyl and / or butenyl, and non-limiting examples thereof may include vinyl, propenyl and / or butenyl, etc. 60 "Alkenylene" refers to a C2-C 60 Alkenyl groups are divalent groups having substantially the same structure.

[0665] As used herein, the term "C2-C 60 "Alkynyl" refers to a C2-C 60 The alkyl group has at least one carbon-carbon triple bond in the middle or at the end, for example, C2-C 30 Alkynyl, C2-C 20 Alkynyl or C2-C 10 Alkynyl, and non-limiting examples thereof may include ethynyl and / or propynyl, etc. As used herein, the term "C2-C 60 "Alkynylidene" refers to a C2-C 60 Alkynyl groups are divalent groups having substantially the same structure.

[0666] As used herein, the term "C1-C 60 "Alkoxy" refers to a 101 (where A 101 C1-C 60 A monovalent group represented by an alkyl group, for example, C1-C 30 Alkoxy, C1-C 20 Alkoxy or C1-C 10 Alkoxy groups, and non-limiting examples thereof may include methoxy, ethoxy, and / or isopropoxy groups, and the like.

[0667] As used herein, the term "C3-C10 The term "cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and non-limiting examples thereof may 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 / or bicyclo[2.2.2]octyl, etc. As used herein, the term "C3-C 10 "Cycloalkylene" refers to a C3-C 10 The cycloalkyl group has a divalent group having substantially the same structure.

[0668] As used herein, the term "C1-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 non-limiting examples thereof may include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and / or tetrahydrothienyl. 10 "Heterocycloalkylene" refers to a C1-C 10 The heterocycloalkyl group has a divalent group having substantially the same structure.

[0669] As used herein, the term "C3-C 10 "Cycloalkenyl" refers to a monovalent cyclic group having 3 to 10 carbon atoms, having at least one carbon-carbon double bond in its ring, and having no aromaticity, and non-limiting examples thereof may include cyclopentenyl, cyclohexenyl and / or cycloheptenyl, etc. The term "C3-C 10 "Cycloalkenylene" refers to a C3-C 10 The cycloalkenyl group is a divalent group having substantially the same structure.

[0670] As used herein, the term "C1-C 10 The term "heterocycloalkenyl" refers to a monovalent cyclic group having 1 to 10 carbon atoms, which further includes at least one heteroatom as a ring-forming atom in addition to carbon atoms and has at least one double bond in its ring. 10 Non-limiting examples of heterocycloalkenyl groups may include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl and / or 2,3-dihydrothienyl, etc. As used herein, the term "C1-C 10 "Heterocycloalkenylene" refers to a C1-C 10 The heterocycloalkenyl group is a divalent group having substantially the same structure.

[0671] As used herein, the term "C6-C 60 "Aryl" refers to a monovalent radical of a carbocyclic aromatic system having 6 to 60 carbon atoms, for example, C6-C 50Aryl, C6-C 40 Aryl, C6-C 30 Aryl, C6-C 20 Aryl or C6-C 15 Aryl, and as used herein the term "C6-C 60 "Arylene" refers to a divalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. 60 Non-limiting examples of aryl groups may include phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, perylenyl, pentaphenanyl, heptalenyl, tetracenyl, pyrenyl, hexenyl, pentacenyl, rubenyl, corundum and / or ovalenyl, etc. When C6-C 60 Aryl and C6-C 60 When the arylene groups each include two or more rings, the two or more rings may be fused to each other.

[0672] As used herein, the term "C1-C 60 "Heteroaryl" refers to a monovalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms and further including at least one heteroatom as a ring atom in addition to carbon atoms, for example, C1-C 50 Heteroaryl, C1-C 40 Heteroaryl, C1-C 30 Heteroaryl, C1-C 20 Heteroaryl or C1-C 10 Heteroaryl. As used herein, the term "C1-C 60 "Heteroarylene" refers to a divalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms and further including at least one heteroatom as a ring atom in addition to carbon atoms. 60 Non-limiting examples of heteroaryl groups may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl and / or naphthyridinyl, etc. When C1-C 60 Heteroaryl and C1-C 60 When the heteroarylene groups each include two or more rings, the two or more rings may be fused to each other.

[0673] As used herein, the term "monovalent non-aromatic fused polycyclic group" refers to a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings fused to each other, having only carbon atoms as ring atoms, and having no aromaticity in its entire molecular structure as a whole, for example, C8-C 60 Monovalent non-aromatic fused polycyclic group, C8-C 50Monovalent non-aromatic fused polycyclic group, C8-C 40 Monovalent non-aromatic fused polycyclic group, C8-C 30 Monovalent non-aromatic fused polycyclic group or C8-C 20 Monovalent non-aromatic fused polycyclic group. Non-limiting examples of the monovalent non-aromatic fused polycyclic group may include indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl and / or indenoanthryl, etc. As used herein, the term "divalent non-aromatic fused polycyclic group" refers to a divalent group having substantially the same structure as the monovalent non-aromatic fused polycyclic group.

[0674] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (e.g., having 1 to 60 carbon atoms) 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, and having no aromaticity in its entire molecular structure as a whole, for example, C1-C 60 Monovalent non-aromatic fused heteropolycyclic group, C1-C 50 Monovalent non-aromatic fused heteropolycyclic group, C1-C 40 Monovalent non-aromatic fused heteropolycyclic group, C1-C 30 Monovalent non-aromatic fused heteropolycyclic group or C1-C 20 Monovalent non-aromatic fused heteropolycyclic groups. Non-limiting examples of the monovalent non-aromatic fused heteropolycyclic groups may include pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiorolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiorolyl, dibenzothiophenyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzothiorolyl, azadibenzothiophenyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazole 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.

[0675] As used herein, the term "C6-C 60 "Aryloxy" refers to -OA 102(where A 102 C6-C 60 Aryl), for example, C6-C 50 Aryloxy, C6-C 40 Aryloxy, C6-C 30 Aryloxy, C6-C 20 Aryloxy or C6-C 15 Aryloxy, and as used herein the term "C6-C 60 "Arylthio" refers to -SA 103 (where A 103 C6-C 60 Aryl), for example, C6-C 50 Arylthio, C6-C 40 Arylthio, C6-C 30 Arylthio, C6-C 20 Arylthio or C6-C 15 Arylthio.

[0676] As used herein, the term "C7-C 60 "Aralkyl" refers to -A 104 A 105 (where A 104 C1-C 54 Alkylene, and A 105 C6-C 59 aryl), for example, C7-C 50 Aralkyl, C7-C 40 Aralkyl, C7-C 30 Aralkyl, C7-C 20 Arylalkyl or C7-C 15 Aralkyl, and as used herein the term "C2-C 60 "Heteroaralkyl" refers to -A 106 A 107 (where A 106 C1-C 59 Alkylene, and A 107 C1-C 59 heteroaryl), for example, C2-C 50 Heteroarylalkyl, C2-C 40 Heteroarylalkyl, C2-C 30 Heteroarylalkyl, C2-C 20 Heteroarylalkyl or C2-C 15 Heteroaralkyl.

[0677] As used herein, the term "R 10a " can be:

[0678] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, or nitro;

[0679] 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, 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;

[0680] Each unsubstituted or substituted C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroarylalkyl: 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)(Q21 )、-S(=O)2(Q 21 ),-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or

[0681] -O(Q 31 )、-S(Q 31 )、-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 ).

[0682] As used herein, Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each of them can be independently: 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; each unsubstituted or deuterated, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C substituted by alkoxy, phenyl, biphenyl or any combination thereof 60 Carbocyclic or C1-C 60 Heterocyclic group; C7-C 60 Aralkyl; or C2-C 60 Heteroaralkyl.

[0683] As used herein, the term "heteroatom" refers to any atom other than carbon and hydrogen atoms. Non-limiting examples of heteroatoms may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.

[0684] The term “transition metal” as used herein may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), and / or gold (Au), among others.

[0685] The term "Ph" as used herein refers to a phenyl group, the term "Me" as used herein refers to a methyl group, the term "Et" as used herein refers to an ethyl group, the term "tert-Bu" or "Bu" as used herein refers to an ethyl group. t ” refers to a tert-butyl group, and the term “OMe” as used herein refers to a methoxy group.

[0686] As used herein, the term "biphenyl" refers to a "phenyl group substituted by a phenyl group". For example, a "biphenyl group" may be a group having C6-C 60 A phenyl group substituted with an aryl group as a substituent.

[0687] As used herein, the term "terphenyl" refers to a "phenyl group substituted by a biphenyl group". For example, a "terphenyl" may be a group having a C6-C 60 Aryl-substituted C6-C 60 A phenyl group substituted with an aryl group as a substituent.

[0688] Unless otherwise defined, * and *' as used herein each refer to a bonding site to the adjacent atom in the corresponding formula or moiety.

[0689] The terms "x-axis," "y-axis," and "z-axis" as used herein are not limited to the three axes in an orthogonal coordinate system (e.g., a Cartesian coordinate system), and may be interpreted in a broader sense than the three axes in the aforementioned orthogonal coordinate system. For example, the x-axis, y-axis, and z-axis may describe axes that are orthogonal to each other, or may describe axes in different directions that are not orthogonal to each other.

[0690] In the specification, “an integer selected from 0 to 20” refers to an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 and 20. The description of the above numerical range is also applicable to any other numerical range appearing in the specification, for example, an integer selected from 0 and 1, an integer selected from 0 to 2, an integer selected from 0 to 3, an integer selected from 0 to 4, an integer selected from 0 to 5, an integer selected from 0 to 6, an integer selected from 0 to 7, an integer selected from 0 to 8, an integer selected from 0 to 9, an integer selected from 0 to 10, an integer selected from 0 to 11, an integer selected from 0 to 12, an integer selected from 0 to 13, an integer selected from 0 to 14, an integer selected from 0 to 15, an integer selected from 0 to 16, an integer selected from 0 to 17, an integer selected from 0 to 18 and an integer selected from 0 to 19, etc.

[0691] Hereinafter, heterocyclic compounds represented by Formula 1 according to one or more embodiments and light-emitting devices according to one or more embodiments will be described in more detail with reference to synthesis examples and examples. The phrase "using B instead of A" used in describing a synthesis example means using substantially the same molar equivalent of B instead of A.

[0692] Example

[0693] Synthesis Example 1: Synthesis of Compound 1

[0694]

[0695] Synthesis of intermediate compound 1-1

[0696] Tetrahydrofuran (THF) is added to 4-bromo-1-chloro-2-methylbenzene (1.0 equivalents), and the resulting reaction solution is cooled to -78 ° C. N-butyl lithium (1.05 equivalents) is slowly added dropwise to the reaction solution under a nitrogen atmosphere, followed by stirring at -78 ° C for 1 hour. Cyclohexanone (1.1 equivalents) dissolved in THF is slowly added dropwise to the reaction solution at -78 ° C, followed by stirring at room temperature for 4 hours. The reaction product is then rinsed three times with ethyl acetate and water (e.g., 1) The reaction mixture is combined with ethyl acetate (organic solvent) and water. This produces two layers: an organic layer (containing ethyl acetate and the desired product) and an aqueous layer (containing water and water-soluble impurities); 2) the two layers are separated. The organic layer containing the product was retained, while the aqueous layer containing water-soluble impurities was discarded; and 3) this rinsing process was repeated three times to ensure that as much water-soluble impurities as possible were removed from the organic layer), and the resulting organic layer was first dried with MgSO4 (desiccant) and then dried again under reduced pressure. Intermediate compound 1-1 was obtained by column chromatography (yield: 67%).

[0697] Synthesis of intermediate compound 1-2

[0698] Anisole was added to intermediate compound 1-1 (1.0 equivalents), and the resulting reaction solution was cooled to 0°C. Trifluoroacetic acid (3.0 equivalents) was added dropwise to the reaction solution, followed by stirring at room temperature for 2 hours. The reaction product was then rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 1-2 was obtained by column chromatography (yield: 91%).

[0699] Synthesis of intermediate compound 1-3

[0700] Dichloromethane (DCM) is added to intermediate compound 1-2 (1.0 equivalents), and the resulting reaction solution is cooled to 0°C. Tribromoborane (5.0 equivalents) is slowly added dropwise to the reaction solution, followed by stirring at 0°C for 4 hours. Diisopropylethylamine (5.0 equivalents) is slowly added dropwise to the reaction solution at -78°C, followed by stirring at room temperature for 1 hour. Aqueous sodium bicarbonate solution is cooled to 0°C, and the reaction solution is slowly added dropwise thereto to neutralize. The reaction product is then rinsed three times with ethyl acetate and water, and the resulting organic layer is first dried with MgSO4, and then dried again under reduced pressure. Intermediate compound 1-3 (yield: 81%) is obtained by column chromatography.

[0701] Synthesis of intermediate compounds 1-4

[0702] DCM is added to intermediate compound 1-3 (1.0 equivalents), and the resulting reaction solution is cooled to 0 ° C. Diisopropylethylamine (3.0 equivalents) is added to the reaction solution, and trifluoromethanesulfonic anhydride (2.0 equivalents) is slowly added dropwise thereto at 0 ° C, followed by stirring at room temperature for 4 hours. The reaction product is then rinsed three times with ethyl acetate and water, and the resulting organic layer is first dried with MgSO4, and then dried again under reduced pressure. Intermediate compound 1-4 (yield: 85%) is obtained by column chromatography.

[0703] Synthesis of intermediate compound 1-5

[0704] Intermediate compound 1-4 (1.0 equivalent), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (1.2 equivalents), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (0.05 equivalents) and potassium acetate (3.0 equivalents) were dissolved in 1,4-dioxane, and the resulting reaction solution was stirred at 100°C for 12 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 1-5 was obtained by column chromatography (yield: 72%).

[0705] Synthesis of intermediate compound 1-6

[0706] Intermediate compound 1-5 (1.0 equivalent), 4-bromobenzonitrile (1.1 equivalent), bis(triphenylphosphine)palladium dichloride (II) (0.02 equivalent) and potassium carbonate (2.0 equivalent) were dissolved in a solution containing toluene, EtOH and H2O in a volume ratio of 4:1:1, and the resulting reaction solution was stirred at 100°C for 5 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 1-6 was obtained by column chromatography (yield: 74%).

[0707] Synthesis of intermediate compound 1-7

[0708] Intermediate compound 1-6 (1.0 equivalent), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (1.2 equivalent), palladium acetate (II) (0.05 equivalent), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (Sphos) (0.06 equivalent) and potassium acetate (3.0 equivalent) were dissolved in xylene, and the resulting reaction solution was stirred at 100 ° C for 12 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4, and then dried again under reduced pressure. Intermediate compound 1-7 (yield: 52%) was obtained by column chromatography.

[0709] Synthesis of compound 1

[0710] The intermediate compound 1-7 (1.0 equivalent), 2-chloro-4,6-diphenyl-1,3,5-triazine (1.2 equivalents), tetrakis(triphenylphosphine)palladium (0.05 equivalents) and potassium carbonate (2.0 equivalents) were dissolved in a solution of toluene, EtOH and H2O containing a volume ratio of 4:1:1, and the resulting reaction solution was stirred at 100 ° C for 5 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Compound 1 was obtained by column chromatography (yield: 80%). By fast atom bombardment mass spectrometry (FAB-MS), a molecular ion peak of mass number m / z=582.28 was observed. Therefore, compound 1 was identified.

[0711] Synthesis Example 2: Synthesis of Compound 3

[0712]

[0713] Synthesis of intermediate compound 3-1

[0714] THF is added to 1-bromo-4-chloro-2-methylbenzene (1.0 equivalents), and the resulting reaction solution is cooled to -78 ° C. Under a nitrogen atmosphere, N-butyl lithium (1.05 equivalents) is slowly added dropwise to the reaction solution, followed by stirring at -78 ° C for 1 hour. At -78 ° C, cyclohexanone (1.1 equivalents) dissolved in THF is slowly added dropwise to the reaction solution, followed by stirring at room temperature for 4 hours. Then, the reaction product is rinsed three times with ethyl acetate and water, and the resulting organic layer is first dried with MgSO 4, and then dried again under reduced pressure. Intermediate compound 3-1 (yield: 60%) is obtained by column chromatography.

[0715] Synthesis of intermediate compound 3-2

[0716] Anisole was added to the intermediate compound 3-1 (1.0 equivalents), and the resulting reaction solution was cooled to 0°C. Trifluoroacetic acid (3.0 equivalents) was added dropwise to the reaction solution, followed by stirring at room temperature for 2 hours. The reaction product was then rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 3-2 was obtained by column chromatography (yield: 90%).

[0717] Synthesis of intermediate compound 3-3

[0718] DCM is added to intermediate compound 3-2 (1.0 equivalents), and the resulting reaction solution is cooled to 0 ° C. Tribromoborane (5.0 equivalents) is slowly added dropwise to the reaction solution, followed by stirring at 0 ° C for 4 hours. Diisopropylethylamine (5.0 equivalents) is slowly added dropwise to the reaction solution at -78 ° C, followed by stirring at room temperature for 1 hour. Sodium bicarbonate aqueous solution is cooled to 0 ° C, and the reaction solution is slowly added dropwise thereto to neutralize. The reaction product is then rinsed three times with ethyl acetate and water, and the resulting organic layer is first dried with MgSO4, and then dried again under reduced pressure. Intermediate compound 3-3 (yield: 83%) is obtained by column chromatography.

[0719] Synthesis of intermediate compound 3-4

[0720] DCM is added to intermediate compound 3-3 (1.0 equivalents), and the resulting reaction solution is cooled to 0 ° C. Diisopropylethylamine (3.0 equivalents) is added to the reaction solution, and trifluoromethanesulfonic anhydride (2.0 equivalents) is slowly added dropwise thereto at 0 ° C, followed by stirring at room temperature for 4 hours. The reaction product is then rinsed three times with ethyl acetate and water, and the resulting organic layer is first dried with MgSO4, and then dried again under reduced pressure. Intermediate compound 3-4 (yield: 88%) is obtained by column chromatography.

[0721] Synthesis of intermediate compound 3-5

[0722] The intermediate compound 3-4 (1.0 equivalent), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (1.2 equivalents), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (0.05 equivalents) and potassium acetate (3.0 equivalents) were dissolved in 1,4-dioxane, and the resulting reaction solution was stirred at 100 ° C for 12 hours under a nitrogen atmosphere. After cooling, the reaction product was washed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 3-5 was obtained by column chromatography (yield: 80%).

[0723] Synthesis of intermediate compound 3-6

[0724] The intermediate compound 3-5 (1.0 equivalent), 4-bromobenzonitrile (1.1 equivalent), bis(triphenylphosphine)palladium dichloride (II) (0.02 equivalent) and potassium carbonate (2.0 equivalent) were dissolved in a solution containing toluene, EtOH and H2O in a volume ratio of 4:1:1, and the resulting reaction solution was stirred at 100°C for 5 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 3-6 was obtained by column chromatography (yield: 71%).

[0725] Synthesis of intermediate compound 3-7

[0726] Intermediate compound 3-6 (1.0 equivalent), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (1.2 equivalent), palladium (II) acetate (0.05 equivalent), Sphos (0.06 equivalent) and potassium acetate (3.0 equivalent) were dissolved in xylene, and the resulting reaction solution was stirred at 100 ° C for 12 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 3-7 (yield: 50%) was obtained by column chromatography.

[0727] Synthesis of compound 3

[0728] The intermediate compound 3-7 (1.0 equivalent), 2-chloro-4,6-diphenyl-1,3,5-triazine (1.2 equivalents), tetrakis(triphenylphosphine)palladium (0.05 equivalents) and potassium carbonate (2.0 equivalents) were dissolved in a solution of toluene, EtOH and H2O containing a volume ratio of 4:1:1, and the resulting reaction solution was stirred at 100 ° C for 5 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Compound 3 was obtained by column chromatography (yield: 77%). By FAB-MS, a molecular ion peak of mass number m / z=582.28 was observed. Therefore, compound 3 was identified.

[0729] Synthesis Example 3: Synthesis of Compound 16

[0730]

[0731] Synthesis of intermediate compound 16-1

[0732] THF is added to 2-bromo-6-chloronaphthalene (1.0 equivalents), and the resulting reaction solution is cooled to -78 ° C. Under a nitrogen atmosphere, N-butyl lithium (1.05 equivalents) is slowly added dropwise to the reaction solution, followed by stirring at -78 ° C for 1 hour. At -78 ° C, cyclohexanone (1.1 equivalents) dissolved in THF is slowly added dropwise to the reaction solution, followed by stirring at room temperature for 4 hours. Then, the reaction product is rinsed three times with ethyl acetate and water, and the resulting organic layer is first dried with MgSO 4, and then dried again under reduced pressure. Intermediate compound 16-1 (yield: 67%) is obtained by column chromatography.

[0733] Synthesis of intermediate compound 16-2

[0734] Anisole was added to the intermediate compound 16-1 (1.0 equivalents), and the resulting reaction solution was cooled to 0°C. Trifluoroacetic acid (3.0 equivalents) was added dropwise to the reaction solution, followed by stirring at room temperature for 2 hours. The reaction product was then rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 16-2 was obtained by column chromatography (yield: 80%).

[0735] Synthesis of intermediate compound 16-3

[0736] DCM is added to intermediate compound 16-2 (1.0 equivalents), and the resulting reaction solution is cooled to 0 ° C. Tribromoborane (5.0 equivalents) is slowly added dropwise to the reaction solution, followed by stirring at 0 ° C for 4 hours. Diisopropylethylamine (5.0 equivalents) is slowly added dropwise to the reaction solution at -78 ° C, followed by stirring at room temperature for 1 hour. Sodium bicarbonate aqueous solution is cooled to 0 ° C, and the reaction solution is slowly added dropwise thereto to neutralize. The reaction product is then rinsed three times with ethyl acetate and water, and the resulting organic layer is first dried with MgSO4, and then dried again under reduced pressure. Intermediate compound 16-3 (yield: 85%) is obtained by column chromatography.

[0737] Synthesis of intermediate compound 16-4

[0738] DCM is added to intermediate compound 16-3 (1.0 equivalents), and the resulting reaction solution is cooled to 0 ° C. Diisopropylethylamine (3.0 equivalents) is added to the reaction solution, and trifluoromethanesulfonic anhydride (2.0 equivalents) is slowly added dropwise thereto at 0 ° C, followed by stirring at room temperature for 4 hours. The reaction product is then rinsed three times with ethyl acetate and water, and the resulting organic layer is first dried with MgSO4, and then dried again under reduced pressure. Intermediate compound 16-4 (yield: 87%) is obtained by column chromatography.

[0739] Synthesis of intermediate compound 16-5

[0740] The intermediate compound 16-4 (1.0 equivalent), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (1.2 equivalents), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (0.05 equivalents) and potassium acetate (3.0 equivalents) were dissolved in 1,4-dioxane, and the resulting reaction solution was stirred at 100 ° C for 12 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 16-5 was obtained by column chromatography (yield: 82%).

[0741] Synthesis of intermediate compound 16-6

[0742] The intermediate compound 16-5 (1.0 equivalent), 4-bromobenzonitrile (1.1 equivalent), bis(triphenylphosphine)palladium dichloride (II) (0.02 equivalent) and potassium carbonate (2.0 equivalent) were dissolved in a solution containing toluene, EtOH and H2O in a volume ratio of 4:1:1, and the resulting reaction solution was stirred at 100°C for 5 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 16-6 was obtained by column chromatography (yield: 72%).

[0743] Synthesis of intermediate compound 16-7

[0744] Intermediate compound 16-6 (1.0 equivalent), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (1.2 equivalent), palladium (II) acetate (0.05 equivalent), Sphos (0.06 equivalent) and potassium acetate (3.0 equivalent) were dissolved in xylene, and the resulting reaction solution was stirred at 100 ° C for 12 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 16-7 (yield: 55%) was obtained by column chromatography.

[0745] Synthesis of compound 16

[0746] Compound intermediate 16-7 (1.0 equivalent), 2-chloro-4,6-diphenyl-1,3,5-triazine (1.2 equivalents), tetrakis(triphenylphosphine)palladium (0.05 equivalents) and potassium carbonate (2.0 equivalents) were dissolved in a solution of toluene, EtOH and H2O containing a volume ratio of 4:1:1, and the resulting reaction solution was stirred at 100 ° C for 5 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Compound 16 (yield: 84%) was obtained by column chromatography. By FAB-MS, a molecular ion peak of mass number m / z=618.28 was observed. Therefore, compound 16 was identified.

[0747] Synthesis Example 4: Synthesis of Compound 17

[0748]

[0749] Synthesis of intermediate compound 17-1

[0750] The intermediate compound 16-5 (1.0 equivalent), 2-chloro-4,6-diphenyl-1,3,5-triazine (1.1 equivalent), bis(triphenylphosphine)palladium dichloride (II) (0.02 equivalent) and potassium carbonate (2.0 equivalent) were dissolved in a solution containing toluene, EtOH and H2O in a volume ratio of 4:1:1, and the resulting reaction solution was stirred at 100 ° C for 5 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 17-1 was obtained by column chromatography (yield: 75%).

[0751] Synthesis of intermediate compound 17-2

[0752] The intermediate compound 17-1 (1.0 equivalent), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (1.2 equivalents), palladium (II) acetate (0.05 equivalents), Sphos (0.06 equivalents) and potassium acetate (3.0 equivalents) were dissolved in xylene, and the resulting reaction solution was stirred at 100 ° C for 12 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 17-2 (yield: 65%) was obtained by column chromatography.

[0753] Synthesis of compound 17

[0754] The intermediate compound 17-2 (1.0 equivalent), 4-bromobenzonitrile (1.2 equivalents), tetrakis(triphenylphosphine)palladium (0.05 equivalents) and potassium carbonate (2.0 equivalents) were dissolved in a solution of toluene, EtOH and H2O containing a volume ratio of 4:1:1, and the resulting reaction solution was stirred at 100°C for 5 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Compound 17 (yield: 84%) was obtained by column chromatography. By FAB-MS, a molecular ion peak of mass number m / z=618.28 was observed. Therefore, compound 17 was identified.

[0755] Synthesis Example 5: Synthesis of Compound 21

[0756]

[0757] Synthesis of intermediate compound 21-1

[0758] THF is added to 3-bromo-2-chloro-6-iodonaphthalene (1.0 equivalents), and the resulting reaction solution is cooled to -78 ° C. Under a nitrogen atmosphere, N-butyllithium (1.05 equivalents) is slowly added dropwise to the reaction solution, followed by stirring at -78 ° C for 1 hour. At -78 ° C, cyclohexanone (1.1 equivalents) dissolved in THF is slowly added dropwise to the reaction solution, followed by stirring at room temperature for 4 hours. Then, the reaction product is rinsed three times with ethyl acetate and water, and the resulting organic layer is first dried with MgSO4, and then dried again under reduced pressure. Intermediate compound 21-1 (yield: 77%) is obtained by column chromatography.

[0759] Synthesis of intermediate compound 21-2

[0760] Anisole was added to the intermediate compound 21-1 (1.0 equivalents), and the resulting reaction solution was cooled to 0 ° C. Trifluoroacetic acid (3.0 equivalents) was added dropwise to the reaction solution, followed by stirring at room temperature for 2 hours. The reaction product was then rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 21-2 was obtained by column chromatography (yield: 91%).

[0761] Synthesis of intermediate compound 21-3

[0762] The intermediate compound 21-2 (1.0 equivalent), phenylboronic acid (1.1 equivalent), bis(triphenylphosphine)palladium dichloride (II) (0.02 equivalent) and potassium carbonate (2.0 equivalent) were dissolved in a solution containing toluene, EtOH and H2O in a volume ratio of 4:1:1, and the resulting reaction solution was stirred at 100 ° C for 5 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 21-3 was obtained by column chromatography (yield: 74%).

[0763] Synthesis of intermediate compound 21-4

[0764] DCM is added to intermediate compound 21-3 (1.0 equivalents), and the resulting reaction solution is cooled to 0 ° C. Tribromoborane (5.0 equivalents) is slowly added dropwise to the reaction solution, followed by stirring at 0 ° C for 4 hours. Diisopropylethylamine (5.0 equivalents) is slowly added dropwise to the reaction solution at -78 ° C, followed by stirring at room temperature for 1 hour. Sodium bicarbonate aqueous solution is cooled to 0 ° C, and the reaction solution is slowly added dropwise thereto to neutralize. The reaction product is then rinsed three times with ethyl acetate and water, and the resulting organic layer is first dried with MgSO4, and then dried again under reduced pressure. Intermediate compound 21-4 (yield: 81%) is obtained by column chromatography.

[0765] Synthesis of intermediate compound 21-5

[0766] DCM is added to intermediate compound 21-4 (1.0 equivalents), and the resulting reaction solution is cooled to 0 ° C. Diisopropylethylamine (3.0 equivalents) is added to the reaction solution, and trifluoromethanesulfonic anhydride (2.0 equivalents) is slowly added dropwise thereto at 0 ° C, followed by stirring at room temperature for 4 hours. The reaction product is then rinsed three times with ethyl acetate and water, and the resulting organic layer is first dried with MgSO4, and then dried again under reduced pressure. Intermediate compound 21-5 (yield: 85%) is obtained by column chromatography.

[0767] Synthesis of intermediate compound 21-6

[0768] The intermediate compound 21-5 (1.0 equivalent), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (1.2 equivalents), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (0.05 equivalents) and potassium acetate (3.0 equivalents) were dissolved in 1,4-dioxane, and the resulting reaction solution was stirred at 100 ° C for 12 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 21-6 was obtained by column chromatography (yield: 72%).

[0769] Synthesis of intermediate compound 21-7

[0770] The intermediate compound 21-6 (1.0 equivalent), 2-chloro-4,6-diphenyl-1,3,5-triazine (1.1 equivalent), bis(triphenylphosphine)palladium dichloride (II) (0.02 equivalent) and potassium carbonate (2.0 equivalent) were dissolved in a solution containing toluene, EtOH and H2O in a volume ratio of 4:1:1, and the resulting reaction solution was stirred at 100 ° C for 5 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 21-7 (yield: 74%) was obtained by column chromatography.

[0771] Synthesis of intermediate compound 21-8

[0772] Intermediate compound 21-7 (1.0 equivalent), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (1.2 equivalent), palladium (II) acetate (0.05 equivalent), Sphos (0.06 equivalent) and potassium acetate (3.0 equivalent) were dissolved in xylene, and the resulting reaction solution was stirred at 100 ° C for 12 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 21-8 (yield: 52%) was obtained by column chromatography.

[0773] Synthesis of compound 21

[0774] The intermediate compound 21-8 (1.0 equivalent), 4-bromobenzonitrile (1.2 equivalents), tetrakis(triphenylphosphine)palladium (0.05 equivalents) and potassium carbonate (2.0 equivalents) were dissolved in a solution of toluene, EtOH and H2O containing a volume ratio of 4:1:1, and the resulting reaction solution was stirred at 100°C for 5 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Compound 21 was obtained by column chromatography (yield: 80%). By FAB-MS, a molecular ion peak of mass number m / z=694.31 was observed. Therefore, compound 21 was identified.

[0775] Synthesis Example 6: Synthesis of Compound 22

[0776]

[0777] Synthesis of intermediate compound 22-1

[0778] THF is added to 2,7-dibromo-9,9-dimethyl-9H-fluorene (1.0 equivalents), and the resulting reaction solution is cooled to -78 ° C. N-butyl lithium (1.05 equivalents) is slowly added dropwise to the reaction solution under a nitrogen atmosphere, followed by stirring at -78 ° C for 1 hour. Cyclohexanone (1.1 equivalents) dissolved in THF is slowly added dropwise to the reaction solution at -78 ° C, followed by stirring at room temperature for 4 hours. The reaction product is then rinsed three times with ethyl acetate and water, and the resulting organic layer is first dried with MgSO4, and then dried again under reduced pressure. Intermediate compound 22-1 (yield: 67%) is obtained by column chromatography.

[0779] Synthesis of intermediate compound 22-2

[0780] Anisole was added to the intermediate compound 22-1 (1.0 equivalents), and the resulting reaction solution was cooled to 0°C. Trifluoroacetic acid (3.0 equivalents) was added dropwise to the reaction solution, followed by stirring at room temperature for 2 hours. The reaction product was then rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 22-2 was obtained by column chromatography (yield: 91%).

[0781] Synthesis of intermediate compound 22-3

[0782] Intermediate compound 22-2 (1.0 equivalent) and copper (I) cyanide (1.0 equivalent) were dissolved in dimethylformamide (DMF), and the resulting reaction solution was stirred at 160° C. for 24 hours under a nitrogen atmosphere. After cooling, the reaction product was washed three times with ethyl acetate and water, and the resulting organic layer was first dried over MgSO 4 and then dried again under reduced pressure. Intermediate compound 22-3 was obtained by column chromatography (yield: 72%).

[0783] Synthesis of intermediate compound 22-4

[0784] DCM is added to intermediate compound 22-3 (1.0 equivalents), and the resulting reaction solution is cooled to 0 ° C. Tribromoborane (5.0 equivalents) is slowly added dropwise to the reaction solution, followed by stirring at 0 ° C for 4 hours. Diisopropylethylamine (5.0 equivalents) is slowly added dropwise to the reaction solution at -78 ° C, followed by stirring at room temperature for 1 hour. Sodium bicarbonate aqueous solution is cooled to 0 ° C, and the reaction solution is slowly added dropwise thereto to neutralize. The reaction product is then rinsed three times with ethyl acetate and water, and the resulting organic layer is first dried with MgSO4, and then dried again under reduced pressure. Intermediate compound 22-4 (yield: 81%) is obtained by column chromatography.

[0785] Synthesis of intermediate compound 22-5

[0786] DCM was added to the intermediate compound 22-4 (1.0 equivalents), and the resulting reaction solution was cooled to 0 ° C. Diisopropylethylamine (3.0 equivalents) was added to the reaction solution, and trifluoromethanesulfonic anhydride (2.0 equivalents) was slowly added dropwise thereto at 0 ° C, followed by stirring at room temperature for 4 hours. The reaction product was then rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4, and then dried again under reduced pressure. Intermediate compound 22-5 (yield: 85%) was obtained by column chromatography.

[0787] Synthesis of intermediate compound 22-6

[0788] The intermediate compound 22-5 (1.0 equivalent), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (1.2 equivalents), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (0.05 equivalents) and potassium acetate (3.0 equivalents) were dissolved in 1,4-dioxane, and the resulting reaction solution was stirred at 100 ° C for 12 hours under a nitrogen atmosphere. After cooling, the reaction product was washed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 22-6 was obtained by column chromatography (yield: 72%).

[0789] Synthesis of compound 22

[0790] The intermediate compound 22-6 (1.0 equivalent), 2-chloro-4,6-diphenyl-1,3,5-triazine (1.1 equivalent), bis(triphenylphosphine)palladium dichloride (II) (0.02 equivalent) and potassium carbonate (2.0 equivalent) were dissolved in a solution of toluene, EtOH and H2O containing a volume ratio of 4:1:1, and the resulting reaction solution was stirred at 100 ° C for 5 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Compound 22 was obtained by column chromatography (yield: 74%). By FAB-MS, a molecular ion peak of mass number m / z=608.29 was observed. Therefore, compound 22 was identified.

[0791] Synthesis Example 7: Synthesis of Compound 45

[0792]

[0793] Synthesis of intermediate compound 45-1

[0794] Toluene, propane-1,3-diol (1.5 equivalents) and 4-methylbenzenesulfonic acid (1.0 equivalents) were added to (4-bromo-2-methylphenyl) (4-bromophenyl)methanone (1.0 equivalents), and the resulting reaction solution was stirred for 6 hours. The reaction product was then rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 45-1 was obtained by column chromatography (yield: 45%).

[0795] Synthesis of intermediate compound 45-2

[0796] The intermediate compound 45-1 (1.0 equivalent), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (2.5 equivalents), palladium (II) acetate (0.05 equivalents), Sphos (0.06 equivalents) and potassium acetate (3.0 equivalents) were dissolved in toluene, and the resulting reaction solution was stirred at 100 ° C for 12 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 45-2 (yield: 47%) was obtained by column chromatography.

[0797] Synthesis of intermediate compound 45-3

[0798] The intermediate compound 45-2 (1.0 equivalent), 4-bromobenzonitrile (1.2 equivalents), tetrakis(triphenylphosphine)palladium (0.05 equivalents) and potassium carbonate (2.0 equivalents) were dissolved in a solution containing toluene, EtOH and H2O in a volume ratio of 4:1:1, and the resulting reaction solution was stirred at 100°C for 5 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 45-3 was obtained by column chromatography (yield: 40%).

[0799] Synthesis of compound 45

[0800] The intermediate compound 45-3 (1.0 equivalent), 2-chloro-4,6-diphenyl-1,3,5-triazine (1.2 equivalents), tetrakis(triphenylphosphine)palladium (0.05 equivalents) and potassium carbonate (2.0 equivalents) were dissolved in a solution of toluene, EtOH and H2O containing a volume ratio of 4:1:1, and the resulting reaction solution was stirred at 100 ° C for 5 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Compound 45 (yield: 40%) was obtained by column chromatography. By FAB-MS, a molecular ion peak of mass number m / z=586.24 was observed. Therefore, compound 45 was identified.

[0801] Synthesis Example 8: Synthesis of Compound 227

[0802]

[0803] Synthesis of intermediate compound 227-1

[0804] The intermediate compound 16-5 (1.0 equivalent), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (1.1 equivalent), bis(triphenylphosphine)palladium dichloride (II) (0.02 equivalent) and potassium carbonate (2.0 equivalent) were dissolved in a solution containing toluene, EtOH and H2O in a volume ratio of 4:1:1, and the resulting reaction solution was stirred at 100 ° C for 5 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 227-1 was obtained by column chromatography (yield: 72%).

[0805] Synthesis of intermediate compound 227-2

[0806] Intermediate compound 227-1 (1.0 equivalent), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (1.2 equivalents), palladium (II) acetate (0.05 equivalents), Sphos (0.06 equivalents) and potassium acetate (3.0 equivalents) were dissolved in xylene, and the resulting reaction solution was stirred at 100 ° C for 12 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 227-2 (yield: 55%) was obtained by column chromatography.

[0807] Synthesis of compound 227

[0808] The intermediate compound 227-2 (1.0 equivalent), 4-bromobenzonitrile (1.2 equivalents), tetrakis(triphenylphosphine)palladium (0.05 equivalents) and potassium carbonate (2.0 equivalents) were dissolved in a solution of toluene, EtOH and H2O in a volume ratio of 4:1:1, and the resulting reaction solution was stirred at 100°C for 5 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Compound 227 was obtained by column chromatography (yield: 84%). By FAB-MS, a molecular ion peak with mass number m / z=694.31 was observed. Therefore, compound 227 was identified.

[0809] Synthesis Example 9: Synthesis of Compound 647

[0810]

[0811] Synthesis of intermediate compound 647-1

[0812] The intermediate compound 16-5 (1.0 equivalent), 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine (1.1 equivalent), bis(triphenylphosphine)palladium dichloride (II) (0.02 equivalent) and potassium carbonate (2.0 equivalent) were dissolved in a solution containing toluene, EtOH and H2O in a volume ratio of 4:1:1, and the resulting reaction solution was stirred at 100 ° C for 5 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 647-1 was obtained by column chromatography (yield: 72%).

[0813] Synthesis of intermediate compound 647-2

[0814] The intermediate compound 647-1 (1.0 equivalent), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (1.2 equivalents), palladium (II) acetate (0.05 equivalents), Sphos (0.06 equivalents) and potassium acetate (3.0 equivalents) were dissolved in xylene, and the resulting reaction solution was stirred at 100 ° C for 12 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 647-2 was obtained by column chromatography (yield: 55%).

[0815] Synthesis of compound 647

[0816] The intermediate compound 647-2 (1.0 equivalent), 4-bromobenzonitrile (1.2 equivalents), tetrakis(triphenylphosphine)palladium (0.05 equivalents) and potassium carbonate (2.0 equivalents) were dissolved in a solution of toluene, EtOH and H2O in a volume ratio of 4:1:1, and the resulting reaction solution was stirred at 100°C for 5 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Compound 647 (yield: 84%) was obtained by column chromatography. By FAB-MS, a molecular ion peak with mass number m / z=654.2 was observed. Therefore, compound 647 was identified.

[0817] Synthesis Example 10: Synthesis of Compound 857

[0818]

[0819] Synthesis of compound 857

[0820] The intermediate compound 17-2 (1.0 equivalent), 1-bromo-4-fluorobenzene (1.2 equivalents), tetrakis(triphenylphosphine)palladium (0.05 equivalents) and potassium carbonate (2.0 equivalents) were dissolved in a solution of toluene, EtOH and H2O containing a volume ratio of 4:1:1, and the resulting reaction solution was stirred at 100°C for 5 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Compound 857 (yield: 84%) was obtained by column chromatography. By FAB-MS, a molecular ion peak of mass number m / z=611.27 was observed. Therefore, compound 857 was identified.

[0821] Synthesis Example 11: Synthesis of Compound 1067

[0822]

[0823] Synthesis of compound 1067

[0824] The intermediate compound 17-2 (1.0 equivalent), (4-bromophenyl) dimethylphosphine oxide (1.2 equivalents), tetrakis (triphenylphosphine) palladium (0.05 equivalents) and potassium carbonate (2.0 equivalents) were dissolved in a solution of toluene, EtOH and H2O containing a volume ratio of 4:1:1, and the resulting reaction solution was stirred at 100 ° C for 5 hours under a nitrogen atmosphere. After cooling, the reaction product was rinsed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Compound 1067 (yield: 84%) was obtained by column chromatography. By FAB-MS, a molecular ion peak of mass number m / z=669.29 was observed. Therefore, compound 1067 was identified.

[0825] By referring to the synthetic routes and starting materials, those skilled in the art can easily recognize methods for synthesizing compounds other than the compounds synthesized in the synthetic examples.

[0826] Example 1

[0827] As an anode, a A glass substrate with an ITO electrode (product of Corning Incorporated) was cut into a size of 50 mm × 50 mm × 0.7 mm, sonicated with isopropyl alcohol and (then) pure water for 5 minutes each, cleaned by subjecting it to ultraviolet irradiation and ozone exposure for 30 minutes, and then mounted on a vacuum deposition apparatus.

[0828] NPD is deposited on the anode to form a A hole injection layer having a thickness of A hole transport layer having a thickness of , and CzSi is deposited on the hole transport layer to form a The emission auxiliary layer has a thickness of .

[0829] HT+ET (host), PS (phosphorescent sensitizer) and t-DABNA were co-deposited on the emission auxiliary layer in a weight ratio of 42:42:15:1 to form a The emission layer is formed by depositing TSPO1 on the emission layer to form a A hole blocking layer having a thickness of , compound 1 is deposited on the hole blocking layer to form a An electron transport layer having a thickness of , LiF is deposited on the electron transport layer to form a An electron injection layer having a thickness of A cathode with a thickness of is formed, thereby completing the manufacture of the light-emitting device.

[0830]

[0831] Examples 2 to 11 and Comparative Examples 1 to 13

[0832] Each light-emitting device was manufactured in substantially the same manner as in Example 1, except that the compounds used in forming the emission layer and the electron transport layer were changed as shown in Table 1.

[0833] Evaluation Example 1

[0834] The brightness of each of the light emitting devices manufactured in Examples 1 to 11 and Comparative Examples 1 to 13 was measured at 1,000 cd / m by using Keithley SMU 236 and a luminance meter PR650. 2 Driving voltage (V), luminous efficiency (cd / A) and device life (T 95 ) ratio, and the results are shown in Table 1. The device life (T 95 ) ratio is obtained by measuring the time taken for the luminance of each of the embodiment and the comparative example to reach 95% of the initial luminance (device life, hours (hr)), and then expressing the measured value as a relative ratio relative to the device life of comparative example 1 (which is set to 1).

[0835] Table 1

[0836]

[0837]

[0838]

[0839] It was confirmed from Table 1 that each of the light emitting devices according to Examples 1 to 11 had superior driving voltage, luminous efficiency, and device lifespan compared to the light emitting devices according to Comparative Examples 1 to 13.

[0840] According to one or more embodiments, a light-emitting device including the heterocyclic compound represented by Formula 1 of the present disclosure may have low driving voltage, high luminous efficiency, and long device life. In addition, high-quality electronic devices and consumer products may be manufactured using the light-emitting device.

[0841] In the present disclosure, it will be understood that the terms “comprise(s) / comprising,” “include(s) / including,” or “have / has / having” indicate the presence of stated features, integers, steps, operations, elements, components, and / or components, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, and / or groups thereof.

[0842] In the context of this application and unless otherwise defined, the terms "use," "using," and "used" may be considered synonymous with the terms "utilize," "utilizing," and "utilized," respectively.

[0843] Throughout this disclosure, when it is mentioned that a component (such as a layer, film, region, or plate) is placed "on" another component (such as a layer, film, region, or plate), it will be understood that it can be directly on the other component (such as a layer, film, region, or plate), or another component (such as a layer, film, region, or plate) can be interposed between them. In some embodiments, "directly on..." can mean that there are no additional layers, films, regions, plates, etc. between one component (such as a layer, film, region, plate, etc.) and another component (such as a layer, film, region, plate, etc.). For example, "directly on..." can mean that two layers or two members are disposed without using another member (such as an adhesive member) between them.

[0844] In the present disclosure, although the terms "first," "second," etc. may be used herein to describe one or more elements, components, regions, and / or layers, these elements, components, regions, and / or layers should not be limited by these terms. These terms are only used to distinguish one component from another.

[0845] As used herein, the singular forms "a," "an," "one," and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. Further, when describing embodiments of the present disclosure, the use of "may" refers to "one or more embodiments of the present disclosure."

[0846] As used herein, the terms "substantially," "about," or similar terms are used as terms of approximation, not as terms of degree, and are intended to encompass the inherent deviations in measured or calculated values ​​that one of ordinary skill in the art would recognize. As used herein, "about" is inclusive of the stated value and means within an acceptable range of deviations from the particular value as determined by one of ordinary skill in the art taking into account the measurements in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations, or within ±30%, ±20%, ±10%, or ±5% of the stated value.

[0847] Any numerical range set forth in this article is intended to include all subranges of the same numerical precision included in the range of the setting forth. For example, the range of "1.0 to 10.0" is intended to be included between the minimum value 1.0 set forth and the maximum value 10.0 set forth (and including the end value), that is, all subranges (such as, for example, 2.4 to 7.6) with a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0. Any maximum numerical limit set forth in this article is intended to include all lower numerical limits contained therein, and any minimum numerical limit set forth in this article is intended to include all higher numerical limits contained therein. Accordingly, the applicant reserves the right to amend this specification (including claims) to explicitly set forth any subrange contained in the range explicitly set forth herein.

[0848] The light-emitting devices, light-emitting devices, display devices, electronic devices, electronic devices, manufacturing equipment thereof, or any other related devices or components according to the embodiments of the present disclosure described herein may be implemented using any appropriate hardware, firmware (e.g., a dedicated integrated circuit), software, or a combination of software, firmware, and hardware. For example, the various components of the device may be formed on an integrated circuit (IC) chip or on separate IC chips. Further, the various components of the device may be implemented on a flexible printed circuit film, a tape carrier package, or a printed circuit board (PCB), or formed on a substrate. Further, the various components of the device may be processes or threads that run on one or more processors in one or more computing devices, execute computer program instructions, and interact with other system components to perform the various functions described herein. The computer program instructions are stored in a memory that can be implemented in a computing device using a standard memory device (such as, for example, a random access memory (RAM)). The computer program instructions may also be stored in other non-transient computer-readable media such as, for example, a CD-ROM or a flash drive. Furthermore, those skilled in the art will recognize that the functionality of various computing devices may be combined or integrated into a single computing device, or the functionality of a dedicated computing device may be distributed across one or more other computing devices without departing from the scope of the embodiments of the present disclosure.

[0849] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. The description of features or aspects in each embodiment should generally be considered applicable to other similar features or aspects in one or more embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those skilled in the art that one or more appropriate changes in form and details may be made therein without departing from the spirit and scope defined by the claims and their equivalents.

Claims

1. A light-emitting device, comprising: a first electrode; a second electrode opposite to the first electrode; an interlayer between the first electrode and the second electrode and including an emissive layer; and Heterocyclic compound represented by Formula 1: Wherein, in Formula 1, Formula 2A, Formula 2B and Formula 2C, X1 is C(R 11 ) or N, X2 is C(R 12 ) or N, and X3 is C(R 13 ) or N, Z1 is a group represented by any one of Formula 2A, Formula 2B and Formula 2C, Y1 is unsubstituted or replaced by at least one R 10a Substituted C1-C 30 Alkylene, unsubstituted or substituted with at least one R 10a Substituted C3-C 30 Cycloalkylene is either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocycloalkylene, wherein Y1 does not include unsubstituted or replaced by at least one R 10a substituted adamantyl groups, Ar1 to Ar3 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by 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 C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by 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 C7-C 60 Aralkyl, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2), L1 to L4 are each independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 heterocyclic group, n1 to n4 are each independently an integer selected from 0 to 4, wherein when n1 is 0, then *-(L1) n1 -*' is a single bond, when n2 is 0, then *-(L2) n2 -*' is a single bond. When n3 is 0, then *-(L3) n3 -*' is a single bond, and when n4 is 0, then *-(L4) n4 -*' is a single key, R1 and R2 are each independently deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or replaced by 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 C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by 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 C7-C 60 Aralkyl, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2), a4 and b4 are each independently an integer selected from 0 to 4, and a6 and b6 are each independently an integer selected from 0 to 6, When Z1 is a group represented by formula 2A, the sum of a4 and b4 is 1 or greater, When a4 is 2 or greater or when a6 is 2 or greater, two or more R1 are optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 30 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 heterocyclic group, When b4 is 2 or greater or when b6 is 2 or greater, two or more R2 are optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 30 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 heterocyclic group, R1 and R2 are each independently optionally bonded to L3, L4 or Ar3 to form an unsubstituted or substituted group. 10a Substituted C3-C 30 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 heterocyclic group, R 11 to R 13 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by 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 C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by at least one R 10a Substituted C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 arylthio, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2), 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, C1-C 60 Alkoxy or C1-C 60 Alkylthio: 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, 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, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroarylalkyl: 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 -O(Q 31 )、-S(Q 31 )、-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 )或-P(=O)(Q 31 )(Q 32 ), 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; C1-C 60 Alkylthio; each unsubstituted or deuterated, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, C1-C 60 C3-C substituted by alkylthio, phenyl, biphenyl or any combination thereof 60 Carbocyclic or C1-C 60 Heterocyclic group; C7-C 60 Aralkyl; or C2-C 60 heteroarylalkyl, and * and *' each indicate a bonding site to an adjacent atom.

2. An electronic device comprising the light emitting device according to claim 1.

3. An electronic device comprising the light emitting device according to claim 1.

4. A heterocyclic compound represented by Formula 1: in, In Formula 1, Formula 2A, Formula 2B, and Formula 2C, X1 is C(R 11 ) or N, X2 is C(R 12 ) or N, and X3 is C(R 13 ) or N, Z1 is a group represented by any one selected from Formula 2A, Formula 2B and Formula 2C, Y1 is unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Alkylene, unsubstituted or substituted with at least one R 10a Substituted C3-C 30 Cycloalkylene is either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocycloalkylene, wherein Y1 does not include unsubstituted or replaced by at least one R 10a substituted adamantyl groups, Ar1 to Ar3 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by 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 C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by 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 C7-C 60 Aralkyl, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2), L1 to L4 are each independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 heterocyclic group, n1 to n4 are each independently an integer selected from 0 to 4, wherein when n1 is 0, then *-(L1) n1 -*' is a single bond, when n2 is 0, then *-(L2) n2 -*' is a single bond. When n3 is 0, then *-(L3) n3 -*' is a single bond, and when n4 is 0, then *-(L4) n4 -*' is a single key, R1 and R2 are each independently deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or replaced by 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 C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by 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 C7-C 60 Aralkyl, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2), a4 and b4 are each independently an integer selected from 0 to 4, and a6 and b6 are each independently an integer selected from 0 to 6, When Z1 is a group represented by formula 2A, the sum of a4 and b4 is 1 or greater, When a4 is 2 or greater or when a6 is 2 or greater, two or more R1 are optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 30 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 heterocyclic group, When b4 is 2 or greater or when b6 is 2 or greater, two or more R2 are optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 30 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 heterocyclic group, R1 and R2 are each independently optionally bonded to L3, L4 or Ar3 to form an unsubstituted or substituted group. 10a Substituted C3-C 30 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 heterocyclic group, R 11 to R 13 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by 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 C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by at least one R 10a Substituted C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 arylthio, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2), 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, C1-C 60 Alkoxy or C1-C 60 Alkylthio: 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, 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, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroarylalkyl: 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 -O(Q 31 )、-S(Q 31 )、-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 )或-P(=O)(Q 31 )(Q 32 ), 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; C1-C 60 Alkylthio; each unsubstituted or deuterated, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, C1-C 60 C3-C substituted by alkylthio, phenyl, biphenyl or any combination thereof 60 Carbocyclic or C1-C 60 Heterocyclic group; C7-C 60 Aralkyl; or C2-C 60 heteroarylalkyl, and * and *' each indicate a bonding site to an adjacent atom. The heterocyclic compound according to claim 4 , wherein at least two selected from X 1 to X 3 are each N.

6. The heterocyclic compound according to claim 4, wherein Y1 is unsubstituted or substituted by at least one R 10a Substituted C1-C 10 The alkylene group is a group represented by any one selected from Formula 3-1 to Formula 3-15: In formula 3-1 to formula 3-15, R 10a Same as defined in Formula 1, c6 is an integer selected from 0 to 6, c10 is an integer selected from 0 to 10, and * and *' each indicate a bonding site to an adjacent atom.

7. The heterocyclic compound according to claim 4, wherein Ar1 to Ar3 are each independently a group represented by any one selected from Formula 4-1 to Formula 4-6: In formulas 4-1 to 4-6, R 10a Same as defined in Formula 1, d4 is an integer selected from 0 to 4, d5 is an integer selected from 0 to 5, d7 is an integer selected from 0 to 7, and *Indicates the bonding site to the adjacent atom.

8. The heterocyclic compound according to claim 4, wherein L1 to L4 are each independently unsubstituted or replaced by at least one R 10a Substituted phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, cyclopentadienyl, furanyl, thienyl, thiaryl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzothiaryl, dibenzothiaryl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothiaryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phthalazinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl oxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, dibenzooxasilanyl, dibenzothiasilanyl, dibenzodihydroazasilanyl, dibenzodihydrodisilazane, dibenzodihydrosilanyl, dibenzodioxane, dibenzooxathiasilanyl, dibenzoxazinyl, dibenzopyranyl, dibenzodithiazinyl, dibenzothiopyranyl, dibenzocyclohexadienyl, dibenzodihydropyridinyl or dibenzodihydropyrazinyl.

9. The heterocyclic compound according to claim 4, wherein R1 and R2 are each independently: Deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy or C1-C 20 alkylthio; C1-C 20 Alkyl, C1-C 20 Alkoxy or C1-C 20 Alkylthio: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, or any combination thereof; each unsubstituted or substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, phthalazinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl , benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, phthalazinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 ),-P(=O)(Q 31 )(Q 32 ) or any combination thereof; or -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), or -P(=O)(Q1)(Q2), and Q1 to Q3 and Q 31 To Q 33 Each independently represents: hydrogen; deuterium; -F; -Cl; -Br; -I; cyano; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 Alkoxy; C1-C 60 Alkylthio; C1-C 60 Alkylthio; each unsubstituted or deuterated, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C1-C 60 C3-C substituted by alkylthio, phenyl, biphenyl or any combination thereof 60 Carbocyclic or C1-C 60 Heterocyclic group; C7-C 60 Aralkyl; or C2-C 60 Heteroaralkyl.

10. The heterocyclic compound according to claim 4, wherein in Formula 1, *-(L3) n3 -Z1-(L4) n4 The group represented by -* is a group represented by any one selected from Formula 5-1 to Formula 5-10: In formulas 5-1 to 5-10, T1 is O, S, N (R 10b ) or C(R 10b )(R 10c ), e6 is an integer selected from 0 to 6, e8 is an integer selected from 0 to 8, e10 is an integer selected from 0 to 10, R 10b and R 10c Each independently of the reference R in formula 1 10a The same as defined above, Y1, R1, R2, a4, b4, a6, b6 and R 10a Each is the same as defined in Formula 1, and * indicates a bonding site to an adjacent atom.

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