Light-emitting device including heterocyclic compound and electronic device including the same

Abstract

Provided are a light-emitting device including a heterocyclic compound and an electronic device including the light-emitting device. The light-emitting device includes a first electrode, a second electrode facing the first electrode, and an intermediate layer between the first and second electrodes and including an emission layer, wherein the emission layer includes at least one heterocyclic compound represented by Formula 1.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0062652, filed on May 25, 2020, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

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

[0004] Among the light-emitting devices, an organic light-emitting device (OLED) is a self-emitting device having wide viewing angles, high contrast, short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed compared to other devices in the related art.

[0005] An OLED includes a first electrode on a substrate, and a hole transport region, an emissive layer, an electron transport region, and a second electrode stacked sequentially on the first electrode. Holes provided from the first electrode can move to the emissive layer through the hole transport region, and electrons provided from the second electrode can move to the emissive layer through the electron transport region. Carriers, such as holes and electrons, recombine in the emissive layer to generate excitons. These excitons transition (e.g., relax) from an excited state to a ground state, thereby generating light. Summary of the Invention

[0006] One or more embodiments of the present disclosure relate to a light-emitting device including a heterocyclic compound having excellent light efficiency and high stability, and an electronic device including the light-emitting device.

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

[0008] Aspects of embodiments of the present disclosure provide a light emitting device including a first electrode, a second electrode facing the first electrode, and an intermediate layer between the first electrode and the second electrode and including an emission layer.

[0009] wherein the intermediate layer further comprises a hole transport region between the first electrode and the emission layer,

[0010] The hole transport region includes the compound represented by Formula 201, the compound represented by Formula 202, or any combination thereof, and

[0011] The emission layer includes at least one heterocyclic compound represented by Formula 1:

[0012] Formula 1

[0013]

[0014] Formula 201

[0015]

[0016] Formula 202

[0017]

[0018] In formula 1,

[0019] X2 is O, S, Se, C (Z 2a )(Z 2b ) or N(Z 2a ),

[0020] X3 is O, S, Se, C (Z 3a )(Z 3b ) or N(Z 3a ),

[0021] X4 is O, S, Se, C (Z 4a )(Z 4b ) or N(Z 4a) ,

[0022] Ring CY1 to Ring CY4 are each independently C3-C 60 Carbocyclic group or C1-C 60 Heterocyclic groups,

[0023] R0 to R5, Z 2a 、Z 2b 、Z 3a 、Z 3b 、Z 4a and Z 4b 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 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, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2),

[0024] a1 to a4 are each independently an integer selected from 0 to 20,

[0025] a56 is an integer selected from 0 to 6,

[0026] Z 2a or Z 2b Optionally linked to R2 to form an unsubstituted or substituted R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups,

[0027] Z 3a or Z 3b Optionally linked to R3 to form an unsubstituted or substituted 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups,

[0028] Z 4a or Z 4b Optionally linked to R4 to form an unsubstituted or substituted R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups,

[0029] R 10a Selected from:

[0030] Deuterium (-D), -F, -Cl, -Br, -I, hydroxy, cyano, or nitro;

[0031] 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 groups, C1-C60 Heterocyclic groups, C6-C 60 Aryloxy, C6-C 60 Arylthio, -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;

[0032] Each unsubstituted or substituted C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy or C6-C 60 Arylthio: 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 groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy, C6-C 60 Arylthio, -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

[0033] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ),-C(=O)(Q 31 )、-S(=O)2(Q 31) or -P(=O)(Q 31 )(Q 32 ),and

[0034] Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each independently represents: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 Alkoxy; or each unsubstituted or deuterated, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C substituted by alkoxy, phenyl, biphenyl or any combination thereof 60 Carbocyclic group or C1-C 60 Heterocyclic groups,

[0035] Among them, in Equation 201 and Equation 202,

[0036] L 201 To L 204 are each independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups,

[0037] L 205 For *-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 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups,

[0038] xa1 to xa4 are each independently an integer selected from 0 to 5,

[0039] xa5 is an integer selected from 1 to 10, and

[0040] R 201to R 204 and Q 201 may be independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups,

[0041] R 201 and R 202 Optionally, through a single bond, unsubstituted or substituted 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,

[0042] R 203 and R 204 Optionally, through a single bond, unsubstituted or substituted 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 C2-C5 alkenyl group. 10a Replaced C8-C 60 Polycyclic groups,

[0043] na1 is an integer selected from 1 to 4, and * and *' each indicate a binding site with an adjacent atom.

[0044] Another aspect of the embodiments of the present disclosure provides a light emitting device including a first electrode, a second electrode facing the first electrode, and an intermediate layer between the first electrode and the second electrode and including an emission layer.

[0045] The light emitting device further includes a second capping layer outside the second electrode, the second capping layer having a refractive index equal to or greater than 1.6, and

[0046] The emission layer includes at least one heterocyclic compound represented by Formula 1.

[0047] Another aspect of the embodiments of the present disclosure provides an electronic device including a light emitting device, the electronic device further including a thin film transistor including a source electrode and a drain electrode, and a first electrode of the light emitting device electrically coupled to the source electrode or the drain electrode of the thin film transistor. BRIEF DESCRIPTION OF THE DRAWINGS

[0048] The above and other aspects and features of certain embodiments of the present disclosure will become more apparent from the following description taken in conjunction with the accompanying drawings, in which:

[0049] Figure 1 is a schematic cross-sectional view of a light emitting device according to an embodiment;

[0050] Figure 2 is a schematic cross-sectional view of a light emitting device according to another embodiment;

[0051] Figure 3 is a schematic cross-sectional view of a light emitting device according to another embodiment. DETAILED DESCRIPTION

[0052] Reference will now be made in more detail to embodiments, examples of which are shown in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the description set forth herein. Therefore, embodiments are described below with reference to the figures only to illustrate aspects of the embodiments of the present description. As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. Throughout this disclosure, the expression "at least one of a, b, and c" means only a, only b, only c, both a and b, both a and c, both b and c, all of a, b, and c, or variations thereof.

[0053] Aspects of embodiments of the present disclosure provide a heterocyclic compound represented by Formula 1:

[0054] Formula 1

[0055]

[0056] In Formula 1, X2 can be O, S, Se, C (Z 2a )(Z 2b ) or N(Z 2a ).

[0057] In an embodiment, X2 may be O or N (Z 2a ), but the embodiments of the present disclosure are not limited thereto.

[0058] In Formula 1, X3 can be O, S, Se, C (Z 3a )(Z 3b ) or N(Z 3a ).

[0059] For example, X3 can be O or N (Z 3a ), but the embodiments of the present disclosure are not limited thereto.

[0060] In Formula 1, X4 can be O, S, Se, C (Z 4a )(Z 4b ) or N(Z 4a ).

[0061] In an embodiment, X4 may be O or N (Z 4a ), but the embodiments of the present disclosure are not limited thereto.

[0062] In Formula 1, ring CY1 to ring CY4 can each independently be C3-C 60 Carbocyclic group or C1-C 60 Heterocyclic group.

[0063] In an embodiment, Ring CY1 to Ring CY4 may each independently be:

[0064] Phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrene, 1,2-triphenylenyl, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, thienyl, furanyl, indolyl, benzoborol, benzophosphol, indenyl, benzosilol, benzogermanol, benzothienyl, benzoselenophene, benzofuranyl, carbazolyl, dibenzoborol, dibenzophosphol, fluorenyl, dibenzosilyl Heterocyclopentadienyl, dibenzogermanyl, dibenzothiophene, dibenzoselenophene, dibenzofuranyl, dibenzothiophene 5-oxide, 9H-fluoren-9-one, dibenzothiophene 5,5-dioxide, azaindolyl, azabenzoborolyl, azabenzophospholyl, azaindenyl, azabenzosilyl, azabenzogermanyl, azabenzothiophene, azabenzoselenophene, azabenzene azadibenzofuranyl, azacarbazolyl, azadibenzoborol, azadibenzophosphol, azafluorenyl, azadibenzosilol, azadibenzogermanyl, azadibenzothiophene, azadibenzoselenophene, azadibenzofuranyl, azadibenzothiophene 5-oxide, aza-9H-fluoren-9-one, azadibenzothiophene 5,5-dioxide, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl , triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, 5,6,7,8-tetrahydroisoquinolyl or 5,6,7,8-tetrahydroquinolyl, but embodiments of the present disclosure are not limited thereto.

[0065] In one or more embodiments, at least one selected from rings CY1 to CY4 may be a phenyl group, but embodiments of the present disclosure are not limited thereto.

[0066] In formula 1, R0 to R5, Z 2a 、Z 2b 、Z 3a 、Z3b 、Z 4a and Z 4b 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, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2). R 10a and Q1 to Q3 may each be the same as described in this specification.

[0067] In an embodiment, R0 to R5, Z 2a 、Z 2b 、Z 3a 、Z 3b 、Z 4a and Z 4b Can be independently:

[0068] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, or nitro

[0069] Each unsubstituted or substituted C1-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl or C1-C 20Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, -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 ),-P(=O)(Q 31 )(Q 32) or any combination thereof.

[0070] each unsubstituted or substituted by cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzo thiophene, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophene, azafluorenyl, azadibenzosilacyclopentadienyl, piperidinyl, acridinyl, phenothiazinyl, 1,2,3,4-tetrahydroquinolinyl or phenoxazinyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl, C1-C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indole yl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -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 ),-P(=O)(Q 31 )(Q 32) or any combination thereof; or

[0071] -B(Q 1) (Q2), -P(Q1)(Q2), or -C(═O)(Q1), but the embodiments of the present disclosure are not limited thereto.

[0072] In one or more embodiments, R0 may be hydrogen or deuterium, but the embodiments of the present disclosure are not limited thereto.

[0073] In one or more embodiments, R1 and R2 may each independently be a piperidinyl group, a carbazolyl group, an acridinyl group, a phenothiazinyl group, a 1,2,3,4-tetrahydroquinolinyl group, a phenoxazinyl group, or -N(Q1)(Q2), but the embodiments of the present disclosure are not limited thereto.

[0074] Q1 and Q2 can be independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 Alkoxy; C3-C 10 Cycloalkyl; C1-C 10 Heterocycloalkyl; C3-C 10 Cycloalkenyl; C1-C 10Heterocycloalkenyl; C6-C 60 Aryl; C1-C 60 Heteroaryl; monovalent non-aromatic fused polycyclic group; monovalent non-aromatic fused heteropolycyclic group and C1-C substituted by at least one selected from deuterium, -F and cyano 60 alkyl;

[0075] Selected from deuterium, -F, cyano, C1-C 60 C6-C substituted by at least one of alkyl, biphenyl and terphenyl 60 Aryl,

[0076] However, the embodiments of the present disclosure are not limited thereto.

[0077] In an embodiment, at least one selected from R3 and R4 may be hydrogen, but embodiments of the present disclosure are not limited thereto.

[0078] In Formula 1, a1 to a4 may each independently be an integer selected from 0 to 20.

[0079] In an embodiment, a1 to a4 may each independently be an integer selected from 0 to 6, but the embodiments of the present disclosure are not limited thereto.

[0080] In Formula 1, a56 may be an integer selected from 0 to 6.

[0081] In formula 1, Z 2a or Z 2b may be optionally linked to R2 to form an unsubstituted or substituted group consisting of at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups,

[0082] Z 3a or Z 3b may be optionally linked to R3 to form an unsubstituted or substituted group consisting of at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 a heterocyclic group, and

[0083] Z 4a or Z 4b may be optionally linked to R4 to form an unsubstituted or substituted group consisting of at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group.

[0084] In formula 1, R 10a Can be:

[0085] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, or nitro;

[0086] 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 groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy, C6-C 60 Arylthio, -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;

[0087] Each unsubstituted or substituted C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy or C6-C 60 Arylthio: 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 groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy, C6-C 60 Arylthio, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 ),-C(=O)(Q 21 )、-S(=O)2(Q21 ),-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or

[0088] -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 ).

[0089] In formula 1, 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; or 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 group or C1-C 60 Heterocyclic group.

[0090] In an embodiment, Formula 1 may be represented by any one of Formulas 1A to 1D, but embodiments of the present disclosure are not limited thereto.

[0091]

[0092] In Formula 1A to Formula 1D,

[0093] X2 to X4, ring CY1 to ring CY4, R0 to R5, a1 to a4, and a56 may each be the same as described in the present specification.

[0094] X 2A Can be C(Z 2a )(Z 2b ) or N(Z 2a ),

[0095] X 3BCan be C(Z 3a )(Z 3b ) or N(Z 3a ),

[0096] X 4C Can be C(Z 4a )(Z 4b ) or N(Z 4a ),

[0097] Ring CY6 to Ring CY8 may each be the same as described in conjunction with Ring CY1 in this specification,

[0098] R6 to R8 may each be the same as described in conjunction with R1 in this specification, and

[0099] a6 to a8 may each be the same as described in conjunction with a1 in this specification.

[0100] In one or more embodiments, Formula 1 may be represented by any one of Formula 1A-1 to Formula 1D-1, but embodiments of the present disclosure are not limited thereto.

[0101]

[0102]

[0103] In Formula 1A-1 to Formula 1D-1,

[0104] X2 to X4, ring CY1 to ring CY4, R0 to R5, a1 to a4, and a56 may each be the same as described in the present specification.

[0105] X 2A Can be C(Z 2a )(Z 2b ) or N(Z 2a ),

[0106] X 3B Can be C(Z 3a )(Z 3b ) or N(Z 3a ),

[0107] X 4C Can be C(Z 4a )(Z 4b ) or N(Z 4a ),

[0108] R6 to R8 may each be the same as described in conjunction with R1 in this specification,

[0109] a66 is the same as described in conjunction with a56 in this specification,

[0110] a74 and a84 may each independently be an integer selected from 0 to 4.

[0111] In Formula 1, ring CY1 and ring CY2 may be identical to each other, but embodiments of the present disclosure are not limited thereto.

[0112] In an embodiment, ring CY1 and ring CY2 may be identical to each other, and R1 and R2 may be identical to each other. However, embodiments of the present disclosure are not limited thereto.

[0113] In one or more embodiments, ring CY1 and ring CY2 may be identical to each other, and a1 and a2 may be identical to each other. However, embodiments of the present disclosure are not limited thereto.

[0114] In an embodiment, the heterocyclic compound may be one selected from Compounds 1 to 40, but embodiments of the present disclosure are not limited thereto:

[0115]

[0116]

[0117]

[0118] The heterocyclic compound represented by Formula 1 may have a wide plate structure.

[0119] The heterocyclic compound includes: i) a piperidinyl group in the main chain, which can reduce the number of freely rotatable bonds compared to a non-fused main chain, thereby showing the effect of making the molecule (heterocyclic compound) rigid in terms of bond dissociation energy (BDE). Moreover, compared to a main chain in which the ring is formed outward rather than in the central benzene (for example, the ring is at the periphery of the compound rather than directly bonded to the benzene ring at the center of the heterocyclic compound), the central benzene in which the piperidinyl group is formed can be located between N, X2 and B, which is the strongest multi-resonance position (for example, the position that provides the most resonance structures and / or the greatest degree of resonance effect). According to this mechanism, the piperidinyl group can have abundant electrons, and in this regard, the multi-resonance of the central benzene can be more activated (or increased), thereby showing the effect of compensating for the chemical instability originally possessed by the heterocyclic compound. In addition, in the heterocyclic compound, ii) R0 is not connected to ring CY3 or R0 is not connected to CY4. Therefore, the heterocyclic compound can have a wide plate-like structure, and accordingly, multiple resonances can be activated, thereby activating the delocalization of electrons in the molecule (heterocyclic compound), and the luminescence efficiency can be improved due to the high polarizability. Accordingly, the heterocyclic compound can be used as a high-efficiency delayed fluorescence luminescent material. In this regard, electronic devices such as organic light-emitting devices including the heterocyclic compound can have low driving voltage, excellent light emission efficiency, and long life.

[0120] The synthesis method of the heterocyclic compound represented by Formula 1 should be easily apparent to those skilled in the art by referring to the Synthesis Examples and / or Examples described below.

[0121] At least one heterocyclic compound represented by Formula 1 may be included in a light-emitting device (eg, an organic light-emitting device).

[0122] Another aspect of an embodiment of the present disclosure provides a light-emitting device including: a first electrode; a second electrode facing the first electrode; and an intermediate layer between the first electrode and the second electrode and including an emission layer, wherein the intermediate layer further includes a hole transport region between the first electrode and the emission layer, the hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof, and the emission layer includes at least one heterocyclic compound represented by Formula 1:

[0123] Formula 201

[0124]

[0125] Formula 202

[0126]

[0127] In Equations 201 and 202,

[0128] L 201 To L 204 may be independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups,

[0129] 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 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups,

[0130] xa1 to xa4 may each independently be an integer selected from 0 to 5,

[0131] xa5 may be an integer selected from 1 to 10,

[0132] R 201 to R 204 and Q201 may be independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups,

[0133] 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,

[0134] 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

[0135] na1 may be an integer selected from 1 to 4.

[0136] In one or more embodiments,

[0137] The first electrode of the light emitting device may be an anode,

[0138] The second electrode of the light emitting device may be a cathode,

[0139] The intermediate layer may further include an electron transport region between the emissive layer and the second electrode,

[0140] 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

[0141] 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.

[0142] In one or more embodiments, at least one selected from the hole transport region and the emission layer includes an aromatic amine-containing compound, an acridine-containing compound, a carbazole-containing compound, or any combination thereof; or at least one selected from the emission layer and the electron transport region includes a silicon-containing compound, a phosphine oxide-containing compound, a sulfur oxide-containing compound, a phosphorus oxide-containing compound, a triazine-containing compound, a pyrimidine-containing compound, a pyridine-containing compound, a dibenzofuran-containing compound, a dibenzothiophene-containing compound, or any combination thereof.

[0143] In one or more embodiments, the emission layer included in the intermediate layer of the light emitting device may include a dopant and a host, and the dopant may include a heterocyclic compound. For example, a heterocyclic compound may be used as the dopant.

[0144] The emitting layer may emit red, green, blue, and / or white light. For example, the emitting layer may emit blue light or blue-green light. For example, the blue light or blue-green light may have a maximum emission wavelength in the range of about 400 nm to about 500 nm.

[0145] For example, the emission layer may have a lowest excited triplet energy level equal to or greater than 2.5 eV and equal to or less than 3.0 eV.

[0146] The heterocyclic compound included in the emission layer may serve as a delayed fluorescence dopant to emit delayed fluorescence from the emission layer.

[0147] In an embodiment, the light-emitting device may further include a second capping layer outside the second electrode, and the second capping layer may include one selected from 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.

[0148] In embodiments, the emission layer may be formed by a wet method and / or a vapor deposition method.

[0149] In one or more embodiments, a light emitting device may include:

[0150] a first capping layer outside the first electrode;

[0151] A second capping layer outside the second electrode; or

[0152] a first capping layer and a second capping layer.

[0153] Another aspect of the present disclosure provides a light emitting device including: a first electrode, a second electrode facing the first electrode, and an intermediate layer between the first electrode and the second electrode and including an emission layer.

[0154] The light emitting device may further include a second capping layer outside the second electrode, the second capping layer having a refractive index equal to or greater than 1.6, and

[0155] The emission layer includes at least one heterocyclic compound represented by Formula 1.

[0156] In an embodiment, the encapsulation portion may be on the second capping layer. The encapsulation portion may be on the light emitting device to protect the light emitting device from moisture or oxygen.

[0157] In an embodiment, the packaging portion may include:

[0158] Inorganic films, including silicon nitride (SiN x ), silicon oxide (SiO x ), indium tin oxide, indium zinc oxide, or any combination thereof;

[0159] An organic film comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resin, epoxy resin, or any combination thereof; or

[0160] A combination of inorganic and organic membranes.

[0161] Another aspect of the present disclosure provides an electronic device including a light emitting device. The electronic device may further include a thin film transistor.

[0162] For example, the electronic device may further include a thin film transistor including a source electrode and a drain electrode, and the first electrode of the light emitting device may be electrically coupled to the source electrode or the drain electrode.

[0163] In an embodiment, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof. For example, the electronic device may be a tablet electronic device, but the embodiments of the present disclosure are not limited thereto.

[0164] The description of the electronic device is the same as above.

[0165] In the present specification, the expression “(the intermediate layer) includes a heterocyclic compound” may be interpreted as meaning “(the intermediate layer) may include one heterocyclic compound of Formula 1, or two different heterocyclic compounds of Formula 1”.

[0166] For example, the intermediate layer may include only Compound 1 as the heterocyclic compound. In an embodiment, Compound 1 may be included in the emission layer of the light-emitting device. In one or more embodiments, the intermediate layer may include Compound 1 and Compound 2 as heterocyclic compounds. In this regard, Compound 1 and Compound 2 may be included in the same layer (for example, Compound 1 and Compound 2 are both included in the emission layer) or in different layers (for example, Compound 1 may be included in the emission layer and Compound 2 may be included in the electron transport region).

[0167] The term "intermediate layer" as used herein refers to a single layer and / or all layers between a first electrode and a second electrode of a light-emitting device.

[0168] Figure 1 Description

[0169] Figure 1 1 is a schematic cross-sectional view of a light emitting device 10 according to an embodiment of the present invention. The light emitting device 10 includes a first electrode 110 , an intermediate layer 130 , and a second electrode 150 .

[0170] In the following, we will combine Figure 1 The structure of the light emitting device 10 and a method of manufacturing the light emitting device 10 according to the embodiment are described.

[0171] First electrode 110

[0172] exist Figure 1 In the embodiment, the substrate may be located below the first electrode 110 or above the second electrode 150. The substrate may be a glass substrate and / or a plastic substrate. The substrate may be a flexible substrate. In one or more embodiments, the substrate may include a plastic (or polymer) having excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or a combination thereof.

[0173] For example, the first electrode 110 may be formed by depositing and / or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, a high work function material that can easily inject holes may be used as the material for forming the first electrode 110.

[0174] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material 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, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof may be used as the material used to form the first electrode 110.

[0175] The first electrode 110 may have a single-layer structure including a single layer (composed of a single layer) or a multi-layer structure including a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.

[0176] Middle layer 130

[0177] The intermediate layer 130 is on the first electrode 110. The intermediate layer 130 includes an emission layer.

[0178] The intermediate layer 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 .

[0179] In addition to various appropriate organic materials, the intermediate layer 130 may further include metal-containing compounds such as organometallic compounds and / or inorganic materials such as quantum dots, etc.

[0180] In one or more embodiments, the intermediate layer 130 may include: i) two or more emission units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer between the two emission units. When the intermediate layer 130 includes the emission units and the charge generation layer as described above, the light-emitting device 10 may be a tandem light-emitting device.

[0181] Hole transport region in the intermediate layer 130

[0182] 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 (e.g., consisting of) a plurality of different materials (e.g., consisting of) a plurality of different materials, or iii) a multilayer structure including a plurality of layers including different materials.

[0183] 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.

[0184] For example, the hole transport region may have a multi-layer structure, including a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure or a hole injection layer / hole transport layer / emission auxiliary layer structure, wherein in each structure, the layers are stacked in sequence on the first electrode 110.

[0185] The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:

[0186] Formula 201

[0187]

[0188] Formula 202

[0189]

[0190] In Equations 201 and 202,

[0191] L 201 To L 204 may be independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups,

[0192] 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 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups,

[0193] xa1 to xa4 may each independently be an integer selected from 0 to 5,

[0194] xa5 may be an integer selected from 1 to 10,

[0195] R 201 to R 204 and Q 201 may be independently unsubstituted or substituted with at least one R 10a Substituted C3-C60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups,

[0196] 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 (e.g., carbazolyl, etc.) substituted C8-C 60 Polycyclic groups (for example, refer to the following compound HT16),

[0197] 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

[0198] na1 may be an integer selected from 1 to 4.

[0199] For example, Formula 201 and Formula 202 may each include at least one of the groups represented by Formula CY201 to Formula CY217:

[0200]

[0201] Regarding formula CY201 to formula CY217, R 10b and R 10c Can be combined with R 10a Same as described, CY 201 To Ring CY 204 Can be independently C3-C 20 Carbocyclic group or C1-C 20 heterocyclic group, and at least one hydrogen in Formula CY201 to Formula CY217 is unsubstituted or replaced by at least one R described herein 10a replace.

[0202] In an embodiment, ring CY in Formula CY201 to Formula CY217 201 To Ring CY 204 Each independently may be phenyl, naphthyl, phenanthryl or anthracenyl.

[0203] In one or more embodiments, Formula 201 and Formula 202 may each include at least one selected from the groups represented by Formulas CY201 to CY203.

[0204] 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.

[0205] In one or more embodiments, in Formula 201, xa1 may be 1, R 201 may be a group represented by any one of formula CY201 to formula CY203, xa2 may be 0, and R 202 It may be a group represented by any one of Formula CY204 to Formula CY207.

[0206] In one or more embodiments, each of Formula 201 and Formula 202 may not include the groups represented by Formula CY201 to Formula CY203.

[0207] In one or more embodiments, each of Formula 201 and Formula 202 may not include the groups represented by Formula CY201 to Formula CY203, and may include at least one selected from the groups represented by Formula CY204 to Formula CY217.

[0208] In one or more embodiments, each of Formula 201 and Formula 202 may not include the groups represented by Formulas CY201 to CY217.

[0209] For example, the hole transport region may include one selected from compounds HT1 to HT44, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), 9-(4-(tert-butyl)phenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), or any combination thereof:

[0210]

[0211]

[0212]

[0213]

[0214] 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 any of the above ranges, appropriate or satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage.

[0215] The emission assisting layer can improve light emission efficiency by compensating the optical resonance distance according to the wavelength of light emitted by the emission layer, and the electron blocking layer can block or reduce the flow of electrons from the electron transport region. The emission assisting layer and the electron blocking layer may include the materials described above.

[0216] p-dopant

[0217] In addition to these materials, the hole transport region may further include a charge generating material for improving conductive properties (e.g., electrical conductivity). The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer including (e.g., consisting of) the charge generating material).

[0218] For example, the charge generating material may be a p-dopant.

[0219] In an embodiment, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level equal to or less than −3.5 eV.

[0220] In an embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound containing elements EL1 and EL2, or any combination thereof.

[0221] Examples of quinone derivatives are TCNQ and F4-TCNQ

[0222] Examples of the cyano group-containing compound are HAT-CN and the compound represented by Formula 221:

[0223]

[0224] Formula 221

[0225]

[0226] In formula 221,

[0227] R 221 to R 223 may be independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 a heterocyclic group, and

[0228] Selected from R 221 to R 223 At least one of them may be each independently C3-C 60 Carbocyclic group 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.

[0229] Regarding the compound containing elements EL1 and EL2, element EL1 may be a metal, a metalloid, or a combination thereof, and element EL2 may be a nonmetal, a metalloid, or a combination thereof.

[0230] Examples of metals 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), etc.). ), 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 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.).

[0231] Examples of metalloids are silicon (Si), antimony (Sb), and tellurium (Te).

[0232] Examples of non-metals are oxygen (O) and halogens (eg, F, Cl, Br, I, etc.).

[0233] For example, the compound containing elements EL1 and EL2 may be a metal oxide, a metal halide (e.g., a metal fluoride, a metal chloride, a metal bromide and / or a metal iodide), a metalloid halide (e.g., a metalloid fluoride, a metalloid chloride, a metalloid bromide and / or a metalloid iodide), a metal telluride, or any combination thereof.

[0234] Examples of metal oxides are tungsten oxides (e.g., WO, W2O3, WO2, WO3, and / or W2O5), vanadium oxides (e.g., VO, V2O3, VO2, and / or V2O5), molybdenum oxides (e.g., MoO, Mo2O3, MoO2, MoO3, and / or Mo2O5), and rhenium oxides (e.g., ReO3).

[0235] Examples of the metal halide are alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and lanthanide metal halides.

[0236] Examples of alkali metal halides are LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.

[0237] Examples of alkaline earth halides are BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, and BaI2.

[0238] Examples of transition metal halides are titanium halides (e.g., TiF4, TiCl4, TiBr4, and / or TiI4), zirconium halides (e.g., ZrF4, ZrCl4, ZrBr4, and / or ZrI4), hafnium halides (e.g., HfF4, HfCl4, HfBr4, and / or HfI4), vanadium halides (e.g., VF3, VCl3, VBr3, and / or VI3), niobium halides (e.g., NbF3, NbCl3, NbBr3, and / or NbI3), tantalum halides (e.g., TaF3, TaCl3, TaBr3, etc.), and zirconium halides (e.g., ZrF4, ZrCl4, ZrBr4, and / or ZrI4). and / or TaI3), chromium halides (e.g., CrF3, CrCl3, CrBr3 and / or CrI3), molybdenum halides (e.g., MoF3, MoCl3, MoBr3 and / or MoI3), tungsten halides (e.g., WF3, WCl3, WBr3 and / or WI3), manganese halides (e.g., MnF2, MnCl2, MnBr2 and / or MnI2), technetium halides (e.g., TcF2, TcCl2, TcBr2 and / or TcI2), rhenium halides (e.g., ReF2, ReCl2, ReBr2 and / or or ReI2), iron halides (e.g., FeF2, FeCl2, FeBr2 and / or FeI2), ruthenium halides (e.g., RuF2, RuCl2, RuBr2 and / or RuI2), osmium halides (e.g., OsF2, OsCl2, OsBr2 and / or OsI2), cobalt halides (e.g., CoF2, CoCl2, CoBr2 and / or CoI2), rhodium halides (e.g., RhF2, RhCl2, RhBr2 and / or RhI2), iridium halides (e.g., IrF2, IrCl2, IrBr2, and / or IrI2), nickel halides (e.g., NiF2, NiCl2, NiBr2 and / or NiI2), palladium halides (e.g., PdF2, PdCl2, PdBr2 and / or PdI2), platinum halides (e.g., PtF2, PtCl2, PtBr2 and / or PtI2), copper halides (e.g., CuF, CuCl, CuBr and / or CuI), silver halides (e.g., AgF, AgCl, AgBr and / or AgI), and gold halides (e.g., AuF, AuCl, AuBr and / or AuI).

[0239] Examples of late transition metal halides are zinc halides (eg, ZnF 2 , ZnCl 2 , ZnBr 2 and / or ZnI 2 ), indium halides (eg, InI 3 ), and tin halides (eg, SnI 2 ).

[0240] Examples of lanthanide metal halides are YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, and SmI3.

[0241] An example of a metalloid halide is antimony halide (eg, SbCl 5 ).

[0242] Examples of metal tellurides are alkali metal tellurides (e.g., Li2Te, Na2Te, K2Te, Rb2Te, and / or Cs2Te), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, and / or BaTe), transition metal tellurides (e.g., TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, Fe Te, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe and / or Au2Te), late transition metal tellurides (e.g., ZnTe), and lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe and / or LuTe).

[0243] Emission layer in the middle layer 130

[0244] 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 of a red emission layer, a green emission layer and a blue emission layer, wherein the two or more layers are in contact with each other (e.g., physical contact) or separated from each other. In one or more embodiments, the emission layer may include two or more materials of a red light-emitting material, a green light-emitting material and a blue light-emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light.

[0245] The emissive layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.

[0246] 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.

[0247] In one or more embodiments, the emissive layer may include quantum dots.

[0248] In some embodiments, the emissive layer may include a delayed fluorescent material. The delayed fluorescent material may be used as a host or a dopant in the emissive layer.

[0249] 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 any of the above ranges, excellent light emission characteristics can be obtained without a significant increase in driving voltage.

[0250] main body

[0251] In an embodiment, the host may include a compound represented by Formula 301:

[0252] Formula 301:

[0253] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21

[0254] Wherein, in formula 301,

[0255] Ar 301 and L 301 may be independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group.

[0256] xb11 can be 1, 2 or 3,

[0257] xb1 may be an integer selected from 0 to 5,

[0258] 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 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C3-C 60Carbocyclic 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 ).

[0259] xb21 may be an integer selected from 1 to 5, and

[0260] Q 301 To Q 303 Each may be the same as described in conjunction with Q1.

[0261] For example, when xb11 in Formula 301 is 2 or greater, two or more Ar 301 can be connected to each other via a single bond.

[0262] 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:

[0263] Formula 301-1

[0264]

[0265] Formula 301-2

[0266]

[0267] In Formula 301-1 and Formula 301-2,

[0268] Ring A 301 To Ring A 304 may be independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups,

[0269] X 301 Can be O, S, N-[(L 304 ) xb4 -R 304 ]、C(R 304 )(R305 ) or Si(R 304 )(R 305 ),

[0270] xb22 and xb23 can each independently be 0, 1 or 2,

[0271] L 301 , xb1 and R 301 may be the same as described in this specification,

[0272] L 302 To L 304 Can be combined with L independently 301 Same as described,

[0273] xb2 to xb4 may each independently be the same as described in conjunction with xb1, and

[0274] R 302 to R 305 and R 311 to R 314 Can be combined with R 301 Same as described.

[0275] In one or more embodiments, the host may include an alkaline earth metal complex. In one or more embodiments, the host may be a Be complex (eg, compound H55), a Mg complex, a Zn complex, or any combination thereof.

[0276] In one or more embodiments, the host may include one selected from compounds H1 to H124, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tris(carbazol-9-yl)benzene (TCP), or any combination thereof:

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283] Delayed fluorescence materials

[0284] The emissive layer may include a delayed fluorescent material.

[0285] The delayed fluorescent material used herein may be selected from any appropriate compound capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.

[0286] The delayed fluorescent material included in the emission layer may function as a host or a dopant according to the types (or compositions) of other materials included in the emission layer.

[0287] In an embodiment, the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material may be equal to or greater than 0 eV and equal to or less than 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, up-conversion from the triplet state of the delayed fluorescent material to the singlet state can effectively occur, and thus, the luminous efficiency of the organic light-emitting device 10 can be improved.

[0288] In an embodiment, 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) and at least one electron acceptor (e.g., sulfoxide, cyano, or C1-C1 containing π-electron-deficient nitrogen) 60 cyclic groups), and / or ii) materials including C8-C 60 Polycyclic materials, in C8-C 60 Two or more cyclic groups in a polycyclic group share boron (B) and are fused to each other (eg, bonded together).

[0289] The delayed fluorescent material may include at least one of compounds DF1 to DF9:

[0290]

[0291] quantum dots

[0292] The emissive layer may include quantum dots.

[0293] The term "quantum dot" as used herein refers to a crystal of a semiconductor compound and may include any suitable material capable of emitting light at various suitable emission wavelengths depending on the size of the crystal.

[0294] For example, the diameter of the quantum dots may be in the range of about 1 nm to about 10 nm.

[0295] Quantum dots can be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, and / or processes similar thereto.

[0296] A wet chemical process is a method of mixing a solvent and a precursor material and then growing quantum dot particle crystals. As the crystals grow, the organic solvent acts as a dispersant that naturally coordinates on the surface of the quantum dot crystals and controls crystal growth. Therefore, by using processes that are easy to perform at low cost compared to vapor deposition processes (such as metal organic chemical vapor deposition (MOCVD) processes and / or molecular beam epitaxy (MBE) processes), the growth of quantum dot particles can be controlled.

[0297] 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.

[0298] Examples of II-VI semiconductor compounds are: binary compounds such as CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe and / or MgS; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnS e, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe and / or MgZnS; quaternary compounds, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and / or HgZnSTe; or any combination thereof.

[0299] Examples of Group III-V semiconductor compounds 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; and quaternary compounds such as GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNPs, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNPs, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and / or GaAlNPs, or any combination thereof. The Group III-V semiconductor compounds may further include a Group II element. Examples of the Group III-V semiconductor compound further including a Group II element are InZnP, InGaZnP and / or InAlZnP.

[0300] Examples of III-VI semiconductor compounds are: binary compounds such as GaS, GaSe, Ga2Se3, GaTe, InS, In2S3, InSe, In2Se3 and / or InTe; ternary compounds such as InGaS3 and / or InGaSe3; or any combination thereof.

[0301] Examples of Group I-III-VI semiconductor compounds are: ternary compounds such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2 and / or AgAlO2.

[0302] Examples of Group IV-VI semiconductor compounds are: binary compounds such as SnS, SnSe, SnTe, PbS, PbSe and / or PbTe; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe and / or SnPbTe; quaternary compounds such as SnPbSSe, SnPbSeTe and / or SnPbSTe; or any combination thereof.

[0303] In an embodiment, the Group IV element or compound may include: a single element compound, such as Si and / or Ge; a binary compound, such as SiC and / or SiGe; or any combination thereof.

[0304] Each element included in the multi-element compound such as the binary compound, the ternary compound, and the quaternary compound may be present in the particle at a uniform concentration or a non-uniform concentration.

[0305] In some embodiments, the quantum dot may have a single structure or a core-shell dual structure, the single structure having a uniform (e.g., substantially uniform) concentration of each element included in the corresponding quantum dot. For example, the material included in the core may be different from the material included in the shell.

[0306] The shell of a quantum dot can serve as a protective layer for maintaining semiconductor properties by preventing or reducing chemical degradation of the core, and / or can serve as a charging layer for imparting 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.

[0307] Examples of quantum dot shells are metal and / or non-metal oxides, semiconductor compounds, or any combination thereof. Examples of metal and / or non-metal oxides are binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and / or NiO; ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, and / or CoMn2O4; or any combination thereof. As described herein, examples of semiconductor compounds are Group II-VI semiconductor compounds; Group III-V semiconductor compounds; Group III-VI semiconductor compounds; Group I-III-VI semiconductor compounds; Group IV-VI semiconductor compounds; or any combination thereof. For example, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.

[0308] The full width at half maximum (FWHM) of the emission wavelength spectrum of the quantum dots can be equal to or less than about 45 nm, for example, equal to or less than about 40 nm, and for example, equal to or less than about 30 nm. When the FWHM of the emission wavelength spectrum of the quantum dots is within any of the above ranges, color purity and / or color reproducibility can be improved. In addition, light emitted by such quantum dots is omnidirectional (e.g., in substantially all directions). Therefore, a wide viewing angle can be increased.

[0309] Additionally, for example, quantum dots can be spherical, pyramidal, multi-armed, and / or cubic nanoparticles, nanotubes, nanowires, nanofibers, and / or nanoplate particles.

[0310] By adjusting the size of the quantum dots, the band gap can also be adjusted, thereby obtaining light of various appropriate wavelengths in the quantum dot emission layer. Therefore, by using quantum dots of different sizes, a light-emitting device that emits light of various appropriate wavelengths can be implemented. In embodiments, the size of the quantum dots can be selected to emit red, green, and / or blue light. In addition, the size of the quantum dots can be configured to emit white light by combining various appropriate colors of light.

[0311] Electron transport region in the intermediate layer 130

[0312] 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 material), ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single layer including a plurality of different materials (e.g., consisting of a plurality of different materials), or iii) a multilayer structure including a plurality of layers including different materials.

[0313] 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.

[0314] For example, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein in each structure, the layers are stacked in sequence on the emission layer.

[0315] 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 Cyclic group.

[0316] In an embodiment, the electron transport region may include a compound represented by Formula 601:

[0317] Formula 601

[0318] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21

[0319] Wherein, in formula 601,

[0320] Ar 601 and L 601 may be independently unsubstituted or substituted with at least one R10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group.

[0321] xe11 can be 1, 2 or 3,

[0322] xe1 can be 0, 1, 2, 3, 4 or 5,

[0323] R 601 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 ),

[0324] Q 601 To Q 603 Each may be the same as described in conjunction with Q1,

[0325] xe21 can be 1, 2, 3, 4, or 5, and

[0326] 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 Cyclic group.

[0327] In one or more embodiments, when xe11 in Formula 601 is 2 or greater, two or more Ar 601 can be connected to each other via a single bond.

[0328] In one or more embodiments, Ar in Formula 601 601 The anthracenyl group may be substituted or unsubstituted.

[0329] In one or more embodiments, the electron transport region may include a compound represented by Formula 601-1:

[0330] Formula 601-1

[0331]

[0332] Among them, in formula 601-1,

[0333] 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 614 To X 616 At least one of may be N,

[0334] L 611 To L 613 Can be combined with L 601 Same as described,

[0335] xe611 to xe613 may be understood by referring to the description presented in conjunction with xe1.

[0336] R 611 to R 613 Can be combined with R 601 Same as described, and

[0337] 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 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group.

[0338] For example, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 may each independently be 0, 1, or 2.

[0339] The electron transport region may include one selected from compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ, NTAZ, diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1), 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBI), or any combination thereof:

[0340]

[0341]

[0342]

[0343] 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 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 and / or the electron transport layer is within any of the above ranges, appropriate or satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.

[0344] In addition to the materials described above, the electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material.

[0345] 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 with the metal ion of the alkali metal complex and / or alkaline earth metal complex may be hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

[0346] For example, the metal-containing material may include a Li complex. For example, the Li complex may include compound ET-D1 (LiQ) or ET-D2:

[0347]

[0348] The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 150. The electron injection layer may be in direct contact with (eg, in physical contact with) the second electrode 150.

[0349] 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 different materials (e.g., consisting of multiple different materials), or iii) a multi-layer structure including multiple layers that include different materials.

[0350] 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.

[0351] 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.

[0352] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may be oxides and / or halides (e.g., fluorides, chlorides, bromides, and / or iodides), tellurides, or any combination thereof of the alkali metal, the alkaline earth metal, and / or the rare earth metal.

[0353] The alkali metal compound may be an alkali metal oxide (such as Li2O, Cs2O, and / or K2O), an alkali metal halide (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and / or KI), or any combination thereof. The alkaline earth metal compound may include an alkaline earth metal oxide, 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). The rare earth metal compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In an embodiment, the rare earth metal compound may include lanthanide metal tellurides. Examples of lanthanide metal tellurides are 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 Lu2Te3.

[0354] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may include i) one of the metal ions of an alkali metal, an alkaline earth metal and a rare earth metal, and ii) as a ligand attached to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.

[0355] 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, or may further include an organic material (e.g., a compound represented by Formula 601).

[0356] In an embodiment, the electron injection layer may include (e.g., consist of): 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, the electron injection layer may be a KI:Yb co-deposition layer and / or a RbI:Yb co-deposition layer.

[0357] When the electron injection layer further includes an organic material, alkali metals, alkaline earth metals, rare earth metals, alkali metal-containing compounds, alkaline earth metal-containing compounds, rare earth metal-containing compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof may be uniformly or non-uniformly dispersed in the matrix including the organic material.

[0358] 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, appropriate or satisfactory electron injection characteristics can be obtained without a significant increase in driving voltage.

[0359] Second electrode 150

[0360] The second electrode 150 may be on the intermediate layer 130 having such a structure. The second electrode 150 may be a cathode, which is an electron injection electrode, and metals, alloys, conductive compounds, or any combination thereof each having a low work function may be used as a material for forming the second electrode 150.

[0361] 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 a combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0362] The second electrode 150 may have a single-layer structure or a multi-layer structure including two or more layers.

[0363] Capping layer

[0364] The first capping layer may be on the outside of the first electrode 110, and / or the second capping layer may be on the outside of the second electrode 150. In more detail, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the intermediate layer 130, the second electrode 150 are stacked in sequence in the stated order; a structure in which the first electrode 110, the intermediate layer 130, the second electrode 150, and the second capping layer are stacked in sequence in the stated order; or a structure in which the first capping layer, the first electrode 110, the intermediate layer 130, the second electrode 150, and the second capping layer are stacked in sequence in the stated order.

[0365] Light generated in the emission layer of the intermediate layer 130 of the light-emitting device 10 can be extracted toward the outside through the first electrode 110 and the first capping layer, each of which can be a semi-transmissive electrode or a transmissive electrode, or light generated in the emission layer of the intermediate layer 130 of the light-emitting device 10 can be extracted toward the outside through the second electrode 150 and the second capping layer, each of which can be a semi-transmissive electrode or a transmissive electrode.

[0366] The first capping layer and the second capping layer can increase the external luminous efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light emitting device 10 can be increased, thereby also improving the luminous efficiency of the light emitting device 10.

[0367] The first capping layer and the second capping layer may each include a material having a refractive index equal to or greater than 1.6 (at 589 nm).

[0368] 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, and / or a composite capping layer including an organic material and an inorganic material.

[0369] At least one selected from the first capping layer and the second capping layer may each independently include a carbocyclic compound, a heterocyclic compound, an amine-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or a combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine-containing compound may optionally be substituted with a substituent containing O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In an embodiment, at least one selected from the first capping layer and the second capping layer may each independently include an amine-containing compound.

[0370] In one or more embodiments, at least one selected from the first capping layer and the second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.

[0371] In one or more embodiments, at least one selected from the first capping layer and the second capping layer may each independently include a compound selected from compounds HT28 to HT33, compounds CP1 to CP6, β-NPB, or any combination thereof:

[0372]

[0373] electronic devices

[0374] The light emitting device may be included in various suitable electronic devices. In an embodiment, the electronic device including the light emitting device may be a light emitting device and / or an authentication device, etc.

[0375] In addition to the light-emitting device, an electronic device (e.g., a light-emitting device) may further include: i) a color filter, ii) a color conversion layer, or iii) both a color filter and a color conversion layer. The color filter and / or the color conversion layer may be in at least one direction of travel of light emitted from the light-emitting device. In embodiments, the light emitted from the light-emitting device may be blue light or white light. The light-emitting device may be the same as described above. In embodiments, the color conversion layer may include quantum dots. The quantum dots may be, for example, as described herein.

[0376] The electronic device may include a first substrate including 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 sub-pixel regions.

[0377] A pixel defining film may be disposed between the plurality of sub-pixel regions to define each sub-pixel region.

[0378] The color filter may further include a plurality of color filter regions and a light blocking pattern between adjacent ones of the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light blocking pattern between adjacent ones of the plurality of color conversion regions.

[0379] The multiple color filter regions (or multiple color conversion regions) may include a first region emitting a first color of light, a second region emitting a second color of light, and / or a third region emitting a third color of light. The first, second, and / or third color of light may have different maximum emission wavelengths. For example, the first color of light may be red, the second color of light may be green, and the third color of light may be blue. For example, the multiple color filter regions (or multiple color conversion regions) may include quantum dots. More specifically, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include quantum dots. The quantum dots may be the same as those described herein. The first, second, and / or third regions may further include scatterers.

[0380] For example, a light-emitting device may emit a first light, a first region may absorb the first light to emit a first first color light, a second region may absorb the first light to emit a second first color light, and a third region may 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. More specifically, 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.

[0381] In addition to the light emitting device 10 described above, the electronic device may further include a thin film transistor. The thin film transistor may include a source electrode, a drain electrode, and an active layer, wherein any one selected from the source electrode and the drain electrode may be electrically coupled to any one selected from the first electrode and the second electrode of the light emitting device.

[0382] The thin film transistor may further include a gate electrode and / or a gate insulating layer, etc.

[0383] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, and / or an oxide semiconductor, among others.

[0384] The electronic device may further include a sealing portion for sealing the light-emitting device. The sealing portion may be between the color filter and / or color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device 10 to be extracted to the outside while simultaneously (e.g., simultaneously) preventing or reducing the penetration of external air and moisture into the light-emitting device 10. The sealing portion may be a sealing substrate including a transparent glass substrate and / or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one of an organic layer and an inorganic layer. When the sealing portion is a thin-film encapsulation layer, the electronic device may be flexible.

[0385] In addition to the color filter and / or color conversion layer, various suitable functional layers may be further formed on the sealing portion, depending on the application or design of the electronic device. These functional layers may include a touch screen layer and / or a polarizing layer, among others. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, and / or an infrared touch screen layer. The authentication device may be, for example, a biometric authentication device that authenticates an individual using biometric information from a biometric body (e.g., a fingertip and / or pupil).

[0386] In addition to the light emitting device, the authentication device may further include a biometric information collector.

[0387] The electronic device can be applied to various appropriate displays, light sources, lighting, personal computers (e.g., personal mobile computers), mobile phones, digital cameras, electronic notepads, electronic dictionaries, electronic game consoles, medical equipment (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasound diagnostic devices and / or endoscope displays), fish finders, various appropriate measuring tools, instruments (e.g., instruments for vehicles, aircraft and / or ships) and / or projectors, etc.

[0388] Figure 2 and Figure 3 Description

[0389] Figure 2 is a schematic cross-sectional view showing a light emitting device according to an embodiment of the present disclosure.

[0390] Figure 2 The light emitting apparatus includes a substrate 100, a thin film transistor (TFT), a light emitting device, and an encapsulation portion 300 that seals the light emitting device.

[0391] 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 prevents or reduces the penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.

[0392] 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.

[0393] The active layer 220 may include an inorganic semiconductor (such as silicon or polysilicon), an organic semiconductor, and / or an oxide semiconductor, and may include a source region, a drain region, and a channel region.

[0394] 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 .

[0395] An interlayer insulating film 250 may be on the gate electrode 240 . The interlayer insulating film 250 may be between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260 , and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270 .

[0396] 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 in contact with (e.g., in physical contact with) the exposed portions of the source region and the drain region of the active layer 220.

[0397] The TFT can be electrically coupled to the light-emitting device to drive the light-emitting device and is covered by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. The light-emitting device is provided on the passivation layer 280. The light-emitting device includes a first electrode 110, an intermediate layer 130, and a second electrode 150.

[0398] The first electrode 110 may be on the passivation layer 280. The passivation layer 280 does not completely cover the drain electrode 270 and exposes a portion of the drain electrode 270, and the first electrode 110 may be electrically coupled to the exposed portion of the drain electrode 270.

[0399] A pixel-defining layer 290 comprising an insulating material may be formed on the first electrode 110. The pixel-defining layer 290 may expose a certain area of ​​the first electrode 110, and the intermediate layer 130 may be formed in the exposed area of ​​the first electrode 110. The pixel-defining layer 290 may be a polyimide-based organic film or a polyacrylic-based organic film. In some embodiments, at least one layer of the intermediate layer 130 may extend to the upper portion of the pixel-defining layer 290 and may be in the form of a common layer.

[0400] The second electrode 150 may be on the intermediate layer 130, and the capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 is formed to cover the second electrode 150.

[0401] The encapsulation portion 300 may be on the capping layer 170. The encapsulation portion 300 may be on the light emitting device and protect the light emitting device from moisture or oxygen. The encapsulation portion 300 may include: an inorganic film including silicon nitride (SiN x ), silicon oxide (SiO x), indium tin oxide, indium zinc oxide or a combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (e.g., polymethyl methacrylate or polyacrylic acid), an epoxy resin (e.g., aliphatic glycidyl ether (AGE)), or a combination thereof; or a combination of an inorganic film and an organic film.

[0402] Figure 3 Schematic cross-sectional view showing a light emitting device according to one embodiment of the present disclosure.

[0403] In addition to the light-blocking pattern 500 and the functional region 400 additionally on the encapsulation portion 300, Figure 3 Light-emitting devices and Figure 2 The functional area 400 may be: i) a color filter area, ii) a color conversion area, or iii) a combination of a color filter area and a color conversion area. Figure 3 The light emitting devices in the light emitting apparatus may be series light emitting devices.

[0404] Preparation method

[0405] The layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region can be formed in a certain region by using one or more appropriate methods selected from vacuum deposition, spin coating, casting, Langmuir-Brockett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.

[0406] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition can be performed at a deposition temperature of about 100° C. to about 500° C., ... -8 About 10 -3 Torr vacuum and about to about The deposition rate is carried out at .

[0407] Definitions of at least some terms

[0408] As used herein, the term "C3-C 60 A "carbocyclic group" refers to a cyclic group comprising only carbon (e.g., consisting of carbon) and having 3 to 60 carbon atoms, and the term "C1-C 60 The term "heterocyclic group" refers to a cyclic group having 1 to 60 carbon atoms and further including heteroatoms in addition to carbon. 60 Carbocyclic groups and C1-C 60The heterocyclic groups may each be a monocyclic group including one ring (e.g., consisting of one ring) or a polycyclic group in which two or more rings are fused to each other (e.g., bonded together). 60 The number of ring-forming atoms of the heterocyclic group can be 3 to 61.

[0409] As used herein, the term "cyclic group" includes C3-C 60 Carbocyclic groups and C1-C 60 Heterocyclic group.

[0410] As used herein, the term "π-electron-rich C3-C 60 The term "cyclic group" refers to a cyclic group having 1 to 60 carbon atoms and not including *-N=*' as a ring-forming part, and the term "C1-C1 containing a π-electron-deficient nitrogen" as used herein 60 The term "cyclic group" refers to a heterocyclic group having 1 to 60 carbon atoms and including *-N=*' as a ring-forming portion.

[0411] For example,

[0412] C3-C 60 The carbocyclic group can be i) a group T1 or ii) a fused ring group in which two or more groups T1 are fused to each other (e.g., bonded together) (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, hexenyl, pentacenyl, rubenyl, coronenyl, ovalenyl, indenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, indenophenanthrenyl, or indenoanthryl).

[0413] C1-C 60The heterocyclic group may be i) a group T2, ii) a fused ring group in which two or more groups T2 are fused to each other (e.g., bonded together), or iii) a fused ring group in which at least one group T2 and at least one group T1 are fused to each other (e.g., bonded together) (e.g., pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, Indolyl, benzosilolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzosilolyl, dibenzothiophenyl, dibenzofuranyl, indenocarbazolyl, indolecarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzosilolyl, benzoindolecarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzonaphthosilolyl alkenyl, benzofurandibenzofuranyl, benzofurandibenzothienyl, benzothienodibenzothienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinoline quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzosilacyclopentadienyl, azadibenzothiophenyl or azadibenzofuranyl),

[0414] π-electron-rich C3-C 60 The cyclic group may be i) a group T1, ii) a fused ring group in which two or more groups T1 are fused to each other (e.g., bound together), iii) a group T3, iv) a fused ring group in which two or more groups T3 are fused to each other (e.g., bound together), or v) a fused ring group in which at least one group T3 and at least one group T1 are fused to each other (e.g., bound together) (e.g., C3-C 60 carbocyclic group, pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzosilolyl, benzothienyl, benzofuranyl, carbazolyl, dibenzosilolyl, dibenzothienyl, dibenzofuranyl, indenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothienocarbazolyl, benzosilolyl, benzoindolcarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, benzonaphthosilolyl, benzofuranodibenzofuranyl, benzofuranodibenzothienyl or benzothienodibenzothienyl),

[0415] C1-C containing π-electron-deficient nitrogen 60 The cyclic group may be i) a group T4, ii) a fused ring group in which two or more groups T4 are fused to each other (e.g., bound together), iii) a fused ring group in which at least one group T4 and at least one group T1 are fused to each other (e.g., bound together), iv) a fused ring group in which at least one group T4 and at least one group T3 are fused to each other (e.g., bound together), or v) a fused ring group in which at least one group T4, at least one group T1, and at least one group T3 are fused to each other (e.g., bound together) (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzosilacyclopentadienyl, azadibenzothiophenyl, or azadibenzofuranyl),

[0416] The radical T1 can be cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornane (or bicyclo[2.2.1]heptane), norbornenyl, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane or phenyl,

[0417] The group T2 can be furyl, thienyl, 1H-pyrrolyl, silacyclopentadienyl, borocyclopentadienyl, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azasilolyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl or tetrazinyl,

[0418] The group T3 may be a furyl group, a thienyl group, a 1H-pyrrolyl group, a silacyclopentadienyl group or a borocyclopentadienyl group,

[0419] The group T4 can be 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azasilacyclopentadienyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl or tetrazinyl.

[0420] According to the structure of the formula described by the corresponding terms, such as the terms "cyclic group", "C3-C 60 Carbocyclic group", "C1-C 60 Heterocyclic groups", "π-electron-rich C3-C 60 Cyclic group" or "C1-C 60 The term "cyclic group" refers to a monovalent group or a polyvalent group (e.g., a divalent group, a trivalent group, or a tetravalent group, etc.) fused to (e.g., combined with) a cyclic group. In an embodiment, "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".

[0421] In an embodiment, the monovalent C3-C 60 Carbocyclic groups and monovalent C1-C 60 Examples of heterocyclic groups are 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 Examples of heterocyclic groups are 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.

[0422] As used herein, the term "C1-C 60 "Alkyl" refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, preferably C1-C 20 Alkyl, and examples thereof are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl and tert-decyl. As used herein, the term “C1-C1-C1-alkyl” is alkyl, and examples thereof are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl and tert-decyl. 60"Alkylene" refers to a C1-C 60 Alkyl groups have substantially the same structure as divalent groups, preferably C1-C 20 Alkylene or C1-C5 alkylene.

[0423] As used herein, the term "C2-C 60 "Alkenyl" refers to a C2-C 60 The alkyl group is a monovalent hydrocarbon group having at least one carbon-carbon double bond at the main chain (e.g., in the middle) or at the end (e.g., at the end), preferably a C2-C 20 The term "C2-C4-alkenyl" as used herein includes vinyl, propenyl and butenyl. 60 "Alkenylene" refers to a C2-C 60 Alkenyl has a divalent group with substantially the same structure, preferably C2-C 20 Alkenylene or C2-C5 alkenylene.

[0424] As used herein, the term "C2-C 60 "Alkynyl" refers to a C2-C 60 The alkyl group is a monovalent hydrocarbon group having at least one carbon-carbon triple bond at the main chain (e.g., in the middle) or at the end (e.g., at the end), preferably a C2-C 20 Alkynyl, and examples thereof include ethynyl and propynyl. 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.

[0425] As used herein, the term "C1-C 60 "Alkoxy" refers to 101 (where A 101 C1-C 60 A monovalent group represented by an alkyl group, preferably a C1-C 20 Alkoxy group, and examples thereof include methoxy group, ethoxy group and isopropoxy group.

[0426] As used herein, the term "C3-C 10 The term "cycloalkyl" as used herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, and bicyclo[2.2.2]octyl. As used herein, the term "C3-C 10 "Cycloalkylene" refers to a C3-C 10 The cycloalkyl group has a divalent group having substantially the same structure.

[0427] As used herein, the term "C1-C10 The term "heterocycloalkyl" as used herein refers to a monovalent cyclic group which further includes at least one heteroatom as a ring-forming atom in addition to carbon atoms and has 1 to 10 carbon atoms, and is exemplified by 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl, and tetrahydrothienyl. 10 "Heterocycloalkylene" refers to a C1-C 10 The heterocycloalkyl group has a divalent group having substantially the same structure.

[0428] As used herein, the term "C3-C 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and having no aromaticity (e.g., not aromatic), and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C 10 "Cycloalkenylene" refers to a C3-C 10 The cycloalkenyl group is a divalent group having substantially the same structure.

[0429] As used herein, the term "C1-C 10 "Heterocycloalkenyl" refers to a monovalent cyclic group having at least one heteroatom as a ring atom, 1 to 10 carbon atoms and at least one double bond in its ring structure in addition to carbon atoms. 10 Examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. As used herein, the term "C1-C 10 "Heterocycloalkenylene" refers to a C1-C 10 The heterocycloalkenyl group is a divalent group having substantially the same structure.

[0430] As used herein, the term "C6-C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system (having 6 to 60 carbon atoms), and the term "C6-C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system (having 6 to 60 carbon atoms). 60 Examples of aryl groups are fluorenyl, 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 ovalenyl. 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 (eg, bonded together).

[0431] As used herein, the term "C1-C60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom as a ring-forming atom in addition to carbon atoms and having 1 to 60 carbon atoms. As used herein, the term "C1-C 60 "Heteroarylene" refers to a divalent group having a heterocyclic aromatic system which has at least one heteroatom as a ring atom in addition to carbon atoms and has 1 to 60 carbon atoms. 60 Examples of heteroaryl groups are carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, and naphthyridinyl. 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 (eg, bonded to each other).

[0432] 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 (e.g., bound together), with only carbon atoms as ring atoms, and no aromaticity (e.g., the entire molecular structure is not aromatic) in its entire molecular structure. Examples of monovalent non-aromatic fused polycyclic groups are indenyl, spiro-bifluorenyl, benzofluorenyl, indenophenanthryl, and indenoanthryl. As used herein, the term "divalent non-aromatic fused polycyclic group" refers to a divalent group having substantially the same structure as a monovalent non-aromatic fused polycyclic group.

[0433] 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 (e.g., bonded to each other), having at least one heteroatom as a ring-constituting atom in addition to carbon atoms, and having no aromaticity in its entire molecular structure (e.g., the entire molecular structure is not aromatic). Examples of the monovalent non-aromatic fused heteropolycyclic group are pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzosilolyl, benzothienyl, benzofuranyl, dibenzosilolyl, dibenzothienyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzosilolyl, azadibenzothienyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, indenocarbazolyl, indolocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, benzosilolcarbazolyl, benzoindolcarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, benzonaphthosilolyl, benzofuranodibenzofuranyl, benzofuranodibenzothienyl, and benzothienodibenzothienyl. As used herein, the term "divalent non-aromatic fused heteropolycyclic group" refers to a divalent group having substantially the same structure as a monovalent non-aromatic fused heteropolycyclic group.

[0434] As used herein, the term "C6-C 60 "Aryloxy" refers to -OA 102 (where A 102 C6-C 60 aryl), and as used herein, the term "C6-C 60 "Arylthio" refers to -SA 103 (where A 103 C6-C 60 aryl).

[0435] As used herein, the term "R 10a " can be:

[0436] Deuterium (-D), -F, -Cl, -Br, -I, hydroxy, cyano, or nitro;

[0437] Each unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy, C6-C 60 Arylthio, -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;

[0438] Each unsubstituted or substituted C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy or C6-C 60 Arylthio: 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 groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy, C6-C 60 Arylthio, -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

[0439] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q32 ),-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ).

[0440] 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; or 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 group or C1-C 60 Heterocyclic group.

[0441] As used herein, the term "heteroatom" refers to any atom other than a carbon atom. Examples of heteroatoms are O, S, N, P, Si, B, Ge, Se, and any combination thereof.

[0442] As used herein, the term "Ph" refers to a phenyl group, as used herein, the term "Me" refers to a methyl group, as used herein, the term "Et" refers to an ethyl group, as used herein, the term "tert-Bu" or "Bu" refers to an ethyl group. t ” refers to a tert-butyl group, and the term “OMe” as used herein refers to a methoxy group.

[0443] As used herein, the term "biphenyl" refers to a "phenyl group substituted by a phenyl group". In other words, a "biphenyl group" is a group having C6-C 60 A phenyl group substituted with an aryl group as a substituent.

[0444] As used herein, the term "terphenyl" refers to a phenyl group substituted with a biphenyl group. In some embodiments, the terphenyl group is a C6-C 60 Aryl-substituted C6-C 60 A phenyl group substituted with an aryl group as a substituent.

[0445] Unless otherwise defined, * and *' as used herein each refer to a binding site to an adjacent atom in the corresponding formula.

[0446] Hereinafter, the compounds of the embodiment and the light-emitting device according to the embodiment will be described in more detail with reference to Synthesis Examples and Examples. The phrase "replacing A with B" used in describing Synthesis Examples means replacing A with an equal molar equivalent of B.

[0447] Example

[0448] Synthesis Example 1: Synthesis of Compound 1

[0449]

[0450] Synthesis of intermediate 1-1

[0451] N1,N1,N3,N3,N5-pentaphenylbenzene-1,3,5-triamine (1 eq), 5-bromo-1,2,3,4-tetrahydroquinoline (1.1 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene under a nitrogen atmosphere to give tris(dibenzylideneacetone)dipalladium intermediate 1-3 intermediate 1-1. (Yield: 60%)

[0452] Synthesis of intermediate 1-2

[0453] Intermediate 1-1 (1 eq), 5-chloro-N1,N1,N3,N3-tetraphenylbenzene-1,3-diamine (2 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene under a nitrogen atmosphere, and the resulting mixed solution was stirred at a temperature of 100° C. under a nitrogen atmosphere for 12 hours. After cooling, the organic layer obtained by washing the resulting reaction solution three times with ethyl acetate and water was dried using MgSO 4 and dried again under reduced pressure. Subsequently, the resulting product was separated and purified by column chromatography to obtain Intermediate 1-2. (Yield: 60%)

[0454] Synthesis of compound 1

[0455] Intermediate 1-2 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0°C. Then, BBr3 (5 eq) was slowly injected thereinto. The reaction temperature was raised to 150°C, and the resulting mixed solution was stirred under a nitrogen atmosphere for 24 hours. After cooling, triethylamine was slowly added dropwise to the resulting reaction solution to terminate the reaction. Then, the resulting product was added dropwise to ethanol for precipitation, thereby obtaining a reaction product by filtration. The resulting product was purified by column chromatography to obtain compound 1. (Yield: 52%)

[0456] Synthesis Example 2: Synthesis of Compound 2

[0457]

[0458] Synthesis of intermediate 2-1

[0459] 1,3-Dibromo-5-phenoxybenzene (1 eq), diphenylamine (0.9 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), BINAP (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene, and the resulting mixed solution was stirred at 100° C. under a nitrogen atmosphere for 4 hours. After cooling, the organic layer obtained by washing the resulting reaction solution three times with ethyl acetate and water was dried using MgSO 4 and dried again under reduced pressure. Subsequently, the resulting product was separated and purified by column chromatography to obtain Intermediate 2-1. (Yield: 65%)

[0460] Synthesis of intermediate 2-2

[0461] Intermediate 2-1 (1 eq), aniline (1.5 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene, and the resulting mixed solution was stirred at 100° C. under a nitrogen atmosphere for 12 hours. After cooling, the organic layer obtained by washing the resulting reaction solution three times with ethyl acetate and water was dried using MgSO 4 and dried again under reduced pressure. Subsequently, the resulting product was separated and purified by column chromatography to obtain Intermediate 2-2. (Yield: 75%)

[0462] Synthesis of intermediate 2-3

[0463] Intermediate 2-3 was synthesized in essentially the same manner as used to prepare Intermediate 1-1, except that Intermediate 2-2 was used instead of N1,N1,N3,N3,N5-pentaphenylbenzene-1,3,5-triamine. (Yield: 65%)

[0464] Synthesis of intermediate 2-4

[0465] Intermediate 2-4 was synthesized in essentially the same manner as used to prepare Intermediate 1-2, except that Intermediate 2-3 was used instead of Intermediate 1-1. (Yield: 60%)

[0466] Synthesis of compound 2

[0467] Compound 2 was synthesized in essentially the same manner as used to prepare Compound 1, except that Intermediate 2-4 was used instead of Intermediate 1-2. (Yield: 3%)

[0468] Synthesis Example 3: Synthesis of Compound 3

[0469]

[0470] Synthesis of intermediate 3-1

[0471] Intermediate 3-1 was synthesized in essentially the same manner as used to prepare Intermediate 2-2, except that 5-chloro-N1,N1,N3,N3-pentaphenylbenzene-1,3-diamine was used instead of Intermediate 2-1. (Yield: 75%)

[0472] Synthesis of intermediate 3-2

[0473] Intermediate 3-2 was synthesized in essentially the same manner as used to prepare Intermediate 1-1, except that Intermediate 3-1 was used instead of N1,N1,N3,N3,N5-pentaphenylbenzene-1,3,5-triamine. (Yield: 65%)

[0474] Synthesis of intermediate 3-3

[0475] Intermediate 2-1 (1 eq), intermediate 3-2 (0.1 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene, and the resulting mixed solution was stirred at 100° C. under a nitrogen atmosphere for 12 hours. After cooling, the organic layer obtained by washing the resulting reaction solution three times with ethyl acetate and water was dried using MgSO 4 and dried again under reduced pressure. Subsequently, the resulting product was separated and purified by column chromatography to obtain intermediate 3-3. (Yield: 65%)

[0476] Synthesis of compound 3

[0477] Compound 3 was synthesized in essentially the same manner as used to prepare compound 1, except that intermediate 3-3 was used instead of intermediate 1-2. (Yield: 3%)

[0478] Synthesis Example 4: Synthesis of Compound 4

[0479]

[0480] Synthesis of intermediate 4-1

[0481] 3,5-bis(diphenylamino)phenol (1 eq), 5-fluoro-1,2,3,4-tetrahydroquinoline (1.5 eq) and K 3 PO 4 (2 eq) were dissolved in DMF, and the resulting mixed solution was stirred at 160° C. for 12 hours. After cooling, the solvent was removed therefrom under reduced pressure, and the resulting product was washed three times with dichloromethane and water, and the organic layer obtained by separation was dried using MgSO 4 and dried again under reduced pressure. Subsequently, the resulting product was separated and purified by column chromatography to obtain Intermediate 4-1. (Yield: 60%)

[0482] Synthesis of intermediate 4-2

[0483] Intermediate 4-2 was synthesized in essentially the same manner as used to prepare Intermediate 1-2, except that Intermediate 4-1 was used instead of Intermediate 1-1. (Yield: 60%)

[0484] Synthesis of compound 4

[0485] Compound 4 was synthesized in essentially the same manner as used to prepare compound 1, except that intermediate 4-2 was used instead of intermediate 1-2. (Yield: 6%)

[0486] Synthesis Example 5: Synthesis of Compound 8

[0487]

[0488] Synthesis of intermediate 8-1

[0489] Intermediate 8-1 was synthesized in essentially the same manner as used to prepare Intermediate 3-1, except that [1,1'biphenyl]-2-amine was used instead of aniline. (Yield: 70%)

[0490] Synthesis of intermediate 8-2

[0491] Intermediate 8-2 was synthesized in essentially the same manner as used to prepare Intermediate 1-1, except that Intermediate 8-1 was used instead of N1,N1,N3,N3,N5-pentaphenylbenzene-1,3,5-triamine. (Yield: 55%)

[0492] Synthesis of compound 8

[0493] Compound 8 was synthesized in essentially the same manner as used to prepare compound 1, except that intermediate 8-2 was used instead of intermediate 1-2. (Yield: 11%)

[0494] Synthesis Example 6: Synthesis of Compound 16

[0495]

[0496] Synthesis of intermediate 16-1

[0497] Intermediate 16-1 was synthesized in essentially the same manner as used to prepare Intermediate 2-1, except that 1,3-dibromo-5-chlorobenzene was used instead of 1,3-dibromo-5-phenoxybenzene. (Yield: 60%)

[0498] Synthesis of intermediate 16-2

[0499] Intermediate 16-1 (1 eq), 1,2,3,4-tetrahydroquinoline (1.5 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene, and the resulting mixed solution was stirred at 100° C. under a nitrogen atmosphere for 12 hours. After cooling, the organic layer obtained by washing the resulting reaction solution three times with ethyl acetate and water was dried using MgSO 4 and dried again under reduced pressure. Subsequently, the resulting product was separated and purified by column chromatography to obtain Intermediate 16-2. (Yield: 65%)

[0500] Synthesis of intermediate 16-3

[0501] Intermediate 16-2 (1 eq), 5-bromo-1,2,3,4-tetrahydroquinoline (1.5 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene, and the resulting mixed solution was stirred at 100° C. under a nitrogen atmosphere for 12 hours. After cooling, the organic layer obtained by washing the resulting reaction solution three times with ethyl acetate and water was dried using MgSO 4 and dried again under reduced pressure. Subsequently, the resulting product was separated and purified by column chromatography to obtain Intermediate 16-3. (Yield: 55%)

[0502] Synthesis of intermediate 16-4

[0503] Intermediate 16-4 was synthesized in essentially the same manner as used to prepare Intermediate 16-3, except that aniline was used instead of 5-bromo-1,2,3,4-tetrahydroquinoline. (Yield: 60%)

[0504] Synthesis of intermediate 16-5

[0505] Intermediate 16-3 (1 eq), Intermediate 16-4 (1.3 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene, and the resulting mixed solution was stirred at 100° C. under a nitrogen atmosphere for 12 hours. After cooling, the organic layer obtained by washing the resulting reaction solution three times with ethyl acetate and water was dried using MgSO 4 and dried again under reduced pressure. Subsequently, the resulting product was separated and purified by column chromatography to obtain Intermediate 16-5. (Yield: 60%)

[0506] Synthesis of compound 16

[0507] Compound 16 was synthesized in essentially the same manner as used to prepare compound 1, except that intermediate 16-5 was used instead of intermediate 1-2. (Yield: 15%)

[0508] The compounds were synthesized according to Synthesis Examples 1 to 6. 1 H NMR and MS / FAB are shown in Table 1. By referring to the above synthetic routes and source materials, those skilled in the art will easily know the synthesis of other compounds besides the compounds shown in Table 1.

[0509] Table 1

[0510]

[0511] Example 1

[0512] As the anode, Corning 15Ω / cm 2 The ITO glass substrate was cut into a size of 50 mm×50 mm×0.7 mm, cleaned by ultrasonication with isopropyl alcohol and pure water for 5 minutes each, and then exposed to ultraviolet rays and ozone for 30 minutes. The ITO glass substrate was provided to a vacuum deposition apparatus.

[0513] NPD was vacuum deposited on the ITO anode formed on the ITO glass substrate to form a A hole injection layer is formed by vacuum depositing HT3 on the hole injection layer to form a hole injection layer having a thickness of The first hole transport layer.

[0514] CzSi as a hole transport compound was vacuum deposited on the first hole transport layer to form a layer with a thickness of a second hole transport layer.

[0515] mCP (host) and compound 1 (dopant) were co-deposited on the second hole transport layer at a weight ratio of 99:1 to form a layer with a thickness of The emission layer.

[0516] Subsequently, TSPO1 is deposited on the emission layer to form a thickness of The buffer layer is formed by depositing TPBI on the buffer layer to form a thickness of electron transport layer.

[0517] LiF as an alkali metal halide is deposited on the electron transport layer to form a layer with a thickness of The electron injection layer is vacuum deposited on Al to form a layer with a thickness of HT28 was vacuum deposited on the LiF / Al electrode to form a LiF / Al electrode with a thickness of The capping layer is formed to complete the manufacture of the light-emitting device.

[0518]

[0519] Examples 2 to 12 and Comparative Examples 1 to 6

[0520] Light-emitting devices were manufactured in substantially the same manner as in Example 1, except that the materials shown in Table 2 were used instead of HT3 when forming the first hole transport layer, and the compounds shown in Table 2 were used instead of Compound 1 when forming the emission layer.

[0521] Evaluation Example 1

[0522] In order to evaluate the characteristics of the light emitting devices of Examples 1 to 12 and Comparative Examples 1 to 6, the current density at 10 mA / cm 2 The driving voltage, luminous efficiency and maximum external quantum efficiency (EQE) under . The driving voltage of the light-emitting device was measured using a source meter (Keithley Instrument, 2400 series), and the maximum EQE was measured using an external quantum efficiency measurement device C9920-2-12 from Hamamatsu Photonics Inc. When evaluating the maximum EQE, the luminance / current density was measured using a luminance meter calibrated for wavelength sensitivity, and the maximum EQE was converted assuming that an angular luminance distribution (Lambertian) was obtained relative to a completely diffuse reflection surface. The characteristic evaluation results of the light-emitting device are shown in Table 2.

[0523] Table 2

[0524]

[0525]

[0526] Referring to Table 2, it can be seen that the light-emitting devices of Examples 1 to 12 have reduced driving voltage, increased luminous efficiency, or increased maximum EQE, compared to the light-emitting devices of Comparative Examples 1 to 6.

[0527] According to one or more embodiments, the light emitting device may have low driving voltage, high efficiency, and long lifespan, and in this regard, such a light emitting device may be used to manufacture high-quality electronic devices.

[0528] It should be understood that the embodiments described herein should be considered only as descriptive and not for the purpose of limitation. The description of features or aspects in each embodiment should generally be considered to be applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the drawings, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of this disclosure as defined by the appended claims and their equivalents.

Claims

1. A light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; as well as an intermediate layer between the first electrode and the second electrode and including an emission layer, wherein the intermediate layer further comprises a hole transport region between the first electrode and the emissive layer, The hole transport region includes a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof, and The emission layer includes at least one heterocyclic compound represented by Formula 1: Formula 1 Formula 201 Formula 202 In formula 1, X2 is O, S, Se or N (Z 2a ), X3 is O, S, Se or N(Z 3a ), X4 is O, S, Se or N(Z 4a) , Ring CY1 to Ring CY4 are each independently C3-C 60 Carbocyclic groups, R0 and R3 to R5 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by at least one R 10a Substituted C1-C 60 Alkyl is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy, R1, R2, Z 2a 、Z 3a and Z 4a 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 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, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), a1 to a4 are each independently an integer selected from 0 to 20, a56 is an integer selected from 0 to 6, Z 2a Optionally linked to R2 to form an unsubstituted or substituted 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, R 10a for: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, or nitro; Each unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy, C6-C 60 Arylthio, -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 groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy or C6-C 60 Arylthio: 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 groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy, C6-C 60 Arylthio, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 ),-C(=O)(Q 21 )、-S(=O)2(Q 21 ),-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ),and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each independently represents: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 Alkoxy; or each unsubstituted or deuterated, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C substituted by alkoxy, phenyl, biphenyl or any combination thereof 60 Carbocyclic group or C1-C 60 Heterocyclic groups, Among them, in Equation 201 and Equation 202, L 201 To L 204 are each independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic groups, L 205 For *-O-*', *-S-*', *-N(Q 201 )-*', unsubstituted or replaced by at least one R 10a Substituted C1-C 20 Alkylene is either unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic groups, xa1 to xa4 are each independently an integer selected from 0 to 5, xa5 is an integer selected from 1 to 10, R 201 to R 204 and Q 201 are each independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, R 201 and R 202 Optionally, through a single bond, unsubstituted or substituted 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, na1 is an integer selected from 1 to 4, and * and *' each indicate a binding site with an adjacent atom.

2. The light emitting device according to claim 1, wherein: The first electrode is an anode, The second electrode is a cathode, The intermediate layer further includes an electron transport region between the emissive layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer or any combination thereof, and The electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer or any combination thereof.

3. The light emitting device according to claim 2, wherein: At least one selected from the hole transport region and the emissive layer comprises an aromatic amine-containing compound, an acridine-containing compound, a carbazole-containing compound, or any combination thereof; or At least one selected from the emission layer and the electron transport region includes a silicon-containing compound, a phosphine oxide-containing compound, a sulfur oxide-containing compound, a phosphorus oxide-containing compound, a triazine-containing compound, a pyrimidine-containing compound, a pyridine-containing compound, a dibenzofuran-containing compound, a dibenzothiophene-containing compound, or any combination thereof.

4. The light-emitting device according to claim 1, wherein X2 is O or N (Z 2a ). 5 . The light-emitting device according to claim 1 , wherein ring CY 1 to ring CY 4 are each independently phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, indenyl, or fluorenyl. The light-emitting device according to claim 1 , wherein at least one selected from ring CY 1 to ring CY 4 is a phenyl group.

7. The light emitting device according to claim 1, wherein R0 and R3 to R5 are each independently: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, or nitro; or Each unsubstituted or substituted C1-C 20 Alkyl or C1-C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, -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 ),-P(=O)(Q 31 )(Q 32) or any combination thereof, R1, R2, Z 2a 、Z 3a 、Z 3b and Z 4a Each independently is: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; Each unsubstituted or substituted C1-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl or C1-C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, -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 ),-P(=O)(Q 31 )(Q 32) or any combination thereof; each unsubstituted or substituted by cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzo thiophene, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophene, azafluorenyl, azadibenzosilacyclopentadienyl, piperidinyl, acridinyl, phenothiazinyl, 1,2,3,4-tetrahydroquinolinyl or phenoxazinyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indole yl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -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 ),-P(=O)(Q 31 )(Q 32) or any combination thereof; or -B(Q 1) (Q2), -P(Q1)(Q2) or -C(=O)(Q1). The light-emitting device according to claim 1 , wherein ring CY1 and ring CY2 are identical to each other.

9. The light-emitting device of claim 1 , wherein the emission layer comprises at least one heterocyclic compound represented by any one of Formulas 1A to 1D: in, In Formula 1A to Formula 1D, X2 to X4, ring CY1 to ring CY4, R0 to R5, a1 to a4 and a56 are each the same as described in claim 1, X 2A N(Z 2a ), X 3B N(Z 3a ), X 4C N(Z 4a ), Ring CY6 to Ring CY8 are each the same as described in conjunction with Ring CY1 in claim 1, R6 to R8 are each the same as described in conjunction with R1 in claim 1, and a6 to a8 are each the same as described in conjunction with a1 in claim 1 .

10. The light-emitting device of claim 1, wherein the emission layer comprises at least one heterocyclic compound represented by any one of Formulas 1A-1 to 1D-1: in, In Formula 1A-1 to Formula 1D-1: X2 to X4, ring CY1 to ring CY4, R0 to R5, a1 to a4 and a56 are each the same as described in claim 1, X 2A N(Z 2a ), X 3B N(Z 3a ), X 4C N(Z 4a ), R6 to R8 are each the same as described in conjunction with R1 in claim 1, a66 is the same as described in conjunction with a56 in claim 1, and a74 and a84 are each independently an integer selected from 0 to 4.

11. The light-emitting device of claim 1 , wherein the emission layer comprises at least one heterocyclic compound selected from Compounds 1 to 40: The light-emitting device of claim 1 , wherein the emission layer emits blue light or blue-green light. 13 . The light-emitting device according to claim 1 , wherein the emission layer has a lowest excited triplet energy level of equal to or greater than 2.5 eV and equal to or less than 3.0 eV.

14. The light emitting device according to claim 1, wherein: The light emitting device further includes a second capping layer outside the second electrode, and The second capping layer includes one selected from carbocyclic compounds, heterocyclic compounds, amino-containing compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, alkaline earth metal complexes, or any combination thereof. 15 . The light emitting device of claim 1 , wherein the heterocyclic compound represented by Formula 1 included in the emission layer serves as a delayed fluorescence dopant to emit delayed fluorescence from the emission layer.

16. A light emitting device comprising: a first electrode; a second electrode facing the first electrode; as well as an intermediate layer between the first electrode and the second electrode and including an emission layer, The light emitting device further comprises a second capping layer outside the second electrode, the second capping layer having a refractive index equal to or greater than 1.6, and The emission layer includes at least one heterocyclic compound represented by Formula 1: Formula 1 In formula 1, X2 is O, S, Se or N (Z 2a ), X3 is O, S, Se or N(Z 3a ), X4 is O, S, Se or N(Z 4a) , Ring CY1 to Ring CY4 are each independently C3-C 60 Carbocyclic groups, R0 and R3 to R5 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by at least one R 10a Substituted C1-C 60 Alkyl is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy, R1, R2, Z 2a 、Z 3a , and Z 4a 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 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, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), a1 to a4 are each independently an integer selected from 0 to 20, a56 is an integer selected from 0 to 6, Z 2a Optionally linked to R2 to form an unsubstituted or substituted R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, R 10a Selected from: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, or nitro; Each unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy, C6-C 60 Arylthio, -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 groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy or C6-C 60 Arylthio: 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 groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy, C6-C 60 Arylthio, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 ),-C(=O)(Q 21 )、-S(=O)2(Q 21 ),-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ),and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each independently represents: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 Alkoxy; or each unsubstituted or deuterated, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C substituted by alkoxy, phenyl, biphenyl or any combination thereof 60 Carbocyclic group or C1-C 60 Heterocyclic group. The light emitting device of claim 16 , wherein the encapsulation portion is on the second capping layer.

18. The light emitting device according to claim 17, wherein the packaging portion comprises: an inorganic film comprising silicon nitride, silicon oxide, 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, acrylic resin, epoxy resin, or any combination thereof; or A combination of the inorganic film and the organic film.

19. An electronic device comprising the light emitting device according to any one of claims 1 to 18, wherein The electronic device further comprises a thin film transistor, The thin film transistor includes a source electrode and a drain electrode, and The first electrode of the light emitting device is electrically coupled to the source electrode or the drain electrode of the thin film transistor.

20. The electronic device of claim 19, wherein the electronic device further comprises a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.

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