Heterocyclic compound and organic light-emitting device including the same

Abstract

Provided are a heterocyclic compound and an organic light-emitting device including the heterocyclic compound. The heterocyclic compound can be represented by Formula 1: #imgabs0# In Formula 1, A 1 , X 2 , Y 1 , Y 2 、m1、m2、R 10 , R 20 , R 30 , b10, b20 and b30 are the same as described in the specification.

Description

[0001] The Korean Patent Application No. 10-2018-0165472 filed on December 19, 2018 in the Korean Intellectual Property Office, entitled “Heterocyclic Compound and Organic Light-Emitting Device Including the Same” is hereby incorporated by reference in its entirety. Technical Field

[0002] Embodiments relate to a heterocyclic compound and an organic light emitting device including the heterocyclic compound. Background Art

[0003] The organic light emitting device is a self-emissive device that produces full-color images, and also has wide viewing angles, high contrast, short response times, and excellent characteristics in terms of brightness, driving voltage, and response speed compared to devices in the art.

[0004] An example of such an organic light-emitting device may include a first electrode disposed on a substrate and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially disposed on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers such as holes and electrons recombine in the emission layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light. Summary of the invention

[0005] The embodiment relates to an organic light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; and an organic layer located between the first electrode and the second electrode and including an emission layer, the organic layer including a heterocyclic compound represented by Formula 1:

[0006] <Formula 1>

[0007]

[0008] Among them, in formula 1,

[0009] A 1 It may be a group represented by Formula 2,

[0010] <Formula 2>

[0011]

[0012] In equation 1 and equation 2,

[0013] X 1 Can be O, S or N (R 3 ),

[0014] X 2 Can be O, S, N (R 4 )、C(R 4 )(R 5 ) or Si(R 4 )(R 5 ),

[0015] Y 1 and Y 2 can be independently C(R 6 )(R 7 ) or Si(R 6 )(R 7 ),

[0016] m1 can be 0 or 1,

[0017] m2 can be 0 or 1,

[0018] R 3 It may be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-N(Q 1 )(Q 2 )、-P(=O)(Q 1 )(Q 2 ) or -S(=O) 2 (Q 1 ),

[0019] R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 10 , R 20 and R 30 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-N(Q 1 )(Q 2 )、-P(=O)(Q 1 )(Q 2 ) or -S(=O) 2 (Q 1 ),

[0020] R 1 To R 7 , R10 , R 20 and R 30 Two or more adjacent substituents in may be linked to form a substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,

[0021] When m1 and m2 are both 1, R 1 and R 2 Can be linked to form substituted or unsubstituted C 7 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,

[0022] b10, b20 and b30 may each independently be an integer from 1 to 4,

[0023] Substituted C 5 -C 60 Carbocyclic, substituted C 7 -C 60 Carbocyclic, substituted C 1 -C 60 Heterocyclic, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60At least one substituent in the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:

[0024] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy;

[0025] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) or -P(=O)(Q 11 )(Q 12 ) 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy;

[0026] C 3 -C 10 Cycloalkyl, C1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic condensed heteropolycyclic group;

[0027] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) or -P(=O)(Q 21 )(Q 22 ) 3 -C 10 Cycloalkyl, C 1-C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic condensed heteropolycyclic group; or

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

[0029] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group or a terphenyl group.

[0030] The embodiment also relates to a heterocyclic compound represented by Formula 1. BRIEF DESCRIPTION OF THE DRAWINGS

[0031] Features will become apparent to those skilled in the art by describing in detail example embodiments with reference to the accompanying drawings, in which:

[0032] Figure 1 shows a schematic diagram of an organic light emitting device according to an example embodiment;

[0033] Figure 2 shows a schematic diagram of an organic light emitting device according to another example embodiment;

[0034] Figure 3 A schematic diagram showing an organic light emitting device according to another example embodiment; and

[0035] Figure 4 A schematic diagram of an organic light emitting device according to another example embodiment is shown. DETAILED DESCRIPTION

[0036] Example embodiments will now be described more fully below with reference to the accompanying drawings; however, example embodiments may be implemented in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete and will fully convey example implementations to those skilled in the art. In the accompanying drawings, the sizes of layers and regions may be exaggerated for clarity of illustration. The same reference numerals represent the same elements throughout.

[0037] As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise.

[0038] It will also be understood that the term “comprises” and / or variations thereof used herein specify the presence of stated features or components, but do not preclude the presence or addition of one or more other features or components.

[0039] It will be understood that when a layer, region or component is referred to as being "on" or "onto" another layer, region or component, the layer, region or component may be formed directly or indirectly on the other layer, region or component. That is, for example, there may be intervening layers, regions or components.

[0040] Example embodiments relate to a heterocyclic compound represented by Formula 1:

[0041] <Formula 1>

[0042]

[0043] In formula 1, A 1 It may be a group represented by Formula 2:

[0044] <Formula 2>

[0045]

[0046] In formula 2, X 1 Can be O, S or N (R 3 ).

[0047] In an exemplary embodiment, A in Formula 1 1 It can be expressed by one of the equations 2-1 to 2-3:

[0048]

[0049] In Formula 2-1 to Formula 2-3,

[0050] X 1 Same as described above,

[0051] X 11 Can be N or C (R 51 ), X 12 Can be N or C (R 52 ), X 13 Can be N or C (R 53 ), X 14 Can be N or C (R 54 ),

[0052] X 21 Can be N or C (R 61 ), X 22 Can be N or C (R 62 ), X 23 Can be N or C (R 63 ), X 24 Can be N or C (R 64 ), X 25 Can be N or C (R 65 ), X 26 Can be N or C (R 66 ), X 27 Can be N or C (R 67 ), X 28 Can be N or C (R 68 ),

[0053] When m1 and m2 in formula 1 are both 1, X 11 To X 14 At least one of can be N, and

[0054] * indicates the binding site with the adjacent atom.

[0055] R 41 , R 42 , R 51 To R 54 and R 61 To R 68 can all independently be:

[0056] hydrogen, deuterium, -F, -Cl, -Br, -I, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, ethenyl, propenyl, butenyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy;

[0057] methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy, all of which are substituted with deuterium, -F, -Cl, -Br, -I, cyano, phenyl or biphenyl; or

[0058] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thirolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothirolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl , tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzosilyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthosilyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazopyridyl, benzonaphthyridinyl, azafluorenyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzosilyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl or indolocarbazolyl.

[0059] In formula 1, X 2 Can be O, S, N (R 4 )、C(R 4 )(R 5 ) or Si(R 4 )(R 5 ).

[0060] In formula 1, Y 1 and Y 2 can be independently C(R 6 )(R 7 ) or Si(R 6 )(R 7 ), m1 can be 0 or 1, and m2 can be 0 or 1.

[0061] In example embodiments, in Formula 1, m1 and m2 may both be 0, or m1 and m2 may both be 1.

[0062] When m1 in formula 1 is 0, Y 1 For example, when m1 is 0, Formula 1 can be represented by Formula 1A:

[0063] <Formula 1A>

[0064]

[0065] When m2 in formula 1 is 0, Y 2 For example, when m2 is 0, Formula 1 can be expressed by Formula 1B:

[0066] <Formula 1B>

[0067]

[0068] In an example embodiment, when m1 and m2 are both 0, Formula 1 may be represented by Formula 1C:

[0069] <Formula 1C>

[0070]

[0071] In an example embodiment, when m1 and m2 are both 1, Formula 1 may be represented by Formula 1D:

[0072] <Formula 1D>

[0073]

[0074] In Formula 1A to Formula 1D,

[0075] A 1 , X 2 , Y 1 , Y 2、m1、m2、R 10 , R 20 , R 30 , b10, b20 and b30 are the same as described above.

[0076] In formula 2, R 3 It may be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-N(Q 1 )(Q 2 )、-P(=O)(Q 1 )(Q 2 ) or -S(=O) 2 (Q 1 ).

[0077] In an exemplary embodiment, R 3 Can be:

[0078] hydrogen, deuterium, -F, -Cl, -Br, -I, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, ethenyl, propenyl, butenyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy;

[0079] methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy, all substituted with deuterium, -F, -Cl, -Br, -I, cyano, phenyl or biphenyl;

[0080] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl or pentacene; or

[0081] are substituted with deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrene, yl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thirolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl yl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthothioyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazopyridyl, benzonaphthyridinyl, azafluorenyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzothioyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl, indolocarbazolyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or -P(=S)(Q 31 )(Q 32 ) of cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl or pentacene.

[0082] In an exemplary embodiment, R 3 Can be:

[0083] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;

[0084] C substituted with deuterium, -F, -Cl, -Br, -I, cyano, phenyl or biphenyl 1 -C 20 Alkyl or C 1 -C 20 Alkoxy; or

[0085] A group represented by one of Formula 7-1 to Formula 7-12:

[0086]

[0087] In equations 7-1 to 7-12,

[0088] Z 51 and Z 52 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkenyl, C 1 -C 20 Alkynyl, C 1 -C 20alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, phenanthryl, anthracenyl, benzo[9,10]phenanthryl, pyridyl, pyrimidinyl, carbazolyl or triazinyl,

[0089] g3 can be an integer from 1 to 3,

[0090] g4 can be an integer from 1 to 4,

[0091] g5 can be an integer from 1 to 5,

[0092] g6 can be an integer from 1 to 6,

[0093] g7 can be an integer from 1 to 7,

[0094] g9 can be an integer from 1 to 9, and

[0095] *Indicates the binding site with the adjacent atom.

[0096] In equations 1 and 2, R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 10 , R 20 and R 30 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-N(Q 1 )(Q 2 )、-P(=O)(Q 1 )(Q 2 ) or -S(=O) 2 (Q 1 ),and

[0097] R 1 To R 7 , R 10 , R 20 and R 30 Two or more adjacent substituents may be linked to form a substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group.

[0098] In Formula 1, b10, b20, and b30 may each independently be an integer of 1 to 4.

[0099] In an exemplary embodiment, R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 10 , R 20 and R 30 can all independently be:

[0100] hydrogen, deuterium, -F, -Cl, -Br, -I, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, ethenyl, propenyl, butenyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, or tert-butoxy; or

[0101] A group represented by one of Formula 5-1 to Formula 5-26 and Formula 6-1 to Formula 6-55, and

[0102] R 1 , R 2 , R 4 , R 5 , R 6 , R7 , R 10 , R 20 and R 30 Two or more adjacent substituents may be linked to form a substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group:

[0103]

[0104]

[0105]

[0106]

[0107] In Formulas 5-1 to 5-26 and 6-1 to 6-55,

[0108] Y 31 and Y 32 Can be O, S, C (Z 34 )(Z 35 )、N(Z 34 ) or Si(Z 34 )(Z 35 ),

[0109] Z 31 , Z 32 , Z 34 and Z 35 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkenyl, C 1 -C 20 Alkynyl, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, phenanthryl, anthracenyl, benzo[9,10]phenanthryl, pyridyl, pyrimidinyl, carbazolyl or triazinyl,

[0110] e2 can be 1 or 2,

[0111] e3 can be an integer from 1 to 3,

[0112] e4 can be an integer from 1 to 4,

[0113] e5 can be an integer from 1 to 5,

[0114] e6 can be an integer from 1 to 6,

[0115] e7 can be an integer from 1 to 7,

[0116] e9 can be an integer from 1 to 9, and

[0117] *Indicates the binding site with the adjacent atom.

[0118] In an exemplary embodiment, R 1 and R 2 may each independently be a group represented by one of Formulae 5-1 to 5-26 and 6-1 to 6-55, and

[0119] R 1 and R 2 can be linked to form a cyclic group, the cyclic group being:

[0120] Phenyl, naphthyl, phenanthrenyl, anthracenyl, benzo[9,10]phenanthrenyl, pyrenyl, quinolyl, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, 2,6-naphthyridinyl, 1,8-naphthyridinyl, 1,5-naphthyridinyl, 1,6-naphthyridinyl, 1,7-naphthyridinyl, 2,7-naphthyridinyl, quinoxalinyl, quinazolinyl, phenanthridinyl or phenanthrolinyl; or

[0121] phenyl, naphthyl, phenanthrenyl, anthracenyl, benzo[9,10]phenanthrenyl, pyrenyl, substituted with deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy, 1,7-naphthyridinyl, 2,7-naphthyridinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, or phenanthrolinyl.

[0122] In an exemplary embodiment, R 4 and R 5 can all independently be:

[0123] hydrogen, deuterium, -F, -Cl, -Br, -I, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, ethenyl, propenyl, butenyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy;

[0124] methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, vinyl, propenyl, butenyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy, all substituted with deuterium, -F, -Cl, -Br, -I, cyano, phenyl or biphenyl;

[0125] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentacene, carbazolyl, dibenzofuranyl, dibenzothiophenyl or dibenzosilyl; or

[0126] cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentacene, carbazolyl, dibenzofuranyl, dibenzothiophenyl or dibenzosilyl, and

[0127] R 4 and R 5 can be linked to form a group represented by Formula 9:

[0128] <Formula 9>

[0129]

[0130] In formula 9,

[0131] X 20 It can be X of formula 1 2 C or Si in

[0132] X 91 Can be single bond, O, S, Se, N(R 93 )、B(R 93 )、C(R 93 )(R 94 ) or Si(R 93 )(R 94 ),

[0133] A91 and A 92 may each independently be benzene, naphthalene, phenanthrene, anthracene, pyridine, pyrazine, pyrimidine, quinoline, isoquinoline, benzoquinoline, benzoisoquinoline, dibenzofuran, dibenzothiophene, fluorene or carbazole,

[0134] R 91 To R 94 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),

[0135] Q 1 To Q 3 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group or a terphenyl group, and

[0136] b91 and b92 may each independently be an integer of 1 to 10.

[0137] In an exemplary embodiment, A in Equation 9 91 and A 92 Each of them may independently be benzene, naphthalene, phenanthrene, anthracene, dibenzofuran, dibenzothiophene, fluorene or carbazole.

[0138] In an exemplary embodiment, R in Equation 9 91 To R 94 and tert-butyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentacene, carbazolyl, dibenzofuranyl, dibenzothiophenyl or dibenzosilyl.

[0139] In an exemplary embodiment, R 6 and R 7may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, vinyl, propenyl, butenyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy; or

[0140] Methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, vinyl, propenyl, butenyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy, all of which are substituted with deuterium, -F, -Cl, -Br, -I, cyano, phenyl or biphenyl.

[0141] In an exemplary embodiment, R 10 , R 20 and R 30 can all independently be:

[0142] hydrogen, deuterium, -F, -Cl, -Br, -I, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl;

[0143] methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl, all of which are substituted with deuterium, -F, -Cl, -Br, -I, cyano, phenyl or biphenyl;

[0144] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl or dibenzosilyl;

[0145] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, carbazolyl, dibenzofuranyl, dibenzothienyl or dibenzothiophenyl substituted with deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, carbazolyl, dibenzofuranyl, dibenzothienyl or dibenzothiophenyl; or

[0146] -N(Q 11 )(Q 12 ),and

[0147] Q 11 and Q 12 Same as described above.

[0148] In example embodiments, the heterocyclic compound represented by Formula 1 may be represented by Formula 10A or Formula 10B:

[0149] <Formula 10A>

[0150]

[0151] <Formula 10B>

[0152]

[0153] In Formula 10A and Formula 10B,

[0154] A 1 and X 2 Same as described above,

[0155] R 11 To R 14 can be independently related to R 10 The same definition,

[0156] R 21 To R 24 can be independently related to R 20 The same definition,

[0157] R 31 To R 34 can be independently related to R 30 The same definition,

[0158] R 61 and R 62 can be independently related to R 6 are defined identically, and

[0159] R 71 and R 72 can be independently related to R 7 The definition is the same.

[0160] In example embodiments, the heterocyclic compound may be one of Compound 1 to Compound 94:

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167] According to example embodiments, the heterocyclic compound includes A in Formula 1 1The electron acceptor part represented by and the electron donor part represented by the core structure in Formula 1. Without being bound by theory, it is believed that in such a structure, the intermolecular charge movement is promoted, thereby improving the luminous efficiency. In addition, since a dipole is formed from the electron donor part to the electron acceptor part, the dipole moment in the molecule increases, thereby further improving the luminous efficiency.

[0168] In addition, in heterocyclic compounds, the electron donor moiety and the electron acceptor moiety are separated from each other. Without being bound by theory, it is believed that in such a structure, the orbital overlap in the molecule can be effectively prevented. Therefore, since the singlet and triplet states of the molecule do not overlap, the heterocyclic compound can have a very low ΔE st In this way, since reverse intersystem crossing from a triplet excited state to a singlet excited state is possible by thermal activity even at room temperature, delayed fluorescence can be emitted. Since light is emitted using excitons having a triplet state, luminous efficiency can be improved.

[0169] In addition, without being bound by theory, it is believed that since the heterocyclic compound has a relatively high hole or electron transport capability, the exciton formation rate in the emission layer can be improved in an organic light-emitting device including the heterocyclic compound represented by Formula 1. Therefore, the organic light-emitting device can have low driving voltage, high efficiency, long life, and high maximum quantum efficiency.

[0170] The synthesis method of the heterocyclic compound represented by Formula 1 will be apparent to those skilled in the art by referring to the following examples.

[0171] At least one of the heterocyclic compounds of Formula 1 may be used between a pair of electrodes of an organic light-emitting device. For example, the heterocyclic compound may be included in at least one layer selected from a hole transport region, an electron transport region, and an emission layer. In example embodiments, the heterocyclic compound of Formula 1 may be used as a material for a capping layer positioned outside a pair of electrodes of an organic light-emitting device.

[0172] According to example embodiments, an organic light emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode. The organic layer may include an emission layer. The organic layer may include at least one heterocyclic compound represented by Formula 1.

[0173] The expression “(organic layer) includes at least one heterocyclic compound” used herein may include the case where “(organic layer) includes the same heterocyclic compound represented by Formula 1” and the case where “(organic layer) includes two or more different heterocyclic compounds represented by Formula 1”.

[0174] For example, the organic layer may include only Compound 1 as a heterocyclic compound. In this regard, Compound 1 may be present in the emission layer of the organic light-emitting device. In example embodiments, the organic layer may include Compound 1 and Compound 2 as heterocyclic compounds. In this regard, Compound 1 and Compound 2 may be present in the same layer (for example, Compound 1 and Compound 2 may both be present in the emission layer), or may be present in different layers (for example, Compound 1 may be present in the emission layer, and Compound 2 may be present in the electron transport layer).

[0175] In an example embodiment, the first electrode may be an anode, the second electrode may be a cathode, the organic layer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, the hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or a combination thereof.

[0176] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0177] In example embodiments, an emission layer of an organic light emitting device may include a heterocyclic compound.

[0178] In example embodiments, an emission layer of an organic light emitting device includes a heterocyclic compound, the heterocyclic compound included in the emission layer is a thermally activated delayed fluorescence emitter (TADF emitter), and the emission layer may emit delayed fluorescence.

[0179] In example embodiments, the emission layer may consist of (or include) a heterocyclic compound, or the emission layer may further include a host. The amount of the heterocyclic compound may be in a range of about 0.1 parts by weight to about 50 parts by weight based on 100 parts by weight of the emission layer.

[0180] For example, the emission layer may be composed of (or include) a heterocyclic compound, the heterocyclic compound may be a TADF emitter, and the TADF emitter may satisfy Formula 1:

[0181] <Formula 1>

[0182] │E D,S1 -E D,T1 │≤0.3eV.

[0183] In formula 1,

[0184] E D,S1 is the singlet energy level of the TADF emitter (eV), and

[0185] E D,T1 is the triplet energy level of the TADF emitter (eV).

[0186] Without being bound by theory, it is believed that because the singlet energy level (E D,S1 ) and triplet energy level (E D,T1 ) is about 0.3 eV or less, so the singlet excitons and triplet excitons generated by the electric field can be easily converted to the intermediate state. Therefore, the organic light-emitting device including the heterocyclic compound can have excellent light-emitting efficiency.

[0187] In example embodiments, the emission layer may include a heterocyclic compound and a host, the heterocyclic compound may be a TADF emitter, and the TADF emitter and the host may satisfy Formula 2 or Formula 3.

[0188] <Formula 2>

[0189] │E H,HOMO -E D,HOMO │≤0.5eV

[0190] <Formula 3>

[0191] │E H,LUMO -E D,LUMO │≤0.5eV.

[0192] In Formula 2 and Formula 3,

[0193] E H,HOMO is the highest occupied molecular orbital (HOMO) energy level of the host (eV),

[0194] E D,HOMO is the HOMO level of the dopant (eV),

[0195] E H,LUMO is the lowest unoccupied molecular orbital (LOMO) energy level of the host (eV),

[0196] E D,LUMO is the LOMO level of the dopant (eV).

[0197] Without being bound by theory, it is believed that since the difference in HOMO energy level or LUMO energy level between the TADF emitter (i.e., the heterocyclic compound represented by Formula 1) and the host is about 0.5 eV or less, charge transfer from the host to the TADF emitter is facilitated. Therefore, an organic light-emitting device including the heterocyclic compound and the host can have excellent luminous efficiency.

[0198] In the emission layer, the host may include at least one selected from anthracene-based compounds, pyrene-based compounds, spirobifluorene-based compounds, carbazole-based compounds, benzimidazole-based compounds, and phosphine oxide-based compounds.

[0199] In example embodiments, an emission layer in an organic light emitting device may include a heterocyclic compound, and the emission layer may emit blue light having a maximum emission wavelength in the range of about 400 nm to about 500 nm.

[0200] In example embodiments, a hole transport region of an organic light emitting device may include a p-dopant, and the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of about −3.5 eV or less.

[0201] In example embodiments, the electron transport region of the organic light-emitting device may include at least one selected from phosphine oxide compounds and benzimidazole compounds, and may also include alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or combinations thereof.

[0202] The term "organic layer" used herein refers to a single layer and / or a plurality of layers disposed between a first electrode and a second electrode of an organic light emitting device. The material included in the "organic layer" is not limited to an organic material.

[0203] [ Figure 1 Description]

[0204] Figure 1 1 is a schematic diagram of an organic light emitting device 10 according to an example embodiment. The organic light emitting device 10 includes a first electrode 110 , an organic layer 150 , and a second electrode 190 .

[0205] In the following, we will combine Figure 1 A structure of an organic light emitting device 10 and a method of manufacturing the organic light emitting device 10 according to example embodiments will be described.

[0206] [First electrode 110]

[0207] exist Figure 1 In the embodiment, a substrate may be additionally disposed under the first electrode 110 or over the second electrode 190. The substrate may be a glass substrate or a plastic substrate, both of which have excellent mechanical strength, thermal stability, transparency, surface flatness, ease of handling, and waterproofness.

[0208] The first electrode 110 may be formed by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for the first electrode 110 may be selected from materials having a high work function to facilitate hole injection.

[0209] 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 be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and combinations thereof. In example embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, a material for forming the first electrode 110 may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and combinations thereof.

[0210] The first electrode 110 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 110 may have a triple-layer structure of ITO / Ag / ITO.

[0211] [Organic layer 150]

[0212] The organic layer 150 is disposed on the first electrode 110. The organic layer 150 may include an emission layer.

[0213] The organic layer 150 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 190 .

[0214] [Hole Transport Region in Organic Layer 150]

[0215] The hole transport region may have: i) a single layer structure including a single layer including a single material; ii) a single layer structure including a single layer including a plurality of different materials; or iii) a multilayer structure having a plurality of layers including a plurality of different materials.

[0216] The hole transport region may include at least one layer selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer.

[0217] For example, the hole transport region may have: a single-layer structure including a single layer comprising a plurality of different materials; or a multi-layer structure having a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure or a hole injection layer / hole transport layer / emission assisting layer structure, wherein, for each structure, the constituent layers are stacked sequentially from the first electrode 110 in the order stated.

[0218] The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201, and a compound represented by Formula 202:

[0219]

[0220]

[0221] <Formula 201>

[0222]

[0223] <Formula 202>

[0224]

[0225] In equation 201 and equation 202,

[0226] L 201 To L 204 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0227] L 205 Can be selected from *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C 1 -C 20 Alkylene, substituted or unsubstituted C 2 -C20 Alkenylene, substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0228] xa1 to xa4 may each independently be an integer from 0 to 3,

[0229] xa5 can be an integer from 1 to 10, and

[0230] R 201 To R 204 and Q 201 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0231] For example, in Equation 202, R 201 and R 202 The connection may be via a single bond, dimethyl-methylene or diphenyl-methylene, R 203 and R 204 The attachment may be via a single bond, a dimethyl-methylene group or a diphenyl-methylene group.

[0232] In an example embodiment, in equation 201 and equation 202,

[0233] L 201 To L 205 Can be independently selected from:

[0234] Phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, tetraphenylene, perylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, rubidinylene, camphenylene, ovaphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene, and pyridinylene; and

[0235] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 Alkyl phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ) is at least one selected from phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalene, indacenylene, acenaphthenylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, tetraphenylene, perylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, rubidinylene, camphenylene, ovaphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene and pyridylene, and

[0236] Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0237] In example embodiments, xa1 to xa4 may each independently be 0, 1, or 2.

[0238] In example embodiments, xa5 may be 1, 2, 3, or 4.

[0239] In an exemplary embodiment, R 201 To R 204 and Q 201 Can be independently selected from:

[0240] Phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, and pyridyl; and

[0241] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 Alkyl phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ) is at least one selected from phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl and pyridyl, and

[0242] Q 31 To Q 33 Same as described above.

[0243] In an exemplary embodiment, in equation 201, from R 201 To R 203 At least one of the selected ones can be independently selected from:

[0244] fluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; and

[0245] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 Phenyl group of the alkyl group, phenyl group substituted with -F, naphthyl group, fluorenyl group, spirobifluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group; at least one selected from fluorenyl group, spirobifluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group.

[0246] In an exemplary embodiment, in Formula 202, i) R 201 and R 202can be connected via a single bond, and / or ii) R 203 and R 204 Can connect via one-touch.

[0247] In an exemplary embodiment, in equation 202, from R 201 To R 204 At least one of the selected ones may be selected from:

[0248] carbazolyl; and

[0249] The substitution is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 The alkyl group is a phenyl group, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a carbazolyl group selected from at least one group.

[0250] The compound represented by Formula 201 can be represented by Formula 201A:

[0251] <Formula 201A>

[0252]

[0253] For example, the compound represented by Formula 201 can be represented by Formula 201A(1):

[0254] <Formula 201A(1)>

[0255]

[0256] In example embodiments, the compound represented by Formula 201 may be represented by Formula 201A-1:

[0257] <Formula 201A-1>

[0258]

[0259] In example embodiments, the compound represented by Formula 202 may be represented by Formula 202A:

[0260] <Formula 202A>

[0261]

[0262] In example embodiments, the compound represented by Formula 202 may be represented by Formula 202A-1:

[0263] <Formula 202A-1>

[0264]

[0265] In Formula 201A, Formula 201A(1), Formula 201A-1, Formula 202A, and Formula 202A-1,

[0266] L 201 To L 203 , xa1 to xa3, xa5 and R 202 To R 204 Same as described above,

[0267] R 211 and R 212 can be independently related to R 203 The definition is the same.

[0268] R 213 To R 217 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 Alkyl phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl and pyridyl.

[0269] The hole transport region may include at least one compound selected from Compound HT1 to Compound HT39:

[0270]

[0271]

[0272]

[0273] The thickness of the hole transport region can be approximately To about In the range of, for example, about To about When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be in the range of about To about In the range of, for example, about To about In the range of To about In the range of, for example, about To about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics may be obtained without significantly increasing the driving voltage.

[0274] The emission auxiliary layer can improve light emitting 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 the flow of electrons from the electron transport region. The emission auxiliary layer and the electron blocking layer can include materials as described above.

[0275] [p dopant]

[0276] In addition to these materials, the hole transport region may also include a charge generating material for improving the conductive property. The charge generating material may be dispersed uniformly or non-uniformly in the hole transport region.

[0277] The charge generating material may be, for example, a p-dopant.

[0278] In example embodiments, the p-dopant may have a LUMO energy level of about −3.5 eV or less.

[0279] The P dopant may include at least one selected from quinone derivatives, metal oxides, and cyano-containing compounds.

[0280] For example, the p-dopant may include at least one selected from the following compounds:

[0281] Quinone derivatives, such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);

[0282] Metal oxides, such as tungsten oxide or molybdenum oxide;

[0283] 1,4,5,8,9,12-Hexaazatriphenylene-hexanitrile (HAT-CN); and

[0284] The compound represented by formula 221:

[0285]

[0286] <Formula 221>

[0287]

[0288] In formula 221,

[0289] R 221 To R 223 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein R 221 To R 223 At least one selected from the group consisting of cyano, -F, -Cl, -Br, -I, C substituted with -F 1 -C 20 Alkyl, C substituted with -Cl 1 -C 20 Alkyl, C substituted with -Br 1 -C 20 Alkyl and C substituted with -I 1 -C 20 At least one substituent selected from the group consisting of:

[0290] [Emission Layer in Organic Layer 150]

[0291] When the organic light emitting device 10 is a full-color organic light emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, or a blue emission layer according to the sub-pixel. In an example embodiment, the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, wherein the two or more layers are in contact with each other or separated from each other. In an example embodiment, the emission layer may include two or more materials selected from a red light emitting material, a green light emitting material, and a blue light emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light.

[0292] The emission layer may include a thermally delayed fluorescent emitter, and the thermally delayed fluorescent emitter may include a heterocyclic compound.

[0293] The emission layer may include a host and a dopant. The dopant may include a thermally delayed fluorescent dopant, and the thermally delayed fluorescent dopant may include a heterocyclic compound.

[0294] In the emission layer, the amount of the dopant 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.

[0295] The thickness of the emitter layer can be approximately To about In the range of, for example, about To about When the thickness of the emission layer is within this range, excellent light emitting characteristics can be obtained without significantly increasing the driving voltage.

[0296] [Subject in the emission layer]

[0297] In an example embodiment, the host may include a compound represented by Formula 301:

[0298] <Formula 301>

[0299] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21

[0300] In formula 301,

[0301] Ar 301 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,

[0302] xb11 can be 1, 2 or 3,

[0303] L 301 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0304] xb1 can be an integer from 0 to 5.

[0305] R 301 It can be selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 301 )(Q 302 )(Q 303)、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O) 2 (Q 301 ) and -P(=O)(Q 301 )(Q 302 ),

[0306] xb21 can be an integer from 1 to 5, and

[0307] Q 301 To Q 303 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0308] In an exemplary embodiment, Ar in Formula 301 301 Can be selected from:

[0309] naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, peryl, perylenyl, pentaphenyl, indenoanthryl, dibenzofuranyl, and dibenzothiophenyl; and

[0310] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one of naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, peryl, peryl, pentaphenyl, indenoanthryl, dibenzofuranyl and dibenzothiophenyl, and

[0311] Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0312] In Formula 301, when xb11 is two or more, two or more Ar 301 Can connect via one-touch.

[0313] In example embodiments, the compound represented by Formula 301 may be represented by Formula 301-1 or Formula 301-2:

[0314] <Formula 301-1>

[0315]

[0316] <Formula 301-2>

[0317]

[0318] In Formula 301-1 and Formula 301-2,

[0319] A 301 To A 304 can be independently selected from benzene, naphthalene, phenanthrene, fluoranthene, benzo[9,10]phenanthrene, pyrene, pyridine, pyrimidine, indene, fluorene, spirobifluorene, benzofluorene, dibenzofluorene, indole, carbazole, benzocarbazole, dibenzocarbazole, furan, benzofuran, dibenzofuran, naphthofuran, benzonaphthofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthiophene, benzonaphthothiophene and dinaphthothiophene,

[0320] X 301 Can be O, S or N-[(L 304 ) xb4 -R 304 ],

[0321] R 311 To R 314 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),

[0322] xb22 and xb23 can each independently be 0, 1 or 2,

[0323] L 301 、xb1、R 301 and Q 31 To Q 33 Same as described above,

[0324] L 302 To L 304 can be independently 301 The same definition,

[0325] xb2 to xb4 may each independently be defined identically to xb1, and

[0326] R 302 To R 304 can be independently related to R 301 The definition is the same.

[0327] For example, in Formula 301, Formula 301-1, and Formula 301-2, L 301 To L 304 Can be independently selected from:

[0328] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene, and azacarbazolylene; and

[0329] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridyl azine, pyrimidinyl, pyridazinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32) is one of phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene, yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene and azacarbazolylene, and

[0330] Q 31 To Q 33 Same as described above.

[0331] In an example embodiment, in equation 301, equation 301-1, and equation 301-2, R 301 To R 304 Can be independently selected from:

[0332] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0333] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridyl azine, pyrimidinyl, pyridazinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl, and

[0334] Q 31 To Q 33 Same as described above.

[0335] In example embodiments, the host may include an alkaline earth metal complex. For example, the host may be selected from a Be complex (eg, compound H55), a Mg complex, and a Zn complex.

[0336] The host may include at least one selected from 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-tri(carbazolyl-9-yl)benzene (TCP), and compounds H1 to H55:

[0337]

[0338]

[0339]

[0340] [Phosphorescent Dopant in Emission Layer Included in Organic Layer 150]

[0341] The emission layer may also include a phosphorescent dopant. The phosphorescent dopant may include an organic metal complex represented by Formula 401:

[0342] <Formula 401>

[0343] M(L 401 ) xc1 (L 402 ) xc2

[0344] <Formula 402>

[0345]

[0346] In equations 401 and 402,

[0347] M may be selected from iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh) and thulium (Tm),

[0348] L 401 can be selected from the ligand represented by formula 402, xc1 can be 1, 2 or 3, wherein when xc1 is two or more, two or more L 401 can be the same or different from each other,

[0349] L 402It can be an organic ligand, and xc2 can be an integer from 0 to 4, wherein when xc2 is two or more, two or more L 402 can be the same or different from each other,

[0350] X 401 To X 404 may each independently be nitrogen or carbon,

[0351] X 401 and X 403 Can be connected via single or double bonds, X 402 and X 404 Can be connected via single or double bonds,

[0352] A 401 and A 402 can be independently selected from C 5 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,

[0353] X 405 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*'、*-C(Q 411 )(Q 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*'or*=C=*', where Q 411 and Q 412 It can be hydrogen, deuterium, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl or naphthyl,

[0354] X 406 Can be a single bond, O or S,

[0355] R 401 and R 402 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 20 Alkyl, substituted or unsubstituted C 1 -C 20 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) and -P(=O)(Q 401 )(Q 402 ), where Q 401 To Q 403 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, C 6 -C 20 Aryl and C 1 -C 20 Heteroaryl,

[0356] xc11 and xc12 may each independently be an integer from 0 to 10, and

[0357] The * and *' in formula 402 both represent the binding site with M in formula 401.

[0358] In an exemplary embodiment, A in equation 402 401 and A 402They can all be independently selected from phenyl, naphthyl, fluorenyl, spirobifluorenyl, indenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiophenyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl and dibenzothiophenyl.

[0359] In an exemplary embodiment, in equation 402, i)X 401 Can be nitrogen, X 402 It can be carbon, or ii) X 401 and X 402 They may both be nitrogen.

[0360] In an exemplary embodiment, R in equation 402 401 and R 402 Can be independently selected from:

[0361] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0362] The C groups are substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, phenyl, naphthyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl and norbornenyl. 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0363] Cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl;

[0364] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20at least one selected from the group consisting of an alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

[0365] -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) and -P(=O)(Q 401 )(Q 402 ),and

[0366] Q 401 To Q 403 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl and naphthyl.

[0367] In an exemplary embodiment, when xc1 in equation 401 is two or greater, two or more L 401 Two A's 401 It can be connected via X 407 Connect, or two or more L 401 Two A's 402 It can be connected via X 408 Connection (see Compound PD1 to Compound PD4 and Compound PD7). 407 and X 408 can be independently a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 413 )-*'、*-C(Q 413 )(Q 414 )-*' or *-C(Q 413 )=C(Q 414 )-*'(where Q 413 and Q414 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl or naphthyl).

[0368] L in Formula 401 402 It can be a monovalent organic ligand, a divalent organic ligand or a trivalent organic ligand. 402 It may be selected from halogen, diketone (eg, acetylacetone), carboxylic acid (eg, picolinic acid), -C(=O)-, isonitrile, -CN and phosphorus (eg, phosphine or phosphite).

[0369] In example embodiments, the phosphorescent dopant may be selected from, for example, Compound PD1 to Compound PD25:

[0370]

[0371]

[0372] [Fluorescent dopants in the emission layer]

[0373] The fluorescent dopant may include a compound represented by Formula 501.

[0374] The fluorescent dopant may include an arylamine compound or a styrylamine compound.

[0375] In example embodiments, the fluorescent dopant may include a compound represented by Formula 501 below.

[0376] <Formula 501>

[0377]

[0378] In formula 501,

[0379] Ar 501 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,

[0380] L 501 To L 503 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0381] xd1 to xd3 may each independently be an integer from 0 to 3,

[0382] R 501 and R 502 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and

[0383] xd4 can be an integer from 1 to 6.

[0384] In an exemplary embodiment, Ar in Formula 501 501 Can be selected from:

[0385] naphthyl, heptathenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, phenanthrenyl, perylenyl, pentaphenanthrenyl, indenoanthryl, and indenophenanthrenyl; and

[0386] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20at least one selected from the group consisting of alkoxy, phenyl, biphenyl, terphenyl and naphthyl, naphthyl, heptalenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, The following examples include 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33,

[0387] In an exemplary embodiment, L in equation 501 501 To L 503 Can be independently selected from:

[0388] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, ...

[0389] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, a phenylene group, a naphthylene group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracene group, an anthracene group, an fluoranthenyl group, a benzo[9,10]phenanthrenyl group, a pyrenyl group, a fluorenyl group, a phenanthrenyl group, a phenanthrenyl group, a fluoranthrenyl group, a benzo[9,10]phenanthrenyl group, a py ... The compounds include phenylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothiophenylene, and pyridylene.

[0390] In an exemplary embodiment, R in equation 501 501 and R 502 Can be independently selected from:

[0391] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, and pyridyl; and

[0392] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl and -Si(Q 31 )(Q 32 )(Q 33 ) is at least one selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophene, and pyridyl, and

[0393] Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0394] In an example embodiment, xd4 in equation 501 may be 2.

[0395] For example, the fluorescent dopant may be selected from Compound FD1 to Compound FD22:

[0396]

[0397]

[0398]

[0399] In example embodiments, the fluorescent dopant may be selected from the following compounds:

[0400]

[0401]

[0402] [Electron Transport Region in Organic Layer 150]

[0403] The electron transport region may have: i) a single layer structure including a single layer including a single material; ii) a single layer structure including a single layer including a plurality of different materials; or iii) a multilayer structure having a plurality of layers including a plurality of different materials.

[0404] The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer.

[0405] For example, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein, for each structure, the constituent layers are stacked sequentially from the emission layer in the order stated.

[0406] 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 containing at least one π electron-depleted nitrogen-containing ring.

[0407] The term "π-electron-poor nitrogen-containing ring" refers to a C- 1 -C 60 Heterocyclic group.

[0408] For example, the "π-electron-poor nitrogen-containing ring" may be: i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' portion; ii) a heteropolycyclic group in which two or more 5- to 7-membered heteromonocyclic groups each having at least one *-N=*' portion are condensed with each other; or iii) a heteropolycyclic group in which at least one of the 5- to 7-membered heteromonocyclic groups each having at least one *-N=*' portion is condensed with at least one C 5 -C 60 A carbocyclic condensed heteropolycyclic group.

[0409] Examples of π-electron-poor nitrogen-containing rings include imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole, isobenzothiazole, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole.

[0410] For example, the electron transport region may include a compound represented by Formula 601:

[0411] <Formula 601>

[0412] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21

[0413] In formula 601,

[0414] Ar 601 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,

[0415] xe11 can be 1, 2 or 3,

[0416] L 601 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic,

[0417] xe1 can be an integer from 0 to 5,

[0418] R 601 Can be selected from substituted or unsubstituted C 3 -C 10Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),

[0419] Q 601 To Q 603 can be independently C 1 -C 10 Alkyl, C 1 -C 10 alkoxy, phenyl, biphenyl, terphenyl or naphthyl, and

[0420] xe21 can be an integer from 1 to 5.

[0421] In the example embodiment, xe11 number of Ar 601 and xe21 number of R 601 At least one of the may include a π-electron-poor nitrogen-containing ring.

[0422] In an exemplary embodiment, Ar in Formula 601 601 Can be selected from:

[0423] Phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, phenanthrenyl, phenanthrenyl, phenanthrenyl, phenanthryl, phenanthroline, phenazinyl, phenanthryl ...

[0424] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one selected from phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, naphthyl, phenanthrenyl, peryl, pentaphenanthrenyl, indenoanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl, and

[0425] Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0426] When xe11 in Formula 601 is two or greater, two or more Ar 601 Can connect via one-touch.

[0427] In an exemplary embodiment, Ar in Formula 601 601 It may be anthracene.

[0428] In example embodiments, the compound represented by Formula 601 may be represented by Formula 601-1:

[0429] <Formula 601-1>

[0430]

[0431] In formula 601-1,

[0432] 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 ), where, from X 614 To X 616 At least one of the selected ones may be N,

[0433] L 611 To L 613 can be independently 601 The same definition,

[0434] xe611 to xe613 can all be independently defined the same as xe1,

[0435] R 611 To R 613 can be independently related to R 601 are defined identically, and

[0436] R 614 To R 616 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0437] In an exemplary embodiment, L in equation 601 601 and L in formula 601-1 611 To L 613 Can be independently selected from:

[0438] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene, and azacarbazolylene; and

[0439] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazine at least one selected from the group consisting of phenylene, naphthylene, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthrylenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene , pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene and azacarbazolylene.

[0440] In example embodiments, xe1 in Formula 601 and xe611 to xe613 in Formula 601-1 may each independently be 0, 1, or 2.

[0441] In an exemplary embodiment, R in equation 601 601 and R in formula 601-1 611 To R 613 Can be independently selected from:

[0442] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl , pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl;

[0443] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalide a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a benzo[9,10]phenanthrenyl group, a pyrenyl group, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0444] -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),and

[0445] Q 601 and Q 602 Same as described above.

[0446] The electron transport region may include at least one compound selected from Compound ET1 to Compound ET36:

[0447]

[0448]

[0449]

[0450]

[0451] In example embodiments, the electron transport region may include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq 3 At least one compound selected from the group consisting of 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ) and NTAZ.

[0452]

[0453] The thickness of the buffer layer, hole blocking layer or electron control layer can be about To about In the range of, for example, about To about When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within these ranges, the electron transport region may have excellent hole blocking characteristics or electron control characteristics without significantly increasing the driving voltage.

[0454] The thickness of the electron transport layer can be about To about In the range of, for example, about To about When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without significantly increasing the driving voltage.

[0455] 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.

[0456] The metal-containing material may include at least one selected from an alkali metal complex and an alkaline earth metal complex. The alkali metal complex may include a metal ion selected from Li ion, Na ion, K ion, Rb ion and Cs ion, and the alkaline earth metal complex may include a metal ion selected from Be ion, Mg ion, Ca ion, Sr ion and Ba ion. The ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene.

[0457] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium hydroxyquinolate, LiQ) or compound ET-D2.

[0458]

[0459] The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.

[0460] The electron injection layer may have: i) a single-layer structure including a single layer containing a single material; ii) a single-layer structure including a single layer containing a plurality of different materials; or iii) a multi-layer structure having a plurality of layers including a plurality of different materials.

[0461] 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 a combination thereof.

[0462] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In an exemplary embodiment, the alkali metal may be Li, Na, or Cs. In an exemplary embodiment, the alkali metal may be Li or Cs.

[0463] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

[0464] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

[0465] The alkali metal compounds, alkaline earth metal compounds, and rare earth metal compounds may be selected from oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of alkali metals, alkaline earth metals, and rare earth metals.

[0466] The alkali metal compound may be selected from alkali metal oxides such as Li 2 O, Cs 2 O, or K 2 O and alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI. In an exemplary embodiment, the alkali metal compound may be selected from LiF, Li 2 O, NaF, LiI, NaI, CsI, and KI.

[0467] The alkaline earth metal compound may be selected from alkaline earth metal oxides such as BaO, SrO, CaO, Ba x Sr 1-x O (0 < x < 1), or Ba x Ca 1-xAlkaline earth metal oxides of O(0 < x < 1). In an exemplary embodiment, the alkaline earth metal compound may be selected from BaO, SrO, and CaO.

[0468] The rare earth metal compound may be selected from YbF 3 , ScF 3 , Sc 2 O 3 , Y 2 O 3 , Ce 2 O 3 , GdF 3 and TbF 3 . In an exemplary embodiment, the rare earth metal compound may be selected from YbF 3 , ScF 3 , TbF 3 , YbI 3 , ScI 3 and TbI 3 .

[0469] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex may include ions of the alkali metal, alkaline earth metal, and rare earth metal as described above, and the ligand coordinated to the metal ion of the alkali metal complex, alkaline earth metal complex, or rare earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, and cyclopentadiene.

[0470] The electron injection layer may include the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or a combination thereof as described above, or may be composed of the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or a combination thereof as described above. In an exemplary embodiment, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or a combination thereof may be uniformly or non-uniformly dispersed in the matrix including the organic material.

[0471] The thickness of the electron injection layer may be in the range of about to about , for example, in the range of about to about When the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory electron injection characteristics without significantly increasing the driving voltage.

[0472] [Second electrode 190]

[0473] The second electrode 190 may be disposed on the organic layer 150 having such a structure. The second electrode 190 may be a cathode as an electron injection electrode, and in this regard, a material for forming the second electrode 190 may be selected from metals, alloys, conductive compounds, and combinations thereof having a relatively low work function.

[0474] The second electrode 190 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, and IZO. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0475] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.

[0476] [ Figures 2 to 4 Description]

[0477] Figure 2 The organic light emitting device 20 includes a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190 which are sequentially stacked in the order stated, Figure 3 The organic light emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second cover layer 220 sequentially stacked in the order of this statement, Figure 4 The organic light emitting device 40 includes a first cover layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second cover layer 220 which are sequentially stacked in the stated order.

[0478] about Figures 2 to 4 , can be combined by reference Figure 1 The description is given to understand the first electrode 110 , the organic layer 150 , and the second electrode 190 .

[0479] In the organic layer 150 of each of the organic light-emitting devices 20 and the organic light-emitting devices 40, light generated in the emission layer can pass through the first electrode 110 (which is a semi-transmissive electrode or a transmissive electrode) and the first cover layer 210 toward the outside, and in the organic layer 150 of each of the organic light-emitting devices 30 and the organic light-emitting devices 40, light generated in the emission layer can pass through the second electrode 190 (which is a semi-transmissive electrode or a transmissive electrode) and the second cover layer 220 toward the outside.

[0480] The first capping layer 210 and the second capping layer 220 may improve external light emitting efficiency according to the principle of constructive interference.

[0481] The first capping layer 210 and the second capping layer 220 may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material.

[0482] At least one selected from the first capping layer 210 and the second capping layer 220 may each independently include at least one material selected from carbocyclic compounds, heterocyclic compounds, amine compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds, and amine compounds may be selectively substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In example embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include an amine compound.

[0483] In example embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include the compound represented by Formula 201 or the compound represented by Formula 202.

[0484] In example embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include a compound selected from Compound HT28 to Compound HT33 and Compound CP1 to Compound CP5:

[0485]

[0486] A layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region can be formed in a specific region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser induced thermal imaging.

[0487] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition temperature may be about 100° C. to about 500° C., about 10 -8 Up to about 10 -3 Torr vacuum and approx. / second to approximately The vacuum deposition was performed at a deposition rate of 2000 Å / s.

[0488] When a layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region are formed by spin coating, spin coating can be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80°C to about 200°C by taking into account the materials to be included in the layer to be formed and the structure of the layer to be formed.

[0489] [General Definition of Substituents]

[0490] As used herein, the term "C 1 -C 60 "Alkyl" refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, examples of which include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl. As used herein, the term "C 1 -C 60 "Alkylene" refers to C 1 -C 60 An alkyl group is a divalent group having the same structure.

[0491] As used herein, the term "C 2 -C 60 "Alkenyl" refers to 2 -C 60 The term "C" as used herein refers to a hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminal of the alkyl group, examples of which include ethenyl, propenyl, and butenyl. 2 -C 60 "Alkenylene" refers to C 2 -C 60 An alkenyl group is a divalent group having the same structure.

[0492] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a C 2 -C 60 A hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminal of an alkyl group, examples of which include ethynyl and propynyl. As used herein, the term “C 2 -C 60 "Alkynylidene" refers to a C 2 -C 60 Alkynyl is a divalent group having the same structure.

[0493] As used herein, the term "C 1 -C 60 "Alkoxy" refers to -OA 101 (Among them, A 101 C 1 -C 60 An alkyl group is a monovalent group represented by an alkyl group, examples of which include a methoxy group, an ethoxy group and an isopropoxy group.

[0494] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, examples of which include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, examples of which include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. 3 -C 10 "Cycloalkylene" refers to 3 -C 10 The cycloalkyl group is a divalent group having the same structure.

[0495] As used herein, the term "C 1 -C 10 The term "heterocycloalkyl" as used herein refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, Si, P and S as ring atoms and 1 to 10 carbon atoms, and examples thereof include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and tetrahydrothienyl. 1 -C 10 "Heterocycloalkylene" refers to a C 1 -C 10 The heterocycloalkyl group has a divalent group of the same structure.

[0496] As used herein, the term "C 3 -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, examples of which include cyclopentenyl, cyclohexenyl and cycloheptenyl. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to 3 -C 10 The cycloalkenyl group is a divalent group having the same structure.

[0497] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl group" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as ring atoms, 1 to 10 carbon atoms and at least one double bond in its ring. 1 -C 10 Non-limiting examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. As used herein, the term “C 1 -C 10 "Heterocycloalkenylene" refers to a C 1 -C 10 The heterocycloalkenyl group is a divalent group having the same structure.

[0498] As used herein, the term "C6 -C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms. 6 -C 60 The arylene group refers to a divalent group having a carbocyclic aromatic system including 6 to 60 carbon atoms. 6 -C 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and When C 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the rings may be fused to each other.

[0499] As used herein, the term "C 1 -C 60 The term "heteroaryl" as used herein refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom in addition to 1 to 60 carbon atoms. 1 -C 60 The term "heteroarylene group" refers to a divalent group having a heterocyclic aromatic system having at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom in addition to 1 to 60 carbon atoms. 1 -C 60 Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene group includes two or more rings, the rings may be condensed with each other.

[0500] As used herein, the term "C 6 -C 60 "Aryloxy" refers to -OA 102 (Among them, A 102 C 6 -C 60 Aryl), the term "C 6 -C 60 "Arylthio" refers to -SA 103 (Among them, A 103 C 6 -C 60 aryl).

[0501] As used herein, the term "C 1 -C 60 "Heteroaryloxy" refers to -OA104 (Among them, A 104 C 1 -C 60 Heteroaryl), the term "C 1 -C 60 "Heteroarylthio" refers to -SA 105 (Among them, A 105 C 1 -C 60 heteroaryl).

[0502] The term "monovalent non-aromatic condensed polycyclic group" as used herein refers to a monovalent group having two or more rings condensed with each other, having only carbon atoms (e.g., having 8 to 60 carbon atoms) as ring atoms, and containing at least one non-aromatic ring. A specific example of a monovalent non-aromatic condensed polycyclic group is a fluorenyl group. The term "divalent non-aromatic condensed polycyclic group" as used herein refers to a divalent group having the same structure as a monovalent non-aromatic condensed polycyclic group.

[0503] The term "monovalent non-aromatic condensed heteropolycyclic group" as used herein refers to a monovalent group having two or more rings condensed with each other, having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom other than carbon atoms (e.g., having 1 to 60 carbon atoms), and containing at least one non-aromatic ring. An example of a monovalent non-aromatic condensed heteropolycyclic group is a carbazolyl group. The term "divalent non-aromatic condensed heteropolycyclic group" as used herein refers to a divalent group having the same structure as a monovalent non-aromatic condensed heteropolycyclic group.

[0504] As used herein, the term "C 5 -C 60 "Carbocyclic group" refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms, wherein the ring atoms are only carbon atoms. 5 -C 60 The carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. 5 -C 60 The carbocyclic group can be a ring (such as benzene), a monovalent group (such as phenyl), or a divalent group (such as phenylene). 5 -C 60 The number of substituents of the carbocyclic group, C 5 -C 60 The carbocyclic group may be a trivalent group or a tetravalent group.

[0505] As used herein, the term "C 1 -C 60 The term "heterocyclic group" refers to a group consisting of at least one heteroatom selected from N, O, Si, P and S other than carbon (the number of carbon atoms may be in the range of 1 to 60) as a ring-forming atom.5 -C 60 The carbocyclic group has a group of the same structure.

[0506] In this specification, substituted C 5 -C 60 Carbocyclic, substituted C 7 -C 60 Carbocyclic, substituted C 1 -C 60 Heterocyclic, substituted C 1 -C 20 Alkylene, substituted C 2 -C 20 Alkenylene, substituted C 3 -C 10 Cycloalkylene, substituted C 1 -C 10 Heterocycloalkylene, substituted C 3 -C 10 Cycloalkenylene, substituted C 1 -C 10 Heterocycloalkenylene, substituted C 6 -C 60 Arylene, substituted C 1 -C 60 Heteroarylene, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C60 At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:

[0507] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;

[0508] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) selected from at least one of C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;

[0509] C 3 -C10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups;

[0510] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 ) selected from at least one of C 3 -C10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and

[0511] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),and

[0512] Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups and terphenyl groups.

[0513] The term "Ph" as used herein refers to phenyl, the term "Me" as used herein refers to methyl, the term "Et" as used herein refers to ethyl, the term "ter-Bu" or "Bu" as used herein refers to ethyl. t ” means tert-butyl, and the term “OMe” as used herein means methoxy.

[0514] As used herein, the term "biphenyl" refers to a "phenyl group substituted with a phenyl group". 6 -C 60 "substituted phenyl" having "aryl" as a substituent.

[0515] As used herein, the term "terphenyl" refers to a "phenyl group substituted with a biphenyl group". 6 -C 60 Aryl C 6 -C 60 "phenyl" having "aryl" as a substituent.

[0516] Unless otherwise defined, * and *' as used herein refer to the binding sites to adjacent atoms in the corresponding formula.

[0517] The following examples and comparative examples are provided to highlight the features of one or more embodiments, but it will be understood that the examples and comparative examples are not to be construed as limiting the scope of the embodiments, and the comparative examples are not to be construed as being outside the scope of the embodiments. In addition, it will be understood that the embodiments are not limited to the specific details described in the examples and comparative examples.

[0518] The expression "B is used instead of A" used in describing a synthesis example means that the same number of molar equivalents of B is used instead of the same number of molar equivalents of A.

[0519] [Example]

[0520] [Synthesis example]

[0521] Synthesis Example 1: Synthesis of Compound 5

[0522] (1) Synthesis of intermediate 5(1)

[0523]

[0524] 10 g (1.0 eq, 47 mmol) of 2-(phenylamino)benzoic acid was added to a reaction vessel, vacuum dried, and filled with nitrogen. 60 mL of methanol was added thereto, and refluxed at 60° C. 6.1 mL (2.0 eq, 94 mmol) of SOCl was slowly added dropwise thereto. 2 , while maintaining the temperature at 60° C. The reaction mixture was stirred under reflux at 60° C. for 12 hours. The reaction vessel was cooled to room temperature, and saturated NaHCO 3 The solution was added to terminate the reaction. After the reaction was terminated, an organic layer was extracted therefrom using ethyl acetate (EA) and distilled water. The extracted organic layer was dried using anhydrous sodium sulfate, filtered through diatomaceous earth, and the solvent was evaporated therefrom. Then, column chromatography was performed thereon to obtain 8.5 g (yield 80%) of intermediate 5 (1) (i.e., methyl 2-(phenylamino)benzoate).

[0525] 1 H NMR (500 MHz, CDCl 3 )δ9.52(s,1H),7.91(d,J=8.0Hz,1H),7.26(t,J=7.8Hz,2H),7.23-7.19(m ,3H),7.18(s,1H),7.01(t,J=7.3Hz,1H),6.70-6.58(m,1H),3.78(s,3H).

[0526] (2) Synthesis of intermediate 5(2)

[0527]

[0528] 8.5g (1.0eq, 37mmol) of 2- (phenylamino) benzoic acid methyl ester was added to a reaction vessel (flask), and vacuum dried, and the reaction vessel was filled with nitrogen. 400mL of tetrahydrofuran (THF) was added thereto, and 50mL (4.0eq, 150mmol) of 3.0M methylmagnesium bromide was slowly added thereto, and stirred for 3 hours. The reaction was terminated by using an aqueous ammonium chloride solution, and an organic layer was extracted therefrom using distilled water and ethyl acetate, and then dried. The dried reaction mixture was added to a reaction vessel, and sulfuric acid was added thereto and stirred at room temperature for 30 minutes. After the reaction was completed, the reaction product was neutralized by using an aqueous sodium hydroxide solution, and an organic layer was extracted therefrom using distilled water and ethyl acetate. The extracted organic layer was dried using anhydrous sodium sulfate, filtered by diatomaceous earth, and the solvent was evaporated therefrom. Then, column chromatography was performed to obtain 4.9g (yield of 63%) of intermediate 5 (2) (i.e. 9,10-dihydro-9,9-dimethylacridine).

[0529] 1 H NMR (500 MHz, CDCl 3 )δ7.38(d,J=7.7Hz,2H),7.10(t,J=7.2Hz,2H),6.92(d,J=6.8Hz,2H),6.69(d,J=7.5Hz,2H),6.13(s,1H),1.58(s,6H).

[0530] (3) Synthesis of intermediate 5(3)

[0531]

[0532] 10g (1.0eq, 63mmol) of 2-chloro-3-nitropyridine is added to a reaction vessel, and vacuum dried, and the reaction vessel is filled with nitrogen. Then, 5.76mL (1.0eq, 63mmol) of aniline and 100mL of ethylene glycol are added thereto, and stirred at a temperature of 140°C for 8 hours. After the reaction is complete, the reaction vessel is cooled to room temperature, and an organic layer is extracted therefrom by using distilled water and ethyl acetate. Then, the extracted organic layer is dried by using anhydrous sodium sulfate, and filtered by diatomaceous earth, and the solvent is evaporated therefrom. Then, column chromatography is performed to obtain 12g (yield is 87%) of intermediate 5 (3) (i.e. 3-nitro-N-phenylpyridine-2-amine).

[0533] 1 H NMR (500 MHz, CDCl 3 )δ10.12(s,1H),8.53(dd,J=8.3,1.8Hz,1H),8.49(dd,J=4.5,1.8Hz,1H),7.65(dt,J =8.7,1.6Hz,2H),7.42-7.38(m,2H),7.21-7.17(m,1H),6.83(dd,J=8.3,4.5Hz,1H).

[0534] (4) Synthesis of intermediate 5(4)

[0535]

[0536] 12 g (1.0 eq, 55 mmol) of 3-nitro-N-phenylpyridin-2-amine and 37 g (3.0 eq, 160 mmol) of SnCl 2 ·2H 2 O was added to the reaction container, vacuum dried, and filled with nitrogen. 300 mL of methanol was added thereto, and refluxed and stirred at 60° C. for 2 hours. By adding NaHCO 3The reaction mixture was neutralized with an aqueous solution and the reaction was terminated. An organic layer was extracted therefrom using distilled water and ethyl acetate. The extracted organic layer was dried using anhydrous magnesium sulfate and filtered through celite, and the solvent was evaporated therefrom. Then, it was recrystallized using dichloromethane (MC) and hexane to obtain 8.2 g (yield 81%) of intermediate 5 (4) (i.e., N 2 -phenylpyridine-2,3-diamine).

[0537] 1 H NMR (500 MHz, CDCl 3 )δ7.84(dd,J=4.9,1.5Hz,1H),7.31-7.24(m,4H),7.02(dd,J=7.6,1.6Hz,1H),6. 96(tt,J=7.1,1.6Hz,1H), 6.78(dd,J=7.6,4.9Hz,1H), 6.19(s,1H), 3.41(s,2H).

[0538] (5) Synthesis of Intermediate 5(5)

[0539]

[0540] 0.5 g (1.0 eq, 2.7 mmol) of N 2 -phenylpyridine-2,3-diamine and 0.59g (1.0eq, 2.7mmol) of 4-bromobenzoyl chloride were added to the reaction vessel, vacuum dried, and filled with nitrogen. 10mL of THF was added thereto and stirred. Then, the reaction vessel was cooled to a temperature of 0°C. 0.4mL of triethylamine (TEA) was slowly added thereto while maintaining a temperature of 0°C and stirred at room temperature for 4 hours. After the reaction was completed, an organic layer was extracted therefrom using distilled water and ethyl acetate. The extracted organic layer was dried using anhydrous magnesium sulfate, filtered through diatomaceous earth, and the solvent was evaporated therefrom. Then, dichloromethane and hexane were used to perform recrystallization thereon to obtain 0.6g (yield of 61%) of intermediate 5 (5) (i.e. 4-bromo-N-(2-(phenylamino)pyridin-3-yl)benzamide).

[0541] 1 H NMR (500 MHz, CDCl 3)δ8.24(d,J=7.4Hz,1H),8.19(dd,J=4.8,1.6Hz,1H),7.69(s,1H),7.58-7.49(m,2H),7.4 4-7.37(m,2H),7.33-7.27(m,2H),7.11(d,J=7.8Hz,2H),7.07-6.98(m,2H),6.53(s,1H).

[0542] (6) Synthesis of intermediate 5(6)

[0543]

[0544] 0.60g (1.0eq, 1.6mmol) of 4-bromo-N-(2-(phenylamino)pyridin-3-yl)benzamide and 0.10g (0.33eq, 0.54mmol) of p-toluenesulfonic acid were added to a reaction vessel, and vacuum dried, and the reaction vessel was filled with nitrogen. 8mL of xylene was added thereto, and refluxed at a temperature of 140°C for 5 hours. After the reaction was completed, the reaction vessel was cooled to room temperature, and hexane was added thereto to obtain solid crystals. The obtained solid was dissolved in chloroform, and ethanol was used to perform recrystallization thereto to obtain 0.5g (yield of 87.7%) of intermediate 5 (6) (i.e. 2-(4-bromophenyl)-3 phenyl-3H-imidazo[4,5-b]pyridine).

[0545] 1 H NMR (500 MHz, CDCl 3 )δ8.49(dd,J=4.7,1.3Hz,1H),7.83(d,J=8.1Hz,1H),7.62-7.54(m,3H),7.51 (s,3H),7.43(dd,J=8.1,4.8Hz,1H),7.41-7.37(m,2H),7.19(d,J=8.0Hz,1H).

[0546] (7) Synthesis of Compound 5

[0547]

[0548] 0.50 g (1.0 eq, 1.4 mmol) of 2-(4-bromophenyl)-3-phenyl-3H-imidazo[4,5-b]pyridine, 0.33 g (1.1 eq, 1.6 mmol) of 9,10-dihydro-9,9-dimethylacridine, 0.13 g (0.10 eq, 0.14 mmol) of tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3), 0.060g (0.20eq, 0.29mmol) of tri-tert-butylphosphine and 0.52g (4.0eq, 5.7mmol) of sodium tert-butoxide were added to the reaction vessel, vacuum dried, and the reaction vessel was filled with nitrogen. 8.5mL of toluene was added to the reaction vessel, and the compound was dissolved therein, and refluxed and stirred at a temperature of 110°C for 3 hours. After the reaction was completed, the organic layer was extracted therefrom using distilled water and ethyl acetate. The extracted organic layer was dried using anhydrous magnesium sulfate, filtered through diatomaceous earth, and the solvent was evaporated therefrom. After column chromatography, it was recrystallized using dichloromethane and hexane to obtain 0.54g (yield of 79%) of final compound 5 (9,10-dihydro-9,9-dimethyl-10-(4-(3-phenyl-3H-imidazo[4,5-b]pyridine-2-yl)phenyl)acridine).

[0549] 1 H NMR (500 MHz, CDCl 3 )δ8.44(dd,J=4.8,1.4Hz,1H),8.19(dd,J=8.0,1.4Hz,1H),7.91-7.80(m,2H),7.63-7.55(m,2H),7.54-7. 43(m,5H),7.37-7.31(m,3H),6.95(dtd,J=19.7,7.3,1.5Hz,4H),6.26(dd,J=8.0,1.3Hz,2H),1.66(s,6H). APCI-MS(m / z): 479[M+].

[0550] Synthesis Example 2: Synthesis of Compound 7

[0551] (1) Synthesis of intermediate 7(1)

[0552]

[0553] 0.50g (1.0eq, 3.2mmol) of 4-chloro-3-nitropyridine is added to a reaction vessel, and vacuum dried, and the reaction vessel is filled with nitrogen. 10mL of ethylene glycol is added to the reaction vessel, and stirred to dissolve the compound. 0.58ml (2.0eq, 6.3mmol) of aniline is added thereto, and refluxed and stirred at a temperature of 140°C for 8 hours. After the reaction is completed, the reaction product is washed, and an organic layer is extracted therefrom using ethyl acetate. The extracted organic layer is dried using magnesium sulfate, and filtered through diatomaceous earth, and the solvent is evaporated therefrom. Then, column chromatography is performed to obtain 0.57g (yield of 83%) of intermediate 7 (1) (i.e. 3-nitro-N-phenylpyridine-4-amine).

[0554] 1 H NMR: 9.78-9.49(s,1H),9.29(s,1H),8.25(dd,J=6.1,0.5Hz,1H),7.58-7.42( m,2H),7.36(dd,J=10.8,4.2Hz,1H),7.32-7.27(m,2H),6.95(d,J=6.2Hz,1H).

[0555] (2) Synthesis of intermediate 7(2)

[0556]

[0557] 0.57g (1.0eq, 2.6mmol) of 3-nitro-N-phenylpyridine-4-amine was added to a reaction vessel, vacuum dried, and filled with nitrogen. 38mL of ethanol was added to the reaction vessel, stirred to dissolve the compound, and the compound was refluxed and stirred. 1.5g (10eq, 26mmol) of iron was added thereto, and stirred to fully disperse it in the solution. Then, 1.4g (10eq, 26mmol) of ammonium chloride was dissolved in 11mL of distilled water, added to the reaction vessel, and refluxed and stirred for 2 hours. After the reaction was completed, the reaction product was filtered through diatomaceous earth, washed with distilled water, and an organic layer was extracted therefrom using ethyl acetate. The extracted organic layer was dried using magnesium sulfate, filtered through diatomaceous earth, and the solvent was evaporated therefrom. Then, dichloromethane and hexane were used to perform recrystallization on it to obtain 0.39g (yield 80%) of intermediate 7 (2) (i.e., N 4 -phenylpyridine-3,4-diamine).

[0558] 1 H NMR: 8.01 (d, J = 58.6 Hz, 2H), 7.34 (t, J = 7.8 Hz, 2H), 7.17-7.05 (m, 3H), 7.01 (s, 1H), 5.97 (s, 1H), 3.39 (s, 2H).

[0559] (3) Synthesis of intermediate 7(3)

[0560]

[0561] 0.39 g (1.0 eq, 1.8 mmol) of N 4-phenylpyridine-3,4-diamine and 0.40g (1.0eq, 1.8mmol) of 4-bromobenzoyl chloride were added to a reaction vessel, vacuum dried, and filled with nitrogen. 8mL of THF was added to the reaction vessel, and the compound was dissolved therein. Then, 0.3mL of triethylamine was slowly added dropwise thereto, and stirred. After the reaction was completed, the precipitate obtained by washing with distilled water was filtered to obtain 0.54g (yield 82%) of intermediate 7 (3) (i.e. 4-bromo-N-(4-(phenylamino)pyridin-3-yl)benzamide.

[0562] 1 H NMR: 9.34(s,1H),8.75(d,J=6.4Hz,1H),7.94(d,J=8.1Hz,1H),7.88(d,J=7.7Hz,1H),7.69- 7.62(m,2H),7.58-7.49(m,2H),7.51-7.43(m,2H),7.39-7.32(m,2H),7.20(d,J=7.8Hz,2H).

[0563] (4) Synthesis of intermediate 7(4)

[0564]

[0565] 0.50g (1.0eq, 1.4mmol) of 4-bromo-N-(4-(phenylamino)pyridin-3-yl)benzamide was added to a reaction vessel, and vacuum dried, and the reaction vessel was filled with nitrogen. 10mL of acetic acid was added to the reaction vessel to dissolve the compound, and the compound was stirred at reflux at a temperature of 120°C. After the reaction was completed, the reaction product was neutralized by aqueous sodium carbonate solution, washed with distilled water, and an organic layer was extracted therefrom using ethyl acetate. The extracted organic layer was dried using magnesium sulfate, filtered through diatomaceous earth, and the solvent was evaporated therefrom. Then, recrystallization was performed on it using dichloromethane and hexane to obtain 0.28g (yield of 67%) of intermediate 7 (4) (i.e., 2-(4-bromophenyl)-1-phenyl-1H-imidazo[4,5-c]pyridine).

[0566] 1 H NMR: 9.21 (s, 1H), 8.45 (d, J = 4.9 Hz, 1H), 7.63-7.51 (m, 3H), 7.51-7.40 (m, 4H), 7.35-7.27 (m, 2H), 7.20 (d, J = 5.5 Hz, 1H).

[0567] (5) Synthesis of Compound 7

[0568]

[0569] 0.50g (1.0eq, 1.4mmol) of 2- (4-bromophenyl) -1-phenyl -1H- imidazo [4,5-c] pyridine, 0.33g (1.1eq, 1.6mmol) of 9,9- dimethyl -9,10- dihydroacridine, 0.13g (0.10eq, 0.14mmol) of tri (dibenzylideneacetone) dipalladium (0) and 0.52g (4.0eq, 5.7mmol) of sodium tert-butoxide were added to a reaction vessel, and vacuum dried, and the reaction vessel was filled with nitrogen. 9mL of toluene was added to the reaction vessel to dissolve the compound. 0.060g (0.20eq, 0.28mmol) of tri-tert-butylphosphine was added thereto, and refluxed at a temperature of 110°C for 2 hours. After the reaction was completed, the reaction product was washed with distilled water, and the organic layer was extracted therefrom by using ethyl acetate. The extracted organic layer was dried by using magnesium sulfate, filtered through celite, and the solvent was evaporated therefrom. Then, after column chromatography, it was recrystallized using ethyl acetate and hexane to obtain 0.35 g (yield 52%) of the final compound 7 (9,9-dimethyl-10-(4-(1-phenyl-1H-imidazo[4,5-c]pyridin-2-yl)phenyl)-9,10-dihydroacridine).

[0570] 1 H NMR: 9.24(s,1H),8.47(d,J=5.1Hz,1H),7.97-7.71(m,2H),7.67-7.49(m,3H),7.48-7.42(m,2H),7.43-7.37( m,2H),7.35-7.29(m,2H),7.23(t,J=6.7Hz,1H),7.03-6.86(m,4H),6.25(dd,J=8.0,1.4Hz,2H),1.66(s,6H). APCI-MS(m / z): 479[M+].

[0571] Synthesis Example 3: Synthesis of Compound 9

[0572] (1) Synthesis of intermediate 9(1)

[0573]

[0574] 4.5g (1.0eq, 26mmol) of 2-bromopyridine-3-amine and 8.6g (1.5eq, 39mmol) of 4-bromobenzoyl chloride were added to the reaction vessel, and vacuum dried, and the reaction vessel was filled with nitrogen. 72mL of THF was added thereto, stirred, and cooled to a temperature of 0°C. 6.0mL of triethylamine was slowly dripped thereto, while maintaining a temperature of 0°C, and stirred at room temperature for 4 hours. After the reaction was completed, an organic layer was extracted therefrom using distilled water and ethyl acetate. The extracted organic layer was dried using anhydrous magnesium sulfate, filtered through diatomaceous earth, and the solvent was evaporated therefrom. Then, column chromatography was performed on it, and dichloromethane and hexane were used to perform recrystallization on it to obtain 9.2g (yield of 97%) of intermediate 9 (1) (i.e. 4-bromo-N-(2-bromopyridine-3-yl) benzamide).

[0575] 1 H NMR (500 MHz, CDCl 3 )δ8.83(dd,J=8.1,1.8Hz,1H),8.43(s,1H),8.15(dd,J=4.6,1.8Hz,1H),7.82-7.77(m,2H),7.72-7.67(m,2H),7.34(dd,J=8.1,4.6Hz,1H).

[0576] (2) Synthesis of intermediate 9(2)

[0577]

[0578] 9.4g (1eq, 26mmol) of 4-bromo-N-(2-bromopyridine-3-yl) benzamide, 13g (1.5eq, 40mmol) of cesium carbonate, 0.50g (0.10eq, 2.6mmol) of cuprous iodide (I) and 0.96g (0.20eq, 5.3mmol) of 1,10-phenanthroline are added to a reaction vessel, and vacuum dried, and the reaction vessel is filled with nitrogen. 210mL of ethylene glycol dimethyl ether (DME) is added thereto, and refluxed at a temperature of 80°C for 24 hours. After the reaction is complete, an organic layer is extracted therefrom by using distilled water and ethyl acetate. The extracted organic layer is dried by using anhydrous magnesium sulfate, and filtered by diatomaceous earth, and the solvent is evaporated therefrom. Then, column chromatography was performed thereon to obtain 5.2 g (yield 72%) of Intermediate 9(2) (ie, 2-(4-bromophenyl)oxazolo[5,4-b]pyridine).

[0579] 1 H NMR (500 MHz, CDCl 3)δ8.37(dd,J=4.9,1.5Hz,1H),8.20-8.14(m,2H),8.08(dd,J=7.8,1.6Hz,1H),7.73-7.68(m,2H),7.37(dd,J=7.8,4.9Hz,1H).

[0580] (3) Synthesis of Compound 9

[0581]

[0582] 3.0g (1.0eq, 11mmol) of 2- (4- bromophenyl) oxazolo [5,4-b] pyridine, 2.5g (1.1eq, 12mmol) of 9,10- dihydro -9,9- dimethyl acridine, 1.0g (0.050eq, 1.1mmol) of tri (dibenzylideneacetone) dipalladium (0), 0.22g (0.10eq, 1.1mmol) of tri-tert-butylphosphine and 4.0g (4.0eq, 44mmol) of sodium tert-butoxide were added to the reaction vessel, and vacuum dried, and the reaction vessel was filled with nitrogen. 50mL of toluene was added to the reaction vessel to dissolve the compound, and the compound was refluxed at a temperature of 30 ° C for 1 hour. After the reaction is completed, the organic layer is extracted therefrom using distilled water and ethyl acetate. The extracted organic layer is dried using anhydrous magnesium sulfate, filtered through diatomaceous earth, and the solvent is evaporated therefrom. After column chromatography, it was recrystallized using dichloromethane and hexane to obtain 2.7 g (yield 61%) of the final compound 9 (9,10-dihydro-9,9-dimethyl-10-(4-(oxazolo[5,4-b]pyridin-2-yl)phenyl)acridine).

[0583] 1 H NMR (500 MHz, CDCl 3 )δ8.55(d,J=8.5Hz,2H),8.40(dd,J=5.0,1.5Hz,1H),8.12(dd,J=7.8,1.5Hz,1H),7.56(d,J=8.5Hz,2H),7.48(dd,J=7.5,1.6Hz,2H) ,7.40(dd,J=7.8,5.0Hz,1H),6.98(dtd,J=18.2,7.3,1.4Hz,4H),6.34(dt,J=12.9,6.5Hz,2H),1.71(s,6H), APCI-MS(m / z): 403[M+].

[0584] Synthesis Example 4: Synthesis of Compound 11

[0585] (1) Synthesis of intermediate 11(1)

[0586]

[0587] 3.0g (1.0eq, 14mmol) of 9,10-dihydro-9,9-dimethylacridine, 5.3g (1.3eq, 19mmol) of 4-bromoiodobenzene, 0.30g (0.080eq, 1.2mmol) of 18-crown ether-6, 0.47g (0.52eq, 7.5mmol) of copper (powder) and 7.9g (4.0eq, 57mmol) of potassium carbonate were added to the reaction vessel, and vacuum dried, and the reaction vessel was filled with nitrogen. 20mL of 1,2-dichlorobenzene was added to the reaction vessel, and refluxed and stirred at a temperature of 190°C for 2 hours. After the reaction was completed, the organic layer was extracted therefrom using distilled water and ethyl acetate. The extracted organic layer was dried using anhydrous magnesium sulfate, filtered through diatomaceous earth, and the solvent was evaporated therefrom. Then, column chromatography was performed thereon to obtain 3.8 g (yield 72%) of Intermediate 11(1) (ie, 10-(4-bromophenyl)-9,10-dihydro-9,9-dimethylacridine).

[0588] 1 H NMR (500 MHz, CDCl 3 )δ7.78-7.73(m,2H),7.45(dd,J=7.6,1.6Hz,2H),7.24-7.20(m,2H),7.00-6.91(m,4H),6.25(dd,J=8.1,1.4Hz,2H),1.70-1.66(s,6H).

[0589] (2) Synthesis of intermediate 11(2)

[0590]

[0591] 3.8g (1.0eq, 5.2mmol) of 10- (4- bromophenyl) -9,10- dihydro -9,9- dimethyl acridine is added to the reaction vessel, and vacuum dried, and the reaction vessel is filled with nitrogen. 8mL of THF is added thereto to dissolve the compound, and the reaction vessel is cooled to a temperature of -78°C by using dry ice. 6.2mL (1.5eq, 7.7mmol) of 1.6M n-butyl lithium is slowly dripped into the reaction vessel, while maintaining a temperature of -78°C, and stirred for 90 minutes. 1.2mL (1.5eq, 7.7mmol) of dimethylformamide (DMF) is added to the reaction vessel, and stirred at room temperature for 3 hours. After the reaction is completed, the organic layer is extracted therefrom by using distilled water and ethyl acetate. The extracted organic layer is dried by using anhydrous magnesium sulfate, filtered by diatomaceous earth, and the solvent is evaporated therefrom. Then, column chromatography was performed thereon to obtain 2.4 g (yield 74%) of Intermediate 11(2) (ie, 4-(9,9-dimethylacridin-10(9H)-yl)benzaldehyde).

[0592] 1 H NMR (500 MHz, CDCl 3 )δ10.12(s,1H),8.17-8.10(m,2H),7.56-7.52(m,2H),7.51-7.47(m,2H),7.02-6.96(m,4H),6.36-6.30(m,2H),1.69(s,6H).

[0593] (3) Synthesis of Compound 11

[0594]

[0595] 0.74g (1eq, 2.4mmol) of 4-(9,9-dimethylacridine-10(9H)-yl)benzaldehyde, 0.50g (1.0eq, 2.4mmol) of 2,2'-pyridone, 1.1mL (5.0eq, 12mmol) of aniline and 2.3g (12eq, 29mmol) of ammonium acetate were added to a reaction vessel, and vacuum dried, and the reaction vessel was filled with nitrogen. 15mL of acetic acid was added thereto, and refluxed and stirred at a temperature of 120°C for 4 hours. After the reaction was completed, the reaction product was neutralized by using an aqueous sodium hydroxide solution, washed with distilled water, and an organic layer was extracted therefrom by using chloroform. The extracted organic layer was dried by using anhydrous magnesium sulfate, filtered through diatomaceous earth, and the solvent was evaporated therefrom. Then, column chromatography was performed thereon, and recrystallization was performed thereon using dichloromethane and hexane to obtain 0.61 g (yield 45%) of the final compound 11 (9,10-dihydro-9,9-dimethyl-10-(4-(1-phenyl-4,5-di(pyridin-2-yl)-1H-imidazol-2-yl)phenyl)acridine).

[0596] 1 H NMR (500 MHz, CDCl 3 )δ8.49(d,J=25.3Hz,2H),7.87(d,J=8.0Hz,1H),7.74-7.69(m,2H),7.6 5(t,J=6.9Hz,1H),7.62-7.55(m,1H),7.45-7.37(m,3H),7.33-7.28(m,3 H),7.25-7.19(m,4H),7.16-7.09(m,2H),6.94(dtd,J=23.4,7.3,1.5Hz,4H),6.24(dd,J=8.1,1.3Hz,2H),1.66(s,6H), APCI-MS(m / z): 582[M+].

[0597] Synthesis Example 5: Synthesis of Compound 13

[0598] (1) Synthesis of intermediate 13(1)

[0599]

[0600] 2.0g (1.0eq, 11mmol) of 1,10-phenanthroline and 2.1g (1.6eq, 17mmol) of potassium bromide were added to the reaction vessel, and vacuum dried, and the reaction vessel was filled with nitrogen. The reaction vessel was cooled to a temperature of 0°C, and a mixed solution of 40mL of 20mL of sulfuric acid and 20mL of nitric acid was slowly added to the reaction vessel, and stirred to dissolve the compound, and the compound was refluxed and stirred at a temperature of 100°C for 3 hours. After the reaction was completed, the reaction product was neutralized by using sodium carbonate, washed with distilled water, and an organic layer was extracted therefrom by dichloromethane. The extracted organic layer was dried by using anhydrous magnesium sulfate, filtered by diatomaceous earth, and the solvent was evaporated therefrom. Then, dichloromethane and ethanol were used to perform recrystallization to obtain 1.3g (yield of 54%) of intermediate 13 (1) (i.e., 1,10-phenanthroline-5,6-dione).

[0601] 1 H NMR: 9.13 (dd, J = 4.7, 1.8 Hz, 2H), 8.52 (dd, J = 7.9, 1.8 Hz, 2H), 7.60 (dd, J = 7.9, 4.7 Hz, 2H).

[0602] (2) Synthesis of Compound 13

[0603]

[0604] 0.50g (1.0eq, 2.4mmol) of 1,10-phenanthroline-5,6-dione, 0.74g (1.0eq, 2.4mmol) of 4- (9,9-dimethylacridine-10 (9H) -yl) benzaldehyde, 1.1mL (5.0eq, 12mmol) of aniline and 2.1g (12eq, 29mmol) of ammonium acetate were added to a reaction vessel, and vacuum dried, and the reaction vessel was filled with nitrogen. 15mL of acetic acid was added to the reaction vessel to dissolve the compound, and the compound was refluxed and stirred at a temperature of 130°C for 16 hours. After the reaction is completed, the reaction product is neutralized by using sodium carbonate and washed with distilled water, and an organic layer is extracted therefrom by using ethyl acetate. The extracted organic layer is dried by using magnesium sulfate, filtered through diatomaceous earth, and the solvent is evaporated therefrom. After column chromatography, it was recrystallized using ethanol to obtain 0.50 g (yield 37%) of the final compound 13 (2-(4-(9,9-dimethylacridin-10(9H)-yl)phenyl)-1-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline).

[0605] 1H NMR: 9.21(ddd,J=9.8,6.2,1.8Hz,2H),9.07(dt,J=23.2,11.6Hz,1H),7.91- 7.83(m,2H),7.79(dd,J=8.1,4.4Hz,1H),7.74-7.68(m,3H),7.67-7.60(m,2 H),7.51(dd,J=8.4,1.6Hz,1H),7.48-7.43(m,2H),7.32(ddd,J=8.5,7.5,3. 1Hz, 3H), 7.01-6.87 (m, 4H), 6.29-6.17 (m, 2H), 1.36 (dd, J = 17.1, 5.7Hz, 6H). APCI-MS (m / z): 580 [M+].

[0606] Synthesis Example 6: Synthesis of Compound 15

[0607] (1) Synthesis of intermediate 15(1)

[0608]

[0609] 0.80g (1.0eq, 4.4mmol) of 10H-benzoxazine, 1.6g (1.3eq, 5.7mmol) of 4-bromoiodobenzene, 0.090g (0.080eq, 0.35mmol) of 18-crown ether-6, 0.14g (0.52eq, 2.3mmol) of copper (powder) and 2.4g (4.0eq, 17mmol) of potassium carbonate were added to the reaction vessel, and vacuum dried, and the reaction vessel was filled with nitrogen. 11mL of 1,2-dichlorobenzene was added to the reaction vessel, and refluxed and stirred at a temperature of 190°C for 2 hours. After the reaction was completed, the organic layer was extracted therefrom using distilled water and ethyl acetate. The extracted organic layer was dried using anhydrous magnesium sulfate, filtered through diatomaceous earth, and the solvent was evaporated therefrom. Then, column chromatography was performed thereon to obtain 1.1 g (yield 72%) of Intermediate 15(1) (ie, 10-(4-bromophenyl)-10H-benzoxazine).

[0610] 1 H NMR (500 MHz, CDCl 3 )δ7.75-7.70(m,2H),7.25-7.22(m,2H),6.67(dtd,J=9.2,7.8,1.6Hz,4H),6.60(td,J=7.6,1.7Hz,2H),5.94-5.88(m,2H).

[0611] (2) Synthesis of intermediate 15(2)

[0612]

[0613] 0.80g (1.0eq, 2.4mmol) of 10- (4- bromophenyl) -10H- benzoxazine is added to the reaction vessel, and vacuum dried, and the reaction vessel is filled with nitrogen. 8mL of THF is added thereto to dissolve the compound, and the reaction vessel is cooled to a temperature of -78°C by using dry ice. 2.2mL (1.5eq, 3.5mmol) of 1.6M n-butyl lithium is slowly added dropwise to the reaction vessel, while maintaining a temperature of -78°C, and stirred for 90 minutes. 0.27mL (1.5eq, 3.5mmol) of dimethylformamide is added to the reaction vessel, and stirred at room temperature for 3 hours. After the reaction is completed, the organic layer is extracted therefrom by using distilled water and ethyl acetate. The extracted organic layer is dried by using anhydrous magnesium sulfate, and filtered by diatomaceous earth, and the solvent is evaporated therefrom. Then, column chromatography was performed thereon to obtain 0.40 g (yield 59%) of Intermediate 15(2) (ie, 4-(10H-benzoxazin-10-yl)benzaldehyde).

[0614] 1 H NMR (500 MHz, CDCl 3 )δ10.11(s,1H),8.16-8.08(m,2H),7.62-7.51(m,2H),6.71(dtd,J=9.3,7.9, 1.6Hz, 4H), 6.61 (ddd, J=17.8, 10.1, 6.1Hz, 2H), 5.96 (dd, J=8.0, 1.4Hz, 2H).

[0615] (3) Synthesis of Compound 15

[0616]

[0617] 0.28 g (1.2 eq, 0.97 mmol) of 4-(10H-benzoxazin-10-yl)benzaldehyde and 0.15 g (1.0 eq, 0.81 mmol) of N 2-phenylpyridine-2,3-diamine is added to the reaction vessel, and vacuum dried, and the reaction vessel is filled with nitrogen. 5mL of acetic acid is added thereto, and refluxed and stirred at a temperature of 120°C for 3 hours. After the reaction is completed, the reaction product is neutralized by using sodium carbonate, and an organic layer is extracted therefrom by using distilled water and ethyl acetate. The extracted organic layer is dried by using anhydrous magnesium sulfate, and filtered by diatomaceous earth, and the solvent is evaporated therefrom. After column chromatography, dichloromethane and hexane are used to perform recrystallization on it, to obtain 0.25g (yield is 69%) of final compound 15 (10-(4-(3-phenyl-3H-imidazo [4,5-b] pyridine-2-yl) phenyl)-10H-benzoxazine).

[0618] 1 H NMR (500 MHz, CDCl 3 )δ8.42(dd,J=4.8,1.5Hz,1H),8.17(dd,J=8.0,1.5Hz,1H),7.85-7.81(m,2H),7.59-7.52(m,2H),7.52-7.48(m,1H),7.44(dt,J=8 .7,2.7Hz,2H),7.35-7.30(m,2H),7.27-7.23(m,1H),6.69-6.61(m,4H),6.58(td,J=7.6,1.7Hz,2H),5.92(dd,J=7.9,1.4Hz,2H). APCI-MS(m / z): 453[M+].

[0619] Synthesis Example 7: Synthesis of Compound 25

[0620] (1) Synthesis of Intermediate 25(1)

[0621]

[0622] 1.0g (1.0eq, 4.4mmol) of 2- (phenylamino) benzoic acid methyl ester is added to the reaction vessel, and vacuum dried, and the reaction vessel is filled with nitrogen. 17mL of THF is added to the reaction vessel, and stirred to dissolve the compound, and the reaction vessel is cooled to a temperature of -78°C. 1.9M phenyl lithium (3.0eq, 7.0mL) is slowly dripped therein, and stirred for 1 hour at a temperature of -78°C. The reaction solution is stirred for 2 hours at a temperature of 0°C, and then additionally stirred at room temperature for 4 hours. After the reaction is completed, the reaction product is washed with distilled water, and the organic layer is extracted therefrom by using chloroform. The extracted organic layer is dried by using anhydrous magnesium sulfate, and filtered by diatomaceous earth, and the solvent is evaporated therefrom. The dried reaction product is added to the reaction vessel, and 20mL of chloroform is added thereto to dissolve the compound. 1mL of methanesulfonic acid (MSA) is added thereto, and refluxed and stirred for 1 hour. After the reaction was completed, the reaction product was neutralized by using a sodium bicarbonate aqueous solution, and an organic layer was extracted therefrom by using distilled water and chloroform. The extracted organic layer was dried by using anhydrous magnesium sulfate, filtered through diatomaceous earth, and the solvent was evaporated therefrom. After column chromatography, it was recrystallized using chloroform and hexane to obtain 1.1 g (yield 73%) of intermediate 25 (1) (i.e., 9,9-diphenyl-9,10-dihydroacridine).

[0623] 1 H NMR: 7.26-7.15 (m, 8H), 6.96-6.94 (m, 4H), 6.89 (td, J = 7.5Hz, 1.2Hz, 2H), 6.83 (dd, J = 7.8Hz, 1.5Hz, 2H), 6.80 (dd, J = 7.9Hz, 1.1Hz, 2H), 6.28 (s, 1H).

[0624] (2) Synthesis of Compound 25

[0625]

[0626] 0.50g (1.0eq, 1.4mmol) of 2-(4-bromophenyl)-3-phenyl-3H-imidazo[4,5-b]pyridine, 0.52g (1.1eq, 1.6mmol) of 9,9-diphenyl-9,10-dihydroacridine, 0.13g (0.10eq, 0.14mmol) of tris(dibenzylideneacetone)dipalladium(0) and 0.52g (4.0eq, 5.7mmol) of sodium tert-butoxide were added to a reaction vessel, and vacuum dried, and the reaction vessel was filled with nitrogen. 9mL of toluene was added to the reaction vessel to dissolve the compound, and 0.060g (0.20eq, 0.28mmol) of tri-tert-butylphosphine was added thereto and refluxed at a temperature of 110°C for 2 hours. After the reaction was completed, the reaction product was washed with distilled water, and an organic layer was extracted therefrom by using ethyl acetate. The extracted organic layer was dried by using magnesium sulfate, filtered through celite, and the solvent was evaporated therefrom. After column chromatography, it was recrystallized using dichloromethane and hexane to obtain 0.57 g (yield 66%) of the final compound 25 (9,9-diphenyl-10-(4-(3-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)phenyl)-9,10-dihydroacridine).

[0627] 1 H NMR: 8.46-8.38(m,1H),8.17(dt,J=10.5,5.3Hz,1H),7.81-7.72(m,2H),7.60-7.53(m,2H),7.53-7.47(m,1H),7.47-7.41(m,2H),7.34(dd ,J=8.0,4.8Hz,1H),7.25-7.20(m,6H),7.11-7.06(m,2H),7.06-7.01(m,2H),7.00-6.94(m,4H),6.92-6.86(m,4H),6.39(d,J=8.2Hz,2H). APCI-MS(m / z): 603[M+].

[0628] Synthesis Example 8: Synthesis of Compound 74

[0629] (1) Synthesis of intermediate 74(1)

[0630]

[0631] 10g (1.0eq, 63mmol) of 2-chloro-3-nitropyridine is added to a reaction vessel, and vacuum dried, and the reaction vessel is filled with nitrogen. Then, 5.8mL (1.0eq, 63mmol) of aniline and 100mL of ethylene glycol are added thereto, and refluxed and stirred at a temperature of 140°C for 8 hours. After the reaction is complete, the reaction vessel is cooled to room temperature, and an organic layer is extracted therefrom by using distilled water and ethyl acetate. The extracted organic layer is dried by using anhydrous magnesium sulfate, and filtered by diatomaceous earth, and the solvent is evaporated therefrom. Then, column chromatography is performed to obtain 12g (yield is 87%) of intermediate 74 (1) (i.e. 3-nitro-N-phenylpyridine-2-amine).

[0632] 1 H NMR (500 MHz, CDCl 3 )δ10.12(s,1H),8.53(dd,J=8.3,1.8Hz,1H),8.49(dd,J=4.5,1.8Hz,1H),7.65(dt,J =8.7,1.6Hz,2H),7.42-7.38(m,2H),7.21-7.17(m,1H),6.83(dd,J=8.3,4.5Hz,1H).

[0633] (2) Synthesis of intermediate 74(2)

[0634]

[0635] 12 g (1.0 eq, 55 mmol) of 3-nitro-N-phenylpyridin-2-amine and 37 g (3.0 eq, 160 mmol) of SnCl 2 ·2H 2 O was added to the reaction container, vacuum dried, and filled with nitrogen. 300 mL of methanol was added thereto and refluxed at 60° C. for 2 hours. NaHCO was added thereto. 3 The aqueous solution was added to complete the reaction, and an organic layer was extracted therefrom by using distilled water and ethyl acetate. The extracted organic layer was dried by using anhydrous magnesium sulfate, filtered through celite, and the solvent was evaporated therefrom. Then, it was recrystallized using dichloromethane and hexane to obtain 8.2 g (yield 81%) of Intermediate 74 (2) (i.e., N 2 -phenylpyridine-2,3-diamine).

[0636] 1 H NMR (500 MHz, CDCl 3)δ7.84(dd,J=4.9,1.5Hz,1H),7.31-7.24(m,4H),7.02(dd,J=7.6,1.6Hz,1H),6. 96(tt,J=7.1,1.6Hz,1H), 6.78(dd,J=7.6,4.9Hz,1H), 6.19(s,1H), 3.41(s,2H).

[0637] (3) Synthesis of intermediate 74(3)

[0638]

[0639] Methyl anthranilate (9.0 mL, 0.070 mol), methyl 2-iodobenzoate (30 mL, 0.20 mol), K 2 CO 3 74 (3) (i.e. yellow solid triester tertiary amine) (22 g, 75% yield) was added to 1H- 2- nitric acid ester (22 g, 0.16 mol), Cu (0.90 g, 14 mmol) and CuI (1.3 g, 6.8 mmol) were added to a reaction vessel, and vacuum dried, and the reaction vessel was filled with nitrogen. Then, diphenyl ether (80 mL) was added thereto, and refluxed at a temperature of 190 ° C for 6 days. The solvent was removed therefrom under reduced pressure, and the solid thus obtained was dissolved by using EA and methanol. Then, column chromatography was performed to obtain intermediate 74 (3) (i.e. yellow solid triester tertiary amine) (22 g, 75% yield).

[0640] 1 H NMR (500 MHz, CDCl 3 )δ7.58(d,J 7.7Hz,3H),7.35(t,J 7.6Hz,3H),7.0-7.14(m,6H),3.37(s,9H).

[0641] (4) Synthesis of Intermediate 74(4)

[0642]

[0643] 45mL (15eq, 89mmol) of methylmagnesium iodide (2M) was vacuum dried, added to a reaction vessel filled with nitrogen, and then stirred. 2.5g (1.0eq, 2.0mmol) of intermediate 74 (3) (i.e., triester tertiary amine) was dissolved in 70mL of toluene and then slowly added to the reaction vessel. The reaction solution was refluxed and stirred for 15 hours at a temperature of 110°C. After the reaction was completed, the reaction product was cooled to room temperature and the reaction was slowly terminated by sulfuric acid. The reaction product was washed with distilled water and an organic layer was extracted therefrom using MC. The extracted organic layer was dried using magnesium sulfate and filtered through diatomaceous earth. Then, column chromatography (EA: hexane = 1: 5) was performed to obtain 0.90g (yield of 36%) of intermediate 74 (4) (i.e., white solid triolamine).

[0644] 1 H NMR (500 MHz, CDCl 3 )δ7.32(d,J 9.0Hz,3H),7.0-7.15(m,6H),6.68(d,J 7.3Hz,3H),5.37(s,3H),1.67(s,9H),0.84(s,9H).

[0645] (5) Synthesis of Intermediate 74(5)

[0646]

[0647] The intermediate 74 (4) (i.e., triolamine) (0.90 g, 2.2 mmol) was added to the reaction vessel, and an 85% phosphoric acid aqueous solution (10 mL) was added thereto, and stirred at room temperature for 2 hours. After the reaction was completed, the reaction was terminated by NaOH, the reaction product was washed with distilled water, and an organic layer was extracted therefrom by using MC. Then, column chromatography was performed using hexane to obtain 0.46 g (yield 59%) of the intermediate 74 (5) (i.e., white solid triarylamine).

[0648] 1 H NMR (500 MHz, CDCl 3 )δ7.37(d,J 7.7Hz,6H),7.12(t,J 7.8Hz,3H),1.63(s,18H).

[0649] (6) Synthesis of Intermediate 74(6)

[0650]

[0651] 0.40 g (1.0 eq, 1.1 mmol) of intermediate 74 (5) (i.e., triarylamine) was added to a reaction vessel, vacuum dried, and filled with nitrogen. 40 mL of DMF was added thereto, and the reaction vessel was cooled to 0° C. using ice. 1.7 mL of POCl was mixed in another reaction vessel. 3 And 5mL of DMF, and the reaction vessel was cooled to a temperature of 0°C. The mixture was slowly dripped and stirred at room temperature until its color changed to brown. Then, the reaction vessel was heated to a temperature of 80°C and stirred for 15 hours. After the reaction was completed, the reaction was terminated by sodium acetate, and the reaction solution was extracted by using MC. The reaction product was dried by using magnesium sulfate, filtered through diatomaceous earth, and column chromatography was performed to obtain 0.29g (yield 67%) of intermediate 74 (6) (i.e. yellow solid 4,4,8,8,12,12-hexamethyl-8,12-dihydro-4H-benzo [9,1] quinolizine and acridine-2-carboxaldehyde).

[0652] 1 H NMR (300 MHz, CDCl 3 )δ9.93(s,1H),7.89(s,2H),7.42(dd,J 7.6,2.3Hz,4H),7.20(t,J 7.6Hz,2H),1.67(s,6H),1.65(s,12H).

[0653] (7) Synthesis of Compound 74

[0654]

[0655] 0.14 g (1.0 eq, 7.6 mmol) of N 2 -phenylpyridine-2,3-diamine and 0.33g (1.1eq, 0.83mmol) of 4,4,8,8,12,12-hexamethyl-8,12-dihydro-4H-benzo [9,1] quinolizine and acridine-2-carboxaldehyde were added to the reaction vessel, and vacuum dried, and the reaction vessel was filled with nitrogen. Then, 10mL of ethanol was added thereto, and refluxed and stirred at a temperature of 80°C for 3 days. After the reaction was completed, the reaction product was washed with distilled water, and the organic layer was extracted therefrom by using EA. After column chromatography (EA: hexane = 1: 4), MC and hexane were used to perform recrystallization to obtain 0.11g (yield 26%) of the final compound 74 as a yellow solid.

[0656] 1 H NMR (500 MHz, CDCl 3)δ8.36(dd,J=4.8,1.3Hz,1H),8.17(dd,J=8.0,1.3Hz,1H),7.65(s,2H),7.55(t,J=7.6Hz,2H),7.48(d,J=7.4Hz,1H),7.44(dd,J=6.8,5.5Hz,2H) ,7.38(dd,J=7.7,1.4Hz,2H),7.33(dd,J=7.7,1.4Hz,2H),7.29(dd,J=8.0,4.8Hz,1H),7.13(t,J=7.7Hz,2H),1.63(d,J=7.4Hz,6H),1.45(s,12H).

[0657] Synthesis Example 9: Synthesis of Compound 83

[0658] (1) Synthesis of intermediate 83(1)

[0659]

[0660] 2.0 g (1.0 eq, 17 mmol) of 4-aminobenzonitrile and 0.81 g (2.0 eq, 34 mmol) of sodium hydride were added to a reaction vessel, vacuum dried, and filled with nitrogen. DMF was added thereto and stirred for about 30 minutes, and 2-chloro-3-nitropyridine was added thereto and refluxed at a temperature of 100° C. for 9 hours. After the reaction was completed, the reaction was terminated by using distilled water. The reaction product was washed and an organic layer was extracted therefrom using ethyl acetate. The extracted organic layer was dried using magnesium sulfate, filtered through diatomaceous earth, and the solvent was evaporated therefrom. Then, column chromatography was performed to obtain 0.95 g (yield of 31%) of intermediate 83 (1) (i.e. 4- (3-nitropyridine-2-ylamino) benzonitrile).

[0661] 1 H NMR (500 MHz, CDCl 3 )δ10.36(s,1H),8.85-8.29(m,2H),8.08-7.76(m,2H),7.81-7.50(m,2H),7.02(ddd,J=19.9,8.4,4.6Hz,1H).

[0662] (2) Synthesis of intermediate 83(2)

[0663]

[0664] 0.50g (1.0eq, 2.1mmol) of 4- (3-nitropyridine -2- amino) benzonitrile and 15mL of MeOH were added to the reaction vessel, and 1.9g (4.0eq, 8.3mmol) of dihydrated tin (II) was added thereto little by little, while slowly raising the temperature. Then, the reaction mixture was refluxed at a temperature of 80°C for 1 hour. After the reaction was completed, the reaction was terminated by using sodium bicarbonate, the reaction product was washed, and an organic layer was extracted therefrom by using ethyl acetate. The extracted organic layer was dried by using magnesium sulfate, filtered through diatomaceous earth, and the solvent was evaporated therefrom. Then, column chromatography was performed to obtain 0.42g (yield of 96%) of intermediate 83 (2) (i.e. 4- (3-aminopyridine -2- amino) benzonitrile).

[0665] 1 H NMR (500 MHz, CDCl 3 )δ7.94-7.81(m,1H),7.61-7.52(m,2H),7.41-7.34(m,2H),7.13-7.04(m,1H),6.92-6.82(m,1H),6.52(s,1H),3.45(s,2H).

[0666] (3) Synthesis of intermediate 83(3)

[0667]

[0668] Methyl anthranilate (9.0 mL, 0.070 mol), methyl 2-iodobenzoate (30 mL, 0.20 mol), K 2 CO 3 (22g, 0.16mol), Cu (0.90g, 14mmol) and CuI (1.3g, 6.8mmol) were added to a reaction vessel, and vacuum dried, and the reaction vessel was filled with nitrogen. Then, diphenyl ether (80mL) was added thereto, and stirred at a temperature of 190°C for 6 days. The solvent was removed therefrom under reduced pressure, and the solid thus obtained was dissolved by using EA and methanol. Then, column chromatography was performed to obtain 22g (yield of 75%) of intermediate 83 (3) (i.e. yellow solid triester tertiary amine).

[0669] 1 H NMR (500 MHz, CDCl 3 )δ7.58(d,J 7.7Hz,3H),7.35(t,J 7.6Hz,3H),7.0-7.14(m,6H),3.37(s,9H).

[0670] (4) Synthesis of Intermediate 83(4)

[0671]

[0672] 45mL (15eq, 89mmol) of methylmagnesium iodide (2M) was vacuum dried, added to a reaction vessel filled with nitrogen, and then stirred. 2.5g (1.0eq, 2.0mmol) of intermediate 83 (4) (i.e., triester tertiary amine) was dissolved in 70mL of toluene and then slowly added to the reaction vessel. The reaction mixture was refluxed and stirred for 15 hours at a temperature of 110°C. After the reaction was completed, the reaction product was cooled to room temperature and the reaction was slowly terminated by sulfuric acid. Then, the reaction product was washed with distilled water and an organic layer was extracted therefrom using MC. The extracted organic layer was dried using magnesium sulfate and filtered through diatomaceous earth. Then, column chromatography (EA: hexane = 1: 5) was performed to obtain 0.90g (yield of 36%) of intermediate 83 (4) (i.e., white solid triolamine).

[0673] 1 H NMR (500 MHz, CDCl 3 )δ7.32(d,J 9.0Hz,3H),7.0-7.15(m,6H),6.68(d,J 7.3Hz,3H),5.37(s,3H),1.67(s,9H),0.84(s,9H).

[0674] (5) Synthesis of Intermediate 83(5)

[0675]

[0676] The intermediate 83 (4) (i.e., triolamine) (0.90 g, 2.2 mmol) was added to the reaction vessel, 85% aqueous phosphoric acid solution (10 mL) was added thereto, and the reaction mixture was stirred at room temperature for 2 hours. After the reaction was completed, the reaction was terminated by NaOH. The reaction product was then washed with distilled water, and the organic layer was extracted using MC. Then, column chromatography was performed on it using hexane to obtain 0.46 g (yield 59%) of the intermediate 83 (5) (i.e., white solid triarylamine).

[0677] 1 H NMR (500 MHz, CDCl 3 )δ7.37(d,J 7.7Hz,6H),7.12(t,J 7.8Hz,3H),1.63(s,18H).

[0678] (6) Synthesis of Intermediate 83(6)

[0679]

[0680] 0.40 g (1.0 eq, 1.1 mmol) of intermediate 83 (5) (i.e., triarylamine) was added to a reaction vessel, vacuum dried, and filled with nitrogen. 40 mL of DMF was added thereto, and the reaction vessel was cooled to 0° C. using ice. 1.7 mL of POCl was mixed in another reaction vessel. 3 And 5mL of DMF, and the reaction vessel was cooled to a temperature of 0°C. The mixture was slowly dripped and stirred at room temperature until its color changed to brown. Then, the reaction vessel was heated to a temperature of 80°C, and the reaction mixture was stirred for 15 hours. After the reaction was completed, the reaction was terminated by sodium acetate, and the reaction solution was extracted by using MC. The extracted reaction solution was dried by using magnesium sulfate and filtered through diatomaceous earth. Then, column chromatography was performed to obtain 0.29g (yield 67%) of intermediate 83 (6) (i.e. yellow solid 4,4,8,8,12,12-hexamethyl-8,12-dihydro-4H-benzo [9,1] quinolizine and acridine-2-carboxaldehyde).

[0681] 1 H NMR (300 MHz, CDCl 3 )δ9.93(s,1H),7.89(s,2H),7.42(dd,J 7.6,2.3Hz,4H),7.20(t,J 7.6Hz,2H),1.67(s,6H),1.65(s,12H).

[0682] (7) Synthesis of Compound 83

[0683]

[0684] 0.16g (1.1eq, 7.6mmol) of 4- (3-aminopyridin-2-ylamino) benzonitrile, 0.28g (1.0eq, 0.71mmol) of 4,4,8,8,12,12-hexamethyl-8,12-dihydro-4H-benzo [9,1] quinolizine and acridine-2-carboxaldehyde and 0.020g (0.10eq, 0.070mmol) of indium chloride were added to a reaction vessel, and vacuum dried, and the reaction vessel was filled with nitrogen. Then, 10mL of ethanol was added thereto, and refluxed at a temperature of 80°C for several hours. After the reaction was completed, the solvent was removed therefrom under reduced pressure. Then, the solid thus obtained was added to a reaction vessel and vacuum dried, and the reaction vessel was filled with nitrogen. 10mL of DMF was added to the reaction vessel, and refluxed at a temperature of 100°C for 9 hours. After the reaction was completed, the organic layer was extracted therefrom by using ethyl acetate. The extracted organic layer was dried by using magnesium sulfate and filtered through celite. Then, column chromatography (EA:hexane=1:4) was performed thereon to obtain 0.20 g (yield 49%) of the final compound 83.

[0685] 1 H NMR (500 MHz, CDCl 3 )δ8.36(dd,J=4.8,1.4Hz,1H),8.19(dd,J=8.0,1.4Hz,1H),7.85-7.78(m,2H),7.62 -7.49(m,4H),7.44-7.32(m,5H),7.16(t,J=7.7Hz,2H),1.66(s,6H),1.46(s,12H).

[0686] By referring to the above-mentioned synthesis mechanism and method, those skilled in the art can also easily recognize the synthesis method of compounds other than the above-mentioned compounds.

[0687] Example 1

[0688] Referring to the compound shown below, the ITO glass substrate was cut into a size of 50 mm×50 mm×0.5 mm, and was cleaned by ultrasonication using isopropyl alcohol and pure water for 10 minutes each, and then exposed to ultraviolet rays and ozone for 10 minutes. Then, the ITO glass substrate was provided to a vacuum deposition device, and a material NPB was vacuum-deposited on the ITO glass substrate to form a A hole injection layer having a thickness of , and a hole transport material mCP is vacuum deposited on the hole injection layer to form a Compound 9 and mCBP were co-deposited on the hole transport layer at a weight ratio of 15:85 to form a Then, ETL1 is deposited on the emission layer to form an emission layer having a thickness of An electron transport layer having a thickness of , and Al is vacuum deposited on the electron transport layer to form a An Al electrode with a thickness of , thereby completing the manufacture of the organic light-emitting device.

[0689]

[0690] Examples 2 to 7 and Comparative Examples 1 to 4

[0691] An organic light emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 were each used instead of Compound 9 in forming the emission layer.

[0692]

[0693] [Evaluation example]

[0694] The luminance was measured by using a current-voltage meter (Keithley SMU 236) and a luminance meter PR650 at 10 mA / cm 2 The driving voltage, current efficiency, and external quantum efficiency of the organic light emitting devices manufactured according to Examples 1 to 7 and Comparative Examples 1 to 4 were measured at a current density of , and the results are shown in Table 1.

[0695] [Table 1]

[0696]

[0697] Referring to Table 1, it can be seen that the organic light-emitting device using the compound according to the example embodiment in the emission layer has an equal or lower level of driving voltage and an equal or higher level of external quantum efficiency, and has improved current efficiency, compared with the driving voltage, external quantum efficiency, and current efficiency of the organic light-emitting devices of Comparative Examples 1 to Comparative Examples 4.

[0698] As described above, the organic light emitting device including the heterocyclic compound according to the embodiment may have low driving voltage, high efficiency, and long lifespan.

[0699] Example embodiments have been disclosed herein, and although specific terms are employed, they are used and interpreted in a general and descriptive sense only and not for purposes of limitation. In some cases, as will be apparent to one of ordinary skill in the art, as of the time of filing this application, features, characteristics, and / or elements described in connection with a specific embodiment may be used alone or in combination with features, characteristics, and / or elements described in connection with other embodiments, unless otherwise specifically noted. Therefore, it will be understood by those skilled in the art that various changes in form and detail may be made without departing from the spirit and scope of the invention as set forth in the claims.

Claims

1. An organic light-emitting device, comprising: a first electrode; a second electrode, facing the first electrode; as well as An organic layer is located between the first electrode and the second electrode and includes an emission layer, wherein the emission layer includes a heterocyclic compound represented by Formula 1 as a dopant: <Formula 1> Among them, in formula 1, A1 is a group represented by formula 2, <Formula 2> In equation 1 and equation 2, X1 is O, S or N(R3), X2 is O, S, N(R4), C(R4)(R5) or Si(R4)(R5), Y1 and Y2 are independently C(R6)(R7) or Si(R6)(R7), m1 is 0 or 1, m2 is 0 or 1, R3 is substituted or unsubstituted C6-C 60 Aryl, R1, R2, R4, R5, R6, R7, R 10 , R 20 and R 30 are independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl or substituted or unsubstituted C6-C 60 Aryl, R1 to R7, R 10 , R 20 and R 30 Two or more adjacent substituents in the group may be optionally linked to form a substituted or unsubstituted C5-C 60 Carbocyclic or substituted or unsubstituted C1-C 60 Heterocyclic group, When m1 and m2 are both 1, R1 and R2 are connected to form a substituted or unsubstituted C1-C 60 Heterocyclic group, When m1 and m2 are both 0, A1 is express, Wherein, X1 is O, S or N(R3), R 41 and R 42 Are independently: Phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thirolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothirolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl , tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothiophenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthothiophenyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazopyridyl, benzonaphthyridinyl, azafluorenyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzothiophenyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl or indolocarbazolyl, b10, b20 and b30 are each independently an integer from 1 to 4, The substituted C5-C 60 Carbocyclic group, the substituted C1-C 60 Heterocyclic group, the substituted C1-C 60 Alkyl and the substituted C6-C 60 At least one substituent in the aryl group is: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy; C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio or C1-C 60 heteroaryl; 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 Q 31 To Q 33 are independently 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 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 Heteroarylbiphenyl or terphenyl.

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

3. The organic light emitting device according to claim 1, wherein: The heterocyclic compound included in the emission layer satisfies Formula 1: <Formula 1> │E D,S1 -E D,T1 │≤0.3eV, In formula 1, E D,S1 is the singlet energy level of the heterocyclic compound, and E D,T1 is the triplet energy level of the heterocyclic compound.

4. The organic light emitting device according to claim 1, wherein: The heterocyclic compound is one of Compound 10, Compound 11, Compound 20, Compound 21, Compound 30, Compound 31, Compound 40, Compound 41, Compound 50, Compound 51, Compound 60, Compound 70, Compound 71, Compounds 74-78, Compounds 82-86 and Compound 94:

5. A heterocyclic compound, the heterocyclic compound is represented by Formula 1: <Formula 1> in, In formula 1, A1 is a group represented by formula 2-1, <Formula 2-1> In Formula 1 and Formula 2-1, X1 is O, S or N(R3), X2 is O, S, N(R4), C(R4)(R5) or Si(R4)(R5), Y1 and Y2 are independently C(R6)(R7) or Si(R6)(R7), m1 is 0, m2 is 0, R3 is substituted or unsubstituted C6-C 60 Aryl, R 41 and R 42 Are independently: Phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thirolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothirolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl , tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothiophenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthothiophenyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazopyridyl, benzonaphthyridinyl, azafluorenyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzothiophenyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl or indolocarbazolyl, R4, R5, R6, R7, R 10 , R 20 and R 30 are independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl or substituted or unsubstituted C6-C 60 Aryl, R3 to R7, R 10 , R 20 and R 30 Two or more adjacent substituents may be optionally linked to form a substituted or unsubstituted C5-C 60 Carbocyclic or substituted or unsubstituted C1-C 60 Heterocyclic group, b10, b20 and b30 are each independently an integer from 1 to 4, The substituted C5-C 60 Carbocyclic group, the substituted C1-C 60 Heterocyclic group, the substituted C1-C 60 Alkyl and the substituted C6-C 60 At least one substituent in the aryl group is: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy; C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio or C1-C 60 heteroaryl; 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 Q 31 To Q 33 are independently 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 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 Heteroarylbiphenyl or terphenyl.

6. The heterocyclic compound according to claim 5, wherein R3 is: Phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl or pentacene; or are substituted with deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrene, yl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thirolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl yl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthothioyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazopyridyl, benzonaphthyridinyl, azafluorenyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzothioyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl, indolocarbazolyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)(Q 31 )、-S(=O)2(Q 31 )、-P(=O)(Q 31 )(Q 32 ) or -P(=S)(Q 31 )(Q 32 ) of phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl or pentacene.

7. The heterocyclic compound according to claim 5, wherein R4, R5, R6, R7, R 10 , R 20 and R 30 Are independently: hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl; methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl, all of which are substituted with deuterium, -F, -Cl, -Br, -I, cyano, phenyl or biphenyl; Phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thirolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothirolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzosilyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthosilyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazolopyridyl, benzonaphthyridinyl, azafluorenyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzosilyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl or indolocarbazolyl; or are substituted with deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrene, yl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thirolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl yl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthothioyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazopyridyl, benzonaphthyridinyl, azafluorenyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzothioyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl, indolocarbazolyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)(Q 31 )、-S(=O)2(Q 31 )、-P(=O)(Q 31 )(Q 32 ) or -P(=S)(Q 31 )(Q 32 ) of phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thirolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothirolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzosilyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthosilyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazolopyridyl, benzonaphthyridinyl, azafluorenyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzosilyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl or indolocarbazolyl, and R1, R2, R4, R5, R6, R7, R 10 , R 20 and R 30 Two or more adjacent substituents may be optionally linked to form a substituted or unsubstituted C5-C 60 Carbocyclic or substituted or unsubstituted C1-C 60 Heterocyclic group.

8. The heterocyclic compound according to claim 5, wherein The heterocyclic compound represented by Formula 1 is represented by Formula 10A: <Formula 10A> Wherein, in Formula 10A, A1 and X2 are the same as described in claim 4, R 11 To R 14 are independently the same as R in claim 4 10 The same definition, R 21 To R 24 are independently the same as R in claim 4 20 The same definition, R 31 To R 34 are independently the same as R in claim 4 30 The definition is the same.

9. The heterocyclic compound according to claim 5, wherein The heterocyclic compound is one of Compound 10, Compound 11, Compound 20, Compound 21, Compound 30, Compound 31, Compound 40, Compound 41, Compound 50, Compound 51, Compound 60, Compound 70 and Compound 71:

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