Amine compound and organic light-emitting device containing the same

Abstract

To provide an amine compound and an organic light-emitting element including the same.SOLUTION: The amine compound is represented by the following chemical formula 1, and the organic light-emitting element includes the amine compound. L1-L4 and L11-L12 each independently represent a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group; a1-a4, a11 and a12 each independently represent an integer selected from 0-5; and Ar1-Ar4 each independently represent a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group, provided that the case where two or more of Ar1-Ar4 include an amino group is excluded.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to an amine compound and an organic light-emitting device containing the same. [Background technology]

[0002] An organic light emitting device is a self-emitting device that has a wider viewing angle and better contrast than conventional devices, as well as a shorter response time, superior brightness, driving voltage, and response speed characteristics, and is capable of multiple colors.

[0003] An organic light-emitting device may have a structure in which a first electrode is disposed on a substrate, and a hole transport region, an emitting layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. Holes injected from the first electrode travel to the emitting layer via the hole transport region, and electrons injected from the second electrode travel to the emitting layer via the electron transport region. Carriers such as holes and electrons recombine in the emitting layer region to generate excitons. Light is generated as the excitons change from their excited state to their ground state. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] U.S. Patent No. 4,720,432 Summary of the Invention [Problem to be solved by the invention]

[0005] The problem to be solved by the present invention is to provide an amine compound and an organic light-emitting device containing the same. [Means for solving the problem]

[0006] According to one embodiment, there is provided an amine compound represented by the following formula 1: [Chemical formula 1] [ka] L1 to L4, and L 11 ~L 12 are, independently of each other, substituted or unsubstituted C5-C 60 Carbocyclic groups or substituted or unsubstituted C1-C 60 is a heterocyclic group, a1 to a4, a11, and a12 are each independently an integer selected from 0 to 5, Ar1 to Ar4 are each independently a substituted or unsubstituted C5-C 60 Carbocyclic groups or substituted or unsubstituted C1-C 60 is a heterocyclic group, However, if two or more of Ar1 to Ar4 contain an amino group, this is excluded. R1 to R3 are hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, or a substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 Alkenyl groups, substituted or unsubstituted C2-C 60 Alkynyl groups, substituted or unsubstituted C1-C 60 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C6-C 60 Aryloxy groups, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), or -P(=O)(Q1)(Q2); D1 to D3 are deuterium; b1 to b3 and c1 to c3 are each independently an integer selected from 0 to 4, However, b1+c1, b2+c2, and b3+c3 are each 4, However, c1+c2+c3 is 1 or greater, The aforementioned substituted C5-C 60 Carbocyclic groups, substituted C1-C 60 Heterocyclic groups, substituted C1-C 60 Alkyl groups, substituted C2-C 60 Alkenyl groups, substituted C2-C 60 Alkynyl groups, substituted C1-C 60 Alkoxy groups, substituted C3-C 10 Cycloalkyl groups, substituted C1-C 10 Heterocycloalkyl groups, substituted C3-C 10 Cycloalkenyl groups, substituted C1-C 10 Heterocycloalkenyl groups, substituted C6-C 60 Aryl groups, substituted C6-C 60 Aryloxy groups, substituted C6-C 60 Arylthio groups, substituted C1-C 60 At least one of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituent of the substituted monovalent non-aromatic fused polycyclic heterocyclic group is Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C60 Alkynyl groups, C1-C 60 Alkoxy groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl group, 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 ) C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups and C1-C 60 Alkoxy groups; C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups and monovalent non-aromatic fused heteropolycyclic groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl group, 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 ) C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; and -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 ); The aforementioned Q1 to Q3, Q 11 ~Q 13 , Q 21 ~Q 23 , and Q 31 ~Q 33 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C1-C 60 It is selected from the group consisting of heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic hetero-fused polycyclic groups, biphenylyl groups, and terphenylyl groups.

[0007] According to another embodiment, there is provided an organic light emitting device including a first electrode, a second electrode facing the first electrode, and an organic layer disposed between the first electrode and the second electrode and including an emitting layer, wherein the organic light emitting device includes one or more amine compounds represented by Chemical Formula 1 as described above. [Effects of the Invention]

[0008] The organic light-emitting device containing the amine compound of the present invention can have a low driving voltage, high luminance, high efficiency and long life. [Brief explanation of the drawings]

[0009] [Figure 1] 1 is a diagram schematically illustrating a structure of an organic light emitting device according to an embodiment. [Figure 2] 1 is a diagram schematically illustrating a structure of an organic light emitting device according to an embodiment. [Figure 3] 1 is a diagram schematically illustrating a structure of an organic light emitting device according to an embodiment. [Figure 4] 1 is a diagram schematically illustrating a structure of an organic light emitting device according to an embodiment. DETAILED DESCRIPTION OF THE INVENTION

[0010] The amine compound of the present invention is represented by the following chemical formula 1: [Chemical formula 1] [ka]

[0011] In Chemical Formula 1, L1 to L4 and L 11 ~L 12 are, independently of each other, substituted or unsubstituted C5-C 60 Carbocyclic groups or substituted or unsubstituted C1-C 60 It is a heterocyclic group.

[0012] According to one embodiment, L1 to L4 and L 11 ~L 12are, independently of one another, phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthylene, fluorenylene, spiro-bifluorenylene, spiro-fluorene-benzofluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, coronenylene, ovalenylene group and carbazolylene; and

[0013] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenylyl group, terphenylyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthyl group, anthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group , pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolylene group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, -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 32a ring structure selected from the group consisting of phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthylene, fluorenylene, spiro-bifluorenylene, spiro-fluorene-benzofluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, coronenylene, ovalenylene, and carbazolylene, substituted with at least one selected from the group consisting of

[0014] Q 31 ~Q 33 are independent of each other, C1-C 10 Alkyl groups, C1-C 10 Alkoxy group, phenyl group, C1-C 10 It may be selected from alkyl-substituted phenyl groups, biphenylyl groups, terphenylyl groups, and naphthyl groups.

[0015] For example, L1 to L4 and L 11 ~L 12 may be independently selected from groups represented by the following chemical formulas 3-1 to 3-27: [ka] [ka] [ka]

[0016] Chemical formulas 3-1 to 3-27: Y 11 is selected from C(Z3)(Z4), N(Z5), Si(Z6)(Z7), O and S; Z1 to Z7 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclopentenyl groups, cyclohexenyl groups, phenyl groups, biphenylyl groups, terphenylyl groups, naphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, pyrenyl groups, chrysenyl groups, pyrrolyl groups, thiophenyl groups, furanyl groups, silolyl groups, imidazolyl groups, pyrazolyl groups, thiazolyl groups, isothiazolyl groups, oxazolyl groups, isoxazolyl groups, pyridinyl groups, pyrazinyl groups, pyrimidinyl groups, pyridazinyl groups, benzofuranyl groups, benzothiophenyl groups, benzosilolyl groups, dibenzosilolyl groups, and -Si(Q 31 )(Q 32 )(Q 33 ), Q 31 ~Q 33 are independent of each other, C1-C 20 Alkyl groups, C1-C 20 selected from the group consisting of alkoxy, phenyl, biphenylyl, terphenylyl, naphthyl and pyridinyl; d2 is an integer from 0 to 2, d3 is an integer from 0 to 3, d4 is an integer from 0 to 4, d6 is an integer from 0 to 6, d8 is an integer from 0 to 8, * and *' are bonding sites with adjacent atoms.

[0017] In Chemical Formula 1, a1 to a4, a11, and a12 are each independently an integer selected from 0 to 5.

[0018] According to one embodiment, a11 and a12 may be 0.

[0019] According to one embodiment, a1 to a4 may be integers selected from the integers 0 to 3, independently of one another.

[0020] For example, a1 to a4 may be integers selected from the integers 0 to 2, independently of one another.

[0021] In Formula 1, Ar1 to Ar4 are each independently a substituted or unsubstituted C5-C 60 Carbocyclic groups or substituted or unsubstituted C1-C 60 It is a heterocyclic group, provided that if two or more of Ar1 to Ar4 contain an amino group, it is excluded.

[0022] According to one embodiment, Ar1 to Ar4 are, independently of one another, Phenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, spiro-fluorene-benzofluorenyl group, benzofluorenyl group, dibenzofluorenyl group, benzonaphthofluorenyl group, pyrenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrrolyl group, thiophenyl group, furanyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group , isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrimidyl, quinolinyl, isoquinolinyl, benzoquinolinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, biphenylyl, and terphenylyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, C1-C 20Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, spiro-fluorene-benzofluorenyl group, benzofluorenyl group, dibenzofluorenyl group, benzonaphthofluorenyl group, pyrenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrrolyl group, thiophenyl group, furanyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, iso Thiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, isoindolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, isobenzothiazolyl group, benzoxa azolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, oxazolopyridinyl group, thiazolopyridinyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzyl group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a spiro-fluorene-benzofluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a benzonaphthofluorenyl group, a pyrenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, or an isothiazolyl group, each of which is substituted with at least one group selected from the group consisting of a silolyl group, a biphenylyl group, and a terphenylyl group;oxazolyl group, isoxazolyl group, pyridinyl group, pyrimidyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, biphenylyl group and terphenylyl group.

[0023] For example, Ar1 to Ar4 may each independently be a group represented by any one selected from the following Chemical Formula 5-1 to Chemical Formula 5-27: [ka] [ka]

[0024] Chemical formulas 5-1 to 5-27: Y 31 is O, S, C(Z 35 )(Z 36 ) or Si(Z 37 )(Z 38 ) and Z 31 ~Z 38 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20Alkoxy group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, anthracenyl group, phenanthrenyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxa a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, or an azacarbazolyl group; e3 is an integer from 0 to 3, e4 is an integer from 0 to 4, e5 is an integer between 0 and 5, e6 is an integer from 0 to 6, e7 is an integer from 0 to 7, e9 is an integer from 0 to 9, * indicates a bonding site with an adjacent atom.

[0025] According to one embodiment, Ar1 to Ar4 do not contain an amino group.

[0026] In formula 1, R1 to R3 are hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, or a substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 Alkenyl groups, substituted or unsubstituted C2-C 60 Alkynyl groups, substituted or unsubstituted C1-C 60 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C6-C 60 Aryloxy groups, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), or -P(=O)(Q1)(Q2); D1 to D3 are deuterium atoms.

[0027] According to one embodiment, R1 to R3 are, independently of one another, Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, methyl group, ethyl group, propyl group, isobutyl group, sec-butyl group, tert-butyl group, C1-C 20 Alkoxy groups, cyclopentyl groups, cyclohexyl groups, phenyl groups, naphthyl groups, fluorenyl groups, carbazolyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, biphenylyl groups, and terphenylyl groups; and a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a ter-butyl group, a C1-C6 substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a ter-butyl group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenylyl group, and a terphenylyl group; 20alkoxy groups, cyclopentyl groups, cyclohexyl groups, phenyl groups, naphthyl groups, fluorenyl groups, carbazolyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, biphenylyl groups and terphenylyl groups.

[0028] For example, at least one of R1 to R3 may be hydrogen.

[0029] For example, R1 to R3 may be hydrogen.

[0030] In Chemical Formula 1, b1 to b3 and c1 to c3 are each independently an integer selected from 0 to 4; However, b1+c1, b2+c2, and b3+c3 are each 4, However, c1+c2+c3 is 1 or greater.

[0031] According to one embodiment, one of c1 to c3 is 4 and the remaining two are 0, or Two of c1 to c3 are 4 and the remaining one is 0, or c1 to c3 may be 4.

[0032] For example, c1 may be 4, and c2 and c3 may be 0. For example, c2 may be 4, and c1 and c3 may be 0. For example, c3 may be 4, and c1 and c2 may be 0. For example, c1 and c2 may be 4, and c3 may be 0. For example, c1 and c3 may be 4, and c2 may be 0. For example, c2 and c3 may be 4, and c1 may be 0. For example, c1, c2, and c3 may be 4.

[0033] According to other embodiments, c1+c2+c3 may be greater than or equal to two.

[0034] For example, c1+c2+c3 may be equal to or greater than 3. For example, c1+c2+c3 may be equal to or greater than 4. For example, c1+c2+c3 may be 4, 8, or 12.

[0035] JPEG0007797120000008.jpg44154 [Chemical formula 2-1] [ka] [Chemical formula 2-2] [ka] [Chemical formula 2-3] [ka] [Chemical formula 2-4] [ka] [Chemical formula 2-5] [ka] [Chemical formula 2-6] [ka] Chemical formula 2-1 to chemical formula 2-6 For the explanation of R1 to R3, D1 to D3, b1 to b3, and c1 to c3, please refer to the above. * and *' are bonding sites with adjacent atoms.

[0036] JPEG0007797120000015.jpg47156

[0037] For example, the amine compound represented by Chemical Formula 1 can also be represented by the following Chemical Formula 10: [Chemical formula 10] [ka] In chemical formula 10, For the explanation of L1 to L4, a1 to a4, Ar1 to Ar4, R1 to R3, D1 to D3, b1 to b3, and c1 to c3, please refer to the above.

[0038] According to one embodiment, the amine compound represented by Chemical Formula 1 may contain four or more deuterium atoms.

[0039] According to one embodiment, the amine compound may be selected from Compounds 1 to 192 below: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0040] The amine compound has a structure represented by Chemical Formula 1. In particular, it contains two amino groups. Due to such a structure, the amine compound has a flat structure, is easy to stack, and can exhibit a low refractive index effect.

[0041] Furthermore, when the amine compound contains three or more phenylene groups in the linker between the amino groups, the glass transition temperature increases, and the thermal stability increases.

[0042] Furthermore, by selectively linking an amino group to three or more phenylene group linkers at the para position of an amine compound, intermolecular interactions are reduced, the glass transition temperature is increased, the synthesis yield is improved, and high efficiency can be achieved.

[0043] Furthermore, the amine compound can exhibit a long life by containing one or more (optionally, four or more) deuterium atoms in the linker between the amino groups.

[0044] Furthermore, the amine compound does not contain two or more amino groups among the amino group substituents, and therefore the energy level within the element is matched, and the amine compound has an energy level suitable for the element in which it is used.

[0045] Therefore, an electronic device, for example, an organic light emitting device, employing the amine compound represented by Chemical Formula 1 can have a low driving voltage, high brightness, high efficiency, and long life.

[0046] Those skilled in the art will be able to understand how to synthesize the amine compound represented by Chemical Formula 1 by referring to the embodiments described below.

[0047] At least one of the amine compounds represented by Chemical Formula 1 may be used between a pair of electrodes of an organic light-emitting device. For example, the amine compound may be contained in at least one of a hole transport region and an emitting layer. Alternatively, the amine compound represented by Chemical Formula 1 may be used as a capping layer material located outside a pair of electrodes of an organic light-emitting device.

[0048] Therefore, there is provided an organic light-emitting device comprising a first electrode, a second electrode facing the first electrode, and an organic layer disposed between the first electrode and the second electrode and including a light-emitting layer, the organic layer comprising one or more amine compounds represented by Chemical Formula 1.

[0049] For example, the organic layer may include one or more amine compounds represented by Chemical Formula 1.

[0050] In this specification, the phrase "(the organic layer) contains one or more amine compounds" can also be interpreted as "(the organic layer) may contain one amine compound belonging to the category of Chemical Formula 1, or two or more different amine compounds belonging to the category of Chemical Formula 1."

[0051] For example, the organic layer may contain only Compound 1 as the amine compound. In this case, Compound 1 may be present in the light-emitting layer of the organic light-emitting device. Alternatively, the organic layer may contain Compound 1 and Compound 2 as the amine compounds. In this case, Compound 1 and Compound 2 may be present in the same layer (e.g., Compound 1 and Compound 2 may both be present in the light-emitting layer) or in different layers (e.g., Compound 1 may be present in the light-emitting layer and Compound 2 may be present in the electron-transporting layer).

[0052] According to one embodiment, The first electrode of the organic light-emitting device is an anode, The second electrode of the organic light-emitting device is a cathode, the organic layer of the organic light-emitting device further includes a hole transport region disposed between the first electrode and the light-emitting layer, and an electron transport region disposed between the light-emitting layer and the second electrode; the hole transport region includes at least one layer selected from a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, and an electron blocking layer; The electron transport region may include at least one layer selected from a buffer layer, a hole blocking layer, an electron modulating layer, an electron transport layer, and an electron injection layer.

[0053] According to one embodiment, the hole transport region may include an amine compound represented by Chemical Formula 1:

[0054] According to one embodiment, the hole transport region comprises a hole transport layer, and the hole transport layer may comprise an amine compound.

[0055] According to one embodiment, the hole transport region comprises a first hole transport layer disposed between the first electrode and the light-emitting layer, and a second hole transport layer disposed between the first hole transport layer and the light-emitting layer; The first hole transport layer may contain an amine compound.

[0056] According to another embodiment, the hole transport region includes a first hole transport layer disposed between the first electrode and the light-emitting layer, and a second hole transport layer disposed between the first hole transport layer and the light-emitting layer; The second hole transport layer may contain an amine compound.

[0057] According to one embodiment, the light-emitting layer comprises a host and a dopant, which may be a fluorescent dopant or a phosphorescent dopant.

[0058] According to one embodiment, the electron transport region may comprise an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0059] In this specification, the term "organic layer" refers to any single and / or multiple layers disposed between a first electrode and a second electrode in an organic light-emitting device. The materials contained in the "organic layer" are not limited to organic materials.

[0060] [Explanation regarding Figure 1] 1 is a schematic cross-sectional view of an organic light emitting device 10 according to one embodiment of the present invention. The organic light emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.

[0061] Hereinafter, the structure and manufacturing method of an organic light emitting device 10 according to an embodiment of the present invention will be described with reference to FIG.

[0062] [First electrode 110] 1, a substrate may be additionally disposed below the first electrode 110 or above the second electrode 190. As the substrate, a glass substrate or a plastic substrate, which has excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness, may be used.

[0063] The first electrode 110 may be formed by providing a first electrode material on the substrate using, for example, a deposition method or a sputtering method. When the first electrode 110 is an anode, the first electrode material may be selected from materials having a high work function to facilitate hole injection.

[0064] The first electrode 110 may be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. To form the first electrode 110 as a transmissive electrode, the first electrode material may be selected from, but is not limited to, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO), zinc oxide (ZnO), and any combination thereof. Alternatively, to form the first electrode 110 as a semi-transparent electrode or a reflective electrode, the first electrode material may be selected from, but is not limited to, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof.

[0065] The first electrode 110 may have a single-layer structure or a multi-layer structure including multiple layers, for example, but not limited to, a three-layer structure of ITO / Ag / ITO.

[0066] [Organic layer 150] The organic layer 150 is disposed on the first electrode 110. The organic layer 150 includes a light-emitting layer.

[0067] The organic layer 150 may further include a hole transport region disposed between the first electrode 110 and the light-emitting layer, and an electron transport region disposed between the light-emitting layer and the second electrode 190.

[0068] [Hole transport region in organic layer 150] The hole transport region may have i) a single layer structure consisting of a single layer made of a single material, ii) a single layer structure consisting of single layers made of multiple different materials, or iii) a multilayer structure having multiple layers made of multiple different materials.

[0069] The hole transport region may include at least one layer selected from a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, and an electron blocking layer.

[0070] For example, the hole transport region may have a single layer structure consisting of a plurality of single layers made of different materials, or may have a multilayer structure of a hole injection layer / hole transport layer, a hole injection layer / hole transport layer / light emitting auxiliary layer, a hole injection layer / light emitting auxiliary layer, a hole transport layer / light emitting auxiliary layer, or a hole injection layer / hole transport layer / electron blocking layer, which are stacked in this order from the first electrode 110, but is not limited to these.

[0071] The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by the following formula 201, and a compound represented by the following formula 202: [ka] [ka] [Chemical formula 201] [ka] [Chemical formula 201] [ka]

[0072] In chemical formula 201 and chemical formula 202, L 201 ~L 204 are, independently of each other, substituted or unsubstituted C3-C 10 Cycloalkylene groups, substituted or unsubstituted C1-C 10 Heterocycloalkylene groups, substituted or unsubstituted C3-C 10 Cycloalkenylene groups, substituted or unsubstituted C1-C 10 Heterocycloalkenylene group, substituted or unsubstituted C6-C 60 Arylene groups, substituted or unsubstituted C1-C 60 selected from the group consisting of heteroarylene groups, substituted or unsubstituted divalent non-aromatic fused polycyclic groups, and substituted or unsubstituted divalent non-aromatic fused polycyclic heterocyclic groups; L 205 *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C1-C 20 Alkylene groups, substituted or unsubstituted C2-C 20 Alkenylene group, substituted or unsubstituted C3-C 10 Cycloalkylene groups, substituted or unsubstituted C1-C 10 Heterocycloalkylene groups, substituted or unsubstituted C3-C 10 Cycloalkenylene groups, substituted or unsubstituted C1-C 10 Heterocycloalkenylene group, substituted or unsubstituted C6-C 60 Arylene groups, substituted or unsubstituted C1-C 60selected from the group consisting of heteroarylene groups, substituted or unsubstituted divalent non-aromatic fused polycyclic groups, and substituted or unsubstituted divalent non-aromatic fused polycyclic heterocyclic groups; xa1 to xa4 are each independently selected from integers of 0 to 3; xa5 is selected from integers from 1 to 10; R 201 ~R 204 , and Q 201 are, independently of each other, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C6-C 60 Aryloxy groups, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 It may be selected from among a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused polycyclic heterocyclic group.

[0073] For example, in formula 202, R 201 and R 202 may alternatively be linked to each other via a single bond, a dimethyl-methylene group or a diphenyl-methylene group, and R 203 and R 204 may alternatively be linked to each other via a single bond, a dimethyl-methylene group or a diphenyl-methylene group.

[0074] According to one embodiment, in Formula 201 and Formula 202: L 201 ~L 205 are independent of each other, a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, perylenylene groups, pentaphenylene groups, hexacenylene groups, pentacenylene groups, rubicenylene groups, coronenylene groups, ovalenylene groups, thiophenylene groups, furanylene groups, carbazolylene groups, indolylene groups, isoindolylene groups, benzofuranylene groups, benzothiophenylene groups, dibenzofuranylene groups, dibenzothiophenylene groups, benzocarbazolylene groups, dibenzocarbazolylene groups, dibenzosilolylene groups, and pyridinylene groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenylyl group, terphenylyl group, C1-C 10 Phenyl groups substituted with alkyl groups, phenyl groups substituted with -F, pentalenyl groups, indenyl groups, naphthyl groups, azulenyl groups, heptalenyl groups, indacenyl groups, acenaphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenalenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, triphenylenyl groups, pyrenyl groups, chrysenyl groups, naphthyl groups, Tacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, -Si(Q 31 )(Q32 )(Q 33 ), and -N(Q 31 )(Q 32 a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, or a naphthacenylene group, each of which is substituted with at least one selected from the group consisting of groups, picenylene groups, perylenylene groups, pentaphenylene groups, hexacenylene groups, pentacenylene groups, rubicenylene groups, coronenylene groups, ovalenylene groups, thiophenylene groups, furanylene groups, carbazolylene groups, indolylene groups, isoindolylene groups, benzofuranylene groups, benzothiophenylene groups, dibenzofuranylene groups, dibenzothiophenylene groups, benzocarbazolylene groups, dibenzocarbazolylene groups, dibenzosilolylene groups, and pyridinylene groups; Q 31 ~Q 33 are independent of each other, C1-C 10 Alkyl groups, C1-C 10 It may be selected from the group consisting of alkoxy, phenyl, biphenylyl, terphenylyl and naphthyl groups.

[0075] According to other embodiments, xa1 to xa4 may be 0, 1 or 2, independently of each other.

[0076] According to yet other embodiments, xa5 may be 1, 2, 3 or 4.

[0077] According to yet another embodiment, R 201 ~R 204 , and Q 201are each independently a phenyl group, a biphenylyl group, a terphenylyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthalenyl group, phthalocenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, and pyridinyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenylyl group, terphenylyl group, C1-C 10 Phenyl groups substituted with alkyl groups, phenyl groups substituted with -F, pentalenyl groups, indenyl groups, naphthyl groups, azulenyl groups, heptalenyl groups, indacenyl groups, acenaphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenalenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, triphenylenyl groups, pyrenyl groups, chrysenyl groups, naphthyl groups, Tacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, -Si(Q 31 )(Q 32 )(Q33 ), and -N(Q 31 )(Q 32 a phenyl group, a biphenylyl group, a terphenylyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, or a chrysenyl group, each of which is substituted with at least one selected from the group consisting of , naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, and pyridinyl groups; Q 31 ~Q 33 For the relevant explanation, please refer to the description in this specification.

[0078] According to yet another embodiment, in formula 201, R 201 ~R 203 At least one of the fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenylyl group, terphenylyl group, C1-C 10The alkyl group may be selected from the group consisting of phenyl groups substituted with alkyl groups, phenyl groups substituted with -F, naphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, carbazolyl groups, dibenzofuranyl groups, and dibenzothiophenyl groups, each substituted with at least one selected from the group consisting of naphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, carbazolyl groups, dibenzofuranyl groups, and dibenzothiophenyl groups, but is not limited thereto.

[0079] According to yet another embodiment, in Formula 202, i) R 201 and R 202 are also linked to each other via a single bond, and / or ii) R 203 and R 204 may be linked to each other via a single bond.

[0080] According to yet another embodiment, in formula 202, R 201 ~R 204 At least one of the a carbazolyl group; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenylyl group, terphenylyl group, C1-C 10 The alkyl group may be selected from the group consisting of a phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a carbazolyl group substituted with at least one selected from a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, but is not limited thereto.

[0081] The compound of formula 201 may be represented by formula 201-1: [Chemical formula 201-1] [ka]

[0082] For example, the compound represented by formula 201 may be represented by, but is not limited to, formula 201-2: [Chemical formula 201-2] [ka]

[0083] As yet another example, the compound represented by formula 201 may be represented by, but is not limited to, the following formula 201-2(1): [Chemical formula 201-2(1)] [ka]

[0084] The compound of formula 201 may be represented by formula 201A: [Chemical formula 201A] [ka]

[0085] For example, the compound represented by formula 201 may also be represented by the following formula 201A(1), but is not limited thereto: [Chemical formula 201A(1)] [ka]

[0086] As yet another example, the compound represented by formula 201 may be represented by, but is not limited to, the following formula 201A-1: [Chemical formula 201A-1] [ka]

[0087] According to one embodiment, the compound represented by formula 202 may be represented by formula 202-1: [Chemical formula 202-1] [ka]

[0088] According to yet another embodiment, the compound represented by formula 202 may be represented by the following formula 202-1(1): [Chemical formula 202-1(1)] [ka]

[0089] Alternatively, the compound represented by formula 202 may be represented by the following formula 202A: [Chemical formula 202A] [ka]

[0090] According to yet another embodiment, the compound represented by formula 202 may be represented by formula 202A-1: [Chemical formula 202A-1] [ka]

[0091] Chemical formula 201-1, chemical formula 201-2, chemical formula 201-2(1), chemical formula 201A, chemical formula 201A(1), chemical formula 201A-1, chemical formula 202-1, chemical formula 202-1(1), chemical formula 202A and chemical formula 202A-1, L 201 ~L 203 , xa1 to xa3, xa5, and R 202 ~R 204 For a description of the above, please refer to the description in this specification. L 205 is selected from the group consisting of phenylene and fluorenylene groups; X211 is O, S and N(R 211 ), X 212 is O, S and N(R 212 ), R 211 and R 212 The explanation regarding R 203 Please refer to the explanation regarding R 213 ~R 217 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenylyl group, terphenylyl group, C1-C 10 Phenyl groups substituted with alkyl groups, phenyl groups substituted with -F, pentalenyl groups, indenyl groups, naphthyl groups, azulenyl groups, heptalenyl groups, indacenyl groups, acenaphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenalenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, triphenylenyl groups, pyrenyl groups, chrysenyl groups, and naphthacenyl groups , picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, and pyridinyl group.

[0092] The hole transport region may include at least one compound selected from the following compounds HT1 to HT48, but is not limited thereto: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0093] The thickness of the hole transport region may be about 10 nm to about 1,000 nm, for example, about 10 nm to about 100 nm. When the hole transport region includes at least one layer selected from a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be about 10 nm to about 900 nm, for example, about 10 nm to about 100 nm, and the thickness of the hole transport layer may be about 5 nm to about 200 nm, for example, about 10 nm to about 150 nm. When the thicknesses of the hole transport region, hole injection layer, and hole transport layer satisfy the above-mentioned ranges, satisfactory hole transport properties can be obtained without a substantial increase in driving voltage.

[0094] The light-emitting auxiliary layer compensates for the optical resonance distance depending on the wavelength of light emitted from the light-emitting layer, thereby increasing light emission efficiency, and the electron-blocking layer prevents electron injection from the electron-transporting region. The light-emitting auxiliary layer and the electron-blocking layer may contain the materials described above.

[0095] [p-dopant] In addition to the materials described above, the hole transport region may further include a charge generating material to improve conductivity. The charge generating material may be uniformly or non-uniformly dispersed within the hole transport region.

[0096] The charge generating material can be, for example, a p-dopant.

[0097] According to one embodiment, the LUMO (lowest unoccupied molecular orbital) of the p-dopant may be less than or equal to -3.5 eV.

[0098] The p-dopant may include at least one selected from the group consisting of quinone derivatives, metal oxides, and cyano group-containing compounds, but is not limited thereto.

[0099] For example, the p dopant quinone derivatives such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ); metal oxides such as tungsten oxide and molybdenum oxide; 1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and The compound may include, but is not limited to, at least one selected from the following compounds represented by the following chemical formula 221: <hat-cn>

change

[0100] [Light-emitting layer in organic layer 150] When the organic light emitting device 10 is a full-color organic light emitting device, the light emitting layer may be patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer for each individual subpixel. Alternatively, the light emitting layer may have a structure in which two or more layers selected from the red light emitting layer, the green light emitting layer, and the blue light emitting layer are stacked in contact with or spaced apart from each other, or a structure in which two or more materials selected from the red light emitting material, the green light emitting material, and the blue light emitting material are mixed without layer division, thereby emitting white light.

[0101] The light-emitting layer may include a host and a light-emitting material, and the light-emitting material may include at least one of a phosphorescent dopant, a fluorescent dopant, and a quantum dot.

[0102] In the light-emitting layer, the content of the dopant may generally be selected from the range of about 0.01 parts by weight to about 15 parts by weight relative to about 100 parts by weight of the host, but is not limited thereto.

[0103] The thickness of the light-emitting layer may be about 10 nm to about 100 nm, for example, about 20 nm to about 60 nm. When the thickness of the light-emitting layer satisfies the above-mentioned range, excellent light-emitting characteristics can be exhibited without a substantial increase in driving voltage.

[0104] [Host in the light-emitting layer] The host may include the amine compound represented by Chemical Formula 1 above.

[0105] The host may further include a compound represented by the following formula: [Chemical formula 301] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 In chemical formula 301, Ar 301 is a substituted or unsubstituted C5-C 60 Carbocyclic or substituted or unsubstituted C1-C 60 is a heterocycle, xb11 is 1, 2 or 3; L 301 is a substituted or unsubstituted C3-C 10 Cycloalkylene groups, substituted or unsubstituted C1-C 10 Heterocycloalkylene groups, substituted or unsubstituted C3-C 10 Cycloalkenylene groups, substituted or unsubstituted C1-C 10 Heterocycloalkenylene group, substituted or unsubstituted C6-C 60 Arylene groups, substituted or unsubstituted C1-C 60 selected from the group consisting of heteroarylene groups, substituted or unsubstituted divalent non-aromatic fused polycyclic groups, and substituted or unsubstituted divalent non-aromatic fused polycyclic heterocyclic groups; xb1 is selected from integers from 0 to 5; R 301 is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 Alkenyl groups, substituted or unsubstituted C2-C 60 Alkynyl groups, substituted or unsubstituted C1-C 60 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C6-C 60 Aryloxy groups, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic groups, -Si(Q 301 )(Q 302 )(Q 303 ), -N(Q 301 )(Q 302 ), -B(Q 301 )(Q 302 ), -C(=O)(Q 301 ), -S(=O)2(Q 301 ), and -P(=O)(Q 301 )(Q 302 ), xb21 is selected from integers from 1 to 5; Q 301 ~Q 303 are independent of each other, C1-C 10 Alkyl groups, C1-C 10 It may be selected from, but is not limited to, an alkoxy group, a phenyl group, a biphenylyl group, a terphenylyl group, and a naphthyl group.

[0106] According to one embodiment, in formula 301, Ar 301 teeth, naphthalene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, indenoanthracene, dibenzofuran and dibenzothiophene; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, -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 naphthalene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, indenoanthracene, dibenzofuran, and dibenzothiophene; Q 31 ~Q 33 are independent of each other, C1-C 10 Alkyl groups, C1-C 10 It may be selected from, but is not limited to, an alkoxy group, a phenyl group, a biphenylyl group, a terphenylyl group, and a naphthyl group.

[0107] In chemical formula 301, if xb11 is 2 or more, 2 or more Ar 301 may be linked to each other via a single bond.

[0108] According to other embodiments, the compound represented by formula 301 may be represented by formula 301-1 or formula 301-2: [Chemical formula 301-1] [ka] [Chemical formula 301-2] [ka] Chemical formula 301-1 to chemical formula 301-2, A 301 ~A 304 are, independently of one another, ring structures selected from benzene, naphthalene, phenanthrene, fluoranthene, triphenylene, pyrene, chrysene, pyridine, pyrimidine, indene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, indole, carbazole, benzocarbazole, dibenzocarbazole, furan, benzofuran, dibenzofuran, naphthofuran, benzonaphthofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthothiophene, benzonaphthothiophene and dinaphthothiophene, X 301 is O, S or N-[(L 304 ) xb4 -R 304 ] and R 311 ~R 314 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, -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 ), xb22 and xb23 are independently 0, 1 or 2; L 301 , xb1, R 301 , and Q 31 ~Q 33 For a description of the above, please refer to the description in this specification. L 302 ~L 304 The explanations for L 301 Please refer to the explanation regarding The explanations for xb2 to xb4 are independent of each other and refer to the explanation for xb1. R 302 ~R 304 The explanations for R 301 Please refer to the explanation related to this.

[0109] For example, in formula 301, formula 301-1, and formula 301-2, L 301 ~L 304 are independent of each other, Phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindolylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylene group, imidazolylene group, pyrazolylene group, thiazolylene groups, isothiazolylene groups, oxazolylene groups, isoxazolylene groups, thiadiazolylene groups, oxadiazolylene groups, pyrazinylene groups, pyrimidinylene groups, pyridazinylene groups, triazinylene groups, quinolinylene groups, isoquinolinylene groups, benzoquinolinylene groups, phthalazinylene groups, naphthyridinylene groups, quinoxalinylene groups, quinazolinylene groups, cinnolinylene groups, phenanthridinylene groups, acridinylene groups, phenanthrolinylene groups, phenazinylene groups, benzimidazolylene groups, isobenzothiazolylene groups, benzoxazolylene groups, benzisoxazolylene groups, triazolylene groups, tetrazolylene groups, imidazopyridinylene groups, imidazopyrimidinylene groups, and azacarbazolylene groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl ... azolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, -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 a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, a benzisoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group; Q 31 ~Q 33 For the explanation of this, please refer to the description in this specification.

[0110] As another example, in Formula 301, Formula 301-1, and Formula 301-2, R 301 ~R 304 are independent of each other, Phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazolyl group , thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazo a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, -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 a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group; Q 31 ~Q 33 For the explanation of this, please refer to the description in this specification.

[0111] As yet another example, the host may include an alkaline earth metal complex, for example, the host may be selected from the group consisting of a Be complex (e.g., compound H55 below), a Mg complex, and a Zn complex.

[0112] The host may include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthylene-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and the following compounds H1 to H55, but is not limited thereto: [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0113] [Phosphorescent dopant included in the light-emitting layer of organic layer 150] The phosphorescent dopant may include an organometallic complex represented by formula 401: [Chemical formula 401] M(L 401 ) xc1 (L 402 ) xc2 [Chemical formula 402] [ka] In chemical formulas 401 and 402, M is selected from the group consisting of iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), and thulium (Tm); L 401 is selected from the ligands represented by chemical formula 402, xc1 is 1, 2 or 3, and when xc1 is 2 or more, two or more L 401 are identical to or different from each other, L 402 is an organic ligand, xc2 is selected from integers of 0 to 4, and when xc2 is 2 or more, two or more L 402 are identical to or different from each other, X 401 ~X 404 are, independently of each other, nitrogen or carbon; X 401 and X 403 are linked via a single or double bond, and X 402 and X 404 is linked via a single or double bond, A 401 and A 402 are independent of each other, C5-C 60 Carbocyclic group or C1-C 60 is a heterocyclic group, X 405 is 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=*', and Q 411 and Q 412 are hydrogen, deuterium, C1-C 20 Alkyl groups, C1-C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group; X 406 is a single bond, O or S, R 401 and R 402 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C 20 Alkyl groups, substituted or unsubstituted C1-C 20 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C6-C 60 Aryloxy groups, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, and substituted or unsubstituted monovalent non-aromatic fused polycyclic heterocyclic groups, -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 Q 401 ~Q 403 are independent of each other, C1-C 10 Alkyl groups, C1-C 10 Alkoxy groups, C6-C 20 Aryl groups and C1-C 20 heteroaryl groups, xc11 and xc12 are each independently selected from integers of 0 to 10; In chemical formula 402, * and *' are bonding sites with M in chemical formula 401.

[0114] According to one embodiment, in formula 402, A 401 and A 402 may each independently be a ring structure selected from benzene, naphthalene, fluorene, spiro-bifluorene, indene, pyrrole, thiophene, furan, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, quinoline, isoquinoline, benzoquinoline, quinoxaline, quinazoline, carbazole, benzimidazole, benzofuran, benzothiophene, isobenzothiophene, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran, and dibenzothiophene.

[0115] According to another embodiment, in formula 402, i) X 401 is nitrogen and X 402 is carbon, or ii) X 401 and X 402 and may both be nitrogen.

[0116] According to yet another embodiment, in formula 402, R 401 and R 402 are independent of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups and C1-C 20 Alkoxy groups; C1-C substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a phenyl group, a naphthyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornanyl group, and a norbornenyl group; 20 Alkyl groups and C1-C 20 Alkoxy groups; cyclopentyl group, cyclohexyl group, adamantyl group, norbornanyl group, norbornenyl group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 selected from the group consisting of an alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group cyclopentyl, cyclohexyl, adamantyl, norbornanyl, norbornenyl, phenyl, biphenylyl, terphenylyl, naphthyl, fluorenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl groups, each substituted with at least one of the following: -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 ); Q 401 ~Q 403 are independent of each other, C1-C 10 Alkyl groups, C1-C 10 It may be selected from, but is not limited to, an alkoxy group, a phenyl group, a biphenylyl group, and a naphthyl group.

[0117] According to yet another embodiment, in formula 401, when xc1 is 2 or more, two or more L 401 Two of the A 401 optionally, a linking group, X 407 or two A 402 optionally, a linking group, X 408 (See compounds PD1 to PD4 and PD7 below.) 407 and X 408 are, independently of each other, 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 Q 414 may be, independently of each other, hydrogen, deuterium, a phenyl group, a biphenylyl group, a terphenyl group, or a naphthyl group, but are not limited thereto.

[0118] In chemical formula 401, L 402 may be any monovalent, divalent, or trivalent organic ligand. For example, L 402 may be selected from, but is not limited to, halogen, diketone (e.g., acetylacetonate), carboxylic acid (e.g., picolinate), —C(═O), isonitrile, —CN, and phosphorus (e.g., phosphine, phosphite).

[0119] Alternatively, the phosphorescent dopant may be selected from, for example, but not limited to, the following compounds PD1 to PD25: [ka] [ka] [ka]

[0120] [Fluorescent dopants in the light-emitting layer] The fluorescent dopant may include an amine compound represented by Chemical Formula 1 above.

[0121] Alternatively, the fluorescent dopant may include an arylamine compound or a styrylamine compound.

[0122] The fluorescent dopant may include a compound represented by formula 501: [Chemical formula 501] [ka] In chemical formula 501, Ar 501 is a substituted or unsubstituted C5-C 60 Carbocyclic or substituted or unsubstituted C1-C 60 is a heterocycle, L 501 ~L 503 are, independently of each other, substituted or unsubstituted C3-C 10 Cycloalkylene groups, substituted or unsubstituted C1-C 10 Heterocycloalkylene groups, substituted or unsubstituted C3-C 10 Cycloalkenylene groups, substituted or unsubstituted C1-C 10 Heterocycloalkenylene group, substituted or unsubstituted C6-C 60 selected from an arylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, and a substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group; xd1 to xd3 are independently selected from integers of 0 to 3; R 501 and R 502 are, independently of each other, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C6-C 60 Aryloxy groups, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 is selected from the group consisting of a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused polycyclic heterocyclic group; xd4 may be selected from integers from 1 to 6.

[0123] According to one embodiment, in formula 501, Ar 501 teeth, naphthalene, heptalene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, indenoanthracene and indenophenanthrene; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 The ring structure may be selected from the group consisting of naphthalene, heptalene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, indenoanthracene, and indenophenanthrene, substituted with at least one selected from the group consisting of an alkoxy group, a phenyl group, a biphenylyl group, a terphenylyl group, and a naphthyl group.

[0124] According to another embodiment, in formula 501, L 501 ~L 503 are independent of each other, Phenylene groups, naphthylene groups, fluorenylene groups, spiro-bifluorenylene groups, benzofluorenylene groups, dibenzofluorenylene groups, phenanthrenylene groups, anthracenylene groups, fluoranthenylene groups, triphenylenylene groups, pyrenylene groups, chrysenylene groups, perylenylene groups, pentaphenylene groups, hexacenylene groups, pentacenylene groups, thiophenylene groups, furanylene groups, carbazolylene groups, indolylene groups, isoindolylene groups, benzofuranylene groups, benzothiophenylene groups, dibenzofuranylene groups, dibenzothiophenylene groups, benzocarbazolylene groups, dibenzocarbazolylene groups, dibenzosilolylene groups, and pyridinylene groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 substituted with at least one selected from an alkoxy group, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group; a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group;

[0125] According to yet another embodiment, in formula 501, R 501 and R 502 are independent of each other, Phenyl, biphenylyl, terphenylyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, and pyridinyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, phenyl groups, biphenylyl groups, terphenylyl groups, naphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, triphenylenyl groups, pyrenyl groups, chrysenyl groups, perylenyl groups, pentaphenyl groups, hexacenyl groups, pentacenyl groups, thiophenyl groups, furanyl groups, carbazolyl groups, indolyl groups, isoindolyl groups, benzofuranyl groups, benzothiophenyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, benzocarbazolyl groups, dibenzocarbazolyl groups, dibenzosilolyl groups, pyridinyl groups, and -Si(Q 31 )(Q 32 )(Q 33 phenyl, biphenylyl, terphenylyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl and pyridinyl groups, Q 31 ~Q 33 is C1-C 10 Alkyl groups, C1-C 10 It may be selected from the group consisting of alkoxy, phenyl, biphenylyl, terphenylyl and naphthyl groups.

[0126] According to yet another embodiment, in formula 501, xd4 may be 2, but is not limited thereto.

[0127] For example, the fluorescent dopant may be selected from the following compounds FD1 to FD22: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0128] Alternatively, the fluorescent dopant may be selected from the following compounds, but is not limited thereto: [ka] [ka]

[0129] [Quantum dots] The light-emitting layer included in the organic light-emitting device of the present invention may include quantum dots.

[0130] Quantum dots are particles with a crystalline structure measuring several nanometers to several tens of nanometers, and are composed of several hundred to several thousand atoms.

[0131] Because quantum dots are so small, they exhibit the quantum confinement effect, which is a phenomenon in which the band gap of an object increases as the object shrinks to nanometer size or smaller. When light with a wavelength greater than the band gap of a quantum dot is irradiated onto the quantum dot, the quantum dot absorbs the light, becomes excited, and then emits light of a specific wavelength before returning to the ground state. The wavelength of the emitted light has a value corresponding to the band gap.

[0132] The core of the quantum dot may comprise a II-VI compound, a III-VI compound, a III-V compound, a IV-VI compound, a group IV element or compound, a I-III-VI compound, or a combination thereof.

[0133] II-VI compounds are binary compounds selected from the group consisting of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof; CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgT ternary compounds selected from the group consisting of CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and mixtures thereof; and quaternary compounds selected from the group consisting of CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and mixtures thereof.

[0134] III-VI compounds may include binary compounds such as In2S3, In2Se3; ternary compounds such as InGaS3, InGaSe3; or any combination thereof.

[0135] The III-V compound may be selected from the group consisting of binary compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; ternary compounds selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, and mixtures thereof; and quaternary compounds selected from the group consisting of GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof. The III-V semiconductor compound may further include a Group II metal (such as, for example, InZnP).

[0136] The IV-VI compound may be selected from the group consisting of binary compounds selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; ternary compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and quaternary compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. The Group IV element may be selected from the group consisting of Si, Ge, and mixtures thereof. The Group IV compound may be a binary compound selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0137] In this case, the two-element compound, three-element compound, or four-element compound may be present in a uniform concentration within the particle, or may be present within the same particle with partially different concentration distributions. The quantum dot may also have a core / shell structure in which one quantum dot surrounds another. The interface between the core and shell may have a concentration gradient in which the concentration of the element present in the shell decreases toward the center.

[0138] In some embodiments, quantum dots can have a core-shell structure, including a core containing the nanocrystals described above and a shell surrounding the core. The shell of the quantum dot can serve as a protective layer to prevent chemical modification of the core and maintain its semiconducting properties, and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient in which the concentration of elements present in the shell decreases toward the center. Examples of quantum dot shells include metal or nonmetal oxides, semiconductor compounds, or combinations thereof.

[0139] For example, examples of metal or non-metal oxides include binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and NiO, and ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, and CoMn2O4, but the present invention is not limited thereto.

[0140] Examples of semiconductor compounds include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, and AlSb, but the present invention is not limited to these.

[0141] The quantum dots can have a full width at half maximum (FWHM) of the emission wavelength spectrum of about 45 nm or less, preferably about 40 nm or less, and more preferably about 30 nm or less, and within this range, color purity and color reproducibility can be improved. Furthermore, light emitted through such quantum dots is emitted in all directions, and the light viewing angle can be improved.

[0142] Furthermore, the shape of the quantum dots is not particularly limited to those commonly used in the art, but more specifically, shapes such as spherical, pyramidal, multi-arm or cubic nanoparticles, nanotubes, nanowires, nanofibers, and nanoplate-like particles can be used.

[0143] The quantum dots can adjust the hue of the light they emit depending on their particle size, and thus can emit a variety of hues, such as blue, red, and green.

[0144] [Electron transport region in organic layer 150] The electron transport region can have i) a single layer structure consisting of a single layer of a single material, ii) a single layer structure consisting of a plurality of single layers of different materials, or iii) a multilayer structure having multiple layers consisting of a plurality of different materials.

[0145] The electron transport region may include at least one layer selected from, but is not limited to, a buffer layer, a hole blocking layer, an electron modulating layer, an electron transport layer, and an electron injection layer.

[0146] For example, the electron transport region may have a structure such as, but not limited to, an electron transport layer / electron injection layer, a hole blocking layer / electron transport layer / electron injection layer, an electron modulation layer / electron transport layer / electron injection layer, or a buffer layer / electron transport layer / electron injection layer, which are stacked in this order from the light emitting layer.

[0147] The electron transport region (eg, a buffer layer, a hole blocking layer, an electron modulating layer, or an electron transport layer in an electron transport region) may include a non-metal-containing compound that includes at least one π-electron deficient nitrogen-containing ring.

[0148] The "π-electron deficient nitrogen-containing ring" is a C1-C ring having at least one *-N=*' moiety as a ring-forming moiety. 60 It means a heterocyclic group.

[0149] For example, the "π-electron deficient nitrogen-containing ring" is i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' moiety, ii) a heteropolycyclic group in which two or more of the 5- to 7-membered heteromonocyclic groups having at least one *-N=*' moiety are fused to each other, or iii) a heteropolycyclic group in which at least one of the 5- to 7-membered heteromonocyclic groups having at least one *-N=*' moiety and at least one C5-C 60 It may also be a heteropolycyclic group in which carbocyclic groups are condensed with each other.

[0150] Specific examples of the π-electron deficient nitrogen-containing ring include, but are not limited to, 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, benzisothiazole, benzoxazole, benzisoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole.

[0151] For example, the electron transport region may include a compound represented by formula 601 below. [Chemical formula 601] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 In chemical formula 601, Ar 601 is a substituted or unsubstituted C5-C 60 Carbocyclic or substituted or unsubstituted C1-C 60 is a heterocycle, xe11 is 1, 2 or 3, L 601 is a substituted or unsubstituted C3-C 10 Cycloalkylene groups, substituted or unsubstituted C1-C 10 Heterocycloalkylene groups, substituted or unsubstituted C3-C 10 Cycloalkenylene groups, substituted or unsubstituted C1-C 10 Heterocycloalkenylene group, substituted or unsubstituted C6-C 60 Arylene groups, substituted or unsubstituted C1-C 60 selected from the group consisting of heteroarylene groups, substituted or unsubstituted divalent non-aromatic fused polycyclic groups, and substituted or unsubstituted divalent non-aromatic fused polycyclic heterocyclic groups; xe1 is selected from integers 0 to 5, R 601 is a substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C6-C 60 Aryloxy groups, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic groups, -Si(Q 601 )(Q 602 )(Q 603 ), -C(=O)(Q 601 ), -S(=O)2(Q 601 ), and -P(=O)(Q 601 )(Q 602 ), Q 601 ~Q 603 are independent of each other, C1-C 10 Alkyl groups, C1-C 10 an alkoxy group, a phenyl group, a biphenylyl group, a terphenylyl group, or a naphthyl group; xe21 is selected from integers from 1 to 5.

[0152] According to one embodiment, xe11 Ar 601 , and xe21 R 601 At least one of the groups may contain a π-electron deficient nitrogen-containing ring as described above.

[0153] According to one embodiment, in formula 601, Ar 601 teeth, benzene, naphthalene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, indenoanthracene, dibenzofuran, dibenzothiophene, carbazole, 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, benzisothiazole, benzoxazole, benzisoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine and azacarbazole; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 benzene, naphthalene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, indenoanthracene, dibenzofuran, dibenzothiophene, carbazole, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine ... a ring structure selected from the group consisting of imidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole, benzisothiazole, benzoxazole, benzisoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole; Q 31 ~Q 33 are independent of each other, C1-C 10 Alkyl groups, C1-C 10 It may be selected from the group consisting of alkoxy, phenyl, biphenylyl, terphenylyl and naphthyl groups.

[0154] In chemical formula 601, if xe11 is 2 or more, 2 or more Ar 601 are also linked to each other via a single bond.

[0155] According to another embodiment, in formula 601, Ar 601 may be anthracene.

[0156] According to yet another embodiment, the compound represented by 601 may also be represented by the following chemical formula 601-1: [Chemical formula 601-1] [ka] Chemical formula 601-1: X 614 is N or C(R 614 ) and X 615 is N or C(R 615 ) and X 616 is N or C(R 616 ) and X 614 ~X 616 At least one of is N, L 611 ~L 613 are, independently of each other, L 601 Please refer to the explanation regarding xe611 to xe613 are independent of each other and refer to the explanation related to xe1. R 611 ~R 613 are, independently of each other, R 601 Please refer to the explanation regarding R 614 ~R 616 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 It may be selected from the group consisting of alkoxy, phenyl, biphenylyl, terphenylyl and naphthyl groups.

[0157] According to one embodiment, in formulas 601 and 601-1, L 601 , and L 611 ~L 613 are independent of each other, Phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindolylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylene group, imidazolylene group, pyrazolylene group, thiazolylene groups, isothiazolylene groups, oxazolylene groups, isoxazolylene groups, thiadiazolylene groups, oxadiazolylene groups, pyrazinylene groups, pyrimidinylene groups, pyridazinylene groups, triazinylene groups, quinolinylene groups, isoquinolinylene groups, benzoquinolinylene groups, phthalazinylene groups, naphthyridinylene groups, quinoxalinylene groups, quinazolinylene groups, cinnolinylene groups, phenanthridinylene groups, acridinylene groups, phenanthrolinylene groups, phenazinylene groups, benzimidazolylene groups, benzisothiazolylene groups, benzoxazolylene groups, benzisoxazolylene groups, triazolylene groups, tetrazolylene groups, imidazopyridinylene groups, imidazopyrimidinylene groups, and azacarbazolylene groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarboxyl group, benzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexa ... a saccenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group,The alkyl group may be selected from, but is not limited to, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, a benzisothiazolylene group, a benzoxazolylene group, a benzisoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group.

[0158] According to other embodiments, in formulas 601 and 601-1, xe1 and xe611 to xe613 may be 0, 1, or 2, independently of each other.

[0159] According to yet another embodiment, in formulas 601 and 601-1, R 601 , and R 611 ~R 613 are independent of each other, Phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazolyl group a thiazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group a zolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptyl group, a phenyl group, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptyl ... an xacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group,benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl groups; and -S(=O)2(Q 601 ) and -P(=O)(Q 601 )(Q 602 ); Q 601 and Q 602 For the relevant explanation, please refer to the description in this specification.

[0160] The electron transport region may include at least one compound selected from the following compounds ET1 to ET36, but is not limited thereto: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0161] Alternatively, the electron transport region may include at least one compound selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ. [ka]

[0162] The thickness of the buffer layer, hole blocking layer, or electron control layer may be, independently of one another, about 2 nm to about 100 nm, for example, about 3 nm to about 30 nm. When the thickness of the buffer layer, hole blocking layer, or electron control layer satisfies the above-mentioned range, excellent hole blocking properties or electron control properties can be obtained without a substantial increase in driving voltage.

[0163] The thickness of the electron transport layer may be about 10 nm to about 100 nm, for example, about 15 nm to about 50 nm. When the thickness of the electron transport layer satisfies the above-mentioned range, satisfactory electron transport properties can be obtained without a substantial increase in driving voltage.

[0164] The electron transport region (for example, the electron transport layer in the electron transport region) may further contain a metal-containing material in addition to the materials described above.

[0165] The metal-containing material may include at least one selected from an alkali metal complex and an alkaline earth metal complex. The metal ion of the alkali metal complex may be selected from Li ion, Na ion, K ion, Rb ion, and Cs ion, and the metal ion of the alkaline earth metal complex may be selected from Be ion, Mg ion, Ca ion, Sr ion, and Ba ion. The ligands coordinated to the metal ions of the alkali metal complex and the alkaline earth metal complex may be independently selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but are not limited thereto.

[0166] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, the following compound ET-D1 (lithium quinolate (LiQ)) or ET-D2. [ka] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.

[0167] The electron injection layer may have i) a single layer structure consisting of a single layer made of a single material, ii) a single layer structure consisting of a plurality of single layers made of different materials, or iii) a multilayer structure having a plurality of layers made of a plurality of different materials.

[0168] The electron injection layer may comprise an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0169] The alkali metal may be selected from the group consisting of Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal may be Li, Na, or Cs. In other embodiments, the alkali metal may be, but is not limited to, Li or Cs.

[0170] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

[0171] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb and Gd.

[0172] 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, iodides, etc.) of alkali metals, alkaline earth metals and rare earth metals.

[0173] The alkali metal compound may be selected from alkali metal oxides such as LiO, CsO, and KO, and alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and KI. According to an embodiment, the alkali metal compound may be selected from, but is not limited to, LiF, LiO, NaF, LiI, NaI, CsI, and KI.

[0174] Alkaline earth metal compounds include BaO, SrO, CaO, and Ba x Sr 1-x O(0 <x<1)、Ba x Ca 1-x It may be selected from alkaline earth metal compounds such as O(0 < x < 1). According to one embodiment, the alkaline earth metal compound may be selected from, but not limited to, BaO, SrO, and CaO.

[0175] The rare earth metal compound may be selected from YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, and TbF3. According to one embodiment, the rare earth metal compound may be selected from, but not limited to, YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3.

[0176] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex contain metal ions of the alkali metal, alkaline earth metal, and rare earth metal as described above, and the ligands coordinated to the metal ions of the alkali metal complex, alkaline earth metal complex, and rare earth metal complex may be independently selected from, but not limited to, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene.

[0177] The electron injection layer may consist solely of the aforementioned 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 any combination thereof, or may further contain an organic substance. When the electron injection layer further contains an organic substance, 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 any combination thereof may be uniformly or non-uniformly dispersed in a matrix composed of the organic substance.

[0178] The thickness of the electron injection layer may be about 0.1 nm to about 10 nm, or about 0.3 nm to about 9 nm. When the thickness of the electron injection layer satisfies the above-mentioned range, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0179] [Second electrode 190] A second electrode 190 is disposed on the organic layer 150. The second electrode 190 may be a cathode, which is an electron injection electrode, and materials for the second electrode 190 may be metals, alloys, electrically conductive compounds, or combinations thereof, each having a low work function.

[0180] The second electrode 190 may include at least one selected from the group consisting of lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), silver-magnesium (Ag-Mg), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, and IZO, but is not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0181] The second electrode 190 may have a single layer structure, which is a single layer, or a multi-layer structure having multiple layers.

[0182] [Explanation regarding Figures 2 to 4] Meanwhile, the organic light emitting device 20 of FIG. 2 has a structure in which a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190 are stacked in this order, the organic light emitting device 30 of FIG. 3 has a structure in which a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 are stacked in this order, and the organic light emitting device 40 of FIG. 4 has a structure in which a first capping layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 are stacked in this order.

[0183] 2 to 4, the description of the first electrode 110, the organic layer 150, and the second electrode 190 refers to the description of FIG.

[0184] In the organic layer 150 of the organic light-emitting element 20 or 40, light generated in the light-emitting layer may be extracted to the outside through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer 210, and in the organic layer 150 of the organic light-emitting element 30 or 40, light generated in the light-emitting layer may be extracted to the outside through the second electrode 190, which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer 220.

[0185] The first capping layer 210 and the second capping layer 220 may serve to improve external light emitting efficiency according to the principle of constructive interference.

[0186] The first capping layer 210 and the second capping layer 220 may be, independently of each other, an organic capping layer made of an organic material, an inorganic capping layer made of an inorganic material, or a composite capping layer containing an organic material and an inorganic material.

[0187] At least one of the first capping layer 210 and the second capping layer 220 may independently include at least one material selected from the group consisting of a carbocyclic compound, an amine compound, an amine-based compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, and an alkaline earth metal complex. The carbocyclic compound, the amine compound, and the amine-based compound may optionally be substituted with a substituent containing at least one element selected from the group consisting of O, N, S, Se, Si, F, Cl, Br, and I. According to an embodiment, at least one of the first capping layer 210 and the second capping layer 220 may independently include an amine-based compound.

[0188] According to other embodiments, at least one of the first capping layer 210 and the second capping layer 220 may independently comprise a compound represented by Formula 201 or a compound represented by Formula 202.

[0189] According to yet another embodiment, at least one of the first capping layer 210 and the second capping layer 220 may independently contain a compound selected from the group consisting of compounds HT28 to HT33, and compounds CP1 to CP5 below, but is not limited thereto. [ka]

[0190] The organic light-emitting device has been described above with reference to FIGS. 1 to 4, but is not limited thereto.

[0191] Each layer included in the hole transport region, the light emitting layer, and the electron transport region can be formed in a predetermined region using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, ink jet printing, laser printing, and laser induced thermal imaging (LiTI) method.

[0192] When each layer included in the hole transport region, the light emitting layer, and each layer included in the electron transport region are formed by vacuum deposition, the deposition conditions are, for example, a deposition temperature of about 100 to about 500° C., a deposition temperature of about 10 -8 ~about 10 -3 The degree of vacuum of torr and the deposition rate may be selected within the range of about 0.001 nm / sec to about 10 nm / sec, taking into consideration the material contained in the layer to be formed and the structure of the layer to be formed.

[0193] When each layer included in the hole transport region, the light-emitting layer, and each layer included in the electron transport region are formed by spin coating, the coating conditions may be selected, for example, within the range of a coating speed of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80°C to 200°C, taking into consideration the materials included in the layers to be formed and the structure of the layers to be formed.

[0194] [General definition of substituents] As used herein, C1-C 60 The alkyl group means a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, a hexyl group, etc. In this specification, C1-C 60 The alkylene group is C1-C 60 It means a divalent group having the same structure as an alkyl group.

[0195] As used herein, C2-C 60 Alkenyl groups are C2-C 60 It means a hydrocarbon group containing one or more carbon-carbon double bonds in the middle or at the end of the alkyl group, and specific examples thereof include ethenyl, propenyl, and butenyl groups. 60 The alkenylene group is C2-C 60 It means a divalent group having the same structure as an alkenyl group.

[0196] As used herein, C2-C 60 Alkynyl groups are C2-C 60 It means a hydrocarbon group containing one or more carbon-carbon triple bonds in the middle or at the end of the alkyl group, and specific examples thereof include an ethynyl group, a propynyl group, etc. In this specification, C2-C 60 The alkynylene group is C2-C 60 It means a divalent group having the same structure as an alkynyl group.

[0197] As used herein, C1-C 60 The alkoxy group is -OA. 101 (where A 101 is C1-C 60 Specific examples of the alkoxy group include methoxy, ethoxy, and isopropyloxy groups.

[0198] As used herein, C3-C 10 Cycloalkyl groups are C3-C 10 It means a monovalent saturated hydrocarbon monocyclic group, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, etc. 10 The cycloalkylene group is C3-C 10 It means a divalent group having the same structure as a cycloalkyl group.

[0199] As used herein, C1-C 10 Heterocycloalkyl groups are C1-C1 alkyl groups containing at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom. 10 It means a monovalent monocyclic group, and specific examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, etc. 10 The heterocycloalkylene group is C1-C 10 It means a divalent group having the same structure as a heterocycloalkyl group.

[0200] As used herein, C3-C 10 The cycloalkenyl group is C3-C 10 It means a monovalent monocyclic group that has at least one double bond in the ring but does not have aromaticity, and specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. 10 The cycloalkenylene group is C3-C 10 It means a divalent group having the same structure as a cycloalkenyl group.

[0201] As used herein, C1-C 10 The heterocycloalkenyl group is a C1-C6 alkyl group containing at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom. 10 It is a monovalent monocyclic group having at least one double bond in the ring. 10 Specific examples of heterocycloalkenyl groups include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like. 10 The heterocycloalkenylene group is a C1-C 10 It means a divalent group having the same structure as a heterocycloalkenyl group.

[0202] As used herein, C6-C 60 The aryl group is C6-C 60 means a monovalent group having a carbocyclic aromatic system, C6-C 60 The arylene group is C6-C 60 means a divalent group having a carbocyclic aromatic system. C6-C 60 Specific examples of the aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. 60 Aryl groups and C6-C 60 When the arylene group contains more than one ring, the two or more rings may be fused together.

[0203] As used herein, C1-C 60 The heteroaryl group contains at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, and is C1-C 60 means a monovalent group having a heterocyclic aromatic system, C1-C 60 The heteroarylene group contains at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, and is C1-C 60 means a divalent group having a heterocyclic aromatic system. C1-C 60 Specific examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl groups. 60 Heteroaryl groups and C1-C 60 When a heteroarylene group contains more than one ring, the two or more rings may be fused together.

[0204] As used herein, C6-C 60 The aryloxy group is -OA. 102 (where A 102 is C6-C 60 aryl group), and C6-C 60 The arylthio group is -SA 103 (where A 103 is C6-C 60 aryl group).

[0205] As used herein, a monovalent non-aromatic fused polycyclic group refers to a monovalent group (e.g., having 8 to 60 carbon atoms) in which two or more rings are fused together, the ring atoms are carbon only, and the entire molecule is non-aromatic. Specific examples of monovalent non-aromatic fused polycyclic groups include a fluorenyl group. As used herein, a divalent non-aromatic fused polycyclic group refers to a divalent group having the same structure as a monovalent non-aromatic fused polycyclic group.

[0206] As used herein, a monovalent non-aromatic fused heteropolycyclic group refers to a monovalent group (e.g., having 1 to 60 carbon atoms) in which two or more rings are fused together and which contains, in addition to carbon, at least one heteroatom selected from N, O, Si, P, and S as ring-forming atoms, and the entire molecule has a non-aromatic nature. Specific examples of monovalent non-aromatic fused heteropolycyclic groups include a carbazolyl group. As used herein, a divalent non-aromatic fused heteropolycyclic group refers to a divalent group having the same structure as a monovalent non-aromatic fused heteropolycyclic group.

[0207] As used herein, C5-C 60 A carbocyclic group is a C5-C ring containing only carbon atoms. 60 Monocyclic group or C5-C 60 means a polycyclic group. C5-C 60 A carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. 60 A carbocyclic group may be a ring such as benzene, a monovalent group such as phenyl, or a divalent group such as phenylene. 60 Depending on the number of substituents attached to the carbocyclic group, C5-C 60 The carbocyclic group can be variously modified, such as being trivalent or tetravalent.

[0208] As used herein, C1-C 60 Heterocyclic groups are C5-C 60 It means a group that has the same structure as a carbocyclic group, but contains at least one heteroatom selected from N, O, Si, P, and S in addition to carbon (which may have 1 to 60 carbon atoms) as ring-forming atoms.

[0209] As used herein, the aforementioned substituted C5-C 60 Carbocyclic groups, substituted C1-C 60 Heterocyclic groups, substituted C3-C 10 Cycloalkylene groups, substituted C1-C 10 Heterocycloalkylene groups, substituted C3-C 10 Cycloalkenylene groups, substituted C1-C 10 Heterocycloalkenylene groups, substituted C6-C 60 Arylene groups, substituted C1-C 60 Heteroarylene group, substituted divalent non-aromatic fused polycyclic group, substituted divalent non-aromatic fused polycyclic heterocyclic group, substituted C1-C 60 Alkyl groups, substituted C2-C 60 Alkenyl groups, substituted C2-C 60 Alkynyl groups, substituted C1-C 60 Alkoxy groups, substituted C3-C 10 Cycloalkyl groups, substituted C1-C 10 Heterocycloalkyl groups, substituted C3-C 10 Cycloalkenyl groups, substituted C1-C 10 Heterocycloalkenyl groups, substituted C6-C 60 Aryl groups, substituted C6-C 60 Aryloxy groups, substituted C6-C 60 Arylthio groups, substituted C1-C 60 At least one of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituent of the substituted monovalent non-aromatic fused polycyclic heterocyclic group is Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups and C1-C 60 Alkoxy groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl group, 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 ) C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups and C1-C 60 Alkoxy groups; C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups and monovalent non-aromatic fused heteropolycyclic groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl group, 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 ) C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; and -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 selected from The aforementioned Q 11 ~Q 13 , Q 21 ~Q 23 , and Q 31 ~Q 33 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C1-C 60 It may be selected from heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic hetero-fused polycyclic groups, biphenylyl groups, and terphenylyl groups.

[0210] As used herein, "Ph" means a phenyl group, "Me" means a methyl group, "Et" means an ethyl group, "ter-Bu" or "But" means a tert-butyl group, and "OMe" means a methoxy group.

[0211] In this specification, the term "biphenylyl group" means a "phenyl group substituted with a phenyl group." The term "biphenylyl group" refers to a group in which the substituent is "C6-C 60 It belongs to the "substituted phenyl group" which is an "aryl group."

[0212] In this specification, the term "terphenylyl group" means a "phenyl group substituted with a biphenylyl group." The term "terphenylyl group" refers to a group in which the substituent is "C6-C 60 C6-C substituted with aryl groups 60 It belongs to the "substituted phenyl group" which is an "aryl group."

[0213] In this specification, unless otherwise defined, * and *' refer to bonding sites between adjacent atoms in the chemical formula. [Example]

[0214] The compound and organic light-emitting device according to one embodiment of the present invention will be described in more detail below with reference to synthesis examples and examples. In the synthesis examples below, when the expression "B was used instead of A," the molar equivalents of A and B are the same.

[0215] Intermediate 1: Synthesis of C(1) [ka]

[0216] Synthesis of C(1)-1: (Phenyl-d5)boronic acid (1 eq, 1.27 g), 4-iodo-1,1'-biphenyl (1 eq, 2.8 g), Pd(PPh3)4 (0.05 eq, 0.56 g), K2CO3 (3 eq, 4.14 g), 20 ml of tetrahydrofuran (THF), and 5 ml of HO were stirred in a single-necked round-bottom flask at 80 °C for 6 h. The reaction mixture was worked up with ethyl acetate (EA) / HO and then separated by column chromatography (dichloromethane (MC) / HO). x = 1 / 50). 1.88 g was obtained (yield = 80%, purity = 99%).

[0217] Synthesis of C(1): C(1)-1 (1 eq, 1.88 g), N-bromosuccinimide (NBS) (2.2 eq, 3.1 g), and 20 ml of MC were placed in a single-neck round-bottom flask and stirred at 30°C for 6 hours. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H x = 1 / 100). 2.8 g was obtained (yield = 90%, purity = 98%).

[0218] Intermediate 2: Synthesis of C(2) [ka]

[0219] Synthesis of C(2)-1: 1,4-Dibromobenzene-2,3,5,6-d4 (1 eq, 2.4 g), phenylboronic acid (2.2 eq, 2.7 g), Pd(PPh3)4 (0.05 eq, 0.56 g), K2CO3 (3 eq, 4.14 g), 20 ml of THF, and 5 ml of HO were stirred in a single-necked round-bottom flask at 80 °C for 6 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H2O). x = 1 / 50). 1.87 g was obtained (yield = 78%, purity = 99%).

[0220] Synthesis of C(2): C(2)-1 (1 eq, 1.87 g), NBS (2.2 eq, 3.05 g), and 20 ml of MC were placed in a single-neck round-bottom flask and stirred at 30 °C for 6 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / Hx = 1 / 100). 2.8 g of the product was obtained (yield = 90%, purity = 98%).

[0221] Intermediate 3: Synthesis of C(3) [ka]

[0222] Synthesis of C(3)-1: Phenylboronic acid (1 eq, 1.21 g), 4-iodo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 (1 eq, 2.89 g), Pd(PPh3)4 (0.05 eq, 0.56 g), K2CO3 (3 eq, 4.14 g), 20 ml of THF, and 5 ml of HO were placed in a single-necked round-bottom flask and stirred at 80 °C for 6 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / HO). x = 1 / 50). 1.91 g was obtained (yield = 80%, purity = 99%).

[0223] Synthesis of C(3): C(3)-1 (1 eq, 1.91 g), NBS (2.2 eq, 3.1 g), and 20 ml of MC were placed in a single-necked round-bottom flask and stirred at 30°C for 6 hours. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H x = 1 / 100). 2.78 g was obtained (yield = 88%, purity = 98%).

[0224] Intermediate 4: Synthesis of C(4) [ka]

[0225] Synthesis of C(4)-1: 1,4-Dibromobenzene (1 eq, 2.36 g), (phenyl-d5)boronic acid (2.2 eq, 2.8 g), Pd(PPh3)4 (0.05 eq, 0.56 g), K2CO3 (3 eq, 4.14 g), 20 ml of THF, and 5 ml of HO were placed in a single-necked round-bottom flask and stirred at 80 °C for 6 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H2O). x = 1 / 50). 2.1 g was obtained (yield = 88%, purity = 99%).

[0226] Synthesis of C(4): C(4)-1 (1 eq, 2.1 g), NBS (2.2 eq, 3.45 g), and 20 ml of MC were placed in a single-neck round-bottom flask and stirred at 30 °C for 6 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / Hx = 1 / 100). 3.13 g of the product was obtained (yield = 90%, purity = 99%).

[0227] Intermediate 5: Synthesis of C(5) [ka]

[0228] Synthesis of C(5)-1: (Phenyl-d5)boronic acid (1 eq, 1.27 g), 4-iodo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 (1 eq, 2.89 g), Pd(PPh3)4 (0.05 eq, 0.56 g), K2CO3 (3 eq, 4.14 g), 20 ml of THF, and 5 ml of HO were stirred in a single-neck round-bottom flask at 80 °C for 6 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / HO). x = 1 / 50). 1.88 g was obtained (yield = 80%, purity = 99%).

[0229] Synthesis of C(5): C(1)-1 (1 eq, 1.88 g), NBS (2.2 eq, 3.1 g), and 20 ml of MC were placed in a single-necked round-bottom flask and stirred at 30°C for 6 hours. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H x = 1 / 100). 2.67 g was obtained (yield = 86%, purity = 98%).

[0230] Synthesis Example 1: Synthesis of Compound 1 [ka]

[0231] Intermediate C(1) (1 eq, 3.92 g), diphenylamine (DPA) (2.2 eq, 3.72 g), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3) (0.05 eq, 0.46 g), t-BuONa (3 eq, 2.88 g), t-Bu3P (0.1 eq, 0.11 ml), and 100 ml of toluene were placed in a single-necked round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H2O). x = 1 / 5). 4.08 g was obtained (yield = 72%, purity = 96%). The purity was increased through ether recrystallization. After the purity reached 99.5% or higher, sublimation purification was carried out. 3.5 g was obtained (P≧99.9%).

[0232] Synthesis Example 2: Synthesis of Compound 2 [ka]

[0233] Synthesis of 2-P1: Intermediate C(1) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.36 g was obtained (yield = 70%, purity = 99%).

[0234] Synthesis of compound 2: 2-P1 (1 eq, 3.36 g), N-phenyl-[1,1'-biphenyl]-4-amine (1 eq, 1.71 g), Pd2(dba)3 (0.03 eq, 0.189 g), t-BuONa (1.5 eq, 1 g), t-BuP (0.05 eq, 0.04 ml), and 100 ml of Toluene were placed in a single-necked round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / HO). x = 1 / 5). 3.7 g was obtained (yield = 82%, purity = 98%). The purity was increased through ether recrystallization. After the purity reached 99.8% or higher, sublimation purification was carried out. 3.3 g was obtained (P≧99.9%).

[0235] Synthesis Example 3: Synthesis of Compound 5 [ka]

[0236] Synthesis of 5-P1: Intermediate C(1) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.36 g was obtained (yield = 70%, purity = 99%).

[0237] Synthesis of compound 5: 5-P1 (1 eq, 3.36 g), 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (1 eq, 1.99 g), Pd2(dba)3 (0.03 eq, 0.189 g), t-BuONa (1.5 eq, 1 g), t-BuP (0.05 eq, 0.04 ml), and a 100 ml solution were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / HO). x = 1 / 5). 3.4 g was obtained (yield = 75%, purity = 98%). The purity was increased through ether recrystallization. After the purity reached 99.8% or more, sublimation purification was carried out. 3 g was obtained (P≧99.9%).

[0238] Synthesis Example 4: Synthesis of Compound 11 [ka]

[0239] Synthesis of 11-P1: Intermediate C(1) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.36 g was obtained (yield = 70%, purity = 99%).

[0240] Synthesis of compound 11: 11-P1 (1 eq, 3.36 g), N,9-diphenyl-9H-carbazol-3-amine (1 eq, 2.34 g), Pd2(dba)3 (0.03 eq, 0.189 g), t-BuONa (1.5 eq, 1 g), t-BuP (0.05 eq, 0.04 ml), and a 100 ml solution were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / HO). x = 1 / 5). 2.86 g was obtained (yield = 63%, purity = 98%). The purity was increased through ether recrystallization. After the purity reached 99.8% or higher, sublimation purification was carried out. 2.5 g was obtained (P≧99.9%).

[0241] Synthesis Example 5: Synthesis of Compound 14 [ka]

[0242] Synthesis of 14-P1: Intermediate C(1) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.36 g was obtained (yield = 70%, purity = 99%).

[0243] Synthesis of compound 14: 14-P1 (1 eq, 3.36 g), N-phenyl-[1,1'-biphenyl]-2-amine (1 eq, 1.7 g), Pd2(dba)3 (0.03 eq, 0.189 g), t-BuONa (1.5 eq, 1 g), t-BuP (0.05 eq, 0.04 ml), and a 100 ml solution were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H2O). x = 1 / 5). 3.58 g was obtained (yield = 79%, purity = 97%). The purity was increased through ether recrystallization. After the purity reached 99.8% or more, sublimation purification was carried out. 3.3 g was obtained (P≧99.9%).

[0244] Synthesis Example 6: Synthesis of Compound 16 [ka]

[0245] Synthesis of 16-P1: Intermediate C(1) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.36 g was obtained (yield = 70%, purity = 99%).

[0246] Synthesis of compound 16: 16-P1 (1 eq, 3.36 g), N-phenylnaphthalen-1-amine (1 eq, 1.53 g), Pd2(dba)3 (0.03 eq, 0.189 g), t-BuONa (1.5 eq, 1 g), t-BuP (0.05 eq, 0.04 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H2O). x = 1 / 5). 3.76 g was obtained (yield = 83%, purity = 99%). The purity was increased through ether recrystallization. After the purity reached 99.8% or higher, sublimation purification was carried out. 3.5 g was obtained (P≧99.9%).

[0247] Synthesis Example 7: Synthesis of Compound 17 [ka]

[0248] Synthesis of 17-P1: Intermediate C(1) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.36 g was obtained (yield = 70%, purity = 99%).

[0249] Synthesis of compound 17: 17-P1 (1 eq, 3.36 g), N-phenylnaphthalen-1-amine (1 eq, 1.53 g), Pd2(dba)3 (0.03 eq, 0.189 g), t-BuONa (1.5 eq, 1 g), t-BuP (0.05 eq, 0.04 ml), and a 100 ml solution were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / HO). x = 1 / 5). 3.76 g was obtained (yield = 83%, purity = 99%). The purity was increased through ether recrystallization. After the purity reached 99.8% or higher, sublimation purification was carried out. 3.5 g was obtained (P≧99.9%).

[0250] Synthesis Example 8: Synthesis of Compound 19 [ka]

[0251] Synthesis of 19-P1: Intermediate C(1) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.36 g was obtained (yield = 70%, purity = 99%).

[0252] Synthesis of compound 19: 19-P1 (1 eq, 3.36 g), 2-(naphthalen-1-yl)-N-phenylaniline (1 eq, 2.06 g), Pd2(dba)3 (0.03 eq, 0.189 g), t-BuONa (1.5 eq, 1 g), t-BuP (0.05 eq, 0.04 ml), and a 100 ml solution were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H2O). x = 1 / 5). 3.62 g was obtained (yield = 80%, purity = 99%). The purity was increased through ether recrystallization. After the purity reached 99.8% or higher, sublimation purification was carried out. 3.42 g was obtained (P≧99.9%).

[0253] Synthesis Example 9: Synthesis of Compound 25 [ka]

[0254] Synthesis of compound 25: Intermediate C(2) (1 eq, 3.92 g), DPA (2.2 eq, 3.72 g), Pd(dba) (0.05 eq, 0.46 g), t-BuONa (3 eq, 2.88 g), t-BuP (0.1 eq, 0.11 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / HO). x = 1 / 5). 4.25 g was obtained (yield = 75%, purity = 98%). The purity was increased through ether recrystallization. After the purity reached 99.7% or higher, sublimation purification was carried out. 4 g was obtained (P≧99.9%).

[0255] Synthesis Example 10: Synthesis of Compound 26 [ka]

[0256] Synthesis of 26-P1: Intermediate C(2) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.84 g was obtained (yield = 80%, purity = 99%).

[0257] Synthesis of compound 26: 26-P1 (1 eq, 3.84 g), N-phenyl-[1,1'-biphenyl]-4-amine (1 eq, 1.95 g), Pd2(dba)3 (0.03 eq, 0.216 g), t-BuONa (1.5 eq, 1.14 g), t-BuP (0.05 eq, 0.046 ml), and 100 ml of Toluene were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / HO). x = 1 / 5). 4.23 g was obtained (yield = 82%, purity = 98%). The purity was increased through ether recrystallization. After the purity reached 99.6% or higher, sublimation purification was carried out. 3.9 g was obtained (P≧99.9%).

[0258] Synthesis Example 11: Synthesis of Compound 29 [ka]

[0259] Synthesis of 29-P1: Intermediate C(2) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.84 g was obtained (yield = 80%, purity = 99%).

[0260] Synthesis of compound 29: 29-P1 (1 eq, 3.84 g), 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (1 eq, 2.28 g), Pd2(dba)3 (0.03 eq, 0.216 g), t-BuONa (1.5 eq, 1.14 g), t-BuP (0.05 eq, 0.046 ml), and a 100 ml solution were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / HO). x = 1 / 5). 4.13 g was obtained (yield = 80%, purity = 98%). The purity was increased through ether recrystallization. After the purity reached 99.6% or higher, sublimation purification was carried out. 3.7 g was obtained (P≧99.9%).

[0261] Synthesis Example 12: Synthesis of Compound 38 [ka]

[0262] Synthesis of 38-P1: Intermediate C(2) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.84 g was obtained (yield = 80%, purity = 99%).

[0263] Synthesis of compound 38: 38-P1 (1 eq, 3.84 g), N-phenyl-[1,1'-biphenyl]-2-amine (1 eq, 1.95 g), Pd2(dba)3 (0.03 eq, 0.216 g), t-BuONa (1.5 eq, 1.14 g), t-BuP (0.05 eq, 0.046 ml), and 100 ml of Toluene were placed in a single-necked round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / HO). x = 1 / 5). 3.97 g was obtained (yield = 77%, purity = 99%). The purity was increased through ether recrystallization. After the purity reached 99.6% or higher, sublimation purification was carried out. 3.65 g was obtained (P≧99.9%).

[0264] Synthesis Example 13: Synthesis of Compound 40 [ka]

[0265] Synthesis of 40-P1: Intermediate C(2) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.36 g was obtained (yield = 70%, purity = 99%).

[0266] Synthesis of compound 40: 40-P1 (1 eq, 3.36 g), N-phenylnaphthalen-1-amine (1 eq, 1.53 g), Pd2(dba)3 (0.03 eq, 0.189 g), t-BuONa (1.5 eq, 1 g), t-BuP (0.05 eq, 0.04 ml), and a 100 ml volume of ethanol were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / HO). x = 1 / 5). 3.76 g was obtained (yield = 83%, purity = 99%). The purity was increased through ether recrystallization. After the purity reached 99.8% or higher, sublimation purification was carried out. 3.5 g was obtained (P≧99.9%).

[0267] Synthesis Example 14: Synthesis of Compound 41 [ka]

[0268] Synthesis of 41-P1: Intermediate C(2) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.36 g was obtained (yield = 70%, purity = 99%).

[0269] Synthesis of compound 41: 41-P1 (1 eq, 3.36 g), N-phenylnaphthalen-1-amine (1 eq, 1.53 g), Pd2(dba)3 (0.03 eq, 0.189 g), t-BuONa (1.5 eq, 1 g), t-BuP (0.05 eq, 0.04 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H2O). x = 1 / 5). 3.76 g was obtained (yield = 83%, purity = 99%). The purity was increased through ether recrystallization. After the purity reached 99.8% or higher, sublimation purification was carried out. 3.5 g was obtained (P≧99.9%).

[0270] Synthesis Example 15: Synthesis of Compound 49 [ka]

[0271] Synthesis of compound 49: Intermediate C(3) (1 eq, 3.96 g), DPA (2.2 eq, 3.72 g), Pd(dba) (0.05 eq, 0.46 g), t-BuONa (3 eq, 2.88 g), t-BuP (0.1 eq, 0.11 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 4.34 g was obtained (yield = 76%, purity = 98%). The purity was increased through ether recrystallization. After the purity reached 99.7% or higher, sublimation purification was carried out. 4.1 g was obtained (P≧99.9%).

[0272] Synthesis Example 16: Synthesis of Compound 50 [ka]

[0273] Synthesis of 50-P1: Intermediate C(3) (1 eq, 3.96 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.87 g was obtained (yield = 80%, purity = 99%).

[0274] Synthesis of compound 50: 50-P1 (1 eq, 3.87 g), N-phenyl-[1,1'-biphenyl]-4-amine (1 eq, 1.95 g), Pd2(dba)3 (0.03 eq, 0.216 g), t-BuONa (1.5 eq, 1.14 g), t-BuP (0.05 eq, 0.046 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H2O). x = 1 / 5). 4 g was obtained (yield = 77%, purity = 98.5%). The purity was increased through ether recrystallization. After the purity reached 99.7% or higher, sublimation purification was carried out. 3.6 g was obtained (P≧99.9%).

[0275] Synthesis Example 17: Synthesis of Compound 53 [ka]

[0276] Synthesis of 53-P1: Intermediate C(3) (1 eq, 3.96 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.87 g was obtained (yield = 80%, purity = 99%).

[0277] Synthesis of compound 53: 53-P1 (1 eq, 3.87 g), 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (1 eq, 2.28 g), Pd2(dba)3 (0.03 eq, 0.216 g), t-BuONa (1.5 eq, 1.14 g), t-BuP (0.05 eq, 0.046 ml), and a 100 ml solution were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / HO). x = 1 / 5). 4.2 g was obtained (yield = 81%, purity = 98.9%). The purity was increased through ether recrystallization. After the purity reached 99.7% or higher, sublimation purification was carried out. 3.8 g was obtained (P≧99.9%).

[0278] Synthesis Example 18: Synthesis of Compound 62 [ka]

[0279] Synthesis of 62-P1: Intermediate C(3) (1 eq, 3.96 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.87 g was obtained (yield = 80%, purity = 99%).

[0280] Synthesis of compound 62: 62-P1 (1 eq, 3.87 g), N-phenyl-[1,1'-biphenyl]-2-amine (1 eq, 1.95 g), Pd2(dba)3 (0.03 eq, 0.216 g), t-BuONa (1.5 eq, 1.14 g), t-BuP (0.05 eq, 0.046 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / HO). x = 1 / 5). 4 g was obtained (yield = 77%, purity = 99%). The purity was increased through ether recrystallization. After the purity reached 99.88% or higher, sublimation purification was carried out. 3.6 g was obtained (P≧99.9%).

[0281] Synthesis Example 19: Synthesis of Compound 64 [ka]

[0282] Synthesis of 64-P1: Intermediate C(3) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.36 g was obtained (yield = 70%, purity = 99%).

[0283] Synthesis of compound 64: 64-P1 (1 eq, 3.36 g), N-phenylnaphthalen-1-amine (1 eq, 1.53 g), Pd2(dba)3 (0.03 eq, 0.189 g), t-BuONa (1.5 eq, 1 g), t-BuP (0.05 eq, 0.04 ml), and a 100 ml solution were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H2O). x = 1 / 5). 3.76 g was obtained (yield = 83%, purity = 99%). The purity was increased through ether recrystallization. After the purity reached 99.8% or higher, sublimation purification was carried out. 3.5 g was obtained (P≧99.9%).

[0284] Synthesis Example 20: Synthesis of Compound 65 [ka]

[0285] Synthesis of 65-P1: Intermediate C(3) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.36 g was obtained (yield = 70%, purity = 99%).

[0286] Synthesis of compound 65: 65-P1 (1 eq, 3.36 g), N-phenylnaphthalen-1-amine (1 eq, 1.53 g), Pd2(dba)3 (0.03 eq, 0.189 g), t-BuONa (1.5 eq, 1 g), t-BuP (0.05 eq, 0.04 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H2O). x = 1 / 5). 3.76 g was obtained (yield = 83%, purity = 99%). The purity was increased through ether recrystallization. After the purity reached 99.8% or higher, sublimation purification was carried out. 3.5 g was obtained (P≧99.9%).

[0287] Synthesis Example 21: Synthesis of Compound 73 [ka]

[0288] Synthesis of compound 73: Intermediate C(4) (1 eq, 3.96 g), DPA (2.2 eq, 3.72 g), Pd(dba) (0.05 eq, 0.46 g), t-BuONa (3 eq, 2.88 g), t-BuP (0.1 eq, 0.11 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 4 g was obtained (yield = 70%, purity = 99.2%). The purity was increased through ether recrystallization. After the purity reached 99.65% or higher, sublimation purification was carried out. 3.7 g was obtained (P≧99.9%).

[0289] Synthesis Example 22: Synthesis of Compound 74 [ka]

[0290] Synthesis of 74-P1: Intermediate C(4) (1 eq, 3.96 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.87 g was obtained (yield = 80%, purity = 99%).

[0291] Synthesis of compound 74: 74-P1 (1 eq, 3.87 g), N-phenyl-[1,1'-biphenyl]-4-amine (1 eq, 1.95 g), Pd2(dba)3 (0.03 eq, 0.216 g), t-BuONa (1.5 eq, 1.14 g), t-BuP (0.05 eq, 0.046 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H2O). x = 1 / 5). 4.36 g was obtained (yield = 84%, purity = 97%). The purity was increased through ether recrystallization. After the purity reached 99.5% or higher, sublimation purification was carried out. 4.1 g was obtained (P≧99.9%).

[0292] Synthesis Example 23: Synthesis of Compound 77 [ka]

[0293] Synthesis of 77-P1: Intermediate C(4) (1 eq, 3.96 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.87 g was obtained (yield = 80%, purity = 99%).

[0294] Synthesis of compound 77: 74-P1 (1 eq, 3.87 g), 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (1 eq, 2.28 g), Pd2(dba)3 (0.03 eq, 0.216 g), t-BuONa (1.5 eq, 1.14 g), t-BuP (0.05 eq, 0.046 ml), and a 100 ml solution were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / HO). x = 1 / 5). 4.2 g was obtained (yield = 81%, purity = 99%). The purity was increased through ether recrystallization. After the purity reached 99.8% or higher, sublimation purification was carried out. 3.85 g was obtained (P≧99.9%).

[0295] Synthesis Example 24: Synthesis of Compound 86 [ka]

[0296] Synthesis of 86-P1: Intermediate C(4) (1 eq, 3.96 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.87 g was obtained (yield = 80%, purity = 99%).

[0297] Synthesis of compound 86: 86-P1 (1 eq, 3.87 g), N-phenyl-[1,1'-biphenyl]-2-amine (1 eq, 1.95 g), Pd2(dba)3 (0.03 eq, 0.216 g), t-BuONa (1.5 eq, 1.14 g), t-BuP (0.05 eq, 0.046 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H2O). x = 1 / 5). 4.36 g was obtained (yield = 84%, purity = 98.1%). The purity was increased through ether recrystallization. After the purity reached 99% or more, sublimation purification was carried out. 4 g was obtained (P≧99.9%).

[0298] Synthesis Example 25: Synthesis of Compound 88 [ka]

[0299] Synthesis of 88-P1: Intermediate C(4) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.36 g was obtained (yield = 70%, purity = 99%).

[0300] Synthesis of compound 88: 88-P1 (1 eq, 3.36 g), N-phenylnaphthalen-1-amine (1 eq, 1.53 g), Pd2(dba)3 (0.03 eq, 0.189 g), t-BuONa (1.5 eq, 1 g), t-BuP (0.05 eq, 0.04 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H2O). x = 1 / 5). 3.76 g was obtained (yield = 83%, purity = 99%). The purity was increased through ether recrystallization. When the purity reached 99.8% or more, sublimation purification was performed. 3.5 g was obtained (P≧99.9%).

[0301] Synthesis Example 26: Synthesis of Compound 89 [ka]

[0302] Synthesis of 89-P1: Intermediate C(4) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 3.36 g was obtained (yield = 70%, purity = 99%).

[0303] Synthesis of compound 89: 89-P1 (1 eq, 3.36 g), N-phenylnaphthalen-1-amine (1 eq, 1.53 g), Pd2(dba)3 (0.03 eq, 0.189 g), t-BuONa (1.5 eq, 1 g), t-Bu3P (0.05 eq, 0.04 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H2O). x = 1 / 5). 3.76 g was obtained (yield = 83%, purity = 99%). The purity was increased through ether recrystallization. After the purity reached 99.8% or higher, sublimation purification was carried out. 3.5 g was obtained (P≧99.9%).

[0304] Synthesis Example 27: Synthesis of Compound 97 [ka]

[0305] Synthesis of Compound 97: Intermediate C(5) (1 eq, 4 g), DPA (2.2 eq, 3.72 g), Pd(dba) (0.05 eq, 0.46 g), t-BuONa (3 eq, 2.88 g), t-BuP (0.1 eq, 0.11 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / HO). x = 1 / 5). 5 g was obtained (yield = 88%, purity = 99%). The purity was increased through ether recrystallization. After the purity reached 99.9% or higher, sublimation purification was carried out. 4.66 g was obtained (P≧99.9%).

[0306] Synthesis Example 28: Synthesis of Compound 110 [ka]

[0307] Synthesis of 110-P1: Intermediate C(5) (1 eq, 4 g), DPA (1 eq, 1.69 g), Pd(dba) (0.03 eq, 0.27 g), t-BuONa (1.5 eq, 1.44 g), t-BuP (0.05 eq, 0.06 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H). x = 1 / 5). 4.15 g was obtained (yield = 85%, purity = 97%).

[0308] Synthesis of compound 110: 110-P1 (1 eq, 4.15 g), N-phenyl-[1,1'-biphenyl]-2-amine (1 eq, 2.08 g), Pd2(dba)3 (0.03 eq, 0.216 g), t-BuONa (1.5 eq, 1.14 g), t-BuP (0.05 eq, 0.046 ml), and a 100 ml volume were placed in a single-neck round-bottom flask and stirred at 100 °C for 2 h. The reaction mixture was worked up with EA / HO and then separated by column chromatography (MC / H2O). x = 1 / 5). 4.37 g was obtained (yield = 79%, purity = 98.8%). The purity was increased through ether recrystallization. After the purity reached 99.7% or higher, sublimation purification was carried out. 4 g was obtained (P≧99.9%).

[0309] Compounds synthesized in Synthesis Examples 1 to 28 1 The 1 H NMR and MS / FAB results are shown in Table 1 below.

[0310] Those skilled in the art will be able to easily recognize methods for synthesizing compounds other than those shown in Table 1 by referring to the synthetic routes and raw materials described above. [Table 1] TIFF0007797120000125.tif111167

[0311] Comparative Example 1 The anode was obtained from Corning and had a resistance of 15 Ω / cm. 2 A (120 nm) ITO glass substrate was cut to a size of 50 mm × 50 mm × 0.7 mm, ultrasonically cleaned using isopropyl alcohol and pure water for 5 minutes each, and then cleaned by irradiating with ultraviolet light and exposing to ozone for 30 minutes, and then the glass substrate was placed in a vacuum deposition apparatus.

[0312] First, a hole injection layer (60 nm thick) of the known substance 2-TNATA was vacuum-deposited on top of the substrate, and then a hole transport layer (30 nm thick) of the hole transport substance 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was vacuum-deposited on top of the substrate.

[0313] On top of the hole transport layer, a known blue fluorescent host, 9,10-di(2-naphthyl)anthracene (ADN), and a known blue fluorescent dopant, 4,4′-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), were co-evaporated in a weight ratio of 98:2 to form a 30-nm-thick light-emitting layer. [ka] [ka]

[0314] Next, Alq3 was vapor-deposited to a thickness of 30 nm on top of the light-emitting layer as an electron transport layer, and then LiF, an alkali metal halide, was vapor-deposited to a thickness of 1 nm on top of the electron transport layer as an electron injection layer, and Al was vacuum-deposited to a thickness of 300 nm (negative electrode) to form a LiF / Al electrode, thereby producing an organic electroluminescent device.

[0315] Examples 1 to 21 An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that the compound shown in Table 2 below was used instead of NPB when forming the hole transport layer.

[0316] Comparative Examples 2 to 7 Organic light-emitting devices were produced in the same manner as in Comparative Example 1, except that the following compounds A to F were used instead of NPB when forming the hole transport layer. [ka] [ka]

[0317] Evaluation example 1 The driving voltage, current density, luminance, efficiency, emitted light, and light-emitting lifetime of the organic light-emitting devices fabricated in Examples 1 to 28 and Comparative Examples 1 to 7 were measured at 600 nit using a Keithley SMU 236 and a luminance meter PR650. The results are shown in Table 2 below. [Table 2] TIFF0007797120000131.tif25167

[0318] From Table 2, it was confirmed that the organic light-emitting devices of Examples 1 to 28 had lower driving voltages and higher efficiencies than the organic light-emitting devices of Comparative Examples 1 to 7. It was also confirmed that the organic light-emitting devices of Examples 1 to 28 exhibited higher brightness and longer lifespans than the organic light-emitting devices of Comparative Examples 1 to 7.

[0319] Although the present invention has been described with reference to synthesis examples and examples, these are merely illustrative, and a person skilled in the art of the present invention will understand that various modifications and equivalent embodiments are possible from these examples. Therefore, the true technical scope of protection of the present invention is defined by the technical spirit of the claims. [Explanation of symbols]

[0320] 10,20,30,40 Organic light-emitting devices 110 1st electrode 150 Organic layer 190 2nd electrode 210 First capping layer 220 Second Capping Layer

Claims

1. A first electrode; a second electrode facing the first electrode; an organic layer disposed between the first electrode and the second electrode and including a light-emitting layer; An organic light-emitting device comprising one or more amine compounds represented by the following chemical formula 1: [Chemical formula 1] 【Chemistry 1】 L １ ~L ４ , and L １１ ~L １２ are each independently a substituted or unsubstituted C ５ -C ６０ a carbocyclic group, or a substituted or unsubstituted C １ -C ６０ is a heterocyclic group, a1 to a4, a11 and a12 are each independently an integer selected from 0 to 5; Ar １ ~Ar ４ are each independently a substituted or unsubstituted C ５ -C ６０ a carbocyclic group, or a substituted or unsubstituted C １ -C ６０ is a heterocyclic group, However, Ar １ ~Ar ４ If two or more of the amino groups are present, they are excluded. R １ ~R ３ represents hydrogen, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C １ -C ６０ alkyl group, substituted or unsubstituted C ２ -C ６０ Alkenyl group, substituted or unsubstituted C ２ -C ６０ Alkynyl group, substituted or unsubstituted C １ -C ６０ Alkoxy group, substituted or unsubstituted C ３ -C １０ Cycloalkyl groups, substituted or unsubstituted C １ -C １０ Heterocycloalkyl groups, substituted or unsubstituted C ３ -C １０ Cycloalkenyl group, substituted or unsubstituted C １ -C １０ heterocycloalkenyl group, substituted or unsubstituted C ６ -C ６０ aryl group, substituted or unsubstituted C ６ -C ６０ aryloxy group, substituted or unsubstituted C ６ -C ６０ arylthio group, substituted or unsubstituted C １ -C ６０ a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a 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)(Q １ ), or -P(=O)(Q １ ) (Q ２ ) and D １ ~D ３ is deuterium, b1 to b3 and c1 to c3 are each independently an integer selected from 0 to 4; However, b1+c1, b2+c2, and b3+c3 are each 4, however, One of the c1 to c3 is 4 and the remaining two are 0, Two of the c1 to c3 are 4 and the remaining one is 0, or c1 to c3 are all 4, In the above Chemical Formula 1 【Chemistry 2】 is selected from groups represented by the following chemical formulas 2-1 to 2-6: [Chemical formula 2-1] 【Transformation 3】 [Chemical formula 2-2] 【Chemistry 4】 [Chemical formula 2-3] 【Transformation 5】 [Chemical formula 2-4] 【Transformation 6】 [Chemical formula 2-5] 【Transformation 7】 [Chemical formula 2-6] 【Transformation 8】 In the chemical formulas 2-1 to 2-6, * and *' are bonding sites with adjacent atoms, The aforementioned substituted C ５ -C ６０ Carbocyclic groups, substituted C １ -C ６０ Heterocyclic groups, substituted C １ -C ６０ Alkyl groups, substituted C ２ -C ６０ Alkenyl groups, substituted C ２ -C ６０ Alkynyl group, substituted C １ -C ６０ Alkoxy groups, substituted C ３ -C １０ Cycloalkyl groups, substituted C １ -C １０ Heterocycloalkyl groups, substituted C ３ -C １０ Cycloalkenyl group, substituted C １ -C １０ Heterocycloalkenyl groups, substituted C ６ -C ６０ Aryl groups, substituted C ６ -C ６０ Aryloxy groups, substituted C ６ -C ６０ Arylthio groups, substituted C １ -C ６０ At least one of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituent of the substituted monovalent non-aromatic fused polycyclic heterocyclic group is Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C １ -C ６０ Alkyl group, C ２ -C ６０ Alkenyl group, C ２ -C ６０ Alkynyl group, C １ -C ６０ an alkoxy group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ３ -C １０ Cycloalkyl group, C １ -C １０ Heterocycloalkyl group, C ３ -C １０ Cycloalkenyl group, C １ -C １０ Heterocycloalkenyl group, C ６ -C ６０ Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ Arylthio group, C １ -C ６０ Heteroaryl group, 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 C) １ -C ６０ Alkyl group, C ２ -C ６０ Alkenyl group, C ２ -C ６０ Alkynyl group and C １ -C ６０ an alkoxy group; C ３ -C １０ Cycloalkyl group, C １ -C １０ Heterocycloalkyl group, C ３ -C １０ Cycloalkenyl group, C １ -C １０ Heterocycloalkenyl group, C ６ -C ６０ Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ Arylthio group, C １ -C ６０ Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C １ -C ６０ Alkyl group, C ２ -C ６０ Alkenyl group, C ２ -C ６０ Alkynyl group, C １ -C ６０ Alkoxy group, C ３ -C １０ Cycloalkyl group, C １ -C １０ Heterocycloalkyl group, C ３ -C １０ Cycloalkenyl group, C １ -C １０ Heterocycloalkenyl group, C ６ -C ６０ Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ Arylthio group, C １ -C ６０ Heteroaryl group, 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 C) ３ -C １０ Cycloalkyl group, C １ -C １０ Heterocycloalkyl group, C ３ -C １０ Cycloalkenyl group, C １ -C １０ Heterocycloalkenyl group, C ６ -C ６０ Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ Arylthio group, C １ -C ６０ Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; and -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 selected from The aforementioned Q １ ~Q ３ , Q １１ ~Q １３ , Q ２１ ~Q ２３ , and Q ３１ ~Q ３３ are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C １ -C ６０ Alkyl group, C ２ -C ６０ Alkenyl group, C ２ -C ６０ Alkynyl group, C １ -C ６０ Alkoxy group, C ３ -C １０ Cycloalkyl group, C １ -C １０ Heterocycloalkyl group, C ３ -C １０ Cycloalkenyl group, C １ -C １０ Heterocycloalkenyl group, C ６ -C ６０ Aryl group, C １ -C ６０ It is selected from the group consisting of heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic hetero-fused polycyclic groups, biphenylyl groups, and terphenylyl groups.

2. the first electrode is an anode; the second electrode is a cathode; the organic layer further includes a hole transport region disposed between the first electrode and the light-emitting layer, and an electron transport region disposed between the light-emitting layer and the second electrode; the hole transport region includes a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron blocking layer, or any combination thereof; 10. The organic light-emitting device of claim 1, wherein the electron transport region comprises a buffer layer, a hole blocking layer, an electron modulating layer, an electron transport layer, an electron injection layer, or any combination thereof.

3. The organic light-emitting device according to claim 2 , wherein the hole transport region contains the amine compound.

4. The organic light-emitting device according to claim 3 , wherein the hole transport region comprises a hole transport layer, and the amine compound is contained in the hole transport layer.

5. The organic light-emitting device of claim 4 , wherein the hole transport region further comprises a p-dopant having a LUMO energy level lower than −3.5 eV.

6. the light-emitting layer comprises a host and a dopant; The organic light-emitting device according to claim 3 , wherein the dopant is a fluorescent dopant containing a styryl compound.

7. the light-emitting layer comprises a host and a dopant; The organic light-emitting device of claim 3 , wherein the dopant is a phosphorescent dopant.

8. 3. The organic light-emitting device of claim 2, wherein the electron transport region comprises an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

9. An amine compound represented by the following chemical formula 1: [Chemical formula 1] 【Chemistry 9】 L １ ~L ４ , and L １１ ~L １２ are each independently a substituted or unsubstituted C ５ -C ６０ a carbocyclic group, or a substituted or unsubstituted C １ -C ６０ is a heterocyclic group, a1 to a4, a11 and a12 are each independently an integer selected from 0 to 5; Ar １ ~Ar ４ are each independently a substituted or unsubstituted C ５ -C ６０ a carbocyclic group, or a substituted or unsubstituted C １ -C ６０ is a heterocyclic group, However, Ar １ ~Ar ４ If two or more of the amino groups are present, they are excluded. R １ ~R ３ represents hydrogen, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C １ -C ６０ alkyl group, substituted or unsubstituted C ２ -C ６０ Alkenyl group, substituted or unsubstituted C ２ -C ６０ Alkynyl group, substituted or unsubstituted C １ -C ６０ Alkoxy group, substituted or unsubstituted C ３ -C １０ Cycloalkyl groups, substituted or unsubstituted C １ -C １０ Heterocycloalkyl groups, substituted or unsubstituted C ３ -C １０ Cycloalkenyl group, substituted or unsubstituted C １ -C １０ heterocycloalkenyl group, substituted or unsubstituted C ６ -C ６０ aryl group, substituted or unsubstituted C ６ -C ６０ aryloxy group, substituted or unsubstituted C ６ -C ６０ arylthio group, substituted or unsubstituted C １ -C ６０ a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a 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)(Q １ ), or -P(=O)(Q １ ) (Q ２ ) and D １ ~D ３ is deuterium, b1 to b3 and c1 to c3 are each independently an integer selected from 0 to 4; However, b1+c1, b2+c2, and b3+c3 are each 4, however, One of the c1 to c3 is 4 and the remaining two are 0, Two of the c1 to c3 are 4 and the remaining one is 0, or c1 to c3 are all 4, In the above Chemical Formula 1 【Chemistry 10】 is selected from groups represented by the following chemical formulas 2-1 to 2-6: [Chemical formula 2-1] 【Chemistry 11】 [Chemical formula 2-2] 【Chemistry 12】 [Chemical formula 2-3] 【Chemistry 13】 [Chemical formula 2-4] 【Chemistry 14】 [Chemical formula 2-5] 【Chemistry 15】 [Chemical formula 2-6] 【Chemistry 16】 In the chemical formulas 2-1 to 2-6, * and *' are bonding sites with adjacent atoms, The aforementioned substituted C ５ -C ６０ Carbocyclic groups, substituted C １ -C ６０ Heterocyclic groups, substituted C １ -C ６０ Alkyl groups, substituted C ２ -C ６０ Alkenyl groups, substituted C ２ -C ６０ Alkynyl group, substituted C １ -C ６０ Alkoxy groups, substituted C ３ -C １０ Cycloalkyl groups, substituted C １ -C １０ Heterocycloalkyl groups, substituted C ３ -C １０ Cycloalkenyl group, substituted C １ -C １０ Heterocycloalkenyl groups, substituted C ６ -C ６０ Aryl groups, substituted C ６ -C ６０ Aryloxy groups, substituted C ６ -C ６０ Arylthio groups, substituted C １ -C ６０ At least one of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituent of the substituted monovalent non-aromatic fused polycyclic heterocyclic group is Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C １ -C ６０ Alkyl group, C ２ -C ６０ Alkenyl group, C ２ -C ６０ Alkynyl group, C １ -C ６０ an alkoxy group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ３ -C １０ Cycloalkyl group, C １ -C １０ Heterocycloalkyl group, C ３ -C １０ Cycloalkenyl group, C １ -C １０ Heterocycloalkenyl group, C ６ -C ６０ Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ Arylthio group, C １ -C ６０ Heteroaryl group, 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 C) １ -C ６０ Alkyl group, C ２ -C ６０ Alkenyl group, C ２ -C ６０ Alkynyl group and C １ -C ６０ an alkoxy group; C ３ -C １０ Cycloalkyl group, C １ -C １０ Heterocycloalkyl group, C ３ -C １０ Cycloalkenyl group, C １ -C １０ Heterocycloalkenyl group, C ６ -C ６０ Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ Arylthio group, C １ -C ６０ Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C １ -C ６０ Alkyl group, C ２ -C ６０ Alkenyl group, C ２ -C ６０ Alkynyl group, C １ -C ６０ Alkoxy group, C ３ -C １０ Cycloalkyl group, C １ -C １０ Heterocycloalkyl group, C ３ -C １０ Cycloalkenyl group, C １ -C １０ Heterocycloalkenyl group, C ６ -C ６０ Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ Arylthio group, C １ -C ６０ Heteroaryl group, 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 C) ３ -C １０ Cycloalkyl group, C １ -C １０ Heterocycloalkyl group, C ３ -C １０ Cycloalkenyl group, C １ -C １０ Heterocycloalkenyl group, C ６ -C ６０ Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ Arylthio group, C １ -C ６０ Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; and -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 selected from The aforementioned Q １ ~Q ３ , Q １１ ~Q １３ , Q ２１ ~Q ２３ , and Q ３１ ~Q ３３ are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C １ -C ６０ Alkyl group, C ２ -C ６０ Alkenyl group, C ２ -C ６０ Alkynyl group, C １ -C ６０ Alkoxy group, C ３ -C １０ Cycloalkyl group, C １ -C １０ Heterocycloalkyl group, C ３ -C １０ Cycloalkenyl group, C １ -C １０ Heterocycloalkenyl group, C ６ -C ６０ Aryl group, C １ -C ６０ It is selected from the group consisting of heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic hetero-fused polycyclic groups, biphenylyl groups, and terphenylyl groups.

10. Said L １ ~ Said L ４ , and the L １１ ~ Said L １２ are, independently of one another, a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a spiro-fluorene-benzofluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, and a carbazolylene group; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C １ -C ２０ Alkyl group, C １ -C ２０ Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenylyl group, terphenylyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthyl group, anthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group , pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolylene group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, -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 a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a spiro-fluorene-benzofluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, and a carbazolylene group, Q ３１ ~The above Q ３３ are, independently of each other, C １ -C １０ Alkyl group, C １ -C １０ 10. The amine compound according to claim 9, wherein the aryl group is selected from the group consisting of an alkoxy group, a phenyl group, a phenyl group substituted with a C1-C10 alkyl group, a biphenylyl group, a terphenylyl group, and a naphthyl group.

11. The amine compound according to claim 9 , wherein a11 and a12 are 0.

12. The Ar １ ~ Ar ４ are independent of each other, Phenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, spiro-fluorene-benzofluorenyl group, benzofluorenyl group, dibenzofluorenyl group, benzonaphthofluorenyl group, pyrenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrrolyl group, thiophenyl group, furanyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group , isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrimidyl, quinolinyl, isoquinolinyl, benzoquinolinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, biphenylyl, and terphenylyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, methyl group, ethyl group, propyl group, isobutyl group, sec-butyl group, ter-butyl group, pentyl group, iso-amyl group, hexyl group, C １ -C ２０ Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, spiro-fluorene-benzofluorenyl group, benzofluorenyl group, dibenzofluorenyl group, benzonaphthofluorenyl group, pyrenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrrolyl group, thiophenyl group, furanyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, iso Thiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, isoindolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, isobenzothiazolyl group, benzoxa azolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzyl group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a spiro-fluorene-benzofluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a benzonaphthofluorenyl group, a pyrenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, or an isothiazolyl group, each of which is substituted with at least one group selected from the group consisting of a silolyl group, a biphenylyl group, and a terphenylyl group;10. The amine compound according to claim 9, wherein the amine is selected from the group consisting of oxazolyl, isoxazolyl, pyridinyl, pyrimidyl, quinolinyl, isoquinolinyl, benzoquinolinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, biphenylyl, and terphenylyl groups.

13. The Ar １ ~ Ar ４ are each independently a group represented by any one selected from the following Chemical Formulas 5-1 to 5-27: 【Chemistry 17】 [Chemistry 18] In the chemical formulas 5-1 to 5-27, Y ３１ is O, S, C (Z ３５ ) (Z ３６ ) or Si(Z ３７ ) (Z ３８ ) and Z ３１ ~Z ３８ are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C １ -C ２０ Alkyl group, C １ -C ２０ Alkoxy group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, anthracenyl group, phenanthrenyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxa a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, or an azacarbazolyl group; e3 is an integer from 0 to 3, e4 is an integer from 0 to 4, e5 is an integer from 0 to 5, e6 is an integer from 0 to 6, e7 is an integer from 0 to 7, e9 is an integer from 0 to 9, * indicates a bonding site with an adjacent atom.

14. 10. The amine compound according to claim 9, wherein Ar1 to Ar4 do not contain an amino group.

15. The R １ ~ The above R ３ are independent of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, methyl group, ethyl group, propyl group, isobutyl group, sec-butyl group, ter-butyl group, C １ -C ２０ Alkoxy groups, cyclopentyl groups, cyclohexyl groups, phenyl groups, naphthyl groups, fluorenyl groups, carbazolyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, biphenylyl groups, and terphenylyl groups; and a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a ter-butyl group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenylyl group, a terphenylyl group, a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a ter-butyl group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenylyl group, a terphenylyl group, a C １ -C ２０ 10. The amine compound of claim 9, wherein the aryl group is selected from the group consisting of alkoxy, cyclopentyl, cyclohexyl, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, biphenylyl, and terphenylyl.

16. The R １ ~ The above R ３ and at least one of is hydrogen. Compound.

17. The amine compound represented by the formula 1 is selected from the following compounds 1 to 192: 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 。

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