Heterocyclic compounds, organic light-emitting devices containing the same, and electronic devices

Abstract

The present invention provides heterocyclic compounds, organic light-emitting devices containing the same, and electronic devices. [Solution] A heterocyclic compound represented by the following chemical formula 1, an organic light-emitting element containing the same, and an electronic device: JPEG2026082774000158.jpg82170 For a description of the substituents of the above chemical formula 1, please refer to the description of the invention.

Description

[Technical Field]

[0001] The present invention relates to heterocyclic compounds, organic light-emitting devices containing the same, and electronic devices. [Background technology]

[0002] Organic light-emitting devices are self-emitting elements that excel in viewing angle, response time, brightness, driving voltage, and response speed, and can be made multi-colored.

[0003] For example, an organic light-emitting device includes an anode, a cathode, and an organic layer interposed between the anode and the cathode, which includes a light-emitting layer. A hole transport region is provided between the anode and the light-emitting layer, and an electron transport region is provided between the light-emitting layer and the cathode. Holes injected from the anode move to the light-emitting layer via the hole transport region, and electrons injected from the cathode move to the light-emitting layer via the electron transport region. The holes and electrons recombine in the light-emitting layer region to generate an exciton. Light is generated as the exciton changes from an excited state to a ground state. [Overview of the project] [Problems that the invention aims to solve]

[0004] The problem that this invention aims to solve is to provide a heterocyclic compound, an organic light-emitting device containing the same, and an electronic device. [Means for solving the problem]

[0005] In one aspect, a heterocyclic compound represented by the following chemical formula 1 is provided: [ka]

[0006] In the aforementioned chemical formula 1, Y 11 and Y 12are, independently of one another, a single bond, O, S, Se, N(Ar3), N(R1), C(R1)(R2), Si(R1)(R2), Ge(R1)(R2), B(R1), P(R1), P(=O)(R1), S(=O)2, or C(=O), Y 21 and Y 22 are, independently of one another, a single bond, O, S, Se, N(Ar4), N(R3), C(R3)(R4), Si(R3)(R4), Ge(R3)(R4), B(R3), P(R3), P(=O)(R3), S(=O)2, or C(=O), Ar1 to Ar4 are, independently of one another, a group represented by the following Chemical Formula 2,

Chem.

[0007] In the above Chemical Formulas 1 and 2, CY 11 ~CY 13 、CY 21 ~CY 23 and CY3 to CY6 are, independently of one another, a C5-C 30 carbocyclic group or a substituted or unsubstituted C1-C 30 heterocyclic group,

Chem.

[0008] In other aspects, an organic light-emitting device comprising the heterocyclic compound is provided.

[0009] In other aspects, an electronic device comprising the heterocyclic compound is provided. [Effects of the Invention]

[0010] Since the heterocyclic compound has excellent luminescence and charge mobility characteristics, an electronic element employing the heterocyclic compound, such as an organic light-emitting element, can have characteristics of low drive voltage, high efficiency, and long lifespan. Therefore, a high-quality organic light-emitting element can be realized using the heterocyclic compound. Furthermore, a high-quality electronic device can be realized using the organic light-emitting element. [Brief explanation of the drawing]

[0011] [Figure 1] This is a schematic cross-sectional view showing an organic light-emitting element according to one embodiment. [Figure 2] This is a schematic diagram showing the energy transition of an organic light-emitting element according to one embodiment. [Figure 3] This is a schematic diagram showing the energy transition of an organic light-emitting element according to one embodiment. [Figure 4] This is a schematic diagram showing the energy transition of an organic light-emitting element according to one embodiment. [Figure 5] This is a schematic diagram showing the energy transition of an organic light-emitting element according to one embodiment. [Figure 6] This is a schematic diagram showing the energy transition of an organic light-emitting element according to one embodiment. [Modes for carrying out the invention]

[0012] A heterocyclic compound according to one embodiment is represented by the following chemical formula 1: [ka]

[0013] In the above chemical formula 1, Y 11 and Y 12 These are, independently of each other, single bonds, O, S, Se, N(Ar3), N(R1), C(R1)(R2), Si(R1)(R2), Ge(R1)(R2), B(R1), P(R1), P(=O)(R1), S(=O)2, or C(=O).

[0014] In the above chemical formula 1, Y 21 and Y 22 These are, independently of each other, single bonds, O, S, Se, N(Ar4), N(R3), C(R3)(R4), Si(R3)(R4), Ge(R3)(R4), B(R3), P(R3), P(=O)(R3), S(=O)2, or C(=O).

[0015] According to one embodiment, Y 11 and Y 21 These are O, S, or Se, independently of each other.

[0016] According to one embodiment, Y 12 and Y 22 These are, independently of each other, O, S, Se, N(Ar3), N(R1), C(R1)(R2), or Si(R1)(R2).

[0017] In the aforementioned chemical formula 1, Ar1 to Ar4 are groups that are independently represented by the following chemical formula 2.

[0018] [ka]

[0019] In the above chemical formulas 1 and 2, CY 11 ~CY 13 CY 21 ~CY 23 And CY3~CY6 are independent of each other, C5-C 30 A carbocyclic group or a substituted or unsubstituted C1-C 30 It is a heterocyclic group.

[0020] In the aforementioned chemical formula 2, [ka] This indicates a single bond or a double bond.

[0021] In the above chemical formula 2, * represents a bonding site with an adjacent atom.

[0022] According to one embodiment, the CY 11 ~CY 13 CY 21 ~CY 23 And CY3~CY6 are, independently of each other, i) a first ring, ii) a second ring, iii) a condensed ring formed by the fusion of two or more first rings, iv) a condensed ring formed by the fusion of two or more second rings, or v) a condensed ring formed by the fusion of one or more first rings and one or more second rings. The first ring is a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, an thiazole group, an isothiazole group, an thiadiazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, or a triazalole group. The second ring is an adamantane group, norbornene group, bicyclo[1.1.1]pentane group, bicyclo[2.1.1]hexane group, bicyclo[2.2.1]heptane group (norbornane group), bicyclo[2.2.2]octane group, cyclohexane group, cyclohexene group, benzene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, or triazine group.

[0023] According to one embodiment, CY 11 ~CY 13 CY 21 ~CY 23 And CY3~CY6 are independent of each other, C6-C 30 Aromatic carbon ring group or C1-C 30 It is an aromatic heterocyclic group.

[0024] According to one embodiment, CY 11 ~CY 13 CY 21 ~CY 23And CY3~CY6 are, independently of each other, a benzene group, a naphthalene group, anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilol group, a benzobolol group, a benzophosphole group, a benzoselenophene group, a benzogermol group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, a dibenzosilol group, a dibenzobolol group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermol group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, and azabenzosilol Group, azabenzobolol group, azabenzophosphorus group, azabenzoselenophene group, azabenzogermol group, azadibenzothiophene group, azadibenzofuran group, azacarbazole group, azafluorene group, azadibenzosilol group, azadibenzobolol group, azadibenzophosphorus group, azadibenzoselenophene group, azadibenzogermol group, azadibenzothiophene 5-oxide group, aza-9 The group is either H-fluoren-9-one, azadibenzothiophene 5,5-dioxide, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, phenanthroline, 5,6,7,8-tetrahydroisoquinoline, 5,6,7,8-tetrahydroquinoline, adamantane, norbornane, or norbornene.

[0025] According to one embodiment, CY 11 ~CY 13 CY 21 ~CY 23And CY3 to CY6 are, independently of each other, a benzene group, a naphthalene group, a phenanthrene group, a fluorene group, a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilol group, a dibenzobolol group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermol group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, or a dibenzothiophene 5,5-dioxide group.

[0026] According to one embodiment, CY 11 CY 12 CY 21 CY 22 And CY3 to CY6 are, independently of each other, a benzene group, a naphthalene group, a phenanthrene group, a fluorene group, a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, or a dibenzosilole group.

[0027] According to one embodiment, CY 13 and CY 23 These are, independently of each other, a benzene group, a naphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, or a quinazoline group.

[0028] According to one embodiment, the group represented by chemical formula 2 is the group represented by the following chemical formula 2A: [ka]

[0029] In the aforementioned chemical formula 2A, X 41 is C(R 41 ) or N, X 42 is C(R 42 ) or N, X 43 is C(R43 ) or N, X 51 is C(R 51 ) or N, X 52 is C(R 52 ) or N, X 53 is C(R 53 ) or N, X 54 is C(R 54 ) or N, X 55 is C(R 55 ) or N, X 61 is C(R 61 ) or N, X 62 is C(R 62 ) or N, X 63 is C(R 63 ) or N, X 64 is C(R 64 ) or N, X 65 is C(R 65 ) or N, R 41 ~R 43 The explanations relating to R are independent of each other. 40 This is similar to the explanation regarding the above, R 51 ~R 55 The explanations relating to R are independent of each other. 50 This is similar to the explanation regarding the above, R 61 ~R 65 The explanations relating to R are independent of each other. 50 This is similar to the explanation regarding the above, * indicates a bonding site with an adjacent atom.

[0030] According to one embodiment, the group represented by chemical formula 2 is the group represented by the following chemical formula 2A-1.

[0031] [ka]

[0032] In the aforementioned chemical formula 2A-1, R 41 ~R 43The explanations relating to R are independent of each other. 40 This is similar to the explanation regarding the above, R 51 ~R 55 The explanations relating to R are independent of each other. 50 This is similar to the explanation regarding the above, R 61 ~R 65 The explanations relating to R are independent of each other. 50 This is similar to the explanation regarding the above, * indicates a bonding site with an adjacent atom.

[0033] In the above chemical formulas 1 and 2, R1 to R4, R 10 , R 20 , R 30 , R 40 , R 50 and R 60 These are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, and substituted or unsubstituted C1-C 60 Alkyl alkyl groups, substituted or unsubstituted C2-C 60 Alkenyl group, substituted or unsubstituted C2-C 60 Alkynyl group, substituted or unsubstituted C1-C 60 Alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C1-C 10 Heterocycloalkenyl group, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C7-C 60 Alkylaryl group, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio group, substituted or unsubstituted C1-C 60 Heteroaryl group, substituted or unsubstituted C2-C 60 Alkyl heteroaryl group, substituted or unsubstituted C1-C 60Heteroaryloxy group, substituted or unsubstituted C1-C 60 These are heteroarylthio groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic groups, -N(Q1)(Q2), -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -B(Q1)(Q2), -P(Q1)(Q2), -P(=O)(Q1)(Q2), -P(=S)(Q1)(Q2), or -P(=S)(Q1)(Q2).

[0034] According to one embodiment, R1 to R4, R 10 , R 20 , R 30 , R 40 , R 50 and R 60 They are independent of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, -SF5, C1-C 20 Alkyl group, or C1-C 20 Alkoxy group; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl group, deuterium-containing C1-C 20 Alkyl alkyl groups, C1-C fluoride 20 Alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norborneyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptyl group (norbornanyl group), bicyclo[2.2.2]octyl group, (C1-C 20 Alkyl)cyclopentyl group, (C1-C20 Alkyl)cyclohexyl group, (C1-C 20 Alkyl)cycloheptyl group, (C1-C 20 Alkyl)cyclooctyl group, (C1-C 20 Alkyl)adamantanyl group, (C1-C 20 Alkyl)norborneyl group, (C1-C 20 Alkyl)cyclopentenyl group, (C1-C 20 Alkyl)cyclohexenyl group, (C1-C 20 Alkyl)cycloheptenyl group, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl group, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl group, (C1-C 20 Alkyl)bicyclo[2.2.1]heptyl group, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl group, siloranyl group, phenyl group, (C1-C 20 C1-C substituted with alkyl)phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, 1,2,3,4-tetrahydronaphthyl groups, pyridinyl groups, pyrimidinyl groups, or any combination thereof. 20 Alkyl or C1-C 20 Alkoxy group; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl group, deuterium-containing C1-C 20 Alkyl alkyl groups, C1-C fluoride 20 Alkyl alkyl group, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norborneyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptyl group, bicyclo[2.2.2]octyl group, (C1-C 20Alkyl)cyclopentyl group, (C1-C 20 Alkyl)cyclohexyl group, (C1-C 20 Alkyl)cycloheptyl group, (C1-C 20 Alkyl)cyclooctyl group, (C1-C 20 Alkyl)adamantanyl group, (C1-C 20 Alkyl)norborneyl group, (C1-C 20 Alkyl)cyclopentenyl group, (C1-C 20 Alkyl)cyclohexenyl group, (C1-C 20 Alkyl)cycloheptenyl group, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl group, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl group, (C1-C 20 Alkyl)bicyclo[2.2.1]heptyl group, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl group, siloranyl group, phenyl group, (C1-C 20Alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2,3,4-tetrahydronaphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl 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, pyridadinyl group, isoindolyl group, indolyl group, indazolyl group, prinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolyl group, synnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, ben Zooxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, or any combination thereof, substituted or unsubstituted, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norborneyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptyl group, bicyclo[2.2.2]octyl group, siloranyl group, phenyl group, (C1-C 20Alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2,3,4-tetrahydronaphthyl group, fluorenyl group, phenantrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyridinyl group, pyrimidinyl group, pyridadinyl group, isoindolyl group, indolyl group, indazolyl group, prinyl group, quinolinyl group, isoquinolinyl group, benzox Norinyl group, quinoxalinyl group, quinazolinyl group, synnorinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group, or azadibenzothiophenyl group; or -N(Q1)(Q2), -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -B(Q1)(Q2), -P(Q1)(Q2), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2);

[0035] According to one embodiment, R1 to R4, R 10 , R 20 , R 30 , R 40 , R 50 and R 60 These are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, or C1-C 60 Alkoxy group; or It is a group represented by one of the following chemical formulas: 9-1 to 9-61, 9-201 to 9-244, 10-1 to 10-154, and 10-201 to 10-350. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0036] In the above chemical formulas 9-1 to 9-61, 9-201 to 9-244, 10-1 to 10-154, and 10-201 to 10-350, * represents a bonding site with an adjacent atom, Ph represents a phenyl group, TMS represents a trimethylsilyl group, and TMG represents a trimethylgermyl group.

[0037] According to one embodiment, R1 to R4, R 10 , R 20 , R 30 , R 40 , R 50 and R 60 They are independent of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, or C1-C 60 Alkoxy group; or A group represented by any one of the chemical formulas 9-1 to 9-61, 9-201 to 9-244, 10-1 to 10-154, and 10-201 to 10-350.

[0038] According to one embodiment, b30 R 30 At least one of them is -F, -Cl, -Br, -I, -SF5, a cyano group, or a substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C1-C 60 It is a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group.

[0039] According to one embodiment, b30 R 30 At least one of them is a substituted or non-substituted C1-C 60 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C1-C 60 It is a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group.

[0040] According to one embodiment, b30 R30 At least one of the following is -F, -Cl, -Br, -I, -SF5, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, 2-methylbutyl group, sec-pentyl group, tert-pentyl group, neo-pentyl group, 3-pentyl group, 3-methyl-2-butyl group, phenyl group, biphenyl group, C1-C 20 It is an alkylphenyl group or a naphthyl group.

[0041] In the aforementioned chemical formulas 1 and 2, b11-b13, b21-b23, b30, b40, b50, and b60 are independently 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14.

[0042] According to one embodiment, b11-b13, b21-b23, b30, b40, b50, and b60 are independently 1, 2, 3, 4, 5, 6, 7, or 8.

[0043] According to one embodiment, b11, b12, b21, and b22 are independently 1, 2, 3, or 4.

[0044] According to one embodiment, b13 and b23 are each 1.

[0045] According to one embodiment, b30 is 1, 2, or 3.

[0046] In the above chemical formulas 1 and 2, R1 to R4, R 10 , R 20 , R 30 , R 40 , R 50 and R 60 Two or more adjacent elements are optionally joined to each other, resulting in a substitution or non-substitution of C5-C. 30 Carbon ring group or C1-C 30 It can form heterocyclic groups.

[0047] According to one embodiment, the heterocyclic compound is represented by the following chemical formula 11: [ka]

[0048] In the aforementioned chemical formula 11, Y 11 , Y 12 , Y 21 , Y 22 The descriptions relating to Ar1 and Ar2 are the same as those described in this specification. X 11 is C(R 11 ) or N, X 12 is C(R 12 ) or N, X 13 is C(R 13 ) or N, X 14 is C(R 14 ) or N, X 15 is C(R 15 ) or N, X 16 is C(R 16 ) or N, X 17 is C(R 17 ) or N, X 18 is C(R 18 ) or N, X 19 is C(R 19 ) or N, X 21 is C(R 21 ) or N, X 22 is C(R 22 ) or N, X 23 is C(R 23 ) or N, X 24 is C(R 24 ) or N, X 25 is C(R 25 ) or N, X 26 is C(R 26 ) or N, X 27 is C(R 27 ) or N, X 28 is C(R 28 ) or N, X 29 is C(R 29) or N, X 31 is C(R 31 ) or N, X 32 is C(R 32 ) or N, X 33 is C(R 33 ) or N, R 11 ~R 19 The explanations relating to R are independent of each other. 10 This is similar to the explanation regarding the above, R 21 ~R 29 The explanations relating to R are independent of each other. 20 This is similar to the explanation regarding the above, R 31 ~R 33 The explanations relating to R are independent of each other. 30 This is similar to the explanation given earlier.

[0049] According to one embodiment, the heterocyclic compound is represented by the following chemical formula 21: [ka]

[0050] In the aforementioned chemical formula 21, Y 11 , Y 12 , Y 21 , Y 22 The descriptions relating to Ar1 and Ar2 are the same as those described in this specification. R 11 ~R 19 The explanations relating to R are independent of each other. 10 This is similar to the explanation regarding the above, R 21 ~R 29 The explanations relating to R are independent of each other. 20 This is similar to the explanation regarding the above, R 31 ~R 33 The explanations relating to R are independent of each other. 30 This is similar to the explanation provided.

[0051] According to one embodiment, the heterocyclic compound is represented by the following chemical formula 31: [ka]

[0052] In the aforementioned chemical formula 31, Y 11 , Y 12 , Y 21 , Y 22 The descriptions relating to Ar1 and Ar2 are the same as those described in this specification. R 11 ~R 19 The explanations relating to R are independent of each other. 10 This is similar to the explanation regarding the above, R 21 ~R 29 The explanations relating to R are independent of each other. 20 This is similar to the explanation regarding the above, R 31 ~R 33 The explanations relating to R are independent of each other. 30 This is similar to the explanation regarding the above, R 41 ~R 43 and R 41a ~R 43a The explanations relating to R are independent of each other. 40 This is similar to the explanation regarding the above, R 51 ~R 55 and R 51a ~R 55a The explanations relating to R are independent of each other. 50 This is similar to the explanation regarding the above, R 61 ~R 65 and R 61a ~R 65a The explanations relating to R are independent of each other. 60 This is similar to the explanation provided.

[0053] According to one embodiment, in the chemical formulas 11, 21, and 31, R 31 ~R 33 At least one of them is -F, -Cl, -Br, -I, -SF5, a cyano group, or a substituted or unsubstituted C1-C60 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C1-C 60 It is a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group.

[0054] According to one embodiment, in the chemical formulas 11, 21, and 31, R 31 ~R 33 At least one of them is a substituted or non-substituted C1-C 60 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C1-C 60 It is a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group.

[0055] According to one embodiment, in the chemical formulas 11, 21, and 31, R 32 However, -F, -Cl, -Br, -I, -SF5, cyano group, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C1-C 60 It is a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group.

[0056] According to one embodiment, in the chemical formulas 11, 21, and 31, R 32However, -F, -Cl, -Br, -I, -SF5, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, 2-methylbutyl group, sec-pentyl group, tert-pentyl group, neo-pentyl group, 3-pentyl group, 3-methyl-2-butyl group, phenyl group, biphenyl group, C1-C 20 It is an alkylphenyl group or a naphthyl group.

[0057] According to one embodiment, in the chemical formulas 11, 21, and 31, R 31 and R 33 These are, independently of each other, hydrogen or deuterium.

[0058] According to one embodiment, the heterocyclic compound may have a symmetrical or asymmetrical structure.

[0059] For example, the heterocyclic compound may have a symmetrical structure.

[0060] As another example, the heterocyclic compound may have an asymmetric structure.

[0061] In this specification, the substituted C5-C 30 Carbocyclic group, substituted C1-C 30 Heterocyclic group, substituted C1-C 60 Alkyl alkyl group, substituted C2-C 60 Alkenyl group, substituted C2-C 60 Alkynyl group, substituted C1-C 60 Alkoxy group, substituted C3-C 10 Cycloalkyl groups, substituted C1-C 10 Heterocycloalkyl groups, substituted C3-C 10 Cycloalkenyl group, substituted C1-C 10 Heterocycloalkenyl group, substituted C6-C 60 Aryl group, substituted C6-C 60 Aryloxy group, substituted C6-C 60Arylthio group, substituted C1-C 60 heteroaryl group, substituted C1-C 60 Heteroaryloxy group, substituted C1-C 60 The substituents of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic heterocondensed polycyclic group are Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, or C1-C 60 Alkoxy group; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q 11 )(Q 12 ), -Si(Q 11 )(Q 12 )(Q 13 ), -Ge(Q 11 )(Q 12 )(Q 13 ), -C(=O)(Q 11 ), -S(=O)(Q 11 ), -S(=O)2(Q 11 ), -B(Q 11 )(Q12 ), -P(Q 11 )(Q 12 ), -P(=O)(Q 11 )(Q 12 ), -P(=S)(Q 11 )(Q 12 ), or any combination thereof, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, or C1-C 60 Alkoxy group; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q 21 )(Q 22 ), -Si(Q 21 )(Q 22 )(Q 23 ), -Ge(Q 21 )(Q 22 )(Q 23 ), -C(=O)(Q 21 ), -S(=O)(Q 21 ), -S(=O)2(Q 21 ), -B(Q 21 )(Q 22 ), -P(Q 21 )(Q 22), -P(=O)(Q 21 )(Q 22 ), -P(=S)(Q 21 )(Q 22 ), or any combination thereof, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, or monovalent non-aromatic heterocondensed polycyclic groups; -N(Q 31 )(Q 32 ), -Si(Q 31 )(Q 32 )(Q 33 ), -Ge(Q 31 )(Q 32 )(Q 33 ), -C(=O)(Q 31 ), -S(=O)(Q 31 ), -S(=O)2(Q 31 ), -B(Q 31 )(Q 32 ), -P(Q 31 )(Q 32 ), -P(=O)(Q 31 )(Q 32 ), or -P(Q 31 )(Q 32 );or Any combination of those;

[0062] In this specification, Q1 to Q3, Q 11 ~Q 13 Q 21 ~Q 23 and Q 31 ~Q 33These are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic heterocondensed polycyclic group; or Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, C1-C 60 Alkyl alkyl group, C6-C 60 Aryl group, C1-C 60 C1-C substituted with heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic heterocondensed polycyclic groups, or any combination thereof. 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 It is a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic heterocondensed polycyclic group.

[0063] For example, in this specification, Q1 to Q3, Q 11 ~Q 13 Q 21 ~Q 23 and Q 31 ~Q 33 They are independent of each other, -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or Deuterium, C1-C 10 n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, phenyl group, biphenyl group, or naphthyl group, substituted or unsubstituted with alkyl groups, phenyl groups, or any combination thereof;

[0064] According to one embodiment, the heterocyclic compound is at least one of the following compounds 1 to 510: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

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[0065] The heterocyclic compound represented by chemical formula 1 contains a structure that satisfies the structure of chemical formula 1, wherein Ar1 and Ar2 are groups represented by chemical formula 2, respectively. Due to such a structure, the heterocyclic compound represented by chemical formula 1 exhibits excellent luminescence properties, and can particularly exhibit deep blue light at short wavelengths.

[0066] Although not limited by any particular theory, the heterocyclic compound, by having a skeleton represented by chemical formula 1, exhibits increased molecular rigidity and a small singlet-triplet energy difference, thereby allowing it to exhibit advantageous properties such as a narrow full width at half maximum (FWHM), a small Stokes shift, and / or a fast delayed fluorescence excitation time (tau). Furthermore, as mentioned above, the inclusion of a substituent in a bulky structure in which the group represented by chemical formula 2, i.e., CY4-CY6, is linked in the ortho position, results in a high S1 energy level, suppressed intermolecular interactions, high color purity, and high photo-orientation. As a result, when the heterocyclic compound is used as a luminescent material, Dexter energy transfer is suppressed, and it can exhibit excellent lifetime characteristics.

[0067] Therefore, an electronic device containing the heterocyclic compound represented by chemical formula 1, such as an organic light-emitting device, can exhibit high efficiency and long lifespan.

[0068] The HOMO, LUMO, S1, and T1 energy levels of some heterocyclic compounds represented by the aforementioned chemical formula 1 were evaluated using the Gaussian 09 program with molecular structure optimization based on density functional theory (DFT) using B3LYP. The results are shown in Table 1 below.

[0069] [Table 1] [ka]

[0070] From Table 1, it can be confirmed that the heterocyclic compound represented by chemical formula 1 has electrical properties suitable for use as an electronic element, such as a dopant (e.g., emitter or sensor) in an organic light-emitting device.

[0071] According to one embodiment, the full width at half maximum (FWHM) of the emission peak in the emission spectrum or electroluminescence spectrum of the heterocyclic compound is 60 nm or less. For example, the full width at half maximum (FWHM) of the emission peak in the emission spectrum or electroluminescence spectrum of the heterocyclic compound is in the range of 5 nm to 50 nm, 7 nm to 40 nm, or 10 nm to 30 nm.

[0072] The method for synthesizing the heterocyclic compound represented by the chemical formula 1 can be understood by those skilled in the art by referring to the synthesis examples described later.

[0073] The method for confirming the structure of the heterocyclic compound represented by the chemical formula 1 is not particularly limited. According to one embodiment, the structure of the heterocyclic compound can be confirmed by known methods (e.g., NMR, LC-MS, etc.).

[0074] [Organic light-emitting element] In other aspects, an organic light-emitting device comprising the heterocyclic compound is provided.

[0075] According to one embodiment, the organic light-emitting element includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, which includes a light-emitting layer. The organic layer contains a heterocyclic compound represented by the chemical formula 1.

[0076] According to one embodiment, the light-emitting layer contains the heterocyclic compound.

[0077] According to one embodiment, the light-emitting layer includes a host and an emitter, and the emitter includes the heterocyclic compound.

[0078] According to one embodiment, the host content in the light-emitting layer is greater than the heterocyclic compound content, based on weight.

[0079] According to one embodiment, the light-emitting layer may further include a sensor.

[0080] According to one embodiment, the sensor includes a phosphorescent compound, a delayed-fluorescence compound, or any combination thereof.

[0081] For a detailed description of the host, emitter, and sensor mentioned above, please refer to the information provided herein.

[0082] The aforementioned organic light-emitting device, by comprising a light-emitting layer containing a heterocyclic compound represented by the chemical formula 1 described above, can have a relatively narrow EL spectral emission peak full width at half maximum (FWHM), excellent efficiency, and lifetime characteristics.

[0083] According to one embodiment, the heterocyclic compound acts as a dopant (e.g., an emitter or a sensor) in the light-emitting layer, and the light-emitting layer may further contain a host (i.e., the content of the heterocyclic compound represented by chemical formula 1 in the light-emitting layer is less than the content of the host).

[0084] According to one embodiment, the light-emitting layer can emit blue light. For example, the light-emitting layer can emit blue light with a maximum emission wavelength of 410 nm to 490 nm.

[0085] According to one embodiment, the light-emitting layer can emit deep blue light with a maximum emission wavelength of 410 nm to 450 nm. For example, the light-emitting layer can emit deep blue light with a maximum emission wavelength of 410 nm to 445 nm.

[0086] In this specification, "(The luminescent layer) contains one or more heterocyclic compounds" is also interpreted as "(The luminescent layer) contains one heterocyclic compound belonging to the category of chemical formula 1, or two or more different heterocyclic compounds belonging to the category of chemical formula 1."

[0087] For example, the light-emitting layer may contain only compound 1 as the heterocyclic compound. In this case, compound 1 may be present in the light-emitting layer of the organic light-emitting element. Alternatively, the light-emitting layer may contain compound 1 and compound 2 as the heterocyclic compound.

[0088] [Explanation related to Figure 1] Figure 1 schematically shows a cross-sectional view of an organic light-emitting element 10 according to one embodiment. The structure and manufacturing method of the organic light-emitting element according to one embodiment will be described below with reference to Figure 1.

[0089] The organic light-emitting element 10 in Figure 1 includes a first electrode 11, a second electrode 19 facing the first electrode 11, and an organic layer 15 disposed between the first electrode 11 and the second electrode 19.

[0090] The organic layer 15 includes a light-emitting layer, a hole transport region is located between the first electrode 11 and the light-emitting layer, and an electron transport region is located between the light-emitting layer and the second electrode 19.

[0091] A substrate may be further placed below the first electrode 11 or above the second electrode 19. While a substrate commonly used in organic light-emitting devices can be used as the substrate, a glass substrate or a transparent plastic substrate with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water repellency can also be used.

[0092] [First electrode 11] The first electrode 11 is formed, for example, by providing the material for the first electrode on the upper part of the substrate using a vapor deposition method or a sputtering method. The first electrode 11 also serves as the anode. The material for the first electrode is selected from materials having a high work function so that hole injection is easily performed.

[0093] The first electrode 11 is a reflective electrode, a semi-permeable electrode, or a transmissive electrode. To form a transmissive first electrode 11, the material for the first electrode is selected from, but is not limited to, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof. Alternatively, to form a semi-permeable or reflective first electrode 110, the material for the first electrode is 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.

[0094] The first electrode 11 may have a single layer or a multilayer structure including two or more layers.

[0095] [Luminous layer] The light-emitting layer may contain the heterocyclic compound.

[0096] The thickness of the light-emitting layer is approximately 100 Å to approximately 1,000 Å, for example, approximately 200 Å to approximately 600 Å. When the thickness of the light-emitting layer satisfies the above range, excellent light-emitting characteristics can be achieved without a substantial increase in driving voltage.

[0097] [Explanation related to Figure 2] According to one embodiment, the heterocyclic compound may be a fluorescent emitter.

[0098] According to one embodiment, the light-emitting layer may further contain a host (hereinafter referred to as "host A," which is not identical to the heterocyclic compound). Host A is understood with reference to, but is not limited to, the host materials described later. Host A is also a fluorescent host.

[0099] Referring to Figure 2, the energy transition in one embodiment is described as follows.

[0100] Singlet excitons are formed in host A within the light-emitting layer, and these singlet excitons are transferred to the fluorescent emitter via Ferster energy transfer (or Ferster resonance energy transfer: FRET).

[0101] Since only 25% of the excitons formed in host A are singlet excitons, the efficiency of the organic light-emitting device can be further improved by enabling the 75% of triplet excitons formed in host A to fuse with each other and be converted into singlet excitons. In other words, the efficiency of the organic light-emitting device can be further improved using the triplet-triplet fusion (TTF) mechanism.

[0102] According to one embodiment, the proportion of the luminescent component emitted from the heterocyclic compound among the total luminescent components emitted from the luminescent layer is 80% or more, for example, 90% or more. For example, the proportion of the luminescent component emitted from the heterocyclic compound among the total luminescent components emitted from the luminescent layer is 95% or more.

[0103] Here, the heterocyclic compound emits fluorescence, while the host does not emit light.

[0104] According to one embodiment, when the light-emitting layer further contains host A in addition to the heterocyclic compound, the content of the heterocyclic compound is 50 parts by weight or less per 100 parts by weight of the light-emitting layer, for example, 30 parts by weight or less, and the content of host A in the light-emitting layer is 50 parts by weight or more per 100 parts by weight of the light-emitting layer, for example, 70 parts by weight or more, but is not limited thereto.

[0105] According to one embodiment, if the light-emitting layer further contains host A in addition to the heterocyclic compound, then host A and the heterocyclic compound can satisfy the following condition A: <Condition A> E(H A ) S1 >E S1 In the above condition A, E(H A ) S1 This is the lowest excitation singlet energy level of host A, E S1 This is the lowest singlet excitation energy level of the heterocyclic compound.

[0106] The aforementioned E(H A ) S1 and E S1 This was evaluated using the DFT method of a Gaussian program whose structure was optimized at the B3LYP / 6-31G(d,p) level.

[0107] [Explanation related to Figure 3] According to one embodiment, the heterocyclic compound may be a delayed fluorescence emitter.

[0108] According to one embodiment, the light-emitting layer may further contain a host (hereinafter referred to as "host B," and host B is not identical to the heterocyclic compound). Host B is understood with reference to, but is not limited to, the host materials described later.

[0109] Referring to Figure 3, the energy transition in one embodiment is described as follows.

[0110] 25% of the singlet excitons formed in host B within the light-emitting layer are transferred to the delayed fluorescence emitter via FRET. Additionally, 75% of the triplet excitons formed in host B within the light-emitting layer are transferred to the delayed fluorescence emitter via Dexter energy transfer. Of these, at least a portion of the singlet energy of the delayed fluorescence emitter is transferred to the triplet via intersystem crossing (ISC). The energy transferred to the triplet of the delayed fluorescence emitter can then undergo reverse intersystem crossing (RISC) back to the singlet. This allows for the transfer of both singlet and triplet excitons generated in the light-emitting layer to the heterocycle, resulting in an organic light-emitting device with improved efficiency.

[0111] Therefore, according to one embodiment, the proportion of the luminescent component emitted from the heterocyclic compound among the total luminescent components emitted from the luminescent layer is 80% or more, for example, 90% or more. For example, the proportion of the luminescent component emitted from the heterocyclic compound among the total luminescent components emitted from the luminescent layer is 95% or more.

[0112] Here, the heterocyclic compound emits fluorescence and / or delayed fluorescence, and the luminescence component of the heterocyclic compound is the sum of the immediate emission component and the RISC-mediated delayed fluorescence component of the heterocyclic compound. Furthermore, the host B does not emit light.

[0113] According to one embodiment, when the light-emitting layer further contains host B in addition to the heterocyclic compound, the content of the heterocyclic compound is 50 parts by weight or less per 100 parts by weight of the light-emitting layer, for example, 30 parts by weight or less, and the content of host B in the light-emitting layer is 50 parts by weight or more per 100 parts by weight of the light-emitting layer, for example, 70 parts by weight or more, but is not limited thereto.

[0114] According to one embodiment, if the light-emitting layer further contains host B in addition to the heterocyclic compound, the host B and the heterocyclic compound can satisfy the following condition B: <Condition B> E(H B ) S1 >E S1 In the above condition B, E(H B ) S1 This is the lowest excitation singlet energy level of host B, E S1 This is the lowest singlet excitation energy level of the heterocyclic compound.

[0115] The aforementioned E(H B ) S1 and E S1 This was evaluated using the DFT method of a Gaussian program whose structure was optimized at the B3LYP / 6-31G(d,p) level.

[0116] [Explanation related to Figure 4] According to one embodiment, the heterocyclic compound is used as a fluorescent emitter, and the light-emitting layer includes a sensorizer, specifically a delayed fluorescence sensorizer. According to a third embodiment, the light-emitting layer may further include a host (hereinafter referred to as "host C," where host C is not the same as the heterocyclic compound and the sensorizer) and a sensorizer (hereinafter referred to as "sensitizer A," where sensorizer A is not the same as host C and the heterocyclic compound). Host C and sensorizer A are understood with reference to, but are not limited to, the host material and sensorizer material described later.

[0117] According to one embodiment, the proportion of the luminescent component of the heterocyclic compound among the total luminescent components emitted from the luminescent layer is 80% or more, for example, 90% or more (as another example, 95% or more). For example, the heterocyclic compound can emit fluorescence. Furthermore, the host C and the sensor A do not emit light.

[0118] Referring to Figure 4, the energy transition in one embodiment is described as follows.

[0119] Singlet and triplet excitons are formed in host C in the light-emitting layer. The singlet and triplet excitons formed in host C are then transferred to sensorizer A, and subsequently transferred again to the heterocyclic compound via FRET. 25% of the singlet excitons formed in host C are transferred to sensorizer A via FRET, and the energy of the 75% of triplet excitons formed in host C is transferred to the singlet and triplet states of sensorizer A. Of these, at least a portion of the singlet energy of sensorizer A is transferred to the triplet state via ISC. The energy transferred to the triplet state of sensorizer A undergoes RISC to the singlet state, and then the singlet energy of sensorizer A is transferred to the heterocyclic compound via FRET.

[0120] This allows for the transfer of both singlet and triplet excitons generated in the light-emitting layer to the dopant (e.g., the emitter), resulting in an organic light-emitting device with improved efficiency. Furthermore, since an organic light-emitting device with significantly reduced energy loss is obtained, the lifetime characteristics of the organic light-emitting device can also be improved.

[0121] Referring to Figure 4, if the light-emitting layer further includes host C and sensor A in addition to the heterocyclic compound, then host C and sensor A can satisfy the following conditions C-1 and / or C-2: <Condition C-1> S1(H C )≧S1(S A ) <Condition C-2> S1(S A )≧S1(HC) In the above conditions C-1 and C-2, S1(H C ) is the lowest excitation singlet energy level of the host C, S1(S A ) is the lowest excitation singlet energy level of the aforementioned sensor A, S1(HC) is the lowest singlet excitation energy level of the heterocyclic compound.

[0122] The aforementioned S1(H C ), S1(S A ) and S1(HC) were evaluated using the DFT method of a Gaussian program whose structure was optimized at the B3LYP / 6-31G(d,p) level.

[0123] If the host C, the sensorizer A, and the heterocyclic compound satisfy the conditions C-1 and / or C-2, FRET from the sensorizer A to the heterocyclic compound can be promoted, thereby improving the luminescence efficiency of the organic light-emitting element.

[0124] [Explanation related to Figure 5] According to one embodiment, the heterocyclic compound is used as a fluorescent emitter, and the light-emitting layer may include a sensor, specifically a phosphorescent sensor.

[0125] According to one embodiment, the light-emitting layer may further include a host (hereinafter referred to as "host D," where host D is not the same as the heterocyclic compound and the sensorizer) and a sensorizer (hereinafter referred to as "sensitizer B," where sensorizer B is not the same as host D and the heterocyclic compound). Host D and sensorizer B are understood with reference to, but are not limited to, the host material and sensorizer material described later.

[0126] According to one embodiment, the proportion of the luminescent component of the heterocyclic compound among the total luminescent components emitted from the luminescent layer is 80% or more, for example, 90% or more (as another example, 95% or more). For example, the heterocyclic compound can emit fluorescence. Furthermore, the host and the sensorizer do not emit light.

[0127] Referring to Figure 5, the energy transition in one embodiment is described as follows.

[0128] 75% of the triplet excitons formed in host D in the light-emitting layer are transferred to sensorizer B via Dexter energy transfer, and the energy of the 25% of singlet excitons formed in host D is transferred to singlet and triplet states in sensorizer B. Of these, the energy transferred to the singlet state in sensorizer B undergoes ISC to the triplet state, and then the triplet energy of sensorizer B is transferred to the heterocyclic compound via FRET.

[0129] This allows for the transfer of both singlet and triplet excitons generated in the light-emitting layer to the dopant (e.g., the emitter), resulting in an organic light-emitting device with improved efficiency. Furthermore, since an organic light-emitting device with significantly reduced energy loss is obtained, the lifetime characteristics of the organic light-emitting device can also be improved.

[0130] According to one embodiment, if the light-emitting layer further comprises a host D and a sensor B in addition to the heterocyclic compound, the host D and the sensor B can satisfy the following conditions D-1 and / or D-2: <Condition D-1> T1(H D )≧T1(S B ) <Condition D-2> T1(S B )≧S1(HC) In the above conditions D-1 and D-2, T1(H D ) is the lowest excitation triplet energy level of the host D, T1(S B ) is the lowest excitation triplet energy level of the aforementioned sensor B, S1(HC) is the lowest singlet excitation energy level of the heterocyclic compound.

[0131] The aforementioned T1(H D ), T1(S B ) and S1(HC) were evaluated using the DFT method of a Gaussian program whose structure was optimized at the B3LYP / 6-31G(d,p) level.

[0132] If the host D, the sensorizer B, and the heterocyclic compound satisfy conditions D-1 and / or D-2, FRET from the sensorizer B to the heterocyclic compound can be promoted, thereby improving the luminescence efficiency of the organic light-emitting element.

[0133] According to one embodiment, the content of the sensor in the light-emitting layer is selected within the range of 5% to 50% by weight, specifically within the range of 10% to 30% by weight. When the above range is satisfied, effective energy transfer in the light-emitting layer can be achieved, thereby realizing a highly efficient and long-life organic light-emitting element.

[0134] According to one embodiment, the content of the heterocyclic compound in the light-emitting layer is selected from a range of 0.01% to 15% by weight, specifically from 0.05% to 3% by weight, and is not limited thereto.

[0135] According to one embodiment, the sensorizer and heterocyclic compound can further satisfy the following condition 5: <Condition 5> 0 μs <T decay (HC) < 5 μs In the aforementioned condition 5, T decay (HC) is the decay time of the heterocyclic compound.

[0136] The decay time of the heterocyclic compound is determined by the weight ratio of the host and heterocyclic compound contained in the light-emitting layer on the quartz substrate at 90:10. -7 These values ​​were calculated from the TRPL (Time-Resolved Photoluminescence) spectrum at room temperature for a 40 nm thick film (hereinafter referred to as "film (HC)") obtained by vacuum co-deposition at a Torr vacuum level.

[0137] [Explanation related to Figure 6] According to one embodiment, the heterocyclic compound is used as a delayed fluorescence emitter, and the light-emitting layer may include a sensor, specifically a delayed fluorescence sensor.

[0138] According to one embodiment, the light-emitting layer may further include a host (hereinafter referred to as "host E," where host E is not the same as the heterocyclic compound and the sensorizer) and a sensorizer (hereinafter referred to as "sensitizer C," where sensorizer C is not the same as host E and the heterocyclic compound). Host E and sensorizer C are understood with reference to, but are not limited to, the host material and sensorizer material described later.

[0139] According to one embodiment, the proportion of the luminescent component of the heterocyclic compound among the total luminescent components emitted from the luminescent layer is 80% or more, for example, 90% or more (as another example, 95% or more). For example, the heterocyclic compound can emit fluorescence and / or delayed fluorescence. Furthermore, the host E and the sensor C do not emit light.

[0140] Here, the heterocyclic compound emits fluorescence and / or delayed fluorescence, and the luminescence component of the heterocyclic compound is the sum of the immediate luminescence component of the heterocyclic compound and the RISC-mediated delayed fluorescence component of the heterocyclic compound.

[0141] Referring to Figure 6, the energy transition in one embodiment is described as follows.

[0142] 25% of the singlet excitons formed in the host E in the luminescent layer are transferred to the singlet state of the sensorizer C via FRET, and the energy of the 75% of the triplet excitons formed in the host E is transferred to the triplet state of the sensorizer C. Then, the singlet energy of the sensorizer C is again transferred to the heterocyclic compound via FRET, and the triplet energy of the sensorizer C is transferred to the heterocyclic compound via Dexter energy transfer. Of these, the energy transferred to the triplet state of the sensorizer C can undergo RISC to the singlet state. In the case of the sensorizer C, the energy of the triplet state formed in the sensorizer C is transferred in the reverse direction to the host E (triplet exciton distributing, TED), and then transferred again to the heterocyclic compound, allowing it to emit light via RISC.

[0143] This allows for the transfer of both singlet and triplet excitons generated in the light-emitting layer to the dopant (e.g., the emitter), resulting in an organic light-emitting device with improved efficiency. Furthermore, since an organic light-emitting device with significantly reduced energy loss is obtained, the lifetime characteristics of the organic light-emitting device can also be improved.

[0144] According to one embodiment, if the light-emitting layer further comprises a host E and a sensor C in addition to the heterocyclic compound, the host E and the sensor C can satisfy the following conditions E-1, E-2 and / or E-3: <Condition E-1> S1(H E )≧S1(S C ) <Condition E-2> S1(S C )≧S1(HC) <Condition E-3> T1(S C )≧T1(HC) In the above conditions E-1, E-2 and E-3, S1(H E ) is the lowest excitation singlet energy level of the host E, S1(S C) is the lowest excitation singlet energy level of the aforementioned sensor C, S1(HC) is the lowest singlet excitation energy level of the heterocyclic compound, T1(S C ) is the lowest excitation triplet energy level of the aforementioned sensor C, T1(HC) is the lowest excited triplet energy level of the heterocyclic compound.

[0145] The aforementioned S1(H E ), S1(S C ), S1(HC), T1(S C ) and T1(HC) were evaluated using the DFT method of a Gaussian program whose structure was optimized at the B3LYP / 6-31G(d,p) level.

[0146] If the host E, the sensorizer C, and the heterocyclic compound satisfy the conditions E-1, E-2, and / or E-3, then Dexter migration and FRET from the sensorizer C to the heterocyclic compound can be promoted, thereby improving the luminescence efficiency of the organic light-emitting element.

[0147] According to one embodiment, the content of the sensor C in the light-emitting layer is selected within the range of 5% to 50% by weight, specifically within the range of 10% to 30% by weight. When the above range is satisfied, effective energy transfer in the light-emitting layer can be achieved, thereby realizing a highly efficient and long-life organic light-emitting element.

[0148] According to one embodiment, the content of the heterocyclic compound in the light-emitting layer is selected from a range of 0.01% to 15% by weight, specifically from 0.05% to 3% by weight, and is not limited thereto.

[0149] [Host in the luminescent layer] According to one embodiment, the host does not contain metal atoms.

[0150] According to one embodiment, the host may contain at least one compound selected from fluorene-containing compounds, carbazole-containing compounds, dibenzofuran-containing compounds, dibenzothiophene-containing compounds, indenocarbazole-containing compounds, indolocarbazole-containing compounds, benzoflocarbazole-containing compounds, benzothienocarbazole-containing compounds, acridine-containing compounds, dihydroacridine-containing compounds, triindrobenzene-containing compounds, pyridine-containing compounds, pyrimidine-containing compounds, triazine-containing compounds, silicon-containing compounds, cyano group-containing compounds, phosphine oxide-containing compounds, sulfoxide-containing compounds, and sulfonyl-containing compounds.

[0151] For example, the host is a compound containing at least one carbazole ring and at least one cyano group, or a phosphine oxide-containing compound.

[0152] According to one embodiment, the host may consist of one type of host. When the host consists of one type of host, the one type of host is selected from a bipolar host, an electron-transporting host, and a hole-transporting host, which will be described later.

[0153] According to one embodiment, the host may be a mixture of two or more different hosts. For example, the host may be a mixture of an electron-transporting host and a hole-transporting host, a mixture of two different electron-transporting hosts, or a mixture of two different hole-transporting hosts. A description of the electron-transporting host and the hole-transporting host will be provided later.

[0154] According to one embodiment, the host may include an electron-transporting host containing at least one electron-transporting moisture, and a hole-transporting host that does not contain an electron-transporting moisture.

[0155] In this specification, electron-transporting moieties are selected from cyano groups, π-electron-deficient nitrogen-containing cyclic groups, and groups represented by one of the following chemical formulas: [ka]

[0156] In the above chemical formula, *, *', and *'' are bonding sites with any adjacent atom.

[0157] According to one embodiment, the electron-transporting host in the light-emitting layer may include at least one of a cyano group and a π-electron-deficient nitrogen-containing cyclic group.

[0158] According to one embodiment, the electron-transporting host in the light-emitting layer may contain at least one cyano group.

[0159] According to one embodiment, the electron-transporting host in the light-emitting layer may include at least one cyano group and at least one π-electron-deficient nitrogen-containing cyclic group.

[0160] According to one embodiment, the host comprises an electron-transporting host and a hole-transporting host, the electron-transporting host comprising at least one π-electron-deficient nitrogen-free cyclic group and at least one electron-transporting moisture, and the hole-transporting host comprising at least one π-electron-deficient nitrogen-free cyclic group and not comprising an electron-transporting moisture.

[0161] In this specification, "π-electron deficient nitrogen-containing cyclic group" refers to a cyclic group having at least one *-N=*' moiety, such as imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoli Selected from the following: ∫ group, sinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, and azacarbazole group; and a condensed ring of two or more of the π-electron-deficient nitrogen-containing cyclic groups.

[0162] On the other hand, the π-electron-deficient nitrogen-free cyclic groups include benzene, heptalene, indene, naphthalene, azulene, indacene, acenaphthylene, fluorene, spirobifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluorantene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentacene, hexacene, pentacene, rubicene, cologen, ovalene, pyrrole, and isoindole. The group is selected from, but is not limited to, a fused ring of two or more of the aforementioned π-electron-deficient nitrogen-free cyclic groups: a group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophenesulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzoflocarbazole group, a benzothienocarbazole group, and a triindrobenzene group; and two or more of the aforementioned π-electron-deficient nitrogen-free cyclic groups.

[0163] According to one embodiment, when the host is a mixture of an electron-transporting host and a hole-transporting host, the weight ratio of the electron-transporting host to the hole-transporting host is selected from the range of 1:9 to 9:1, for example, 2:8 to 8:2, as another example, 4:6 to 6:4, and as yet another example, 5:5. When the weight ratio of the electron-transporting host to the hole-transporting host satisfies the above range, a balance of hole and electron transport in the light-emitting layer can be achieved.

[0164] The host may contain at least one of the following: TPBi, TBADN, ADN (also known as "DNA"), CBP, CDBP, TCP, mCP, compound H50, and compound H51: [ka]

[0165] Alternatively, the host may further contain a compound represented by the following chemical formula 301: [ka]

[0166] In the aforementioned chemical formula 301, Ar 111 and Ar 112 They are independent of each other, Phenylene group, naphthylene group, phenantrenylene group, and pyrenylene group; and A phenylene group, naphthylene group, phenantrenylene group, and pyrenylene group, selected from those substituted with one or more of the phenyl group, naphthyl group, and anthracenyl group.

[0167] In the aforementioned chemical formula 301, Ar 113 ~Ar 116 They are independent of each other, C1-C 10 Alkyl groups, phenyl groups, naphthyl groups, phenantrenyl groups, and pyrenyl groups; and A phenyl group, naphthyl group, phenantrenyl group, and pyrenyl group, selected from those substituted with one or more of the phenyl group, naphthyl group, and anthracenyl group.

[0168] In the aforementioned chemical formula 301, g, h, i, and j are independent integers between 0 and 4, for example, 0, 1, or 2.

[0169] In the aforementioned chemical formula 301, Ar 113 ~Ar 116 They are independent of each other, C1-C12 10 alkyl group; Phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenantrenyl group, and fluorenyl group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Phenyl groups, naphthyl groups, anthracenyl groups, pyrenyl groups, phenantrenyl groups, and fluorenyl groups substituted with one or more of the following: alkoxy groups, phenyl groups, naphthyl groups, anthracenyl groups, pyrenyl groups, phenantrenyl groups, and fluorenyl groups; and [ka] ; can be selected from, but is not limited to, those options.

[0170] Alternatively, the host may contain a compound represented by the following chemical formula 302: [ka]

[0171] In the aforementioned chemical formula 302, Ar122 ~Ar 125 For a detailed explanation of the above chemical formula 301 Ar 113 Refer to the explanation for details.

[0172] In the aforementioned chemical formula 302, Ar 126 and Ar 127 These are, independently of each other, C1-C 10 It is an alkyl group (for example, a methyl group, an ethyl group, or a propyl group).

[0173] In the aforementioned chemical formula 302, k and l are independent integers between 0 and 4. For example, k and l are 0, 1, or 2.

[0174] According to one embodiment, the host may contain at least one compound from the following compounds H1 to H26: [ka] [ka] [ka] [ka] [ka]

[0175] According to one embodiment, the host may consist of one type of compound. For example, the one type of compound may be arbitrarily selected from the first substance (hole-transporting host) and the second substance (electron-transporting host) as described above.

[0176] According to one embodiment, the host may comprise two or more compounds. For example, the host may comprise two or more different hole-transporting hosts, two or more different electron-transporting hosts, or a combination of one or more hole-transporting hosts and one or more electron-transporting hosts.

[0177] [Emitter in the light-emitting layer] The emitter includes the heterocyclic compound.

[0178] [Sensitizer in the luminescent layer] According to one embodiment, the sensorizer may contain a phosphorescent compound.

[0179] According to one embodiment, the phosphorescent compound may include an organometallic compound containing one or more metals.

[0180] According to one embodiment, the organometallic compound is one or more metals selected from transition metals (M 11 ) and organic ligand (L 11 ) includes, L 11 and M 11 It can form one, two, three, or four cyclometallated rings.

[0181] According to one embodiment, the organometallic compound is represented by the following chemical formula 101.

[0182] [C101] M 11 (L 11 ) n11 (L 12 ) n12 In the aforementioned chemical formula 101, M 11 It is a transition metal, L 11 It is a ligand represented by one of the following chemical formulas 1-1 to 1-4, L 12 It is a monodentate or bidentate ligand, n11 is 1, n12 is selected from 0, 1, and 2. [ka]

[0183] In the above chemical formulas 1-1 to 1-4, A1-A4 are independent of each other, and are either substituted or non-substituted C5-C. 30 Carbon ring group, substituted or unsubstituted C1-C 30 Selected from heterocyclic and acyclic groups, Y 11 ~Y 14 These are, independently of each other, chemical bonds, O, S, N(R) 91 ), B(R 91 ), P(R 91 ), or C(R 91 )(R 92 ) and T1-T4 are independent of each other, with single bonds, double bonds, and *-N(R) 93 )-*', *-B(R 93 )-*'、*-P(R 93 )-*', *-C(R 93 )(R 94 )-*'、*-Si(R 93 )(R 94 )-*'、*-Ge(R 93 )(R 94 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 93 )=*', *=C(R 93 )-*', *-C(R 93 )=C(R 94 Selected from )-*', *-C(=S)-*', and *-C≡C-*', The substituted C5-C 30 Substituents of a carbocyclic group, substituted C1-C 30 Substituents of the heterocyclic group, and R 91 ~R 94 These are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl alkyl groups, substituted or unsubstituted C2-C 60 Alkenyl group, substituted or unsubstituted C2-C 60Alkynyl group, substituted or unsubstituted C1-C 60 Alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C1-C 10 Heterocycloalkenyl group, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio group, substituted or unsubstituted C1-C 60 Selected from heteroaryl groups, substituted or unsubstituted monovalent aromatic condensed polycyclic groups, substituted or unsubstituted monovalent aromatic heterocondensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), and -P(=S)(Q1)(Q2), but the substituted C5-C 30 Substituents of carbocyclic groups and substituted C1-C 30 The substituents on the heterocyclic group are not hydrogen, *1, *2, *3 and *4 are M 11 It is a combined site with, Q1-Q3 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic heterocondensed polycyclic group; or Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, C1-C 60 Alkyl alkyl group, C6-C 60 Aryl group, C1-C 60 C1-C substituted with heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic heterocondensed polycyclic groups, or any combination thereof. 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 It is a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic heterocondensed polycyclic group.

[0184] According to one embodiment, the transition metal may be platinum (Pt), palladium (Pd), gold (Au), iridium (Ir), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0185] According to one embodiment, the sensorizer may contain a delayed-fluorescence compound.

[0186] According to one embodiment, the delayed fluorescent compound is represented by the following chemical formula 101 or 102.

[0187] [ka]

[0188] In the aforementioned chemical formulas 101 and 102, A 21 This is an acceptor group, D 21 is a donor group, m21 is 1, 2, or 3, and n21 is 1, 2, or 3. In the aforementioned chemical formula 101, the sum of n21 and m21 is 5 or less, and in the aforementioned chemical formula 102, the sum of n21 and m21 is 6 or less. R 201 C1-C5 is composed of hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, and substituted or unsubstituted C1-C5. 60 Alkyl alkyl groups, substituted or unsubstituted C2-C 60 Alkenyl group, substituted or unsubstituted C2-C 60 Alkynyl group, substituted or unsubstituted C1-C 60 Alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C1-C 10 Heterocycloalkenyl group, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C7-C 60 Alkylaryl group, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio group, substituted or unsubstituted C1-C 60 Heteroaryl group, substituted or unsubstituted C2-C 60 Alkyl heteroaryl group, substituted or unsubstituted C1-C60 Heteroaryloxy group, substituted or unsubstituted C1-C 60 A heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, selected from -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), and -P(=S)(Q1)(Q2), with multiple R 201 They selectively combine with each other, forming substituted or unsubstituted C5-C 30 A carbocyclic group, or a substituted or unsubstituted C1-C 30 It can form a heterocyclic group, Q1-Q3 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, and C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C7-C 60 Alkylaryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, C2-C 60 Alkyl heteroaryl group, C1-C 60 Heteroaryloxy group, C1-C 60 Heteroarylthio group, monovalent aromatic condensed polycyclic group, monovalent aromatic heterocondensed polycyclic group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, deuterium, -F, cyano group, C1-C 60 Alkyl groups, and C6-C 60C1-C substituted with at least one selected from aryl groups 60 Alkyl groups, as well as deuterium, -F, cyano group, C1-C 60 Alkyl groups, and C6-C 60 C6-C substituted with at least one selected from aryl groups 60 Selected from aryl groups.

[0189] According to one embodiment, in the chemical formulas 101 and 102, D 21 It is a substituted or unsubstituted π-electron-deficient nitrogen-free cyclic group.

[0190] Specifically, the π-electron-deficient nitrogen-free cyclic groups are benzene, heptalene, indene, naphthalene, azulene, indacene, acenaphthylene, fluorene, spirobifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluorantene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentacene, hexacene, pentacene, rubicene, cologen, ovalene, pyrrole, and isoindo. A fused ring of two or more of the aforementioned π-electron-deficient nitrogen-free cyclic groups is selected from, but is not limited to, a chlorofluorobenzene group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophenesulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzoflocarbazole group, a benzothienocarbazole group, and a triindrobenzene group; and a fused ring of two or more of the aforementioned π-electron-deficient nitrogen-free cyclic groups.

[0191] For example, in the above chemical formulas 101 and 102, A 21 -F, cyano group, π-electron deficient nitrogen-containing cyclic group; -C1-C substituted with at least one selected from F and cyano groups. 60 an alkyl group, a π-electron-deficient nitrogen-containing cyclic group, and a π-electron-deficient nitrogen-free cyclic group; and Deuterium, C1-C60 A π-electron-deficient nitrogen-containing cyclic group is selected from an alkyl group, a π-electron-deficient nitrogen-containing cyclic group, and a π-electron-deficient nitrogen-free cyclic group, which is substituted with at least one of these.

[0192] Specifically, the π-electron-deficient nitrogen-free cyclic group refers to the one described above.

[0193] Specifically, the π-electron-deficient nitrogen-containing cyclic group is a cyclic group having at least one *-N=*' moiety, such as imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, sinnoline group Selected from: a group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetraazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, azacarbazole group, and benzimidazole group; and a condensed ring of two or more of the π-electron-deficient nitrogen-containing cyclic groups.

[0194] According to one embodiment, the content of the sensor in the organic layer is greater than the content of the emitter. For example, the volume ratio of the sensor to the emitter is 30:0.1 to 10:3, or 10:0.1 to 20:5. As another example, the weight ratio of the sensor to the emitter is 10:0.1 to 20:5. On the other hand, the volume ratio of the host to the sensor in the organic layer is 60:40 to 95:5, or 70:30 to 90:10. Alternatively, the weight ratio of the host to the sensor is selected within the range of 60:40 to 95:5. By satisfying the above-described content ranges, the organic light-emitting element can have improved luminous efficiency and / or lifetime characteristics.

[0195] Figure 1 schematically shows a cross-sectional view of an organic light-emitting element 10 according to one embodiment of the present invention. The structure and manufacturing method of the organic light-emitting element according to one embodiment of the present invention will be described below with reference to Figure 1. The organic light-emitting element 10 has a structure in which a first electrode 11, an organic layer 15, and a second electrode 19 are stacked in order.

[0196] A substrate may be further placed below the first electrode 11 or above the second electrode 19. While a substrate commonly used in organic light-emitting devices can be used as the substrate, a glass substrate or a transparent plastic substrate with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water repellency can also be used.

[0197] The first electrode 11 is formed, for example, by providing a material for the first electrode on the upper part of a substrate using a vapor deposition method or a sputtering method. The first electrode 11 is also the anode. The material for the first electrode is selected from materials having a high work function so that hole injection is easy. The first electrode 11 is a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. As the material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc. can be used. Alternatively, metals such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) can be used.

[0198] The first electrode 11 may have a single layer or a multilayer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but is not limited to this.

[0199] An organic layer 15 is placed on top of the first electrode 11.

[0200] The organic layer 15 includes a hole transport region, an emission layer, and an electron transport region.

[0201] The hole transport region is located between the first electrode 11 and the light-emitting layer.

[0202] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.

[0203] The hole transport region may consist only of a hole injection layer, or only of a hole transport layer. Alternatively, the hole transport region may have a structure of hole injection layer / hole transport layer or hole injection layer / hole transport layer / electron blocking layer, stacked sequentially from the first electrode 11.

[0204] If the hole transport region includes a hole injection layer, the hole injection layer (HIL) is formed on top of the first electrode 11 using various methods such as vacuum deposition, spin coating, casting, and LB (Langmuir-Blodgett) method.

[0205] When forming a hole injection layer by vacuum deposition, the deposition conditions vary depending on the compound used as the hole injection layer material, the desired structure of the hole injection layer, and its thermal properties. For example, the deposition temperature is approximately 100°C to 500°C, and the vacuum level is approximately 10°C. -8 torr~approximately 10 -3 Torr is selected within the range of approximately 0.01 Å / sec to approximately 100 Å / sec, but is not limited to these ranges.

[0206] When forming a hole injection layer by spin coating, the coating conditions vary depending on the compound used as the hole injection layer material, the desired structure of the hole injection layer, and its thermal properties. However, the coating speed is typically selected between approximately 2,000 rpm and 5,000 rpm, and the heat treatment temperature for solvent removal after coating is typically between approximately 80°C and 200°C, although these are not the only possible conditions.

[0207] The formation conditions for the hole transport layer and the electron blocking layer refer to the formation conditions for the hole injection layer.

[0208] The hole transport region may include, for example, at least one of the following: m-MTDATA, TDATA, 2-TNATA, NPB, 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 chemical formula 201, and a compound represented by the following chemical formula 202: [ka] [ka] [ka] [ka]

[0209] In the aforementioned chemical formula 201, Ar 101 and Ar 102 They are independent of each other, Phenylene group, pentarenylene group, indenylene group, naphthylene group, azurenylene group, heptarenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenantrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenyrene group, naphthacenylene group, picenylene group, perillenylene group, or pentacenylene group; or Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Phenylene, pentarenylene, indenylene, naphthylene, azurenylene, heptarenylene, acenaphthylene, fluorenylene, phenalenylene, phenantrenylene, anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenyrenylene, naphthacenylene, picenylene, perylene, or pentasenylene group, substituted with a heteroaryl group, a monovalent nonaromatic condensed polycyclic group, a monovalent nonaromatic heterocondensed polycyclic group, or any combination thereof.

[0210] In the aforementioned chemical formula 201, xa and xb are independent integers between 0 and 5, or 0, 1, or 2. For example, xa is 1 and xb is 0, but is not limited to that.

[0211] In the above chemical formulas 201 and 202, the R 101 ~R 108 , R 111 ~R 119 and R 121 ~R 124 They are independent of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 10 Alkyl groups (e.g., methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc.), or C1-C 10 Alkoxy groups (e.g., methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, etc.); C1-C substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, or any combination thereof. 10 Alkyl or C1-C 10 Alkoxy group; Phenyl group, naphthyl group, anthracenyl group, fluorenyl group, or pyrenyl group; or Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 10 Alkyl alkyl group, C1-C 10 A phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl group substituted with an alkoxy group or any combination thereof; but not limited to these.

[0212] In the above chemical formula 201, R 109 teeth, Phenyl group, naphthyl group, anthracenyl group, or pyridinyl group; or Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 20 Alkyl alkyl group, C1-C 20A phenyl group, naphthyl group, anthracenyl group, or pyridinyl group substituted with an alkoxy group, a phenyl group, a naphthyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or any combination thereof;

[0213] According to one embodiment, the compound represented by chemical formula 201 is represented by the following chemical formula 201A, but is not limited thereto: [ka]

[0214] In the above chemical formula 201A, R 101 , R 111 , R 112 and R 109 For a detailed explanation, please refer to the above.

[0215] For example, the compounds represented by chemical formula 201 and chemical formula 202 include, but are not limited to, the following compounds HT1 to HT20: [ka] [ka] [ka] [ka]

[0216] The thickness of the hole transport region is approximately 100 Å to approximately 10,000 Å, for example, approximately 100 Å to approximately 1,000 Å. If the hole transport region includes at least one of the hole injection layer and the hole transport layer, the thickness of the hole injection layer is approximately 100 Å to approximately 10,000 Å, for example, approximately 100 Å to approximately 1,000 Å, and the thickness of the hole transport layer is approximately 50 Å to approximately 2,000 Å, for example, approximately 100 Å to approximately 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the above-described ranges, the hole transport characteristics to be satisfied can be obtained without a substantial increase in driving voltage.

[0217] The hole transport region may further contain, in addition to the aforementioned substances, charge-generating materials to improve conductivity. The charge-generating materials are uniformly or non-uniformly dispersed within the hole transport region.

[0218] The charge-generating substance is, for example, a p-type dopant. The p-type dopant is, but is not limited to, one of a quinone derivative, a metal oxide, and a cyano group-containing compound. For example, non-restrictive examples of the p-type dopant include, but is not limited to, quinone derivatives such as tetracyanoquinone dimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethane (F4-TCNQ), metal oxides such as tungsten oxide and molybdenum oxide, and cyano group-containing compounds such as the compounds HT-D1 and F12 listed below. [ka] [ka]

[0219] The hole transport region may further include a buffer layer.

[0220] The buffer layer can compensate for the optical resonance distance due to the wavelength of light emitted from the light-emitting layer, thereby increasing efficiency.

[0221] An emissive layer (EML) can be formed on top of the hole transport region using methods such as vacuum deposition, spin coating, casting, or LB. When forming the emissive layer by vacuum deposition or spin coating, the deposition and coating conditions vary depending on the compound used, but are generally selected within approximately the same range as those used for forming the hole injection layer.

[0222] On the other hand, if the hole transport region includes an electron blocking layer, the material of the electron blocking layer is selected from, but is not limited to, materials usable in the hole transport region as described above and host materials described later. For example, if the hole transport region includes an electron blocking layer, mCP described later can be used as the material of the electron blocking layer.

[0223] If the organic light-emitting element is a full-color organic light-emitting element, the light-emitting layer may be patterned with a red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer. Alternatively, the light-emitting layer may have a structure in which a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer are laminated, allowing it to emit white light, and various other modifications are possible.

[0224] When the light-emitting layer contains a host and a dopant, the dopant content is usually selected in the range of about 0.01 parts by weight to about 15 parts by weight, based on about 100 parts by weight of the host, but is not limited thereto.

[0225] The thickness of the light-emitting layer is approximately 100 Å to approximately 1,000 Å, for example, approximately 200 Å to approximately 600 Å. When the thickness of the light-emitting layer satisfies the above range, excellent light-emitting characteristics can be achieved without a substantial increase in driving voltage.

[0226] Next, an electron transport region is placed above the light-emitting layer.

[0227] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0228] For example, the electron transport region may have, but is not limited to, a hole blocking layer / electron transport layer / electron injection layer or an electron transport layer / electron injection layer structure. The electron transport layer may be a single layer or a multilayer structure containing two or more different materials.

[0229] The formation conditions for the hole blocking layer, electron transport layer, and electron injection layer in the electron transport region refer to the formation conditions for the hole injection layer.

[0230] If the electron transport region includes a hole blocking layer, the hole blocking layer includes, for example, at least one of the following BCP, Bphen, and BAlq, but is not limited to them. [ka]

[0231] The thickness of the hole blocking layer is approximately 20 Å to 1,000 Å, for example, approximately 30 Å to 300 Å. When the thickness of the hole blocking layer satisfies the above range, excellent hole blocking characteristics can be obtained without a substantial increase in driving voltage.

[0232] The electron transport layer may further include at least one of BCP, Bphen, Alq3, BAlq, TAZ, and NTAZ. [ka]

[0233] Alternatively, the electron transport layer may contain, but is not limited to, at least one of the following compounds ET1 to ET25. [ka] [ka]

[0234] The thickness of the electron transport layer is approximately 100 Å to 1,000 Å, for example, approximately 150 Å to 500 Å. When the thickness of the electron transport layer satisfies the above range, the desired electron transport characteristics can be obtained without a substantial increase in driving voltage.

[0235] The electron transport layer may further contain metal-containing materials in addition to the materials described above.

[0236] The metal-containing substance may also contain a Li complex. The Li complex may include, for example, the following compounds ET-D1 (lithium quinolate (LiQ)) or ET-D2. [ka]

[0237] Furthermore, the electron transport region includes an electron injection layer (EIL) that facilitates the injection of electrons from the second electrode 19.

[0238] The electron injection layer may contain LiF, NaCl, CsF, Li2O, BaO, or any combination thereof.

[0239] The thickness of the electron injection layer is approximately 1 Å to approximately 100 Å, for example, approximately 3 Å to approximately 90 Å. When the thickness of the electron injection layer satisfies the above range, the desired electron injection characteristics can be obtained without a substantial increase in the driving voltage.

[0240] A second electrode 19 is provided on the upper part of the organic layer 15. The second electrode 19 also serves as the cathode. As the material for the second electrode 19, metals, alloys, conductive compounds, and combinations thereof with relatively low work functions can be used. Specifically, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc., can be used as materials for forming the second electrode 19. Alternatively, various modifications are possible, such as forming a transmissive second electrode 19 using ITO or IZO to obtain a front-facing light-emitting element.

[0241] The organic light-emitting element described above has been explained with reference to Figure 1, but is not limited to that.

[0242] In another aspect, an electronic device including the organic light-emitting element is provided.

[0243] The electronic device may further include a thin-film transistor in addition to the organic light-emitting element described above. The thin-film transistor includes a source electrode, a drain electrode, and an active layer, and either one of the source electrode and the drain electrode may be electrically connected to either one of the first electrode and the second electrode of the organic light-emitting element.

[0244] In another aspect, a diagnostic composition comprising the heterocyclic compound represented by chemical formula 1 is provided.

[0245] The diagnostic composition may contain one or more heterocyclic compounds represented by the chemical formula 1.

[0246] Since the heterocyclic compound represented by chemical formula 1 can provide high luminescence efficiency, a diagnostic composition containing the heterocyclic compound can have high diagnostic efficiency.

[0247] The diagnostic composition can be applied in a variety of ways, including to various diagnostic kits, diagnostic reagents, biosensors, and biomarkers.

[0248] In this specification, C1-C 60 Alkyl groups refer to monovalent groups of saturated aliphatic hydrocarbons having 1 to 60 carbon atoms, either linear or branched. Specific examples include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isoamyl, and hexyl groups. In this specification, C1-C 60 The alkylene group is the C1-C 60 This refers to a divalent group that has the same structure as an alkyl group.

[0249] In this specification, C1-C 60 Alkyl alkyl group, C1-C 20 Alkyl groups, and / or C1-C 10Examples of alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec-decyl group, tert-decyl group, or any combination thereof. This includes mixed-substituted or unsubstituted methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, sec-butyl groups, isobutyl groups, tert-butyl groups, n-pentyl groups, tert-pentyl groups, neopentyl groups, isopentyl groups, sec-pentyl groups, 3-pentyl groups, sec-isopentyl groups, n-hexyl groups, isohexyl groups, sec-hexyl groups, tert-hexyl groups, n-heptyl groups, isoheptyl groups, sec-heptyl groups, tert-heptyl groups, n-octyl groups, isooctyl groups, sec-octyl groups, tert-octyl groups, n-nonyl groups, isononyl groups, sec-nonyl groups, tert-nonyl groups, n-decyl groups, isodecyl groups, sec-decyl groups, or tert-decyl groups. For example, the aforementioned chemical formula 9-33 is a branched C6 alkyl group and appears to be a tert-butyl group substituted with two methyl groups.

[0250] In this specification, C1-C 60 The alkoxy group is -OA 101 (Here, A 101 is the aforementioned C1-C 60 This refers to a monovalent group having the chemical formula (which is an alkyl group), and specific examples include the methoxy group, ethoxy group, and isopropyloxy group.

[0251] In this specification, C1-C 60 Alkoxy group, C1-C 20 Alkoxy group, or C1-C10 Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, and pentoxy groups.

[0252] In this specification, C2-C 60 The alkenyl group is the C2-C 60 A structure having one or more carbon-carbon double bonds in the middle or terminal of an alkyl group, specific examples of which include ethenyl, propenyl, and butenyl groups. In this specification, C2-C 60 The alkenylene group is the C2-C 60 This refers to a divalent group that has the same structure as an alkenyl group.

[0253] In this specification, C2-C 60 The alkynyl group is the C2-C 60 It has a structure containing one or more carbon-carbon triple bonds in the middle or terminal of an alkyl group, and specific examples include an ethynyl group, a propynyl group, etc. In this specification, C2-C 60 The alkynylene group is the C2-C 60 This refers to a divalent group that has the same structure as an alkynyl group.

[0254] In this specification, C3-C 10 Cycloalkyl groups refer to monocyclic groups of monovalent saturated hydrocarbons having 3 to 10 carbon atoms, and specific examples include cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, and cycloheptyl groups. In this specification, C3-C 10 The cycloalkylene group is the C3-C 10 This refers to a divalent group having the same structure as a cycloalkyl group.

[0255] In this specification, C3-C 10 Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantanyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl (norbornyl), and bicyclo[2.2.2]octyl.

[0256] In this specification, C1-C 10 The heterocycloalkyl group means a monovalent monocyclic group having 1 to 10 carbon atoms and containing at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom. Specific examples thereof include a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and the like. In this specification, C1-C 10 The heterocycloalkylene group is the C1-C 10 It means a divalent group having the same structure as the above heterocycloalkyl group.

[0257] In this specification, C1-C 10 Examples of the heterocycloalkyl group include a silolanyl group, a silinanil group, a tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, a tetrahydrothiophenyl group, and the like.

[0258] In this specification, C3-C 10 The cycloalkenyl group is a monovalent monocyclic group having 3 to 10 carbon atoms and having at least one carbon-carbon double bond in the ring, but not having aromaticity. Specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. In this specification, C3-C 10 The cycloalkenylene group is the C3-C[[ID=2:4]] 10 It means a divalent group having the same structure as the above cycloalkenyl group.

[0259] In this specification, C2-C 10 The heterocycloalkenyl group is a monovalent monocyclic group having 2 to 10 carbon atoms and containing at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and having at least one double bond in the ring. The C2-C 10 Specific examples of the heterocycloalkenyl group include a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like. In this specification, C2-C 10 The heterocycloalkenylene group is the C2-C 10 It means a divalent group having the same structure as the above heterocycloalkenyl group.

[0260] In this specification, C6-C 60 An aryl group means a monovalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms, and C6-C 60 An arylene group means a divalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms. When the 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, a chrysenyl group, etc. When the C6-C 60 The aryl group and C6-C 60 When the arylene group contains two or more rings, the two or more rings are fused to each other.

[0261] In this specification, C7-C 60 An alkylaryl group means a C6-C 60 aryl group substituted with at least one C1-C 60 alkyl group.

[0262] In this specification, C1-C 60 A heteroaryl group means a monovalent group having a cyclic aromatic system with 1 to 60 carbon atoms and containing at least one heteroatom selected from N, O, P, Si and S as a ring-forming atom, and C1-C 60 A heteroarylene group means a divalent group having a cyclic aromatic system with 1 to 60 carbon atoms and containing at least one heteroatom selected from N, O, P and S as a ring-forming atom. When the C1-C 60 Specific examples of the heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, etc. When the C1-C 60 The heteroaryl group and C1-C 60 When the heteroarylene group contains two or more rings, the two or more rings are fused to each other.

[0263] In this specification, C2-C 60 An alkylheteroaryl group means a C1-C 60 heteroaryl group substituted with at least one C1-C 60It means a heteroaryl group.

[0264] In this specification, C6-C 60 The aryloxy group is -OA 102 (Here, A 102 is the above C6-C 60 (It is an aryl group) and C6-C 60 The arylthio group is -SA 103 (Here, A 103 is the above C6-C 60 It indicates that it is an aryl group.

[0265] In this specification, C1-C 60 The heteroaryloxy group is -OA 104 (Here, A 104 is the aforementioned C1-C 60 (It is a heteroaryl group) and C1-C 60 The heteroarylthio group is -SA 105 (Here, A 105 is the aforementioned C1-C 60 It indicates a heteroaryl group.

[0266] In this specification, a monovalent non-aromatic condensed polycyclic group means a monovalent group (for example, having 8 to 60 carbon atoms) in which two or more rings are fused to each other, containing only carbon as the ring-forming atom, and having non-aromaticity as a whole molecule. Specific examples of the monovalent non-aromatic condensed polycyclic group include the fluorenyl group. In this specification, a divalent non-aromatic condensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

[0267] In this specification, a monovalent non-aromatic heterocondensed polycyclic group means a monovalent group (for example, having 1 to 60 carbon atoms) in which two or more rings are fused to each other, and which contains heteroatoms selected from N, O, P, Si, and S as ring-forming atoms in addition to carbon, and the entire molecule is non-aromatic. The monovalent non-aromatic heterocondensed polycyclic group includes a carbazolyl group, etc. In this specification, a divalent non-aromatic heterocondensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic heterocondensed polycyclic group.

[0268] In this specification, C5-C 30 A carbocyclic group is a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring-forming atoms. 30 A carbocyclic group is either a monocyclic or polycyclic group. (at least one R 1a (Substituted or not substituted) C5-C 30 A "carbon ring group" is, for example, (at least one R 1a This includes adamantane groups (substituted or unsubstituted), norbornene groups, bicyclo[1.1.1]pentane groups, bicyclo[2.1.1]hexane groups, bicyclo[2.2.1]heptane groups (norbornane groups), bicyclo[2.2.2]octane groups, cyclopentane groups, cyclohexane groups, cyclohexene groups, benzene groups, naphthalene groups, anthracene groups, phenanthrene groups, triphenylene groups, pyrene groups, chrysene groups, 1,2,3,4-tetrahydronaphthalene groups, cyclopentadiene groups, silole groups, fluorene groups, etc.

[0269] In this specification, C1-C 30 A heterocyclic group is a saturated or unsaturated cyclic group having at least one heteroatom selected from N, O, P, Si, and S, in addition to 1 to 30 carbon atoms as ring-forming atoms. 30 A heterocyclic group is either a monocyclic or polycyclic group. (at least one R 1a (Substituted or not substituted) C1-C 30 A heterocyclic group is, for example, (at least one R 1aThiophene group (substituted or unsubstituted), furan group, pyrrole group, silole group, borol group, phosphole group, selenofen group, gelmol group, benzothiophene group, benzofuran group, indole group, indene group, benzosilole group, benzoborol group, benzophosphole group, benzoselenophene group, benzogermol group, dibenzothiophene group, dibenzofuran group, carbazole group, dibenzosilole group, dibenzoborol group, dibenzophosphole Group, dibenzoselenophen group, dibenzogermol group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzosilol group, azabenzobolol group, azabenzophosphole group, azabenzoselenophene group, azabenzogermol group, azadibenzothiophene group, azadibenzofuran group, aza Carbazole group, azafluorene group, azadibenzosilol group, azadibenzobolol group, azadibenzophosphole group, azadibenzoselenophene group, azadibenzogermole group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group This includes phenanthroline group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, etc.

[0270] In this specification, TMS represents *-Si(CH3)3 and TMG represents *-Ge(CH3)3.

[0271] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, or C1-C 60 alkoxy group; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C1-C 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic hetero-condensed polycyclic group, -N(Q 11 )(Q 12 ), -Si(Q 11 )(Q 12 )(Q 13 ), -Ge(Q 11 )(Q 12 )(Q 13 ), -C(=O)(Q 11 ), -S(=O)(Q 11 ), -S(=O)2(Q 11 ), -B(Q 11 )(Q 12 ), -P(Q 11 )(Q 12 ), -P(=O)(Q 11 )(Q 12 ), -P(=S)(Q 11 )(Q 12 ), or C1-C substituted with any combination thereof60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, or C1-C 60 Alkoxy group; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q 21 )(Q 22 ), -Si(Q 21 )(Q 22 )(Q 23 ), -Ge(Q 21 )(Q 22 )(Q 23 ), -C(=O)(Q 21 ), -S(=O)(Q 21 ), -S(=O)2(Q 21 ), -B(Q 21 )(Q 22 ), -P(Q 21 )(Q 22 ), -P(=O)(Q 21 )(Q 22 ), -P(=S)(Q 21 )(Q 22 ), or any combination thereof, C3-C 10 Cycloalkyl groups, C1-C 10Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, or monovalent non-aromatic heterocondensed polycyclic groups; -N(Q 31 )(Q 32 ), -Si(Q 31 )(Q 32 )(Q 33 ), -Ge(Q 31 )(Q 32 )(Q 33 ), -C(=O)(Q 31 ), -S(=O)(Q 31 ), -S(=O)2(Q 31 ), -B(Q 31 )(Q 32 ), -P(Q 31 )(Q 32 ), -P(=O)(Q 31 )(Q 32 ), or -P(Q 31 )(Q 32 );or Any combination of those; The above Q1-Q3, Q 11 ~Q 13 Q 21 ~Q 23 and Q 31 ~Q 33 These are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic heterocondensed polycyclic group; or Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, C1-C 60 Alkyl alkyl group, C6-C 60 Aryl group, C1-C 60 C1-C substituted with heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic heterocondensed polycyclic groups, or any combination thereof. 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 It is a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic heterocondensed polycyclic group.

[0272] The following describes in more detail a compound and an organic light-emitting element according to one embodiment of the present invention, with reference to synthesis examples and examples, but the present invention is not limited to the following synthesis examples and examples. In the following synthesis examples, the expression "'B' was used instead of 'A'" means that the amount of "B" used and the amount of "A" used are the same on a molar equivalent basis.

[0273] [Example of combination] Synthesis Example 1: Synthesis of Compound 41 [ka]

[0274] (1) Synthesis of compound 41-3 Under nitrogen, 2,6-dibromo-4-(tert-butyl)aniline (20.00 g, 65.24 mmol), phenylboronic acid (17.50 g, 143.5 mmol), Na2CO3 (20.74 g, 195.7 mmol), Pd(PPh3)4 (7.54 g, 6.52 mmol), and toluene / EtOH / DW (200 ml, 2:1:1) were added and heated at 100°C for 24 hours. The reaction was then terminated with ammonium chloride solution. After extraction with dichloromethane, drying over MgSO4, and removal of the solvent, the solution was purified by column chromatography with MC:hexane (1:4) to obtain 17.21 g of a white solid. LC-MS (m / z) calculated value: 301.183 g / mol, measured value: [M+] 302.194 g / mol

[0275] (2) Synthesis of compound 41-2 Under nitrogen, 7-bromo-2,12-di-tert-butyl-5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene (7.00 g, 15.21 mmol), compound 41-3 (5.50 g, 18.25 mmol), NaOtBu (2.19 g, 22.81 mmol), Pd2(dba)3 (0.696 g, 0.760 mmol), and SPhos (0.624 g, 1.52 mmol) were mixed with xylene (76 ml) at a temperature of 150°C and stirred for 24 hours. After cooling to room temperature, the mixture was extracted with dichloromethane, dried over MgSO4, and the solvent was removed. The mixture was then purified by column chromatography with MC:hexane (1:7) to obtain 7.52 g of a white solid. LC-MS (m / z) calculated value: 681.378 g / mol, measured value: [M+] 682.423 g / mol

[0276] (3) Synthesis of compound 41-1 Under nitrogen, 1,3-dibromo-5-(tert-butyl)benzene (1.50 g, 5.24 mmol), compound 41-2 (7.50 g, 11.00 mmol), NaOtBu (1.76 g, 18.34 mmol), Pd2(dba)3 (0.480 g, 0.524 mmol), and SPhos (0.430 g, 1.05 mmol) were mixed with xylene (26 ml) at a temperature of 150°C and stirred for 24 hours. The reaction was terminated by cooling to room temperature and adding ammonium chloride solution. After extraction of the organic layer, it was dried over MgSO4, the solvent was removed, and the mixture was purified by column chromatography with MC:hexane (1:5) to obtain 4.30 g of a white solid. LCMS (m / z) calculated value: 1492.834 g / mol, measured value: [M+] 1493.943 g / mol

[0277] (4) Synthesis of compound 41 Under nitrogen, compound 41-1 (5.00 g, 3.35 mmol) and BI3 (1.44 g, 3.68 mmol) were mixed with 1,2,4-trichlorobenzene (67 ml) and stirred at a temperature of 190°C for 18 hours. After cooling to room temperature, the reaction was terminated with Na2CO3 solution. The organic layer was extracted, dried over MgSO4, and after removing the solvent, the mixture was purified by column chromatography with MC:hexane (1:9) to obtain 0.85 g of solid compound 41. LC-MS (m / z) calculated value: 1500.820 g / mol, measured value: [M+] 1501.830 g / mol

[0278] [Examples] Evaluation Example 1: Evaluation of Photoluminescence Properties Compounds 41 and A were dissolved in dichloromethane (MC) with polymethyl methacrylate (PMMA) at a concentration of 1% by weight, and then thin films were formed on a quartz substrate (20 mm × 20 mm) by spin coating. After excitation with an excitation wavelength of 330 nm at room temperature, photoluminescence (PL) was measured. Fluorescence and delayed fluorescence lifetimes were also measured at room temperature using a fluorescence lifetime analyzer. For compound B, the results were compared with known results (Nat. Commun., 2024, 15, 2361). The results are shown in Table 2.

[0279] [Table 2] [ka]

[0280] Table 2 above shows that the heterocyclic compound according to one embodiment exhibits excellent luminescence properties. Furthermore, it was found that the heterocyclic compound according to one embodiment is even more suitable for deep blue luminescence and has an even narrower full width at half maximum compared to compounds A and B.

[0281] Example 1 The ITO glass substrate was cut to a size of 50mm x 50mm x 0.5mm, ultrasonically cleaned in acetone isopropyl alcohol and pure water for 15 minutes each, and then cleaned with UV ozone for 30 minutes.

[0282] Next, HAT-CN was deposited on the ITO electrode (anode) on the glass substrate to form a 100 Å thick hole injection layer, NPB was deposited on the hole injection layer to form a 500 Å thick first hole transport layer, TCTA was deposited on the first hole transport layer to form a 50 Å thick second hole transport layer, and mCP was deposited on the second hole transport layer to form a 50 Å thick electron blocking layer.

[0283] A first host (H25), a second host (H26), and an emitter (compound 41) were co-deposited on the electron blocking layer to form a 400 Å thick light-emitting layer. In this process, the first and second hosts were mixed in a ratio of 65:35, and the amount of the emitter was adjusted to 2% by weight relative to the total weight of the first host, second host, and emitter, respectively.

[0284] An organic light-emitting device was fabricated by depositing DBFPO on the light-emitting layer to form a 100 Å thick hole-blocking layer, co-depositing DBFPO and LiQ in a 5:5 weight ratio to form a 300 Å thick electron-transport layer, depositing LiQ on the electron-transport layer to form a 10 Å thick electron-injection layer, and depositing 1,000 Å thick Al on the electron-injection layer to form a cathode. [ka] [ka] [ka]

[0285] Comparative Example 1 An organic light-emitting element was fabricated using the same method as in Example 1, except that the compounds listed in Table 2 were used as emitters during the formation of the light-emitting layer.

[0286] Evaluation Example 2: Characterization of Organic Light-Emitting Devices The color coordinates (CIEy) and emission wavelength (λ) of the organic light-emitting element fabricated in Example 1 and Comparative Example 1 are given above. EL ), relative efficiency (at 1,000 cd / m²) 2 The roll-off characteristics of the initial efficiency were measured and evaluated using a current / voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A). The results are shown in Table 3 below.

[0287] [Table 3] [ka]

[0288] Table 3 above shows that the organic light-emitting element according to one embodiment exhibits excellent driving voltage, luminous efficiency, and lifetime characteristics. Furthermore, the organic light-emitting element of Example 1 was found to have superior color coordinates, shorter wavelengths, even higher efficiency, and superior roll-off characteristics compared to the organic light-emitting element of Comparative Example 1. [Explanation of Symbols]

[0289] 10 Organic light-emitting devices 11 1st electrode 15 Organic layer 19 Second electrode

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