Heterocyclic compound and organic light emitting device including the same

文档序号：1196620 发布日期：2020-09-01 浏览：6次中文

阅读说明：本技术 杂环化合物和包括其的有机发光器件 (Heterocyclic compound and organic light emitting device including the same ) 是由权殷淑南煐敏朴商浩裵惠珍孙准模吴原硕郑庸植 D.克拉夫丘克于 2020-02-26 设计创作，主要内容包括：提供杂环化合物和包括其的有机发光器件,所述杂环化合物由式1表示。在式1中,各基团的定义与在说明书中描述的相同。式1<Image he="241" wi="700" file="DDA0002395732360000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(Provided are a heterocyclic compound and an organic light emitting device including the same, the heterocyclic compound being represented by formula 1. In formula 1, the definitions of the groups are the same as described in the specification. Formula 1)

1. A heterocyclic compound represented by formula 1:

wherein, in the formula 1,

X₁₁is N or C (R)₁₁)，X₁₂Is N or C (R)₁₂)，X₁₃Is N or C (R)₁₃)，X₁₄Is N or C (R)₁₄)，X₁₅Is N or C (R)₁₅)，X₁₆Is N or C (R)₁₆)，X₁₇Is N or C (R)₁₇)，X₁₈Is N or C (R)₁₈)，

X₂₁Is N or C (R)₂₁)，X₂₂Is N or C (R)₂₂)，X₂₃Is N or C (R)₂₃)，X₂₄Is N or C (R)₂₄)，X₂₅Is N or C (R)₂₅)，X₂₆Is N or C (R)₂₆)，X₂₇Is N or C (R)₂₇)，X₂₈Is N or C (R)₂₈)，

L₁₁Is a group represented by the formula 2,

L₁₂is a group represented by one of formulas 3 and 4,

L₁₃is a group represented by one of formulas 2 to 4,

wherein in the formulae 2 to 4,

ring A₃To ring A₅Each independently is C₅-C₆₀Carbocyclic group or C₂-C₆₀A heterocyclic group,

R₁₁-R₁₈、R₂₁-R₂₈、R₃₀、R₄₀and R₅₀Each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C₁-C₆₀Alkyl, substituted or unsubstituted C₂-C₆₀Alkenyl, substituted or unsubstituted C₂-C₆₀Alkynyl, substituted or unsubstituted C₁-C₆₀Alkoxy, substituted or unsubstituted C₃-C₁₀Cycloalkyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkyl, substituted or unsubstituted C₃-C₁₀Cycloalkenyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₆-C₆₀Aryloxy, substituted or unsubstituted C₆-C₆₀Arylthio, substituted or unsubstituted C₁-C₆₀Heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic radical, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic radical, -Si (Q)₁)(Q₂)(Q₃)、-N(Q₄)(Q₅) or-B (Q)₆)(Q₇)，

R₃₀、R₄₀And R₅₀At least one of which is a cyano group,

a30, a40, and a50 are each independently integers from 1 to 10,

each of and represents a binding site to an adjacent atom, and

substituted C₁-C₆₀Alkyl, substituted C₂-C₆₀Alkenyl, substituted C₂-C₆₀Alkynyl, substituted C₁-C₆₀Alkoxy, substituted C₃-C₁₀Cycloalkyl, substituted C₂-C₁₀Heterocycloalkyl, substituted C₃-C₁₀Cycloalkenyl, substituted C₂-C₁₀Heterocycloalkenyl, substituted C₆-C₆₀Aryl, substituted C₆-C₆₀Aryloxy, substituted C₆-C₆₀Arylthio, substituted C₁-C₆₀At least one substituent of the heteroaryl, substituted monovalent non-aromatic fused polycyclic group, or substituted monovalent non-aromatic fused heteropolycyclic group is:

deuterium, -F, -Cl, -Br, -I, -CD₃、-CD₂H、-CDH₂、-CF₃、-CF₂H、-CFH₂Hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, or C₁-C₆₀An alkoxy group;

each independently selected from deuterium, -F, -Cl, -Br, -I, -CD₃、-CD₂H、-CDH₂、-CF₃、-CF₂H、-CFH₂Hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₁-C₆₀Heteroaryl, monovalent non-aromatic fused polycyclic radical, monovalent non-aromatic fused heteropolycyclic radical, -Si (Q)₁₁)(Q₁₂)(Q₁₃)、-N(Q₁₄)(Q₁₅) or-B (Q)₁₆)(Q₁₇) At least one substituted C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, or C₁-C₆₀An alkoxy group;

C₃-C₁₀cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀CycloalkenesBase, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₁-C₆₀A heteroaryl, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group;

each independently selected from deuterium, -F, -Cl, -Br, -I, -CD₃、-CD₂H、-CDH₂、-CF₃、-CF₂H、-CFH₂Hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₁-C₆₀Heteroaryl, monovalent non-aromatic fused polycyclic radical, monovalent non-aromatic fused heteropolycyclic radical, -Si (Q)₂₁)(Q₂₂)(Q₂₃)、-N(Q₂₄)(Q₂₅) or-B (Q)₂₆)(Q₂₇) At least one substituted C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₁-C₆₀A heteroaryl, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group; or

-Si(Q₃₁)(Q₃₂)(Q₃₃)、-N(Q₃₄)(Q₃₅) or-B (Q)₃₆)(Q₃₇)，

Wherein Q₁-Q₇、Q₁₁-Q₁₇、Q₂₁-Q₂₇And Q₃₁-Q₃₇Each of which isIndependently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C₁-C₆₀Alkyl, substituted or unsubstituted C₂-C₆₀Alkenyl, substituted or unsubstituted C₂-C₆₀Alkynyl, substituted or unsubstituted C₁-C₆₀Alkoxy, substituted or unsubstituted C₃-C₁₀Cycloalkyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkyl, substituted or unsubstituted C₃-C₁₀Cycloalkenyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₆-C₆₀Aryloxy, substituted or unsubstituted C₆-C₆₀Arylthio, substituted or unsubstituted C₁-C₆₀A heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

2. The heterocyclic compound according to claim 1, wherein X₁₁-X₁₈And X₂₁-X₂₈None is N, or X₁₁-X₁₈And X₂₁-X₂₈One or two of (a) are each N.

3. The heterocyclic compound according to claim 1, wherein ring a₃To ring A₅Each independently is a phenyl group, a naphthyl group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, a furan group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, a,Azole group, iso

4. The heterocyclic compound according to claim 1, wherein ring a₃To ring A₅Each independently is a phenyl group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, or a triazine group.

5. The heterocyclic compound according to claim 1, wherein

L₁₁Is one of the formulae O-1 to O-6,

L₁₂is one of the formulae M-1 to M-9 and P-1 to P-5, and

L₁₃is one of the formulae O-1 to O-6, M-1 to M-9, and P-1 to P-5:

wherein, in the formulae O-1 to O-6, M-1 to M-9, and P-1 to P-5,

R₃₀、R₄₀and R₅₀Are respectively defined as defined in claim 1,

d2 is an integer from 0 to 2,

d3 is an integer from 0 to 3,

d4 is an integer from 0 to 4, and

each of x and x' represents a binding site to an adjacent atom.

6. The heterocyclic compound according to claim 1, wherein R₁₁-R₁₈、R₂₁-R₂₈、R₃₀、R₄₀And R₅₀Each independently is

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₂₀Alkyl, or C₁-C₂₀An alkoxy group;

c each substituted by at least one group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, phenyl group, naphthyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, or triazinyl group₁-C₂₀Alkyl or C₁-C₂₀An alkoxy group;

cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenaphthenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, phenaenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo [9,10 ] phenanthrenyl]Phenanthryl, pyrenyl,A group selected from the group consisting of a phenyl group, a tetracenyl group, a picenyl group, a peryleneyl group, a pentylphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrAzolyl, benzimidazolyl, furyl, benzofuryl, thiophenePhenyl, benzothienyl, thiazolyl, isothiazolyl, benzothiazolyl, isothiazolylAzolyl group,

Each independently selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₂₀Alkyl radical, C₂-C₂₀Alkenyl radical, C₂-C₂₀Alkynyl, C₁-C₂₀Alkoxy, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, fluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, cinnolinyl, or quinazolinyl substituted with at least one cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptenylyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo [9,10]Phenanthryl, pyrenyl,

R₃₀、R₄₀and R₅₀At least one of (a) is cyano.

7. The heterocyclic compound according to claim 1, wherein R₁₁-R₁₈、R₂₁-R₂₈、R₃₀、R₄₀And R₅₀Each independently is

Hydrogen, deuterium, cyano, C₁-C₂₀Alkyl, or C₁-C₂₀An alkoxy group;

c each substituted by at least one member selected from deuterium, cyano, phenyl, biphenyl, terphenyl, or naphthyl₁-C₂₀Alkyl or C₁-C₂₀An alkoxy group;

cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl; or

Each being selected from deuterium, cyano, C₁-C₂₀Alkyl radical, C₁-C₂₀At least one substituted cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptene of alkoxy, phenyl, biphenyl, terphenyl, or naphthylPhenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, or dibenzothienyl, or

R₃₀、R₄₀And R₅₀At least one of (a) is cyano.

8. The heterocyclic compound according to claim 1, wherein R₃₀、R₄₀And R₅₀Each independently is hydrogen or cyano, and R₃₀、R₄₀And R₅₀At least one of (a) is cyano.

9. The heterocyclic compound according to claim 1, wherein the number of cyano groups included in the heterocyclic compound represented by formula 1 is 1 to 4.

10. The heterocyclic compound according to claim 1, wherein R₁₁-R₁₈And R₂₁-R₂₈None is cyano, or R₁₁-R₁₈And R₂₁-R₂₈Each is cyano; r₃₀、R₄₀And R₅₀One, two or three of (a) are each cyano; and the number of cyano groups included in the heterocyclic compound represented by formula 1 is 1 to 4.

11. The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by formula 1 is represented by one of formulae 10-1 to 10-6:

wherein, in formulae 10-1 to 10-6,

X₁₁-X₁₈and X₂₁-X₂₈Respectively as defined in claim 1,

X₃₁is N or C (R)₃₁)，X₃₂Is N or C (R)₃₂)，X₃₃Is N or C (R)₃₃)，X₃₄Is N or C (R)₃₄)，

X₄₁Is N or C (R)₄₁)，X₄₂Is N or C (R)₄₂)，X₄₃Is N or C (R)₄₃)，X₄₄Is N or C (R)₄₄)，X₄₅Is N or C (R)₄₅)，

X₅₁Is N or C (R)₅₁)，X₅₂Is N or C (R)₅₂)，X₅₃Is N or C (R)₅₃)，X₅₄Is N or C (R)₅₄)，

R₃₁-R₃₄Each of which is as defined in claim 1₃₀The same is defined in the same way,

R₄₁-R₄₅each of which is as defined in claim 1₄₀The same is defined in the same way,

R₅₁-R₅₄each of which is as defined in claim 1₅₀Are identically defined, and

R₃₁-R₃₄、R₄₁-R₄₅and R₅₁-R₅₄At least one of (a) is cyano.

12. The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by formula 1 is one of compounds 152, 224, 404, 582, 670, 813, 857, 2168, and 2451:

13. an organic light emitting device, comprising:

a first electrode;

a second electrode; and

an organic layer between the first electrode and the second electrode, the organic layer including an emission layer and including at least one heterocyclic compound represented by formula 1 as set forth in any one of claims 1 to 12.

14. The organic light emitting device of claim 13, wherein the first electrode is an anode, the second electrode is a cathode, the organic layer comprises a hole transport region between the first electrode and the emissive layer and an electron transport region between the emissive layer and the second electrode, the hole transport region comprises at least one of a hole injection layer, a hole transport layer, and an electron blocking layer, and the electron transport region comprises at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.

15. The organic light emitting device of claim 14, wherein the emission layer comprises a heterocyclic compound represented by formula 1.

16. The organic light emitting device of claim 15, wherein the emission layer comprises a host and a dopant, and the host comprises a heterocyclic compound represented by formula 1, wherein a content of the host is greater than a content of the dopant.

17. The organic light emitting device of claim 15, wherein the emissive layer emits blue light having a maximum emission wavelength in a range of 410 nanometers (nm) -490 nm.

18. The organic light emitting device according to claim 14, wherein the hole transport region comprises a heterocyclic compound represented by formula 1.

19. The organic light emitting device of claim 14, wherein the electron transport region comprises a heterocyclic compound represented by formula 1.

20. The organic light emitting device of claim 14, wherein the electron transport region comprises a hole blocking layer, the hole blocking layer is in direct contact with the emissive layer, and the hole blocking layer comprises a heterocyclic compound represented by formula 1.

Technical Field

The present disclosure relates to a heterocyclic compound and an organic light emitting device including the same.

Background

Organic Light Emitting Devices (OLEDs) are self-emissive devices that have a wide viewing angle, high contrast, short response time, and excellent luminance, driving voltage, and response speed characteristics and produce full-color images.

An OLED includes an anode, a cathode, and an organic layer between the anode and the cathode and including an emission layer. The hole transport region may be between the anode and the emissive layer, and the electron transport region may be between the emissive layer and the cathode. Holes supplied from the anode may move toward the emission layer through the hole transport region, and electrons supplied from the cathode may move toward the emission layer through the electron transport region. The holes and electrons recombine in the emission layer to generate excitons. These excitons transition from an excited state to a ground state to thereby generate light.

Disclosure of Invention

Provided are a heterocyclic compound and an organic light emitting device including the same.

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

According to an aspect of an embodiment, the heterocyclic compound may be represented by formula 1:

formula 1

Wherein, in the formula 1,

X₁₁can be N or C (R)₁₁)，X₁₂Can be N or C (R)₁₂)，X₁₃Can be N or C (R)₁₃)，X₁₄Can be N or C (R)₁₄)，X₁₅Can be N or C (R)₁₅)，X₁₆Can be N or C (R)₁₆)，X₁₇Can be N or C (R)₁₇)，X₁₈Can be N or C (R)₁₈)，

X₂₁Can be N or C (R)₂₁)，X₂₂Can be N or C (R)₂₂)，X₂₃Can be N or C (R)₂₃)，X₂₄Can be N or C (R)₂₄)，X₂₅Can be N or C (R)₂₅)，X₂₆Can be N or C (R)₂₆)，X₂₇Can be N or C (R)₂₇)，X₂₈Can be N or C (R)₂₈)，

L₁₁May be a group represented by formula 2,

L₁₂may be a group represented by one of formulas 3 and 4,

L₁₃may be a group represented by one of formulas 2 to 4,

wherein in the formulae 2 to 4,

ring A₃To ring A₅May each independently be C₅-C₆₀Carbocyclic group or C₂-C₆₀A heterocyclic group,

R₁₁-R₁₈、R₂₁-R₂₈、R₃₀、R₄₀and R₅₀Can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfoAcid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C₁-C₆₀Alkyl, substituted or unsubstituted C₂-C₆₀Alkenyl, substituted or unsubstituted C₂-C₆₀Alkynyl, substituted or unsubstituted C₁-C₆₀Alkoxy, substituted or unsubstituted C₃-C₁₀Cycloalkyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkyl, substituted or unsubstituted C₃-C₁₀Cycloalkenyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₆-C₆₀Aryloxy, substituted or unsubstituted C₆-C₆₀Arylthio, substituted or unsubstituted C₁-C₆₀Heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic radical, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic radical, -Si (Q)₁)(Q₂)(Q₃)、-N(Q₄)(Q₅) or-B (Q)₆)(Q₇)，

R₃₀、R₄₀And R₅₀At least one of (a) may be a cyano group,

a30, a40, and a50 may each independently be an integer from 1 to 10,

each of and represents a binding site to an adjacent atom, and

substituted C₁-C₆₀Alkyl, substituted C₂-C₆₀Alkenyl, substituted C₂-C₆₀Alkynyl, substituted C₁-C₆₀Alkoxy, substituted C₃-C₁₀Cycloalkyl, substituted C₂-C₁₀Heterocycloalkyl, substituted C₃-C₁₀Cycloalkenyl, substituted C₂-C₁₀Heterocycloalkenyl, substituted C₆-C₆₀Aryl, substituted C₆-C₆₀Aryloxy, substituted C₆-C₆₀Arylthio, substituted C₁-C₆₀Heteroaryl, substituted monovalent non-aromatic fused polycyclic group, or at least one substituent of substituted monovalent non-aromatic fused heteromulticyclic groupCan be as follows:

C₃-C₁₀cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₁-C₆₀A heteroaryl, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group;

each independently selected from deuterium, -F, -Cl, -Br, -I, -CD₃、-CD₂H、-CDH₂、-CF₃、-CF₂H、-CFH₂Hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₁-C₆₀Heteroaryl, monovalent non-aromatic fused polycyclic radical, monovalent non-aromatic fused heteropolycyclic radical, -Si (Q)₂₁)(Q₂₂)(Q₂₃)、-N(Q₂₄)(Q₂₅) or-B (Q)₂₆)(Q₂₇) At least one substituted C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₁-C₆₀A heteroaryl, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group; or

-Si(Q₃₁)(Q₃₂)(Q₃₃)、-N(Q₃₄)(Q₃₅) or-B (Q)₃₆)(Q₃₇)，

Wherein Q₁-Q₇、Q₁₁-Q₁₇、Q₂₁-Q₂₇And Q₃₁-Q₃₇Can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C₁-C₆₀Alkyl, substituted or unsubstituted C₂-C₆₀Alkenyl, substituted or unsubstituted C₂-C₆₀Alkynyl, substituted or unsubstituted C₁-C₆₀Alkoxy, substituted or unsubstituted C₃-C₁₀Cycloalkyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkyl, substituted or unsubstituted C₃-C₁₀Cycloalkenyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₆-C₆₀Aryloxy, substituted or unsubstituted C₆-C₆₀Arylthio, substituted or unsubstituted C₁-C₆₀A heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

According to an aspect of another embodiment, an organic light emitting device may include: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer and including at least one heterocyclic compound represented by formula 1.

Drawings

These and/or other aspects will become apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with the accompanying drawings.

Fig. 1 is a schematic cross-sectional view of an organic light emitting device according to an embodiment.

Detailed Description

Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to the like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as limited to the descriptions set forth herein. Accordingly, the embodiments are described below to illustrate aspects, only by referring to the drawings. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items. The expression "at least one of" when preceding or following a list of elements modifies the entire list of elements and does not modify individual elements of the list.

It will be understood that when an element is referred to as being "on" another element, it can be directly on the other element or intervening elements may be present. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements present.

It will be understood that, although the terms "first," "second," "third," etc. may be used herein to describe various elements, components, regions, layers and/or sections, these elements, components, regions, layers and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or section from another element, component, region, layer or section. Thus, a "first element," "component," "region," "layer" or "portion" discussed below could be termed a second element, component, region, layer or portion without departing from the teachings herein.

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, "a," "an," "the," and "at least one" do not denote a limitation of quantity, and are intended to cover both the singular and the plural, unless the context clearly indicates otherwise. For example, "an element" has the same meaning as "at least one element" unless the context clearly dictates otherwise.

"or" means "and/or". It will be further understood that the terms "comprises" and/or "comprising," when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.

Further, relative terms, such as "lower" or "bottom" and "upper" or "top," may be used herein to describe one element's relationship to another element as illustrated in the figures. It will be understood that relative terms are intended to encompass different orientations of the device in addition to the orientation depicted in the figures. For example, if the device in one of the figures is turned over, elements described as being on the "lower" side of other elements would then be oriented "on" the "upper" side of the other elements. Thus, the exemplary term "lower" can encompass both an orientation of "lower" and "upper," depending on the particular orientation of the figure. Similarly, if the device in one of the figures is turned over, elements described as "below" or "beneath" other elements would then be oriented "above" the other elements. Thus, the exemplary terms "above a.

As used herein, "about" or "approximately" includes the stated value and is meant to be within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art in view of the measurement in question and the error associated with measurement of the particular quantity (i.e., limitations of the measurement system). For example, "about" may mean a deviation from the stated value within one or more standard deviations, or within ± 30%, 20%, 10%, or 5%.

Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of this disclosure and the relevant art and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.

Exemplary embodiments are described herein with reference to cross-sectional views that are schematic illustrations of idealized embodiments. As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, the embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, regions illustrated or described as flat may typically have rough and/or non-linear features. Also, the sharp corners illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.

The heterocyclic compound may be represented by formula 1:

formula 1

Wherein, in formula 1, X₁₁Can be N or C (R)₁₁)，X₁₂Can be N or C (R)₁₂)，X₁₃Can be N or C (R)₁₃)，X₁₄Can be N or C (R)₁₄)，X₁₅Can be N or C (R)₁₅)，X₁₆Can be N or C (R)₁₆)，X₁₇Can be N or C (R)₁₇)，X₁₈Can be N or C (R)₁₈)，X₂₁Can be N or C (R)₂₁)，X₂₂Can be N or C (R)₂₂)，X₂₃Can be N or C (R)₂₃)，X₂₄Can be N or C (R)₂₄)，X₂₅Can be N or C (R)₂₅)，X₂₆Can be N or C (R)₂₆)，X₂₇Can be N or C (R)₂₇) And X₂₈Can be N or C (R)₂₈)。

In some embodiments, X₁₁-X₁₈And X₂₁-X₂₈None of which may be N, or X₁₁-X₁₈And X₂₁-X₂₈One or two of (a) may each be N.

In formula 1, L₁₁May be a group represented by formula 2, L₁₂May be a group represented by one of formulas 3 and 4, and L₁₃May be a group represented by one of formulae 2 to 4:

the heterocyclic compound represented by formula 1 may be represented with respect to L₁₃Is asymmetrical. Since the heterocyclic compound has an asymmetric structure, relatively excellent characteristics of an amorphous thin film can be secured.

In contrast, since a compound having a symmetric structure has high crystallinity, device characteristics may be deteriorated due to crystal formation of a material in a thin film during a process such as panel fabrication.

In formulae 2 to 4, ring A₃To ring A₅May each independently be C₅-C₆₀Carbocyclic group or C₂-C₆₀A heterocyclic group.

In some embodiments, ring a₃To ring A₅Can each independently be a phenyl group, a naphthyl group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, a furan group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, a,Azole group, iso

An azole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a quinoxaline group, a quinazoline group, a carbazole group, a benzimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiophene group, a benzophenon group

Azole group, isobenzo

An azole group, a triazole group, a tetrazole group,

An oxadiazole group, a triazine group, a dibenzofuran group, or a dibenzothiophene group.

In some embodiments, ring a₃To ring A₅May each independently be a phenyl group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, or a triazine group.

In some embodiments, L₁₁May be one of the formulae O-1 to O-6.

In some casesIn the embodiment, L₁₂May be of one of the formulae M-1 to M-9 and P-1 to P-5.

Additionally, in some embodiments, L₁₃Can be one of the formulae O-1 to O-6, M-1 to M-9, and P-1 to P-5:

wherein, in the formulae O-1 to O-6, M-1 to M-9, and P-1 to P-5,

R₃₀、R₄₀and R₅₀Can be understood by referring to the description thereof provided herein,

d2 can be an integer from 0-2,

d3 can be an integer from 0-3,

d4 can be an integer from 0 to 4, and

each of x and x' represents a binding site to an adjacent atom.

In some embodiments, in formula O-1, R₃₀May be hydrogen or cyano and R in the formulae O-2 to O-6₃₀May be hydrogen.

In some embodiments, R in formula M-1₄₀May be hydrogen or cyano, and R in the formulae M-2 to M-9₄₀May be hydrogen.

In some embodiments, R in formula P-1₅₀May be hydrogen or cyano, and R in the formulae P-2 to P-5₅₀May be hydrogen.

In formulae 1 to 4, R₁₁-R₁₈、R₂₁-R₂₈、R₃₀、R₄₀And R₅₀Can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C₁-C₆₀Alkyl, substituted or unsubstituted C₂-C₆₀Alkenyl, substituted or unsubstituted C₂-C₆₀Alkynyl, substituted or unsubstituted C₁-C₆₀Alkoxy, substituted or unsubstituted C₃-C₁₀Cycloalkyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkyl, substituted or unsubstituted C₃-C₁₀Cycloalkenyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₆-C₆₀Aryloxy, substituted or unsubstituted C₆-C₆₀Arylthio, substituted or unsubstituted C₁-C₆₀Heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic radical, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic radical, -Si (Q)₁)(Q₂)(Q₃)、-N(Q₄)(Q₅) or-B (Q)₆)(Q₇) And are and

R₃₀、R₄₀and R₅₀At least one of (a) may be a cyano group.

In some embodiments, R₁₁-R₁₈、R₂₁-R₂₈、R₃₀、R₄₀And R₅₀Can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₂₀Alkyl, or C₁-C₂₀An alkoxy group;

Azolyl, benzimidazolyl, furyl, benzofuryl, thienyl, benzothienyl, thiazolyl, isothiazolyl, benzothiazolyl, isothiazolyl

Azolyl group,Azolyl, triazolyl, tetrazolyl,A oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, imidazopyrimidinyl, or imidazopyridinyl group; or

A group selected from the group consisting of a phenyl group, a tetracenyl group, a picenyl group, a peryleneyl group, a pentylphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrAzolyl, benzimidazolyl, furyl, benzofuryl, thienyl, benzothienyl, thiazolyl, isothiazolyl, benzothiazolyl, isothiazolylAzolyl group,Azolyl, triazolyl, tetrazolyl,A diazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, imidazopyrimidinyl, or imidazopyridinyl group, and

R₃₀、R₄₀and R₅₀At least one of (a) may be a cyano group.

In some embodiments, R₁₁-R₁₈、R₂₁-R₂₈、R₃₀、R₄₀And R₅₀May each independently be hydrogen, deuterium, cyano, C₁-C₂₀Alkyl, or C₁-C₂₀An alkoxy group;

c each substituted by at least one member selected from deuterium, cyano, phenyl, biphenyl, terphenyl, or naphthyl₁-C₂₀Alkyl or C₁-C₂₀An alkoxy group;

cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl; or

Each being selected from deuterium, cyano, C₁-C₂₀Alkyl radical, C₁-C₂₀At least one substituted cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, or dibenzothienyl group of an alkoxy, phenyl, biphenyl, terphenyl, naphthyl, and

R₃₀、R₄₀and R₅₀At least one of (a) may be a cyano group.

In some embodiments, R₃₀、R₄₀And R₅₀May each independently be hydrogen or cyano, and

R₃₀、R₄₀and R₅₀At least one of (a) may be a cyano group.

In some embodiments, R₁₁-R₁₈、R₂₁-R₂₈、R₃₀、R₄₀And R₅₀May each independently be hydrogen or cyano, and

R₃₀、R₄₀and R₅₀At least one of (a) may be a cyano group.

In formulae 1 to 4, a30, a40, and a50 may each independently be an integer of 1 to 10.

a30 denotes R₃₀The number of (2); and when a30 is 2 or greater, at least two R₃₀May be the same as or different from each other. a40 denotes R₄₀The number of (2); and when a40 is 2 or greater, at least two R₄₀May be the same as or different from each other. a50 denotes R₅₀The number of (2); and when a50 is 2 or greater, at least two R₅₀May be the same as or different from each other.

In some embodiments, the number of cyano groups included in the heterocyclic compound represented by formula 1 may be 1 to 4.

In some embodiments, R₁₁-R₁₈And R₂₁-R₂₈None of which may be cyano, or R₁₁-R₁₈And R₂₁-R₂₈One or two ofMay each be cyano; r₃₀、R₄₀And R₅₀One, two or three of may each be cyano; and the number of cyano groups included in the heterocyclic compound represented by formula 1 may be 1 to 4.

In formulae 1 to 4, each of x and x' represents a binding site to an adjacent atom.

In some embodiments, the heterocyclic compound represented by formula 1 may be represented by one of formulae 10-1 to 10-6:

wherein, in formulae 10-1 to 10-6,

X₁₁-X₁₈and X₂₁-X₂₈Each can be understood by reference to the description thereof provided herein,

X₃₁can be N or C (R)₃₁)，X₃₂Can be N or C (R)₃₂)，X₃₃Can be N or C (R)₃₃)，X₃₄Can be N or C (R)₃₄)，

X₄₁Can be N or C (R)₄₁)，X₄₂Can be N or C (R)₄₂)，X₄₃Can be N or C (R)₄₃)，X₄₄Can be N or C (R)₄₄)，X₄₅Can be N or C (R)₄₅)，X₅₁Can be N or C (R)₅₁)，X₅₂Can be N or C (R)₅₂)，X₅₃Can be N or C (R)₅₃)，X₅₄Can be N or C (R)₅₄)，

R₃₁-R₃₄For R each as provided herein by reference₃₀The description is to be understood as an illustration,

R₄₁-R₄₅for R each as provided herein by reference₄₀The description is to be understood as an illustration,

R₅₁-R₅₄for R each as provided herein by reference₅₀Are understood to be the description of, and

R₃₁-R₃₄、R₄₁-R₄₅and R₅₁-R₅₄At least one of (a) may be a cyano group.

In some embodiments, X₃₁-X₃₄、X₄₁-X₄₅And X₅₁-X₅₄None of which may be N, or

X₃₁-X₃₄、X₄₁-X₄₅And X₅₁-X₅₄One or two of (a) may each be N.

Substituted C₁-C₆₀Alkyl, substituted C₂-C₆₀Alkenyl, substituted C₂-C₆₀Alkynyl, substituted C₁-C₆₀Alkoxy, substituted C₃-C₁₀Cycloalkyl, substituted C₂-C₁₀Heterocycloalkyl, substituted C₃-C₁₀Cycloalkenyl, substituted C₂-C₁₀Heterocycloalkenyl, substituted C₆-C₆₀Aryl, substituted C₆-C₆₀Aryloxy, substituted C₆-C₆₀Arylthio, substituted C₁-C₆₀At least one substituent of the heteroaryl, substituted monovalent non-aromatic fused polycyclic group, or substituted monovalent non-aromatic fused heteropolycyclic group may be:

each independently selected from deuterium, -F, -Cl, -Br, -I, -CD₃、-CD₂H、-CDH₂、-CF₃、-CF₂H、-CFH₂Hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereofPhosphoric acid group or salt thereof, C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₁-C₆₀Heteroaryl, monovalent non-aromatic fused polycyclic radical, monovalent non-aromatic fused heteropolycyclic radical, -Si (Q)₁₁)(Q₁₂)(Q₁₃)、-N(Q₁₄)(Q₁₅) or-B (Q)₁₆)(Q₁₇) At least one substituted C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, or C₁-C₆₀An alkoxy group;

each independently selected from deuterium, -F, -Cl, -Br, -I, -CD₃、-CD₂H、-CDH₂、-CF₃、-CF₂H、-CFH₂Hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₁-C₆₀Heteroaryl, monovalent non-aromatic fused polycyclic radical, monovalent non-aromatic fused heteropolycyclic radical, -Si (Q)₂₁)(Q₂₂)(Q₂₃)、-N(Q₂₄)(Q₂₅) or-B (Q)₂₆)(Q₂₇) At least one substituted C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₁-C₆₀A heteroaryl, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group; or

-Si(Q₃₁)(Q₃₂)(Q₃₃)、-N(Q₃₄)(Q₃₅) or-B (Q)₃₆)(Q₃₇)，

In one embodiment, the heterocyclic compound may be one of compounds 1 to 665, 667 to 2317, and 2320 to 2461:

the heterocyclic compound represented by formula 1 may include a terphenyl linker in which the ortho position of the benzene ring at one end of the terphenyl linker may be substituted with an N-carbazole group, and the meta or para position of the benzene ring at the other end thereof may be substituted with an N-carbazole group. Thus, steric hindrance may be generated asymmetrically. Therefore, in the heterocyclic compound represented by formula 1, relatively excellent characteristics of an amorphous thin film can be secured.

As described above, the heterocyclic compound represented by formula 1 may have electrical characteristics suitable for use as materials for an organic light emitting device, such as a host material, a hole transport material, and an electron transport material in an emission layer. Accordingly, an organic light emitting device including the heterocyclic compound may have high efficiency and/or long lifetime.

For example, some of the above-described compounds and comparative compounds were evaluated for Highest Occupied Molecular Orbital (HOMO), Lowest Unoccupied Molecular Orbital (LUMO), triplet state (T) by using a Gaussian program according to the Density Functional Theory (DFT) method (structural optimization at the level of B3LYP/6-31G (d, p))₁) And singlet state (S)₁) Energy level. The results are shown in table 1.

TABLE 1

As is apparent from Table 1, the heterocyclic compounds represented by formula 1 each have a relatively higher T₁Energy level. Accordingly, the heterocyclic compound represented by formula 1 may be suitably used as an emission layer material in an electronic device such as an organic light emitting device.

Methods of synthesizing the heterocyclic compounds represented by formula 1 can be understood by one of ordinary skill in the art by reference to the synthetic examples provided herein.

The heterocyclic compound represented by formula 1 may be suitably used as an organic layer material of an organic light emitting device, for example, an emission layer material, a hole transport region material, and/or an electron transport region material of the organic layer. Therefore, according to an aspect of another embodiment, an organic light emitting device may include: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer and including at least one heterocyclic compound represented by formula 1.

Since the organic light emitting device has an organic layer including the heterocyclic compound represented by formula 1, the organic light emitting device may have a low driving voltage, high efficiency, high luminance, high quantum efficiency, and a long lifetime.

In one embodiment, in the organic light emitting device,

the first electrode may be an anode, and the second electrode may be a cathode,

the organic layer may include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,

wherein the hole transport region may comprise a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and

the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof, but the embodiment is not limited thereto.

In one embodiment, the emission layer in the organic light emitting device may include at least one heterocyclic compound represented by formula 1.

In one embodiment, the emission layer in the organic light emitting device may include a host and a dopant, wherein the host may include at least one heterocyclic compound represented by formula 1, and the dopant may include a phosphorescent dopant or a fluorescent dopant. In some embodiments, the dopant may include a phosphorescent dopant (e.g., an organometallic compound represented by formula 81 provided herein). The host may further include any suitable host in addition to the heterocyclic compound represented by formula 1.

The emitting layer may emit red, green, or blue light.

In one embodiment, the emission layer may include a phosphorescent dopant, but the embodiment is not limited thereto.

In some embodiments, the heterocyclic compound represented by formula 1 may be included in a hole transport region of the organic light emitting device.

In some embodiments, the hole transport region of the organic light emitting device may include at least one of a hole injection layer, a hole transport layer, and an electron blocking layer, wherein the at least one of the hole injection layer, the hole transport layer, and the electron blocking layer may include a heterocyclic compound represented by formula 1.

In some embodiments, the heterocyclic compound represented by formula 1 may be included in an electron transport region of the organic light emitting device.

In some embodiments, the hole transport region of the organic light emitting device may include at least one of a hole blocking layer, an electron transport layer, and an electron injection layer, wherein the at least one of the hole blocking layer, the electron transport layer, and the electron injection layer may include a heterocyclic compound represented by formula 1.

In one embodiment, the hole transport region of the organic light emitting device may include an electron blocking layer, wherein the electron blocking layer may include a heterocyclic compound represented by formula 1. The electron blocking layer may be in direct contact with the emissive layer.

In one embodiment, the electron transport region of the organic light emitting device may include a hole blocking layer, wherein the hole blocking layer may include a heterocyclic compound represented by formula 1. The hole blocking layer may be in direct contact with the emissive layer.

In some embodiments, the organic layer of the organic light emitting device may further include an organometallic compound represented by formula 81, in addition to the heterocyclic compound represented by formula 1.

Formula 81

M(L₈₁)_n81(L₈₂)_n82

Formula 81A

Wherein, in the formulae 81 and 81A,

m may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh),

L₈₁may be a ligand represented by formula 81A, n81 may be an integer from 1 to 3; and when n81 is 2 or greater, at least two L₈₁May be the same as or different from each other,

L₈₂can be an organic ligand, n82 can be an integer from 0 to 4; and when n82 is 2 or greater, at least two L₈₂May be the same as or different from each other,

Y₈₁-Y₈₄may each independently be carbon (C) or nitrogen (N),

Y₈₁and Y₈₂May be connected to each other via a single or double bond, and Y₈₃And Y₈₄Can be connected to each other via a single bond or a double bond,

CY₈₁and CY₈₂May each independently be C₅-C₃₀Carbocyclic group or C₂-C₃₀A heterocyclic group,

CY₈₁and CY₈₂Optionally bound via an organic linking group,

R₈₁-R₈₅can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, -SF₅Substituted or unsubstituted C₁-C₆₀Alkyl, substituted or unsubstituted C₂-C₆₀Alkenyl, substituted or unsubstituted C₂-C₆₀Alkynyl, substituted or unsubstituted C₁-C₆₀Alkoxy, substituted or unsubstituted C₃-C₁₀Cycloalkyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkyl, substituted or unsubstituted C₃-C₁₀Cycloalkenyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₆-C₆₀Aryloxy, substituted or unsubstituted C₆-C₆₀Arylthio, substituted or unsubstitutedC₁-C₆₀Heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic radical, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic radical, -Si (Q)₈₁)(Q₈₂)(Q₈₃)、-N(Q₈₄)(Q₈₅)、-B(Q₈₆)(Q₈₇) or-P (═ O) (Q)₈₈)(Q₈₉)，

a81-a83 can each independently be an integer from 0-5,

when a81 is 2 or greater, at least two R₈₁May be the same as or different from each other,

when a82 is 2 or greater, at least two R₈₂May be the same as or different from each other,

when a81 is 2 or more, two adjacent R₈₁May optionally combine to form saturated or unsaturated C₂-C₃₀A ring (e.g., a benzene ring, a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a cyclohexene ring, a norbornane ring, a naphthalene ring, a benzindene ring, a benzindole ring, a benzofuran ring, a benzothiophene ring, a pyridine ring, a pyrimidine ring, or a pyrazine ring), or substituted with at least one R₈₈Substituted saturated or unsaturated C₂-C₃₀Rings (e.g. each with at least one R)₈₈A substituted benzene ring, cyclopentane ring, cyclohexane ring, cyclopentene ring, cyclohexene ring, norbornane ring, naphthalene ring, benzindene ring, benzindole ring, benzofuran ring, benzothiophene ring, pyridine ring, pyrimidine ring, or pyrazine ring),

when a82 is 2 or more, two adjacent R₈₂May optionally combine to form saturated or unsaturated C₂-C₃₀A ring (e.g., a benzene ring, a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a cyclohexene ring, a norbornane ring, a naphthalene ring, a benzindene ring, a benzindole ring, a benzofuran ring, a benzothiophene ring, a pyridine ring, a pyrimidine ring, or a pyrazine ring), or substituted with at least one R₈₉Substituted saturated or unsaturated C₂-C₃₀Rings (e.g. each with at least one R)₈₉Substituted benzene ring, cyclopentane ring, cyclohexane ring, cyclopentene ring, cyclohexene ring, norbornane ring, naphthalene ring, benzoindene ring, benzoindole ring, benzofuran ring, benzeneA bithiophene ring, a pyridine ring, a pyrimidine ring, or a pyrazine ring),

R₈₈can be obtained by reference to the description provided herein for R₈₁The description is to be understood as an illustration,

R₈₉can be obtained by reference to the description provided herein for R₈₂The description is to be understood as an illustration,

each of ×, and ×' in formula 81A represent a binding site to M in formula 81, and

said substituted C₁-C₆₀Alkyl, substituted C₂-C₆₀Alkenyl, substituted C₂-C₆₀Alkynyl, substituted C₁-C₆₀Alkoxy, substituted C₃-C₁₀Cycloalkyl, substituted C₂-C₁₀Heterocycloalkyl, substituted C₃-C₁₀Cycloalkenyl, substituted C₂-C₁₀Heterocycloalkenyl, substituted C₆-C₆₀Aryl, substituted C₆-C₆₀Aryloxy, substituted C₆-C₆₀Arylthio, substituted C₁-C₆₀At least one substituent of the heteroaryl, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be:

deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₁-C₆₀A heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or-Si (Q)₉₁)(Q₉₂)(Q₉₃)，

Wherein Q₈₁-Q₈₉And Q₉₁-Q₉₃May each independently be hydrogen, deuterium, C₁-C₆₀Alkyl radical, C₁-C₆₀Alkoxy radical, C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₁-C₆₀A heteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group.

In one embodiment, in formula 81A,

a83 can be 1 or 2, and

R₈₃-R₈₅may each independently be-CH₃、-CD₃、-CD₂H、-CDH₂、-CH₂CH₃、-CH₂CD₃、-CH₂CD₂H、-CH₂CDH₂、-CHDCH₃、-CHDCD₂H、-CHDCDH₂、-CHDCD₃、-CD₂CD₃、-CD₂CD₂H. or-CD₂CDH₂；

N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

Each being selected from deuterium, C₁-C₁₀An n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, or a naphthyl group substituted with at least one of an alkyl group or a phenyl group, but the embodiment is not limited thereto.

In some embodiments, in formula 81A,

Y₈₁can be N, Y₈₂And Y₈₃Can be respectively C, Y₈₄Can be N or C, and

CY₈₁and CY₈₂Can each independently be a cyclopentadiene group, a benzene group, a heptylene group, an indene group, a naphthalene group, an azulene group, a heptylene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a non-spirobifluorene groupA phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a benzo [9,10 ]]Phenanthrene group, pyrene group,

A group, a tetracenyl group, a pyrenyl group, a perylene group, a pentacenyl group, an hexacenyl group, a pentylene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, an isoindolyl group, an indole group, an indazole group, a pyrazole group, an imidazole group, a triazole group, a perylene group, a pentacene group, a perylene group, a rubicene group,

azole group, isoAn azole group,An oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a purine group, a furan group, a thiophene group, a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiazole group, a benzoAzole group, isobenzoAn azole group, a benzocarbazole group, a dibenzocarbazole group, an imidazopyridine group, an imidazopyrimidine group, a dibenzofuran group, a dibenzothiophene sulfone group, a carbazole group, a dibenzothiaole group, or a 2, 3-dihydro-1H-imidazole group.

In some embodiments, in formula 81A, Y₈₁Can be N, Y₈₂-Y₈₄May each be C, CY₈₁May be made of two N atomsIs a 5-membered ring of ring-forming atoms, and CY₈₂May be a phenyl group, a naphthyl group, a fluorene group, a dibenzofuran group, or a dibenzothiophene group, but the embodiment is not limited thereto.

In some embodiments, in formula 81A, Y₈₁Can be N, Y₈₂-Y₈₄May each be C, CY₈₁Can be an imidazole group or a 2, 3-dihydro-1H-imidazole group, and CY₈₂May be a phenyl group, a naphthyl group, a fluorene group, a dibenzofuran group, or a dibenzothiophene group, but the embodiment is not limited thereto.

In some embodiments, in formula 81A,

Y₈₁can be N, Y₈₂-Y₈₄Can be respectively C, and can be C,

CY₈₁can be pyrrole group, pyrazole group, imidazole group, triazole group,Azole group, iso

An azole group,

An oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a benzimidazole group, an isobenzothiazole group, a benzoquinone groupAzole group, or isobenzo

An azole group, and

CY₈₂can be a cyclopentadiene group, a benzene group, a naphthalene group, a fluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, an anthracene group, a benzo [9,10 ] group]Phenanthrene group, pyrene group,A group, a perylene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene sulfone group, a carbazole group, or a dibenzothiaole group.

In some embodiments, in formula 81A,

R₈₁and R₈₂May be each independently of the other

cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo [9,10 ] benzo]Phenanthryl, pyrenyl,A group selected from the group consisting of a pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl,Azolyl radical, iso

Oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzofuranyl, benzothienyl

Azolyl radical, isobenzoylAzolyl, triazolyl, tetrazolyl,A oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl group;

A group selected from the group consisting of a pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl,

Azolyl radical, isoOxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzofuranyl, benzothienyl

Azolyl radical, isobenzoylAzolyl, triazolyl, tetrazolyl,At least one substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthenyl, benzo [9,10 ] benzo group of oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl group]Phenanthryl, pyrenyl,A group selected from the group consisting of a pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl,

Azolyl radical, iso

Oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranylBenzothienyl, isobenzothiazolyl, benzoAzolyl radical, isobenzoyl

Azolyl, triazolyl, tetrazolyl,

A oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl group; or

-B(Q₈₆)(Q₈₇) or-P (═ O) (Q)₈₈)(Q₈₉)，

Wherein Q₈₆-Q₈₉Can each independently be

-CH₃、-CD₃、-CD₂H、-CDH₂、-CH₂CH₃、-CH₂CD₃、-CH₂CD₂H、-CH₂CDH₂、-CHDCH₃、-CHDCD₂H、-CHDCDH₂、-CHDCD₃、-CD₂CD₃、-CD₂CD₂H. or-CD₂CDH₂；

N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

Each being selected from deuterium, C₁-C₁₀An n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, or a naphthyl group, substituted with at least one of an alkyl group or a phenyl group.

In some embodiments, in formula 81A, R is selected from the number a81₈₁And R in an amount of a82₈₂At least one of (a) may be a cyano group.

In some embodiments, in formula 81A, R is selected from the number a82₈₂At least one of (a) may be a cyano group.

In some embodiments, in formula 81A, the number of R is a81₈₁And R in an amount of a82₈₂At least one of (a) and (b) may be deuterium.

In some embodiments, in formula 81, L₈₂May be a ligand represented by one of formulae 3-1(1) to 3-1(69), 3-1(71) to 3-1(79), 3-1(81) to 3-1(88), 3-1(91) to 3-1(98), and 3-1(101) to 3-1 (114):

wherein, in formulas 3-1(1) to 3-1(69), 3-1(71) to 3-1(79), 3-1(81) to 3-1(88), 3-1(91) to 3-1(98), and 3-1(101) to 3-1(114),

X₁can be O, S, C (Z)₂₁)(Z₂₂) Or N (Z)₂₃)，

X₃₁Can be N or C (Z)_1a)，X₃₂Can be N or C (Z)_1b)，

X₄₁Can be O, S, N (Z)_1a) Or C (Z)_1a)(Z_1b)，

Z₁-Z₄、Z_1a、Z_1b、Z_1c、Z_1d、Z_2a、Z_2b、Z_2c、Z_2d、Z₁₁-Z₁₄And Z₂₁-Z₂₃Can each independently be

A group selected from the group consisting of a pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl,

Azolyl radical, iso

Oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalyl, quinazolineCinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzofuranylAzolyl radical, isobenzoylAzolyl, triazolyl, tetrazolyl,A oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl group;

Azolyl radical, iso

Oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalyl, quinazolinyl, cinnolinyl, carbazolyl, oxazolyl, quinoxalinyl, cinnolinyl, and pyrazolyl,Phenanthroline, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo

Azolyl radical, isobenzoyl

Azolyl, triazolyl, tetrazolyl,At least one substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthenyl, benzo [9,10 ] benzo group of oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl group]Phenanthryl, pyrenyl,

A group selected from the group consisting of a pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl,Azolyl radical, iso

A oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl group; or

-B(Q₈₆)(Q₈₇) or-P (═ O) (Q)₈₈)(Q₈₉)，

Wherein Q₈₆-Q₈₉Can each independently be

-CH₃、-CD₃、-CD₂H、-CDH₂、-CH₂CH₃、-CH₂CD₃、-CH₂CD₂H、-CH₂CDH₂、-CHDCH₃、-CHDCD₂H、-CHDCDH₂、-CHDCD₃、-CD₂CD₃、-CD₂CD₂H. or-CD₂CDH₂；

N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

Each being selected from deuterium, C₁-C₁₀An n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, or a naphthyl group, substituted with at least one of an alkyl group or a phenyl group,

d2 and e2 may each independently be 0 or 2,

e3 can be an integer from 0-3,

d4 and e4 may each independently be an integer from 0 to 4,

d6 and e6 may each independently be an integer from 0 to 6,

d8 and e8 may each independently be an integer from 0 to 8, and

each of x and x' represents a binding site to M in formula 1.

In some embodiments, in formula 81, M may be Ir, and the sum of n81 and n82 may be 3. In some embodiments, in formula 81, M may be Pt and the sum of n81 and n82 may be 2.

In some embodiments, the organometallic compound represented by formula 81 may be neutral and may not include an ion pair of a cation and an anion.

In some embodiments, the organometallic compound represented by formula 81 may include at least one of the compounds PD1 to PD78 or FIr6, but the embodiments are not limited thereto:

as used herein, "(e.g., the organic layer) includes at least one heterocyclic compound" means "(the organic layer) includes (one) heterocyclic compound of formula 1, or at least two different heterocyclic compounds of formula 1.

For example, the organic layer may include only compound 1 as the heterocyclic compound. In this embodiment, the compound 1 may be included in an emission layer of the organic light emitting device. In some embodiments, the organic layer may include compounds 1 and 2 as the heterocyclic compound. In this embodiment, compounds 1 and 2 may be present in the same layer (e.g., compounds 1 and 2 may both be present in the emissive layer), or in different layers (e.g., compound 1 may be present in the emissive layer, and compound 2 may be present in the hole blocking layer).

The first electrode may be an anode as a hole injection electrode, and the second electrode may be a cathode as an electron injection electrode. In some embodiments, the first electrode may be a cathode as an electron injection electrode, and the second electrode may be an anode as a hole injection electrode.

The term "organic layer" as used herein refers to a single and/or multiple layers between a first electrode and a second electrode of an organic light emitting device. The "organic layer" may include not only an organic compound but also an organometallic complex including a metal.

Fig. 1 illustrates a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment. Hereinafter, a structure of an organic light emitting device and a method of manufacturing the organic light emitting device according to one or more embodiments will be described with reference to fig. 1. The organic light emitting device 10 may include a first electrode 11, an organic layer 15, and a second electrode 19, which may be sequentially stacked in the order set forth.

A substrate may additionally be provided under the first electrode 11 or on the second electrode 19. The substrate may be a conventional substrate used in an organic light emitting device, for example, a glass substrate or a transparent plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, easy operability, and water resistance.

The first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 onto the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be a material having a high work function for easy hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin oxide (SnO)₂) And zinc oxide (ZnO). In one embodiment, the material for forming the first electrode 11 may be a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

The first electrode 11 may have a single-layer structure or a multi-layer structure including a plurality of layers. In some embodiments, the first electrode 11 may have a triple-layered structure of ITO/Ag/ITO, but the embodiments are not limited thereto.

The organic layer 15 may be on the first electrode 11.

The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.

The hole transport region may be disposed between the first electrode 11 and the emission layer.

The hole transport region may include at least one selected from a hole injection layer, a hole transport layer, and an electron blocking layer, and may optionally further include a buffer layer.

The hole transport region may include only a hole injection layer or only a hole transport layer. In some embodiments, the hole transport region may include a hole injection layer and a hole transport layer sequentially stacked on the first electrode 11. In some embodiments, the hole transport region may include a hole injection layer, a hole transport layer, and an electron blocking layer sequentially stacked on the first electrode 11.

When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, such as vacuum deposition, spin coating, casting, and langmuir-blodgett (LB) deposition.

When the hole injection layer is formed by vacuum deposition, for example, the vacuum deposition may be at a temperature in the range of about 100 ℃ to about 500 ℃ at about 10^-8Torr to about 10^-3Vacuum in the Torr range, and at about 0.01A/s-about

A rate in the range of/sec, although the conditions may vary depending on the compound used as the hole injection material and the desired structure and thermal properties of the hole injection layer, embodiments are not limited thereto.

When the hole injection layer is formed by spin coating, the spin coating may be performed at a rate ranging from about 2,000 revolutions per minute (rpm) to about 5,000rpm and at a temperature ranging from about 80 ℃ to 200 ℃ to facilitate removal of a solvent after the spin coating, although the conditions may vary depending on a compound used as a hole injection material and desired structure and thermal properties of the hole injection layer, but the embodiment is not limited thereto.

The conditions for forming the hole transport layer and the electron blocking layer can be inferred from the conditions for forming the hole injection layer.

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

formula 202

Wherein, in formula 201, Ar₁₀₁And Ar₁₀₂Can each independently be

Phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, acenaphthylene, fluorenylene, phenalenylene, phenanthrylene, anthrylene, benzo [9,10 ] ene]Phenanthrylene, pyrenylene

A phenyl group, a biphenylene group, or a biphenylene group; or

Each independently selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₁₀Cycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₁-C₆₀At least one substituted phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptenylene, acenaphthylene, fluorenylene, phenalenylene, phenanthrenylene, anthrylene, fluoranthrylene, benzo [9,10 ] ene of a heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group]Phenanthrylene, pyrenyleneA phenylene group, a tetracylene group, a picylene group, a peryleneylene group, or a pentacylene group.

In formula 201, xa and xb may each independently be an integer of 0 to 5. In some embodiments, xa and xb may each independently be an integer from 0 to 2. In some embodiments, xa may be 1 and xb may be 0, but embodiments are not limited thereto.

In formulae 201 and 202, R₁₀₁-R₁₀₈、R₁₁₁-R₁₁₉And R₁₂₁-R₁₂₄Can each independently be

c each substituted by at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, or phosphoric acid group or salt thereof₁-C₁₀Alkyl and C₁-C₁₀An alkoxy group;

phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl; or

Each independently selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acidGroup or salt thereof, phosphoric acid group or salt thereof, C₁-C₁₀Alkyl, or C₁-C₁₀At least one substituted phenyl group, naphthyl group, anthracenyl group, fluorenyl group, and pyrenyl group of the alkoxy group, but the embodiment is not limited thereto.

In formula 201, R₁₀₉Can be

Phenyl, naphthyl, anthracenyl, or pyridyl; or

In some embodiments, the compound represented by formula 201 may be represented by formula 201A, but embodiments are not limited thereto:

formula 201A

Wherein, in formula 201A, R₁₀₁、R₁₁₁、R₁₁₂And R₁₀₉May be understood by referring to the description thereof provided herein, respectively.

In some embodiments, the compounds represented by formulas 201 and 202 may include compounds HT1 through HT20, but embodiments are not limited thereto:

the hole transport region can have a thickness of about 100 angstroms-about

For example about-about

Within the range of (1). When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the hole injection layer may have a thickness of about-about

For example about

-aboutIn the range of (1), the hole transport layer may have a thickness of about-aboutFor example about

-about

Within the range of (1). When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within any of these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage.

In addition to the foregoing materials, the hole transport region may further include a charge generation material to improve the conductive properties of the hole transport region. The charge generating material may be substantially uniformly or non-uniformly dispersed in the hole transport region.

The charge generating material may include, for example, a p-dopant. The p-dopant may include one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but the embodiment is not limited thereto. For example, non-limiting examples of the p-dopant include quinone derivatives such as Tetracyanoquinodimethane (TCNQ) or 2,3,5, 6-tetrafluoro-tetracyano-1, 4-benzoquinodimethane (F4-TCNQ); metal oxides such as tungsten oxide or molybdenum oxide; and cyano group-containing compounds such as compound HT-D1 or compound HT-D2, but the embodiments are not limited thereto:

the hole transport region may further include a buffer layer.

The buffer layer may compensate for an optical resonance distance depending on a wavelength of light emitted from the emission layer to improve efficiency of the organic light emitting device.

An emissive layer can be formed on the hole transport region by using one or more suitable methods, such as vacuum deposition, spin coating, casting, or LB deposition. When the emission layer is formed by vacuum deposition or spin coating, the vacuum deposition and spin coating conditions for forming the emission layer may be generally similar to those for forming the hole injection layer, although the conditions may vary depending on the compound used.

The hole transport region may further include an electron blocking layer. The electron blocking layer may include any suitable known material such as mCP, but embodiments are not limited thereto:

the electron blocking layer may have a thickness of about-aboutAnd in some embodiments about-aboutWithin the range of (1). When the thickness of the electron blocking layer is within any of these ranges, excellent electron blocking characteristics can be obtained without a significant increase in driving voltage.

When the organic light emitting device 10 is a full color organic light emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer. In one embodiment, the emission layer may have a structure in which a red emission layer, a green emission layer, and/or a blue emission layer are stacked to emit white light. In some embodiments, the structure of the emissive layer may vary.

The emission layer may include a heterocyclic compound represented by formula 1.

In some embodiments, the emission layer may include only the heterocyclic compound represented by formula 1.

In some embodiments, the emissive layer may comprise

A heterocyclic compound represented by the formula 1, and

i) a second compound;

ii) an organometallic compound represented by the formula 81; or

iii) any combination of i) and ii).

The heterocyclic compound represented by formula 1, the second compound, and the organometallic compound represented by formula 81 may be understood by referring to the descriptions for those provided herein, respectively.

When the emission layer includes the host and the dopant, the amount of the dopant may be in the range of about 0.01 parts by weight to about 20 parts by weight based on about 100 parts by weight of the emission layer, but the embodiment is not limited thereto. When the amount of the dopant is within this range, light emission can be achieved without quenching.

When the emission layer includes the heterocyclic compound represented by formula 1 and the second compound, the weight ratio of the heterocyclic compound represented by formula 1 to the second compound may be in the range of about 1:99 to about 99:1, for example, about 70:30 to about 30: 70. In some embodiments, the weight ratio of the heterocyclic compound represented by formula 1 to the second compound may be in the range of about 60:40 to about 40: 60. When the weight ratio of the heterocyclic compound represented by formula 1 to the second compound in the emission layer is within any of these ranges, charge transport balance can be effectively achieved in the emission layer.

The thickness of the emissive layer may be about-about

And in some embodiments about

-aboutWithin the range of (1). When the thickness of the emission layer is within any of these ranges, improved light emission characteristics may be obtained without a significant increase in driving voltage.

Then, an electron transport region may be formed on the emission layer.

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

In some embodiments, the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure, but the embodiments are not limited thereto. The electron transport layer may have a multilayer structure or a single layer structure including two or more different materials.

The conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer may be inferred based on the conditions for forming the hole injection layer.

When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP and Bphen, but the embodiment is not limited thereto:

the hole blocking layer may include a heterocyclic compound represented by formula 1.

The hole blocking layer may have a thickness of about-aboutFor example about-about

Within the range of (1). When the thickness of the hole blocking layer is within any of these ranges, excellent hole blocking characteristics can be obtained without a significant increase in driving voltage.

The electron transport layer may further comprise a material selected from BCP, Bphen, Alq₃At least one of BAlq, TAZ, or NTAZ:

in some embodiments, the electron transport layer may include at least one selected from compounds ET1, ET2, and ET3, but embodiments are not limited thereto:

the electron transport layer may have a thickness of about

-aboutAnd in some embodiments about-about

Within the range of (1). When the thickness of the electron transport layer is within any of these ranges, excellent electron transport characteristics can be obtained without a significant increase in driving voltage.

In addition to the materials described above, the electron transport layer may further include a material including a metal.

The metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1(LiQ) or compound ET-D2:

the electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 19.

The electron injection layer may include one or more selected from LiQ, LiF, NaCl, CsF, Li₂At least one of O, or BaO.

The electron injection layer may have a thickness of about

-aboutAnd in some embodiments about

-about

Within the range of (1). When the thickness of the electron injection layer is within any of these ranges, excellent electron injection characteristics can be obtained without a significant increase in driving voltage.

The second electrode 19 may be on the organic layer 15. The second electrode 19 may be a cathode. The material for forming the second electrode 19 may be a material having a relatively low work function such as a metal, an alloy, a conductive compound, and a mixture thereof. Examples of the material for forming the second electrode 19 may include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). In some embodiments, ITO or IZO may be used to form the transmissive second electrode 19 to fabricate a top emission light emitting device. In some embodiments, the material used to form the second electrode 19 may vary.

In the above, the organic light emitting device 10 has been described with reference to fig. 1, but the embodiment is not limited thereto.

The term "C" as used herein₁-C₆₀Alkyl "refers to a straight or branched aliphatic saturated hydrocarbon monovalent radical having 1 to 60 carbon atoms. Examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. The term "C" as used herein₁-C₆₀Alkylene "means having a bond with C₁-C₆₀Alkyl groups are divalent radicals of the same structure.

The term "C" as used herein₁-C₆₀Alkoxy "refers to a group consisting of-OA₁₀₁A monovalent group of (wherein A)₁₀₁Is C₁-C₆₀Alkyl groups). Examples thereof include methoxy, ethoxy, and isopropoxy.

The term "C" as used herein₂-C₆₀Alkenyl "is defined by the presence of C₂-C₆₀A group formed by disposing at least one carbon-carbon double bond in the middle or at the end of the alkyl group. Examples thereof include ethenyl, propenyl, and butenyl. The term "C" as used herein₂-C₆₀Alkenylene radical "Means having a radical with C₂-C₆₀Divalent radicals of the same structure as the alkenyl radicals.

The term "C" as used herein₂-C₆₀Alkynyl "is intended by the presence of C₂-C₆₀A group formed by placing at least one carbon-carbon triple bond in the middle or at the end of the alkyl group. Examples thereof include ethynyl and propynyl. The term "C" as used herein₂-C₆₀Alkynylene "means having a bond with C₂-C₆₀Alkynyl groups are divalent radicals of the same structure.

The term "C" as used herein₃-C₁₀Cycloalkyl "refers to a monovalent monocyclic saturated hydrocarbon group comprising 3-10 carbon atoms. Examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. The term "C" as used herein₃-C₁₀Cycloalkylene "means having an alkyl radical with C₃-C₁₀A divalent group of the same structure as the cycloalkyl group.

The term "C" as used herein₂-C₁₀Heterocycloalkyl "refers to a monovalent monocyclic group comprising at least one heteroatom selected from N, O, P, Si, Se, Ge, or S as a ring-forming atom and 2 to 10 carbon atoms. Examples thereof include tetrahydrofuranyl and tetrahydrothienyl. The term "C" as used herein₂-C₁₀Heterocycloalkylene "means having a carbon atom with₂-C₁₀Heterocycloalkyl groups are divalent radicals of the same structure.

The term "C" as used herein₃-C₁₀Cycloalkenyl "refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring, wherein the molecular structure as a whole is non-aromatic. Examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. The term "C" as used herein₃-C₁₀Cycloalkenyl "means having an alkyl group with C₃-C₁₀And (c) divalent groups having the same structure as the cycloalkenyl groups.

The term "C" as used herein₂-C₁₀Heterocycloalkenyl "means a compound comprising in its ring at least one member selected from N, O, P, Si, Se, Ge, or SThe heteroatom is a monovalent monocyclic group of ring-forming atoms, 2 to 10 carbon atoms, and at least one double bond. Said C is₂-C₁₀Examples of heterocycloalkenyl include 2, 3-dihydrofuranyl and 2, 3-dihydrothienyl. The term "C" as used herein₂-C₁₀Heterocycloalkenylene "means having a carbon atom with C₂-C₁₀Divalent radicals of the same structure as the heterocycloalkenyl radical.

The term "C" as used herein₆-C₆₀Aryl "refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. The term "C" as used herein₆-C₆₀Arylene "refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Said C is₆-C₆₀Examples of the aryl group include phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, and

and (4) a base. When C is present₆-C₆₀Aryl and C₆-C₆₀When each of the arylene groups includes a plurality of rings, the plurality of rings may be fused to each other.

The term "C" as used herein₁-C₆₀Heteroaryl "refers to a monovalent group having a heterocyclic aromatic system as follows: the heterocyclic aromatic system has at least one heteroatom selected from N, O, P, Si, Se, Ge, or S as a ring-forming atom and 1 to 60 carbon atoms. The term "C" as used herein₁-C₆₀Heteroarylene "refers to a divalent group having a heterocyclic aromatic system as follows: the heterocyclic aromatic system has at least one heteroatom selected from N, O, P, Si, Se, Ge, or S as a ring-forming atom and 1 to 60 carbon atoms. C₁-C₆₀Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C is present₁-C₆₀Heteroaryl and C₁-C₆₀When the heteroarylenes each include multiple rings, the multiple rings may be fused to each other.

The term "C" as used herein₆-C₆₀Aryloxy group "made of-OA₁₀₂(wherein A is₁₀₂Is C₆-C₆₀Aryl) group. The term "C" as used herein₆-C₆₀Arylthio radical' from-SA₁₀₃(wherein A is₁₀₃Is C₆-C₆₀Aryl) group.

The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group as follows: which has two or more fused rings and has only carbon atoms (for example, the number of carbon atoms may be in the range of 8 to 60) as ring-forming atoms, wherein the molecular structure as a whole is non-aromatic. Examples of the non-aromatic fused polycyclic group include fluorenyl groups. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic fused polycyclic group.

The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group as follows: having at least two fused rings, having heteroatoms of N, O, P, Si, Se, Ge, or S as ring-forming atoms in addition to carbon atoms (e.g., the number of carbon atoms may be in the range of 1-60), wherein the molecular structure as a whole is non-aromatic. Examples of the monovalent non-aromatic fused heteropolycyclic group include carbazolyl groups. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic fused heteropolycyclic group.

The term "C" as used herein₅-C₆₀The carbocyclic group "means a saturated or unsaturated cyclic group including only 5 to 60 carbon atoms as ring-constituting atoms. Said C is₅-C₆₀The carbocyclic group may be a monocyclic group or a polycyclic group.

The term "C" as used herein₂-C₆₀The heterocyclic group "means a saturated or unsaturated cyclic group including 2 to 60 carbon atoms and at least one hetero atom selected from N, O, P, Si, Se, Ge, or S as a ring-forming atom. Said C is₂-C₆₀The heterocyclic group may be a monocyclic group or a polycyclic group.

In this specificationIn the formula 1, substituted C₁-C₆₀Alkyl, substituted C₂-C₆₀Alkenyl, substituted C₂-C₆₀Alkynyl, substituted C₃-C₁₀Cycloalkyl, substituted C₂-C₁₀Heterocycloalkyl, substituted C₃-C₁₀Cycloalkenyl, substituted C₂-C₁₀Heterocycloalkenyl, substituted C₆-C₆₀Aryl, substituted C₆-C₆₀Aryloxy, substituted C₆-C₆₀Arylthio, substituted C₁-C₆₀At least one substituent of the heteroaryl, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be:

deuterium, -CD₃、-CD₂H、-CDH₂-F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, or C₁-C₆₀An alkoxy group;

each being selected from deuterium, -CD₃、-CD₂H、-CDH₂-F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₁-C₆₀Heteroaryl, monovalent non-aromatic fused polycyclic radical, monovalent non-aromatic fused heteropolycyclic radical, -Si (Q)₂₁)(Q₂₂)(Q₂₃)、-N(Q₂₄)(Q₂₅) or-B (Q)₂₆)(Q₂₇) At least one substituted C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₁-C₆₀A heteroaryl group, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group; or

-Si(Q₃₁)(Q₃₂)(Q₃₃)、-N(Q₃₄)(Q₃₅) or-B (Q)₃₆)(Q₃₇)，

Wherein Q₁₁-Q₁₇、Q₂₁-Q₂₇And Q₃₁-Q₃₇Can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C₁-C₆₀Alkyl, substituted or unsubstituted C₂-C₆₀Alkenyl, substituted or unsubstituted C₂-C₆₀Alkynyl, substituted or unsubstituted C₁-C₆₀Alkoxy, substituted or unsubstituted C₃-C₁₀Cycloalkyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkyl, substituted or unsubstituted C₃-C₁₀Cycloalkenyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₆-C₆₀Aryloxy, substituted or unsubstituted C₆-C₆₀Arylthio, substituted or unsubstituted C₁-C₆₀A heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

As used herein, the symbols and, unless otherwise defined, refer to binding sites to adjacent atoms in the formula.

Hereinafter, the heterocyclic compound and the organic light emitting device according to the embodiment will be described in detail with reference to synthesis examples and examples, however, the present disclosure is not limited thereto. The expression "using B instead of a" as used in describing the synthesis examples means that the same molar equivalents of B are used instead of a.

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Heterocyclic compound and organic light emitting device including the same

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