Heterocyclic compound, hole transport composition comprising the same, light emitting device comprising the same and method for manufacturing the same, and electonic apparatus

Abstract

A heterocyclic compound represented by Chemical Formula 1, a hole-transporting composition including the same, an organic light-emitting device including the same, a method for manufacturing the same, and an electronic device are disclosed: Refer to the present specification for the description of each substituent in Chemical Formula 1 above.

Description

Technology Field

[0001] The invention relates to a heterocyclic compound, a hole-transporting composition containing the same, a light-emitting device containing the same, a method for manufacturing the same, an electronic device compound containing the light-emitting device, and a light-emitting device containing the same. Background Technology

[0002] Organic light-emitting devices are self-emissive devices that, compared to conventional devices, not only have a wide viewing angle and excellent contrast, but also have a fast response time, excellent characteristics in brightness, driving voltage and response speed, and are capable of multi-color.

[0003] The above organic light-emitting device may have a structure in which a first electrode is disposed on a substrate, and a hole transport region, an emissive layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. Holes injected from the first electrode move to the emissive layer via the hole transport region, and electrons injected from the second electrode move to the emissive layer via the electron transport region. Carriers such as holes and electrons recombine in the emissive layer region to generate excitons. Light is generated as these excitons change from an excited state to a ground state. The problem to be solved

[0004] A novel heterocyclic compound, a hole-transporting composition containing the same, a light-emitting device containing the same, and a method for manufacturing the same are provided. Additionally, an electronic device including the light-emitting device is provided. means of solving the problem

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

[0006] <Chemical Formula 1>

[0007]

[0008] Among the above chemical formula 1,

[0009] L 11 to L 13 and L 21 to L 23 are independently of each other, a single bond, at least one R 10a C1-C substituted or unsubstituted 20 alkylene group, at least one R 10a C2-C substituted or unsubstituted 20 alkenylene group, or at least one R 10a C2-C substituted or unsubstituted 20 It is an alkynylene group, and

[0010] a11 to a13 and a21 to a23 are independently 0, 1, 2, 3, 4 or 5, and

[0011] Z 11 To Z 13 , Z 21 To Z 23 and R1 to R9 are independently hydrogen, deuterium, azide group (-N3), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazino group, hydrazono group, at least one R 10a C1-C substituted or unsubstituted 60 alkyl group, at least one R 10a C2-C substituted or unsubstituted 60 alkenyl group, at least one R 10a C2-C substituted or unsubstituted 60 alkynyl group, at least one R 10a C1-C substituted or unsubstituted 60 Alkoxy group, at least one R 10a C3-C substituted or unsubstituted 10 Cycloalkyl group, at least one R 10a C1-C substituted or unsubstituted 10 Heterocycloalkyl group, at least one R 10a C3-C substituted or unsubstituted 10Cycloalkenyl group, at least one R 10a C1-C substituted or unsubstituted 10 Heterocycloalkenyl group, at least one R 10a C6-C substituted or unsubstituted 60 Arylgi, at least one R 10a C6-C substituted or unsubstituted 60 aryloxy group, at least one R 10a C6-C substituted or unsubstituted 60 Arylthiogi, at least one R 10a C1-C substituted or unsubstituted 60 Heteroaryl group, at least one R 10a C1-C substituted or unsubstituted 60 Heteroaryloxy group, at least one R 10a C1-C substituted or unsubstituted 60 Heteroaryltio group, at least one R 10a A monovalent non-aromatic condensed polycyclic group substituted or unsubstituted with R, at least one R 10a A monovalent non-aromatic heterocondensed polycyclic group substituted or unsubstituted with -Si(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) or -P(=S)(Q1)(Q2), and

[0012] Z 11 To Z 13 , Z 21 To Z 23 and at least one of R1 to R9 is -N3, and

[0013] Z 11 To Z 13 In the case where all of these are -N3, -(L 21 ) a21 -Z 21 , -(L 22 ) a22 -Z 22 and -(L 23 ) a23 -Z 23At least one of them represents hydrogen, and

[0014] The above R 10a Is,

[0015] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, or nitro group;

[0016] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ), -P(=O)(Q 11 )(Q 12 ), or substituted or unsubstituted with any combination thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, or C1-C 60 Alkoxygenation;

[0017] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ), -P(=O)(Q 21 )(Q 22 ), or substituted or unsubstituted with any combination thereof, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 aryloxy group, or C6-C 60 Arylthiogi; or

[0018] -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), or -P(=O)(Q 31 )(Q 32 ); and,

[0019] The above Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 They are independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy group; or deuterium, -F, cyano group, C1-C 60 Alkyl group, C1-C 60 C3-C substituted or unsubstituted with an alkoxy group, a phenyl group, a biphenyl group, or any combination thereof 60 Carbocyclic group or C1-C 60 Heterocyclic group; and,

[0020] The above heterocyclic compound is not the following compound B:

[0021] <Compound B>

[0022] .

[0023] According to another aspect, a hole-transporting composition comprising the above-mentioned heterocyclic compound is provided.

[0024] According to another aspect, an organic light-emitting device is provided, comprising: a first electrode; a second electrode opposite to the first electrode; and an organic layer including a light-emitting layer interposed between the first electrode and the second electrode, wherein the heterocyclic compound; a polymer comprising repeating units derived from the heterocyclic compound; or any combination thereof.

[0025] According to another aspect, a method for manufacturing an organic light-emitting device is provided, comprising the step of forming a hole transport region on a first electrode, wherein the step of forming the hole transport region comprises a solution process step using a hole transportable composition, and the hole transportable composition comprises the heterocyclic compound.

[0026] According to another aspect, an electronic device including the above-mentioned organic light-emitting element is provided. Effects of the invention

[0027] A light-emitting device containing the above heterocyclic compound can have high efficiency and a long lifespan. Brief explanation of the drawing

[0028] FIG. 1 is a schematic diagram showing the structure of a light-emitting element according to one embodiment. FIG. 2 is a schematic diagram showing the structure of an electronic device according to one embodiment. FIG. 3 is a schematic diagram showing the structure of an electronic device according to another embodiment. Specific details for implementing the invention

[0029] The above heterocyclic compound is represented by the following chemical formula 1:

[0030] <Chemical Formula 1>

[0031]

[0032] In the above Chemical Formula 1, L 11 to L 13 and L 21 to L 23 are independently of each other, a single bond, at least one R 10a C1-C substituted or unsubstituted 20 alkylene group, at least one R 10a C2-C substituted or unsubstituted 20 alkenylene group, or at least one R 10a C2-C substituted or unsubstituted 20 It is an alkynylene group.

[0033] According to one implementation example, L 11 to L 13 and L 21 to L 23 are independently a single bond, a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, an ethylene group, a propenylene group, a butenylene group, a butadienylene group, a pentenylene group, a pentadienylene group, an ethynylene group, a propynylene group, or a butynylene group; or

[0034] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazino group, hydrazono group and C1-C 10It may be a methylene group, ethylene group, propylene group, butylene group, pentylene group, ethenylene group, propenylene group, butenylene group, butadienylene group, pentenylene group, pentadienylene group, ethylene group, propynylene group, or butynylene group substituted with at least one of the alkyl groups.

[0035] In the above chemical formula 1, a11 to a13 and a21 to a23 are independently 0, 1, 2, 3, 4 or 5.

[0036] According to one embodiment, a11 to a13 and a21 to a23 are independently 0, 1, 2 or 3.

[0037] In the above Chemical Formula 1, Z 11 To Z 13 , Z 21 To Z 23 and R1 to R9 are independently hydrogen, deuterium, azide group (-N3), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazino group, hydrazono group, at least one R 10a C1-C substituted or unsubstituted 60 alkyl group, at least one R 10a C2-C substituted or unsubstituted 60 alkenyl group, at least one R 10a C2-C substituted or unsubstituted 60 alkynyl group, at least one R 10a C1-C substituted or unsubstituted 60 Alkoxy group, at least one R 10a C3-C substituted or unsubstituted 10 Cycloalkyl group, at least one R 10a C1-C substituted or unsubstituted 10 Heterocycloalkyl group, at least one R 10a C3-C substituted or unsubstituted 10 Cycloalkenyl group, at least one R 10a C1-C substituted or unsubstituted 10Heterocycloalkenyl group, at least one R 10a C6-C substituted or unsubstituted 60 Arylgi, at least one R 10a C6-C substituted or unsubstituted 60 aryloxy group, at least one R 10a C6-C substituted or unsubstituted 60 Arylthiogi, at least one R 10a C1-C substituted or unsubstituted 60 Heteroaryl group, at least one R 10a C1-C substituted or unsubstituted 60 Heteroaryloxy group, at least one R 10a C1-C substituted or unsubstituted 60 Heteroaryltio group, at least one R 10a A monovalent non-aromatic condensed polycyclic group substituted or unsubstituted with R, at least one R 10a It is a monovalent non-aromatic heterocondensed polycyclic group substituted or unsubstituted with -Si(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) or -P(=S)(Q1)(Q2).

[0038] In the above Chemical Formula 1, Z 11 To Z 13 , Z 21 To Z 23 and at least one of R1 to R9 is -N3.

[0039] According to one embodiment, the heterocyclic compound may include 1 to 5 azide groups (-N3). For example, the heterocyclic compound may include 2 or 3 -N3 groups.

[0040] According to one embodiment, in the above Chemical Formula 1, Z 11 To Z 13 and Z 21 To Z 23 At least one of them may be -N3.

[0041] According to one embodiment, in the above Chemical Formula 1, Z 11 To Z 13 Each of these can be -N3.

[0042] According to one embodiment, Z in Chemical Formula 1 21 To Z 23 Each of these can be -N3.

[0043] In the above Chemical Formula 1, Z 11 To Z 13 In the case where all of these are -N3, -(L 21 ) a21 -Z 21 , -(L 22 ) a22 -Z 22 and -(L 23 ) a23 -Z 23 At least one of them represents hydrogen.

[0044] According to one embodiment, the heterocyclic compound may be represented by any one of the following chemical formulas 2A and 2B:

[0045] <Chemical Formula 2A>

[0046]

[0047] <Chemical Formula 2B>

[0048]

[0049] Among the above chemical formulas 2A and 2B,

[0050] L 11 to L 13 , L 21 to L 23 , Z 11 To Z 13 , Z 21 To Z 23 and the descriptions of R1 to R9 refer to those described in this specification, and

[0051] R 11 to R 13are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazino group, hydrazono group, at least one R 10a C1-C substituted or unsubstituted 60 alkyl group, at least one R 10a C2-C substituted or unsubstituted 60 alkenyl group, at least one R 10a C2-C substituted or unsubstituted 60 alkynyl group, at least one R 10a C1-C substituted or unsubstituted 60 Alkoxy group, at least one R 10a C3-C substituted or unsubstituted 10 Cycloalkyl group, at least one R 10a C1-C substituted or unsubstituted 10 Heterocycloalkyl group, at least one R 10a C3-C substituted or unsubstituted 10 Cycloalkenyl group, at least one R 10a C1-C substituted or unsubstituted 10 Heterocycloalkenyl group, at least one R 10a C6-C substituted or unsubstituted 60 Arylgi, at least one R 10a C6-C substituted or unsubstituted 60 aryloxy group, at least one R 10a C6-C substituted or unsubstituted 60 Arylthiogi, at least one R 10a C1-C substituted or unsubstituted 60 Heteroaryl group, at least one R 10a C1-C substituted or unsubstituted 60 Heteroaryloxy group, at least one R 10a C1-C substituted or unsubstituted 60 Heteroaryltio group, at least one R 10a A monovalent non-aromatic condensed polycyclic group substituted or unsubstituted with R, at least one R 10aA monovalent non-aromatic heterocondensed polycyclic group substituted or unsubstituted with -Si(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) or -P(=S)(Q1)(Q2), and

[0052] R 10a Refer to the description of as set forth in this specification.

[0053] According to one implementation example, Z 11 To Z 13 , Z 21 To Z 23 and R1 to R9 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 alkyl group or C1-C 20 Alkoxygenation;

[0054] C1-C substituted with deuterium, -F, -Cl, -Br, -I, cyano groups, phenyl groups, biphenyl groups, or any combination thereof 20 alkyl group or C1-C 20 Alkoxygenation;

[0055] Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, dibenzoflurenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentacenyl group, pyrroleyl group, thiophenyl group, furanyl group, silolyl group, imidazoleyl group, pyrazolyl group, thiazoleyl group, isothiazyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, Pyrimidinyl group, pyridazinyl group, indole group, isoindole group, indazole group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, benzisoquinolinyl group, phthalazinyl group, naphthiridinyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group, cinolinyl group, phenanthridinyl group, acrridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazole group, benzofuranyl group, benzothiophenyl group, benzocilol group, benzothiazole group, benzisothiazole group, benzoxazole group, benzisooxazole group, triazole group, tetrazole group, thiadiazole group, oxadiazole group, Triazinyl group, carbazoleyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazoleyl group, naphthobenzofuranyl group, naphthobenzothiophenyl group, naphthobenzosilolyl group, dibenzocarbazoleyl group, dinaphthofuranyl group, dinaphthiophenyl group, dinaphthosilolyl group, imidazopyridinyl group, imidazopyrimidinyl group, oxazolopyridinyl group, thiazolopyridinyl group, benzonaphthiridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazoleyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilolyl group, indenopyrrolyl group, indolopyrrolyl group, indenocarbazoleyl group or Indolocarbazol Diary;

[0056] Deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 Alkyl group, C1-C 20Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, dibenzoflurenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentacenyl group, pyrroleyl group, thiophenyl group, furanyl group, silolyl group, imidazoleyl group, pyrazolyl group, thiazoleyl group, isothiazyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, Pyrimidinyl group, pyridazinyl group, indole group, isoindole group, indazole group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, isoquinolinyl group, phthalazinyl group, naphthalidinyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group, cinolinyl group, phenanthridinyl group, acrridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazole group, benzofuranyl group, benzothiophenyl group, benzocilol group, benzothiazole group, benzisothiazole group, benzoxazole group, benzisooxazole group, triazole group, tetrazole group, thiadiazole group, oxadiazole group, triazinyl group, Carbazole yl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilol yl group, benzocarbazole yl group, naphthobenzofuranyl group, naphthobenzothiophenyl group, naphthobenzosilol yl group, dibenzocarbazole yl group, dinaphthofuranyl group, dinaphthiophenyl group, dinaphthosilol yl group, imidazopyridinyl group, imidazopyrimidinyl group, oxazolopyridinyl group, thiazolopyridinyl group, benzonaphthiridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazole yl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilol yl group, indenopyrol yl group, indolopyrol yl group, indenocarbazole yl group, indolocabazole yl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32), -C(=O)(Q 31 ), -S(=O)(Q 31 ), -S(=O)2(Q 31 ), -P(=O)(Q 31 )(Q 32 ), -P(=S)(Q 31 )(Q 32) or substituted with any combination thereof, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, dibenzoflurenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentacenyl group, pyrroleyl group, thiophenyl group, furanyl group, silolyl group, imidazoleyl group, pyrazolyl group, thiazoleyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, Pyrazinyl group, pyrimidinyl group, pyridazinyl group, indole group, isoindole group, indazole group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, isoquinolinyl group, phthalazinyl group, naphthiridinyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group, cinolinyl group, phenanthridinyl group, acrridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazole group, benzofuranyl group, benzothiophenyl group, benzocilol group, benzothiazole group, benzisothiazole group, benzoxazole group, benzisooxazole group, triazole group, tetrazole group, thiadiazole group, oxadiazole group, Triazinyl group, carbazoleyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazoleyl group, naphthobenzofuranyl group, naphthobenzothiophenyl group, naphthobenzosilolyl group, dibenzocarbazoleyl group, dinaphthofuranyl group, dinaphthiophenyl group, dinaphthosilolyl group, imidazopyridinyl group, imidazopyrimidinyl group, oxazolopyridinyl group, thiazolopyridinyl group, benzonaphthiridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazoleyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilolyl group, indenopyrrolyl group, indolopyrrolyl group, indenocarbazoleyl group or Indolocarbazole diary; or

[0057] -Si(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) or -P(=S)(Q1)(Q2).

[0058] According to one embodiment, R1 to R9 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 alkyl group or C1-C 20 Alkoxygenation;

[0059] C1-C substituted with deuterium, -F, -Cl, -Br, -I, cyano groups, phenyl groups, biphenyl groups, or any combination thereof 20 alkyl group or C1-C 20 Alkoxy group; or

[0060] It may be selected from the group represented by any one of the following chemical formulas 5-1 to 5-26 and 6-1 to 6-55:

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069] Among the above chemical formulas 5-1 to 5-26 and 6-1 to 6-55,

[0070] Y 31 and Y 32 are independently of each other, O, S, C(Z 33 )(Z 34 ), N(Z 33 ) or Si(Z33 )(Z 34 ) and,

[0071] Z 31 To Z 34 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazino group, hydrazono group, C1-C 20 Alkyl group, C2-C 20 alkenyl group, C2-C 20 alkynyl group, C1-C 20 Selected from alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, phenanthrenyl groups, anthracenyl groups, triphenylenyl groups, pyridinyl groups, pyrimidinyl groups, carbazole groups, and triazinyl groups,

[0072] e2 is 1 or 2, and

[0073] e3 is an integer selected from 1 to 3, and

[0074] e4 is an integer selected from 1 to 4, and

[0075] e5 is an integer selected from 1 to 5, and

[0076] e6 is an integer selected from 1 to 6, and

[0077] e7 is an integer selected from 1 to 7, and

[0078] e9 is an integer selected from 1 to 9, and

[0079] * is a bonding site with a neighboring atom.

[0080] According to one embodiment, R1 to R9 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 alkyl group or C1-C 20 Alkoxygenation;

[0081] C1-C substituted with deuterium, -F, -Cl, -Br, -I, cyano groups, phenyl groups, biphenyl groups, or any combination thereof 20alkyl group or C1-C 20 Alkoxygenation;

[0082] Phenyl group, biphenyl group, terphenyl group, penthalenyl group, indenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, dibenzoflurenyl group, carbazoleyl group, acridinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group or dibenzocarbazoleyl group; or

[0083] Deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 Alkyl group, C1-C 20 It may be a phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, dibenzoflurenyl group, carbazoleyl group, acridinyl group, dibenzofuraninyl group, dibenzothiophenyl group, benzocarbazoleyl group or dibenzocarbazoleyl group substituted with an alkoxy group, a phenyl group, a biphenyl group or any combination thereof.

[0084] According to one implementation example, Z 11 To Z 13 , Z 21 To Z 23 and R1 to R9 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 alkyl group or C1-C 20 Alkoxygenation;

[0085] C1-C substituted with deuterium, -F, -Cl, -Br, -I, cyano groups, phenyl groups, biphenyl groups, and any combination thereof 20 Alkyl groups and C1-C 20 Alkoxygenation;

[0086] Phenyl group, biphenyl group, terphenyl group, penthalenyl group, indenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, dibenzoflurenyl group, carbazoleyl group, acridinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group or dibenzocarbazoleyl group; or

[0087] Deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 Alkyl group, C1-C 20 It may be a phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, dibenzoflurenyl group, carbazoleyl group, acridinyl group, dibenzofuraninyl group, dibenzothiophenyl group, benzocarbazoleyl group or dibenzocarbazoleyl group substituted with an alkoxy group, a phenyl group, a biphenyl group or any combination thereof.

[0088] According to one embodiment, the heterocyclic compound may be represented by any one of the following chemical formulas 3A-1 to 3A-3, 3B-1 and 3B-2:

[0089] <Chemical Formula 3A-1>

[0090]

[0091] <Chemical Formula 3A-2>

[0092]

[0093] <Chemical Formula 3A-3>

[0094]

[0095] <Chemical Formula 3B-1>

[0096]

[0097] <Chemical Formula 3B-2>

[0098]

[0099] Among the above chemical formulas 3A-1 to 3A-3, 3B-1 and 3B-2,

[0100] k1, k2, and k3 are 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, respectively, and

[0101] g1, g2, and g3 are 4, 5, 6, 7, 8, 9, or 10, respectively, and

[0102] m1, m2, and m3 are 1, 2, 3, 4, or 5, respectively.

[0103] According to one embodiment, the heterocyclic compound represented by the above chemical formula 1 may be any one of the following compounds 1 to 7:

[0104] <Compound 1>

[0105]

[0106] <Compound 2>

[0107]

[0108] <Compound 3>

[0109]

[0110] <Compound 4>

[0111]

[0112] <Compound 5>

[0113]

[0114] <Compound 6>

[0115]

[0116] <Compound 7>

[0117] .

[0118] The above heterocyclic compound has a structure capable of thermal and photocrosslinking by including an azide group. Therefore, the above heterocyclic compound can form a film through a crosslinking reaction without using a separate crosslinking agent, and thereby can exhibit excellent hole transport characteristics and structural stability.

[0119] Accordingly, an electronic device, such as a light-emitting device, employing a heterocyclic compound represented by Chemical Formula 1 above can exhibit low driving voltage, high efficiency, and a long lifespan. In addition, when an intermediate layer of a light-emitting device is formed by a solution process using a composition containing the heterocyclic compound above, the phenomenon of degradable molecular arrangement deformation due to driving of the light-emitting device is prevented, thereby providing a light-emitting device with excellent hole mobility and lifespan characteristics.

[0120] A method for synthesizing a heterocyclic compound represented by the above chemical formula 1 can be recognized by those skilled in the art by referring to the examples described below.

[0121] [Composition]

[0122] According to another aspect of the present invention, a hole-transporting composition comprising the heterocyclic compound is provided.

[0123] According to one embodiment, the hole transportable composition may further include a solvent.

[0124] According to one embodiment, the solvent is C6-C 20 Aliphatic hydrocarbons, C5-C 20 It may include aromatic hydrocarbons, chloroform, methylene chloride, methyl benzoate, ethyl acetate, ethylene glycol, diethylene glycol, or any combination thereof.

[0125] According to one embodiment, the solvent can be represented by the following chemical formula 8:

[0126] <Chemical Formula 8>

[0127]

[0128] Among the above chemical formula 8,

[0129] X 81 is a single bond, -O-, -S-, -C(=O)-, -C(=O)O- or -C(=O)NH-, and

[0130] R 81 and R 82 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazino group, hydrazono group, Si(Q 31 )(Q 32 )(Q 33 ), C1-C 10 Alkyl group, C1-C 10 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, phenanthrenyl group, pyrenyl group, carbazoleyl group, dibenzofuraninyl group, benzonaphthofuraninyl group, dibenzothiophenyl group, benzocarbazoleyl group or dibenzocarbazoleyl group; or

[0131] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazino group, hydrazono group, Si(Q 81 )(Q 82 )(Q 83 ), methyl group, ethyl group, propyl group, isobutyl group, sec-butyl group, ter-butyl group, pentyl group, iso-amyl group, hexyl group, C1-C 10 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, phenanthrenyl group, pyrenyl group, carbazoleyl group, carbazoleyl group substituted with a phenyl group, dibenzofuranyl group, benzonaphthofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group, dibenzocarbazoleyl group or any combination thereof substituted with, C1-C 10 Alkyl group, C1-C 10Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, phenanthrenyl group, pyrenyl group, carbazoleyl group, dibenzofuranyl group, benzonaphthofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group or dibenzocarbazoleyl group; and,

[0132] b 81 are independently 1, 2, 3, 4, or 5, and

[0133] Above Q 81 to Q 83 They are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazino group, hydrazono group, C1-C 60 Alkyl group, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C6-C 60 Aryl group, C1-C 60 C6-C substituted with alkyl groups 60 Aryl group, C1-C 60 It is a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, a biphenyl group, or a terphenyl group.

[0134] According to one embodiment, the solvent is C5-C 20 It can be an aromatic hydrocarbon, for example, anisole.

[0135] According to one embodiment, the hole transportable composition comprises the heterocyclic group and the solvent, and the content of the heterocyclic group per 100 parts by weight of the hole transportable composition may be 0.01 to 50 parts by weight. For example, the content of the heterocyclic group per 100 parts by weight of the hole transportable composition may be 0.05 to 20 parts by weight, or 0.1 to 10 parts by weight, or 0.5 to 5 parts by weight. When the above content range is satisfied, the hole transportable composition may exhibit properties suitable for use in solution processes such as inkjet.

[0136] [Light-emitting element]

[0137] According to one embodiment, the apparatus comprises: a first electrode; a second electrode facing the first electrode; and an intermediate layer including a light-emitting layer interposed between the first electrode and the second electrode.

[0138] A light-emitting element is provided, comprising: the above heterocyclic compound; a polymer comprising repeating units derived from the above heterocyclic compound; or any combination thereof.

[0139] According to one embodiment, the repeating unit derived from the heterocyclic compound may be represented by any one of the following chemical formulas 1-1 to 1-4:

[0140] <Chemical Formula 1-1>

[0141]

[0142] <Chemical Formula 1-2>

[0143]

[0144] <Chemical Formula 1-3>

[0145]

[0146] <Chemical Formula 1-4>

[0147]

[0148] Among the above chemical formulas 1-1 to 1-4

[0149] L 11 to L 13 , L 21 to L 23 , R1 to R9, and R 11 to R 13 Refer to the description of as set forth in this specification.

[0150] According to one embodiment, the first electrode of the light-emitting element is an anode, and the second electrode of the light-emitting element is a cathode, and

[0151] The above intermediate layer includes a hole transport region disposed between the first electrode and the light-emitting layer, and the hole transport region may include the heterocyclic compound, the polymer, or any combination thereof.

[0152] According to one embodiment, the hole transport region may include a hole injection layer, a hole transport layer, a buffer layer, a light-emitting auxiliary layer, an electron blocking layer, or any combination thereof.

[0153] For example, the hole transport region comprises a hole injection layer, a hole transport layer, a buffer layer, a light-emitting auxiliary layer, an electron blocking layer, or any combination thereof, and

[0154] The hole injection layer, hole transport layer, buffer layer, light-emitting auxiliary layer, electron blocking layer, or any combination thereof may include the heterocyclic compound, the polymer, or any combination thereof.

[0155] According to one embodiment, the light-emitting layer of the light-emitting element comprises a host and a dopant, and the host or dopant may comprise the heterocyclic compound, the polymer, or any combination thereof.

[0156] According to one embodiment, the light-emitting element further includes an electron transport region interposed between the light-emitting layer and the second electrode, and

[0157] The above electron transport region may include at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.

[0158] According to another embodiment, the light-emitting element further comprises at least one of a first capping layer disposed outside the first electrode and a second capping layer disposed outside the second electrode, and at least one of the first capping layer and the second capping layer may contain an organometallic compound represented by Formula 1. For a more detailed description of the first capping layer and / or the second capping layer, refer to the description in this specification.

[0159] According to one embodiment, the light-emitting element is,

[0160] A first capping layer disposed on the outer side of the first electrode and comprising an organometallic compound represented by the chemical formula 1;

[0161] A second capping layer disposed on the outer side of the second electrode and comprising an organometallic compound represented by the chemical formula 1; or

[0162] The first capping layer and the second capping layer;

[0163] It may include.

[0164] In this specification, the phrase “(the intermediate layer and / or capping layer) comprises a heterocyclic compound” may be interpreted as “(the intermediate layer and / or capping layer) may comprise one heterocyclic compound belonging to the category of Formula 1 or two or more different heterocyclic compounds belonging to the category of Formula 1.”

[0165] For example, the intermediate layer and / or capping layer may include only Compound 1 as the heterocyclic compound. In this case, Compound 1 may be present in the light-emitting layer of the light-emitting device. Alternatively, the intermediate layer may include Compound 1 and Compound 2 as the heterocyclic compound. In this case, Compound 1 and Compound 2 may be present in the same layer (for example, Compound 1 and Compound 2 may both be present in the hole transport region) or in different layers (for example, Compound 1 may be present in the hole transport region and Compound 2 may be present in the light-emitting layer).

[0166] In this specification, "intermediate layer" is a term referring to a single and / or multiple layers disposed between the first electrode and the second electrode of the light-emitting element.

[0167] According to another aspect, an electronic device including a light-emitting element as described above is provided. The electronic device may further include a thin-film transistor. For example, the electronic device may further include a thin-film transistor including a source electrode and a drain electrode, and the first electrode of the light-emitting element may be electrically connected to the source electrode or the drain electrode. Meanwhile, the electronic device may further include a color filter, a color conversion layer, a touchscreen layer, a polarizing layer, or any combination thereof. A more detailed description of the electronic device is provided as described in this specification.

[0168] [Explanation of Fig. 1]

[0169] FIG. 1 schematically illustrates a cross-sectional view of a light-emitting element (10) according to one embodiment of the present invention. The light-emitting element (10) includes a first electrode (110), an intermediate layer (130), and a second electrode (150).

[0170] Hereinafter, the structure and manufacturing method of a light-emitting element (10) according to one embodiment of the present invention are described as follows with reference to FIG. 1.

[0171] [First electrode (110)]

[0172] A substrate may be additionally disposed on the lower part of the first electrode (110) of FIG. 1 or on the upper part of the second electrode (150). As the substrate, a glass substrate or a plastic substrate may be used. Alternatively, the substrate may be a flexible substrate and may include a plastic with excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphtalate, polyarylate (PAR), polyetherimide, or any combination thereof.

[0173] The first electrode (110) can be formed, for example, by providing a material for the first electrode on the substrate using a deposition method or a sputtering method. When the first electrode (110) is an anode, a material with a high work function that facilitates hole injection can be used as the material for the first electrode.

[0174] The first electrode (110) may be a reflective electrode, a semi-transparent electrode, or a transparent electrode. To form the first electrode (110) which is a transparent electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof may be used as the material for the first electrode. Alternatively, to form the first electrode (110) which is a semi-transparent electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof may be used as the material for the first electrode.

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

[0176] [Middle layer (130)]

[0177] An intermediate layer (130) is disposed on the upper portion of the first electrode (110). The intermediate layer (130) includes a light-emitting layer.

[0178] The above intermediate layer (130) may further include a hole transport region disposed between the first electrode (110) and the light-emitting layer and an electron transport region disposed between the light-emitting layer and the second electrode (150).

[0179] The above intermediate layer (130) may further include, in addition to various organic materials, metal-containing compounds such as organometallic compounds, inorganic materials such as quantum dots, etc.

[0180] Meanwhile, the intermediate layer (130) may include i) two or more emitting units sequentially stacked between the first electrode (110) and the second electrode (150), and ii) a charge generation layer disposed between the two emitting units. When the intermediate layer (130) includes the emitting units and charge generation layer as described above, the emitting element (10) may be a tandem emitting element.

[0181] [Middle layer (130) with a fixed transport area]

[0182] The hole transport region may have i) a monolayer structure consisting of a single layer made of a single material, ii) a monolayer structure consisting of a single layer containing multiple different materials, or iii) a multilayer structure including multiple layers containing multiple different materials.

[0183] The hole transport region may include a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting auxiliary layer, an electron blocking layer (EBL), or any combination thereof.

[0184] For example, the hole transport region may have a multilayer structure of a hole injection layer / hole transport layer, a hole injection layer / hole transport layer / light-emitting auxiliary layer, a hole injection layer / light-emitting auxiliary layer, a hole transport layer / light-emitting auxiliary layer, or a hole injection layer / hole transport layer / electron blocking layer stacked sequentially from the first electrode (110).

[0185] The hole transport region may comprise the heterocyclic compound; a polymer comprising repeating units derived from the heterocyclic compound; or any combination thereof.

[0186] The hole transport region may further include a compound represented by the following chemical formula 201, a compound represented by the following chemical formula 202, or any combination thereof:

[0187] <Chemical Formula 201>

[0188]

[0189] <Chemical Formula 202>

[0190]

[0191] Among the above chemical formulas 201 and 202,

[0192] L 201 to L 204 are independent of each other, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and

[0193] L 205 은, *-O-*', *-S-*', *-N(Q 201 )-*', at least one R 10a C1-C substituted or unsubstituted 20 alkylene group, at least one R 10a C2-C substituted or unsubstituted 20 alkenylene group, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and

[0194] xa1 to xa4 are independently one of integers 0 to 5, and

[0195] xa5 is one of integers from 1 to 10, and

[0196] R201 to R 204 and Q 201 are independent of each other, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and

[0197] R 201 and R 202 is optionally a single bond, at least one R 10a A C1-C5 alkylene group substituted or unsubstituted with or at least one R 10a Connected to each other through C2-C5 alkenylene groups substituted or unsubstituted, at least one R 10a C8-C substituted or unsubstituted 60 It can form polycyclic groups (e.g., carbazole groups, etc.) (e.g., refer to the following compound HT16, etc.),

[0198] R 203 and R 204 is optionally a single bond, at least one R 10a A C1-C5 alkylene group substituted or unsubstituted with or at least one R 10a Connected to each other through C2-C5 alkenylene groups substituted or unsubstituted, at least one R 10a C8-C substituted or unsubstituted 60 It can form polycyclic groups, and

[0199] na1 can be one of integers from 1 to 4.

[0200] For example, each of the above chemical formulas 201 and 202 may include at least one of the group represented by the following chemical formulas CY201 to CY217:

[0201]

[0202] Among the above chemical formulas CY201 to CY217, R 10b and R 10c Descriptions of each of R in this specification 10a Refer to the explanation for, and ring CY 201 Inner ring CY 204 are independently of each other, C3-C 20 Carbocyclic group or C1-C 20 It is a heterocyclic group, and at least one hydrogen of the chemical formulas CY201 to CY217 is R as described in this specification. 10a It can be substituted or unsubstituted.

[0203] According to one embodiment, among the chemical formulas CY201 to CY217, the ring CY 201 Inner ring CY 204 It can be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group independently of each other.

[0204] According to another embodiment, each of the above formulas 201 and 202 may include at least one of the group represented by the formulas CY201 to CY203.

[0205] According to another embodiment, the formula 201 may each include at least one of the group represented by formulas CY201 to CY203 and at least one of the group represented by formulas CY204 to CY217.

[0206] According to another embodiment, xa1 in the above chemical formula 201 is 1, and R 201 is a group represented by one of the above chemical formulas CY201 to CY203, xa2 is 0, and R 202 may be a group represented by one of the above chemical formulas CY204 to CY207.

[0207] According to another embodiment, each of the above formulas 201 and 202 may not include the group represented by the above formulas CY201 to CY203.

[0208] According to another embodiment, each of the above formulas 201 and 202 may not include the group represented by formulas CY201 to CY203 and may include at least one of the group represented by formulas CY204 to CY217.

[0209] As another example, each of the above chemical formulas 201 and 202 may not include the group represented by the above chemical formulas CY201 to CY217.

[0210] For example, the hole transport region is one of the following compounds HT1 to HT44, m-MTDATA, TDATA, 2-TNATA, NPB(NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), PANI / DBSA (Polyaniline / Dodecylbenzenesulfonic acid), PEDOT / PSS (Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate)), PANI / CSA (Polyaniline / Camphor sulfonic acid It may further include (polyaniline / campersulfonic acid)), PANI / PSS (polyaniline / poly(4-styrenesulfonate)), or any combination thereof:

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220] The thickness of the hole transport region may be about 50 Å to about 10,000 Å, for example, about 100 Å to about 4,000 Å. If the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be about 100 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, and the thickness of the hole transport layer may be about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the ranges described above, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

[0221] The light-emitting auxiliary layer is a layer that increases light emission efficiency by compensating for the optical resonance distance according to the wavelength of light emitted from the light-emitting layer, and the electron blocking layer is a layer that prevents electron injection from the electron transport region. The light-emitting auxiliary layer and the electron blocking layer may include materials as described above.

[0222] [p-dopant]

[0223] In addition to the material described above, the hole transport region may further include a charge-generating material to improve conductivity. The charge-generating material may be uniformly or non-uniformly dispersed within the hole transport region (e.g., in the form of a single layer consisting of the charge-generating material).

[0224] The above charge-generating material may be, for example, a p-dopant.

[0225] For example, the LUMO energy level of the above p-dopant may be -3.5 eV or less.

[0226] According to one embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, an element EL1 and an element EL2-containing compound, or any combination thereof.

[0227] Examples of the above quinone derivatives may include TCNQ, F4-TCNQ, etc.

[0228] Examples of the above cyano group-containing compounds may include HAT-CN, compounds represented by the following chemical formula 221, etc.

[0229]

[0230] <Chemical Formula 221>

[0231]

[0232] Of the above chemical formula 221,

[0233] R 221 to R 223 are independent of each other, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and

[0234] The above R 221 to R 223At least one of which is independently substituted with a cyano group; -F; -Cl; -Br; -I; a cyano group, -F, -Cl, -Br, -I, or any combination thereof C1-C 20 C3-C substituted with an alkyl group; or any combination thereof. 60 Carbocyclic group or C1-C 60 It can be a heterocyclic group.

[0235] Among the above-mentioned compounds containing elements EL1 and EL2, element EL1 may be a metal, a metalloid, or a combination thereof, and element EL2 may be a nonmetal, a metalloid, or a combination thereof.

[0236] Examples of the above metals are alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); Transition metals (e.g., zinc (Zn), indium (In), tin (Sn), etc.); lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodium (Pr), neodymium (Nd), promerium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), ruthenium (Lu), etc.); etc. may be included.

[0237] Examples of the above metalloids may include silicon (Si), antimony (Sb), tellurium (Te), etc.

[0238] Examples of the above nonmetals may include oxygen (O), halogens (e.g., F, Cl, Br, I, etc.).

[0239] For example, the above-mentioned element EL1 and element EL2-containing compounds may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metal tellurides, or any combination thereof.

[0240] Examples of the above metal oxides may include tungsten oxide (e.g., WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxide (e.g., VO, V2O3, VO2, V2O5, etc.), molybdenum oxide (MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), rhenium oxide (e.g., ReO3, etc.).

[0241] Examples of the above metal halides may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, lanthanide metal halides, etc.

[0242] Examples of the above alkali metal halides may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, etc.

[0243] Examples of the above alkaline earth metal halides may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, BaI2, etc.

[0244] Examples of the above transition metal halides include titanium halides (e.g., TiF4, TiCl4, TiBr4, TiI4, etc.), zirconium halides (e.g., ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), hafnium halides (e.g., HfF4, HfCl4, HfBr4, HfI4, etc.), vanadium halides (e.g., VF3, VCl3, VBr3, VI3, etc.), niobium halides (e.g., NbF3, NbCl3, NbBr3, NbI3, etc.), tantalum halides (e.g., TaF3, TaCl3, TaBr3, TaI3, etc.), chromium halides (e.g., CrF3, CrCl3, CrBr3, CrI3, etc.), molybdenum halides (e.g., MoF3, MoCl3, MoBr3, MoI3, etc.), and tungsten. Halides (e.g., WF3, WCl3, WBr3, WI3, etc.), manganese halides (e.g., MnF2, MnCl2, MnBr2, MnI2, etc.), technetium halides (e.g., TcF2, TcCl2, TcBr2, TcI2, etc.), rhenium halides (e.g., ReF2, ReCl2, ReBr2, ReI2, etc.), iron halides (e.g., FeF2, FeCl2, FeBr2, FeI2, etc.), ruthenium halides (e.g., RuF2, RuCl2, RuBr2, RuI2, etc.), osmium halides (e.g., OsF2, OsCl2, OsBr2, OsI2, etc.), cobalt halides (e.g., CoF2, CoCl2, CoBr2, CoI2, etc.), rhodium halides (e.g., RhF2, RhCl2, RhBr2, RhI2, etc.), iridium halides (e.g., IrF2, IrCl2, IrBr2, IrI2, etc.), nickel halides (e.g., NiF2, NiCl2, NiBr2, NiI2, etc.), palladium halides (e.g., PdF2, PdCl2, PdBr2, PdI2, etc.), platinum halides (e.g., PtF2, PtCl2, PtBr2, PtI2, etc.), copper halides (e.g., CuF, CuCl, CuBr, CuI, etc.),It may include silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.), gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.), etc.

[0245] Examples of the above-mentioned transition metal halides may include zinc halides (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halides (e.g., InI3, etc.), tin halides (e.g., SnI2, etc.), etc.

[0246] Examples of the above lanthanide metal halides may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3SmCl3, YbBr, YbBr2, YbBr3SmBr3, YbI, YbI2, YbI3, SmI3, etc.

[0247] Examples of the metalloid halides mentioned above may include antimony halides (e.g., SbCl5, etc.).

[0248] Examples of the above metal tellurides include alkali metal tellurides (e.g., Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g., TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), post-transition metal tellurides (e.g., ZnTe, etc.), and lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, It may include TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.

[0249] [Emitting layer in the middle layer (130)]

[0250] When the light-emitting element (10) is a full-color light-emitting element, the light-emitting layer may be patterned into a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer for each individual subpixel. Alternatively, the light-emitting layer may have a structure in which two or more layers among the red light-emitting layer, the green light-emitting layer, and the blue light-emitting layer are stacked in contact or spaced apart, or may have a structure in which two or more materials among the red light-emitting material, the green light-emitting material, and the blue light-emitting material are mixed without layer separation, thereby emitting white light.

[0251] The light-emitting layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.

[0252] According to one embodiment, the dopant may include an organometallic compound represented by Formula 1 as described in this specification.

[0253] The content of the dopant in the above-mentioned light-emitting layer may be about 0.01 to about 15 parts by weight per 100 parts by weight of the host.

[0254] Alternatively, the light-emitting layer may include quantum dots.

[0255] Meanwhile, the light-emitting layer may include a delayed fluorescent material. The delayed fluorescent material may act as a host or dopant in the light-emitting layer.

[0256] The thickness of the light-emitting layer may be about 100 Å to about 1000 Å, for example, about 200 Å to about 600 Å. When the thickness of the light-emitting layer satisfies the range described above, excellent light-emitting characteristics can be exhibited without a substantial increase in driving voltage.

[0257] [Host]

[0258] The host among the above-mentioned light-emitting layers may include any host.

[0259] Alternatively, the host may include a compound represented by the following chemical formula 301.

[0260] <Chemical Formula 301>

[0261] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21

[0262] Among the above chemical formula 301,

[0263] Ar 301 and L 301 are independent of each other, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and

[0264] xb11 is 1, 2, or 3, and

[0265] xb1 is one of integers from 0 to 5, and

[0266] R 301 Silver, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, at least one R 10a C1-C substituted or unsubstituted 60 alkyl group, at least one R 10a C2-C substituted or unsubstituted 60 alkenyl group, at least one R 10a C2-C substituted or unsubstituted 60 alkynyl group, at least one R 10a C1-C substituted or unsubstituted 60 Alkoxy group, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group, at least one R 10a C1-C substituted or unsubstituted 60 Heterocyclic group, -Si(Q 301 )(Q 302)(Q 303 ), -N(Q 301 )(Q 302 ), -B(Q 301 )(Q 302 ), -C(=O)(Q 301 ), -S(=O)2(Q 301 ), or -P(=O)(Q 301 )(Q 302 ) and,

[0267] xb21 is one of integers from 1 to 5, and

[0268] Q 301 to Q 303 For a description of each, refer to the description of Q1 in this specification.

[0269] For example, if xb11 in the above chemical formula 301 is 2 or more, then 2 or more Ar 301 They can be connected to each other through a single bond.

[0270] As another example, the host may include a compound represented by the following chemical formula 301-1, a compound represented by the following chemical formula 301-2, or any combination thereof:

[0271] <Chemical Formula 301-1>

[0272]

[0273] <Chemical Formula 301-2>

[0274]

[0275] Among the above chemical formulas 301-1 to 301-2,

[0276] Ring A 301 inner ring A 304 are independent of each other, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and

[0277] X 301is O, S, N-[(L 304 ) xb4 -R 304 ], C(R 304 )(R 305 ), or Si(R 304 )(R 305 ) and,

[0278] xb22 and xb23 are independently 0, 1, or 2, and

[0279] L 301 , xb1 and R 301 For descriptions thereof, refer to those described in this specification, and

[0280] L 302 to L 304 The descriptions regarding are independent of each other, the above L 301 Refer to the explanation for,

[0281] The descriptions for xb2 to xb4 are independent of each other, and refer to the description for xb1 above, and

[0282] R 302 to R 305 and R 311 to R 314 The explanation for each of the above R 301 Refer to the explanation for.

[0283] As another example, the host may include an alkaline earth metal complex. For example, the host may include a Be complex (e.g., compound H55 below), an Mg complex, a Zn complex, or any combination thereof.

[0284] As another example, the host may comprise one of the following compounds H1 to H124, ADN (9,10-Di(2-naphthyl)anthracene), MADN (2-Methyl-9,10-bis(naphthalen-2-yl)anthracene), TBADN (9,10-di-(2-naphthyl)-2-t-butyl-anthracene), CBP (4,4′-bis(N-carbazolyl)-1,1′-biphenyl), mCP (1,3-di-9-carbazolylbenzene), TCP (1,3,5-tri(carbazol-9-yl)benzene), mCBP (3,3-Di(9H-carbazol-9-yl)biphenyl), or any combination thereof:

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299] Alternatively, the host may include a silicon-containing compound (e.g., BCPDS used in the following examples), a phosphine oxide-containing compound (e.g., POPCPA used in the following examples), or any combination thereof.

[0300] The above host may be modified in various ways, such as by including only one type of compound or two or more different types of compounds (for example, the host of the following example consists of BCPDS and POPCPA).

[0301] [Phosphorescent Dopant]

[0302] The above phosphorescent dopant may include at least one transition metal as a central metal.

[0303] The phosphorescent dopant may include a monodenate ligand, a two-bed ligand, a three-bed ligand, a four-bed ligand, a five-bed ligand, a six-bed ligand, or any combination thereof.

[0304] The above phosphorescent dopant may be electrically neutral.

[0305] For example, the phosphorescent dopant may include an organometallic compound represented by the following chemical formula 401:

[0306] <Chemical Formula 401>

[0307] M(L 401 ) xc1 (L 402 ) xc2

[0308] <Chemical Formula 402>

[0309]

[0310] Among the above chemical formulas 401 and 402,

[0311] M is a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)), and

[0312] L 401 is a ligand represented by the above chemical formula 402, xc1 is 1, 2, or 3, and if xc1 is 2 or more, 2 or more L 401 They are identical or different from each other,

[0313] L 402 is an organic ligand, xc2 is 0, 1, 2, 3, or 4, and if xc2 is 2 or more, 2 or more L 402 are identical or different from each other,

[0314] X 401 and X 402 are independently nitrogen or carbon, and

[0315] Ring A 401 and ring A 402 are independently of each other, C3-C 60 Carbocyclic group or C1-C 60 It is a heterocyclic group, and

[0316] T 401 is a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*', *-C(Q 411 )(Q 412 )-*', *-C(Q 411 )=C(Q 412 )-*', *-C(Q 411 )=*' or *=C(Q 411 )=*' and,

[0317] X 403 and X 404 are independently of each other, chemical bonds (e.g., covalent bonds or coordinate bonds), O, S, N(Q 413 ), B(Q 413 ), P(Q 413 ), C(Q413 )(Q 414 ) or Si(Q 413 )(Q 414 ) and,

[0318] Above Q 411 to Q 414 For descriptions regarding each, refer to the description of Q1 in this specification, and

[0319] R 401 and R 402 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, at least one R 10a C1-C substituted or unsubstituted 20 alkyl group, at least one R 10a C1-C substituted or unsubstituted 20 Alkoxy group, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group, at least one R 10a C1-C substituted or unsubstituted 60 Heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 ), -N(Q 401 )(Q 402 ), -B(Q 401 )(Q 402 ), -C(=O)(Q 401 ), -S(=O)2(Q 401 ) or -P(=O)(Q 401 )(Q 402 ) and,

[0320] Above Q 401 to Q 403 For descriptions regarding each, refer to the description of Q1 in this specification, and

[0321] xc11 and xc12 are independently one of integers from 0 to 10, and

[0322] In the above chemical formula 402, * and *' are each binding sites with M in the above chemical formula 401.

[0323] For example, i) X in the above chemical formula 402 401 is nitrogen, and X 402 is carbon, or ii) X 401 and X 402 All of it can be nitrogen.

[0324] As another example, if xc1 in the above chemical formula 402 is 2 or more, then 2 or more L 401 Two of the rings A 401 is optionally, the connector T 402 Connected to each other through, or 2 rings A 402 is optionally, the connector T 403 They can be connected to each other through (see compounds PD1 to PD4 and PD7 below). The above T 402 and T 403 The descriptions for each of T in this specification 401 Refer to the explanation for.

[0325] L in the above chemical formula 401 402 can be any organic ligand. For example, the above L 402 It may include a halogen group, a diketone group (e.g., acetylacetonate group), a carboxylic acid group (e.g., picolinate group), -C (=O), an isonitrile group, a -CN group, a phosphorus group (e.g., phosphine group, phosphite group, etc.), or any combination thereof.

[0326] The above phosphorescent dopant may include, for example, one of the following compounds PD1 to PD25, or any combination thereof:

[0327]

[0328]

[0329]

[0330] [Delayed Fluorescence]

[0331] The above-mentioned light-emitting layer may include a delayed fluorescent material.

[0332] In this specification, the delayed fluorescent material may be selected from any compound capable of emitting delayed fluorescence by a delayed fluorescence emission mechanism.

[0333] The delay fluorescent material included in the above-mentioned light-emitting layer can act as a host or a dopant depending on the type of other material included in the above-mentioned light-emitting layer.

[0334] According to one embodiment, the difference between the triplet energy level (eV) of the delay fluorescent material and the singlet energy level (eV) of the delay fluorescent material may be 0 eV or more and 0.5 eV or less. By satisfying the range described above, the reverse energy transfer (up-conversion) from the triplet state to the singlet state of the delay fluorescent material is effectively achieved, thereby improving the luminous efficiency of the light-emitting device (10).

[0335] For example, the above-mentioned delay fluorescent material comprises: i) at least one electron donor (e.g., a π-electron-excess C3-C such as a carbazole group). 60 cyclic group (π electron-rich C3-C 60 cyclic group) etc.) and at least one electron acceptor (e.g., sulfoxide group, cyano group, π electron-deficient nitrogenous C1-C 60 cyclic group (π electron-deficient nitrogen-containing C1-C 60 ii) a substance containing a cyclic group, etc., and ii) a C8-C containing two or more cyclic groups condensed while sharing boron (B). 60 It may include materials including polycyclic groups.

[0336] Examples of the above-mentioned delayed fluorescent materials may include at least one of the following compounds DF1 to DF9:

[0337]

[0338]

[0339] [Quantum Dot]

[0340] The above-mentioned light-emitting layer may include quantum dots.

[0341] In this specification, a quantum dot refers to a crystal of a semiconductor compound and may include any material capable of emitting light of various emission wavelengths depending on the size of the crystal.

[0342] The diameter of the above quantum dots may be, for example, about 1 nm to 10 nm.

[0343] The above quantum dots can be synthesized by a wet chemical process, an organometallic chemical vapor deposition process, a molecular beam epitaxy process, or a similar process.

[0344] The above wet chemical process is a method of growing quantum dot particle crystals after mixing an organic solvent and a precursor material. When the crystals grow, the organic solvent naturally acts as a dispersant coordinated to the surface of the quantum dot crystals and controls the growth of the crystals. Therefore, the growth of quantum dot particles can be controlled through a process that is easier and lower cost than vapor deposition methods such as Metal Organic Chemical Vapor Deposition (MOCVD) or Molecular Beam Epitaxy (MBE).

[0345] The above quantum dot may include a group III-VI semiconductor compound; a group II-VI semiconductor compound; a group III-V semiconductor compound; a group III-VI semiconductor compound; a group I-III-VI semiconductor compound; a group IV-VI semiconductor compound; a group IV element or compound; or any combination thereof.

[0346] Examples of the above-mentioned group III-VI semiconductor compounds may include binary compounds such as In2S3; ternary compounds such as AgInS, AgInS2, CuInS, CuInS2, etc.; or any combination thereof.

[0347] Examples of the above-mentioned group II-VI semiconductor compounds include binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, etc.; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, etc.; It may include four-element compounds such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, etc.; or any combination thereof.

[0348] Examples of the above III-V semiconductor compounds may include: binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, etc.; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb, GaAlNP, etc.; quaternary compounds such as GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, etc.; or any combination thereof. Meanwhile, the above III-V semiconductor compounds may further include a Group II element. Examples of III-V semiconductor compounds containing additional group II elements may include InZnP, InGaZnP, InAlZnP, etc.

[0349] Examples of the above-mentioned group III-VI semiconductor compounds include binary compounds such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2Se3, InTe, etc.; InGaS 3 It may include ternary compounds such as InGaSe3, etc.; or any combination thereof.

[0350] Examples of the above-mentioned group I-III-VI semiconductor compounds may include ternary compounds such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, AgAlO2, etc.; or any combination thereof.

[0351] Examples of the above-mentioned group IV-VI semiconductor compounds may include binary compounds such as SnS, SnSe, SnTe, PbS, PbSe, PbTe, etc.; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, etc.; quaternary compounds such as SnPbSSe, SnPbSeTe, SnPbSTe, etc.; or any combination thereof.

[0352] The above Group IV elements or compounds may include single-element compounds such as Si, Ge, etc.; dual-element compounds such as SiC, SiGe, etc.; or any combination thereof.

[0353] Each element included in the multi-element compounds, such as the above-mentioned binary compounds, ternary compounds, and quaternary compounds, may exist within the particle at a uniform or non-uniform concentration.

[0354] Meanwhile, the above quantum dot may have a single structure in which the concentration of each element contained in the quantum dot is uniform, or a core-shell dual structure. For example, the material contained in the core and the material contained in the shell may be different from each other.

[0355] The shell of the quantum dot can serve as a protective layer to maintain semiconductor properties by preventing chemical degradation of the core, and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell may be a single layer or a multilayer. The interface between the core and the shell may have a concentration gradient in which the concentration of elements present in the shell decreases toward the center.

[0356] Examples of the shell of the above quantum dot include oxides of metals or nonmetals, semiconductor compounds, or combinations thereof. Examples of the above metal or nonmetal oxides may include binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, NiO, etc.; ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, CoMn2O4, etc.; or any combination thereof. Examples of the above semiconductor compounds may include group III-VI semiconductor compounds; group II-VI semiconductor compounds; group III-V semiconductor compounds; group III-VI semiconductor compounds; group I-III-VI semiconductor compounds; group IV-VI semiconductor compounds; or any combination thereof, as described in this specification. For example, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.

[0357] Quantum dots can have a full width of half maximum (FWHM) of the emission wavelength spectrum of about 45 nm or less, specifically about 40 nm or less, and more specifically about 30 nm or less, and color purity or color reproducibility can be improved in this range. In addition, since the light emitted through these quantum dots is emitted in all directions, the wide viewing angle can be improved.

[0358] In addition, the shape of the quantum dots can specifically be spherical, pyramidal, multi-arm, or cubic nanoparticles, nanotubes, nanowires, nanofibers, nanoplate-like particles, etc.

[0359] By controlling the size of the quantum dots, the energy band gap can be controlled, allowing light of various wavelengths to be obtained from the quantum dot light-emitting layer. Therefore, by using quantum dots of different sizes, a light-emitting device that emits light of various wavelengths can be realized. Specifically, the size of the quantum dots can be selected to emit red, green, and / or blue light. Additionally, the size of the quantum dots can be configured to emit white light by combining light of various colors.

[0360] [Electronic transport region in the middle layer (130)]

[0361] The electron transport region may have i) a single-layer structure consisting of a single layer made of a single material, ii) a single-layer structure consisting of a plurality of different materials, or iii) a multilayer structure including a plurality of layers containing a plurality of different materials.

[0362] The above electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer (ETL), an electron injection layer, or any combination thereof.

[0363] For example, the electron transport region may have a structure such as an electron transport layer / electron injection layer, a hole blocking layer / electron transport layer / electron injection layer, an electron control layer / electron transport layer / electron injection layer, or a buffer layer / electron transport layer / electron injection layer stacked sequentially from the light-emitting layer.

[0364] The electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer among the electron transport regions) comprises at least one π electron-deficient nitrogen-containing C1-C 60 cyclic group (π electron-deficient nitrogen-containing C1-C 60 It may include metal-free compounds containing a cyclic group.

[0365] For example, the electron transport region may include a compound represented by the following chemical formula 601.

[0366] <Chemical Formula 601>

[0367] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21

[0368] Among the above chemical formula 601,

[0369] Ar 601 , and L 601 are independent of each other, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and

[0370] xe11 is 1, 2, or 3, and

[0371] xe1 is 0, 1, 2, 3, 4, or 5, and

[0372] R 601 is, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group, at least one R 10a C1-C substituted or unsubstituted 60 Heterocyclic group, -Si(Q 601 )(Q 602 )(Q 603 ), -C(=O)(Q 601 ), -S(=O)2(Q 601 ), or -P(=O)(Q 601 )(Q 602 ) and,

[0373] Above Q 601 to Q 603 For descriptions regarding each, refer to the description of Q1 in this specification, and

[0374] xe21 is 1, 2, 3, 4, or 5, and

[0375] The above Ar 601 , L 601 and R 601 At least one of them is independent of each other, at least one R 10a π electron-deficient nitrogenous C1-C substituted or unsubstituted 60 It could be a click group.

[0376] For example, if xe11 in the above chemical formula 601 is 2 or more, then 2 or more Ar 601 They can be connected to each other through a single bond.

[0377] As another example, Ar in the above chemical formula 601 601 It may be a substituted or unsubstituted anthracene group.

[0378] As another example, the electron transport region may include a compound represented by the following chemical formula 601-1:

[0379] <Chemical Formula 601-1>

[0380]

[0381] In the above chemical formula 601-1,

[0382] X 614 is N or C(R 614 ) and, X 615 is N or C(R 615 ) and, X 616 is N or C(R 616 ) and, X 614 To X 616 At least one of them is N, and

[0383] L 611 to L 613 The explanation for each of the above L 601 Refer to the explanation for,

[0384] For descriptions of xe611 to xe613, refer to the description of xe1 above, and

[0385] R 611to R 613 The explanation for each of the above R 601 Refer to the explanation for,

[0386] R 614 to R 616 They are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl group, C1-C 20 Alkoxy group, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group, or at least one R 10a C1-C substituted or unsubstituted 60 It can be a heterocyclic group.

[0387] For example, xe1 and xe611 to xe613 in the above chemical formulas 601 and 601-1 may be 0, 1, or 2 independently of each other.

[0388] The electron transport region is one of the following compounds ET1 to ET45, BCP (2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline) , It may include Bphen(4,7-Diphenyl-1,10-phenanthroline), Alq3, BAlq, TAZ, NTAZ, TSPO1(diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide), or any combination thereof:

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396] The thickness of the electron transport region may be about 160 Å to about 5000 Å, for example, about 100 Å to about 4000 Å. If the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may be independently about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å, and the thickness of the electron transport layer may be about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and / or the electron transport layer satisfies the ranges described above, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage.

[0397] The above electron transport region (e.g., the electron transport layer among the electron transport regions) may further include a metal-containing material in addition to the material described above.

[0398] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ions of the alkali metal complex may be Li ions, Na ions, K ions, Rb ions, or Cs ions, and the metal ions of the alkaline earth metal complex may be Be ions, Mg ions, Ca ions, Sr ions, or Ba ions. The ligands coordinated to the metal ions of the alkali metal complex and the alkaline earth metal complex may independently include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

[0399] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, the following compounds ET-D1 (LiQ) or ET-D2:

[0400]

[0401] The above electron transport region may include an electron injection layer that facilitates electron injection from the second electrode (150). The electron injection layer may be in direct contact with the second electrode (150).

[0402] The electron injection layer may have i) a single-layer structure consisting of a single layer made of a single material, ii) a single-layer structure consisting of a plurality of different materials, or iii) a multilayer structure having a plurality of layers containing a plurality of different materials.

[0403] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0404] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.

[0405] The alkali metal-containing compound, alkaline earth metal-containing compound and the rare earth metal-containing compound may include oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), tellurides, or any combination thereof of the alkali metal, alkaline earth metal, and rare earth metal, respectively.

[0406] The above alkali metal-containing compound may include alkali metal oxides such as Li2O, Cs2O, K2O, etc., alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, etc., or any combination thereof. The above alkaline earth metal-containing compound may include BaO, SrO, CaO, Ba x Sr 1-x O(x is 0 <x<1를 만족하는 실수임), Ba x Ca 1-x O(x is 0 <x<1를 만족하는 실수임) 등과 같은 알칼리 토금속 화합물을 포함할 수 있다. 상기 희토류 금속-함유 화합물은, YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, 또는 이의 임의의 조함을 포함할 수 있다. 또는, 상기 희토류 금속-함유 화합물은, 란타나이드 금속 텔루라이드를 포함할 수 있다. 상기 란타나이드 금속 텔루라이드의 예는, LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, Lu2Te3등을 포함할 수 있다.

[0407] The above alkali metal complex, alkaline earth metal complex, and rare earth metal complex may comprise i) one of the ions of the alkali metal, alkaline earth metal, and rare earth metal as described above, and ii) a ligand bound to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

[0408] The electron injection layer described above may consist only of alkali metals, alkaline earth metals, rare earth metals, alkali metal-containing compounds, alkaline earth metal-containing compounds, rare earth metal-containing compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof, or may further include organic materials (e.g., compounds represented by the chemical formula 601).

[0409] According to one embodiment, the electron injection layer may be composed of i) an alkali metal-containing compound (e.g., an alkali metal halide), or ii) a) an alkali metal-containing compound (e.g., an alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI:Yb co-deposited layer, an RbI:Yb co-deposited layer, etc.

[0410] If the electron injection layer further comprises an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkaline earth metal-containing compound, rare earth metal-containing compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix containing the organic material.

[0411] The thickness of the electron injection layer may be about 1 Å to about 100 Å or about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0412] [Second electrode (150)]

[0413] A second electrode (150) is disposed on the upper portion of the intermediate layer (130) as described above. The second electrode (150) may be a cathode, which is an electron injection electrode. In this case, a metal, alloy, electrically conductive compound, or any combination thereof having a low work function may be used as the material for the second electrode (150).

[0414] The second electrode (150) may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode (150) may be a transmissive electrode, a semitransmissive electrode, or a reflective electrode.

[0415] The second electrode (150) may have a single-layer structure or a multi-layer structure having multiple layers.

[0416] [Capping layer]

[0417] A first capping layer may be disposed on the outer side of the first electrode (110), and / or a second capping layer may be disposed on the outer side of the second electrode (150). Specifically, the light-emitting element (10) may have a structure in which the first capping layer, the first electrode (110), the intermediate layer (130), and the second electrode (150) are stacked in order, a structure in which the first electrode (110), the intermediate layer (130), the second electrode (150), and the second capping layer are stacked in order, or a structure in which the first capping layer, the first electrode (110), the intermediate layer (130), the second electrode (150), and the second capping layer are stacked in order.

[0418] Light generated in the light-emitting layer of the intermediate layer (130) of the light-emitting element (10) can be emitted to the outside through the first electrode (110), which is a semi-transparent electrode or a transparent electrode, and the first capping layer, and light generated in the light-emitting layer of the intermediate layer (130) of the light-emitting element (10) can be emitted to the outside through the second electrode (150), which is a semi-transparent electrode or a transparent electrode, and the second capping layer.

[0419] The first capping layer and the second capping layer can serve to improve external light emission efficiency based on the principle of constructive interference. As a result, the light extraction efficiency of the light-emitting element (10) is increased, and the light emission efficiency of the light-emitting element (10) can be improved.

[0420] Each of the above first capping layer and second capping layer may include a material having a refractive index of 1.6 or higher (at 589 nm).

[0421] The first capping layer and the second capping layer may independently be an organic capping layer containing organic material, an inorganic capping layer containing inorganic material, or a composite capping layer containing organic and inorganic material.

[0422] At least one of the first capping layer and the second capping layer may independently comprise a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, porphine derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may optionally be substituted with a substituent comprising O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof.

[0423] According to one embodiment, at least one of the first capping layer and the second capping layer may independently comprise an amine group-containing compound.

[0424] For example, at least one of the first capping layer and the second capping layer may independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.

[0425] According to another embodiment, at least one of the first capping layer and the second capping layer may independently comprise one of the compounds HT28 to HT33, one of the following compounds CP1 to CP6, β-NPB, or any of the same:

[0426]

[0427]

[0428] [Electronic device]

[0429] The light-emitting element may be included in various electronic devices. For example, an electronic device including the light-emitting element may be a light-emitting device, an authentication device, etc.

[0430] The electronic device (e.g., a light-emitting device) may further include, in addition to the light-emitting element, i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and / or the color conversion layer may be disposed in at least one direction of propagation of light emitted from the light-emitting element. For example, the light emitted from the light-emitting element may be blue light or white light. Refer to the description of the light-emitting element above. According to one embodiment, the color conversion layer may include quantum dots.

[0431] The electronic device may include a first substrate. The first substrate may include a plurality of subpixel regions, the color filter may include a plurality of color filter regions corresponding to each of the plurality of subpixel regions, and the color conversion layer may include a plurality of color conversion regions corresponding to each of the plurality of subpixel regions.

[0432] A pixel defining film is placed between the plurality of subpixel regions above to define each subpixel region.

[0433] The above color filter may further include a plurality of color filter regions and a light-blocking pattern disposed between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light-blocking pattern disposed between the plurality of color conversion regions.

[0434] The plurality of color filter regions (or plurality of color conversion regions) comprises a first region emitting a first color light; a second region emitting a second color light; and / or a third region emitting a third color light, wherein the first color light, the second color light, and / or the third color light may have different maximum emission wavelengths. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, the plurality of color filter regions (or plurality of color conversion regions) may include quantum dots. Specifically, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include quantum dots. Refer to the description of quantum dots as provided in this specification. The first region, the second region, and / or the third region may each further include scatterers.

[0435] For example, the light-emitting element may emit a first light, the first region may absorb the first light to emit a first-1 color light, the second region may absorb the first light to emit a second-1 color light, and the third region may absorb the first light to emit a third-1 color light. In this case, the first-1 color light, the second-1 color light, and the third-1 color light may have different maximum emission wavelengths. Specifically, the first light may be blue light, the first-1 color light may be red light, the second-1 color light may be green light, and the third-1 color light may be blue light.

[0436] The above electronic device may further include a thin-film transistor in addition to the light-emitting element described above. The thin-film transistor may include 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 light-emitting element.

[0437] The above thin-film transistor may further include a gate electrode, a gate insulating film, etc.

[0438] The above active layer may include crystalline silicon, amorphous silicon, organic semiconductor, oxide semiconductor, etc.

[0439] The electronic device may further include a sealing portion for sealing a light-emitting element. The sealing portion may be disposed between the color filter and / or color conversion layer and the light-emitting element. The sealing portion allows light from the light-emitting element to be emitted to the outside while simultaneously blocking external air and moisture from penetrating the light-emitting element. The sealing portion may be a sealing substrate comprising a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer comprising one or more organic and / or inorganic layers. If the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.

[0440] On the sealing portion, in addition to the color filter and / or color conversion layer, various functional layers may be additionally disposed depending on the application of the electronic device. Examples of the functional layers may include a touchscreen layer, a polarizing layer, etc. The touchscreen layer may be a pressure-sensitive touchscreen layer, a capacitive touchscreen layer, or an infrared touchscreen layer. The authentication device may be, for example, a biometric authentication device that authenticates an individual using biometric information (e.g., fingertip, pupil, etc.).

[0441] The authentication device described above may further include means for collecting biometric information in addition to the light-emitting element described above.

[0442] The above electronic device can be applied to various displays, light sources, lighting, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game consoles, medical devices (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram display devices, ultrasound diagnostic devices, endoscope display devices), fish finders, various measuring instruments, instruments (e.g., instruments for vehicles, aircraft, and ships), projectors, etc.

[0443] [Explanation of Figures 2 and 3]

[0444] FIG. 2 is a cross-sectional view of a light-emitting device according to one embodiment of the present invention.

[0445] The light-emitting device of FIG. 2 includes a substrate (100), a thin-film transistor (TFT), a light-emitting element, and a sealing portion (300) that seals the light-emitting element.

[0446] The substrate (100) may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer (210) may be disposed on the substrate (100). The buffer layer (210) may prevent the penetration of impurities through the substrate (100) and may serve to provide a flat surface on the upper surface of the substrate (100).

[0447] A thin-film transistor (TFT) may be disposed on the buffer layer (210). The thin-film transistor (TFT) may include an active layer (220), a gate electrode (240), a source electrode (260), and a drain electrode (270).

[0448] The active layer (220) may include an inorganic semiconductor, an organic semiconductor, or an oxide semiconductor such as silicon or polysilicon, and includes a source region, a drain region, and a channel region.

[0449] A gate insulating film (230) for insulating the active layer (220) and the gate electrode (240) may be disposed on the upper part of the active layer (220), and a gate electrode (240) may be disposed on the upper part of the gate insulating film (230).

[0450] An interlayer insulating film (250) may be disposed on the upper portion of the gate electrode (240). The interlayer insulating film (250) is disposed between the gate electrode (240) and the source electrode (260) and between the gate electrode (240) and the drain electrode (270) to insulate them.

[0451] A source electrode (260) and a drain electrode (270) may be disposed on the interlayer insulating film (250). The interlayer insulating film (250) and the gate insulating film (230) may be formed so as to expose the source region and the drain region of the active layer (220), and the source electrode (260) and the drain electrode (270) may be disposed to be in contact with the exposed source region and the drain region of the active layer (220).

[0452] Such a thin-film transistor (TFT) can be electrically connected to a light-emitting element to drive the light-emitting element and is covered and protected by a passivation layer (280). The passivation layer (280) may include an inorganic insulating film, an organic insulating film, or a combination thereof. A light-emitting element is provided on the passivation layer (280). The light-emitting element includes a first electrode (110), an intermediate layer (130), and a second electrode (150).

[0453] The first electrode (110) may be disposed on the passivation layer (280). The passivation layer (280) may be disposed so as to expose a certain area without covering the entire drain electrode (270), and the first electrode (110) may be disposed to be connected to the exposed drain electrode (270).

[0454] A pixel defining film (290) including an insulating material may be disposed on the first electrode (110). The pixel defining film (290) exposes a predetermined area of ​​the first electrode (110), and an intermediate layer (130) may be formed in the exposed area. The pixel defining film (290) may be a polyimide or polyacrylic-based organic film. Although not shown in FIG. 2, some or more layers of the intermediate layer (130) may extend to the upper part of the pixel defining film (290) and be disposed in the form of a common layer.

[0455] A second electrode (150) is disposed on the intermediate layer (130), and a capping layer (170) may be additionally formed on the second electrode (150). The capping layer (170) may be formed to cover the second electrode (150).

[0456] A sealing portion (300) may be disposed on the capping layer (170). The sealing portion (300) may be disposed on a light-emitting element and serve to protect the light-emitting element from moisture or oxygen. The sealing portion (300) may include an inorganic film comprising silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), an epoxy resin (e.g., AGE (aliphatic glycidyl ether), etc.) or any combination thereof; or a combination of an inorganic film and an organic film.

[0457] FIG. 3 is a cross-sectional view of a light-emitting device according to another embodiment of the present invention.

[0458] The light-emitting device of FIG. 3 is the same light-emitting device as FIG. 2, except that a light-blocking pattern (500) and a functional area (400) are additionally disposed on the upper part of the encapsulation portion (300). The functional area (400) may be i) a color filter area, ii) a color conversion area, or iii) a combination of a color filter area and a color conversion area. According to one embodiment, the light-emitting element included in the light-emitting device of FIG. 3 may be a tandem light-emitting element.

[0459] [Manufacturing Method]

[0460] Each layer included in the hole transport region, each light-emitting layer, and each layer included in the electron transport region can be formed in a predetermined region using various methods such as vacuum deposition, spin coating, casting, LB method (Langmuir-Blodgett), inkjet printing, laser printing, and laser thermal imaging (LITI).

[0461] When each layer included in the hole transport region, the emissive layer, and each layer included in the electron transport region are formed by vacuum deposition, the deposition conditions are, for example, a deposition temperature of about 100 to about 500°C, and about 10 -8 to about 10 -3 Within a vacuum level of torr and a deposition rate range of about 0.01 to about 100 Å / sec, the material to be included in the layer to be formed and the structure of the layer to be formed can be selected.

[0462] [Definition of Terms]

[0463] C3-C in this specification 60 A carbocyclic group refers to a cyclic group consisting solely of carbon atoms with 3 to 60 carbon atoms, and C1-C 60 A heterocyclic group refers to a cyclic group having 1 to 60 carbon atoms that includes a heteroatom in addition to carbon. The above C3-C 60 Carbocyclic group and C1-C60 Each heterocyclic group may be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed together. For example, the above C1-C 60 The number of ring-forming atoms in a heterocyclic group can be 3 to 61.

[0464] In this specification, the cyclic group is the above C3-C 60 Carbocyclic group and C1-C 60 Includes all heterocyclic groups.

[0465] In this specification, π electron-excess C3-C 60 cyclic group (π electron-rich C3-C 60 A cyclic group refers to a cyclic group having 3 to 60 carbon atoms that does not contain *-N=*' as a ring-forming moiety, and π electron-deficient nitrogen-containing C1-C 60 cyclic group (π electron-deficient nitrogen-containing C1-C 60 A cyclic group refers to a heterocyclic group having 1 to 60 carbon atoms containing *-N=*' as a ring-forming moiety.

[0466] for example,

[0467] The above C3-C 60The carbocyclic group may be i) group T1 or ii) a condensed ring group formed by the condensation of two or more groups T1 (e.g., cyclopentadiene group, adamantane group, norbornane group, benzene group, pentylene group, naphthalene group, azulene group, indacene group, acenaphtylene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, perylene group, pentapene group, heptylene group, naphthacene group, fisene group, hexacene group, pentacene group, rubicene group, coronene group, ovalene group, indene group, fluorene group, spiro-bifluorene group, benzofluorene group, indenophenanthrene group, or indenoanthracene group), and

[0468] The above C1-C 60A heterocyclic group is i) group T2, ii) a condensed ring group formed by the condensation of two or more groups T2, or iii) a condensed ring group formed by the condensation of one or more groups T2 and one or more groups T1 (e.g., pyrrole group, thiophene group, furan group, indole group, benzodole group, naphthoyndole group, isodole group, benzisoindole group, naphthoyisoindole group, benzocillol group, benzothiophene group, benzofuran group, carbazole group, dibenzocillol group, dibenzothiophene group, dibenzofuran group, indenocarbazole group, indolocarbazole group, benzofurocarbazole group, benzothienocarbazole group, benzocillolocarbazole group, benzodolocarbazole group, benzoindolocarbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthiophene group, Benzonaphthosilol group, benzofurodibenzofuran group, benzofurodibenzothiophen group, benzothienodibenzothiophen group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiaazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiaazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazolin group, benzoquinazolin group, phenanthroline group, sinoline group, phthalazine group, It may be the naftiridine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluoren group, azadibenzocilol group, azadibenzothiophen group, azadibenzofuran group, etc.),

[0469] The above π electron-excess C3-C 60A cyclic group is i) group T1, ii) a condensed ring group formed by condensing two or more groups T1 together, iii) group T3, iv) a condensed ring group formed by condensing two or more groups T3 together, or v) a condensed ring group formed by condensing one or more groups T3 and one or more groups T1 together (e.g., the above C3-C 60 May be carbocylic group, pyrrole group, thiophene group, furan group, indole group, benzodole group, naphthoyndole group, isodole group, benzoisoindole group, naphthoyisoindole group, benzocylol group, benzothiophene group, benzofuran group, carbazole group, dibenzocylol group, dibenzothiophene group, dibenzofuran group, indenocarbazole group, indolocarbazole group, benzofurocarbazole group, benzothienocarbazole group, benzocylololocarbazole group, benzodolocarbazole group, benzoindolocabazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthiophene group, benzonaphthocilol group, benzofurodibenzofuran group, benzofurodibenzothiophene group, benzothienodibenzothiophene group, etc.),

[0470] The above π electron-deficient nitrogen-containing C1-C 60A cyclic group is i) group T4, ii) a condensed ring group formed by the condensation of two or more groups T4, iii) a condensed ring group formed by the condensation of one or more groups T4 and one or more groups T1, iv) a condensed ring group formed by the condensation of one or more groups T4 and one or more groups T3, or v) a condensed ring group formed by the condensation of one or more groups T4, one or more groups T1, and one or more groups T3 (e.g., pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiaazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiaazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, It may be the isoquinoline group, benzoquinoline group, benzisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazolin group, benzoquinazolin group, phenanthroline group, sinoline group, phthalazine group, naftiridine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluoren group, azadibenzocilol group, azadibenzothiophen group, azadibenzofuran group, etc.),

[0471] The above group T1 is a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, norbornane (or, bicyclo[2.2.1]heptane)) group, norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.1.1]octane group, or a benzene group, and

[0472] The above group T2 is a furan group, a thiophene group, a 1H-pyrrole group, a silol group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiaazole group, a thiadiazole group, an azacilol group, an azaborol group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group, and

[0473] The above group T3 is a furan group, a thiophene group, an 1H-pyrrole group, a silol group, or a borole group, and

[0474] The above group T4 may be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazol group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiaazole group, a thiadiazole group, an azacilol group, an azaborol group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group.

[0475] In this specification, the cyclic group, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, π electron-excess C3-C 60 Cyclic group or π electron-deficient nitrogenous C1-C 60 The term "cyclic group" may be a group condensed to any cyclic group, a monovalent group, or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) depending on the structure of the chemical formula in which the term is used. For example, "benzene group" may be a benzo group, a phenyl group, a phenylene group, etc., which can be easily understood by a person skilled in the art depending on the structure of the chemical formula containing the "benzene group."

[0476] For example, 1 valence C3-C 60 Carbocyclic group and 1 valence C1-C 60 An example of a heterocyclic group is 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, C1-C 60 It may include a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocondensed polycyclic group, and a divalent C3-C 60 Carbocyclic group and 1 valence C1-C 60 An example of a heterocyclic group is C3-C 10 Cycloalkylene group, C1-C 10 Heterocycloalkylene group, C3-C 10 Cycloalkenylene group, C1-C 10 Heterocycloalkenylene group, C6-C 60 Aryllene group, C1-C 60 It may include a heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group.

[0477] C1-C in this specification 60The alkyl group refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples thereof include a methyl group, an ethyl group, n -Propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group, n -Pentyl, 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, iso-octyl group, sec -Octyl group, tert -Octyl group, n -Nonilgi, Isononilgi, sec -Playing, tert -Playing, n - Decyl group, isodecyl group, sec -Desil, tert - Includes decyl groups, etc. C1-C in this specification. 60 The alkylene group is the C1-C 60 It refers to a divalent group having the same structure as an alkyl group.

[0478] C2-C in this specification 60 The alkenyl group is C2-C 60 It refers to a monovalent hydrocarbon group comprising one or more carbon-carbon double bonds at the middle or terminal of an alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, a butenyl group, etc. In this specification, C2-C 60 The alkenylene group is the above C2-C 60 It refers to a divalent group having the same structure as an alkenyl group.

[0479] C2-C in this specification 60 The alkynyl group is C2-C 60It refers to a monovalent hydrocarbon group comprising one or more carbon-carbon triple bonds at the middle or terminal of an alkyl group, and specific examples thereof include ethinyl groups, propynyl groups, etc. In this specification, C2-C 60 The alkynylene group is the above C2-C 60 It refers to a divalent group having the same structure as an alkynyl group.

[0480] C1-C in this specification 60 The alkoxy group is -OA 101 (Here, A 101 The above C1-C 60 It refers to a monovalent group having the chemical formula of an alkyl group, and specific examples thereof include a methoxy group, an ethoxy group, an isopropyloxy group, etc.

[0481] C3-C in this specification 10 A cycloalkyl group refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, norbornanyl group (or, a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.1.1]octyl group, etc. In this specification, C3-C 10 The cycloalkylene group is the C3-C 10 It refers to a divalent group having the same structure as a cycloalkyl group.

[0482] C1-C in this specification 10A heterocycloalkyl group refers to a monovalent cyclic group having 1 to 10 carbon atoms, comprising at least one heteroatom as a ring-forming atom in addition to a carbon atom, and specific examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, etc. In this specification, C1-C 10 The heterocycloalkylene group is the C1-C 10 It refers to a divalent group having the same structure as a heterocycloalkyl group.

[0483] C3-C in this specification 10 A cycloalkenyl group refers to a monovalent cyclic group having 3 to 10 carbon atoms, having at least one carbon-carbon double bond within the ring, but not having aromaticity; specific examples thereof include cyclopentenyl groups, cyclohexenyl groups, cycloheptenyl groups, etc. In this specification, C3-C 10 The cycloalkenylene group is the above C3-C 10 It refers to a divalent group having the same structure as a cycloalkenyl group.

[0484] C1-C in this specification 10 The heterocycloalkenyl group is a monovalent cyclic group having 1 to 10 carbon atoms, comprising, in addition to the carbon atom, at least one heteroatom as a ring-forming atom, and has at least one double bond within the ring. The C1-C 10 Specific examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazoleyl groups, 2,3-dihydrofuranyl groups, 2,3-dihydrothiophenyl groups, etc. In this specification, C1-C 10 The heterocycloalkenylene group is the above C1-C 10 It refers to a divalent group having the same structure as a heterocycloalkenyl group.

[0485] C6-C in this specification 60An aryl group refers to a monovalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms, and C6-C 60 An arylene group refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. The above C6-C 60 Specific examples of aryl groups include phenyl group, pentalenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, Includes hepthalenyl group, naphthacenyl group, fisenyl group, hexacenyl group, penthacenyl group, rubisenyl group, coronenyl group, ovalenyl group, etc. The above C6-C 60 Aryl group and C6-C 60 If the arylene group contains two or more rings, the two or more rings can be condensed together.

[0486] C1-C in this specification 60 A heteroaryl group refers to a monovalent group having a heterocyclic aromatic system having 1 to 60 carbon atoms, comprising at least one heteroatom as a ring-forming atom in addition to a carbon atom, and C1-C 60 A heteroarylene group refers to a divalent group having a heterocyclic aromatic system having 1 to 60 carbon atoms, which additionally includes at least one heteroatom as a ring-forming atom in addition to the carbon atoms. 60 Specific examples of heteroaryl groups include pyridinyl groups, pyrimidinyl groups, pyrazinyl groups, pyridazinyl groups, triazinyl groups, quinolinyl groups, benzoquinolinyl groups, isoquinolinyl groups, benzisoquinolinyl groups, quinoxalinyl groups, benzoquinoxalinyl groups, quinazolinyl groups, benzoquinazolinyl groups, cinolinyl groups, phenanthrolinyl groups, phthalazinyl groups, naphthalidinyl groups, etc. The above C1-C 60 Heteroaryl group and C1-C 60 When a heteroarylene group contains two or more rings, the two or more rings can be condensed together.

[0487] In this specification, a monovalent non-aromatic condensed polycyclic group refers to a monovalent group (e.g., having 8 to 60 carbon atoms) in which two or more rings are condensed together, and the entire molecule contains only carbon as a ring-forming atom and has non-aromaticity. Specific examples of the monovalent non-aromatic condensed polycyclic group include indenyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, indenopenantrenyl groups, indenoanthracenyl groups, etc. In this specification, a divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

[0488] In this specification, a monovalent non-aromatic condensed heteropolycyclic group means a monovalent group (e.g., having 1 to 60 carbon atoms) in which two or more rings are condensed together, and in addition to carbon atoms as ring-forming atoms, at least one heteroatom is included, and the entire molecule is non-aromatic. Specific examples of the above monovalent non-aromatic heterocondensed polycyclic group include: a pyrrole group, a thiophenyl group, a furanyl group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzocylol group, a benzothiophenyl group, a benzofuranyl group, a carbazole group, a dibenzocylol group, a dibenzothiophenyl group, a dibenzofuranyl group, azacarbazole group, azafluorenyl group, azadibenzocylol group, azadibenzothiophenyl group, azadibenzofuranyl group, a pyrazol group, an imidazole group, a triazole group, a tetrazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a thiadiazole group, Includes benzopyrazol group, benzimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, imidazopyridinyl group, imidazopyrimidinyl group, imidazotriazinyl group, imidazopyrazinyl group, imidazopyridazinyl group, indenocarbazole group, indolocarbazole group, benzofurocarbazole group, benzothienocarbazole group, benzosilolocarbazole group, benzindolocarbazole group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, benzonaphthosilol group, benzofurodibenzofuranyl group, benzofurodibenzothiophenyl group, benzothienodibenzothiophenyl group, etc. In this specification, a divalent non-aromatic heterocondensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic heterocondensed polycyclic group.

[0489] C6-C in this specification 60 The aryloxy group is -OA 102 (Here, A 102 is the above C6-C 60 Pointing to arylgime), and the above C6-C 60The arylthio group is -SA 103 (Here, A 103 The above C6-C 60 It refers to the Arilgigiim).

[0490] "R" in this specification 10a "Is,

[0491] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, or nitro group;

[0492] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ), -P(=O)(Q 11 )(Q 12 ), or substituted or unsubstituted with any combination thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, or C1-C 60 Alkoxygenation;

[0493] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, -Si(Q 21)(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ), -P(=O)(Q 21 )(Q 22 ), or substituted or unsubstituted with any combination thereof, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 aryloxy group, or C6-C 60 Arylthiogi; or

[0494] -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), or -P(=O)(Q 31 )(Q 32 );

[0495] It could be.

[0496] Q1 to Q3, Q in this specification 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 They are independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy group; or deuterium, -F, cyano group, C1-C 60 Alkyl group, C1-C 60 C3-C substituted or unsubstituted with an alkoxy group, a phenyl group, a biphenyl group, or any combination thereof60 Carbocyclic group or C1-C 60 It can be a heterocyclic group.

[0497] In this specification, a heteroatom refers to any atom other than a carbon atom. Examples of such heteroatoms include O, S, N, P, Si, B, Ge, Se, or any combination thereof.

[0498] In this specification, "Ph" means a phenyl group, "Me" means a methyl group, "Et" means an ethyl group, and "ter-Bu" or "Bu t " represents the tert-butyl group, and "OMe" represents the methoxy group.

[0499] In this specification, "biphenyl group" means "phenyl group substituted with a phenyl group." The "biphenyl group" is a substituent of "C6-C 60 It belongs to the "substituted phenyl group" which is an "aryl group".

[0500] In this specification, "terphenyl group" means "phenyl group substituted with a biphenyl group." The "terphenyl group" is a substituent of "C6-C 60 C6-C substituted with aryl groups 60 It belongs to the "substituted phenyl group" which is an "aryl group".

[0501] In this specification, * and *' refer to bonding sites with adjacent atoms in the corresponding chemical formulas, unless otherwise defined.

[0502] [Method for manufacturing a light-emitting element]

[0503] A method for manufacturing a light-emitting device according to another aspect includes the step of forming a hole transport region on a first electrode, and

[0504] The step of forming the hole transport region includes a solution process step using a hole transportable composition.

[0505] For a description of the hole transportable composition mentioned above, refer to what is described in this specification.

[0506] The above solution process step can be performed by spin coating, slot coating, dip coating, bar coating, roll coating, gravure coating, microgravure coating, wire coating, spray coating, inkjet printing, nozzle printing, screen printing, flexo printing, offset printing, or casting.

[0507] According to one embodiment, the step of forming the hole transport region further comprises the step of thermally curing or photocuring the azide-based compound and the polymer compound; or the step of removing the solvent.

[0508] The step of removing the solvent may be performed in a temperature range of 150°C to 250°C, for example, a temperature range of 180°C to 220°C.

[0509] According to one embodiment, the method for manufacturing the light-emitting element further comprises the step of forming a light-emitting layer on the hole transport region, and

[0510] The step of forming the light-emitting layer includes a solution process step using a second composition, and the second composition may include a host material, a dopant material, and a second solvent.

[0511] Refer to the above description regarding the solvent for the second solvent among the above second compositions, and refer to the above description regarding the host material and dopant material.

[0512] Hereinafter, a compound and a light-emitting device according to one embodiment of the present invention will be described in more detail with reference to synthesis examples and embodiments. In the following synthesis examples, the molar equivalent of A and the molar equivalent of B are the same in the expression "B was used instead of A."

[0513] [Synthetic Example]

[0514] Synthesis Example 1: Synthesis of Compound 1

[0515] A mixture of 5-Bromoindoline (10 g, 47 mmol) and POCl3 (50 mL) was stirred at 100°C for 8 hours, then the mixture was placed in 0°C water and neutralized with NaOH. The neutralized brown precipitate was purified by column and recrystallized in acetone to obtain a yellow solid (5.2 g, 57%).

[0516] Compound 1 was synthesized with a 95% yield by dissolving the above yellow intermediate (5.2g, 9mmol) and sodium azide (2.8g, 43mol, 4.8 equivalents) in DMF solvent in a flask under a nitrogen atmosphere, stirring at room temperature for 12 hours, and then purifying by column.

[0517] <Compound 1>

[0518]

[0519] Synthesis Example 2: Synthesis of Compound 2

[0520] A mixture of 2-indolinone (10 g, 75 mmol) and POCl3 (50 mL) was stirred at 100°C for 8 hours, the reaction mixture was placed in 0°C water, and neutralized with NaOH. After column purification of the neutralized brown precipitate, it was recrystallized in acetone to obtain a yellow solid (5.3 g, 61%).

[0521] In a flask under a nitrogen atmosphere, the first yellow intermediate (5.3g, 15mmol) and sodium hydride (1.2g, 53mmol, 3.5 equivalents) were dissolved in DMF solvent and stirred at room temperature for 30 minutes. Then, 1-bromo-2-iodoethane (14g, 60mmol, 4 equivalents) was injected via syringe and refluxed for 2 hours. The reaction mixture was added to water, extracted with DCM, and water was removed with MgSO4. The second yellow intermediate (8.2g, 82%) was obtained by column purification. In a flask under a nitrogen atmosphere, the second yellow intermediate (8.2g, 12mmol) and sodium azide (3.8g, 59mol, 4.8 equivalents) were dissolved in DMF solvent and stirred at room temperature for 12 hours. Compound 2 was synthesized with a 92% yield by column purification.

[0522] <Compound 2>

[0523]

[0524] Synthesis Example 3: Synthesis of Compound 3

[0525] A mixture of 2-indolinone (10 g, 75 mmol) and POCl3 (50 mL) was stirred at 100°C for 8 hours, then the reaction mixture was placed in 0°C water and neutralized with NaOH. The neutralized brown precipitate was purified by column and recrystallized in acetone to obtain a yellow solid (5.3 g, 61%).

[0526] The first yellow intermediate (5.3 g, 15 mmol) and sodium hydride (1.2 g, 53 mmol, 3.5 equivalents) were dissolved in DMF solvent in a flask under a nitrogen atmosphere and stirred at room temperature for 30 minutes. Then, 1-bromo-10-iododecane (21 g, 60 mmol, 4 equivalents) was injected via syringe and refluxed for 2 hours. The reaction mixture was added to water, extracted with DCM, and water was removed with MgSO4. The second yellow intermediate (10.3 g, 68%) was obtained by column purification.

[0527] Compound 3 was synthesized with a 90% yield by dissolving the second yellow intermediate (10.3g, 10mmol) and sodium azide (3.2g, 49mol, 4.8 equivalents) in DMF solvent in a flask under a nitrogen atmosphere, stirring at room temperature for 12 hours, and then purifying by column.

[0528] <Compound 3>

[0529]

[0530] Synthesis Example 4: Synthesis of Compound 4

[0531] A mixture of 2-indolinone (10 g, 75 mmol) and POCl3 (50 mL) was stirred at 100°C for 8 hours, after which the reaction mixture was placed in water at 0°C and neutralized with NaOH. The neutralized brown precipitate was purified by column and then recrystallized in acetone to obtain a yellow solid (5.3 g, 61%).

[0532] The first yellow intermediate (5.3 g, 15 mmol) and sodium hydride (1.2 g, 53 mmol, 3.5 equivalents) were dissolved in DMF solvent in a flask under a nitrogen atmosphere and stirred at room temperature for 30 minutes. Then, 1-chloro-20-iodoicosane (26 g, 60 mmol, 4 equivalents) was injected via syringe and refluxed for 2 hours. The reaction mixture was added to water, extracted with DCM, and water was removed with MgSO4. The second yellow intermediate (8.3 g, 63%) was obtained by column purification.

[0533] Compound 4 was synthesized with an 86% yield by dissolving the second yellow intermediate (8.3g, 9.5mmol) and sodium azide (3.0g, 46mol, 4.8 equivalents) in DMF solvent in a flask under a nitrogen atmosphere, stirring at room temperature for 12 hours, and then purifying by column.

[0534] <Compound 4>

[0535]

[0536] of the compounds synthesized in the above synthesis example 1The H NMR results are shown in Table 1 below.

[0537] Compound number 1 H NMR (CDCl3, 400 MHz) 1 11.8 (s, 3H), 8.03 (s, 3H), 7.5-7.8 (m, 6H), 2 8.3 (d, 3H), 7.3-7.7 (m, 9H), 3.9 (t, 6H), 1.9 (t, 6H) 3 8.3 (d, 3H), 7.3-7.7 (m, 9H), 4.2 (t, 6H), 1.7 (m, 6H), 1.5 (t, 6H), 1.2-1.4 (m, 42H) 4 8.3 (d, 3H), 7.3-7.7 (m, 9H), 4.2 (t, 6H), 1.7 (m, 6H), 1.5 (t, 6H), 1.2-1.4 (m, 102H)

[0538] Other compounds besides those shown in Table 1 can also be easily recognized by those skilled in the art by referring to the synthesis routes and raw materials above.

[0539] [Example]

[0540] Preparation of hole transportable composition 1

[0541] A hole-transporting composition 1 at a concentration of 1.5% was prepared using compound 1 as anisole as a solvent.

[0542] <Compound 1>

[0543]

[0544] Preparation of hole-transporting compositions 2 to 4 and comparative compositions 1 to 5

[0545] Hole transport compositions 2 to 4 and comparative compositions 1 to 5 were prepared in the same manner as hole transport composition 1, except that the compounds listed in Table 2 below were used instead of compound 1.

[0546] <Compound 2>

[0547]

[0548] <Compound 3>

[0549]

[0550] <Compound 4>

[0551]

[0552] Triindole

[0553]

[0554] <Compound A>

[0555]

[0556] <Compound B>

[0557]

[0558] <Compound C>

[0559]

[0560] <Compound D>

[0561]

[0562] Evaluation Example 1

[0563] After fabricating a monolayer with a thickness of 400 Å using the hole transportable compositions 1 to 4 and comparative compositions 1 to 5 prepared above, the monolayer was heat-treated at 200°C for 30 minutes, and the UV spectrum of the monolayer was measured.

[0564] 50 µl of methyl benzoate was dropped onto the top of each monolayer and left for 30 minutes. Then, the solvent was absorbed with a wiper, and after leaving the monolayer at 100°C for 1 minute, the UV spectrum of the monolayer was measured.

[0565] And, the residual film rate calculated for each monolayer as follows is shown in Table 2 below.

[0566] Residual film rate = (UV measurement area after dropping solvent (methyl benzoate) (solvent treatment) and standing for 30 minutes) / (UV measurement area before solvent treatment)

[0567] In addition, hole mobility was measured using a space charge limited current with the above hole transport compositions 1 to 4 and comparative compositions 1 to 5, and the results are shown in Table 2 below.

[0568] composition compound Residual film rate (%) Hole mobility (cm²) 2 / Vs) Hole transport composition 1 Compound 1 100 1.2 x 10 -2 Hole transportable composition 2 Compound 2 100 8.5 x 10 -3 Hole transportable composition 3 Compound 3 100 5.6 x 10 -3 Hole transport composition 4 Compound 4 100 1.2 x 10 -3 Comparative composition 1 Tree Dol 0 2.0 x 10 -2 Comparative composition 2 Compound A 100 5.4 x 10 -4 Comparative composition 3 Compound B 100 0.9 x 10 -3 Comparative composition 4 Compound C 100 7.0 x 10 -4 Comparative composition 5 Compound D 0 2.6 x 10 -4

[0569] Referring to Table 2, it was found that the hole transport composition containing a heterocyclic compound according to one embodiment facilitates monolayer formation and exhibits excellent hole mobility. In particular, hole transport compositions 1 to 4 exhibited superior hole mobility compared to comparative compositions 2 to 5. Comparative compositions 1 and 5 did not form monolayers.

[0570] Although the present invention has been described with reference to the above synthesis examples and embodiments, this is merely illustrative, and those skilled in the art will understand that various modifications and equivalent alternative embodiments are possible therefrom. Accordingly, the true technical scope of protection of the present invention should be determined by the technical spirit of the appended claims. Explanation of the symbols

[0571] 10: Organic light-emitting diode 110: First electrode 150: Organic layer 190: Second electrode

Claims

Claim 1 Heterocyclic compounds represented by the following chemical formula 1: <Chemical Formula 1> In the above Chemical Formula 1, L 11 to L 13 and L 21 to L 23 are independent of each other, at least one R 10a C2-C substituted or unsubstituted 20 alkenylene group, or at least one R 10a C2-C substituted or unsubstituted 20 It is an alkynylene group, and a11 to a13 and a21 to a23 are independently 1, 2, 3, 4 or 5, and Z 11 To Z 13 , Z 21 To Z 23 and R1 to R9 are independently hydrogen, deuterium, azide group (-N3), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazino group, hydrazono group, at least one R 10a C1-C substituted or unsubstituted 60 alkyl group, at least one R 10a C2-C substituted or unsubstituted 60 alkenyl group, at least one R 10a C2-C substituted or unsubstituted 60 alkynyl group, at least one R 10a C1-C substituted or unsubstituted 60 Alkoxy group, at least one R 10a C3-C substituted or unsubstituted 10 Cycloalkyl group, at least one R 10a C1-C substituted or unsubstituted 10 Heterocycloalkyl group, at least one R 10a C3-C substituted or unsubstituted 10 Cycloalkenyl group, at least one R 10a C1-C substituted or unsubstituted 10 Heterocycloalkenyl group, at least one R 10a C6-C substituted or unsubstituted 60 Arylgi, at least one R 10a C6-C substituted or unsubstituted 60 aryloxy group, at least one R 10a C6-C substituted or unsubstituted 60 Arylthiogi, at least one R 10a C1-C substituted or unsubstituted 60 Heteroaryl group, at least one R 10a C1-C substituted or unsubstituted 60 Heteroaryloxy group, at least one R 10a C1-C substituted or unsubstituted 60 Heteroaryltio group, at least one R 10a A monovalent non-aromatic condensed polycyclic group substituted or unsubstituted with R, at least one R 10a A monovalent non-aromatic heterocondensed polycyclic group substituted or unsubstituted with -Si(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) or -P(=S)(Q1)(Q2), and Z 11 To Z 13 , Z 21 To Z 23 and at least one of R1 to R9 is -N3, and Z 11 To Z 13 In the case where all of these are -N3, -(L 21 ) a21 -Z 21 , -(L 22 ) a22 -Z 22 and -(L 23 ) a23 -Z 23 At least one of them represents hydrogen, and the R 10a is, deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, or nitro group; deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ), -P(=O)(Q 11 )(Q 12 ), or substituted or unsubstituted with any combination thereof, 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, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ), -P(=O)(Q 21 )(Q 22 ), or substituted or unsubstituted with any combination thereof, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 aryloxy group, or C6-C 60 Arylthio group; or-Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), or -P(=O)(Q 31 )(Q 32 ); and, above Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 They are independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy group; or deuterium, -F, cyano group, C1-C 60 Alkyl group, C1-C 60 C3-C substituted or unsubstituted with an alkoxy group, a phenyl group, a biphenyl group, or any combination thereof 60 Carbocyclic group or C1-C 60 A heterocyclic group; and the above heterocyclic compound is not the following compound B: <Compound B> . Claim 2 In paragraph 1, Z 11 To Z 13 These are heterocyclic compounds, each with -N3. Claim 3 In paragraph 1, Z 21 To Z 23 These are heterocyclic compounds, each with -N3. Claim 4 In claim 1, a heterocyclic compound represented by either of the following chemical formulas 2A and 2B: <Chemical Formula 2A> <Chemical Formula 2B> Among the above chemical formulas 2A and 2B, L 11 to L 13 , L 21 to L 23 , Z 11 To Z 13 , Z 21 To Z 23 For descriptions of and R1 to R9, refer to Paragraph 1, and R 11 to R 13 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazino group, hydrazono group, at least one R 10a C1-C substituted or unsubstituted 60 alkyl group, at least one R 10a C2-C substituted or unsubstituted 60 alkenyl group, at least one R 10a C2-C substituted or unsubstituted 60 alkynyl group, at least one R 10a C1-C substituted or unsubstituted 60 Alkoxy group, at least one R 10a C3-C substituted or unsubstituted 10 Cycloalkyl group, at least one R 10a C1-C substituted or unsubstituted 10 Heterocycloalkyl group, at least one R 10a C3-C substituted or unsubstituted 10 Cycloalkenyl group, at least one R 10a C1-C substituted or unsubstituted 10 Heterocycloalkenyl group, at least one R 10a C6-C substituted or unsubstituted 60 Arylgi, at least one R 10a C6-C substituted or unsubstituted 60 aryloxy group, at least one R 10a C6-C substituted or unsubstituted 60 Arylthiogi, at least one R 10a C1-C substituted or unsubstituted 60 Heteroaryl group, at least one R 10a C1-C substituted or unsubstituted 60 Heteroaryloxy group, at least one R 10a C1-C substituted or unsubstituted 60 Heteroaryltio group, at least one R 10a A monovalent non-aromatic condensed polycyclic group substituted or unsubstituted with R, at least one R 10a A monovalent non-aromatic heterocondensed polycyclic group substituted or unsubstituted with -Si(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) or -P(=S)(Q1)(Q2), and R 10a Refer to Paragraph 1 for an explanation of... Claim 5 In paragraph 1, L 11 to L 13 and L 21 to L 23 are independently of each other, an ethylene group, a propenylene group, a butenylene group, a butadienylene group, a pentenylene group, a pentadienylene group, an ethynylene group, a propynylene group, or a butynylene group; or deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amido group, a hydrazino group, a hydrazono group, and a C1-C 10 A heterocyclic compound substituted with at least one of the alkyl groups, such as a methylene group, ethylene group, propylene group, butylene group, pentylene group, ethenylene group, propenylene group, butenylene group, butadienylene group, pentenylene group, pentadienylene group, ethynylene group, propynylene group, or butynylene group. Claim 6 In paragraph 1, R1 to R9 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 alkyl group or C1-C 20 Alkoxy group; substituted with deuterium, -F, -Cl, -Br, -I, cyano group, phenyl group, biphenyl group, or any combination thereof, C1-C 20 alkyl group or C1-C 20 A heterocyclic compound comprising an alkoxy group; or a group represented by any one of the following chemical formulas 5-1 to 5-26 and 6-1 to 6-55: Among the above chemical formulas 5-1 to 5-26 and 6-1 to 6-55, Y 31 and Y 32 are independently of each other, O, S, C(Z 33 )(Z 34 ), N(Z 33 ) or Si(Z 33 )(Z 34 ) and,Z 31 To Z 34 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazino group, hydrazono group, C1-C 20 Alkyl group, C2-C 20 alkenyl group, C2-C 20 alkynyl group, C1-C 20 Selected from alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyridinyl group, pyrimidinyl group, carbazoleyl group and triazinyl group, e2 is 1 or 2, e3 is an integer selected from 1 to 3, e4 is an integer selected from 1 to 4, e5 is an integer selected from 1 to 5, e6 is an integer selected from 1 to 6, e7 is an integer selected from 1 to 7, e9 is an integer selected from 1 to 9, and * is a bonding site with an adjacent atom. Claim 7 In paragraph 1, R1 to R9 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 alkyl group or C1-C 20 Alkoxy group; substituted with deuterium, -F, -Cl, -Br, -I, cyano group, phenyl group, biphenyl group, or any combination thereof, C1-C 20 alkyl group or C1-C 20 Alkoxy group; phenyl group, biphenyl group, terphenyl group, penthalenyl group, indenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, dibenzoflurenyl group, carbazoleyl group, acridinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group or dibenzocarbazoleyl group; or deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 Alkyl group, C1-C 20 A heterocyclic compound substituted with an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzoflurenyl group, a dibenzoflurenyl group, a carbazoleyl group, an acridinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazoleyl group, or a dibenzocarbazoleyl group. Claim 8 In claim 1, a heterocyclic compound represented by either of the following chemical formulas 3A-3 and 3B-2: <Chemical Formula 3A-3> <Chemical Formula 3B-2> In the above chemical formulas 3A-3 and 3B-2, m1, m2 and m3 are 1, 2, 3, 4 or 5, respectively. Claim 9 In claim 1, the heterocyclic compound represented by the above chemical formula 1 is any one of the following compounds 6 and 7, heterocyclic compound: <Compound 6> <Compound 7> . Claim 10 A hole-transporting composition comprising a heterocyclic compound of any one of claims 1 to 9. Claim 11 In claim 10, the hole-transporting composition further comprises a solvent, and the solvent is C6-C 20 Aliphatic hydrocarbons, C5-C 20 A hole-transporting composition comprising an aromatic hydrocarbon, chloroform, methylene chloride, ethyl acetate, ethylene glycol, diethylene glycol, or any combination thereof. Claim 12 A light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an intermediate layer including a light-emitting layer interposed between the first electrode and the second electrode; a heterocyclic compound of any one of claims 1 to 9; a polymer comprising repeating units derived from the heterocyclic compound; or any combination thereof. Claim 13 A light-emitting element comprising: a first electrode; a second electrode facing the first electrode; and an intermediate layer including a light-emitting layer interposed between the first electrode and the second electrode; and a polymer comprising repeating units derived from the heterocyclic compound, wherein the repeating units derived from the heterocyclic compound are represented by any one of the following chemical formulas 1-1 to 1-4: <Chemical Formula 1-1> <Chemical Formula 1-2> <Chemical Formula 1-3> <Chemical Formula 1-4> L in the above chemical formulas 1-1 to 1-4 11 to L 13 , L 21 to L 23 For descriptions of and R1 to R9, refer to Paragraph 1, and R 11 to R 13 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazino group, hydrazono group, at least one R 10a C1-C substituted or unsubstituted 60 alkyl group, at least one R 10a C2-C substituted or unsubstituted 60 alkenyl group, at least one R 10a C2-C substituted or unsubstituted 60 alkynyl group, at least one R 10a C1-C substituted or unsubstituted 60 Alkoxy group, at least one R 10a C3-C substituted or unsubstituted 10 Cycloalkyl group, at least one R 10a C1-C substituted or unsubstituted 10 Heterocycloalkyl group, at least one R 10a C3-C substituted or unsubstituted 10 Cycloalkenyl group, at least one R 10a C1-C substituted or unsubstituted 10 Heterocycloalkenyl group, at least one R 10a C6-C substituted or unsubstituted 60 Arylgi, at least one R 10a C6-C substituted or unsubstituted 60 aryloxy group, at least one R 10a C6-C substituted or unsubstituted 60 Arylthiogi, at least one R 10a C1-C substituted or unsubstituted 60 Heteroaryl group, at least one R 10a C1-C substituted or unsubstituted 60 Heteroaryloxy group, at least one R 10a C1-C substituted or unsubstituted 60 Heteroaryltio group, at least one R 10a A monovalent non-aromatic condensed polycyclic group substituted or unsubstituted with R, at least one R 10a A monovalent non-aromatic heterocondensed polycyclic group substituted or unsubstituted with -Si(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) or -P(=S)(Q1)(Q2), and R 10a Refer to Paragraph 1 for an explanation of... Claim 14 A light-emitting device according to claim 12, wherein the first electrode is an anode and the second electrode is a cathode, and the intermediate layer includes a hole transport region interposed between the first electrode and the light-emitting layer, and the hole transport region includes the heterocyclic compound, the polymer, or any combination thereof. Claim 15 In claim 14, the above-mentioned hole transport region comprises at least one selected from a hole injection layer, a hole transport layer, a buffer layer, a light-emitting auxiliary layer, and an electron blocking layer, a light-emitting device. Claim 16 In claim 12, the light-emitting element, wherein the light-emitting layer comprises a host and a dopant. Claim 17 A light-emitting device according to claim 12, further comprising an electron transport region interposed between the light-emitting layer and the second electrode, wherein the electron transport region comprises at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer. Claim 18 A method for manufacturing a light-emitting device comprising the step of forming a hole transport region on a first electrode, wherein the step of forming the hole transport region comprises a solution process step using a hole transportable composition, and the hole transportable composition comprises a heterocyclic compound of any one of claims 1 to 9. Claim 19 An electronic device including the light-emitting element of paragraph 12. Claim 20 An electronic device according to claim 19, further comprising a thin-film transistor, wherein the thin-film transistor comprises a source electrode and a drain electrode, and the first electrode of the light-emitting element is electrically connected to the source electrode or the drain electrode.

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