Organometallic compound and light-emitting element comprising the same

Abstract

The present invention discloses an organometallic compound represented by the following Chemical Formula 1 and a light-emitting element comprising the same: <Chemical Formula 1> For detailed description of Chemical Formula 1, refer to the description in this specification.

Description

Technical Field

[0001] The present invention relates to an organometallic compound, a light-emitting element comprising the same, and an electronic device comprising the light-emitting element. Background Art

[0002] Among light-emitting elements, organic light-emitting devices (OLEDs), as self-luminous elements, not only have a wide viewing angle and excellent contrast, but also have a short response time and excellent characteristics in terms of brightness, driving voltage, and response speed compared to existing elements.

[0003] The organic light-emitting element has a first electrode disposed on top of a substrate. A hole transport region, a light-emitting layer, an electron transport region, and a second electrode may be sequentially formed on top of the first electrode. Holes injected from the first electrode migrate toward the light-emitting layer via the hole transport region, while electrons injected from the second electrode migrate toward the light-emitting layer via the electron transport region. Carriers such as the holes and electrons recombine in the light-emitting layer to generate excitons. These excitons transition from an excited state to a ground state, generating light. Summary of the Invention

[0004] Technical issues

[0005] Provided are an organometallic compound having excellent luminous efficiency, long life, and excellent color purity, and a light-emitting element using the organometallic compound.

[0006] Technical Solution

[0007] According to one aspect, an organometallic compound represented by Chemical Formula 1 is provided:

[0008] <Chemical Formula 1>

[0009]

[0010] In the chemical formula 1,

[0011] M 11 and M 12 independently of one another, platinum (Pt), palladium (Pd), nickel (Ni), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) or thulium (Tm),

[0012] X 11 、X 12 、X 131、X 132 、X 141 、X 142 、X 15 and X 16 are independently C or N,

[0013] L 11 To L 15 are independently a single bond, a double bond, *-N(Z 11 )-*'、*-B(Z 11 )-*'、*-P(Z 11 )-*'、*-C(Z 11 )(Z 12 )-*'、*-Si(Z 11 )(Z 12 )-*'、*-Ge(Z 11 )(Z 12 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(Z 11 )=*'、*=C(Z 11 )-*'、*-C(Z 11 )=C(Z 12 )-*', *-C(=S)-*' or *-C≡C-*', wherein * and *' are binding sites with adjacent atoms,

[0014] a11 to a15 are each independently an integer from 1 to 3,

[0015] A 11 To A 16 Independently of each other, C3-C 60 Carbocyclic group or C1-C 60 Heterocyclic groups,

[0016] R 11 to R 16 、Z 11 and Z 12 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, 10a Substituted or unsubstituted C1-C 60 Alkyl, with at least one R 10a Substituted or unsubstituted C2-C 60 Alkenyl, with at least one R 10a Substituted or unsubstituted C2-C 60 Alkynyl, with at least one R 10a Substituted or unsubstituted C1-C 60 Alkoxy, with at least one R10a Substituted or unsubstituted C3-C 60 Carbocyclic group, with at least one R 10a Substituted or unsubstituted C1-C 60 Heterocyclic group, with at least one R 10a Substituted or unsubstituted C6-C 60 Aryloxy, with at least one R 10a Substituted or unsubstituted C6-C 60 arylthio, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2),

[0017] b11 to b16 are independently one of integers from 0 to 10,

[0018] The R 10a for:

[0019] deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;

[0020] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy, C6-C 60 Arylthio, -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 any combination thereof, substituted or unsubstituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 alkoxy;

[0021] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy, C6-C 60 Arylthio, -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 any combination thereof substituted or unsubstituted C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy or C6-C 60 arylthio; or

[0022] -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 ),

[0023] Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 independently of one another: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 Alkoxy; or deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted or unsubstituted C3-C 60 Carbocyclic group or C1-C 60 Heterocyclic groups,

[0024] The * and *' are binding sites between adjacent atoms,

[0025] According to another aspect, a light emitting element including the organometallic compound represented by Chemical Formula 1 is provided.

[0026] According to yet another aspect, an electronic device including the light emitting element is provided.

[0027] According to some embodiments, the organometallic compound and the light-emitting element including the same may have excellent luminous efficiency, long life, and excellent color purity. BRIEF DESCRIPTION OF THE DRAWINGS

[0028] Figure 1 is a cross-sectional view schematically showing a light emitting element according to an implementation example.

[0029] Figure 2 and Figure 3 Each of them is a cross-sectional view of a light emitting device according to an implementation example.

[0030] Description of Reference Numerals

[0031] 10: Light-emitting element

[0032] 110: First electrode

[0033] 130: Middle layer

[0034] 150: Second electrode DETAILED DESCRIPTION

[0035] According to one aspect, the organometallic compound may be represented by the following Chemical Formula 1:

[0036] <Chemical Formula 1>

[0037]

[0038] In the chemical formula 1, M 11 and M 12 It can be independently platinum (Pt), palladium (Pd), nickel (Ni), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) or thulium (Tm).

[0039] According to an implementation example, M in the chemical formula 1 11 and M 12 The metals may be independently platinum (Pt), palladium (Pd), nickel (Ni), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), or osmium (Os).

[0040] In the chemical formula 1, X 11 、X 12 、X 131 、X 132 、X 141 、X 142 、X 15 and X 16 can be C or N independently of each other.

[0041] According to an implementation example, X in the chemical formula 1 132 and X 141 Can be N, X 11 、X 12 、X 131 、X 142 、X 15 and X 16 They can be C respectively.

[0042] According to an implementation example, X in the chemical formula 1 11 With M 11 The key between and X 16 With M 12 The bonds between them can be coordination bonds.

[0043] According to an implementation example, the X in the chemical formula 1 12 With M 11 The bond between the X 15 With M 12 The bonds between them can be covalent bonds.

[0044] According to an implementation example, the X in the chemical formula 1 131 With M 11 The bond between can be a covalent bond, and the X 132 With M 12 The bond between them can be a coordination bond.

[0045] According to an implementation example, the X in the chemical formula 1 132 With M 12 The bond between the X 141 With M 11 The bonds between them can be coordination bonds.

[0046] According to an implementation example, the X in the chemical formula 1 11 Can be C, X 11 With M 11 The bond between them can be a coordination bond.

[0047] According to an implementation example, the X in the chemical formula 1 12 Can be C, X 12 With M11 The bond between them can be a covalent bond.

[0048] According to an implementation example, the X in the chemical formula 1 131 Can be C, X 131 With M 11 The bond between them can be a covalent bond.

[0049] According to an implementation example, the X in the chemical formula 1 132 Can be N, X 132 With M 12 The bond between them can be a coordination bond.

[0050] According to an implementation example, the X in the chemical formula 1 141 Can be N, X 141 With M 11 The bond between them can be a coordination bond.

[0051] According to an implementation example, the X in the chemical formula 1 142 Can be C, X 142 With M 12 The bond between them can be a covalent bond.

[0052] According to an implementation example, X in the chemical formula 1 15 Can be C, X 15 With M 12 The bond between them can be a covalent bond.

[0053] According to an implementation example, X in the chemical formula 1 16 Can be C, X 16 With M 12 The bond between them can be a coordination bond.

[0054] According to an implementation example, the X in the chemical formula 1 131 and X 142 Can be C, X 132 and X 141 It can be N respectively.

[0055] In the chemical formula 1, L 11 To L 15 can be independently a single bond, a double bond, *-N(Z 11 )-*'、*-B(Z 11 )-*'、*-P(Z 11 )-*'、*-C(Z 11 )(Z 12 )-*'、*-Si(Z 11 )(Z 12 )-*'、*-Ge(Z 11 )(Z12 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(Z 11 )=*'、*=C(Z 11 )-*'、*-C(Z 11 )=C(Z 12 )-*'、*-C(=S)-*'or*-C≡C-*'. The * and *' are the binding sites between the adjacent atoms. 11 and Z 12 For instructions, please refer to the description in this manual.

[0056] According to an implementation example, the L in the chemical formula 1 11 To L 15 can be independently a single bond, *-N(Z 11 )-*'、*-P(Z 11 )-*'、*-C(Z 11 )(Z 12 )-*'、*-Si(Z 11 )(Z 12 )-*' or *-O-*'.

[0057] a11 to a15 in Chemical Formula 1 may be one of integers of 1 to 3 independently of each other.

[0058] For example, a11 to a15 may be 1 respectively, but are not limited thereto.

[0059] A in the chemical formula 1 11 To A 16 Can be C3-C independently of each other 60 Carbocyclic group or C1-C 60 Heterocyclic group.

[0060] According to an implementation example, the A in the chemical formula 1 11 Can be X 11 A five-membered ring or a condensed six-membered ring containing X 11 The five-membered ring, the A 16 Can be X 16 A five-membered ring or a condensed six-membered ring containing X 16 of a five-membered ring.

[0061] According to an implementation example, the A in the chemical formula 1 12 Can be X 12 The six-membered ring, the A 15 Can be X 15 six-membered ring.

[0062] According to an implementation example, the A in the chemical formula 1 13 Can be X 131 The six-membered ring, the A 14 Can be X 141 six-membered ring.

[0063] According to an implementation example, the A in the chemical formula 1 11 Containing X 11 The five-membered ring and the condensed six-membered ring containing X 11 The five-membered ring and the A 16 Containing X 16 The five-membered ring and the condensed six-membered ring containing X 16 The five-membered ring of may be independently a pyrrole group, a pyrazole group, an imidazole group, a triazole group, a furan group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group and a thiadiazole group.

[0064] According to an implementation example, the A in the chemical formula 1 12 Containing X 12 The six-membered ring and A 15 Containing X 15 The six-membered ring of can be independently a phenyl group, a pyridine group or a pyrimidine group.

[0065] According to an implementation example, the A in the chemical formula 1 13 Containing X 131 The six-membered ring and A 14 Containing X 141 The six-membered ring of can be independently a phenyl group, a pyridine group or a pyrimidine group.

[0066] According to an implementation example, in the chemical formula 1, The group represented by can be represented by one of the following Chemical Formulas A11-1 to A11-18:

[0067]

[0068]

[0069] In the Chemical Formula A11-1 to the Chemical Formula A11-18,

[0070] For X 11 Please refer to the description in this manual.

[0071] R 11a 、R 11b and R 11c Refer to the R 11Description, where R 11a 、R 11b and R 11c are not hydrogen,

[0072] R 11d Refer to the R 11 Description,

[0073] b114 is an integer from 0 to 4,

[0074] b113 is an integer from 0 to 3,

[0075] *For M 11 The binding site,

[0076] *' is with L 11 binding site.

[0077] According to an implementation example, the chemical formula 1 is The group represented by can be represented by one of the following Chemical Formulas A12-1 to A12-8:

[0078]

[0079] In the Chemical Formulas A12-1 to A12-8,

[0080] For X 12 Please refer to the description in this manual.

[0081] R 12a 、R 12b and R 12c Refer to the R 12 Description,

[0082] *For M 11 The binding site,

[0083] *' is with L 11 The binding site,

[0084] *” is the same as L 12 binding site.

[0085] According to an implementation example, in the chemical formula 1, The group represented by can be represented by one of the following Chemical Formulas A13-1 to A13-9:

[0086]

[0087] In the Chemical Formulas A13-1 to A13-9,

[0088] R 13a and R 13b Refer to the R 13 Description,

[0089] *1 is the same as M 11 The binding site,

[0090] *2 is the same as M 12 The binding site,

[0091] *” is the same as L 12 The binding site,

[0092] *' is with L 13 binding site.

[0093] According to an implementation example, in the chemical formula 1, The group represented by can be represented by one of the following Chemical Formulas A14-1 to A14-9:

[0094]

[0095] In the Chemical Formulas A14-1 to A14-9,

[0096] R 14a and R 14b Refer to the R 14 Description,

[0097] *1 is the same as M 11 The binding site,

[0098] *2 is the same as M 12 The binding site,

[0099] *' is with L 13 The binding site,

[0100] *” is the same as L 14 binding site.

[0101] According to an implementation example, in the chemical formula 1, The group represented by can be represented by one of the following Chemical Formulas A15-1 to A15-8:

[0102]

[0103] In the Chemical Formulas A15-1 to A15-8,

[0104] R 15a to R 15c Refer to the R 15 Description,

[0105] *For M 12 The binding site,

[0106] *' is with L 14 The binding site,

[0107] *” is the same as L 15 binding site.

[0108] According to an implementation example, in the chemical formula 1, The group represented by can be represented by one of the following Chemical Formulas A16-1 to A16-18:

[0109]

[0110] In the Chemical Formulas A16-1 to A16-18,

[0111] To X 16 Please refer to the description in this manual.

[0112] R 16a 、R 16b and R 16c Refer to the R 16 Description, but R 16a 、R 16b and R 16c are not hydrogen,

[0113] R 16d Refer to the R 16 Description,

[0114] b164 is an integer from 0 to 4,

[0115] b163 is an integer from 0 to 3,

[0116] *For M 12 The binding site,

[0117] *' is with L 15 binding site.

[0118] The R in the chemical formula 1 11 to R 16 、Z 11 and Z 12 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, 10a Substituted or unsubstituted C1-C 60 Alkyl, with at least one R 10a Substituted or unsubstituted C2-C 60Alkenyl, with at least one R 10a Substituted or unsubstituted C2-C 60 Alkynyl, with at least one R 10a Substituted or unsubstituted C1-C 60 Alkoxy, with at least one R 10a Substituted or unsubstituted C3-C 60 Carbocyclic group, with at least one R 10a Substituted or unsubstituted C1-C 60 Heterocyclic group, with at least one R 10a Substituted or unsubstituted C6-C 60 Aryloxy, with at least one R 10a Substituted or unsubstituted C6-C 60 Arylthio, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2). For the descriptions of Q1 to Q3, refer to the description in this specification.

[0119] According to an implementation example, the R in the chemical formula 1 11 to R 16 、Z 11 and Z 12 The following substituents may be present independently of one another:

[0120] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0121] deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, pyrrolidinyl, piperidinyl, phenyl, naphthyl, pyridyl, pyrimidinyl, -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 ),-P(=O)(Q 31 )(Q 32 ) or any combination thereof, substituted or unsubstituted C1-C 20Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl or C1-C 20 alkoxy;

[0122] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, pyrrolidinyl, piperidinyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -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 ),-P(=O)(Q 31 )(Q 32 ) or any combination thereof, substituted or unsubstituted cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, pyrrolidinyl, piperidinyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl or imidazopyrimidinyl; or

[0123] -Si(Q1)(Q2)(Q3), -N(Q1)(Q2) or -C(=O)(Q1). 31 To Q 33 For the descriptions, please refer to the descriptions in this manual.

[0124] According to an implementation example, the R in the chemical formula 1 11 to R 16 、Z 11 and Z 12 The following substituents may be present independently of one another:

[0125] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0126] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, pyrrolidinyl, piperidinyl, phenyl, naphthyl, pyridyl, pyrimidinyl, -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 ),-P(=O)(Q 31 )(Q 32 ) or any combination thereof, substituted or unsubstituted C1-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl or C1-C 20 alkoxy;

[0127] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl, C1-C 20 Alkoxy, pyrrolidinyl, piperidinyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 ) or any combination thereof, substituted or unsubstituted pyrrolidinyl, piperidinyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl or triazinyl; or

[0128] -Si(Q1)(Q2)(Q3) or -N(Q1)(Q2). 31 To Q 33 For the descriptions, please refer to the descriptions in this manual.

[0129] According to an implementation example, the R in the chemical formula 1 11 to R 16 、Z 11 and Z 12 The following substituents may be present independently of one another:

[0130] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0131] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, pyrrolidinyl, piperidinyl, phenyl, naphthyl, pyridyl, pyrimidinyl, -N(Q 31 )(Q 32 ) or any combination thereof, substituted or unsubstituted C1-C20 alkyl;

[0132] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 20 Alkyl, pyrrolidinyl, piperidinyl, phenyl, naphthyl, quinolinyl, -N(Q 31 )(Q 32 ) or any combination thereof, substituted or unsubstituted pyrrolidinyl, piperidinyl, phenyl, naphthyl or quinolinyl; or

[0133] -N(Q1)(Q2). 31 and Q 32 For the descriptions, please refer to the descriptions in this manual.

[0134] b11 to b16 in Chemical Formula 1 may be one of integers ranging from 0 to 10, independently of each other.

[0135] According to an implementation example, b11 to b16 in Chemical Formula 1 may be independently integers of 0 to 3, but are not limited thereto.

[0136] According to an implementation example, the organometallic compound represented by the chemical formula 1 can be selected from the following compounds 1 to 104:

[0137]

[0138]

[0139]

[0140]

[0141]

[0142] The organometallic compound represented by Chemical Formula 1 may emit blue light having a maximum emission wavelength of 430 nm to 475 nm.

[0143] The organometallic compound represented by Chemical Formula 1 may have a lowest excited triplet energy level of 2.6 eV or more and 3.0 eV or less.

[0144] In the organometallic compound, since a13 in the chemical formula 1 is an integer of 1 to 3, the structure of the bi-ligand is rigid, thereby improving the stability, and M in the chemical formula 1 is preferably 11 Can be connected to X 131 and X 141 , M12 Can be connected to X 132 and X 142 , so that the angle between the dual ligands is tilted (tilt) to inhibit the formation of excimers, therefore, the electronic element (for example, an organic light-emitting element) containing the organometallic compound can have excellent luminous efficiency, long life, and excellent color purity.

[0145] Those skilled in the art can understand the synthesis method of the organometallic compound represented by Chemical Formula 1 by referring to the synthesis examples and / or Examples described below.

[0146] At least one of the organometallic compounds represented by Chemical Formula 1 can be used in a light-emitting element (e.g., an organic light-emitting element). Therefore, a light-emitting element is provided, comprising: a first electrode; a second electrode opposing the first electrode; and an intermediate layer disposed between the first electrode and the second electrode and including a light-emitting layer. The light-emitting element comprises the organometallic compound represented by Chemical Formula 1 as described herein.

[0147] According to an implementation example,

[0148] The first electrode of the light-emitting element is an anode,

[0149] The second electrode of the light-emitting element is a cathode,

[0150] The intermediate layer further includes a hole transport region disposed between the first electrode and the light emitting layer and an electron transport region disposed between the light emitting layer and the second electrode.

[0151] The hole transport region includes a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron blocking layer or any combination thereof.

[0152] The electron transport region may include a buffer layer, a hole blocking layer, an electron regulating layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0153] According to an implementation example, at least one of the hole transport region and the light-emitting layer includes an aromatic amine compound, an acridine compound, a carbazole compound, or any combination thereof; or

[0154] At least one of the light-emitting layer and the electron transport region may include a silicon-containing compound, a phosphine oxide-containing compound, a sulfur oxide-containing compound, a phosphorus oxide-containing compound, a triazine-containing compound, a pyrimidine-containing compound, a pyridine-containing compound, a dibenzofuran-containing compound, a dibenzothiophene-containing compound, or any combination thereof.

[0155] According to another embodiment, the organometallic compound may be included between the first electrode and the second electrode of the light-emitting element. Thus, the organometallic compound may be included in an intermediate layer of the light-emitting element (e.g., a light-emitting layer of the intermediate layer). In addition, the light-emitting layer may emit phosphorescence or fluorescence emitted from the organometallic compound.

[0156] According to yet another implementation example, the light emitting element may include a cover layer arranged outside the first electrode or outside the second electrode.

[0157] For example, the light-emitting element may further include at least one of a first covering layer disposed outside the first electrode and a second covering layer disposed outside the second electrode, and the organometallic compound represented by Chemical Formula 1 may be included in at least one of the first covering layer and the second covering layer. For a more detailed description of the first covering layer and / or the second covering layer, reference is made to the description in this specification.

[0158] According to an implementation example, the light emitting element may include:

[0159] a first covering layer disposed on an outer side of the first electrode and comprising an organic metal compound represented by Chemical Formula 1;

[0160] a second covering layer disposed on an outer side of the second electrode and comprising the organometallic compound represented by the Chemical Formula 1; or

[0161] the first covering layer and the second covering layer.

[0162] In this specification, “(the intermediate layer and / or the covering layer) includes an organic metal compound” may be understood as “(the intermediate layer and / or the covering layer) may include one of the organic metal compounds belonging to the category of Chemical Formula 1 or two or more organic metal compounds different from each other belonging to the category of Chemical Formula 1”.

[0163] For example, the intermediate layer and / or the covering layer may include only the compound 1 as the organometallic compound. In this case, the compound 1 may be present in the light-emitting layer of the light-emitting element. In addition, the intermediate layer may include the compound 1 and the compound 2 as the organometallic compound. In this case, the compound 1 and the compound 2 may be present in the same layer (for example, both the compound 1 and the compound 2 may be present in the light-emitting layer) or in different layers (for example, the compound 1 may be present in the light-emitting layer, and the compound 2 may be present in the electron transport region).

[0164] The term "intermediate layer" in this specification refers to a single layer and / or a plurality of layers disposed between the first electrode and the second electrode in the light emitting element.

[0165] According to another aspect, an electronic device including the light-emitting element 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. Furthermore, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. For a more detailed description of the electronic device, please refer to the description in this specification.

[0166] [right Figure 1 [Note]

[0167] Figure 1 FIG2 is a cross-sectional view schematically showing a light emitting element 10 according to an embodiment of the present invention. The light emitting element 10 includes a first electrode 110 , an intermediate layer 130 , and a second electrode 150 .

[0168] Below, we will refer to Figure 1 The structure and manufacturing method of the light emitting element 10 according to the embodiment of the present invention are described below.

[0169] [First electrode 110]

[0170] The substrate may additionally be arranged on Figure 1 The lower portion of the first electrode 110 or the upper portion of the second electrode 150 is provided. As the substrate, a glass substrate or a plastic substrate can be used. Alternatively, the substrate can be a flexible substrate, for example, a plastic having excellent heat resistance and durability such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.

[0171] The first electrode 110 can be formed by depositing or sputtering a material on the substrate. If the first electrode 110 is an anode, a high work function material that can easily inject holes can be used as the material for the first electrode 110.

[0172] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. To form the first electrode 110 as a transmissive electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof may be used as a material for the first electrode 110. Alternatively, to form the first electrode 110 as a semi-transmissive 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 a material for the first electrode 110.

[0173] The first electrode 110 may have a single-layer structure consisting of a single layer or a multi-layer structure including a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.

[0174] [Middle layer 130]

[0175] The intermediate layer 130 is disposed on the first electrode 110. The intermediate layer 130 includes a light-emitting layer.

[0176] The 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 .

[0177] In addition to various organic substances, the intermediate layer 130 may further include metal-containing compounds such as organometallic compounds, inorganic substances such as quantum dots, and the like.

[0178] In addition, the intermediate layer 130 may include: i) two or more light-emitting units sequentially stacked between the first electrode 110 and the second electrode 150; and ii) a charge generation layer disposed between the two light-emitting units. When the intermediate layer 130 includes the light-emitting units and the charge generation layer as described above, the light-emitting element 10 may be a tandem light-emitting element.

[0179] [Hole Transport Region in Intermediate Layer 130]

[0180] The hole transport region may have the following structures: i) a single-layer structure consisting of a single layer composed of a single substance; ii) a single-layer structure consisting of a single layer containing a plurality of substances different from each other; or iii) a multilayer structure including a plurality of layers containing a plurality of substances different from each other.

[0181] The hole transport region may include a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron blocking layer, or any combination thereof.

[0182] For example, the hole transport region may have a multilayer structure of hole injection layer / hole transport layer, hole injection layer / hole transport layer / luminescence auxiliary layer, hole injection layer / luminescence auxiliary layer, hole transport layer / luminescence auxiliary layer or hole injection layer / hole transport layer / electron blocking layer stacked in sequence starting from the first electrode 110.

[0183] The hole transport region may include a compound represented by the following Chemical Formula 201, a compound represented by the following Chemical Formula 202, or any combination thereof:

[0184] <Chemical Formula 201>

[0185]

[0186] <Chemical Formula 202>

[0187]

[0188] In the chemical formula 201 and the chemical formula 202,

[0189] L 201 To L 204 Independently of each other, at least one R 10a Substituted or unsubstituted C3-C 60 A carbocyclic group or a group consisting of at least one R 10a Substituted or unsubstituted C1-C 60 Heterocyclic groups,

[0190] L 205 Can be *-O-*', *-S-*', *-N(Q 201 )-*', by at least one R 10a Substituted or unsubstituted C1-C 20 Alkylene, with at least one R 10a Substituted or unsubstituted C2-C 20 Alkenylene, with at least one R 10a Substituted or unsubstituted C3-C60 A carbocyclic group or a group consisting of at least one R 10a Substituted or unsubstituted C1-C 60 Heterocyclic groups,

[0191] xa1 to xa4 are independently one of integers from 0 to 5,

[0192] xa5 is an integer from 1 to 10,

[0193] R 201 to R 204 and Q 201 Independently of each other, at least one R 10a Substituted or unsubstituted C3-C 60 A carbocyclic group or a group consisting of at least one R 10a Substituted or unsubstituted C1-C 60 Heterocyclic groups,

[0194] R 201 and R 202 can be optionally connected via a single bond, by at least one R 10a Substituted or unsubstituted C1-C5 alkylene or at least one R 10a The substituted or unsubstituted C2-C5 alkenylene groups are linked to each other to form a 10a Substituted or unsubstituted C8-C 60 Polycyclic groups (e.g., carbazole groups, etc.) (e.g., refer to the following compound HT16, etc.),

[0195] R 203 and R 204 can be optionally connected via a single bond, by at least one R 10a Substituted or unsubstituted C1-C5 alkylene or at least one R 10a The substituted or unsubstituted C2-C5 alkenylene groups are linked to each other to form a 10a Substituted or unsubstituted C8-C 60 polycyclic groups, and

[0196] na1 can be one of integers from 1 to 4.

[0197] For example, the chemical formula 201 and the chemical formula 202 may each include at least one of the groups represented by the following chemical formulas CY201 to CY217:

[0198]

[0199] In the chemical formulas CY201 to CY217, R10b and R 10c For the description of R 10a Description, and ring CY 201 To Ring CY 204 Can be C3-C independently of each other 20 Carbocyclic group or C1-C 20 heterocyclic group, at least one hydrogen in the chemical formula CY201 to the chemical formula CY217 may be replaced by R as described in this specification 10a Replaced or not replaced.

[0200] According to an embodiment, the ring CY in the chemical formula CY201 to the chemical formula CY217 201 To Ring CY 204 These may be, independently of one another, a phenyl group, a naphthalene group, a phenanthrene group or an anthracene group.

[0201] According to another embodiment, the chemical formula 201 and the chemical formula 202 may each include at least one of the groups represented by the chemical formulas CY201 to CY203.

[0202] According to yet another embodiment, the chemical formula 201 may include at least one of the groups represented by the chemical formulas CY201 to CY203 and at least one of the groups represented by the chemical formulas CY204 to CY217.

[0203] According to another implementation example, in the chemical formula 201, xa1 can be 1, R 201 It may be a group represented by one of the chemical formulas CY201 to CY203, xa2 may be 0, R 202 It may be a group represented by one of the chemical formulas CY204 to CY207.

[0204] According to another implementation example, each of the chemical formula 201 and the chemical formula 202 may not include the groups represented by the chemical formulas CY201 to CY203.

[0205] According to another implementation example, each of the chemical formula 201 and the chemical formula 202 may not include the groups represented by the chemical formulas CY201 to CY203, but may include at least one of the groups represented by the chemical formulas CY204 to CY217.

[0206] According to yet another example, each of the Chemical Formula 201 and the Chemical Formula 202 may not include the groups represented by the Chemical Formulas CY201 to CY217.

[0207] For example, the hole transport region may include one of the following compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA ...camphorsulfonic acid (PANI / CSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / camphorsulfonic acid (PANI / acid), polyaniline / poly(4-styrenesulfonate) (PANI / PSS: Polyaniline / Poly(4-styrenesulfonate)) or any combination thereof:

[0208]

[0209]

[0210]

[0211]

[0212]

[0213] The thickness of the hole transport region may be about to about (For example, about to about In the case where 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 to about (For example, about to about ), the thickness of the hole transport layer may be about to about (For example, about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer fall within the aforementioned ranges, satisfactory hole transport characteristics can be obtained without substantially increasing the driving voltage.

[0214] The luminescence-assisting layer increases light emission efficiency by compensating for the optical resonance distance caused by the wavelength of light emitted from the luminescent layer, and the electron-blocking layer prevents electrons from leaking from the luminescent layer to the hole-transporting region. The aforementioned substances that may be included in the hole-transporting region may be contained in both the luminescence-assisting layer and the electron-blocking layer.

[0215] [p-dopant]

[0216] In addition to the above substances, the hole transport region may include a charge generating substance for improving conductivity. The charge generating substance may be uniformly or non-uniformly dispersed (eg, in the form of a single layer consisting of the charge generating substance) within the hole transport region.

[0217] The charge generating substance may be, for example, a p-dopant.

[0218] For example, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be -3.5 eV or less.

[0219] According to an implementation example, the p-dopant may include a quinone derivative, a cyanide-containing compound, a compound containing element EL1 and element EL2, or any combination thereof.

[0220] Examples of the quinone derivative may include TCNQ, F4-TCNQ, and the like.

[0221] Examples of the cyano group-containing compound may include HAT-CN, a compound represented by the following Chemical Formula 221, and the like.

[0222]

[0223] <Chemical Formula 221>

[0224]

[0225] In the chemical formula 221,

[0226] R 221 to R 223 Independently of each other, at least one R 10a Substituted or unsubstituted C3-C 60 A carbocyclic group or a group consisting of at least one R 10a Substituted or unsubstituted C1-C 60Heterocyclic groups,

[0227] The R 221 to R 223 At least one of them may be independently a C3-C 60 Carbocyclic group or C1-C 60 Heterocyclic group: cyano; -F; -Cl; -Br; -I; C1-C ... 20 alkyl; or any combination thereof.

[0228] In the compound containing the element EL1 and the element EL2, the element EL1 may be a metal, a metalloid, or a combination thereof, and the element EL2 may be a non-metal, a metalloid, or a combination thereof.

[0229] Examples of the metal may include 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.); late transition metals (e.g., zinc (Zn), indium (In), tin (Sn), etc.); and lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.).

[0230] Examples of the metalloid may include silicon (Si), antimony (Sb), tellurium (Te), and the like.

[0231] Examples of the non-metal may include oxygen (O), halogen (eg, F, Cl, Br, I, etc.), and the like.

[0232] For example, the compound containing element EL1 and element EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, metalloid iodides, etc.), metal tellurides, or any combination thereof.

[0233] Examples of the metal oxides may include tungsten oxides (e.g., WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxides (e.g., VO, V2O3, VO2, V2O5, etc.), molybdenum oxides (MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), rhenium oxides (e.g., ReO3, etc.), etc.

[0234] Examples of the metal halide may include alkali metal halide, alkaline earth metal halide, transition metal halide, post-transition metal halide, lanthanide metal halide, and the like.

[0235] Examples of the alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, etc.

[0236] Examples of the alkaline earth metal halide may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, BaI2, etc.

[0237] Examples of the transition metal halide may 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, 3, TaBr3, TaI3, etc.), chromium halides (e.g., CrF3, CrCl3, CrBr3, CrI3, etc.), molybdenum halides (e.g., MoF3, MoCl3, MoBr3, MoI3, etc.), 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, etc.), r2, 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, Ir Br2, 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.), silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.) and gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.).

[0238] Examples of the late transition metal halide may include zinc halide (eg, ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halide (eg, InI3, etc.), tin halide (eg, SnI2, etc.).

[0239] Examples of the lanthanide metal halides may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, SmI3, etc.

[0240] Examples of the metalloid halide may include antimony halide (eg, SbCl 5 , etc.).

[0241] Examples of the metal tellurides may 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.), late transition metal tellurides (e.g., ZnTe, etc.), lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).

[0242] [Light-Emitting Layer in Intermediate Layer 130]

[0243] In the case where the light-emitting element 10 is a full-color light-emitting element, the light-emitting layer can be patterned into a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer according to independent sub-pixels. Alternatively, the light-emitting layer can have a structure in which two or more of the red light-emitting layer, the green light-emitting layer, and the blue light-emitting layer are stacked in contact or spaced apart, or a structure in which two or more of the red light-emitting substance, the green light-emitting substance, and the blue light-emitting substance are mixed without distinguishing between layers, thereby emitting white light.

[0244] The light emitting layer may include a host and a dopant. The dopant may include an organic metal compound represented by Chemical Formula 1.

[0245] The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.

[0246] The phosphorescent dopant may include an organometallic compound represented by the Chemical Formula 1.

[0247] The dopant may be included in an amount of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.

[0248] Furthermore, the light emitting layer may include quantum dots.

[0249] In addition, the light-emitting layer may include a delayed fluorescent substance. The delayed fluorescent substance may function as a host or a dopant in the light-emitting layer.

[0250] The thickness of the light-emitting layer can be about to about (For example, about to about When the thickness of the light-emitting layer satisfies the above range, excellent light-emitting characteristics can be exhibited without substantially increasing the driving voltage.

[0251] [main body]

[0252] The host may include a compound represented by the following Chemical Formula 301:

[0253] <Chemical Formula 301>

[0254] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 ,

[0255] In the chemical formula 301,

[0256] Ar 301 and L 301 Independently of each other, at least one R 10a Substituted or unsubstituted C3-C 60 A carbocyclic group or a group consisting of at least one R 10a Substituted or unsubstituted C1-C 60 Heterocyclic groups,

[0257] xb11 is 1, 2, or 3,

[0258] xb1 is an integer from 0 to 5,

[0259] R 301 is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, or is replaced by at least one R 10a Substituted or unsubstituted C1-C 60 Alkyl, with at least one R 10a Substituted or unsubstituted C2-C 60 Alkenyl, with at least one R 10aSubstituted or unsubstituted C2-C 60 Alkynyl, with at least one R 10a Substituted or unsubstituted C1-C 60 Alkoxy, with at least one R 10a Substituted or unsubstituted C3-C 60 Carbocyclic group, with at least one R 10a Substituted or unsubstituted C1-C 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 ),

[0260] xb21 is an integer from 1 to 5,

[0261] Q 301 To Q 303 For the description of Q1, please refer to the description of Q1 in this manual.

[0262] For example, when xb11 in the chemical formula 301 is 2 or more, two or more Ar 301 Can be connected to each other by a single bond.

[0263] 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:

[0264] <Chemical Formula 301-1>

[0265]

[0266] <Chemical Formula 301-2>

[0267]

[0268] In the Chemical Formula 301-1 and Chemical Formula 301-2,

[0269] Ring A 301 To Ring A 304 can be independently of each other by at least one R 10a Substituted or unsubstituted C3-C 60 A carbocyclic group or a group consisting of at least one R 10aSubstituted or unsubstituted C1-C 60 Heterocyclic groups,

[0270] X 301 O, S, N-[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),

[0271] xb22 and xb23 are independently 0, 1 or 2,

[0272] To L 301 , xb1 and R 301 Please refer to the description in this manual for details.

[0273] To L 302 To L 304 The descriptions of L are independent of each other. 301 Description,

[0274] The descriptions of xb2 to xb4 refer independently to the description of xb1.

[0275] R 302 to R 305 and R 311 to R 314 For the description of R 301 Description.

[0276] As another example, the host may include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. For example, the host may include a Be complex (e.g., compound H55 below), a Mg complex, a Zn complex, or any combination thereof.

[0277] As another example, the host may include one of the following compounds H1 to H124, 9,10-di(2-naphthyl)anthracene (ADN: 9,10-Di(2-naphthyl)anthracene), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN: 2-Methyl-9,10-bis(naphthalen-2-yl)anthracene), 9,10-di(2-naphthyl)-2-tert-butyl-anthracene (TBADN: 9,10-di-(2-naphthyl)anthracene), hyl)-2-t-butyl-anthracene), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP: 4,4'-bis(N-carbazolyl)-1,1'-biphenyl), 1,3-di-9-carbazolylbenzene (mCP: 1,3-di-9-carbazolylbenzene), 1,3,5-tri(carbazol-9-yl)benzene (TCP: 1,3,5-tri(carbazol-9-yl)benzene), or any combination thereof:

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284] [Phosphorescent dopant]

[0285] The phosphorescent dopant may include at least one transition metal as a central metal.

[0286] The phosphorescent dopant may include the organometallic compound represented by the Chemical Formula 1.

[0287] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.

[0288] The phosphorescent dopant may be electrically neutral.

[0289] For example, the phosphorescent dopant may include an organometallic compound represented by the following Chemical Formula 401:

[0290] <Chemical Formula 401>

[0291] M(L 401 ) xc1 (L 402 ) xc2

[0292] <Chemical Formula 402>

[0293]

[0294] In the chemical formula 401 and the chemical formula 402,

[0295] 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)),

[0296] L 401 is a ligand represented by the chemical formula 402, xc1 can be 1, 2 or 3, wherein when xc1 is 2 or more, two or more L 401 Same or different from each other,

[0297] L 402 is an organic ligand, xc2 is 0, 1, 2, 3 or 4. When xc2 is 2 or more, two or more L 402 Same or different from each other,

[0298] X 401 and X 402 independently of each other nitrogen or carbon,

[0299] Ring A 401 and Ring A 402 Independently of each other, C3-C 60 Carbocyclic group or C1-C 60 Heterocyclic groups,

[0300] 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=*',

[0301] X 403 and X 404 are independently chemical bonds (e.g., covalent bonds or coordination bonds), O, S, N (Q 413 )、B(Q 413)、P(Q 413 )、C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ),

[0302] Regarding the Q 411 To Q 414 For the description of Q1, please refer to the description of Q1 in this manual.

[0303] R 401 and R 402 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, 10a Substituted or unsubstituted C1-C 20 Alkyl, with at least one R 10a Substituted or unsubstituted C1-C 20 Alkoxy, with at least one R 10a Substituted or unsubstituted C3-C 60 Carbocyclic group, with at least one R 10a Substituted or unsubstituted C1-C 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 ),

[0304] Regarding the Q 401 To Q 403 For the description of Q1, please refer to the description of Q1 in this manual.

[0305] xc11 and xc12 are independently an integer from 0 to 10,

[0306] * and *' in the chemical formula 402 are binding sites for M in the chemical formula 401.

[0307] For example, in the chemical formula 402, i) X 401 It can be nitrogen, X 402 Can be carbon, or ii) X 401 and X 402 Both may be nitrogen.

[0308] As another example, when xc1 in the chemical formula 401 is 2 or more, two or more L 401 The two rings A 401 Optionally through T as a linker 402 Connected to each other, or two rings L 402 Selectively through T as a linker 403 are connected to each other (refer to the following compounds PD1 to PD4 and PD7). 402 and T 403 For the description of T 401 Description.

[0309] In the chemical formula 401, L 402 It can be any organic ligand. For example, the L 402 It may include a halogen group, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), -C(=O), an isonitrile group, a -CN group, a phosphorus group (e.g., a phosphine group or a phosphite group), or any combination thereof.

[0310] The phosphorescent dopant may include, for example, one of the following compounds PD1 to PD25 or any combination thereof:

[0311]

[0312] [Fluorescent dopant]

[0313] The fluorescent dopant may include an amine-containing compound, a styryl-containing compound, or any combination thereof.

[0314] For example, the fluorescent dopant may include a compound represented by the following Chemical Formula 501:

[0315] <Chemical Formula 501>

[0316]

[0317] In the chemical formula 501,

[0318] Ar 501 , L 501 To L 503 、R 501 and R 502 Independently of each other, at least one R 10a Substituted or unsubstituted C3-C 60 A carbocyclic group or a group consisting of at least one R 10a Substituted or unsubstituted C1-C 60 Heterocyclic groups,

[0319] xd1 to xd3 are independently 0, 1, 2 or 3, and

[0320] xd4 can be 1, 2, 3, 4, 5 or 6.

[0321] For example, Ar in the chemical formula 501 501 It may include a condensed ring group in which three or more monocyclic groups are condensed with each other (for example, anthracene group, group or pyrene group).

[0322] For example, xd4 in the chemical formula 501 may be 2.

[0323] For example, the fluorescent dopant may include: one of the following compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof:

[0324]

[0325]

[0326]

[0327] [Delayed fluorescent substance]

[0328] The light emitting layer may include a delayed fluorescent substance.

[0329] The delayed fluorescent substance in this specification can be selected from any compound that can emit delayed fluorescence based on a delayed fluorescence emission mechanism.

[0330] The delayed fluorescent substance included in the light emitting layer may function as a host or a dopant according to the types of other substances included in the light emitting layer.

[0331] According to one embodiment, the difference between the triplet energy level (eV) of the delayed fluorescent substance and the singlet energy level (eV) of the delayed fluorescent substance can be greater than 0 eV and less than 0.5 eV. By ensuring that the difference between the triplet energy level (eV) of the delayed fluorescent substance and the singlet energy level (eV) of the delayed fluorescent substance satisfies the above range, reverse energy transfer (up-conversion) from the triplet state to the singlet state in the delayed fluorescent substance can be effectively achieved, thereby improving the luminous efficiency of the light-emitting element 10.

[0332] For example, the delayed fluorescent material may include: i) at least one electron donor (eg, a π-electron-rich C3-C 60 Cyclic groups (πelectron-rich C3-C 60cyclic group) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group, a π-electron-poor nitrogen-containing C1-C 60 Cyclic group (πelectron-deficientnitrogen-containing C1-C 60 cyclic group) etc.); ii) C8-C ... 60 Substances with polycyclic groups, etc.

[0333] Examples of the delayed fluorescent substance may include at least one of the following compounds DF1 to DF9:

[0334]

[0335]

[0336] [Quantum dot]

[0337] The light emitting layer may include quantum dots.

[0338] The "quantum dot" in this specification refers to a crystal of a semiconductor compound, and may include any substance capable of emitting light of various emission wavelengths depending on the size of the crystal.

[0339] The diameter of the quantum dots may be, for example, about 1 nm to about 10 nm.

[0340] The quantum dots can be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or processes similar to these processes.

[0341] The wet chemical process is a method of growing quantum dot particle crystals by mixing an organic solvent and a precursor substance. As the crystals grow, the organic solvent acts as a dispersant that naturally coordinates to the surface of the quantum dot crystals and regulates their growth. Therefore, the growth of quantum dot particles can be controlled by utilizing a process that is easier and less expensive than vapor deposition processes such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).

[0342] The quantum dots may include 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, Group IV elements or compounds; or any combination thereof.

[0343] Examples of the II-VI semiconductor compounds may 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, Cd ZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, etc.; quaternary compounds such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, etc.; or any combination thereof.

[0344] Examples of the 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 GaNPs, GaNAs, GaNSb, GaPAs, GaPSb, AlNPs, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNPs, InAlP, InNAs, InNSb, InPAs, InPSb, etc.; quaternary compounds such as GaAlNPs, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNPs, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNPs, InAlNAs, InAlNSb, InAlPAs, InAlPSb, etc.; or any combination thereof. Furthermore, the III-V semiconductor compounds may further include Group II elements. Examples of Group III-V semiconductor compounds, which also include Group II elements, may include InZnP, InGaZnP, InAlZnP, and the like.

[0345] Examples of the III-VI semiconductor compounds may include: binary compounds such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, InTe, etc.; ternary compounds such as InGaS3, InGaSe3, etc.; or any combination thereof.

[0346] Examples of the I-III-VI group semiconductor compounds may include: ternary compounds such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, AgAlO2, etc.; or any combination thereof.

[0347] Examples of the 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.

[0348] The Group IV elements or compounds may include: single elements, such as Si, Ge, etc.; binary compounds, such as SiC, SiGe, etc.; or any combination thereof.

[0349] Each element included in the multi-component compound such as the binary compound, ternary compound, and quaternary compound may be present in the particle at a uniform concentration or a non-uniform concentration.

[0350] In addition, the quantum dots may have a single structure in which the concentration of each element included in the corresponding quantum dots is uniform, or a core-shell dual structure. For example, a substance included in the core and a substance included in the shell may be different from each other.

[0351] The shell of the quantum dot can function as a protective layer for preventing chemical denaturation of the core while maintaining semiconductor properties and / or as a charging layer for imparting electrophoretic properties to the quantum dot. The shell can be a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient in which the concentration of the element present in the shell gradually decreases toward the center.

[0352] Examples of the quantum dot shell may include metal, metalloid or non-metal oxides, semiconductor compounds, or combinations thereof. Examples of the metal, metalloid or non-metal 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 semiconductor compound may include II-VI semiconductor compounds, III-V semiconductor compounds, III-VI semiconductor compounds, I-III-VI semiconductor compounds, 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.

[0353] Quantum dots can have a full width at half maximum (FWHM) of an emission wavelength spectrum of approximately 45 nm or less (specifically, approximately 40 nm or less, and more specifically, approximately 30 nm or less). Within this range, color purity or color reproducibility can be improved. Furthermore, light emitted by such quantum dots is emitted in all directions, thereby improving a wide viewing angle.

[0354] Furthermore, the quantum dots may be in the form of spherical, pyramidal, multi-arm, or cubic nanoparticles, nanotubes, nanowires, nanofibers, nanoplates, and the like.

[0355] By adjusting the size of the quantum dots, the energy band gap can also be adjusted, thereby obtaining light of various wavelengths in the quantum dot light-emitting layer. Therefore, by utilizing quantum dots of varying sizes, a light-emitting element emitting light of various wavelengths can be realized. Specifically, the quantum dot size can be selected to emit red, green, and / or blue light. Furthermore, the quantum dot size can be configured to combine multiple colors of light to produce white light.

[0356] [Electron Transport Region in Intermediate Layer 130]

[0357] The electron transport region may have the following structures: i) a single-layer structure consisting of a single layer composed of a single substance; ii) a single-layer structure consisting of a single layer containing a plurality of substances different from each other; or iii) a multilayer structure including a plurality of layers containing a plurality of substances different from each other.

[0358] The electron transport region may include a buffer layer, a hole blocking layer, an electron regulating layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0359] For example, the electron transport region may have a structure of an electron transport layer / electron injection layer, a hole blocking layer / electron transport layer / electron injection layer, an electron regulating layer / electron transport layer / electron injection layer, or a buffer layer / electron transport layer / electron injection layer stacked in sequence starting from the light-emitting layer.

[0360] The electron transport region (e.g., a buffer layer, a hole blocking layer, an electron regulating layer, or an electron transport layer in the electron transport region) may include a nitrogen-containing C1-C 60 Cyclic groups (πelectron-deficient nitrogen-containing C1-C 60 cyclic group) metal-free compounds.

[0361] For example, the electron transport region may include a compound represented by the following Chemical Formula 601.

[0362] <Chemical Formula 601>

[0363] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21

[0364] In the chemical formula 601,

[0365] Ar 601 and L 601 Independently of each other, at least one R 10a Substituted or unsubstituted C3-C 60 A carbocyclic group or a group consisting of at least one R 10a Substituted or unsubstituted C1-C 60 Heterocyclic groups,

[0366] xe11 is 1, 2, or 3,

[0367] xe1 is 0, 1, 2, 3, 4, or 5,

[0368] R 601 To be at least one R 10a Substituted or unsubstituted C3-C 60 Carbocyclic group, with at least one R 10a Substituted or unsubstituted C1-C 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 ),

[0369] Regarding the Q 601 To Q 603 For the description of Q1, please refer to the description of Q1 in this manual.

[0370] xe21 is 1, 2, 3, 4 or 5,

[0371] The Ar 601 , L 601 and R 601 At least one of them can be independently of each other by at least one R 10a Substituted or unsubstituted π-electron-poor nitrogen-containing C1-C 60 Ring group.

[0372] For example, when xe11 in the chemical formula 601 is 2 or more, two or more Ar 601 Can be connected to each other by a single bond.

[0373] As another example, Ar in the chemical formula 601 601 The anthracene group may be substituted or unsubstituted.

[0374] As another example, the electron transport region may include a compound represented by the following Chemical Formula 601-1:

[0375] <Chemical Formula 601-1>

[0376]

[0377] In the chemical formula 601-1,

[0378] X 614 N or C(R 614 ), X 615 N or C(R 615 ), X 616N or C(R 616 ), X 614 To X 616 At least one of them is N,

[0379] To L 611 To L 613 For the description of L 601 Description.

[0380] For the description of xe611 to xe613, refer to the description of xe1.

[0381] R 611 to R 613 For the description of R 601 Description,

[0382] R 614 to R 616 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy, with at least one R 10a Substituted or unsubstituted C3-C 60 A carbocyclic group or a group consisting of at least one R 10a Substituted or unsubstituted C1-C 60 Heterocyclic group.

[0383] For example, xe1 and xe611 to xe613 in Chemical Formula 601 and Chemical Formula 601-1 may be 0, 1, or 2 independently of each other.

[0384] The electron transport region may include one of the following compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP: 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline), 4,7-diphenyl-1,10-phenanthroline (Bphen: 4,7-Diphenyl-1,10-phenanthroline), Alq3, BAlq, TAZ, NTAZ, or any combination thereof:

[0385]

[0386]

[0387]

[0388] The thickness of the electron transport region may be about to about For example, about to about In the case where the electron transport region includes a buffer layer, a hole blocking layer, an electron regulating layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron regulating layer may be independently about 100 Å. to about (For example, about to about ), the thickness of the electron transport layer can be about to about (For example, about to about When the thickness of the buffer layer, the hole blocking layer, the electron regulating layer, the electron transport layer and / or the electron transport region satisfies the aforementioned range, satisfactory electron transport characteristics can be obtained without substantially increasing the driving voltage.

[0389] In addition to the substances described above, the electron transport region (eg, the electron transport layer in the electron transport region) may further include a metal-containing substance.

[0390] The metal-containing substance can include an alkali metal complex, an alkaline earth metal complex or any combination thereof. The metal ion of the alkali metal complex can be Li ion, Na ion, K ion, Rb ion or Cs ion, and the metal ion of the alkaline earth metal complex can be Be ion, Mg ion, Ca ion, Sr ion or Ba ion. The ligand coordinated with the metal ion of the alkali metal complex and the alkaline earth metal complex can independently include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.

[0391] For example, the metal-containing substance may include a Li complex. The Li complex may include, for example, the following compound ET-D1 (LiQ) or compound ET-D2:

[0392]

[0393] The electron transport region may include an electron injection layer that easily injects electrons from the second electrode 150. The electron injection layer may directly contact the second electrode 150.

[0394] The electron injection layer may have the following structures: i) a single-layer structure consisting of a single layer composed of a single substance; ii) a single-layer structure consisting of a single layer containing multiple different substances; or iii) a multi-layer structure including multiple layers containing multiple different substances.

[0395] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0396] 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.

[0397] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may include oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, respectively, or any combination thereof.

[0398] The alkali metal 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 alkaline earth metal compound may include x Sr 1-x O (where x is a real number satisfying 0 < x < 1), Ba x Ca 1-xAlkaline earth metal compounds such as O (where x is a real number satisfying 0 < x < 1). The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. Alternatively, the rare earth metal-containing compound may include lanthanide metal tellurides. Examples of the lanthanide metal tellurides may include 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, Lu2Te3, etc.

[0399] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex may include: 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, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

[0400] The electron injection layer may be composed only of 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 as described above, or may further include an organic substance (for example, a compound represented by the chemical formula 601).

[0401] According to one implementation example, the electron injection layer may i) consist of an alkali metal-containing compound (for example, an alkali metal halide), or ii) be composed of a) an alkali metal-containing compound (for example, an alkali metal halide); and b) an alkali metal, alkaline earth metal, rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI:Yb co-deposited layer or a RbI:Yb co-deposited layer, etc.

[0402] In the case where the electron injection layer further includes an organic substance, 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 including the organic substance.

[0403] The thickness of the electron injection layer may be about to about about to about When the thickness of the electron injection layer satisfies the above range, satisfactory electron injection characteristics can be obtained without substantially increasing the driving voltage.

[0404] [Second electrode 150]

[0405] The second electrode 150 is disposed on the intermediate layer 130. The second electrode 150 may be a cathode serving as an electron injection electrode. A metal, alloy, conductive compound, or any combination thereof having a low work function may be used as a material for the second electrode 150.

[0406] 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 semi-transmissive electrode, or a reflective electrode.

[0407] The second electrode 150 may have a single-layer structure of a single layer or a multi-layer structure including a plurality of layers.

[0408] [Overlay]

[0409] The first covering layer may be arranged outside the first electrode 110, and / or the second covering layer may be arranged outside the second electrode 150. Specifically, the light-emitting element 10 may have: a structure in which the first covering layer, the first electrode 110, the intermediate layer 130, and the second electrode 150 are stacked in sequence; a structure in which the first electrode 110, the intermediate layer 130, the second electrode 150, and the second covering layer are stacked in sequence; or a structure in which the first covering layer, the first electrode 110, the intermediate layer 130, the second electrode 150, and the second covering layer are stacked in sequence.

[0410] Light generated by the light-emitting layer in the intermediate layer 130 of the light-emitting element 10 can be extracted toward the outside through the first electrode 110 as a semi-transmissive electrode or a transmissive electrode and the first covering layer, and light generated by the light-emitting layer in the intermediate layer 130 of the light-emitting element 10 can be extracted toward the outside through the second electrode 150 as a semi-transmissive electrode or a transmissive electrode and the second covering layer.

[0411] The first and second covering layers can increase the external luminous efficiency based on the principle of constructive interference, thereby increasing the light extraction efficiency of the light emitting element 10 and improving the luminous efficiency of the light emitting element 10 .

[0412] Each of the first cover layer and the second cover layer may include a substance having a refractive index (at 589 nm) of 1.6 or greater.

[0413] The first covering layer and the second covering layer may be independently an organic covering layer including organic matter, an inorganic covering layer including inorganic matter, or an organic-inorganic composite covering layer including organic matter and inorganic matter.

[0414] At least one of the first covering layer and the second covering layer may independently include a carbocyclic compound, a heterocyclic compound, an amino-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, heterocyclic compound, and amino-containing compound may be selectively substituted with a substituent containing O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. According to an implementation example, at least one of the first covering layer and the second covering layer may independently include an amino-containing compound.

[0415] For example, at least one of the first cover layer and the second cover layer may independently include the compound represented by Chemical Formula 201, the compound represented by Chemical Formula 202, or any combination thereof.

[0416] According to another implementation example, at least one of the first covering layer and the second covering layer may independently include one of the compounds HT28 to HT33, one of the following compounds CP1 to CP6, β-NPB, or any combination thereof:

[0417]

[0418] [film]

[0419] The organometallic compound represented by the chemical formula 1 can be included in various thin films. Therefore, according to another aspect, a thin film comprising the organometallic compound represented by the chemical formula 1 is provided. The thin film can be, for example, an optical component (or light control unit) (e.g., a color filter, a color conversion component, a cover layer, a light extraction efficiency improvement layer, a selective light absorption layer, a polarization layer, a quantum dot layer, etc.), a light shielding component (e.g., a light reflection layer, a light absorption layer, etc.), a protective component (e.g., an insulating layer, a dielectric layer, etc.), etc.

[0420] [Electronic devices]

[0421] The light emitting element 10 may be included in various electronic devices. For example, the electronic device including the light emitting element 10 may be a lighting device, an authentication device, or the like.

[0422] In addition to the light-emitting element 10, the electronic device (e.g., a light-emitting device) may further include: i) a color filter; ii) a color conversion layer; or iii) a color filter and a color conversion layer. The color filter and / or color conversion layer may be arranged in the direction of travel of at least one of the lights emitted from the light-emitting element 10. For example, the light emitted from the light-emitting element 10 may be blue light or white light. For the description of the light-emitting element 10, reference is made to the above description. According to one implementation example, the color conversion layer may include quantum dots. The quantum dots may be, for example, the same quantum dots as those described in this specification.

[0423] The electronic device may include a first substrate, the first substrate may include a plurality of sub-pixel regions, the color filter may include a plurality of color filter regions corresponding to the plurality of sub-pixel regions, and the color conversion layer may include a plurality of color conversion regions corresponding to the plurality of sub-pixel regions.

[0424] The pixel definition film is arranged between the plurality of sub-pixel regions to define each sub-pixel region.

[0425] The color filter may further include a plurality of color filter regions and a light-blocking pattern disposed between the plurality of color filter regions. 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.

[0426] The multiple color filter regions (or multiple color conversion regions) include: 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 multiple color filter regions (or multiple 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. For a description of quantum dots, refer to the description in this specification. Each of the first, second, and / or third regions may further include a scatterer.

[0427] For example, the light-emitting element may emit a first light, the first region may absorb the first light and emit a first-color light, the second region may absorb the first light and emit a second-color light, and the third region may absorb the first light and emit a third-color light. In this case, the first-color light, the second-color light, and the third-color light may have different maximum emission wavelengths. Specifically, the first light may be blue light, 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.

[0428] In addition to the light-emitting element 10 described above, the electronic device may further include a thin film transistor. The thin film transistor may include a source electrode, a drain electrode, and an active layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode 110 and the second electrode 150 of the light-emitting element 10.

[0429] The thin film transistor may further include a gate electrode, a gate insulating film, and the like.

[0430] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, or the like.

[0431] The electronic device may further include a sealing portion for sealing the light-emitting element 10. The sealing portion may be arranged between the color filter and / or color conversion layer and the light-emitting element 10. The sealing portion may allow light from the light-emitting element 10 to be extracted to the outside while preventing external air and moisture from penetrating into the light-emitting element 10. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one organic layer and / or inorganic layer. In the case where the sealing portion is a thin-film encapsulation layer, the electronic device may be flexible.

[0432] In addition to the color filter and / or color conversion layer, various functional layers may be additionally disposed on the sealing portion, depending on the intended use of the electronic device. Examples of such functional layers include a touch screen layer and a polarization layer. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The authentication device may, for example, be a biometric authentication device for authenticating an individual by utilizing biological information of a living being (e.g., a fingertip, pupil, etc.).

[0433] In addition to the light emitting element 10 as described above, the authentication device may further include a biometric information collector.

[0434] The electronic device can be applied to various displays, light sources, lighting, personal computers (for example, mobile personal computers), portable phones, digital cameras, electronic manuals, electronic dictionaries, electronic game consoles, medical instruments (for example, electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram display devices, ultrasonic diagnostic devices, endoscope display devices), fish finders, various measuring instruments, instruments (for example, instruments for vehicles, aircraft, and ships), projectors, etc.

[0435] [ Figure 2 and Figure 3 [Note]

[0436] Figure 2 is a cross-sectional view of a light emitting device according to an embodiment of the present invention.

[0437] Figure 2 The light-emitting device includes a substrate 100, a thin film transistor (TFT), a light-emitting element, and a packaging portion 300 that seals the light-emitting element.

[0438] 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 prevents impurities from penetrating through the substrate 100 and provides a flat surface on the substrate 100.

[0439] 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 .

[0440] The active layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and include a source region, a drain region, and a channel region.

[0441] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be disposed on the active layer 220 , and the gate electrode 240 may be disposed on the gate insulating film 230 .

[0442] An interlayer insulating film 250 may be disposed on 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, respectively, thereby insulating the gate electrode 240 from the source electrode 260 and the gate electrode 240 from the drain electrode 270.

[0443] The source electrode 260 and the 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 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 contact the exposed portions of the source region and the drain region of the active layer 220.

[0444] As described above, a thin film transistor (TFT) can be electrically connected to the light emitting element to drive the light emitting element and can be covered and protected by the passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. The light emitting element may be disposed on the passivation layer 280. The light emitting element includes a first electrode 110, an intermediate layer 130, and a second electrode 150.

[0445] The first electrode 110 may be disposed on the passivation layer 280 . The passivation layer 280 does not completely cover the drain electrode 270 but is disposed to expose a predetermined region of the drain electrode 270 . The first electrode 110 may be disposed to connect to the exposed portion of the drain electrode 270 .

[0446] A pixel defining film 290 including an insulator may be disposed on the first electrode 110. The pixel defining film 290 exposes a predetermined area of ​​the first electrode 110, and the intermediate layer 130 may be formed in the exposed area. The pixel defining film 290 may be a polyimide organic film or a polyacrylic organic film. Although not shown in FIG. Figure 2 However, at least a portion of the intermediate layer 130 may extend to the upper portion of the pixel defining film 290 and be arranged in the form of a common layer.

[0447] The second electrode 150 may be 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.

[0448] The encapsulation part 300 may be arranged on the cover layer 170. The encapsulation part 300 may be arranged on the light emitting element and play a role in protecting the light emitting element from moisture or oxygen. The encapsulation part 300 may include: an inorganic film including silicon nitride (SiNx ), silicon oxide (SiO x ), indium tin oxide, indium zinc oxide or a combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resin (for example, polymethyl methacrylate, polyacrylic acid, etc.), epoxy resin (for example, aliphatic glycidyl ether (AGE: aliphatic glycidyl ether)), etc.) or any combination thereof; or a combination of an inorganic film and an organic film.

[0449] Figure 3 is a cross-sectional view of a light emitting device according to another embodiment of the present invention.

[0450] In addition to the fact that the light-blocking pattern 500 and the functional region 400 are additionally arranged on the upper portion of the packaging portion 300, Figure 3 The light emitting device and Figure 2 The light emitting devices are the same light emitting devices. 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 an implementation example, Figure 3 The light-emitting elements of the light-emitting device may be series-connected light-emitting elements.

[0451] [Preparation method]

[0452] Each layer included in the hole transport region, the light-emitting layer, and each layer included in the electron transport region can be formed in a predetermined region by utilizing a variety of methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, laser thermal transfer (LITI) method, etc.

[0453] When each layer included in the hole transport region, the light emitting layer, and each layer included in the electron transport region are formed by vacuum deposition, the deposition temperature may be about 100° C. to about 500° C., about 10 -8 About 10 -3 Torr vacuum and about to about Within the deposition rate range of , the deposition conditions are selected in consideration of the material to be included in the layer to be formed and the structure of the layer to be formed.

[0454] [Definition of terms]

[0455] In this manual, C3-C 60A carbocyclic group is a ring group with 3 to 60 carbon atoms, which is composed only of carbon atoms. 60 The heterocyclic group refers to a ring group having 1 to 60 carbon atoms and including heteroatoms as ring atoms in addition to carbon. 60 Carbocyclic groups and C1-C 60 The heterocyclic group can be a monocyclic group consisting of one ring or a polycyclic group consisting of two or more rings condensed with each other. 60 The number of ring atoms in the heterocyclic group can be 3 to 61.

[0456] In this specification, the ring group includes the C3-C 60 Carbocyclic groups and C1-C 60 Both heterocyclic groups.

[0457] In this specification, the π-electron-rich C3-C 60 Cyclic groups (πelectron-rich C3-C 60 Cyclic group) refers to a cyclic group with 3 to 60 carbon atoms that does not include *-N=*' as a ring part, a nitrogen-containing C1-C 60 Cyclic groups (πelectron-deficient nitrogen-containing C1-C 60 The term "cyclic group" refers to a heterocyclic group having 1 to 60 carbon atoms and including *-N=*' as a ring-forming portion.

[0458] For example,

[0459] The C3-C 60 The carbocyclic group may be: i) a group T1 or ii) a condensed ring group in which two or more groups T1 are condensed with each other (for example, a cyclopentadiene group, an adamantane group, a norbornane group, a phenyl group, a pentalene group, a naphthalene group, an azulene group, an indacene group, an acenaphthene group, a phenanthren group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, group, perylene group, pentaphene group, heptalene group, tetracene group, phenene group, hexacenyl group, pentacene group, rubride group, coronene group, ovophenyl group, indene group, fluorene group, spirobifluorene group, benzofluorene group, indenophenanthrene group or indenoanthracene group),

[0460] The C1-C 60The heterocyclic group may be: i) a group T2; ii) a condensed ring group in which two or more groups T2 are condensed with each other; or iii) a condensed ring group in which one or more groups T2 and one or more groups T1 are condensed with each other (for example, a pyrrole group, a thiophene group, a furan group, an indole group, a benzindole group, a naphthoindole group, an isoindole group, a benzisoindole group, a naphthoisoindole group, a benzothiorrole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzothiorrole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofuranocarbazole group, a benzothiophenocarbazole group, a benzothiorrolecarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthothiorrole group, a benzofuranodibenzofuran group, a benzofuranodibenzothiophene group). group, benzothienodibenzothiophene group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzo quinoline group, benzoisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazoline group, benzoquinazoline group, phenanthroline group, cinnoline group, phthalazine group, naphthyridine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzothiophene group, azadibenzofuran group, etc.),

[0461] The π-electron-rich C3-C 60 The ring group can be: i) a group T1; ii) a condensed ring group in which two or more groups T1 are condensed with each other; iii) a group T3; iv) a condensed ring group in which two or more groups T3 are condensed with each other; or v) a condensed ring group in which one or more groups T3 and one or more groups T1 are condensed with each other (for example, the C3-C 60carbocyclic group, 1H-pyrrole group, thiole group, borole group, 2H-pyrrole group, 3H-pyrrole group, thiophene group, furan group, indole group, benzindole group, naphthoindole group, isoindole group, benzisoindole group, naphthoisoindole group, benzothiole group, benzothiophene group, benzofuran group, carbazole group, dibenzothiole group, dibenzothiophene group, dibenzofuran group, indenocarbazole group, indolecarbazole group, benzofuranocarbazole group, benzothienocarbazole group, benzothiorrolocarbazole group, benzoindolecarbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthothiophene group, benzonaphthothiorrole group, benzofuranodibenzofuran group, benzofuranodibenzothiophene group, benzothienodibenzothiophene group, etc.),

[0462] The π-electron-poor nitrogen-containing C1-C 60 The cyclic group may be: i) a group T4; ii) a condensed ring group in which two or more groups T4 are condensed with each other; iii) a condensed ring group in which one or more groups T4 and one or more groups T1 are condensed with each other; iv) a condensed ring group in which one or more groups T4 and one or more groups T3 are condensed with each other; or v) a condensed ring group in which one or more groups T4, one or more groups T1 and one or more groups T3 are condensed with each other (for example, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, benzoxazole group, benzisoxazole group, benzothiazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazoline group, benzoquinazoline group, phenanthroline group, cinnoline group, phthalazine group, naphthyridine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzothiophene group, azadibenzofuran group, etc.),

[0463] The group T1 can be 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, a norbornane (or bicyclo[2.2.1]heptane) group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group or a phenyl group,

[0464] The group T2 can be a furan group, a thiophene group, a 1H-pyrrole group, a thiol 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 isothiazole group, a thiadiazole group, an azathiol group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidinyl group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group or a dihydropyridazine group,

[0465] The group T3 may be a furan group, a thiophene group, a 1H-pyrrole group, a thiol group or a borole group, and

[0466] The group T4 can be 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 isothiazole group, a thiadiazole group, an azathiazole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group or a tetrazine group.

[0467] In this specification, the terms cyclic group, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic, π-electron-rich C3-C 60 Cyclic groups or π-electron-poor nitrogen-containing C1-C 60A cyclic group refers to a group condensed with any cyclic group according to the structure of the chemical formula in which the term is used, and may be a monovalent group or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.). For example, a "phenyl group" may be a benzo group, a phenyl group, a phenylene group, etc., which can be easily understood by those skilled in the art based on the structure of the chemical formula including the "phenyl group".

[0468] For example, the unit price is C3-C 60 Carbocyclic groups and monovalent C1-C 60 Examples of heterocyclic groups may include C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group; divalent C3-C 60 Carbocyclic groups and divalent C1-C 60 Examples of heterocyclic groups may include C3-C 10 Cycloalkylene, C1-C 10 Heterocycloalkylene, C3-C 10 Cycloalkenylene, C1-C 10 Heterocycloalkenylene, C6-C 60 Arylene, C1-C 60 heteroarylene groups, divalent non-aromatic condensed polycyclic groups, and divalent non-aromatic condensed heteropolycyclic groups.

[0469] In this manual, C1-C 60 The alkyl group refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, tert-decyl, and the like. In this specification, the C1-C 60 Alkylene refers to a group having a C1-C 60 Alkyl is a divalent group of the same structure.

[0470] In this manual, C2-C 60 Alkenyl refers to a C2-C 60The alkyl group is a monovalent hydrocarbon group containing one or more carbon-carbon double bonds in the middle or at the end, and specific examples thereof include vinyl, propenyl, butenyl, etc. 60 Alkenylene refers to a C2-C 60 Alkenyl is a divalent group of the same structure.

[0471] In this manual, C2-C 60 Alkynyl refers to a C2-C 60 The alkyl group contains one or more carbon-carbon triple bonds in the middle or at the end, and specific examples thereof include ethynyl, propynyl, etc. 60 Alkyne refers to a C2-C 60 Alkynyl is a divalent group of the same structure.

[0472] In this manual, C1-C 60 Alkoxy refers to a group having -OA 101 (Among them, A 101 is the C1-C 60 Specific examples thereof include methoxy, ethoxy, isopropoxy and the like.

[0473] In this manual, C3-C 10 Cycloalkyl refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornanyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, and the like. In this specification, C3-C 10 Cycloalkylene refers to a group having a C3-C 10 Cycloalkyl is a divalent group of the same structure.

[0474] In this manual, C1-C 10 Heterocycloalkyl refers to a monovalent ring group having 1 to 10 carbon atoms and including at least one heteroatom as a ring atom in addition to carbon atoms, and specific examples thereof include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl, tetrahydrothienyl, etc. In this specification, C1-C 10 Heterocycloalkylene refers to a group having a C1-C 10 Heterocycloalkyl is a divalent group of the same structure.

[0475] In this manual, C3-C 10 Cycloalkenyl refers to a monovalent ring group having 3 to 10 carbon atoms, which means a group having at least one carbon-carbon double bond in the ring but not having aromaticity, and specific examples thereof include cyclopentenyl, cyclohexenyl, cycloheptenyl, etc. In this specification, C3-C 10 Cycloalkenylene refers to the C3-C 10 The cycloalkenyl group is a divalent group having the same structure.

[0476] In this manual, C1-C 10 The heterocycloalkenyl group refers to a monovalent ring group having 1 to 10 carbon atoms and including at least one heteroatom as a ring atom in addition to carbon atoms, and having at least one double bond in the ring. 10 Specific examples of the heterocycloalkenyl group include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, 2,3-dihydrothienyl, and the like. 10 Heterocycloalkenylene refers to a group having a C1-C 10 Heterocycloalkenyl is a divalent group of the same structure.

[0477] In this manual, C6-C 60 Aryl refers to a monovalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms. 60 Arylene refers to a divalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms. 60 Specific examples of the aryl group include phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentyl, heptaphenyl, tetraphenyl, peryl, hexyl, pentyl, rubidinyl, coronenyl and ovalbenzene etc. 60 Aryl and C6-C 60 In the case where the arylene group includes two or more rings, the two or more rings may be condensed with each other.

[0478] In this manual, C1-C 60 The heteroaryl group refers to a monovalent group having a heterocyclic aromatic system with 1 to 60 carbon atoms, which includes at least one heteroatom as a ring atom in addition to carbon atoms. 60 The heteroarylene group represents a divalent group having a heterocyclic aromatic system with 1 to 60 carbon atoms and including at least one heteroatom as a ring atom in addition to carbon atoms. 60Specific examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, and the like. 60 Heteroaryl and C1-C 60 When the heteroarylene group includes two or more rings, the two or more rings may be condensed with each other.

[0479] In this specification, a monovalent non-aromatic condensed polycyclic group refers to a monovalent group in which two or more rings are condensed with each other, and the ring atoms only include carbon atoms, and the entire molecule has non-aromaticity (for example, a carbon atom number of 8 to 60). Specific examples of the monovalent non-aromatic condensed polycyclic group include indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl, indenoanthryl, etc. The divalent non-aromatic condensed polycyclic group in this specification refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

[0480] In this specification, a monovalent non-aromatic condensed heteropolycyclic group refers to a monovalent group in which two or more rings are condensed with each other, and at least one heteroatom is included as a ring-constituting atom in addition to carbon atoms, and the entire molecule has non-aromatic properties (for example, having 1 to 60 carbon atoms). Specific examples of the monovalent non-aromatic condensed heteropolycyclic group include pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiorolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiorolyl, dibenzothiophenyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzothiorolyl, azadibenzothiophenyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazole ... The divalent non-aromatic condensed heteropolycyclic group in this specification refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

[0481] In this manual, C6-C 60 Aryloxy refers to -OA 102 (Among them, A 102 It is the C6-C 60 Aryl), the C6-C 60 Arylthio refers to -SA 103 (Among them, A 103 It is the C6-C 60 aryl).

[0482] In this manual, “C7-C 60 " refers to -A 104 A 105 (Among them, A 104 It is C1-C 54 Alkylene, A 104 It is C6-C 59 Aryl), in this specification C2-C 60 Heteroaralkyl refers to -A 106 A 107 (Among them, A106 It is C1-C 59 Alkylene, A 107 It is C1-C 59 heteroaryl).

[0483] In this manual, “R 10a ” can be:

[0484] Deutrium (-D), -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0485] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -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 any combination thereof, substituted or unsubstituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 alkoxy;

[0486] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q22 )、-B(Q 21 )(Q 22 ),-C(=O)(Q 21 )、-S(=O)2(Q 21 ),-P(=O)(Q 21 )(Q 22 ) or any combination thereof substituted or unsubstituted C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 heteroarylalkyl; or

[0487] -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 ),

[0488] The Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 independently of one another: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 Alkoxy; or deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted or unsubstituted C3-C 60 Carbocyclic group or C1-C 60 Heterocyclic group; C7-C 60 Aralkyl or C2-C 60 Heteroaralkyl.

[0489] In this specification, a heteroatom refers to any atom other than a carbon atom. Examples of the heteroatom include O, S, N, P, Si, B, Ge, Se, or any combination thereof.

[0490] The third-row transition metals in this specification include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), and gold (Au).

[0491] In this specification, "Ph" refers to phenyl, "Me" refers to methyl, "Et" refers to ethyl, "tert-Bu" or "Bu" refers to ethyl. t ” refers to tert-butyl, and “OMe” refers to methoxy.

[0492] In this specification, "biphenyl" refers to "phenyl substituted by phenyl". The "biphenyl" belongs to a group whose substituent is "C6-C 60 "substituted phenyl" or "aryl".

[0493] The term "terphenyl" in this specification refers to a phenyl group substituted with a biphenyl group. 60 Aryl-substituted C6-C 60 "substituted phenyl" or "aryl".

[0494] In the present specification, unless otherwise defined, "* to *" means a binding site with adjacent atoms in the corresponding chemical formula or moiety.

[0495] Hereinafter, the compounds and light-emitting elements of one embodiment of the present invention will be described in more detail through synthesis examples and examples. In the following synthesis examples, when "A is replaced by B", the molar equivalents of A and B are the same.

[0496] [Example]

[0497] Synthesis Example 1: Synthesis of Compound 2

[0498]

[0499] (1) Synthesis of intermediate [2-1]

[0500] 10 g (63.3 mmol) of 2-bromo-4-hydroxypyridine, 9.0 g (57.5 mmol) of (4-hydroxypyridin-2-yl)boronic acid, 270 mg (1.2 mmol) of palladium acetate, 630 mg (2.4 mmol) of triphenylphosphine, and 15.9 g (115 mmol) of potassium carbonate were added to a reaction vessel and suspended in 430 mL of 1,4-dioxane and 150 mL of water. The reaction temperature was raised to 110°C, and the solution was stirred for 12 hours. After the reaction was completed, the reactant was cooled to room temperature and extracted with ethyl acetate. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The dried product was separated by column chromatography to obtain 9.3 g (49 mmol) of intermediate [2-1].

[0501] (2) Synthesis of intermediate [2-2]

[0502] 10.5 g (31 mmol) of the intermediate [2-1], 10.1 g (37 mmol) of 1,3-dibromobenzene, 13.2 g (62 mmol) of tripotassium phosphate, 590 mg (3.1 mmol) of copper iodide, and 380 mg (3.1 mmol) of picolinic acid were added to a reaction vessel and suspended in 310 mL of dimethyl sulfoxide. The mixture was heated and stirred at 160°C for 12 hours. After the reaction was terminated, the reactant was cooled to room temperature and extracted with ethyl acetate. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The dried product was separated by column chromatography to obtain 10.6 g (20 mmol) of the intermediate [2-2].

[0503] (3) Synthesis of intermediate [2-3]

[0504] A reactor was charged with 12.8 g (26 mmol) of the intermediate [2-2], 11.4 g (34 mmol) of N1-([1,1':3',1"-terphenyl]-2'-yl)benzene-1,2-diamine, 460 mg (0.5 mmol) of tris(dibenzylideneacetone)dipalladium, 480 mg (1.0 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (Xphos), and 5.0 g (52 mmol) of sodium tert-butoxide, which were suspended in 260 mL of toluene. The reaction temperature was raised to 110°C, and the solution was stirred for 6 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The extracted organic layer was washed with saturated sodium chloride aqueous solution and dried over sodium sulfate. The dried product was separated by column chromatography to obtain 14.2 g (19 mmol) of intermediate [2-3].

[0505] (4) Synthesis of intermediate [2-4]

[0506] 14.2 g (19 mmol) of the intermediate [2-3], 140 mL (950 mmol) of triethyl orthoformate, and 10.9 g (105 mmol) of a 35 wt% HCl solution were added to a reaction vessel, heated, and stirred at 80°C for 12 hours. After the reaction, the reactants were cooled to room temperature, and the residual solvent was removed by column chromatography to obtain 11.1 g (14 mmol) of the intermediate [2-4].

[0507] (5) Synthesis of intermediate [2-5]

[0508] 11.1 g (14 mmol) of the intermediate [2-4] and 4.6 g (28 mmol) of ammonium hexafluorophosphate were added to a reaction vessel and suspended in a 2:1 methanol / water solution. The reaction mixture was stirred at room temperature for 12 hours. The resulting solid was filtered and separated by column chromatography to obtain 9.9 g (11 mmol) of the intermediate [2-5].

[0509] (6) Synthesis of Compound 2

[0510] 9.9 g (11 mmol) of the intermediate [2-5], 4.5 g (12.1 mmol) of dichloro (1,5-cyclooctadiene) platinum and 1.8 g (22 mmol) of sodium acetate were suspended in 220 ml of dioxane. The reaction mixture was heated and stirred at 110 ° C for 72 hours. After the reaction was completed, it was cooled to room temperature and extracted with ethyl acetate. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried with sodium sulfate. The dried product was separated using column chromatography to obtain compound 2 (2.7 g, 2.8 mmol).

[0511] Synthesis Example 2: Synthesis of Compound 33

[0512]

[0513] In the synthesis of intermediate [2-2] in Synthesis Example 1, compound 33 (0.6 g, 0.9 mmol) was synthesized by the same method as Synthesis Example 1 except that 3,5-dibromopyridine was used instead of 1,3-dibromobenzene.

[0514] The compound synthesized in the above synthesis example 1 H NMR and MS / FAB are shown in Table 1 below.

[0515] In addition to the compounds shown in Table 1, those skilled in the art can also easily know the synthesis methods of other compounds by referring to the above synthesis process and raw materials.

[0516] [Table 1]

[0517]

[0518] In addition to the compounds synthesized in Synthesis Example 1 and Synthesis Example 2, those skilled in the art can also easily know the synthesis methods of other compounds by referring to the above synthesis process and raw materials.

[0519] Example 1

[0520] As the anode, a 15Ω / cm 2 An ITO glass substrate (Corning) was cut into a size of 50 mm × 50 mm × 0.7 mm, ultrasonically cleaned with isopropyl alcohol and pure water for 5 minutes each, irradiated with ultraviolet light for 30 minutes, cleaned by exposure to ozone, and placed in a vacuum deposition apparatus.

[0521] 2-TNATA was vacuum deposited on the anode to form a layer with a thickness of A hole injection layer having a thickness of 100 nm was formed on the hole injection layer by vacuum deposition of 4,4'-bis[N-(1-naphthyl)-N-phenylaminobiphenyl (hereinafter referred to as NPB). hole transport layer.

[0522] A layer with a thickness of 100 nm was formed on the hole transport layer by vacuum depositing mCBP (host) and compound 2 (dopant) at a weight ratio of 9:1. luminescent layer.

[0523] Compound TSPO1 is vacuum deposited on the light emitting layer to form a layer with a thickness of A hole blocking layer is formed by vacuum depositing Alq3 on the hole blocking layer to a thickness of The electron transport layer is formed by vacuum depositing LiF on the electron transport layer. The electron injection layer is then formed by vacuum deposition of Al to a thickness of cathode, thereby manufacturing a light-emitting element.

[0524]

[0525] Examples 2 to 6 and Comparative Examples 1 to 3

[0526] A light-emitting element was produced by the same method as in Example 1, except that the compounds listed in Table 2 were used instead of Compound 2 in forming the light-emitting layer.

[0527] Evaluation Example 1

[0528] The luminance of the light emitting elements manufactured in Examples 1 to 6 and Comparative Examples 1 to 3 was measured at 1000 cd / m by using Keithley MU 236 and luminance meter PR650. 2 The driving voltage (V), current density (mA / cm 2 ), brightness (cd / m 2 ), luminous efficiency (cd / A) and maximum luminous wavelength (nm), and the results are presented in Table 2 respectively.

[0529] [Table 2]

[0530]

[0531]

[0532] From Table 2, it can be confirmed that the light-emitting elements of Examples 1 to 6 emit deep blue light and have low driving voltage, excellent brightness and luminous efficiency.

Claims

1. An organometallic compound, the organometallic compound being represented by the following chemical formula 1: <Chemical Formula 1> In the chemical formula 1, M 11 and M 12 For platinum, X 11 、X 12 、X 131 、X 142 、X 15 and X 16 C, X 132 and X 141 For N, L 11 , L 13 , L 15 is a single bond, L 12 and L 14 are independently *-S-*', *-Se-*' or *-O-*', wherein * and *' are binding sites with adjacent atoms, a11 to a15 are 1, R 11 to R 16 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro or C1-C 20 alkyl, b11 to b16 are independently one of integers from 0 to 5, In the chemical formula 1, The group represented by chemical formula A11-10: In the chemical formula A11-10, R 11a is deuterium or C1-C 20 alkyl, and R 11d is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro or C1-C 20 alkyl, b114 is an integer from 0 to 4, *For M 11 The binding site of L 11 The binding site, In the chemical formula 1, The group represented is selected from the following Chemical Formulas A12-1 to A12-4: In the Chemical Formulas A12-1 to A12-4, R 12a 、R 12b and R 12c are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro or C1-C 20 alkyl, *For M 11 The binding site of L 11 The binding site of L 12 The binding site, In the chemical formula 1, The group represented by chemical formula A13-2: In the chemical formula A13-2, R 13a and R 13b are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro or C1-C 20 alkyl, *1 is the same as M 11 The binding sites between M 12 The binding sites between 12 The binding site between the two, and *' is the binding site between 13 The binding sites between In the chemical formula 1, The group represented by chemical formula A14-2: In the chemical formula A14-2, R 14a and R 14b are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro or C1-C 20 alkyl, *1 is the same as M 11 The binding site of M 12 The binding site of L 13 The binding site of L 14 The binding site, In the chemical formula 1, The group represented is selected from the following Chemical Formulas A15-1 to A15-4: In the Chemical Formulas A15-1 to A15-4, R 15a to R 15c are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro or C1-C 20 alkyl, *For M 12 The binding site of L 14 The binding site of L 15 The binding site, In the chemical formula 1, The group represented by chemical formula A16-10: In the chemical formula A16-10, R 16a is deuterium or C1-C 20 alkyl, and R 16d is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro or C1-C 20 alkyl, b164 is an integer from 0 to 4, *For M 12 The binding site of L 15 binding site.

2. The organometallic compound according to claim 1, wherein The X 11 With M 11 The key between 16 With M 12 The bond between them is a coordination bond.

3. The organometallic compound according to claim 1, wherein The X 131 With M 11 The bond between them is a covalent bond. The X 132 With M 12 The bond between them is a coordination bond.

4. The organometallic compound according to claim 1, wherein The organometallic compound is selected from the following compounds:

5. A light-emitting element, comprising: a first electrode; a second electrode, facing the first electrode; as well as An intermediate layer is disposed between the first electrode and the second electrode and includes a light-emitting layer, and contains the organometallic compound according to any one of claims 1 to 4.

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