Organometallic compounds, light-emitting elements containing the same, and electronic devices including the light-emitting element.

Abstract

The present invention provides an organometallic compound, a light-emitting element containing the same, and an electronic device including the light-emitting element. [Solution] An organometallic compound represented by the following chemical formula 1, a light-emitting element containing the organometallic compound, and an electronic device containing the light-emitting element: TIFF2026090230000075.tif120169

Description

[Technical Field]

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

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

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

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

[0005] In one aspect, an organometallic compound represented by the following chemical formula 1 is provided:

[0006] [ka] In the aforementioned chemical formula 1, M is either Pt or Pd. X1 is C, X2 to X4 are, independently of each other, C or N, Ring CY2, Ring CY 31 , Ring CY 32 and Ring CY4 are, independently of each other, a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group, X 11 is N or C(R 11 ), X 12 is N or C(R 12 ), X 13 is N or C(R 13 ), X 51 is N or C(R 51 ), X 52 is N or C(R 52 ), X 53 is N or C(R 53 ), X 54 is N or C(R 54 ), X 61 is N or C(R 61 ), X 62 is N or C(R 62 ), X 63 is N or C(R 63 ), X 64 is N or C(R 64 ), X 71 is N or C(R 71 ), X 72 is N or C(R 72 ), X 73 is N or C(R 73 ), X 74 is N or C(R 74 ), L1 is O, S, Se, N(R 101 ), C(R 101 )(R 102 ), or Si(R 101 )(R 102 ), L2, L3, and L4 are, independently of each other, a single bond, O, S, Se, N(R'), C(R')(R”), or Si(R')(R”). At least one of L2, L3, and L4 is independently O, S, Se, N(R'), C(R')(R”), or Si(R')(R”). i) If L2 is N(R'), then R' is X 54 and X 61 ii) If L3 is N(R'), then R' is X 64 and X 71 iii) If L4 is N(R'), then R' is X 74 and X 11 They are not connected to each of them, R 11 ~R 13 R2, R3, R4, R 51 ~R 54 , R 61 ~R 64 , R 71 ~R 74 , R 101 , R 102 R' and R'' are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl alkyl groups, substituted or unsubstituted C2-C 60 Alkenyl group, substituted or unsubstituted C2-C 60 Alkynyl group, substituted or unsubstituted C1-C 60 Alkoxy group, substituted or unsubstituted C1-C 60 Alkylthio group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C1-C 10 Heterocycloalkenyl group, substituted or unsubstituted C6-C 60an aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic hetero-condensed polycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), or -P(=O)(Q8)(Q9), and a2 to a4 are, independently of one another, integers from 0 to 20, i) two or more of R 11 ~R 13 ; ii) two or more of the plurality of R2; iii) two or more of the plurality of R3; iv) two or more of the plurality of R4; v) two or more of R 51 ~R 54 ; vi) two or more of R 61 ~R 64 ; vii) two or more of R 71 ~R 74 ; viii) two or more of R 101 and R 102 , and ix) each of R’ and R” can optionally be linked to one another and form a C5-C 10a carbocyclic group substituted or unsubstituted with at least one R 30 , or a C1-C 10a heterocyclic group substituted or unsubstituted with at least one R 30 ; the description regarding the said R 10a is the same as the description regarding the said R 11 ; the substituted C1-C 60 alkyl group, the substituted C2-C 60 alkenyl group, the substituted C2-C 60 alkynyl group, the substituted C1-C 60 alkoxy group, the substituted C1-C 60 alkylthio group, the substituted C3-C 10 cycloalkyl group, the substituted C1-C 10 heterocycloalkyl group, the substituted C3-C 10Cycloalkenyl group, substituted C1-C 10 Heterocycloalkenyl group, substituted C6-C 60 Aryl group, substituted C6-C 60 Aryloxy group, substituted C6-C 60 Arylthio group, substituted C1-C 60 The substituents of the heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic hetero-condensed polycyclic group are Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, or C1-C 60 Alkylthio group; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic hetero-condensed polycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-Ge(Q 13 )(Q 14 )(Q 15), -B(Q 16 )(Q 17 ), -P(=O)(Q 18 )(Q 19 ), or any combination thereof, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, or C1-C 60 Alkylthio group; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C1-C 60 Alkylthio group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q 21 )(Q 22 ), -Si(Q 23 )(Q 24 )(Q 25 ), -Ge(Q 23 )(Q 24 )(Q 25 ), -B(Q 26 )(Q 27 ), -P(=O)(Q 28 )(Q 29 ), or any combination thereof, C3-C 10 Cycloalkyl groups, C1-C10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, or monovalent non-aromatic heterocondensed polycyclic groups; -N(Q 31 )(Q 32 ), -Si(Q 33 )(Q 34 )(Q 35 ), -Ge(Q 33 )(Q 34 )(Q 35 ), -B(Q 36 )(Q 37 ), or -P(=O)(Q 38 )(Q 39 );or Any combination of those; The above Q1 to Q9, Q 11 ~Q 19 Q 21 ~Q 29 and Q 31 ~Q 39 They are independent of each other, Hydrogen, deuterium, or -F; or Deuterium, -F, cyano group, C1-C 60 Alkyl alkyl group, C6-C 60 A C1-C group that is substituted or unsubstituted with an aryl group, or any combination thereof. 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C1-C 60 Alkylthio group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60Aryloxy group, C6-C 60 Arylthio group, C1-C 60 It is a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic heterocondensed polycyclic group.

[0007] In other aspects, a light-emitting element is provided, comprising a first electrode, a second electrode, and an intermediate layer disposed between the first electrode and the second electrode, the intermediate layer comprising one or more organometallic compounds.

[0008] In another aspect, an electronic device including the light-emitting element is provided. [Effects of the Invention]

[0009] The organometallic compound has excellent thermal stability and electrical properties, and can emit blue light with high color purity and / or a relatively narrow FWHM. An electronic device employing the organometallic compound, such as a light-emitting element, can emit high-color-purity blue light while exhibiting improved driving voltage and improved external quantum efficiency. High-quality electronic devices can be fabricated using such a light-emitting element. [Brief explanation of the drawing]

[0010] [Figure 1] This is a schematic cross-sectional view showing an organic light-emitting element according to one embodiment. [Modes for carrying out the invention]

[0011] The aforementioned organometallic compound is represented by the following chemical formula 1:

[0012] [ka] In the above chemical formula 1, M is either Pt or Pd.

[0013] For example, M is Pt.

[0014] In the above chemical formula 1, X1 is carbon (C), and X2 to X4 are independently carbon (C) or nitrogen (N).

[0015] According to one embodiment, X2 and X3 are each C, and X4 is N.

[0016] In other embodiments, the bonds between X1 and M and between X4 and M are coordinate bonds, while the bonds between X2 and M and between X3 and M are covalent bonds. That is, the organometallic compound is neutral.

[0017] Chemical formula 1, where X1 is represented as a carbene and X4 is nitrogen, can be represented by chemical formula 1', where the charges of the two nitrogen atoms are expressed as follows (i.e., chemical formula 1 with X4 being nitrogen and chemical formula 1' are identical to each other), and it is easy to understand that the explanation for chemical formula 1 with X4 being nitrogen also applies to chemical formula 1':

[0018] [ka] In the above chemical formula 1, ring CY2, ring CY 31 , Tamaki CY 32 And ring CY4 are C5-C independently of each other. 30 Carbon ring group or C1-C 30 It is a heterocyclic group.

[0019] According to one embodiment, the ring CY2, ring CY 31 , Tamaki CY 32 The ring CY4 is independently a benzene group, a naphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, or a benzoisoquinoline group.

[0020] According to other embodiments, the ring CY2, ring CY 31 and ring CY 32These are, independently of each other, a benzene group, a naphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, or a benzoisoquinoline group, and the ring CY4 is a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, or a benzoisoquinoline group.

[0021] In the above chemical formula 1, X 11 is N or C(R 11 ) and X 12 is N or C(R 12 ) and X 13 is N or C(R 13 ) and X 51 is N or C(R 51 ) and X 52 is N or C(R 52 ) and X 53 is N or C(R 53 ) and X 54 is N or C(R 54 ) and X 61 is N or C(R 61 ) and X 62 is N or C(R 62 ) and X 63 is N or C(R 63 ) and X 64 is N or C(R 64 ) and X 71 is N or C(R 71 ) and X 72 is N or C(R 72 ) and X 73 is N or C(R 73 ) and X 74 is N or C(R 74 ) is the above R 11 ~R 13 , R 51 ~R 54 , R 61 ~R 64 , R 71 ~R 74 For explanations relating to each of these, please refer to those provided in this specification.

[0022] According to one embodiment, in the chemical formula 1, X 11 is C(R 11 ) and X 12 is C(R 12 ) and X 13 is C(R 13 ) and X 51 is C(R 51 ) and X 52 is C(R 52 ) and X 53 is C(R 53 ) and X 54 is C(R 54 ) and X 61 is C(R 61 ) and X 62 is C(R 62 ) and X 63 is C(R 63 ) and X 64 is C(R 64 ) and X 71 is C(R 71 ) and X 72 is C(R 72 ) and X 73 is C(R 73 ) and X 74 is C(R 74 ) is the above R 51 ~R 54 , R 61 ~R 64 , R 71 ~R 74 For explanations relating to each of these, please refer to those provided in this specification.

[0023] In the above chemical formula 1, L1 is O, S, Se, N(R 101 ), C(R 101 )(R 102 ), or Si(R 101 )(R 102 )

[0024] According to one embodiment, in the chemical formula 1, L1 is O or S. 101 and R 102 For explanations relating to each of these, please refer to those provided in this specification.

[0025] In the above chemical formula 1, L2, L3, and L4 are independently a single bond, O, S, Se, N(R'), C(R')(R”), or Si(R')(R”), but at least one of L2, L3, and L4 is independently O, S, Se, N(R'), C(R')(R”), or Si(R')(R”).

[0026] According to one embodiment, at least one of L2, L3, and L4 in the chemical formula 1 is N(R').

[0027] According to other embodiments, at least one of L2, L3, and L4 of chemical formula 1 is independently O, S, or Se.

[0028] In another embodiment, at least one of L2, L3, and L4 of chemical formula 1 is independently C(R')(R”) or Si(R')(R”).

[0029] In another embodiment, two of L2, L3, and L4 in chemical formula 1 are single bonds, and the remaining one is not a single bond.

[0030] Furthermore, according to another embodiment, in the chemical formula 1, i) L2 and L3 are both single bonds, and L4 is O, S, Se, N(R'), C(R')(R”), or Si(R')(R”), ii) L2 and L4 are single bonds, L3 is O, S, Se, N(R'), C(R')(R”), or Si(R')(R”), or iii) L3 and L4 are both single bonds, and L2 is O, S, Se, N(R'), C(R')(R”), or Si(R')(R”).

[0031] In the above chemical formula 1, i) if L2 is N(R'), then R' is X 54 and X 61ii) If L3 is N(R'), then R' is X 64 and X 71 iii) If L4 is N(R'), then R' is X 74 and X 11 They are not linked to each of the others. That is, for example, compounds C3 and C4, as described later, are not included in chemical formula 1 of this specification.

[0032] In the above chemical formula 1, R 11 ~R 13 R2, R3, R4, R 51 ~R 54 , R 61 ~R 64 , R 71 ~R 74 , R 101 , R 102 R' and R'' are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl groups (e.g., substituted or unsubstituted C1-C) 20 C2-C (alkyl group), substituted or unsubstituted C2-C 60 Alkenyl group (e.g., substituted or unsubstituted C2-C) 20 Alkenyl group), substituted or unsubstituted C2-C 60 Alkynyl group, substituted or unsubstituted C1-C 60 Alkoxy group, substituted or unsubstituted C1-C 60 Alkylthio group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C1-C 10 Heterocycloalkenyl group, substituted or unsubstituted C6-C 60 Aryl group (e.g., substituted or unsubstituted C6-C) 20 Aryl group), substituted or unsubstituted C6-C60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio group, substituted or unsubstituted C1-C 60 Heteroaryl group (e.g., substituted or unsubstituted C1-C) 20 These are heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic groups, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), or -P(=O)(Q8)(Q9). For descriptions of each of the above Q1 to Q9, please refer to those specified herein.

[0033] According to one embodiment, R 11 ~R 13 R2, R3, R4, R 51 ~R 54 , R 61 ~R 64 , R 71 ~R 74 , R 101 , R 102 R' and R'' are independent of each other. Hydrogen, deuterium, -F, or cyano group; C1-C substituted or unsubstituted with deuterium, -F, cyano group, or any combination thereof. 20 alkyl group; Deuterium, -F, cyano group, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl alkyl groups, C1-C fluoride 20 Alkyl, C3-C 10 Cycloalkyl groups, deuterated C3-C 10 Cycloalkyl groups, fluoride C3-C 10 Cycloalkyl groups, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C1-C 20 Alkyl)phenyl group, naphthyl group, pyridinyl group, furanyl group, thiophenyl group, benzofuranyl group, benzothiophenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, -Si(Q 33)(Q 34 )(Q 35 ), -Ge(Q 33 )(Q 34 )(Q 35 ), or any combination thereof, C3-C 10 Cycloalkyl groups, phenyl groups, naphthyl groups, pyridinyl groups, furanyl groups, thiophenyl groups, benzofuranyl groups, benzothiophenyl groups, carbazolyl groups, dibenzofuranyl groups, or dibenzothiophenyl groups; or -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5);

[0034] According to other embodiments, R 11 ~R 13 R2, R3, R4, R 51 ~R 54 , R 61 ~R 64 , R 71 ~R 74 , R 101 , R 102 R' and R'' are independent of each other. Hydrogen or deuterium; or Deuterium, C1-C 20 C1-C11 is a C1-C11 molecule that is substituted or unsubstituted with an alkyl group, a phenyl group, a carbazolyl group (e.g., an N-carbazolyl group), or any combination thereof. 20 These are alkyl groups, phenyl groups, or carbazolyl groups (e.g., N-carbazolyl groups).

[0035] In this specification, "deuterium, C1-C 20 C1-C1 20 "Alkyl group, phenyl group, or carbazolyl group" refers to, for example, C1-C substituted with at least one deuterium 20 alkyl group, C1-C substituted with at least one phenyl group 20 alkyl group, C1-C substituted with at least one deuterium and at least one phenyl group 20 alkyl group, C1-C substituted with at least one deuterium and at least one deuterated phenyl group (e.g., a phenyl group substituted with five deuterium atoms) 20 alkyl group, C1-C substituted with at least one phenyl group 20 An alkyl group wherein the phenyl group comprises at least one deuterium and at least one C1-C 20 C1-C1 is substituted or unsubstituted with an alkyl group or any combination thereof. 20 alkyl group, A phenyl group substituted with at least one deuterium, at least one C1-C 20 Phenyl groups substituted with alkyl groups, At least one deuterium and at least one C1-C 20 Phenyl groups substituted with alkyl groups, At least one deuterium and at least one deuterated C1-C 20 Phenyl groups substituted with alkyl groups (e.g., -CD3, CD2H, -CDH2, -CD2CD3, -CH2CD3, etc.), at least one C1-C 20 Alkyl group and at least one deuterated C1-C 20 Phenyl groups substituted with alkyl groups, It includes a carbazolyl group substituted with at least one deuterium atom, etc.

[0036] Furthermore, according to another embodiment, R 11 ~R 13 R2, R3, R4, R 51 ~R 54 , R 61 ~R 64 , R 71 ~R 74 , R 101 , R 102 R' and R'' are independent of each other. Hydrogen or deuterium; Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec-decyl group, or tert-decyl group, substituted or unsubstituted with deuterium, phenyl group, or any combination thereof; or The group is a phenyl or carbazolyl group, substituted or unsubstituted with deuterium, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, or any combination thereof.

[0037] In further embodiments, the organometallic compound represented by chemical formula 1 comprises deuterium, a tert-butyl group substituted or unsubstituted with at least one deuterium, or any combination thereof.

[0038] In the above chemical formula 1, a2 to a4 represent the number of R2 to R4, respectively, and are integers of 0 to 20, 0 to 15, 0 to 10, 0 to 6, 0 to 5, 0 to 4, or 0 to 3, independently of each other. Each of a2 to a4 is a ring CY2, ring CY 31, Tamaki CY 32 Furthermore, the structure of ring CY4 allows for diverse selection within the aforementioned range. When a2 is 2 or more, the 2 or more R2s may be the same or different from each other; when a3 is 2 or more, the 2 or more R3s may be the same or different from each other; and when a4 is 2 or more, the 2 or more R4s may be the same or different from each other.

[0039] For example, a2 is an integer between 0 and 3.

[0040] As yet another example, a3 is an integer between 0 and 6.

[0041] As yet another example, a4 is an integer between 0 and 4.

[0042] As yet another example, a2 is not 0, and R2 is not hydrogen.

[0043] As yet another example, a4 is not 0, and R4 is not hydrogen.

[0044] According to one embodiment, the chemical formula 1 can satisfy at least one of the following conditions: <Condition 11> X 11 is C(R 11 ) and R 11 It is not hydrogen <Condition 12> X 12 is C(R 12 ) and R 12 It is not hydrogen <Condition 13> X 13 is C(R 13 ) and R 13 It is not hydrogen <Condition 51> X 51 is C(R 51 ) and R 51 It is not hydrogen <Condition 52> X 52 is C(R52 ) and R 52 It is not hydrogen <Condition 53> X 53 is C(R 53 ) and R 53 It is not hydrogen <Condition 54> X 54 is C(R 54 ) and R 54 It is not hydrogen <Condition 61> X 61 is C(R 61 ) and R 61 It is not hydrogen <Condition 62> X 62 is C(R 62 ) and R 62 It is not hydrogen <Condition 63> X 63 is C(R 63 ) and R 63 It is not hydrogen <Condition 64> X 64 is C(R 64 ) and R 64 It is not hydrogen <Condition 71> X 71 is C(R 71 ) and R 71 It is not hydrogen <Condition 72> X 72 is C(R 72 ) and R 72 It is not hydrogen <Condition 73> X 73 is C(R 73 ) and R 73 It is not hydrogen <Condition 74> X 74 is C(R 74 ) and R 74 It is not hydrogen The R of the above-mentioned <Condition 11> to <Condition 13>, <Condition 51> to <Condition 54>, <Condition 61> to <Condition 64>, and <Condition 71> to <Condition 74>11 ~R 13 , R 51 ~R 54 , R 61 ~R 64 and R 71 ~R 74 For explanations relating to each of these, please refer to those provided in this specification.

[0045] According to other embodiments, chemical formula 1 can satisfy at least one of the conditions 51 to 54, at least one of the conditions 61 to 64, at least one of the conditions 71 to 74, or any combination thereof.

[0046] Furthermore, according to other embodiments, the chemical formula 1 can satisfy at least one of the above-mentioned conditions 51 and 53.

[0047] Furthermore, according to other embodiments, the chemical formula 1 can satisfy at least one of the above conditions 62 and 63.

[0048] Furthermore, according to other embodiments, the chemical formula 1 can satisfy at least one of the above conditions 71 to 74.

[0049] For example, the R of the above-mentioned <Condition 11> to <Condition 13>, <Condition 51> to <Condition 54>, <Condition 61> to <Condition 64>, and <Condition 71> to <Condition 74> 11 ~R 13 , R 51 ~R 54 , R 61 ~R 64 and R 71 ~R 74 They are independent of each other, Deuterium, -F, or cyano group; C1-C substituted or unsubstituted with deuterium, -F, cyano group, or any combination thereof. 20 alkyl group; Deuterium, -F, cyano group, C1-C 20 Alkyl groups, deuterated C1-C20 Alkyl alkyl groups, C1-C fluoride 20 Alkyl, C3-C 10 Cycloalkyl groups, deuterated C3-C 10 Cycloalkyl groups, fluoride C3-C 10 Cycloalkyl groups, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C1-C 20 Alkyl)phenyl group, naphthyl group, pyridinyl group, furanyl group, thiophenyl group, benzofuranyl group, benzothiophenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, -Si(Q 33 )(Q 34 )(Q 35 ), -Ge(Q 33 )(Q 34 )(Q 35 ), or any combination thereof, C3-C 10 Cycloalkyl groups, phenyl groups, naphthyl groups, pyridinyl groups, furanyl groups, thiophenyl groups, benzofuranyl groups, benzothiophenyl groups, carbazolyl groups, dibenzofuranyl groups, or dibenzothiophenyl groups; or -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5);

[0050] In the above chemical formula 1, i)R 11 ~R 13 ii) Two or more of the following R2s, iii) Two or more of the following R3s, iv) Two or more of the following R4s, v) R 51 ~R 54 Two or more of the following, vi)R 61 ~R 64 Two or more of the above, vii)R 71 ~R 74 Two or more of the above, viiii)R 101 and R 102 , and ix) Each of R' and R'' is optionally linked to each other, and at least one R 10a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R10a Substitute or non-substitute C1-C 30 A heterocyclic group can be formed. 10a The explanation relating to this is as follows: 11 This is similar to the explanation provided.

[0051] Furthermore, according to another embodiment, the organometallic compound represented by chemical formula 1 is represented by the following chemical formula 1-1:

[0052] [ka] In the above chemical formula 1-1, M, X1~X4, X 11 ~X 13 , X 51 ~X 54 , X 61 ~X 64 , X 71 ~X 74 The explanations relating to L1 to L4 are the same as those described in this specification. X 21 is N or C(R 21 ) and X 22 is N or C(R 22 ) and X 23 is N or C(R 23 ) and R 21 ~R 23 The explanations relating to each of these are the same as the explanation relating to R2 in this specification. X 31 is N or C(R 31 ) and X 32 is N or C(R 32 ) and X 33 is N or C(R 33 ) and X 34 is N or C(R 34 ) and X 35 is N or C(R 35 ) and X 36 is N or C(R 36 ) and R 31 ~R 36The explanations relating to each of these are the same as the explanation relating to R3 in this specification. X 41 is N or C(R 41 ) and X 42 is N or C(R 42 ) and X 43 is N or C(R 43 ) and X 44 is N or C(R 44 ) and R 41 ~R 44 The explanations relating to each of these are the same as the explanation relating to R4 in this specification. i)R 11 ~R 13 ii) R 21 ~R 23 2 or more of the above, iii) R 31 ~R 36 Two or more of the following, and iv) R 41 ~R 44 Each of two or more of these is optionally connected to one R 10a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 10a Substitute or non-substitute C1-C 30 It can form a heterocyclic group, The aforementioned R 10a The explanation relating to this is as follows: 11 This is similar to the explanation provided.

[0053] In this specification, the descriptions relating to chemical formula 1 may also apply to chemical formula 1-1.

[0054] According to one embodiment, the chemical formula 1-1 can satisfy at least one of the following conditions: <Condition 21> X 21 is C(R 21 ) and R 21 It is not hydrogen <Condition 22> X 22 is C(R 22 ) and R 22It is not hydrogen <Condition 23> X 23 is C(R 23 ) and R 23 It is not hydrogen <Condition 31> X 31 is C(R 31 ) and R 31 It is not hydrogen <Condition 32> X 32 is C(R 32 ) and R 32 It is not hydrogen <Condition 33> X 33 is C(R 33 ) and R 33 It is not hydrogen <Condition 34> X 34 is C(R 34 ) and R 34 It is not hydrogen <Condition 35> X 35 is C(R 35 ) and R 35 It is not hydrogen <Condition 36> X 36 is C(R 36 ) and R 36 It is not hydrogen <Condition 41> X 41 is C(R 41 ) and R 41 It is not hydrogen <Condition 42> X 42 is C(R 42 ) and R 42 It is not hydrogen <Condition 43> X 43 is C(R 43 ) and R 43 It is not hydrogen <Condition 44> X 44 is C(R 44 ) and R 44 It is not hydrogen The R of the above-mentioned <Conditions 21> to <Condition 23>, <Conditions 31> to <Condition 36>, and <Conditions 41> to <Condition 44> 21 ~R 23 , R 31 ~R 36 and R 41 ~R 44 For explanations relating to each of these, please refer to those provided in this specification.

[0055] According to other embodiments, the chemical formula 1-1 can satisfy the above condition 42.

[0056] Furthermore, according to other embodiments, the chemical formula 1-1 can satisfy the above-mentioned conditions 22 and 42.

[0057] For example, the R of the above-mentioned <Conditions 21> to <Condition 23>, <Conditions 31> to <Condition 36>, and <Conditions 41> to <Condition 44> 21 ~R 23 , R 31 ~R 36 and R 41 ~R 44 They are independent of each other, Deuterium, -F, or cyano group; C1-C substituted or unsubstituted with deuterium, -F, cyano group, or any combination thereof. 20 alkyl group; Deuterium, -F, cyano group, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl alkyl groups, C1-C fluoride 20 Alkyl, C3-C 10 Cycloalkyl groups, deuterated C3-C 10 Cycloalkyl groups, fluoride C3-C 10 Cycloalkyl groups, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C1-C 20 Alkyl)phenyl group, naphthyl group, pyridinyl group, furanyl group, thiophenyl group, benzofuranyl group, benzothiophenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, -Si(Q33 )(Q 34 )(Q 35 ), -Ge(Q 33 )(Q 34 )(Q 35 ), or any combination thereof, C3-C 10 Cycloalkyl groups, phenyl groups, naphthyl groups, pyridinyl groups, furanyl groups, thiophenyl groups, benzofuranyl groups, benzothiophenyl groups, carbazolyl groups, dibenzofuranyl groups, or dibenzothiophenyl groups; or -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5);

[0058] In another embodiment, the organometallic compound represented by chemical formula 1 may be one of the following compounds 1 to 420:

[0059] [ka] TIFF2026090230000007.tif246170 TIFF2026090230000008.tif211170 TIFF2026090230000009.tif156170 TIFF2026090230000010.tif156170 TIFF2026090230000011.tif211170 TIFF2026090230000012.tif253170 TIFF2026090230000013.tif248170 TIFF2026090230000014.tif248170 TIFF2026090230000015.tif248170 TIFF2026090230000016.tif252170 TIFF2026090230000017.tif252170 TIFF2026090230000018.tif248170 TIFF2026090230000019.tif151170 TIFF2026090230000020.tif157170 TIFF2026090230000021.tif212170 TIFF2026090230000022.tif244170 TIFF2026090230000023.tif244170 TIFF2026090230000024.tif255170 TIFF2026090230000025.tif156170 TIFF2026090230000026.tif255170TIFF2026090230000027.tif255170 TIFF2026090230000028.tif243170 TIFF2026090230000029.tif252170TIFF2026090230000030.tif252170 TIFF2026090230000031.tif243170 TIFF2026090230000032.tif240170 TIFF2026090230000033.tif238170 TIFF2026090230000034.tif238170 TIFF2026090230000035.tif242170 TIFF2026090230000036.tif142170 In the above chemical formula 1, L2, L3, and L4 are independently a single bond, O, S, Se, N(R'), C(R')(R"), or Si(R')(R"), but at least one of L2, L3, and L4 is independently O, S, Se, N(R'), C(R')(R"), or Si(R')(R). In other words, in the aforementioned chemical formula 1, a 10-membered, 11-membered, or 12-membered ring is condensed onto the X1-containing benzimidazole ring while sharing a nitrogen adjacent to X1 (see Chemical Formula 1" below). In this way, the 10-membered, 11-membered, or 12-membered ring condensed onto the X1-containing benzimidazole ring while sharing a nitrogen adjacent to X1 effectively shields M, the central metal of chemical formula 1, stabilizing X1, the carbene moiety, and improving the stability and rigidity of chemical formula 1. Furthermore, the electron-donating properties of the organometallic compound represented by chemical formula 1 are improved, and the luminescence efficiency of the organometallic compound can be improved.

[0060] [ka] Furthermore, in chemical formula 1, i) if L2 is N(R'), then R' is X 54 and X 61 ii) If L3 is N(R'), then R' is X 64 and X 71 iii) If L4 is N(R'), then R' is X 74 and X 11 They are not linked to each of the others. That is, for example, compounds C3 and C4, as described later, are not included in Chemical Formula 1 as described herein. As a result, the structural degrees of freedom of the 10-membered ring, 11-membered ring, or 12-membered ring (see Chemical Formula 1") that is condensed to the X1-containing benzimidazole ring of Chemical Formula 1 while sharing a nitrogen adjacent to X1 is relatively increased, the structural strain angle due to the 10-membered ring, 11-membered ring, or 12-membered ring (see Chemical Formula 1") is relatively decreased, and the structural stability of the organometallic compound represented by Chemical Formula 1 can be improved.

[0061] The peak wavelength (emission peak wavelength, maximum emission peak wavelength, or maximum emission wavelength) of the peak having the maximum emission intensity in the emission spectrum of the organometallic compound is 440nm~470nm, 445nm~470nm, 450nm~470nm, 455nm~470nm, 460nm~470nm, 440nm~465nm, 445nm~465nm, 450nm~465nm, 455nm~465nm, or 460nm~465nm.

[0062] The full width at half maximum (FWHM) in the emission spectra of the organometallic compounds is 5nm to 50nm, 5nm to 40nm, 5nm to 30nm, 5nm to 20nm, 10nm to 50nm, 10nm to 40nm, 10nm to 30nm, 10nm to 20nm, 15nm to 50nm, 15nm to 40nm, 15nm to 30nm, or 15nm to 24nm.

[0063] The triplet energy (T1) of the organometallic compounds is 2.00eV~3.20eV, 2.00eV~3.00eV, 2.00eV~2.80eV, 2.50eV~3.20eV, 2.50eV~3.00eV, or 2.50eV~2.80eV.

[0064] The HOMO energy levels, LUMO energy levels, and T1 energy of compounds 5, 8, 10, 49, 50, 53, 66, 68, 78, 81, 95, 96, 125, 140, 155, 190, 280, 334, 335, 340, and 395 were evaluated using the Gaussian 09 program with molecular structure optimization based on density functional theory (DFT) using B3LYP. The results are shown in Table 1 below.

[0065] [Table 1] The synthesis methods for each of the organometallic compounds represented by the aforementioned chemical formula 1 can be understood by those skilled in the art by referring to the synthesis examples described later.

[0066] Therefore, each of the organometallic compounds represented by chemical formula 1 is suitable for use as a material for an intermediate layer of a light-emitting device, for example, a light-emitting layer in the intermediate layer. In other aspects, a light-emitting device is provided, comprising a first electrode, a second electrode, and an intermediate layer disposed between the first electrode and the second electrode and including a light-emitting layer, wherein the intermediate layer contains at least one organometallic compound represented by chemical formula 1.

[0067] The light-emitting element, by comprising an intermediate layer containing at least one organometallic compound represented by the aforementioned chemical formula 1, can have excellent driving voltage, excellent external quantum efficiency, and a relatively narrow full width at half maximum (FWHM) of the EL spectral emission peak.

[0068] The organometallic compound represented by chemical formula 1 may be used between a pair of electrodes of a light-emitting element. For example, the organometallic compound represented by chemical formula 1 is included in the light-emitting layer. In this case, the light-emitting layer may further contain a host. The content (e.g., by weight) of the host is greater than the content (e.g., by weight) of the organometallic compound. The light-emitting layer can emit red light, green light, or blue light. For example, the organometallic compound can emit blue light.

[0069] According to one embodiment, the CIEy values ​​of the light emitted from the light-emitting layer are 0.040~0.170, 0.050~0.170, 0.060~0.170, 0.040~0.165, 0.050~0.165, or 0.060~0.165.

[0070] According to other embodiments, the CIEy values ​​of the light emitted from the light-emitting layer containing the organometallic compound represented by chemical formula 1 as an emitter are 0.130-0.170, 0.135-0.170, 0.140-0.170, 0.130-0.165, 0.135-0.165, 0.140-0.165, 0.130-0.160, 0.135-0.160, or 0.140-0.160.

[0071] In another embodiment, the CIEy values ​​of the light emitted from the light-emitting layer containing the organometallic compound represented by chemical formula 1 as a sensorizer are 0.070-0.140, 0.080-0.140, 0.090-0.140, 0.070-0.135, 0.080-0.135, 0.090-0.135, 0.100-0.135, 0.110-0.135, 0.120-0.135, or 0.125-0.135.

[0072] In yet another embodiment, the emission peak wavelength of the light emitted from the light-emitting layer is 440nm-470nm, 445nm-470nm, 450nm-470nm, 455nm-470nm, 460nm-470nm, 440nm-465nm, 445nm-465nm, 455nm-465nm, 455nm-465nm, or 460nm-465nm.

[0073] The light-emitting layer may further include a host. A description of the host is provided herein.

[0074] For example, the configuration of the light-emitting layer is as follows: <First Embodiment> The light-emitting layer contains at least one organometallic compound represented by chemical formula 1, and the organometallic compound can act as an emitter, for example, a phosphorescent emitter. That is, the organometallic compound is an emitter. For example, of the total light-emitting components of the light-emitting layer, the light-emitting component emitted from the organometallic compound is 80% or more, 85% or more, 90% or more, or 95% or more. The light emitted from the organometallic compound is blue light. In addition to the organometallic compound represented by chemical formula 1, the light-emitting layer may further contain a phosphorescent compound different from the organometallic compound, a fluorescent compound, or any combination thereof. Here, the phosphorescent compound and / or fluorescent compound can act as a sensorizer or an auxiliary dopant.

[0075] <Second Embodiment> The light-emitting layer contains at least one organometallic compound represented by chemical formula 1, and the organometallic compound can act as a sensorizer or an auxiliary dopant. That is, the organometallic compound is a sensorizer or an auxiliary dopant. The light-emitting layer may further contain an emitter different from the organometallic compound. For example, of the total light-emitting components of the light-emitting layer, the light-emitting component emitted from the emitter is 80% or more, 85% or more, 90% or more, or 95% or more. The light emitted from the emitter is blue light. The emitter may contain a phosphorescent compound, a fluorescent compound, or any combination thereof, different from the organometallic compound.

[0076] In the second embodiment, the emitter content is 1 to 100 parts by weight, 5 to 50 parts by weight, or 10 to 20 parts by weight per 100 parts by weight of the organometallic compound represented by chemical formula 1.

[0077] In the second embodiment, the total amount of the organometallic compound represented by chemical formula 1 and the emitter is 1 to 30 parts by weight, 3 to 20 parts by weight, or 5 to 15 parts by weight per 100 parts by weight of the light-emitting layer.

[0078] In the second embodiment, the fluorescent compound usable as an emitter does not contain a transition metal.

[0079] For example, in the second embodiment, the fluorescent compound that can be used as an emitter is a fluorescent emission substance that does not contain cyano groups (-CN) and fluoro groups (-F).

[0080] As yet another example, the fluorescent compounds that can be used as emitters in the second embodiment include immediate fluorescent compounds, delayed fluorescent compounds (e.g., thermally activated delayed fluorescent compounds), or combinations thereof.

[0081] As yet another example, the fluorescent compounds that can be used as emitters in the second embodiment are condensed ring-containing compounds, amino group-containing compounds, styryl group-containing compounds, or boron-containing compounds.

[0082] As yet another example, a fluorescent compound that can be used as an emitter in the second embodiment is a multi-resonance thermally activated delayed fluorescent compound.

[0083] According to one embodiment, the fluorescent compound usable as an emitter in the second embodiment includes i) an amine-based fluorescent compound and / or ii) a fluorescent compound containing a condensed polycyclic ring in which a 6-membered ring containing nitrogen and boron is condensed.

[0084] According to one embodiment, the fluorescent compound usable as an emitter in the second embodiment includes a naphthalene group, a fluorene group, a spirobifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, anthracene group, a fluorantene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group (tetracene group), a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a group represented by one of the following chemical formulas 501-1 to 501-21, or any combination thereof:

[0085] [ka] According to other embodiments, the fluorescent compounds usable as emitters in the second embodiment include compounds represented by the following chemical formulas 501A or 501B:

[0086] [ka] In the aforementioned chemical formulas 501A and 501B, Ar 501This is a group represented by naphthalene, fluorene, spirobifluorene, benzofluorene, dibenzofluorene, phenanthrene, anthracene, fluorantene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, indenoanthracene, bisanthracene, or one of the chemical formulas 501-1 to 501-21. R 511 Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, or -Si(Q 501 )(Q 502 )(Q 503 ) and xd5 is an integer between 0 and 10. L 501 ~L 503 They are independent of each other, Single bond; or Deuterium, -F, -Cl, -Br, -I, hydroxyl group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -Si(Q 501 )(Q 502 )(Q 503 ), or any combination thereof, C3-C 10 Cycloalkylene group, C1-C 10 Heterocycloalkylene group, C3-C 10 Cycloalkenylene group, C1-C 10 Heterocycloalkenylene group, C6-C 60 Arylene group, C1-C 60 A heteroarylene group, a divalent non-aromatic condensed polycyclic group, or a divalent non-aromatic heterocondensed polycyclic group; xd1 to xd3 are 1, 2, or 3, independently of each other. R 501 and R 502 These are, independently of each other, deuterium, -F, -Cl, -Br, -I, hydroxyl group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -Si(Q 501 )(Q 502 )(Q 503 ), or any combination thereof, substituted or unsubstituted, phenyl group, naphthyl group, fluorenyl group, spirobifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenantrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazole group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, or dibenzosilolyl group, Z 11 Deuterium, -F, -Cl, -Br, -I, hydroxyl group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -Si(Q 501 )(Q 502 )(Q 503 ), or any combination thereof, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 It is a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic heterocondensed polycyclic group. xd4 is 1, 2, 3, 4, 5, or 6. The aforementioned Q 501 ~Q 503 These are, independently of each other, hydrogen, C1-C 60 Alkyl alkyl group, C1-C 60 Alkoxy group, C6-C 60 Aryl group, C1-C 60 It is a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic heterocondensed polycyclic group.

[0087] According to other embodiments, the fluorescent compound comprises a compound represented by the chemical formula 501A or 501B, wherein xd4 in chemical formula 501A is 1, 2, 3, 4, 5, or 6, and xd4 in chemical formula 501B is 2, 3, or 4.

[0088] According to other embodiments, the fluorescent compounds usable as emitters in the second embodiment include compounds represented by the following chemical formulas 503-1 or 503-2.

[0089] [ka] In the aforementioned chemical formulas 503-1 and 503-2, Y 51 ~Y 54 These are independent of each other, single bonds, O, S, N[(L 506 ) xd6 -R 506 ], C[(L 506 ) xd6 -R 506 ][(L 507 ) xd7 -R 507], or Si[(L 506 ) xd6 -R 506 ][(L 507 ) xd7 -R 507 ] and m53 is either 0 or 1. L 501 ~L 507 The explanations relating to the above are as follows: 501 Refer to the explanation below. For explanations related to xd1 to xd7, please refer to the explanation for xd1 in the aforementioned chemical formula 501. R 501 ~R 507 They are independent of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl group, or C1-C 20 Alkoxy group; Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spirobifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenantrenyl group, anthracenyl group, pyrenyl group, crisenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazole group, triazinyl group, dibenzofuranyl group, or dibenzothiophenyl group; or Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl alkyl group, C1-C 20Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, fluorenyl groups, spirobifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenantrenyl groups, anthracenyl groups, pyrenyl groups, chrysenyl groups, pyridinyl groups, pyrazinyl groups, pyrimidinyl groups, pyridadinyl groups, quinolinyl groups, isoquinolinyl groups, quinoxalinyl groups, quinazolinyl groups, carbazolyl groups, triazinyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, or any combination thereof. A compound-substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spirobifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenantrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, triazinyl group, dibenzofuranyl group, or dibenzothiophenyl group; xd21 and xd23 are 0, 1, 2, 3, or 4, independently of each other. xd22 and xd24 are 0, 1, 2, or 3, independently of each other. xd25 is 0, 1, or 2. R 501 ~R 507 Two of these can selectively bond to each other to form a saturated or unsaturated ring.

[0090] The fluorescent dopant includes, for example, the following compounds FD(1) to FD(16), FD1 to FD14, or any combination thereof:

[0091] [ka] In this specification, "(the intermediate layer) contains one or more organometallic compounds" is also interpreted as "(the intermediate layer) contains one organometallic compound belonging to the category of chemical formula 1, or two or more different organometallic compounds belonging to the category of chemical formula 1."

[0092] For example, the intermediate layer may contain only compound 1 as the organometallic compound. In this case, compound 1 may be present in the light-emitting layer of the light-emitting element. Alternatively, the intermediate layer may contain both compound 1 and compound 2 as the organometallic compound. In this case, compound 1 and compound 2 may be present in the same layer (for example, both compound 1 and compound 2 may be present in the light-emitting layer).

[0093] The first electrode is the anode of a hole injection electrode and the second electrode is the cathode of an electron injection electrode, or the first electrode is the cathode of an electron injection electrode and the second electrode is the anode of a hole injection electrode.

[0094] For example, in the light-emitting element, the first electrode is an anode, the second electrode is a cathode, and 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, wherein the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0095] In this specification, “intermediate layer” refers to one and / or more layers disposed between the first electrode and the second electrode in a light-emitting element. The “intermediate layer” includes not only organic compounds but also organometallic complexes containing metals.

[0096] Figure 1 schematically shows a cross-sectional view of an organic light-emitting element 10, which is one of the light-emitting elements according to one embodiment of the present invention. The structure and manufacturing method of the organic light-emitting element according to one embodiment of the present invention will be described below with reference to Figure 1. The organic light-emitting element 10 has a structure in which a first electrode 11, an intermediate layer 15, and a second electrode 19 are stacked in order.

[0097] A substrate may be further placed below the first electrode 11 or above the second electrode 19. While a substrate commonly used in organic light-emitting devices can be used as the substrate, a glass substrate or a transparent plastic substrate with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water repellency can also be used.

[0098] The first electrode 11 is formed, for example, by providing a material for the first electrode on the upper part of a substrate using a vapor deposition method or a sputtering method. The first electrode 11 is also an anode. The material for the first electrode includes a material having a high work function so as to facilitate hole injection. The first electrode 11 is a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. As the material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc. can be used. Alternatively, metals such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) can be used.

[0099] The first electrode 11 may have a single layer or a multilayer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO.

[0100] An intermediate layer 15 is placed on top of the first electrode 11.

[0101] The intermediate layer 15 includes a hole transport region, an emission layer, and an electron transport region.

[0102] The hole transport region is located between the first electrode 11 and the light-emitting layer.

[0103] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.

[0104] The hole transport region may consist only of a hole injection layer, or only of a hole transport layer. Alternatively, the hole transport region may have a structure of hole injection layer / hole transport layer or hole injection layer / hole transport layer / electron blocking layer, stacked sequentially from the first electrode 11.

[0105] If the hole transport region includes a hole injection layer, the hole injection layer (HIL) is formed on top of the first electrode 11 using various methods such as vacuum deposition, spin coating, casting, and LB (Langmuir-Blodgett) method.

[0106] When forming a hole injection layer by vacuum deposition, the deposition conditions vary depending on the compound used as the material for the hole injection layer, the desired structure of the hole injection layer, and its thermal properties. For example, the deposition temperature is approximately 100°C to 500°C, and the vacuum level is approximately 10°C. -8 torr~approximately 10 -3 Torr is selected within the range of approximately 0.01 Å / sec to approximately 100 Å / sec, but is not limited to these ranges.

[0107] When forming a hole injection layer by spin coating, the coating conditions vary depending on the compound used as the material for the hole injection layer, the desired structure of the hole injection layer, and its thermal properties. However, the coating speed is typically selected between approximately 2,000 rpm and 5,000 rpm, and the heat treatment temperature for solvent removal after coating is typically between approximately 80°C and 200°C, although these conditions are not limited to these.

[0108] The formation conditions for the hole transport layer and the electron blocking layer refer to the formation conditions for the hole injection layer.

[0109] The hole transport region may include, for example, m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), compounds represented by the following chemical formula 201, compounds represented by the following chemical formula 202, or any combination thereof:

[0110] [ka] [Chemical formula 201] TIFF2026090230000046.tif89170[Chemical formula 202] TIFF2026090230000047.tif41170 In the above chemical formula 201, Ar 101 and Ar 102 These are, independently of each other, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkyl groups, C1-C 10Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Phenylene, pentarenylene, indenylene, naphthylene, azurenylene, heptarenylene, acenaphthylene, fluorenylene, phenalenylene, phenantrenylene, anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenyrenylene, naphthracenylene, picenylene, perylenenylene, or pentasenylene group, which are substituted or unsubstituted with heteroaryl groups, monovalent nonaromatic condensed polycyclic groups, monovalent nonaromatic heterocondensed polycyclic groups, or any combination thereof.

[0111] In the aforementioned chemical formula 201, xa and xb are independent integers between 0 and 5, or 0, 1, or 2. For example, xa is 1 and xb is 0, but is not limited to that.

[0112] In the above chemical formulas 201 and 202, the R 101 ~R 108 , R 111 ~R 119 and R 121 ~R 124 They are independent of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl groups (e.g., methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc.), or C1-C 10 Alkoxy groups (e.g., methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, etc.); Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, or any combination thereof, C1-C 10 Alkyl or C1-C 10 Alkoxy group; or Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl alkyl group, C1-C 10 A phenyl group, naphthyl group, anthracenyl group, fluorenyl group, or pyrenyl group, substituted or unsubstituted with an alkoxy group, or any combination thereof;

[0113] In the above chemical formula 201, R 109 Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl alkyl group, C1-C 20 A phenyl group, naphthyl group, anthracenyl group, or pyridinyl group, which is substituted or unsubstituted with an alkoxy group, a phenyl group, anthracenyl group, or pyridinyl group, or any combination thereof.

[0114] According to one embodiment, the compound represented by chemical formula 201 is represented by the following chemical formula 201A:

[0115] [ka] In the aforementioned chemical formula 201A, R 101 , R 111 , R 112 and R 109 For a detailed explanation, please refer to the above.

[0116] For example, the hole transport region includes one of the following compounds HT1 to HT20 or any combination thereof:

[0117] [ka] TIFF2026090230000050.tif192170 The thickness of the hole transport region is approximately 100 Å to approximately 10,000 Å, for example, approximately 100 Å to approximately 1,000 Å. If the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, the thickness of the hole injection layer is approximately 100 Å to approximately 10,000 Å, for example, approximately 100 Å to approximately 1,000 Å, and the thickness of the hole transport layer is approximately 50 Å to approximately 2,000 Å, for example, approximately 100 Å to approximately 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the above-described ranges, the hole transport characteristics to be satisfied can be obtained without a substantial increase in driving voltage.

[0118] The hole transport region may further contain, in addition to the aforementioned substances, charge-generating materials to improve conductivity. The charge-generating materials are uniformly or non-uniformly dispersed within the hole transport region.

[0119] The charge-generating substance is, for example, a p-type dopant. The p-type dopant is a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof. For example, the p-type dopant is a quinone derivative such as tetracyanoquinone dimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethane (F4-TCNQ), F6-TCNNQ; a metal oxide such as tungsten oxide and molybdenum oxide; a cyano group-containing compound such as the compound HT-D1 below; or any combination thereof.

[0120] [ka] The hole transport region may further include a buffer layer.

[0121] The buffer layer can compensate for the optical resonance distance due to the wavelength of light emitted from the light-emitting layer, thereby increasing efficiency.

[0122] On the other hand, if the hole transport region includes an electron blocking layer, the material of the electron blocking layer includes a substance usable in the hole transport region as described above, a host substance as described later, or any combination thereof. For example, if the hole transport region includes an electron blocking layer, mCP as described later can be used as the material of the electron blocking layer.

[0123] An emissive layer (EML) can be formed on top of the hole transport region using methods such as vacuum deposition, spin coating, casting, or LB. When forming the emissive layer by vacuum deposition or spin coating, the deposition and coating conditions vary depending on the compound used, but are generally selected within approximately the same range as those used for forming the hole injection layer.

[0124] The light-emitting layer comprises a host and a dopant, the dopant may comprise an organometallic compound represented by chemical formula 1 as described herein.

[0125] The host may contain TPBi, TBADN, ADN (also known as "DNA"), CBP, CDBP, TCP, mCP, compound H50, compound H51, compound H52, or any combination thereof:

[0126] [ka] If the organic light-emitting element is a full-color organic light-emitting element, the light-emitting layer may be patterned with a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer. Alternatively, the light-emitting layer may have a structure in which a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer are laminated, allowing it to emit white light, and various other modifications are possible.

[0127] When the light-emitting layer contains a host and a dopant, the dopant content is usually selected in the range of about 0.01 to about 15 parts by weight, based on about 100 parts by weight of the host, but is not limited thereto.

[0128] The thickness of the light-emitting layer is approximately 100 Å to approximately 1,000 Å, for example, approximately 200 Å to approximately 600 Å. When the thickness of the light-emitting layer satisfies the above range, excellent light-emitting characteristics can be achieved without a substantial increase in driving voltage.

[0129] Next, an electron transport region is placed above the light-emitting layer.

[0130] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0131] For example, the electron transport region may have, but is not limited to, a hole blocking layer / electron transport layer / electron injection layer or an electron transport layer / electron injection layer structure. The electron transport layer may be a single layer or a multilayer structure containing two or more different materials.

[0132] The formation conditions for the hole blocking layer, electron transport layer, and electron injection layer in the electron transport region refer to the formation conditions for the hole injection layer.

[0133] If the electron transport region includes a hole blocking layer, the hole blocking layer includes, for example, at least one of the following: BCP, Bphen, and Balq:

[0134] [ka] Alternatively, the hole blocking layer may include the host, an electron transport layer material, an electron injection layer material (described later), or any combination thereof.

[0135] The thickness of the hole blocking layer is approximately 20 Å to 1,000 Å, for example, approximately 30 Å to 600 Å. When the thickness of the hole blocking layer satisfies the above range, excellent hole blocking characteristics can be obtained without a substantial increase in driving voltage.

[0136] The electron transport layer may include BCP, Bphen, TPBi, Alq3, Balq, TAZ, NTAZ, or any combination thereof:

[0137] [ka] Alternatively, the electron transport layer may contain one of the following compounds ET1 to ET25 or any combination thereof:

[0138] [ka] TIFF2026090230000056.tif195170 The thickness of the electron transport layer is approximately 100 Å to approximately 1,000 Å, for example, approximately 150 Å to approximately 500 Å. When the thickness of the electron transport layer satisfies the above range, the electron transport characteristics to be satisfied can be obtained without a substantial increase in the driving voltage.

[0139] The electron transport layer may further contain metal-containing materials in addition to the materials described above.

[0140] The metal-containing substance may also contain a Li complex. The Li complex may include, for example, the following compounds ET-D1 or ET-D2.

[0141] [ka] Furthermore, the electron transport region includes an electron injection layer (EIL) that facilitates the injection of electrons from the second electrode 19.

[0142] The electron injection layer may contain LiF, NaCl, CsF, Li2O, BaO, or any combination thereof.

[0143] The thickness of the electron injection layer is approximately 1 Å to approximately 100 Å, for example, approximately 3 Å to approximately 90 Å. When the thickness of the electron injection layer satisfies the above range, the desired electron injection characteristics can be obtained without a substantial increase in the driving voltage.

[0144] A second electrode 19 is positioned on the upper part of the intermediate layer 15. The second electrode 19 also serves as the cathode. As the material for the second electrode 19, a metal, alloy, conductive compound, or any combination thereof with a relatively low work function can be used. Specifically, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc., can be used as the material for forming the second electrode 19. Alternatively, various modifications are possible, such as forming a transmissive second electrode 19 using ITO or IZO to obtain a front-facing light-emitting element.

[0145] The organic light-emitting element described above has been explained with reference to Figure 1, but is not limited to that.

[0146] Furthermore, from another perspective, the light-emitting element is included in various electronic devices. Therefore, an electronic device including the light-emitting element is provided.

[0147] The electronic device may further include, in addition to the light-emitting element, i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and / or color conversion layer may be positioned in at least one direction of propagation of the light emitted from the light-emitting element. For example, the light emitted from the light-emitting element may be blue light, green light, or white light. A description of the light-emitting element should be seen above. According to one embodiment, the color conversion layer may include quantum dots.

[0148] The electronic device includes a first substrate. The first substrate includes a plurality of sub-pixel regions, the color filter includes a plurality of color filter regions corresponding to each of the plurality of sub-pixel regions, and the color conversion layer includes a plurality of color conversion regions corresponding to each of the plurality of sub-pixel regions.

[0149] A pixel definition film is placed between the multiple sub-pixel regions, and each sub-pixel region is defined.

[0150] The color filter may further include a plurality of color filter regions and a light-shielding pattern disposed between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light-shielding pattern disposed between the plurality of color conversion regions.

[0151] The electronic device may further include a thin-film transistor in addition to the light-emitting element described above. The thin-film transistor includes a source electrode, a drain electrode, and an active layer, and either one of the source electrode and the drain electrode may be electrically connected to either one of the first electrode and the second electrode of the light-emitting element.

[0152] The thin-film transistor may further include a gate electrode, a gate insulating film, and the like.

[0153] The active layer includes crystalline silicon, amorphous silicon, organic semiconductors, oxide semiconductors, and the like.

[0154] The electronic device may further include a sealing portion that seals the light-emitting element. The sealing portion is positioned between the color filter and / or color conversion layer and the light-emitting element. The sealing portion allows light from the light-emitting element to be extracted to the outside while simultaneously blocking the penetration of outside air and moisture into the light-emitting element. 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 sealing layer including one or more organic and / or inorganic layers. When the sealing portion is a thin film sealing layer, the electronic device is flexible.

[0155] In addition to the color filter and / or color conversion layer, various functional layers may be further arranged on the sealed portion depending on the application of the electronic device. Examples of the functional layers include a touchscreen layer and a polarizing layer. The touchscreen layer may be a reduced-pressure touchscreen layer, an electrostatic touchscreen layer, or an infrared touchscreen layer.

[0156] According to one embodiment, the electronic device includes the light-emitting element and a sealing portion that seals the light-emitting element.

[0157] According to another embodiment, a method for manufacturing an electronic device including the light-emitting element and a sealing part that seals the light-emitting element, The steps of manufacturing the light-emitting element, A method for manufacturing an electronic device is provided, which includes the step of manufacturing a sealed part that protects the light-emitting element from outside air and moisture.

[0158] In further embodiments, the electronic device can be applied to one of the following: flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, indoor or outdoor lighting and / or signal lights, head-up displays, fully or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, telephones, mobile phones, tablets, phablets, PDAs (personal digital assistants), wearable devices (e.g., watches), laptop computers, personal computers, digital cameras, camcorders, viewfinders, microdisplays, 3D displays, virtual or augmented reality displays, vehicles, video walls including tiled multiple displays, theater or stadium screens, phototherapy devices, billboards, electronic organizers, electronic dictionaries, and electronic game consoles.

[0159] Since the light-emitting element has excellent driving voltage and external quantum efficiency characteristics, the electronic device including the light-emitting element can have high-quality characteristics such as high brightness, high resolution, and low power consumption.

[0160] Furthermore, from another perspective, a diagnostic composition is provided that contains one or more organometallic compounds represented by the chemical formula 1.

[0161] Since the organometallic compound represented by chemical formula 1 can provide high luminescence efficiency, the diagnostic composition containing the organometallic compound can have high diagnostic efficiency.

[0162] The diagnostic composition can be applied in a variety of ways, including to various diagnostic kits, diagnostic reagents, biosensors, and biomarkers.

[0163] In this specification, C1-C 60 Alkyl groups refer to monovalent groups of saturated aliphatic hydrocarbons that are linear or branched, having 1 to 60 carbon atoms, C1-C 60 The alkylene group is the C1-C 60 This refers to a divalent group that has the same structure as an alkyl group.

[0164] In this specification, C1-C 60 Alkyl alkyl group, C1-C 20 Alkyl groups, and / or C1-C 10Examples of alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec-decyl group, tert-decyl group, or any combination thereof. This includes mixed-substituted or unsubstituted methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, sec-butyl groups, isobutyl groups, tert-butyl groups, n-pentyl groups, tert-pentyl groups, neopentyl groups, isopentyl groups, sec-pentyl groups, 3-pentyl groups, sec-isopentyl groups, n-hexyl groups, isohexyl groups, sec-hexyl groups, tert-hexyl groups, n-heptyl groups, isoheptyl groups, sec-heptyl groups, tert-heptyl groups, n-octyl groups, isooctyl groups, sec-octyl groups, tert-octyl groups, n-nonyl groups, isononyl groups, sec-nonyl groups, tert-nonyl groups, n-decyl groups, isodecyl groups, sec-decyl groups, or tert-decyl groups. For example, the aforementioned chemical formula 9-33 is a branched C6 alkyl group, which appears to be a tert-butyl group substituted with two methyl groups.

[0165] In this specification, C1-C 60 The alkoxy group is -OA 101 (Here, A 101 The above C1-C 60 It means a monovalent group having the chemical formula C1-C (which is an alkyl group). 60 The alkylthio group is -OA 102 (Here, A 102 The above C1-C 60 This refers to a monovalent group having the chemical formula (which is an alkyl group).

[0166] In this specification, C1-C 60 Alkoxy group, C1-C 20 Alkoxy group, or C1-C 10 Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, and pentoxy groups.

[0167] In this specification, C2-C 60 The alkenyl group is the C2-C 60 A structure having one or more carbon-carbon double bonds in the middle or terminal of an alkyl group, specific examples of which include ethenyl, propenyl, and butenyl groups. In this specification, C2-C 60 The alkenylene group is the C2-C 60 This refers to a divalent group that has the same structure as an alkenyl group.

[0168] In this specification, C2-C 60 The alkynyl group is the C2-C 60 It has a structure containing one or more carbon-carbon triple bonds in the middle or terminal of an alkyl group, and specific examples include an ethynyl group, a propynyl group, etc. In this specification, C2-C 60 The alkynylene group is the C2-C 60 This refers to a divalent group that has the same structure as an alkynyl group.

[0169] In this specification, C3-C 10 Cycloalkyl groups refer to monovalent saturated hydrocarbon ring groups with 3 to 10 carbon atoms, C3-C 10 The cycloalkylene group is the C3-C 10 This refers to a divalent group having the same structure as a cycloalkyl group.

[0170] In this specification, C3-C 10Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantanyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl (norbornyl), and bicyclo[2.2.2]octyl.

[0171] In this specification, C1-C 10 A heterocycloalkyl group refers to a monovalent monocyclic group having 1 to 10 carbon atoms, containing at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, and is C1-C 10 The heterocycloalkylene group is the C1-C 10 This refers to a divalent group having the same structure as a heterocycloalkyl group.

[0172] In this specification, C1-C 10 Examples of heterocycloalkyl groups include siloranil, silinanil, tetrahydrofuranil, tetrahydro-2H-pyranil, and tetrahydrothiophenyl groups.

[0173] In this specification, C3-C 10 A cycloalkenyl group is a monovalent monocyclic group having 3 to 10 carbon atoms and containing at least one carbon-carbon double bond within the ring, but lacking aromaticity. Specific examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl groups. In this specification, C3-C 10 The cycloalkenylene group is the C3-C 10 This refers to a divalent group that has the same structure as a cycloalkenyl group.

[0174] In this specification, C1-C 10 A heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms, containing at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, and having at least one double bond within the ring. 10Specific examples of heterocycloalkenyl groups include the 2,3-dihydrofuranyl group and the 2,3-dihydrothiophenyl group. In this specification, C1-C 10 The heterocycloalkenylene group is the C1-C 10 This refers to a divalent group that has the same structure as a heterocycloalkenyl group.

[0175] In this specification, C6-C 60 The aryl group refers to a monovalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms, C6-C 60 The arylene group refers to a divalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms. 60 Specific examples of aryl groups include phenyl, naphthyl, anthracenyl, phenantrenyl, pyrenyl, and chrysenyl groups. 60 Aryl group and C6-C 60 If the arylene group contains two or more rings, the two or more rings are fused together.

[0176] In this specification, C7-C 60 The alkylaryl group is at least one C1-C 60 C6-C substituted with alkyl group 60 It means an aryl group.

[0177] In this specification, C1-C 60 A heteroaryl group is defined as a monovalent group having a cyclic aromatic system with 1 to 60 carbon atoms, containing at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom. 60 A heteroarylene group refers to a divalent group having a carbocyclic aromatic system with 1 to 60 carbon atoms, containing at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom. 60 Specific examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridadinyl, triazinyl, quinolinyl, and isoquinolinyl groups. 60 Heteroaryl group and C1-C 60If a heteroarylene group contains two or more rings, the two or more rings are fused to each other.

[0178] In this specification, C2-C 60 The alkyl heteroaryl group is at least one C1-C 60 C1-C substituted with alkyl group 60 It means a heteroaryl group.

[0179] In this specification, C6-C 60 The aryloxy group is -OA 103 (Here, A 103 is the above C6-C 60 (It is an aryl group) and C6-C 60 The arylthio group is -SA 104 (Here, A 104 is the above C6-C 60 It indicates that it is an aryl group.

[0180] In this specification, a monovalent non-aromatic condensed polycyclic group means a monovalent group (for example, having 8 to 60 carbon atoms) in which two or more rings are fused to each other, containing only carbon as the ring-forming atom, and having non-aromaticity as a whole molecule. Specific examples of the monovalent non-aromatic condensed polycyclic group include the fluorenyl group. In this specification, a divalent non-aromatic condensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

[0181] In this specification, a monovalent non-aromatic heterocondensed polycyclic group means a monovalent group (for example, having 1 to 60 carbon atoms) in which two or more rings are fused to each other, and which contains, in addition to carbon, heteroatoms selected from N, O, P, Si, S, Se, Ge, and B as ring-forming atoms, and the entire molecule is non-aromatic. The monovalent non-aromatic heterocondensed polycyclic group includes a carbazolyl group, etc. In this specification, a divalent non-aromatic heterocondensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic heterocondensed polycyclic group.

[0182] In this specification, C5-C 30A carbocyclic group is a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring-forming atoms. 30 A carbocyclic group is either a monocyclic or polycyclic group. (at least one R 10a (Substituted or not substituted) C5-C 30 A "carbon ring group" is, for example, (at least one R 10a This includes adamantane groups (substituted or unsubstituted), norbornene groups, bicyclo[1.1.1]pentane groups, bicyclo[2.1.1]hexane groups, bicyclo[2.2.1]heptane groups (norbornane groups), bicyclo[2.2.2]octane groups, cyclopentane groups, cyclohexane groups, cyclohexene groups, benzene groups, naphthalene groups, anthracene groups, phenanthrene groups, triphenylene groups, pyrene groups, chrysene groups, 1,2,3,4-tetrahydronaphthalene groups, cyclopentadiene groups, fluorene groups, etc.

[0183] In this specification, C1-C 30 A heterocyclic group is a saturated or unsaturated cyclic group having 1 to 30 carbon atoms as ring-forming atoms, as well as at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B. 30 A heterocyclic group is either a monocyclic or polycyclic group. (at least one R 10a (Substituted or not substituted) C1-C 30 A heterocyclic group is, for example, (at least one R 10aThiophene group (substituted or unsubstituted), furan group, pyrrole group, silole group, borol group, phosphole group, selenofen group, gelmol group, benzothiophene group, benzofuran group, indole group, benzosilole group, benzobolol group, benzophosphole group, benzoselenophene group, benzogermol group, dibenzothiophene group, dibenzofuran group, carbazole group, dibenzosilole group, dibenzobolol group, dibenzophosphole group, dibenzoselenophene group, dibenzogermol group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzosilole group, azabenzobolol group, azabenzophosphole group, azabenzoselenophene group, azabenzogermol group, azadibenzothiophene group, azadibenzofuran group, azacarb Zole group, azafluorene group, azadibenzosilol group, azadibenzobolol group, azadibenzophosphole group, azadibenzoselenophene group, azadibenzogermole group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, This includes phenanthroline groups, pyrazole groups, imidazole groups, triazole groups, oxazole groups, isoxazole groups, thiazole groups, isothiazole groups, oxadiazole groups, thiadiazole groups, benzopyrazole groups, benzimidazole groups, benzoxazole groups, benzothiazole groups, benzoxadiazole groups, benzothiadiazole groups, 5,6,7,8-tetrahydroisoquinoline groups, 5,6,7,8-tetrahydroquinoline groups, and the like.

[0184] In this specification, "fluorinated C1-C 60 Alkyl group (or C1-C fluoride) 20 (Alkyl alkyl groups, etc.), Fluoride C3-C 10 Cycloalkyl group, C1-C fluoride 10The heterocycloalkyl group and the phenyl fluoride group are each substituted with at least one fluoro group (-F), C1-C 60 Alkyl group (or C1-C 20 (Alkyl alkyl groups, etc.), C3-C 10 Cycloalkyl groups, C1-C 10 This refers to heterocycloalkyl groups and phenyl groups. For example, "C1 alkyl fluoride (i.e., methyl fluoride group)" includes -CF3, -CF2H, and -CFH2. 60 Alkyl group (or C1-C fluoride) 20 (Alkyl alkyl groups, etc.), Fluoride C3-C 10 Cycloalkyl group, C1-C fluoride 10 A "heterocycloalkyl group" or "phenyl fluoride group" is a fully fluorinated C1-C group in which all hydrogen atoms in each group are replaced by fluoro groups. 60 Alkyl group (or fully fluorinated C1-C) 20 Alkyl alkyl groups, etc.), fully fluorinated C3-C 10 Cycloalkyl groups, fully fluorinated C1-C 10 ii) a heterocycloalkyl group, or a fully fluorinated phenyl group, or ii) a partially fluorinated C1-C group in which not all hydrogen atoms in each group are substituted with fluoro groups. 60 Alkyl group (or partially fluorinated C1-C 20 (Alkyl alkyl groups, etc.), partially fluorinated C3-C 10 Cycloalkyl groups, partially fluorinated C1-C 10 It is a heterocycloalkyl group, or partly a phenyl fluoride group.

[0185] In this specification, "deuterated C1-C 60 Alkyl group (or deuterated C1-C 20 (Alkyl groups, etc.), Deuterated C3-C 10 Cycloalkyl group, Deuterated C1-C 10 The heterocycloalkyl group and the deuterated phenyl group are each C1-C groups substituted with at least one deuterium atom. 60Alkyl group (or C1-C 20 (Alkyl alkyl groups, etc.), C3-C 10 Cycloalkyl groups, C1-C 10 This refers to heterocycloalkyl groups and phenyl groups. For example, "deuterated C1 alkyl group (i.e., deuterated methyl group)" includes -CD3, -CD2H, and -CDH2. The aforementioned "deuterated C1-C 60 Alkyl group (or deuterated C1-C 20 (Alkyl groups, etc.), Deuterated C3-C 10 Cycloalkyl group, Deuterated C1-C 10 "Heterocycloalkyl group" or "deuterated phenyl group" is a fully deuterated C1-C group in which all hydrogen atoms in each group are replaced with deuterium. 60 Alkyl group (or fully deuterated C1-C 20 Alkyl groups, etc.), fully deuterated C3-C 10 Cycloalkyl groups, fully deuterated C1-C 10 ii) a heterocycloalkyl group, or a fully deuterated phenyl group, or ii) a partially deuterated C1-C group in which not all hydrogen atoms in each group are substituted with deuterium. 60 Alkyl group (or partially deuterated C1-C 20 (Alkyl groups, etc.), partially deuterated C3-C 10 Cycloalkyl groups, partially deuterated C1-C 10 It is a heterocycloalkyl group, or a partially deuterated phenyl group.

[0186] In this specification, "(C1-C 20 The alkyl group 'X' is defined as at least one C1-C 20 This indicates an 'X' group substituted with an alkyl group. For example, in this specification, "(C1-C 20 Alkyl)C3-C 10 A "cycloalkyl group" is defined as a group with at least one C1-C 20 C3-C substituted with alkyl group 10 This indicates a cycloalkyl group, "(C1-C 20 A "(alkyl)phenyl group" is defined as at least one C1-C 20This shows a phenyl group substituted with an alkyl group. An example of a (C1 alkyl)phenyl group is the toluyl group.

[0187] In this specification, "azaindole group, azabenzoborol group, azabenzophosphole group, azaindene group, azabenzosilol group, azabenzogermol group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborol group, azadibenzophosphole group, azafluorene group, azadibenzosilol group, azadibenzogermol group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group" each This refers to a heterocycle that has the same backbone as "indole group, benzoborol group, benzophosphole group, indene group, benzosilol group, benzogermol group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborol group, dibenzophosphole group, fluorene group, dibenzosilol group, dibenzogermol group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group," but in which at least one of the carbon atoms forming the ring is substituted with nitrogen.

[0188] The substituted C5-C 30 Carbocyclic group, substituted C2-C 30 Heterocyclic group, substituted C1-C 60 Alkyl alkyl group, substituted C2-C 60 Alkenyl group, substituted C2-C 60 Alkynyl group, substituted C1-C 60 Alkoxy group, substituted C1-C 60 Alkylthio group, substituted C3-C 10 Cycloalkyl groups, substituted C1-C 10 Heterocycloalkyl groups, substituted C3-C 10 Cycloalkenyl group, substituted C1-C 10Heterocycloalkenyl group, substituted C6-C 60 Aryl group, substituted C7-C 60 Alkylaryl group, substituted C6-C 60 Aryloxy group, substituted C6-C 60 Arylthio group, substituted C1-C 60 Heteroaryl group, substituted C2-C 60 The substituents of alkylheteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic hetero-condensed polycyclic group are independent of each other and are Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, or C1-C 60 Alkoxy group; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C7-C 60 Alkylaryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, C2-C 60 Alkylheteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic hetero-condensed polycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q15 ), -B(Q 16 )(Q 17 ), -P(=O)(Q 18 )(Q 19 ), -P(Q 18 )(Q 19 ), or any combination thereof, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, or C1-C 60 Alkoxy group; C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C7-C 60 Alkylaryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, C2-C 60 Alkyl heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, or monovalent non-aromatic heterocondensed polycyclic groups; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C7-C 60 Alkylaryl group, C6-C 60 Aryloxy group, C6-C 60An arylthio group, C1-C 60 A heteroaryl group, C2-C 60 An alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(=O)(Q 28 )(Q 29 )、-P(Q 28 )(Q 29 )、or a C3-C 10 cycloalkyl group, a C1-C 10 heterocycloalkyl group, a C3-C 10 cycloalkenyl group, a C1-C 10 heterocycloalkenyl group, a C6-C 60 aryl group, a C7-C 60 alkylaryl group, a C6-C 60 aryloxy group, a C6-C 60 arylthio group, a C1-C 60 heteroaryl group, a C2-C 60 alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic heterocyclic condensed polycyclic group; -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39 )、or -P(Q 38 )(Q 39 ); or any combination thereof; is.

[0189] In this specification, Q1~Q9, Q 11 ~Q 19 、Q 21 ~Q 29 and Q 31 ~Q 39They are independent of each other, Hydrogen, deuterium, or -F; or Deuterium, -F, cyano group, C1-C 60 Alkyl alkyl group, C6-C 60 A C1-C group that is substituted or unsubstituted with an aryl group, or any combination thereof. 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C1-C 60 Alkylthio group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 It is a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic heterocondensed polycyclic group.

[0190] The following describes in more detail a compound and a light-emitting element according to one embodiment of the present invention, with reference to synthesis examples and examples, but the present invention is not limited to the following synthesis examples and examples. In the following synthesis examples, the expression "'B' was used instead of 'A'" means that the amount of "B" used and the amount of "A" used are the same on a molar equivalent basis.

[0191] [Examples] Synthesis example 1 (compound 5)

[0192] [ka] Synthesis of compound 5E Compound 5A (8.00 g, 27.0 mmol), Compound 5B (16.2 g, 32.4 mmol), Tetrakis(triphenylphosphine)palladium(0)(Pd(PPh3)4) (3.12 g, 2.70 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos) (2.22 g, 5.40 mmol), and K2CO3 (7.47 g, 54.0 mmol) were placed in a round-bottom flask. This mixture was then combined with 1,4-dioxane / H2O (120 mL / 30 mL), and the mixture was refluxed at 110°C for 16 hours with stirring. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried with anhydrous MgSO4, and then filtered. The resulting filtrate was concentrated and purified by silica gel column chromatography to obtain 9.0 g (57% yield) of compound 5E.

[0193] LC-MS:589.27[M+H]+ Synthesis of compound 5F Compound 5E (9.0 g, 15.3 mmol) and K2CO3 (6.34 g, 45.9 mmol) were placed in a round-bottom flask, mixed with dimethylformamide (DMF) (160 mL), and stirred at 100°C for 13 hours. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added to obtain an organic solution layer. This layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and then filtered. The resulting filtrate was concentrated and purified by silica gel column chromatography to obtain 4.2 g (48% yield) of compound 5F.

[0194] LC-MS:568.27[M+H]+ Synthesis of compound 5G Compound 5F (4.20 g, 7.39 mmol), Pd / C (10 wt% on carbon, 0.79 g, 0.74 mmol), and ammonium formate (9.31 g, 148 mmol) were placed in a round-bottom flask. After mixing with ethanol (75 mL), the mixture was refluxed at 80°C for 13 hours and stirred. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 3.39 g (yield 85%) of compound 5G.

[0195] LC-MS:538.29[M+H]+ Synthesis of compound 5I In a round-bottom flask, compound 5G (3.39 g, 6.29 mmol), compound 5H (3.11 g, 6.61 mmol), Pd2(dba)3 (0.58 g, 0.63 mmol), SPhos (0.52 g, 1.26 mmol), and sodium tert-butoxide (NaOtBu) (0.91 g, 9.44 mmol) were added. After mixing with toluene (65 mL), the mixture was refluxed at 110°C for 13 hours and stirred. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 5.2 g (yield 89%) of compound 5I.

[0196] LC-MS:929.47[M+H]+ Synthesis of compound 5J Compound 5I (5.2 g, 5.60 mmol) was placed in a round-bottom flask and mixed with triethyl orthoformate (50 mL). Then, 35 wt% hydrochloric acid (0.58 ml, 6.72 mmol) was added, and the mixture was stirred at 80°C for 3 hours. After the reaction was complete, the temperature was lowered to room temperature, the mixture was concentrated under reduced pressure, and purified by silica gel column chromatography to obtain 5.19 g (yield 95%) of compound 5J.

[0197] Synthesis of Compound 5 In a round-bottom flask, compound 5J (5.19g, 5.32 mmol), K2PtCl4 (2.52g, 5.85 mmol), and sodium acetate (NaOAc) (1.57g, 16.0 mmol) were added. After mixing with dioxane (100 mL), the mixture was refluxed at 100°C for 12 hours and stirred. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 3.4 g (yield 56%) of compound 5.

[0198] LC-MS:1132.28[M+H]+ Synthesis example 2 (compound 125)

[0199] [ka] Synthesis of compound 125C Compound 125A (10.0 g, 20.9 mmol), compound 125B (5.8 g, 31.4 mmol), Pd(PPh3)4 (2.42 g, 2.09 mmol), SPhos (1.72 g, 4.18 mmol), and K2CO3 (5.78 g, 41.8 mmol) were placed in a round-bottom flask. This was then mixed with 1,4-dioxane / H2O (80 mL / 20 mL), and the mixture was refluxed and stirred at 110°C for 16 hours. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 7.50 g (yield 67%) of compound 125C.

[0200] LC-MS:538.05[M+H]+ Synthesis of compound 125E In a round-bottom flask, compound 125C (7.50 g, 13.9 mmol), compound 125D (8.51 g, 20.9 mmol), Pd(PPh3)4 (1.61 g, 1.39 mmol), SPhos (1.14 g, 2.79 mmol), and K2CO3 (3.85 g, 27.9 mmol) were added. These were then mixed with 1,4-dioxane / H2O (60 mL / 15 mL) and stirred under reflux at 110°C for 16 hours. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 8.50 g (yield 83%) of compound 125E.

[0201] LC-MS:739.35[M+H]+ Synthesis of compound 125F Compound 125E (8.5 g, 11.5 mmol) and K2CO3 (4.77 g, 34.5 mmol) were placed in a round-bottom flask, mixed with DMF (120 mL), and stirred at 100°C for 16 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic solution layer obtained by adding ethyl acetate and saturated ammonium chloride aqueous solution was extracted using ethyl acetate, dried with anhydrous MgSO4, and filtered. The resulting filtrate was concentrated and purified by silica gel column chromatography to obtain 5.30 g (yield 64%) of compound 125F.

[0202] LC-MS:719.36[M+H]+ Synthesis of compound 125G Compound 125F (5.30 g, 7.37 mmol), Pd / C (10 wt% on carbon, 0.78 g, 0.74 mmol), and ammonium formate (9.30 g, 147 mmol) were placed in a round-bottom flask. After mixing with ethanol (75 mL), the mixture was refluxed at 80°C for 4 hours and stirred. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 3.60 g (yield 71%) of compound 125G.

[0203] LC-MS:689.37[M+H]+ Synthesis of compound 125I In a round-bottom flask, compound 125G (3.60 g, 5.23 mmol), compound 5H (2.59 g, 5.49 mmol), Pd2(dba)3 (0.48 g, 0.52 mmol), SPhos (0.43 g, 1.05 mmol), and NaOtBu (0.75 g, 7.84 mmol) were added. After mixing with toluene (55 mL), the mixture was refluxed at 110°C for 15 hours and stirred. After the reaction was complete, the temperature was lowered to room temperature, and the organic solution layer obtained by adding ethyl acetate and saturated ammonium chloride aqueous solution was extracted using ethyl acetate, dried with anhydrous MgSO4, and filtered. The resulting filtrate was concentrated and purified by silica gel column chromatography to obtain 4.80 g (yield 85%) of compound 125I.

[0204] LC-MS:1079.55[M+H]+ Synthesis of compound 125J Compound 125I (4.80 g, 4.45 mmol) was placed in a round-bottom flask and mixed with triethyl orthoformate (40 mL). Then, 35 wt% hydrochloric acid (0.46 ml, 5.34 mmol) was added, and the mixture was stirred at 80°C for 3 hours. After the reaction was complete, the temperature was lowered to room temperature, the mixture was concentrated under reduced pressure, and purified by silica gel column chromatography to obtain 4.90 g (98% yield) of compound 125J.

[0205] Synthesis of compound 125 Compound 125J (4.90g, 4.35 mmol), K2PtCl4 (2.07g, 4.79 mmol), and NaOAc (1.28g, 13.1 mmol) were placed in a round-bottom flask. After mixing with dioxane (90 mL), the mixture was refluxed at 100°C for 15 hours and stirred. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 3.08 g (yield 55%) of compound 125.

[0206] LC-MS:1282.48[M+H]+ Synthesis example 3 (compound 140)

[0207] [ka] Synthesis of compound 140C In a round-bottom flask, compound 140A (12.0 g, 24.3 mmol), compound 125B (6.73 g, 36.4 mmol), Pd(PPh3)4 (2.80 g, 2.43 mmol), SPhos (1.99 g, 4.86 mmol), and K2CO3 (6.71 g, 48.6 mmol) were added. These were then mixed with 1,4-dioxane / H2O (100 mL / 25 mL) and stirred under reflux at 110°C for 15 hours. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 8.60 g (yield 64%) of compound 140C.

[0208] LC-MS:554.05[M+H]+ Synthesis of compound 140E In a round-bottom flask, compound 140C (8.60 g, 15.5 mmol), compound 125D (9.48 g, 23.3 mmol), Pd(PPh3)4 (1.79 g, 1.55 mmol), SPhos (1.27 g, 3.10 mmol), and K2CO3 (4.29 g, 31.0 mmol) were added. These were then mixed with 1,4-dioxane / H2O (65 mL / 15 mL) and stirred under reflux at 110°C for 15 hours. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 8.35 g (71% yield) of compound 140E.

[0209] LC-MS:755.33[M+H]+ Synthesis of compound 140F Compound 140E (8.35 g, 11.1 mmol) and K2CO3 (4.59 g, 33.2 mmol) were placed in a round-bottom flask, mixed with DMF (110 mL), and stirred at 100°C for 16 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic solution layer obtained by adding ethyl acetate and saturated ammonium chloride aqueous solution was extracted using ethyl acetate, dried with anhydrous MgSO4, and filtered. The resulting filtrate was concentrated and purified by silica gel column chromatography to obtain 4.70 g (yield 58%) of compound 140F.

[0210] LC-MS:735.32[M+H]+ Synthesis of compound 140G In a round-bottom flask, compound 140F (4.70 g, 6.39 mmol), Pd / C (10 wt% on carbon, 0.68 g, 0.64 mmol), and ammonium formate (8.06 g, 128 mmol) were added. After mixing with ethanol (65 mL), the mixture was refluxed at 80°C for 4 hours and stirred. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 3.82 g (yield 85%) of compound 140G.

[0211] LC-MS:705.36[M+H]+ Synthesis of compound 140I In a round-bottom flask, compound 140G (3.82g, 5.42 mmol), compound 5H (2.68g, 5.69 mmol), Pd2(dba)3 (0.50g, 0.54 mmol), SPhos (0.44g, 1.08 mmol), and NaOtBu (0.78g, 8.13 mmol) were added. After mixing with toluene (55 mL), the mixture was refluxed at 110°C for 17 hours and stirred. After the reaction was complete, the temperature was lowered to room temperature, and the organic solution layer obtained by adding ethyl acetate and saturated ammonium chloride aqueous solution was extracted using ethyl acetate, dried with anhydrous MgSO4, and filtered. The resulting filtrate was concentrated and purified by silica gel column chromatography to obtain 4.50 g (yield 76%) of compound 140I.

[0212] LC-MS:1095.52[M+H]+ Synthesis of compound 140J Compound 140I (4.50 g, 4.11 mmol) was placed in a round-bottom flask and mixed with triethyl orthoformate (35 mL). Then, 35 wt% hydrochloric acid (0.42 ml, 4.93 mmol) was added, and the mixture was stirred at 80°C for 3 hours. After the reaction was complete, the temperature was lowered to room temperature, the mixture was concentrated under reduced pressure, and purified by silica gel column chromatography to obtain 4.53 g (yield 97%) of compound 140J.

[0213] Synthesis of compound 140 In a round-bottom flask, compound 140 J (4.53 g, 3.97 mmol), K2PtCl4 (1.88 g, 4.36 mmol), and NaOAc (1.17 g, 11.9 mmol) were added. After mixing with dioxane (80 mL), the mixture was refluxed at 100°C for 17 hours and stirred. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 2.66 g (yield 52%) of compound 140.

[0214] LC-MS:1298.47[M+H]+ Synthesis example 4 (compound 155)

[0215] [ka] Synthesis of compound 155E Compound 155A (4.20 g, 9.07 mmol), compound 125D (5.54 g, 13.6 mmol), Pd(PPh3)4 (1.05 g, 0.91 mmol), SPhos (0.74 g, 1.81 mmol), and K2CO3 (2.51 g, 18.1 mmol) were placed in a round-bottom flask. This was then mixed with 1,4-dioxane / H2O (40 mL / 10 mL), and the mixture was refluxed at 110°C for 19 hours with stirring. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 5.00 g (yield 83%) of compound 155E.

[0216] LC-MS:664.32[M+H]+ Synthesis of compound 155F Compound 155E (5.00 g, 7.53 mmol) and K2CO3 (3.12 g, 22.6 mmol) were placed in a round-bottom flask, mixed with DMF (75 mL), and stirred at 100°C for 16 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic solution layer obtained by adding ethyl acetate and saturated ammonium chloride aqueous solution was extracted using ethyl acetate, dried with anhydrous MgSO4, and filtered. The resulting filtrate was concentrated and purified by silica gel column chromatography to obtain 2.05 g (42% yield) of compound 155F.

[0217] LC-MS:644.32[M+H]+ Synthesis of compound 155G Compound 155F (2.05 g, 3.18 mmol), Pd / C (10 wt% on carbon, 0.34 g, 0.32 mmol), and ammonium formate (4.02 g, 63.7 mmol) were placed in a round-bottom flask. After mixing with ethanol (32 mL), the mixture was refluxed at 80°C for 3 hours and stirred. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 1.66 g (yield 85%) of compound 155G.

[0218] LC-MS:614.33[M+H]+ Synthesis of compound 155I In a round-bottom flask, compound 155G (1.66 g, 2.70 mmol), compound 5H (1.34 g, 2.84 mmol), Pd2(dba)3 (0.25 g, 0.27 mmol), SPhos (0.22 g, 0.54 mmol), and NaOtBu (0.39 g, 4.06 mmol) were added. After mixing with toluene (30 mL), the mixture was refluxed at 110°C for 15 hours and stirred. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 1.80 g (yield 66%) of compound 155I.

[0219] LC-MS:1004.51[M+H]+ Synthesis of compound 155J Compound 155I (1.80 g, 1.79 mmol) was placed in a round-bottom flask and mixed with triethyl orthoformate (15 mL). Then, 35 wt% hydrochloric acid (0.18 ml, 2.15 mmol) was added, and the mixture was stirred at 80°C for 3 hours. After the reaction was complete, the temperature was lowered to room temperature, the mixture was concentrated under reduced pressure, and purified by silica gel column chromatography to obtain 1.65 g (yield 88%) of compound 155J.

[0220] Synthesis of compound 155 Compound 155J (1.65g, 1.57 mmol), K2PtCl4 (0.75g, 1.73 mmol), and NaOAc (0.46g, 4.71 mmol) were placed in a round-bottom flask. After mixing with dioxane (30 mL), the mixture was refluxed at 100°C for 18 hours and stirred. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 1.10 g (yield 58%) of compound 155.

[0221] LC-MS:1207.45[M+H]+ Synthesis example 5 (compound 190)

[0222] [ka] Synthesis of compound 190E In a round-bottom flask, compound 190A (5.00 g, 11.3 mmol), compound 125D (6.88 g, 16.9 mmol), Pd(PPh3)4 (1.30 g, 1.13 mmol), SPhos (0.92 g, 2.25 mmol), and K2CO3 (3.11 g, 22.5 mmol) were added. These were then mixed with 1,4-dioxane / H2O (40 mL / 10 mL) and stirred under reflux at 110°C for 5 hours. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 7.15 g (99% yield) of compound 190E.

[0223] LC-MS:645.32[M+H]+ Synthesis of compound 190F Compound 190E (1.63 g, 2.53 mmol) and K2CO3 (1.05 g, 7.58 mmol) were placed in a round-bottom flask, mixed with DMF (25 mL), and stirred at 100°C for 16 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic solution layer obtained by adding ethyl acetate and saturated ammonium chloride aqueous solution was extracted using ethyl acetate, dried with anhydrous MgSO4, and filtered. The resulting filtrate was concentrated and purified by silica gel column chromatography to obtain 1.03 g (yield 65%) of compound 190F.

[0224] LC-MS:625.32[M+H]+ Synthesis of compound 190G In a round-bottom flask, compound 190F (1.03 g, 1.65 mmol), Pd / C (10 wt% on carbon, 0.18 g, 0.16 mmol), and ammonium formate (2.08 g, 33.0 mmol) were added. After mixing with ethanol (20 mL), the mixture was refluxed at 80°C for 3 hours and stirred. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 0.93 g (yield 95%) of compound 190G.

[0225] LC-MS:595.35[M+H]+ Synthesis of compound 190I In a round-bottom flask, compound 190G (0.93g, 1.56 mmol), compound 5H (0.77g, 1.64 mmol), Pd2(dba)3 (0.14g, 0.16 mmol), SPhos (0.13g, 0.31 mmol), and NaOtBu (0.23g, 2.35 mmol) were added. After mixing with toluene (20 mL), the mixture was refluxed at 110°C for 5 hours and stirred. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 1.42 g (yield 92%) of compound 190I.

[0226] LC-MS:985.53[M+H]+ Synthesis of compound 190J Compound 190I (1.42 g, 1.44 mmol) was placed in a round-bottom flask and mixed with triethyl orthoformate (12 mL). Then, 35 wt% hydrochloric acid (0.15 ml, 1.73 mmol) was added, and the mixture was stirred at 80°C for 2 hours. After the reaction was complete, the temperature was lowered to room temperature, the mixture was concentrated under reduced pressure, and purified by silica gel column chromatography to obtain 1.45 g (98% yield) of compound 190J.

[0227] Synthesis of compound 190 Compound 190 (1.45 g, 1.41 mmol), K2PtCl4 (0.67 g, 1.55 mmol), and NaOAc (0.41 g, 4.22 mmol) were placed in a round-bottom flask. After mixing with dioxane (30 mL), the mixture was refluxed at 100°C for 13 hours and stirred. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 1.05 g (yield 63%) of compound 190.

[0228] LC-MS:1188.47[M+H]+ Synthesis example 6 (compound 395)

[0229] [ka] Synthesis of compound 395E In a round-bottom flask, compound 395A (7.00 g, 16.7 mmol), compound 125D (10.2 g, 25.1 mmol), Pd(PPh3)4 (1.93 g, 1.67 mmol), SPhos (1.37 g, 3.34 mmol), and K2CO3 (4.62 g, 33.4 mmol) were added. These were then mixed with 1,4-dioxane / H2O (75 mL / 20 mL) and stirred under reflux at 110°C for 18 hours. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 6.20 g (yield 56%) of compound 395E.

[0230] LC-MS:664.32[M+H]+ Synthesis of compound 395F Compound 395E (6.20 g, 9.34 mmol) and K2CO3 (3.87 g, 28.0 mmol) were placed in a round-bottom flask, mixed with DMF (95 mL), and stirred at 100°C for 16 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic solution layer obtained by adding ethyl acetate and saturated ammonium chloride aqueous solution was extracted using ethyl acetate, dried with anhydrous MgSO4, and filtered. The resulting filtrate was concentrated and purified by silica gel column chromatography to obtain 2.35 g (yield 39%) of compound 395F.

[0231] LC-MS:644.32[M+H]+ Synthesis of compound 395G Compound 395F (2.35 g, 3.65 mmol), Pd / C (10 wt% on carbon, 0.39 g, 0.37 mmol), and ammonium formate (4.60 g, 73.0 mmol) were placed in a round-bottom flask. After mixing with ethanol (40 mL), the mixture was refluxed at 80°C for 3 hours and stirred. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 1.83 g (yield 82%) of compound 395G.

[0232] LC-MS:614.33[M+H]+ Synthesis of compound 395I In a round-bottom flask, compound 395G (1.83 g, 2.98 mmol), compound 5H (1.48 g, 3.13 mmol), Pd2(dba)3 (0.27 g, 0.30 mmol), SPhos (0.24 g, 0.60 mmol), and NaOtBu (0.43 g, 4.47 mmol) were added. After mixing with toluene (30 mL), the mixture was refluxed at 110°C for 15 hours and stirred. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 1.92 g (yield 64%) of compound 395I.

[0233] LC-MS:1004.51[M+H]+ Synthesis of compound 395J Compound 395I (1.92 g, 1.91 mmol) was placed in a round-bottom flask and mixed with triethyl orthoformate (20 mL). Then, 35 wt% hydrochloric acid (0.20 mL, 2.29 mmol) was added, and the mixture was stirred at 80°C for 3 hours. After the reaction was complete, the temperature was lowered to room temperature, the mixture was concentrated under reduced pressure, and purified by silica gel column chromatography to obtain 1.73 g (86% yield) of compound 395J.

[0234] Synthesis of compound 395 Compound 395J (1.73g, 1.65 mmol), K2PtCl4 (0.78g, 1.81 mmol), and NaOAc (0.48g, 4.94 mmol) were placed in a round-bottom flask. After mixing with dioxane (35 mL), the mixture was refluxed at 100°C for 18 hours and stirred. After the reaction was complete, the temperature was lowered to room temperature, and then ethyl acetate and saturated ammonium chloride aqueous solution were added. The resulting organic solution layer was extracted using ethyl acetate, dried over anhydrous MgSO4, and filtered. The obtained filtrate was concentrated and purified by silica gel column chromatography to obtain 1.15 g (yield 58%) of compound 395.

[0235] LC-MS:1207.45[M+H]+ Evaluation Example 1 After mixing 0.5 wt% of compound 5 into a PMMA in CH2Cl2 solution, the resulting product was coated onto a quartz substrate using a spin coater, then heat-treated in an 80°C oven, and cooled to room temperature to produce a film.

[0236] The quantum luminescence yields in film of the aforementioned film were evaluated using Hamamatsu Photonics' absolute PL quantum yield analyzer, which is equipped with a xenon light source, monochromator, photonic multichannel analyzer, and integrating sphere, and employs PLQY measurement software (Hamamatsu Photonics K.K., Shizuoka, Japan). This evaluation was then repeated for the remaining compounds listed in Table 2, and the results are shown in Table 2. In Table 2, the PLQY values ​​for compounds 5, 125, 140, 155, 190, 395, C2, C3, and C4 are shown as relative values ​​(%) to the PLQY of compound C1.

[0237] [Table 2]

[0238] [ka] From Table 2 above, it can be confirmed that compounds 5, 125, 140, 155, 190, and 395 have superior PLQY properties compared to compounds C1, C2, C3, and C4.

[0239] Example 1 A glass substrate with a 1500Å thick ITO electrode was cut to a size of 50mm × 50mm × 0.5mm, and after ultrasonic cleaning in acetone, isopropyl alcohol, and pure water for 15 minutes each, it was cleaned with UV ozone for 30 minutes.

[0240] Next, m-MTDATA was deposited onto the ITO electrode (anode) on the glass substrate to form a 600 Å thick hole injection layer, and α-NPD was deposited on the hole injection layer to form a 250 Å thick hole transport layer.

[0241] Compound 5 (emitter) and CBP (host) were co-deposited onto the hole transport layer in a weight ratio of 10:90 to form a 400 Å thick light-emitting layer.

[0242] A light-emitting element having the structure ITO / m-MTDATA(600Å) / α-NPD(250Å) / CBP+compound 5(10 wt%)(400Å) / BAlq(50Å) / Alq3(300Å) / LiF(10Å) / Al(1200Å) was fabricated by depositing BAlq on the light-emitting layer to form a 50Å thick hole-blocking layer, depositing Alq3 on the hole-blocking layer to form a 300Å thick electron-transport layer, depositing LiF on the electron-transport layer to form a 10Å thick electron-injection layer, and then vacuum-depositing Al on the electron-injection layer to form a 1,200Å thick second electrode (cathode).

[0243] [ka] Examples 2-5 and Comparative Examples C1, C2 A light-emitting element was fabricated using the same method as in Example 1, except that a compound listed in Table 3 was used as the emitter instead of compound 5 during the formation of the light-emitting layer.

[0244] Evaluation Example 2 For each light-emitting element fabricated in Examples 1-5 and Comparative Examples C1 and C2, the driving voltage, external quantum efficiency (EQE), CIE color coordinates, and FWHM of the emission peaks in the EL spectrum were evaluated, and the results are shown in Table 3. The driving voltage and external quantum efficiency were evaluated using an ammeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A). The CIE color coordinates and FWHM of the emission peaks in the EL spectrum were measured for each light-emitting element using a luminance meter (Minolta Cs-1000A) and the EL spectrum (at 1,000 cd / m²).2 The evaluation was performed based on the following. In Table 3, the drive voltage and external quantum efficiency of Examples 1 to 5 and Comparative Example C2 are shown as relative values ​​(%) to the drive voltage and external quantum efficiency of Comparative Example C1, respectively.

[0245] [Table 3]

[0246] [ka] From Table 3 above, it can be confirmed that the light-emitting elements of Examples 1 to 5 emit blue light with excellent color purity and a relatively narrow FWHM, while also having superior driving voltage and superior external quantum efficiency compared to the light-emitting elements of Comparative Examples C1 and C2.

[0247] Example 6 and Comparative Examples C3 and C4 A light-emitting element was fabricated using the same method as in Example 1, except that the compound listed in Table 4 was used as the emitter instead of compound 5 during the formation of the light-emitting layer.

[0248] Evaluation Example 3 For each light-emitting element fabricated in Example 6 and Comparative Examples C3 and C4, the driving voltage, external quantum efficiency (EQE), and CIE color coordinates were evaluated using the same method as in Evaluation Example 2, and the results are shown in Table 4. Data for Comparative Examples C1 and C2 have also been added to Table 4, and in Table 4, the driving voltage and external quantum efficiency of Example 6 and Comparative Examples C2 to C4 are shown as relative values ​​(%) to the driving voltage and external quantum efficiency of Comparative Example C1, respectively.

[0249] [Table 4]

[0250] [ka] From Table 4 above, it can be confirmed that the light-emitting element of Example 6 emits blue light with excellent color purity, and has superior driving voltage and superior external quantum efficiency compared to the light-emitting elements of Comparative Examples C1 to C4.

[0251] Example 7 A light-emitting element was fabricated using the same method as in Example 1, except that during the formation of the light-emitting layer, compound 155 (sensitizer), compound FD14 (emitter), and CBP (host) were co-deposited in a weight ratio of 10:1.5:88.5 to form a 400 Å thick light-emitting layer.

[0252] Comparative Example X A light-emitting element was fabricated using the same method as in Example 1, except that during the formation of the light-emitting layer, compounds FD14 (emitter) and CBP (host) were co-deposited in a weight ratio of 10:90 to form a 400 Å thick light-emitting layer.

[0253] Evaluation Example 4 For each light-emitting element fabricated in Example 7 and Comparative Example X, the emission peak wavelength of the EL spectrum, the y value of the color coordinate (CIEy), the external quantum efficiency (EQE), and the driving voltage were evaluated using the same method as described in Evaluation Example 2, and the results are shown in Table 5. In Table 5, the external quantum efficiency and driving voltage of the light-emitting elements in Example 7 and Comparative Example X are all shown as relative values ​​(%).

[0254] [Table 5]

[0255] [ka] From Table 5 above, it can be confirmed that the light-emitting element of Example 7, which contains compound 155 as a sensor, emits blue light with excellent color purity while having superior external quantum efficiency and superior driving voltage characteristics compared to the light-emitting element of Comparative Example X. [Explanation of symbols]

[0256] 10 Organic light-emitting devices 11 1st electrode 15 Middle Class 19 2nd electrode

Claims

1. The organometallic compound is represented by the following chemical formula 1: 【Chemistry 1】 In the aforementioned chemical formula 1, M is either Pt or Pd, X １ is C, X ２ ~X ４ These are C or N, independently of each other. Ring CY ２ and ring CY ３１ and ring CY ３２ and ring CY ４ are, independently of each other, C ５ -C ３０ a carbocyclic group or C １ -C ３０ a heterocyclic group, X １１ is N or C(R １１ ) and X １２ is N or C(R １２ ) and X １３ is N or C(R １３ ) and X ５１ is N or C(R ５１ ) and X ５２ is N or C(R ５２ ) and X ５３ is N or C(R ５３ ) and X ５４ is N or C(R ５４ ) and X ６１ is N or C(R ６１ ) and X ６２ is N or C(R ６２ ) and X ６３ is N or C(R ６３ ) and X ６４ is N or C(R ６４ ) and X ７１ is N or C(R ７１ ) and X ７２ is N or C(R ７２ ) and X ７３ is N or C(R ７３ ) and X ７４ is N or C(R ７４ ) and L １ O, S, Se, N(R) １０１ ), C (R １０１ ) (Caution １０２ ), or Si (R １０１ ) (Caution １０２ ) and L ２ , L ３ and L ４ These are, independently of each other, single bonds, O, S, Se, N(R'), C(R')(R''), or Si(R')(R''), L ２ , L ３ and L ４ At least one of them is, independently of each other, O, S, Se, N(R'), C(R')(R''), or Si(R')(R''), i) Said L ２ If is N(R'), then R' is X ５４ and X ６１ Each of them is not connected, ii) the L ３ If is N(R'), then R' is X ６４ and X ７１ Each of them is not connected, iii) the L ４ If is N(R'), then R' is X ７４ and X １１ They are not connected to each of them, R １１ ~R １３ 、R ２ 、R ３ 、R ４ 、R ５１ ~R ５４ 、R ６１ ~R ６４ 、R ７１ ~R ７４ 、R １０１ 、R １０２ 、R’, and R” are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ５ 、a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C １ -C ６０ an alkyl group, a substituted or unsubstituted C ２ -C ６０ an alkenyl group, a substituted or unsubstituted C ２ -C ６０ an alkynyl group, a substituted or unsubstituted C １ -C ６０ an alkoxy group, a substituted or unsubstituted C １ -C ６０ an alkylthio group, a substituted or unsubstituted C ３ -C １０ a cycloalkyl group, a substituted or unsubstituted C １ -C １０ a heterocycloalkyl group, a substituted or unsubstituted C ３ -C １０ a cycloalkenyl group, a substituted or unsubstituted C １ -C １０ a heterocycloalkenyl group, a substituted or unsubstituted C ６ -C ６０ an aryl group, a substituted or unsubstituted C ６ -C ６０ an aryloxy group, a substituted or unsubstituted C ６ -C ６０ an arylthio group, a substituted or unsubstituted C １ -C ６０ a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic hetero-condensed polycyclic group, -N(Q １ ) (Q ２ ), -Si(Q ３ ) (Q ４ ) (Q ５ ), -Ge(Q ３ ) (Q ４ ) (Q ５ ), -B (Q ６ ) (Q ７ ), or -P (=O) (Q ８ ) (Q ９ ) and a2 to a4 are mutually independent integers between 0 and 20. i) R １１ ~R １３ ii) Two or more of the following R ２ Two or more of the above, iii) Multiple R ３ Two or more of the above, iv) Multiple R ４ Two or more of the following, v) R ５１ ~R ５４ Two or more of the above, vi) R ６１ ~R ６４ Two or more of the above, vii)R ７１ ~R ７４ Two or more of the above, viiii)R １０１ and R １０２ , and ix) Each of R' and R'' is optionally connected to each other, and at least one R １０ａ Substitute or non-substitute C ５ -C ３０ A carbon ring group, or at least one R １０ａ Substitute or non-substitute C １ -C ３０ It can form a heterocyclic group, The aforementioned R １０ａ The explanation relating to the above R １１ This is similar to the explanation regarding the above, The substituted C １ -C ６０ Alkyl alkyl group, substituted C ２ -C ６０ Alkenyl group, substituted C ２ -C ６０ Alkynyl group, substituted C １ -C ６０ Alkoxy group, substituted C １ -C ６０ Alkylthio group, substituted C ３ -C １０ Cycloalkyl groups, substituted C １ -C １０ Heterocycloalkyl groups, substituted C ３ -C １０ Cycloalkenyl group, substituted C １ -C １０ heterocycloalkenyl group, substituted C ６ -C ６０ Aryl group, substituted carbon ６ -C ６０ Aryloxy group, substituted C ６ -C ６０ Arylthio group, substituted C １ -C ６０ The substituents of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic heterocondensed polycyclic group are Deuterium, -F, -Cl, -Br, -I, -CD ３ , -CD ２ H, -CDH ２ , -CF ３ , -CF ２ H, -CFH ２ hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C １ -C ６０ alkyl group, C ２ -C ６０ Alkenyl group, C ２ -C ６０ Alkynyl group, C １ -C ６０ Alkoxy group, or C １ -C ６０ Alkylthio group; Deuterium, -F, -Cl, -Br, -I, -CD ３ , -CD ２ H, -CDH ２ , -CF ３ , -CF ２ H, -CFH ２ hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C ３ -C １０ Cycloalkyl groups, C １ -C １０ Heterocycloalkyl groups, C ３ -C １０ Cycloalkenyl group, C １ -C １０ Heterocycloalkenyl group, C ６ -C ６０ Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ Arylthio group, C １ -C ６０ Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q １１ ) (Q １２ ), -Si(Q １３ ) (Q １４ ) (Q １５ ), -Ge(Q １３ ) (Q １４ ) (Q １５ ), -B (Q １６ ) (Q １７ ), -P(=O)(Q １８ ) (Q １９ C, replaced by any combination thereof. １ -C ６０ alkyl group, C ２ -C ６０ Alkenyl group, C ２ -C ６０ Alkynyl group, C １ -C ６０ Alkoxy group, or C １ -C ６０ Alkylthio group; Deuterium, -F, -Cl, -Br, -I, -CD ３ , -CD ２ H, -CDH ２ , -CF ３ , -CF ２ H, -CFH ２ hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C １ -C ６０ alkyl group, C ２ -C ６０ Alkenyl group, C ２ -C ６０ Alkynyl group, C １ -C ６０ Alkoxy group, C １ -C ６０ Alkylthio group, C ３ -C １０ Cycloalkyl groups, C １ -C １０ Heterocycloalkyl groups, C ３ -C １０ Cycloalkenyl group, C １ -C １０ Heterocycloalkenyl group, C ６ -C ６０ Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ Arylthio group, C １ -C ６０ Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q ２１ ) (Q ２２ ), -Si(Q ２３ ) (Q ２４ ) (Q ２５ ), -Ge(Q ２３ ) (Q ２４ ) (Q ２５ ), -B (Q ２６ ) (Q ２７ ), -P(=O)(Q ２８ ) (Q ２９ ), or any combination thereof, C ３ -C １０ Cycloalkyl groups, C １ -C １０ Heterocycloalkyl groups, C ３ -C １０ Cycloalkenyl group, C １ -C １０ Heterocycloalkenyl group, C ６ -C ６０ Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ Arylthio group, C １ -C ６０ Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, or monovalent non-aromatic heterocondensed polycyclic groups; -N(Q) ３１ ) (Q ３２ ), -Si(Q ３３ ) (Q ３４ ) (Q ３５ ), -Ge(Q ３３ ) (Q ３４ ) (Q ３５ ), -B (Q ３６ ) (Q ３７ ), or -P (=O) (Q ３８ ) (Q ３９ );or Any combination of those; The aforementioned Q １ ~Q ９ Q １１ ~Q １９ Q ２１ ~Q ２９ and Q ３１ ~Q ３９ They are independent of each other, Hydrogen, deuterium, or -F; or Deuterium, -F, cyano group, C １ -C ６０ alkyl group, C ６ -C ６０ A C that is substituted or unsubstituted with an aryl group, or any combination thereof. １ -C ６０ alkyl group, C ２ -C ６０ Alkenyl group, C ２ -C ６０ Alkynyl group, C １ -C ６０ Alkoxy group, C １ -C ６０ Alkylthio group, C ３ -C １０ Cycloalkyl groups, C １ -C １０ Heterocycloalkyl groups, C ３ -C １０ Cycloalkenyl group, C １ -C １０ Heterocycloalkenyl group, C ６ -C ６０ Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ Arylthio group, C １ -C ６０ Organometallic compounds that are heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, or monovalent non-aromatic heterocondensed polycyclic groups.

2. The aforementioned X ２ and X ３ Each of them is C, and X ４ The organometallic compound according to claim 1, wherein is N.

3. The aforementioned ring CY ２ , Tamaki CY ３１ and CY ３２ These are, independently of each other, a benzene group, a naphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, or a benzoisoquinoline group. The aforementioned ring CY ４ The organometallic compound according to claim 1, wherein is a pyridine group, pyrimidine group, pyridazine group, pyrazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, or benzoisoquinoline group.

4. L ２ , L ３ and L ４ The organometallic compound according to claim 1, wherein at least one of them is N(R').

5. L ２ , L ３ and L ４ The organometallic compound according to claim 1, wherein at least one of them is independently O, S, or Se.

6. L ２ , L ３ and L ４ The organometallic compound according to claim 1, wherein at least one of them is independently C(R')(R'') or Si(R')(R'').

7. i) L ２ and L ３ Each of them is a single bond, L ４ is O, S, Se, N(R'), C(R')(R''), or Si(R')(R''), ii) L ２ and L ４ Each of them is a single bond, L ３ is O, S, Se, N(R'), C(R')(R''), or Si(R')(R''), or iii) L ３ and L ４ Each of them is a single bond, L ２ The organometallic compound according to claim 1, wherein is O, S, Se, N(R'), C(R')(R''), or Si(R')(R'').

8. The aforementioned R １１ ~R １３ , R ２ , R ３ , R ４ , R ５１ ~R ５４ , R ６１ ~R ６４ , R ７１ ~R ７４ , R １０１ , R １０２ R' and R'' are independent of each other. Hydrogen, deuterium, -F, or cyano group; Deuterium, -F, cyano group, or any combination thereof, or unsubstituted or unsubstituted C １ -C ２０ alkyl group; Deuterium, -F, cyano group, C １ -C ２０ Alkyl alkyl groups, deuterated C １ -C ２０ Alkyl alkyl groups, C fluoride １ -C ２０ alkyl group, C ３ -C １０ Cycloalkyl groups, deuterated C ３ -C １０ Cycloalkyl groups, C fluoride ３ -C １０ Cycloalkyl groups, (C １ -C ２０ Alkyl) C ３ -C １０ Cycloalkyl group, phenyl group, deuterated phenyl group, fluorinated phenyl group, (C １ -C ２０ Alkyl)phenyl group, naphthyl group, pyridinyl group, furanyl group, thiophenyl group, benzofuranyl group, benzothiophenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, -Si(Q ３３ ) (Q ３４ ) (Q ３５ ), -Ge(Q ３３ ) (Q ３４ ) (Q ３５ ), or any combination thereof, C ３ -C １０ Cycloalkyl groups, phenyl groups, naphthyl groups, pyridinyl groups, furanyl groups, thiophenyl groups, benzofuranyl groups, benzothiophenyl groups, carbazolyl groups, dibenzofuranyl groups, or dibenzothiophenyl groups; or -Si(Q) ３ ) (Q ４ ) (Q ５ ) or -Ge(Q ３ ) (Q ４ ) (Q ５ The organometallic compound according to claim 1, wherein the organometallic compound is as described in claim 1.

9. The organometallic compound according to claim 1, comprising deuterium, a tert-butyl group substituted or unsubstituted with at least one deuterium, or any combination thereof.

10. An organometallic compound according to claim 1, represented by the following chemical formula 1-1: 【Chemistry 2】 In the above chemical formula 1-1, M, X １ ~X ４ , X １１ ~X １３ , X ５１ ~X ５４ , X ６１ ~X ６４ , X ７１ ~X ７４ and L １ ~L ４ The explanations relating to each of these are the same as those described in claim 1. X ２１ is N or C(R ２１ ) and X ２２ is N or C(R ２２ ) and X ２３ is N or C(R ２３ ) and R ２１ ~R ２３ The explanation for each of these is as stated in Claim 1, R ２ This is similar to the explanation regarding the above, X ３１ is N or C(R ３１ ) and X ３２ is N or C(R ３２ ) and X ３３ is N or C(R ３３ ) and X ３４ is N or C(R ３４ ) and X ３５ is N or C(R ３５ ) and X ３６ is N or C(R ３６ ) and R ３１ ~R ３６ The explanation for each of these is as stated in Claim 1, R ３ This is similar to the explanation regarding the above, X ４１ is N or C(R ４１ ) and X ４２ is N or C(R ４２ ) and X ４３ is N or C(R ４３ ) and X ４４ is N or C(R ４４ ) and R ４１ ~R ４４ The explanation for each of these is as stated in Claim 1, R ４ This is similar to the explanation regarding the above, i) R １１ ~R １３ Two or more of the above, ii) R ２１ ~R ２３ Two or more of the above, iii)R ３１ ~R ３６ Two or more of the above, and iv) R ４１ ~R ４４ Each of two or more of these is optionally connected to one R １０ａ Substitute or non-substitute C ５ -C ３０ A carbon ring group, or at least one R １０ａ Substitute or non-substitute C １ -C ３０ It can form a heterocyclic group, The aforementioned R １０ａ The explanation relating to the above R １１ The organometallic compound according to claim 1, which is similar to the description relating thereto.

11. First electrode and The second electrode and Displaced between the first electrode and the second electrode, the intermediate layer includes a light-emitting layer, The aforementioned intermediate layer comprises one or more organometallic compounds as described in any one of claims 1 to 10, wherein the light-emitting element is a light-emitting element.

12. The light-emitting element according to claim 11, wherein the organometallic compound is contained in the light-emitting layer.

13. The light-emitting element according to claim 12, wherein the light emitted from the light-emitting layer is blue light.

14. The light-emitting element according to claim 12, wherein the CIEy value of the light emitted from the light-emitting layer is 0.040 to 0.

170.

15. The light-emitting element according to claim 12, wherein the emission peak wavelength of the light emitted from the light-emitting layer is 440 nm to 470 nm.

16. The light-emitting element according to claim 12, wherein the organometallic compound contained in the light-emitting layer is an emitter.

17. The organometallic compound contained in the light-emitting layer is a sensorizer. The light-emitting layer further includes an emitter, The light-emitting element according to claim 12, wherein the emitter and the organometallic compound are different from each other.

18. The light-emitting element according to claim 17, wherein the emitter is a prompt fluorescent compound or a delayed fluorescent compound.

19. The light-emitting element according to claim 17, wherein the emitter is a multi-resonance thermally activated delayed fluorescence compound.

20. An electronic device comprising a light-emitting element as described in claim 11.

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