Organometallic compounds and organic light-emitting devices including such organometallic compounds

Abstract

An organometallic compound and an organic light-emitting device comprising the same are provided. The organometallic compound is represented by Formula 1. In Formula 1, the groups are the same as those described in the detailed description currently disclosed. Formula 1

Description

[0001] This application claims priority and benefit to Korean Patent Application No. 10-2020-0050349, filed on April 24, 2020, with the Korean Intellectual Property Office, the entire disclosure of which is incorporated herein by reference. Technical Field

[0002] One or more embodiments relate to an organometallic compound and an organic light-emitting device comprising the organometallic compound. Background Technology

[0003] Compared to suitable devices in the prior art, organic light-emitting devices (OLEDs) are self-emitting devices that produce full-color images and also have relatively wide viewing angles, high contrast, short response times, and / or superior characteristics in terms of brightness, driving voltage, and / or response speed.

[0004] Examples of organic light-emitting devices may include a first electrode disposed on a substrate and a hole transport region, an emitter layer, an electron transport region, and a second electrode sequentially disposed on the first electrode. Holes supplied from the first electrode can migrate to the emitter layer through the hole transport region, and electrons supplied from the second electrode can migrate to the emitter layer through the electron transport region. Charge carriers (such as holes and electrons) recombine in the emitter layer to generate excitons. These excitons transition from an excited state to a ground state, thereby producing light. Summary of the Invention

[0005] An aspect according to one or more embodiments relates to a novel organometallic compound and an organic light-emitting device comprising the organometallic compound.

[0006] Other aspects will be set forth in part in the description which follows, and in part will be apparent from the description or may be learned by practice of the disclosed embodiments given.

[0007] According to embodiments of this disclosure, an organometallic compound is represented by Formula 1.

[0008] Formula 1

[0009]

[0010] In Equation 1,

[0011] M is selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm).

[0012] Y1 to Y3 are each independently N or C.

[0013] T1 to T4 are all independently chemical bonds, of the following types: O, S, B(R'), N(R'), P(R'), C(R')(R"), Si(R')(R"), Ge(R')(R"), C(=O), B(R')(R"), N(R')(R"), or P(R')(R"). Specifically, when T1 is a chemical bond, Y1 and M are directly bonded; when T2 is a chemical bond, Y2 and M are directly bonded; when T3 is a chemical bond, Y3 and M are directly bonded; and when T4 is a chemical bond, A4 and M are directly bonded.

[0014] In the bonds between M and Y1 or T1 (i.e., the bond between Y1 and M or the bond between T1 and M), the bonds between M and Y2 or T2 (i.e., the bond between Y2 and M or the bond between T2 and M), the bonds between M and Y3 or T3 (i.e., the bond between Y3 and M or the bond between T3 and M), and the bonds between M and A4 or T4 (i.e., the bond between the carbon atom of A4 and M or the bond between T4 and M), two bonds are coordinate bonds, and the other two bonds are covalent bonds.

[0015] A1 to A3 and A 11 A 12 All were independently selected from C5-C 60 Carbocyclic groups and C1-C 60 Heterocyclic group,

[0016] c11 is either 0 or 1, and when c11 is 0, A 11 It does not exist; that is, the organometallic compounds represented by Formula 1 do not include A. 11 ,

[0017] c12 is either 0 or 1, and when c12 is 0, A 12 It does not exist; that is, the organometallic compounds represented by Formula 1 do not include A. 12 ,

[0018] L1 to L4 are all independently selected from single bonds, double bonds, *-N(R5)-*', *-B(R5)-*', *-P(R5)-*', *-C(R5)(R6)-*', *-Si(R5)(R6)-*', *-Ge(R5)(R6)-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R5)=*', *=C(R5)-*', *-C(R5)=C(R6)-*', *-C(=S)-*', and *-C≡C-*'.

[0019] a1 to a4 are all independent integers from 0 to 3, where when a1 is 0, A1 and A2 are not connected to each other, when a2 is 0, A2 and A3 are not connected to each other, when a3 is 0, A3 and A4 are not connected to each other, and when a4 is 0, A4 and A1 are not connected to each other.

[0020] R', R", R1 to R6, R 11 and R 12 All are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), -P(=S)(Q1)(Q2), =O, =S, =N(Q1) and =C(Q1)(Q2),

[0021] b1 to b3, b11, and b12 are all independent integers from 0 to 20.

[0022] b4 is an integer from 0 to 7.

[0023] In the numbers R', R", and b1, R1; in the numbers b2, R2; in the numbers b3, R3; in the numbers b4, R4; in the numbers b5, R6; and in the numbers b11, R1... 11 And R of b12 numbers 12In this process, adjacent groups can be selectively linked to each other to form substituted or unsubstituted C5-C groups. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group.

[0024] Both * and *' represent bonding sites with adjacent atoms, and

[0025] Replacement C5-C 60 Carbocyclic groups, substituted C1-C 60 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 heteroaryl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 At least one substituent selected from the following: heteroarylsulfonyl, substituted monovalent nonaromatic condensed polycyclic group, and substituted monovalent nonaromatic condensed heterocyclic group.

[0026] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;

[0027] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, and C3-C. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, -Si(Q) 11 (Q)12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 ) and -P(=O)(Q 11 (Q) 12 Choose at least one of the C1-Cs) 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;

[0028] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heterocyclic group;

[0029] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21) and -P(=O)(Q 21 (Q) 22 Choose at least one of the C3-C options. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic condensed heterocyclic; and

[0030] -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 ),

[0031] Among them, Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each group is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic, monovalent non-aromatic condensed heterocyclic, C1-C substituted with at least one of deuterium, -F and cyano. 60 Alkyl groups, substituted with at least one of deuterium, -F, and cyano groups, at a C6-C position. 60 Aryl, biphenyl, and terphenyl.

[0032] According to another embodiment of this disclosure, an organic light-emitting device includes: a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode, the organic layer including an emitting layer, and

[0033] At least one organometallic compound represented by Formula 1. Attached Figure Description

[0034] The above and other aspects, features, and improvements of certain disclosed embodiments will become more apparent from the following description taken in conjunction with the accompanying drawings, in which:

[0035] Figures 1 to 4 These are all schematic diagrams of the structure of organic light-emitting devices according to the corresponding embodiments. Detailed Implementation

[0036] Referring now to the embodiments in more detail, examples of which are illustrated in the accompanying drawings, in which the same reference numerals refer to the same elements throughout. In this respect, the embodiments given may take different forms and should not be construed as limited to the description set forth herein. Therefore, the embodiments are described below only by reference to the accompanying drawings to explain aspects of this specification. As used herein, the term “and / or” includes any and all combinations of one or more of the associated listed items. Throughout this disclosure, the expression “at least one of a, b, and c” means only a, only b, only c, both a and b, both a and c, both b and c, all of a, b, and c, or variations thereof.

[0037] According to embodiments of this disclosure, organometallic compounds are represented by the following formula 1:

[0038] Formula 1

[0039]

[0040] Triple-state metal centers in organometallic compounds ( 3 Energy levels of the triplet metal-centered (MC) state (E) 3MC The charge transfer from the triplet state metal to the ligand in organometallic compounds can be greater than that in other organometallic compounds. 3 MLCT (triple metal-to-ligand charge transfer) state energy level (E 3MLCT ).

[0041] In one or more embodiments, the triplet metal center of the organometallic compound ( 3 Energy levels of the MC state (E) 3MC The concentration can be approximately 0.26 kcal / mol or greater. In one or more embodiments, E 3MCIt can be about 1.0 kcal / mol or less, for example, about 0.26 kcal / mol to about 0.8 kcal / mol.

[0042] When organometallic compounds satisfy E 3MC When the range is reached, organometallic compounds from 3 MLCT state transition to 3 The probability of the MC state (which is a non-emission state) is reduced. Therefore, organometallic compounds can exhibit excellent stability in the excited state, and can improve the efficiency and lifetime of organic light-emitting devices that include organometallic compounds.

[0043] In Formula 1, M is selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm).

[0044] In one embodiment, M may be selected from Pt, Pd, Cu, Ag, Au, Rh, Ir, Ru, and Os.

[0045] In one or more embodiments, M may be Pt, but the embodiments disclosed herein are not limited thereto.

[0046] In Equation 1, Y1 to Y3 are each independently N or C.

[0047] T1 to T4 are all independently chemical bonds, of the following types: O, S, B(R'), N(R'), P(R'), C(R')(R"), Si(R')(R"), Ge(R')(R"), C(=O), B(R')(R"), N(R')(R"), or P(R')(R"). Specifically, when T1 is a chemical bond, Y1 and M are directly bonded; when T2 is a chemical bond, Y2 and M are directly bonded; when T3 is a chemical bond, Y3 and M are directly bonded; and when T4 is a chemical bond, A4 and M are directly bonded.

[0048] In the bonds between M and Y1 or T1 (i.e., the bond between Y1 and M or the bond between T1 and M), the bonds between M and Y2 or T2 (i.e., the bond between Y2 and M or the bond between T2 and M), the bonds between M and Y3 or T3 (i.e., the bond between Y3 and M or the bond between T3 and M), and the bonds between M and A4 or T4 (i.e., the bond between the carbon atom of A4 and M or the bond between T4 and M), two bonds are coordinate bonds, and the other two bonds are covalent bonds.

[0049] In one embodiment, T1 to T4 can be chemical bonds, at least one of the bonds between Y1 and M and between Y2 and M can be coordinate bonds, Y1 can be N, and Y2 can be C.

[0050] In one or more embodiments, Y1 can be N, and Y2 and Y3 can both be C, but the embodiments disclosed herein are not limited thereto.

[0051] In Equation 1, A1 to A3 and A 11 A 12 All were independently selected from C5-C 60 Carbocyclic groups and C1-C 60 Heterocyclic group.

[0052] In one embodiment, A1 to A3 and A 11 A 12 Each can be independently selected from:

[0053] Phenyl group, naphthyl group, anthracene group, phenanthrene group, benzo[9,10]phenanthrene group, pyrene group, Groups, cyclopentyl groups, cyclopentadienyl groups, cyclohexyl groups, cyclohexene groups, 1,2,3,4-tetrahydronaphthyl groups, furan groups, thiophene groups, thiophene groups, indene groups, fluorene groups, indole groups, carbazole groups, benzofuran groups, dibenzofuran groups, benzothiophene groups, dibenzothiophene groups, benzothiophene groups, dibenzothiophene groups, indolepyridine groups, indolepyridine groups, benzofuranpyridine groups, benzothiophenepyridine groups, benzothiophenepyridine groups, indolepyrimidine groups, indolepyrimidine groups, benzofuranpyrimidine groups, benzothiophenepyrimidine groups, benzothiophenepyrimidine groups, dihydropyridine groups, pyridine groups, pyrimidine groups, pyrazine groups, pyridazine groups, triazine groups, quinoline groups, isoquinoline groups, quinoxaline groups, quinazoline groups, phenanthroline groups Pyrrole group, pyrazole group, imidazole group, 2,3-dihydroimidazolium group, triazole group, 1,2,4-triazole group, tetraazole group, 2,3-dihydrotriazole group, azathiorrole group, diazathiorrole group, triazathiorrole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, 2,3-dihydrobenzimidazole group, imidazopyridine group, 2,3-dihydroimidazopyridine group, imidazopyrimidine group, 2,3-dihydroimidazopyrimidine group, imidazopyrazine group, 2,3-dihydroimidazopyrazine group, benzoxazole group, benzothiazole group, benzooxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group and 5,6,7,8-tetrahydroquinoline group.

[0054] In one embodiment, i) A1 may be selected from pyridine groups, pyrimidine groups, pyrazine groups, pyridazine groups, and triazine groups.

[0055] ii) A2 can be selected from indole, carbazole, indolepyridine, and indolepyrimidine groups.

[0056] iii) A3 can be selected from phenyl groups, naphthyl groups, anthracene groups, and phenanthrene groups, or

[0057] It can satisfy any combination of i), ii) and iii).

[0058] In one or more embodiments, A1 may be selected from pyridine, pyrimidine, pyrazine, pyridazine, and triazine groups, and A2 may be selected from indole, carbazole, indole-pyridine, and indole-pyrimidine groups. In one or more embodiments, A1 may be selected from pyridine, pyrimidine, pyrazine, pyridazine, and triazine groups, and A3 may be selected from phenyl, naphthol, anthracene, and phenanthrene groups. In one or more embodiments, A2 may be selected from indole, carbazole, indole-pyridine, and indole-pyrimidine groups, and A3 may be selected from phenyl, naphthol, anthracene, and phenanthrene groups. In one or more embodiments, A1 may be selected from pyridine, pyrimidine, pyrazine, pyridazine, and triazine groups, A2 may be selected from indole, carbazole, indole-pyridine, and indole-pyrimidine groups, and A3 may be selected from phenyl, naphthol, anthracene, and phenanthrene groups.

[0059] In one embodiment, ia)A1 can be a group represented by any one of formulas 2A-1 to 2A-5.

[0060] iia)A2 can be a group represented by any one of formulas 2B-1 to 2B-3,

[0061] iiia) A3 can be a group represented by formula 2C-1, or

[0062] It can satisfy any combination of ia), iia), and iiia):

[0063]

[0064] In equations 2A-1 to 2A-5, equations 2B-1 to 2B-3, and equation 2C-1

[0065] Y 21 For N or C(R) 11a ), Y 22 For N or C(R) 12a ), Y 23 For N or C(R) 13a), Y 24 For N or C(R) 14a ), Y 25 For N or C(R) 15a ), Y 26 For N or C(R) 16a ), Y 27 For N or C(R) 17a ), and Y 28 For N or C(R) 18a ),

[0066] Z 21 For *'-C, C(R) 21a ) or N, and Z 22 For *'-C, C(R) 22a ) or N,

[0067] Z 31 For *'-N or N(R) 31a ),

[0068] R 11a To R 18a R 21a To R 22a and R 31a Each of these is independently identical to the descriptions of R', R" and R1 to R6 described above, for example, R 11a To R 18a R 21a To R 22a and R 31a They can all be independently identical to those described in conjunction with R1 above, and

[0069] * indicates a binding bit with adjacent T1, T2, or T3, and *' indicates a binding bit with adjacent L1, L2, L3, or L4.

[0070] In one or more embodiments, in formulas 2A-1 to 2A-5 and formula 2C-1, Y 22 It can be C(R) 12a ),and

[0071] R 12a It doesn't have to be hydrogen.

[0072] In one or more embodiments, R 12a It can be C1-C 20 Alkyl or substituted with at least one C1-C 20 C1-C of alkyl 20 alkyl.

[0073] In one or more embodiments, in formulas 2A-1 to 2A-5, Y 21 It can be C(R) 11a ), and Y23 It can be C(R) 13a In one or more embodiments, R 11a and R 13a Both can be hydrogen.

[0074] In one or more embodiments, in formulas 2A-1 to 2A-5, Z 21 It can be C(R) 21a ), and Z 22 It can be *'-C. In one or more embodiments, R 21a It can be hydrogen.

[0075] In one or more embodiments, in formulas 2B-1 to 2B-3, Y 21 It can be C(R) 11a ), Y 22 It can be C(R) 12a ), Y 23 It can be C(R) 13a ), Y 24 It can be C(R) 14a ), Y 25 It can be C(R) 15a ), Y 26 It can be C(R) 16a ), Y 27 It can be C(R) 17a ), and Y 28 It can be C(R) 18a In one or more embodiments, R 11a To R 18a It can be hydrogen.

[0076] In one or more embodiments, in formulas 2B-1 to 2B-3, Z 21 It can be *'-C, and Z 31 It can be *'-N.

[0077] In one or more embodiments, in formula 2C-1, Y 21 It can be (R) 11a ), and Y 23 It can be C(R) 13a In one or more embodiments, R 11a and R 13a Both can be hydrogen.

[0078] In one or more embodiments, in formula 2C-1, Z 21 It can be *'-C, and Z 22 It can be *'-C.

[0079] In one or more embodiments, A1 may be a group represented by any one of Formulas 2A-1 to 2A-5, and A2 may be a group represented by any one of Formulas 2B-1 to 2B-3. In one or more embodiments, A1 may be a group represented by any one of Formulas 2A-1 to 2A-5, and A3 may be a group represented by Formula 2C-1. In one or more embodiments, A2 may be a group represented by any one of Formulas 2B-1 to 2B-3, and A3 may be a group represented by Formula 2C-1. In one or more embodiments, A1 may be a group represented by any one of Formulas 2A-1 to 2A-5, A2 may be a group represented by any one of Formulas 2B-1 to 2B-3, and A3 may be a group represented by Formula 2C-1.

[0080] In one embodiment, the sum of c11 and c12 can be 1 or 2.

[0081] In one or more embodiments, c11 can be 1.

[0082] In Equation 1, L1 to L4 are all independently selected from single bonds, double bonds, *-N(R5)-*', *-B(R5)-*', *-P(R5)-*', *-C(R5)(R6)-*', *-Si(R5)(R6)-*', *-Ge(R5)(R6)-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R5)=*', *=C(R5)-*', *-C(R5)=C(R6)-*', *-C(=S)-*', and *-C≡C-*', and * and *' both represent bonding sites with adjacent atoms.

[0083] In one embodiment, L1 to L4 can each be an independent single bond or *-O-*'.

[0084] In Equation 1, a1 to a4 are all independent integers from 0 to 3. When a1 is 0, A1 and A2 are not connected to each other. When a2 is 0, A2 and A3 are not connected to each other. When a3 is 0, A3 and A4 are not connected to each other. And when a4 is 0, A4 and A1 are not connected to each other.

[0085] In one embodiment, a1 to a3 can all be 1, a4 can be 0, L1 and L3 can both be single bonds, and L2 can be *-O-*'.

[0086] In Equation 1, R', R", R1 to R6, R 11 and R 12Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2),

[0087] b1 to b3, b11, and b12 can each be an integer from 0 to 20 independently.

[0088] b4 can be an integer from 0 to 7, and

[0089] In the numbers R', R", and b1, R1; in the numbers b2, R2; in the numbers b3, R3; in the numbers b4, R4; in the numbers b5, R6; and in the numbers b11, R1... 11 And R of b12 numbers 12 In this process, adjacent groups can be selectively linked to each other to form substituted or unsubstituted C5-C groups. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group.

[0090] In one embodiment, R', R", R1 to R6, R 11 and R 12 Each group can be independently selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C20 Alkyl and C1-C 20 Alkoxy;

[0091] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 At least one of the alkoxy groups selected from the C1-C 20 Alkyl and C1-C 20 Alkoxy;

[0092] Cyclopentyl, cyclohexyl, phenyl, naphthyl, pyridyl, pyrazinyl, pyridazinyl, pyrroleyl, indolyl, isoindolyl, indazoleyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, cyclolinyl, and triazinyl;

[0093] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, indoleyl, isoindoleyl, indazoleyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, triazinyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 The cyclopentyl, cyclohexyl, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, indolyl, isoindolyl, indazole, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, cyclolinyl, and triazinyl groups selected from at least one of the following:

[0094] Cyclopentyl, cyclohexyl, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, indoleyl, isoindoleyl, indazoleyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, and triazinyl groups, all substituted with at least one of the following groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, cyclopentyl, cyclohexyl, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, indoleyl, isoindoleyl, indazoleyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, triazinyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 Choose at least one of the C1-Cs) 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, indoleyl, isoindoleyl, indazoleyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, cenolinyl, and triazinyl; and

[0095] -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), -P(=S)(Q1)(Q2), =O, =S, =N(Q1) and =C(Q1)(Q2),

[0096] Among them, Q1 to Q3 and Q 31 To Q 33 Each can be independently selected from:

[0097] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl group, C1-C 20 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 20 Aryl, C1-C 20 Heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic condensed heterocyclic.

[0098] In one embodiment, the organometallic compound represented by Formula 1 may be an organometallic compound selected from Formulas 1-1 to 1-10:

[0099]

[0100]

[0101] In equations 1-1 to 1-10,

[0102] M, A1 to A3, A 11 A 12 Y1 to Y3, L1 to L3, a1 to a3, R1 to R4, R 11 and R 12 b1 to b3, b11 and b12 are all independently identical to those described above.

[0103] X 11 To X 13 Each is independently selected from O, S, N(R) 21 ), C(R 21 (R) 22 ), C(=O), C(=S), C(=NR 21 ) and C(=C(R) 21 (R) 22 )),

[0104] X 21 To X 23 Each is independently N or C(R) 21 ),and

[0105] R 21 and R 22 Each of these is independently combined with the aforementioned R', R", R1 to R6, R 11 and R 12 The descriptions are the same, for example, R 21 and R 22 They can all be independently identical to those described in conjunction with R1 above.

[0106] In one or more embodiments, in Equations 1-7, X 11 It can be C(R) 21 (R) 22 ) or C (=O). In one or more embodiments, R 21 and R 22 They can all be independently selected from hydrogen, C1-C 20 Alkyl and C6-C 20 Aryl.

[0107] In one or more embodiments, in formulas 1-10, X 21 and X 23 Both can be C(R) 21 ), and A 11 and A 12 All of them can be cyclopentyl groups.

[0108] In one or more embodiments, R4 can be C1-C 20 Alkyl or C6-C 20 Aryl groups, or both selected from C1-C groups substituted with at least one deuterium. 20 Alkyl groups and substituted C6-C groups having at least one deuterium 20 At least one of the aryl groups is substituted by C1-C 20 Alkyl or C6-C 20 Aryl.

[0109] In one embodiment, the organometallic compound represented by Formula 1 can be an organometallic compound represented by Formula 1A:

[0110]

[0111] In Equation 1A,

[0112] M, A1, A3, A 11 A 12 , Y1, Y3, L2 to L3, R1, R3, R4, R 11 R 12 b1, b3, b4, b11, b12, c11, and c12 are all independently identical to those described above.

[0113] X 31 To X 32 Each is independently N or C(R) 32 ),

[0114] A 31 Combined with A1 to A3 and A 11 A 12 The descriptions are the same, for example, A 31 It can be the same as the description in combination with A1.

[0115] b31 is the same as that described in combination with b2, and

[0116] R 4a R 31 and R 32 Each of them independently binds to R', R", R1 to R6, R 11 and R 12 The descriptions are the same, for example, R 4a R 31 and R 32 They can all be independently described as identical to those in combination with R1.

[0117] In one embodiment, the organometallic compound represented by Formula 1 may be selected from compounds 1 to 12, but the embodiments of this disclosure are not limited thereto:

[0118]

[0119] Because the organometallic compound represented by Formula 1 includes six forming atoms of a carbene ligand bonded to the central metal (M in Formula 1), the binding force between the central metal and the carbene ligand can be enhanced, thereby increasing rigidity. Therefore, the lifetime characteristics of organic light-emitting devices incorporating organometallic compounds can be improved.

[0120] In detail, since the organometallic compounds represented by Formula 1 include carbene ligands with condensed cyclic structures, the stability of devices including organometallic compounds can be improved due to the principle that MLCT increases with increasing σ binding force.

[0121] Furthermore, in the organometallic compounds represented by Formula 1, the atom bonded to the central metal of the condensed cyclic ligands of 5-membered and 6-membered rings is carbon. The carbon and the central metal are not coordinated but covalently bonded, which increases the bonding force. Therefore, devices incorporating organometallic compounds can have long lifespans.

[0122] As a result, when organometallic compounds are applied to (or used in) organic light-emitting devices, the triplet exciton transition caused by ligand breakage can be prevented or reduced. 3 The MC state (which is a non-luminescent state). Therefore, in organic light-emitting devices including organometallic compounds represented by Formula 1, the stability, lifetime, and efficiency in the excited state can all be excellent.

[0123] In addition, in one embodiment, the organometallic compound represented by Formula 1 can satisfy the above-mentioned E. 3MC The range. In this case, the organometallic compound represented by Formula 1 is from 3 MCLC state transition to 3 The reduced likelihood of the MC state (which is a non-emission state) allows for excellent stability in the excited state and can improve the efficiency and lifetime of organic light-emitting devices, including those using organometallic compounds.

[0124] Organometallic compounds can emit blue light. In one or more embodiments, the organometallic compound can emit blue light (bottom emission CIE) with a maximum emission wavelength of about 450 nm or greater and about 510 nm or less. x,y The color coordinates are X = 0.13, Y = 0.05 to 0.20, but the embodiments of this disclosure are not limited thereto. Therefore, the organometallic compound represented by Formula 1 can be used to manufacture organic light-emitting devices that emit blue light.

[0125] By referring to the examples provided below, those skilled in the art can recognize the method for synthesizing organometallic compounds represented by Formula 1.

[0126] At least one of the organometallic compounds represented by Formula 1 can be used between a pair of electrodes of an organic light-emitting device. In one or more embodiments, the organometallic compound can be included in an emission layer. The organometallic compound included in the emission layer can act as a dopant. In one or more embodiments, the organometallic compound represented by Formula 1 can be used as a material for a capping layer located outside the pair of electrodes of the organic light-emitting device.

[0127] Therefore, an organic light-emitting device is provided, the organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; an organic layer located between the first electrode and the second electrode, the organic layer comprising an emitting layer; and at least one organometallic compound represented by Formula 1.

[0128] The expression “(organic layer) comprises at least one organometallic compound” as used herein can include cases where “(organic layer) comprises the same organometallic compound represented by Formula 1” and cases where “(organic layer) comprises two or more different organometallic compounds, all represented by Formula 1”.

[0129] In one or more embodiments, the organic layer may include only compound 1 as an organometallic compound. In this respect, compound 1 may be present in the emitting layer of the organic light-emitting device. In one or more embodiments, the organic layer may include both compound 1 and compound 2 as organometallic compounds. In this respect, compound 1 and compound 2 may be present in the same layer (e.g., both compound 1 and compound 2 may be present in the emitting layer) or in different layers (e.g., compound 1 may be present in the emitting layer, and compound 2 may be present in the electron transport region).

[0130] In one embodiment,

[0131] The first electrode of an organic light-emitting device can be the anode.

[0132] The second electrode of an organic light-emitting device can be a cathode.

[0133] The organic layer may further include a hole transport region located between the first electrode and the emitter layer, and an electron transport region located between the emitter layer and the second electrode.

[0134] The hole transport region may include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof, and

[0135] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0136] As used herein, the term "organic layer" refers to a single layer and / or multiple layers located between the first and second electrodes of an organic light-emitting device. Materials included in the "organic layer" are not limited to organic materials.

[0137] In one embodiment, the emitter layer comprises an organometallic compound represented by Formula 1, and the emitter layer further comprises a host. The amount of the host in the emitter layer may be greater than the amount of the organometallic compound in the emitter layer.

[0138] In one or more embodiments, the emitter layer further includes a body, and the amount of the organometallic compound may be from about 0.1 parts by weight to about 50 parts by weight, based on 100 parts by weight of the emitter layer.

[0139] In one embodiment, the hole transport region may include a p-dopant having a lowest unoccupied molecular orbital (LUMO) energy level of less than about -3.5 eV.

[0140] [ Figure 1 [Description]

[0141] Figure 1 This is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment of the present disclosure. The organic light-emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.

[0142] In the following text, we will combine Figure 1 The structure of the organic light-emitting device 10 according to the embodiments and the method of manufacturing the organic light-emitting device 10 are described below.

[0143] [First Electrode 110]

[0144] exist Figure 1 Alternatively, a substrate can be disposed below the first electrode 110 or above the second electrode 190. The substrate can be a glass substrate or a plastic substrate, both of which possess excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

[0145] The first electrode 110 can be formed, for example, by depositing or sputtering a material for forming the first electrode 110 onto a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 can be selected from materials with high work function to facilitate hole injection.

[0146] The first electrode 110 can be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof, but the embodiments of this disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transparent electrode or a reflective electrode, the material used to form the first electrode 110 can be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but the embodiments of this disclosure are not limited thereto.

[0147] The first electrode 110 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited to this.

[0148] [Organic layer 150]

[0149] Organic layer 150 is positioned on first electrode 110. Organic layer 150 includes an emission layer.

[0150] The organic layer 150 may also include a hole transport region located between the first electrode 110 and the emitter layer and an electron transport region located between the emitter layer and the second electrode 190.

[0151] [Hole transport region in organic layer 150]

[0152] The hole transport region may have: i) a single-layer structure comprising a single layer containing a single material (e.g., composed of a single material); ii) a single-layer structure comprising a single layer containing multiple different materials (e.g., composed of multiple different materials); or iii) a multi-layer structure having multiple layers comprising multiple different materials (e.g., composed of multiple different materials).

[0153] The hole transport region may include at least one layer selected from a hole injection layer, a hole transport layer, an emission assist layer, and an electron blocking layer.

[0154] In one or more embodiments, the hole transport region may have a single-layer structure or a multi-layer structure. The single-layer structure includes a single layer comprising a variety of different materials (e.g., composed of a variety of different materials). The multi-layer structure has a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure. For each structure, the layers are sequentially stacked from the first electrode 110 in the order stated in the corresponding statement, but the embodiments of this disclosure are not limited thereto.

[0155] The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), compounds represented by Formula 201, and compounds represented by Formula 202:

[0156]

[0157]

[0158] In equations 201 and 202,

[0159] L 201 To L 204 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hypoaryl, substituted or unsubstituted divalent nonaromatic condensed polycyclic groups, and substituted or unsubstituted divalent nonaromatic condensed heterocyclic groups.

[0160] L 205 It can be selected from *-O-*', *-S-*', *-N(Q) 201 )-*', substituted or unsubstituted C1-C20 Alkylene, substituted or unsubstituted C2-C 20 alkenyl, substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hypoaryl, substituted or unsubstituted divalent nonaromatic condensed polycyclic groups, and substituted or unsubstituted divalent nonaromatic condensed heterocyclic groups.

[0161] xa1 to xa4 can each be an independent integer from 0 to 3.

[0162] xa5 can be an integer from 1 to 10, and

[0163] R 201 To R 204 and Q 201 Each can be independently selected from substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, and substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups.

[0164] In one or more embodiments, in formula 202, R 201 and R 202 They can be optionally linked to each other via single bonds, dimethyl-methylene, or diphenyl-methylene, and R 203 and R 204 They can be optionally linked to each other via single bonds, dimethyl-methylene, or diphenyl-methylene.

[0165] In one embodiment, in equations 201 and 202,

[0166] L 201 To L 205 Each can be independently selected from:

[0167] Phenylidene, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptadienyl, adafenyl, acenaphthene, fluorene, spirodifluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenenyl, anthracene, fluorenyl, benzo[9,10]phenenyl, pyrene, phenylene alkyl, benzotetraphenyl, purylene, perylene, pentaphenylene, benzohexaphenylene, benzopentaphenylene, benzobenzyl, benzoylene, oleophylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoydinolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzothiopheneyl, and pyridylene; and

[0168] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10 Alkyl phenyl, substituted -F phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, pyrene alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 The following are selected from at least one of the following: phenylene, cyclopentadienylene, indenylene, naphthylene, chamomilecycloylene, heptadienylene, adaninylene, fluoreneylene, spirodifluoreneylene, benzo[9,10]fluoreneylene, dibenzo[9,10]fluoreneylene, phenanthroline, anthraceneylene, fluoranthroline, benzo[9,10]phenanthroline, pyreneylene, etc. alkyl, tetraphenyl, arbutinyl, perylene, pentaphenyl, hexaphenyl, pentaphenyl, rubidinyl, benzoyl, oleophyl, thiopheneyl, furanyl, carbazolyl, indoleyl, isoydinolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophene, and pyridylyl.

[0169] Among them, Q31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0170] In one or more embodiments, xa1 to xa4 can each be independently 0, 1 or 2.

[0171] In one or more embodiments, xa5 can be 1, 2, 3 or 4.

[0172] In one or more embodiments, R 201 To R 204 and Q 201 All of these can be independently selected from: phenyl, biphenyl, terphenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptadienyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthryl, pyrene, alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoydinoleyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiophenyl, and pyridyl; and

[0173] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10 Alkyl phenyl, substituted -F phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, pyrene alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32The following are selected from at least one of the following: phenyl, biphenyl, terphenyl, cyclopentadienyl, indole, naphthyl, chamomilecycloyl, heptalenyl, indoleyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, pyrene, alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiopheneyl, and pyridyl.

[0174] Among them, Q 31 To Q 33 Each can be independently identical to the description above.

[0175] In one or more embodiments, R from formula 201 201 To R 203 At least one of the selected items can be independently selected from:

[0176] Fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl; and

[0177] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10 The alkyl group of phenyl, the phenyl group substituted with -F, naphthyl, fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl and dibenzothiopheneyl are selected from at least one of the following: fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl and dibenzothiopheneyl.

[0178] However, the embodiments disclosed herein are not limited thereto.

[0179] In one or more embodiments, in formula 202, i)R 201 and R 202 They can be connected to each other via a single key, and / or ii)R 203 and R 204 They can be connected to each other via a single key.

[0180] In one or more embodiments, R in formula 202 201 To R 204 At least one of them can be selected from:

[0181] Carbazolyl; and

[0182] Substitutions include deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10 The carbazoyl group selected from at least one of the following: alkyl phenyl, phenyl substituted with -F, naphthyl, fluorenyl, spirodifluorenyl, carbazoyl, dibenzofuranyl, and dibenzothiopheneyl.

[0183] However, the embodiments disclosed herein are not limited thereto.

[0184] In one or more embodiments, the compound represented by formula 201 can be represented by the following formula 201A:

[0185]

[0186] In one or more embodiments, the compound represented by formula 201 may be represented by the following formula 201A(1), but the embodiments of this disclosure are not limited thereto:

[0187] Formula 201A(1)

[0188]

[0189] In one or more embodiments, the compound represented by formula 201 may be represented by the following formula 201A-1, but the embodiments of this disclosure are not limited thereto:

[0190] Formula 201A-1

[0191]

[0192] In one or more embodiments, the compound represented by formula 202 can be represented by the following formula 202A:

[0193] Formula 202A

[0194]

[0195] In one or more embodiments, the compound represented by formula 202 can be represented by the following formula 202A-1:

[0196]

[0197] In Equations 201A, 201A(1), 201A-1, 202A, and 202A-1,

[0198] L 201 To L 203xa1 to xa3, xa5 and R 202 To R 204 It can be the same as described above.

[0199] R 211 and R 212 They can all independently bind with R 203 The descriptions are the same, and

[0200] R 213 To R 217 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10 Alkyl phenyl, substituted -F phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, pyrene alkyl, tetraphenyl, furanyl, perylene, pentyranyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thiophenyl, furanyl, carbazoyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, dibenzothiophenyl, and pyridyl.

[0201] The hole transport region may include at least one compound selected from compounds HT1 to HT39, but the compounds included in the hole transport region are not limited to these:

[0202]

[0203]

[0204]

[0205] The thickness of the hole transport region can be approximately to approximately (For example, about to approximately Within the range of ), when the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer can be approximately to approximately (For example, about to approximately Within the range of ), and the thickness of the hole transport layer can be approximately to approximately (For example, about to approximately Within these ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage when the thickness of the hole transport region, the thickness of the hole injection layer, and the thickness of the hole transport layer are all within these ranges.

[0206] The emission assist layer can improve luminous efficiency by compensating for the optical resonant distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block the flow of electrons from the electron transport region. The emission assist layer and the electron blocking layer can comprise the materials described above.

[0207] [p-doped]

[0208] In addition to these materials, the hole transport region may also include charge-generating materials to improve conductivity. The charge-generating materials may be uniformly or non-uniformly dispersed within the hole transport region.

[0209] The charge-generating material can be, for example, a p-doped agent.

[0210] In one embodiment, the p-doped agent may have a LUMO level of -3.5 eV or less.

[0211] p-dopers may include at least one selected from quinone derivatives, metal oxides, and cyano-containing compounds, but the embodiments of this disclosure are not limited thereto.

[0212] In one embodiment, the p-doper may include at least one selected from the following compounds:

[0213] Quinone derivatives, such as tetracyanoquinone dimethyl ether (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl ether (F4-TCNQ);

[0214] Metal oxides, such as tungsten oxide and / or molybdenum oxide;

[0215] 1,4,5,8,9,12-hexaazabenzophenanthrene-hexanitrile (HAT-CN); and

[0216] The compound represented by the following formula 221,

[0217] However, the embodiments disclosed herein are not limited thereto:

[0218]

[0219]

[0220] In Equation 221,

[0221] R 221 To R223 Each can be independently selected from substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, and substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, and from R 221 To R 223 At least one of the selected groups may have a C1-C group substituted with cyano, -F, -Cl, -Br, -I, or -F. 20 Alkyl groups, C1-C substituted with -Cl 20 Alkyl groups, C1-C substituted with -Br 20 Alkyl groups and substituted C1-C groups with -I 20 At least one substituent selected from alkyl groups.

[0222] [Emitting layer in organic layer 150]

[0223] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emitting layer can be patterned as a red emitting layer, a green emitting layer, or a blue emitting layer according to the sub-pixels. In one or more embodiments, the emitting layer may have a stacked structure of two or more layers selected from red, green, and blue emitting layers, wherein the two or more layers may be in contact with each other or may be separated from each other. In one or more embodiments, the emitting layer may include two or more materials selected from red, green, and blue emitting materials, wherein the two or more materials are mixed with each other in a single layer to emit white light.

[0224] The emitting layer may include a host and a dopant. The dopant may include at least one of a phosphorescent dopant and a fluorescent dopant. The phosphorescent dopant may include an organometallic compound represented by Formula 1.

[0225] Based on about 100 parts by weight of the body, the amount of dopant in the emitter layer can be in the range of about 0.01 parts by weight to about 15 parts by weight, but the embodiments of this disclosure are not limited thereto.

[0226] The thickness of the emission layer can be approximately to approximately (For example, about to approximately Within these ranges, excellent light emission characteristics can be obtained without significantly increasing the driving voltage when the thickness of the emitting layer is within these ranges.

[0227] [The main body in the emission layer]

[0228] In one or more embodiments, the body may include a compound represented by the following formula 301.

[0229] Formula 301

[0230] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21

[0231] In Equation 301,

[0232] Ar 301 C5-C can be substituted or unsubstituted. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group,

[0233] xb11 can be 1, 2, or 3.

[0234] L 301 It can be selected from substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hypoaryl, substituted or unsubstituted divalent nonaromatic condensed polycyclic groups, and substituted or unsubstituted divalent nonaromatic condensed heterocyclic groups.

[0235] xb1 can be an integer from 0 to 5.

[0236] R 301 It can be selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, -Si(Q 301 (Q) 302 (Q) 303 -N(Q) 301 (Q) 302 -B(Q) 301 (Q) 302 -C(=O)(Q) 301 -S(=O)2(Q) 301 ) and -P(=O)(Q 301 (Q) 302 ),and

[0237] xb21 can be an integer from 1 to 5.

[0238] Among them, Q 301 To Q 303 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, but the embodiments disclosed herein are not limited thereto.

[0239] In one embodiment, Ar in formula 301 301 It can be selected from:

[0240] Naphthalene group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, Groups, tetraphenyl groups, styrene groups, perylene groups, pentylenetetrazol groups, indene-anthracene groups, dibenzofuran groups, and dibenzothiophene groups; and

[0241] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32-C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 The following groups are selected from at least one of the following groups: naphthyl group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, Groups, tetraphenyl group, furan group, perylene group, pentylenetetrazol group, indene-anthracene group, dibenzofuran group and dibenzothiophene group,

[0242] Among them, Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, but the embodiments disclosed herein are not limited thereto.

[0243] When xb11 in equation 301 is 2 or greater, two or more Ar 301 They can be connected to each other via a single key.

[0244] In one or more embodiments, the compound represented by formula 301 may be represented by formula 301-1 or formula 301-2:

[0245]

[0246] In Equations 301-1 and 301-2,

[0247] A 301 To A 304 They can all be independently selected from benzene rings, naphthalene rings, phenanthrene rings, fluoranthene rings, benzo[9,10]phenanthrene rings, pyrene rings, Rings, pyridine rings, pyrimidine rings, indene rings, fluorene rings, spirobisfluorene rings, benzo[a]fluorene rings, dibenzo[a]fluorene rings, indole rings, carbazole rings, benzo[a]carbazole rings, dibenzo[a]carbazole rings, furan rings, benzo[a]furan rings, dibenzo[a]furan rings, naphtho[a]furan rings, benzo[a]naphtho[a]furan rings, dinaphtho[a]furan rings, thiophene rings, benzo[a]thiophene rings, dibenzo[a]thiophene rings, naphtho[a]thiophene rings, benzo[a]naphtho[a]thiophene rings, and dinaphtho[a]thiophene rings.

[0248] X 301 It can be O, S or N-[(L 304 ) xb4 -R 304 ],

[0249] R 311 To R 314Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 ),

[0250] xb22 and xb23 can each be independently 0, 1, or 2.

[0251] L 301 xb1, R 301 and Q 31 To Q 33 Each of them can be independently identical to the ones described above.

[0252] L 302 To L 304 They can all independently bind with L 301 The descriptions are the same.

[0253] xb2 to xb4 can all be independently identical to those described in conjunction with xb1, and

[0254] R 302 To R 304 They can all independently bind with R 301 The descriptions are the same.

[0255] In one or more embodiments, L in Formula 301, Formula 301-1 and Formula 301-2 301 To L 304 Each can be independently selected from:

[0256] Phenylidene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluorenylanethyl, benzo[9,10]phenanthrene, pyrene, phenanthrene Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthrenediyl, acridineyl, phenanthrene-rheinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl; and

[0257] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazole, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridinyl Azinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32The following are selected from at least one of the following: phenylene, naphthylene, fluorene, spirodifluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenanthrene, anthracene, fluoranthracene, benzo[9,10]phenanthrene, pyrene, etc. Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl , pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthrene-pyridinyl, acridineyl, phenanthrene-pyridinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl;

[0258] Among them, Q 31 To Q 33 Each can be independently identical to the description above.

[0259] In one embodiment, R in Equations 301, 301-1, and 301-2 301 To R 304 Each can be independently selected from:

[0260] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0261] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazole, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridinyl Azinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 The following are selected from at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthraceneyl, fluoranthraceneyl, benzo[9,10]phenanthryl, pyreneyl, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl.

[0262] Among them, Q 31 To Q 33 Each can be independently identical to the description above.

[0263] In one or more embodiments, the host may include an alkaline earth metal complex. For example, the host may be selected from Be complexes (e.g., compound H55), Mg complexes, and Zn complexes.

[0264] The main body may include at least one selected from 9,10-bis(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), 9,10-bis(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-bis-9-carbazolylbenzene (mCP), 1,3,5-tris(carbazolyl-9-yl)benzene (TCP), and at least one selected from compounds H1 to H55, but the embodiments of this disclosure are not limited thereto:

[0265]

[0266]

[0267]

[0268] In one embodiment, the body may include at least one selected from silicon-containing compounds (e.g., bis(4-(9H-carbazole-9-yl)phenyl)diphenylsilane (BCPDS) used in the following examples) and phosphine oxide-containing compounds (e.g., (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenylphosphine oxide (POPCPA) used in the following examples).

[0269] The body may include only one compound or may include two or more compounds that are different from each other (e.g., the bodies in the following examples include BCPDS and POPCPA). In one or more embodiments, the body may alternatively have various other modifications.

[0270] [Including phosphorescent dopants in the emission layer within organic layer 150]

[0271] Phosphorescent dopants may include organometallic compounds represented by Formula 1.

[0272] In addition, phosphorescent dopants may include organometallic complexes represented by the following formula 401:

[0273] Formula 401

[0274] M(L 401 ) xc1 (L 402 ) xc2

[0275] Formula 402

[0276]

[0277] In Equations 401 and 402,

[0278] M can be selected from iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), and thulium (Tm).

[0279] L 401 The ligand can be represented by Equation 402, and xc1 can be 1, 2, or 3, wherein when xc1 is 2 or greater, two or more L... 401 They can be the same or different from each other.

[0280] L 402 It can be an organic ligand, and xc2 can be an integer from 0 to 4, where when xc2 can be 2 or greater, two or more L... 402 They can be the same or different from each other.

[0281] X 401 To X 404 They can each be nitrogen or carbon independently.

[0282] X 401 and X 403 It can be connected via a single or double key, X 402 and X 404 It can be connected via a single key or a double key.

[0283] A 401 and A 402 Each can be independently C5-C 60 Carbocyclic or C1-C 60 Heterocyclic group,

[0284] X 405 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q) 411 )-*'、*-C(Q 411 (Q) 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 ) = *' or * = C = *', where Q 411 and Q 412 They can all be independently hydrogen, deuterium, or C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl,

[0285] X 406It can be a single bond, O, or S.

[0286] R 401 and R 402 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 20 Alkyl, substituted or unsubstituted C1-C 20 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, -Si(Q 401 (Q) 402 (Q) 403 -N(Q) 401 (Q) 402 -B(Q) 401 (Q) 402 -C(=O)(Q) 401 -S(=O)2(Q) 401 ) and -P(=O)(Q 401 (Q) 402 ), and Q 401 To Q 403 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, C6-C 20 Aryl and C1-C 20 Mixed aromatics,

[0287] xc11 and xc12 can both be independent integers from 0 to 10, and

[0288] In Equation 402, * and *' both represent the binding position with M in Equation 401.

[0289] In one embodiment, A in Equation 402 401 and A 402They can all be independently selected from phenyl groups, naphthyl groups, fluorene groups, spirodifluorene groups, indene groups, pyrrole groups, thiophene groups, furan groups, imidazole groups, pyrazole groups, thiazole groups, isothiazole groups, oxazole groups, isoxazole groups, pyridine groups, pyrazine groups, pyrimidine groups, pyridazine groups, quinoline groups, isoquinoline groups, benzoquinoline groups, quinoxaloline groups, quinazoline groups, carbazole groups, benzimidazole groups, benzofuran groups, benzothiophene groups, isobenzothiophene groups, benzooxazole groups, isobenzooxazole groups, triazole groups, tetraazole groups, oxadiazole groups, triazine groups, dibenzofuran groups, and dibenzothiophene groups.

[0290] In one or more embodiments, in formula 402, i)X 401 It can be nitrogen, X 402 It can be carbon, or ii)X 401 and X 402 Both can be nitrogen.

[0291] In one or more embodiments, R in Formula 402 401 and R 402 Each can be independently selected from:

[0292] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 Alkoxy;

[0293] All are substituted with at least one of the following C1-C groups selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, phenyl, naphthyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, and norbornyl. 20 Alkyl and C1-C 20 Alkoxy;

[0294] Cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiophenyl;

[0295] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20The cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiopheneyl groups selected from at least one of the following: cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiopheneyl groups; and

[0296] -Si(Q 401 (Q) 402 (Q) 403 -N(Q) 401 (Q) 402 -B(Q) 401 (Q) 402 -C(=O)(Q) 401 -S(=O)2(Q) 401 ) and -P(=O)(Q 401 (Q) 402 ),

[0297] Among them, Q 401 To Q 403 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, and naphthyl groups are used, but the embodiments disclosed herein are not limited thereto.

[0298] In one or more embodiments, when xc1 in equation 401 is 2 or greater, two or more L 401 The two A's in 401 Optionally via X as a linker 407 Connected to each other, two A's 402 Optionally via X as a linker 408 They are interconnected (see compounds PD1 through PD4 and PD7). X 407 and X 408 They can all be independent single bonds, *-O-*', *-S-*', *-C(=O)-*', *-N(Q) 413 )-*'、*-C(Q 413 (Q) 414 )-*' or *-C(Q 413 )=C(Q 414 )-*'(where Q 413 and Q 414 They can all be independently hydrogen, deuterium, or C1-C 20Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl or naphthyl), but the embodiments disclosed herein are not limited thereto.

[0299] L in Equation 401 402 It can be a monovalent organic ligand, a divalent organic ligand, or a trivalent organic ligand. In one or more embodiments, L 402 The components may be selected from halogens, diketones (e.g., acetylacetone (compound)), carboxylic acids (e.g., pyridinecarboxylic acid (salt)), -C (=O), isonitriles, -CN and phosphorus-containing substances (e.g., phosphine or phosphorous acid (salt)), but the embodiments disclosed herein are not limited thereto.

[0300] In one or more embodiments, the phosphorescent dopant may be selected from, for example, compounds PD1 to PD25, but the embodiments of this disclosure are not limited thereto:

[0301]

[0302] Fluorescent dopants in the emitter layer

[0303] Fluorescent dopants may include arylamine compounds and / or styreneamine compounds.

[0304] Fluorescent dopants may include compounds represented by the following formula 501.

[0305] Formula 501

[0306]

[0307] In Equation 501,

[0308] Ar 501 C5-C can be substituted or unsubstituted. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group,

[0309] L 501 To L 503 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hybrid aryl, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic condensed heterocyclic groups,

[0310] xd1 to xd3 can each be an independent integer from 0 to 3.

[0311] R 501 and R 502 Each can be independently selected from substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, and substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, and

[0312] xd4 can be an integer from 1 to 6.

[0313] In one embodiment, Ar in Formula 501 501 It can be selected from:

[0314] Naphthyl group, heptadene group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, Groups, tetraphenyl groups, styrene groups, perylene groups, pentylenetetrazol groups, indene-anthracene groups, and indene-phenanthrene groups; and

[0315] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 The naphthyl group selected from at least one of alkoxy, phenyl, biphenyl, terphenyl and naphthyl, heptadene group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, Groups, tetraphenyl group, styrene group, perylene group, penfenol group, indene-anthracene group and indene-phenanthrene group.

[0316] In one or more embodiments, L in Formula 501 501 To L 503 Each can be independently selected from:

[0317] Phenylidene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluorenylanethyl, benzo[9,10]phenanthrene, pyrene, phenanthrene alkyl, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazoyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoyl, dibenzocarbazoyl, dibenzothiopheneyl, and pyridylene; and

[0318] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, The following are selected from at least one of the following groups: phenylene, perylene, pentofenyl, nehexaphenyl, nepentylphenyl, thiophenyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiophenolyl, and pyridyl; phenylene, naphthylene, fluoreneylene, spirodifluoreneyl, benzo[9,10]fluoreneyl, dibenzo[9,10]fluoreneyl, phenanthreneyl, anthraceneylene, fluorenyleneyl, benzo[9,10]phenanthreneyl, pyreneyleneyl, etc. The compounds are: alkyl, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazoyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoyl, dibenzothiopheneyl, dibenzothiopheneyl, and pyridylene.

[0319] In one or more embodiments, R in Formula 501 501 and R 502 Each can be independently selected from:

[0320] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene alkyl, peryl, pentyranyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, and pyridyl; and

[0321] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, alkyl, peryl, pentyranyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl and -Si(Q) 31 (Q) 32 (Q) 33 The following are selected from at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthraceneyl, fluoranthraceneyl, benzo[9,10]phenanthryl, pyreneyl, The following groups are listed: alkyl, peryl, pentyranyl, benzohexaphenyl, benzopentaphenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiopheneyl, and pyridyl.

[0322] Among them, Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0323] In one or more embodiments, xd4 in Formula 501 can be 2, but the embodiments of this disclosure are not limited thereto.

[0324] In one or more embodiments, the fluorescent dopant may be selected from compounds FD1 to FD22:

[0325]

[0326]

[0327]

[0328] In one or more embodiments, the fluorescent dopant may be selected from the compounds listed below, but the embodiments disclosed herein are not limited thereto.

[0329]

[0330] [Electron transport region in organic layer 150]

[0331] The electron transport region may have: i) a single-layer structure comprising a single layer containing a single material (e.g., composed of a single material); ii) a single-layer structure comprising a single layer containing multiple different materials (e.g., composed of multiple different materials); or iii) a multilayer structure having multiple layers comprising multiple different materials (e.g., composed of multiple different materials).

[0332] The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but embodiments of this disclosure are not limited thereto.

[0333] In one or more embodiments, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein, for each structure, the layers are sequentially stacked from the emitter layer in the order stated accordingly. However, embodiments of this disclosure are not limited thereto.

[0334] The electron transport region (e.g., a buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may include a metal-free compound containing at least one π-electron-deficient nitrogen-containing ring (or a π-electron-depleted nitrogen-containing ring).

[0335] "π-electron-poor nitrogen-containing rings" refer to C1-C rings with at least one *-N=*' moiety as the cyclic component. 60 Heterocyclic group.

[0336] For example, a "nitrogen-containing ring depleted of π electrons" can be: i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' moiety; ii) a heteropolycyclic group in which two or more 5- to 7-membered heteromonocyclic groups, each having at least one *-N=*' moiety, are condensed together; or iii) at least one of the 5- to 7-membered heteromonocyclic groups, each having at least one *-N=*' moiety, is combined with at least one C5-C 60 Heterocyclic groups formed by the condensation of carbocyclic groups.

[0337] Examples of π-electron-depleted nitrogen-containing rings include, but are not limited to, imidazole rings, pyrazole rings, thiazole rings, isothiazole rings, oxazole rings, isoxazole rings, pyridine rings, pyrazine rings, pyrimidine rings, pyridazine rings, indazole rings, purine rings, quinoline rings, isoquinoline rings, benzo[a]quinoline rings, phthalazine rings, naphthidine rings, quinoxaline rings, quinazoline rings, cyclophosphine rings, phenanthridine rings, acridine rings, phenanthrene-rhein rings, phenazine rings, benzimidazole rings, isobenzo[a]thiazole rings, benzo[a]oxazole rings, isobenzo[a]oxazole rings, triazole rings, tetraazole rings, oxadiazole rings, triazine rings, thiadiazole rings, imidazo[a]pyridine rings, imidazo[a]pyrimidine rings, and azacarbazole rings.

[0338] In one or more embodiments, the electron transport region may include a compound represented by the following formula 601:

[0339] Formula 601

[0340] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .

[0341] In Equation 601,

[0342] Ar 601 It can be substituted or unsubstituted C5-C 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group,

[0343] xe11 can be 1, 2, or 3.

[0344] L 601 It can be selected from substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hybrid aryl, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic condensed heterocyclic groups,

[0345] xe1 can be an integer from 0 to 5.

[0346] R 601 It can be selected from substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, -Si(Q 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q) 601 ) and -P(=O)(Q 601 (Q) 602 ),

[0347] Q 601 To Q 603 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, and

[0348] xe21 can be an integer from 1 to 5.

[0349] In one embodiment, xe11 numbers of Ar 601 R with xe21 numbers 601 At least one of them may include a nitrogen-containing ring that is π-electron depleted.

[0350] In one embodiment, Ar in Formula 601 601 It can be selected from:

[0351] Phenyl group, naphthyl group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, Groups, tetraphenyl groups, styrene groups, perylene groups, pentylenetetrazol groups, indoxanthracene groups, dibenzofuran groups, dibenzothiophene groups, carbazole groups, imidazole groups, pyrazole groups, thiazole groups, isothiazole groups, oxazole groups, isoxazole groups, pyridine groups, pyrazine groups, pyrimidine groups, pyridazine groups, indazole groups, purine groups, quinoline groups, isoquinoline groups, benzoquinoline groups, phthalazine groups, naphthidine groups, quinoxaloline groups, quinazolinoline groups, cyclophosphine groups, phenanthridine groups, acridine groups, phenanthrene-rhein groups, phenazine groups, benzimidazole groups, isobenzothiazole groups, benzoxazole groups, isobenzoxazole groups, triazole groups, tetraazole groups, oxadiazole groups, triazine groups, thiadiazole groups, imidazopyridine groups, imidazopyrimidine groups, and azacarbazole groups; and

[0352] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q) 31 (Q) 32 (Q) 33 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 The phenyl group, naphthyl group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, selected from at least one of the following: Groups, tetraphenyl group, styrene group, perylene group, pentylenetetrazol group, indoxanthracene group, dibenzofuran group, dibenzothiophene group, carbazole group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthidine group, quinoxaline group, quinazolinoline group, cyclophosphine group, phenanthridine group, acridine group, phenanthrene-rhein group, phenazine group, benzimidazole group, isobenzothiazole group, benzooxazole group, isobenzooxazole group, triazole group, tetraazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, and azacarbazole group,

[0353] Among them, Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0354] When xe11 in equation 601 is 2 or greater, two or more Ar 601 They can be connected to each other via a single key.

[0355] In one or more embodiments, Ar in Formula 601 601 It can be an anthracene group.

[0356] In one or more embodiments, the compound represented by formula 601 can be represented by formula 601-1:

[0357] Formula 601-1

[0358]

[0359] In Equation 601-1,

[0360] X 614 It can be N or C(R) 614 ), X 615 It can be N or C(R) 615 ), X 616 It can be N or C(R) 616 ), and X 614 To X 616 At least one of them can be N,

[0361] L 611 To L 613 They can all independently bind with L 601 The descriptions are the same.

[0362] xe611 to xe613 can all be independently identical to those described in conjunction with xe1.

[0363] R 611 To R 613 They can all independently bind with R 601 The descriptions are the same, and

[0364] R 614 To R 616 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0365] In one embodiment, L in Equation 601 601 L in Equation 601-1 611 To L 613 Each can be independently selected from:

[0366] Phenylidene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluorenylanethyl, benzo[9,10]phenanthrene, pyrene, phenanthrene Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthrenediyl, acridineyl, phenanthrene-rheinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl; and

[0367] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazine The following are at least one of the following groups selected from: phenylene, naphthidyl, quinoxolinyl, quinazolinyl, phenanthrynyl, phenanthrinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, and azacarbazolyl; phenylene, naphthylene, fluorene, spirodifluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenanthrynyl, anthraceneyl, fluoranthraceneyl, benzo[9,10]phenanthrynyl, pyreneylyl, etc. Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl , pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthreneridinyl, acridineyl, phenanthrene-pyridinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl,

[0368] However, the embodiments disclosed herein are not limited thereto.

[0369] In one or more embodiments, xe1 in Formula 601 and xe611 to xe613 in Formula 601-1 can each be independently 0, 1 or 2.

[0370] In one or more embodiments, R in Formula 601 601 R in equation 601-1 611 To R 613 Each can be independently selected from:

[0371] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cinolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl;

[0372] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalyl The phenyl, biphenyl, terphenyl, naphthinyl, quinoxalinyl, quinazolinyl, terazolinyl, phenanthrynyl, acridineyl, phenanthrynyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, and azacarbazolyl are selected from at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0373] -S(=O)2(Q 601 ) and -P(=O)(Q 601 (Q) 602 ),

[0374] Among them, Q 601 and Q 602 Each can be independently identical to the description above.

[0375] The electron transport region may include at least one compound selected from compounds ET1 to ET36, but embodiments of this disclosure are not limited thereto:

[0376]

[0377]

[0378]

[0379]

[0380] In one or more embodiments, the electron transport region may include at least one compound selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ.

[0381]

[0382] In one or more embodiments, the electron transport region may include a phosphine oxide-containing compound, but the embodiments of this disclosure are not limited thereto. In one embodiment, the phosphine oxide-containing compound may be used in a hole blocking layer in the electron transport region, but the embodiments of this disclosure are not limited thereto.

[0383] The thicknesses of the buffer layer, hole blocking layer, and electronic control layer can all be independently set to approximately [value missing]. to approximately (For example, about to approximately Within these ranges, excellent hole blocking characteristics or excellent electronic control characteristics can be obtained without significantly increasing the driving voltage when the thicknesses of the buffer layer, hole blocking layer, and electronic control layer are within these ranges.

[0384] The thickness of the electron transport layer can be approximately to approximately (For example, about to approximately Within the range of the above-mentioned thickness, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.

[0385] In addition to the materials mentioned above, the electron transport region (e.g., the electron transport layer in the electron transport region) may also include metallic materials.

[0386] The metal-containing material may include at least one selected from alkali metal complexes and alkaline earth metal complexes. The metal ion of the alkali metal complex may be selected from Li ions, Na ions, K ions, Rb ions, and Cs ions, while the metal ion of the alkaline earth metal complex may be selected from Be ions, Mg ions, Ca ions, Sr ions, and Ba ions. The ligand coordinated to the metal ion of the alkali metal complex or alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but the embodiments disclosed herein are not limited thereto.

[0387] In one or more embodiments, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium quinoline, LiQ) or compound ET-D2.

[0388]

[0389] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.

[0390] The electron injection layer may have: i) a monolayer structure comprising a single layer containing a single material (e.g., composed of a single material); ii) a monolayer structure comprising a single layer containing multiple different materials (e.g., composed of multiple different materials); or iii) a multilayer structure having multiple layers comprising multiple different materials (e.g., composed of multiple different materials).

[0391] The electron injection layer may include alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof.

[0392] The alkali metal can be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal can be Li, Na, or Cs. In one or more embodiments, the alkali metal can be Li or Cs, but the embodiments of this disclosure are not limited thereto.

[0393] Alkaline earth metals can be selected from Mg, Ca, Sr and Ba.

[0394] Rare earth metals can be selected from Sc, Y, Ce, Tb, Yb and Gd.

[0395] The alkali metal compounds, alkaline earth metal compounds, and rare earth metal compounds may be selected from oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of alkali metals, alkaline earth metals, and rare earth metals.

[0396] The alkali metal compounds may be selected from alkali metal oxides such as Li2O, Cs2O, and / or K2O and alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and / or KI. In one embodiment, the alkali metal compounds may be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, but the embodiments of the present disclosure are not limited thereto.

[0397] The alkaline earth metal compounds may be selected from alkaline earth metal oxides such as BaO, SrO, CaO, Ba x Sr 1-x O(0 < x < 1) and / or Ba x Ca 1-x O(0 < x < 1). In one embodiment, the alkaline earth metal compounds may be selected from BaO, SrO, and CaO, but the embodiments of the present disclosure are not limited thereto.

[0398] The rare earth metal compounds may be selected from YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, and TbF3. In one embodiment, the rare earth metal compounds may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but the embodiments of the present disclosure are not limited thereto.

[0399] The alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may include ions of alkali metals, alkaline earth metals, and rare earth metals, and the ligands coordinated to the metal ions of the alkali metal complexes, alkaline earth metal complexes, or rare earth metal complexes may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.

[0400] The electron injection layer may include alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof as described above (e.g., composed of alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof as described above). In one or more embodiments, the electron injection layer may also include organic materials. When the electron injection layer further includes organic materials, the alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix including the organic materials.

[0401] The thickness of the electron injection layer can be approximately to approximately (For example, about to approximately Within the range of the above-mentioned thickness, the electron injection layer can have satisfactory electron injection characteristics without significantly increasing the driving voltage.

[0402] [Second electrode 190]

[0403] The second electrode 190 can be positioned on the organic layer 150 having such a structure. The second electrode 190 can be a cathode serving as an electron injection electrode, and in this respect, the material used to form the second electrode 190 can be selected from metals, alloys, conductive compounds, and combinations thereof that have relatively low work functions.

[0404] The second electrode 190 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, and IZO, but embodiments of this disclosure are not limited thereto. The second electrode 190 may be a transmission electrode, a semi-transmission electrode, or a reflection electrode.

[0405] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.

[0406] [ Figures 2 to 4 [Description]

[0407] Figure 2 The organic light-emitting device 20 includes a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190, which are stacked sequentially in the order stated herein. Figure 3The organic light-emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 stacked sequentially in the order stated herein. Figure 4 The organic light-emitting device 40 includes a first capping layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 stacked sequentially in the order stated herein.

[0408] Reference Figures 2 to 4 It can be combined with reference Figure 1 The given description is used to understand the first electrode 110, the organic layer 150, and the second electrode 190.

[0409] In each of the organic layers 150 of organic light-emitting devices 20 and 40, light generated in the emitting layer can pass outward through the first electrode 110 (which is a semi-transparent electrode or a transmissive electrode) and the first capping layer 210, and in each of the organic layers 150 of organic light-emitting devices 30 and 40, light generated in the emitting layer can pass outward through the second electrode 190 (which is a semi-transparent electrode or a transmissive electrode) and the second capping layer 220.

[0410] The first capping layer 210 and the second capping layer 220 can improve the external luminescence efficiency according to the principle of constructive interference.

[0411] The first capping layer 210 and the second capping layer 220 can each be independently an organic capping layer including organic materials (e.g., composed of organic materials), an inorganic capping layer including inorganic materials (e.g., composed of inorganic materials), or a composite capping layer including organic and inorganic materials.

[0412] At least one of the first capping layer 210 and the second capping layer 220 may each independently comprise at least one material selected from carbocyclic compounds, heterocyclic compounds, amine compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalenephthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds, and amine compounds may optionally be substituted with substituents comprising at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one of the first capping layer 210 and the second capping layer 220 may each independently comprise an amine compound.

[0413] In one embodiment, at least one of the first capping layer 210 and the second capping layer 220 may each independently comprise a compound represented by formula 201 or a compound represented by formula 202.

[0414] In one or more embodiments, at least one of the first capping layer 210 and the second capping layer 220 may each independently include a compound selected from compounds HT28 to HT33 and compounds CP1 to CP5, but the embodiments of this disclosure are not limited thereto.

[0415]

[0416] In the above text, it has already been combined Figures 1 to 4 An organic light-emitting device according to an embodiment has been described. However, the embodiments disclosed herein are not limited thereto.

[0417] Layers constituting hole transport regions, emission regions, and electron transport regions can be formed in certain areas by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging (LITI).

[0418] When forming layers constituting hole transport regions, emitter layers, and electron transport regions by vacuum deposition, by considering the materials to be included in the layers to be formed and the structure of the layers to be formed, deposition temperatures of approximately 100°C to approximately 500°C and approximately 10 -8 To about 10 -3 The vacuum degree and about to approximately Vacuum deposition was performed at a deposition rate of [value missing].

[0419] When spin coating is used to form layers constituting hole transport regions, emitter layers, and electron transport regions, spin coating can be performed at coating speeds of about 2,000 rpm to about 5,000 rpm and at heat treatment temperatures of about 80°C to about 200°C, taking into account the materials to be included in the layers to be formed and the structure of the layers to be formed.

[0420] [General definition of substituents]

[0421] As used here, the term "C1-C" 60 "alkyl" refers to a straight-chain or branched monovalent group of an aliphatic saturated hydrocarbon having 1 to 60 carbon atoms, and non-limiting examples include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. As used herein, the term "C1-C" is also used. 60 "alkylene" refers to C1-C 60 Alkyl groups have the same structure as divalent groups.

[0422] As used here, the term "C2-C" 60 "Alkenyl" refers to the group formed at C2-C. 60 A hydrocarbon group having at least one carbon-carbon double bond at the middle or end of an alkyl group, non-limiting examples of which include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" is used... 60 "Alkenyl" refers to C2-C 60 Alkenes have divalent groups with the same structure.

[0423] As used here, the term "C2-C" 60 "Alkyne group" refers to the group at C2-C 60 A hydrocarbon group having at least one carbon-carbon triple bond at the middle or end of an alkyl group, non-limiting examples of which include ethynyl and propynyl groups. As used herein, the term "C2-C" is used... 60 "Immyneyl" refers to C2-C 60 The alkynyl group is a divalent group with the same structure.

[0424] As used here, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 Alkyl groups are monovalent groups, and non-limiting examples include methoxy, ethoxy, and isopropoxy.

[0425] As used here, the term "C3-C" 10 "Cycloalkyl" refers to a monocyclic saturated hydrocarbon group having 3 to 10 carbon atoms, and non-limiting examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "C3-C" is also relevant. 10 "Cycloalkylene" refers to C3-C 10 Cycloalkyl groups have the same divalent structure.

[0426] As used here, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as the cyclic atom and 1 to 10 carbon atoms, with non-limiting examples including 1,2,3,4-oxatriazolyl, tetrahydrofuranyl, and tetrahydrothiophenyl. The term "C1-C" as used herein... 10 "Heterocyclic alkyl" refers to C1-C 10 Heterocyclic alkyl groups have divalent groups with the same structure.

[0427] As used here, the term "C3-C" 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and lacking aromaticity; non-limiting examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C" is also relevant. 10 "Biopylene" refers to C3-C 10 Cycloalkenyl groups are divalent groups with the same structure.

[0428] As used here, the term "C1-C" 10"Heterocyclic alkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a cyclizing atom, one to ten carbon atoms, and at least one double bond in its ring. C1-C 10 Non-limiting examples of heterocyclic alkenyl groups include 4,5-dihydro-1,2,3,4-oxarizolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl" refers to C1-C 10 Heterocyclic alkenyl groups are divalent groups with the same structure.

[0429] As used here, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system comprising 6 to 60 carbon atoms, such as the term "C6-C" used herein. 60 "Aryl" refers to a divalent group in a carbocyclic aromatic system having 6 to 60 carbon atoms. (C6-C) 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, fluorenyl, and... Base. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, the two or more rings may be fused together.

[0430] As used here, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, Si, P, and S as a cyclizing atom in addition to 1 to 60 carbon atoms. The term "C1-C" is used herein. 60 "Hypo-aryl" refers to a divalent group having a heterocyclic aromatic system, wherein the heterocyclic aromatic system has at least one heteroatom selected from N, O, Si, P, and S as a cyclizing atom in addition to 1 to 60 carbon atoms. C1-C 60 Non-limiting examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiofuranyl. When C1-C 60 heteroaryl and C1-C 60 When each heteroaryl group comprises two or more rings, the two or more rings may condense together.

[0431] As used here, the term "C6-C" 60 "Aryloxy group" refers to the group consisting of -OA 102 (where A) 102 For C6-C 60 Aryl groups, such as the term "C6-C" as used herein. 60 "Arylthio" refers to the group consisting of -SA103 (where A) 103 For C6-C 60 (aryl) represents a group.

[0432] As used herein, the term "monovalent nonaromatic condensation polycyclic group" refers to a monovalent group having two or more rings condensed together, with only carbon atoms (e.g., having 8 to 60 carbon atoms) as cyclic atoms, and lacking aromaticity throughout its molecular structure. Non-limiting examples of monovalent nonaromatic condensation polycyclic groups include fluorenyl and adamantyl. As used herein, the term "divalent nonaromatic condensation polycyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic condensation polycyclic group.

[0433] As used herein, the term "monovalent non-aromatic condensed heterocyclic group" refers to a monovalent group having two or more rings condensed together, at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom in addition to carbon atoms (e.g., having 1 to 60 carbon atoms), and lacking aromaticity throughout its molecular structure. Non-limiting examples of monovalent non-aromatic condensed heterocyclic groups include the carbazole group. As used herein, the term "divalent non-aromatic condensed heterocyclic group" refers to a divalent group having the same structure as a monovalent non-aromatic condensed heterocyclic group.

[0434] As used here, the term "C5-C" 60 "Carbocyclic group" refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms, in which only carbon atoms are cyclic atoms. For example, the term "C5-C" as used herein... 60 "Carbocyclic group" refers to either aromatic or non-aromatic carbocyclic groups. (C5-C) 60 The carbocyclic group can be a ring (such as benzene), a monovalent group (such as phenyl), or a divalent group (such as phenylene). In one or more embodiments, depending on the connection to C5-C... 60 The number of substituents in the carbocyclic group, C5-C 60 The carbon cyclic group can be a trivalent group or a tetravalent group.

[0435] As used here, the term "C1-C" 60 A "heterocyclic group" refers to a group that, in addition to using at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom (excluding carbon, which can range from 1 to 60 carbon atoms), is cyclic with C5-C6. 60 Carbon cyclic groups are groups with the same structure.

[0436] In this specification, C5-C is replaced. 60 Carbocyclic groups, substituted C1-C 60 Heterocyclic groups, substituted C1-C 20 Alkylene, substituted C2-C 20 alkenyl, substituted C3-C10 Cycloalkylene, substituted C1-C 10 Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 aryl, substituted C1-C 60 Hybrid aryl, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heterocyclic group, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 At least one substituent among heteroaryl, substituted monovalent nonaromatic condensed polycyclic group, and substituted monovalent nonaromatic condensed heterocyclic group may be selected from:

[0437] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;

[0438] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, and C3-C. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q)11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 ) and -P(=O)(Q 11 (Q) 12 Choose at least one of the C1-Cs) 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;

[0439] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heterocyclic group;

[0440] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) and -P(=O)(Q 21 (Q) 22 Choose at least one of the C3-C options. 10 cycloalkyl, C1-C10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic condensed heterocyclic; and

[0441] -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 ),

[0442] Among them, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic, monovalent non-aromatic condensed heterocyclic, C1-C substituted with at least one of deuterium, -F and cyano. 60 Alkyl groups, substituted with at least one of deuterium, -F, and cyano groups, at a C6-C position. 60 Aryl, biphenyl, and terphenyl.

[0443] As used herein, the term "Ph" refers to phenyl, "Me" refers to methyl, "Et" refers to ethyl, and "ter-Bu" or "Bu" refers to... t"Refers to tert-butyl, as the term "OMe" used here refers to methyl methacrylate (MMA).

[0444] The term "biphenyl" as used here refers to "a phenyl group that has a substituted phenyl group." In other words, "biphenyl" is a phenyl group with a C6-C bond. 60 Aryl groups are substituted phenyl groups.

[0445] The term "terphenyl" as used here refers to "a phenyl group substituted with biphenyl groups." In other words, "terphenyl" is a phenyl group with C6-C substitution. 60 C6-C of aryl 60 Aryl groups are substituted phenyl groups.

[0446] Unless otherwise defined, * and *' as used here refer to the bonding site with the adjacent atom in the corresponding formula.

[0447] In the following description, the compounds according to the embodiments and the organic light-emitting devices according to the embodiments will be described in more detail with reference to the synthesis examples and examples. The expression "using B instead of A" used in the description of the synthesis examples means using the same molar equivalent of B instead of A.

[0448] [Synthesis Example]

[0449] Synthesis Example 1: Synthesis of Compound 1

[0450]

[0451] Synthesis of intermediate compound 1-B

[0452] 1-A (1.0 eq), iodomethane (3.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 12 hours. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and column chromatography was used to obtain intermediate compound 1-B (yield: 75%).

[0453] Synthesis of intermediate compound 1-C

[0454] Intermediate compound 1-B (1.0 eq), Sn (1.5 eq), and HCl (30 eq) were dissolved in ethanol and stirred at 80 °C for 12 hours. The reaction mixture was cooled to room temperature and then neutralized with NaOH solution. Extraction was then performed using dichloromethane and water to obtain an organic layer, which was subsequently filtered through diatomaceous earth / silica gel. The filtrate was dried over anhydrous magnesium sulfate and concentrated, and column chromatography (MC:hexane = 1:3) was used to obtain intermediate compound 1-C (yield: 86%).

[0455] Synthesis of intermediate compound 1-D

[0456] Intermediate compound 1-C (1.2 eq), 2-(3-bromo-5-(tert-butyl)phenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 3 h. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (ethyl acetate:hexane = 1:9) to obtain intermediate compound 1-D (yield: 78%).

[0457] Synthesis of intermediate compound 1-E

[0458] Intermediate compound 1-D (1.0 eq) was dissolved in triethyl orthoformate (30 eq) at 80 °C, followed by the addition of 37% HCl (1.5 eq) and stirring at 80 °C for 12 hours. The reaction mixture was cooled to room temperature, and the triethyl orthoformate was concentrated, followed by three extractions with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (MC, MC: 5 vol% methanol) to obtain intermediate compound 1-E (yield: 90%).

[0459] Synthesis of intermediate compound 1-F

[0460] Intermediate compound 1-E (1.0 eq) and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), and then distilled water was added. The mixture was stirred at room temperature for about 8 hours. The reaction mixture was washed with distilled water and filtered to obtain a solid, which was then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate and concentrated to obtain intermediate compound 1-F (yield: 94%).

[0461] Synthesis of Compound 1

[0462] Intermediate compound 1-F (1.0 eq), dichloro(1,5-cyclooctadiene)platin(II) (1.1 eq), and sodium acetate (3.0 eq) were dissolved in anhydrous 1,4-dioxane and stirred at 120 °C for 4 days under nitrogen conditions. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and compound 1 was obtained by column chromatography (MC: 50 vol% hexane) (yield: 23%).

[0463] Synthesis Example 2: Synthesis of Compound 2

[0464]

[0465] Synthesis of intermediate compound 2-B

[0466] 2-A (1.0 eq), 2,6-diphenyl-d 10 Aniline (1.2 eq), Pd₂(dba)₃ (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 12 h. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (dichloromethane:hexane = 1:3) to obtain intermediate compound 2-B (yield: 73%).

[0467] Synthesis of intermediate compound 2-C

[0468] Intermediate compound 2-B (1.0 eq), Sn (1.5 eq), and HCl (30 eq) were dissolved in ethanol and stirred at 80 °C for 12 hours. The reaction mixture was cooled to room temperature and then neutralized with NaOH solution. Extraction was then performed using dichloromethane and water to obtain an organic layer, which was subsequently filtered through diatomaceous earth / silica gel. The filtrate was dried over anhydrous magnesium sulfate and concentrated, and column chromatography (MC:hexane = 1:3) was used to obtain intermediate compound 2-C (yield: 85%).

[0469] Synthesis of intermediate compound 2-D

[0470] Intermediate compound 2-C (1.2 eq), 2-(3-bromo-5-(tert-butyl)phenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 3 hours. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (ethyl acetate:hexane = 1:9) to obtain intermediate compound 2-D (yield: 78%).

[0471] Synthesis of intermediate compound 2-E

[0472] Intermediate compound 2-D (1.0 eq) was dissolved in triethyl orthoformate (30 eq) at 80 °C, followed by the addition of 37% HCl (1.5 eq) and stirring at 80 °C for 12 hours. The reaction mixture was cooled to room temperature, and the reaction solvent was concentrated, followed by extraction with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (MC, MC: 1 vol% methanol, MC: 2 vol% methanol, MC: 5 vol% methanol) to obtain intermediate compound 2-E (yield: 89%).

[0473] Synthesis of intermediate compound 2-F

[0474] Intermediate compound 2-E (1.0 eq) and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), and then distilled water was added. The mixture was stirred at room temperature for about 8 hours. The reaction mixture was washed with distilled water and filtered to obtain a solid, which was then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate and concentrated to obtain intermediate compound 2-F (yield: 96%).

[0475] Synthesis of Compound 2

[0476] Intermediate compound 2-F (1.0 eq), dichloro(1,5-cyclooctadiene)platinum(II) (1.1 eq), and sodium acetate (3.0 eq) were dissolved in anhydrous 1,4-dioxane and stirred at 120 °C for 4 days under nitrogen conditions. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and compound 2 was obtained by column chromatography (MC: 50 vol% hexane) (yield: 23%).

[0477] Synthesis Example 3: Synthesis of Compound 3

[0478]

[0479] Synthesis of intermediate compound 3-B

[0480] 3-A (1.0 eq), iodomethane (3.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 120 °C for 12 hours. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and column chromatography was used to obtain intermediate compound 3-B (yield: 77%).

[0481] Synthesis of intermediate compound 3-C

[0482] Intermediate compound 3-B (1.0 eq), Sn (1.5 eq), and HCl (30 eq) were dissolved in ethanol and stirred at 80 °C for 12 hours. The reaction mixture was cooled to room temperature and then neutralized with NaOH solution. Extraction was then performed using dichloromethane and water to obtain an organic layer, which was subsequently filtered through diatomaceous earth / silica gel. The filtrate was dried over anhydrous magnesium sulfate and concentrated, and column chromatography (MC:hexane = 1:3) was used to obtain intermediate compound 3-C (yield: 88%).

[0483] Synthesis of intermediate compound 3-D

[0484] Intermediate compound 3-C (1.2 eq), 2-(3-bromo-5-(tert-butyl)phenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 3 h. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (ethyl acetate:hexane = 1:9) to obtain intermediate compound 3-D (yield: 74%).

[0485] Synthesis of intermediate compound 3-E

[0486] Intermediate compound 3-D (1.0 eq) was dissolved in triethyl orthoformate (30 eq) at 80 °C, followed by the addition of 37% HCl (1.5 eq) and stirring at 80 °C for 12 hours. The reaction mixture was cooled to room temperature, and the triethyl orthoformate was concentrated, followed by three extractions with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (MC, MC: 5 vol% methanol) to obtain intermediate compound 3-E (yield: 90%).

[0487] Synthesis of intermediate compound 3-F

[0488] Intermediate compound 3-E (1.0 eq) and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), and then distilled water was added. The mixture was stirred at room temperature for about 8 hours. The reaction mixture was washed with distilled water and filtered to obtain a solid, which was then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated to give intermediate compound 3-F (yield: 95%).

[0489] Synthesis of Compound 3

[0490] Intermediate compound 3-F (1.0 eq), dichloro(1,5-cyclooctadiene)platin(II) (1.1 eq), and sodium acetate (3.0 eq) were dissolved in anhydrous 1,4-dioxane and stirred at 120 °C for 4 days under nitrogen conditions. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and compound 3 was obtained by column chromatography (MC: 50 vol% hexane) (yield: 21%).

[0491] Synthesis Example 4: Synthesis of Compound 4

[0492]

[0493] Synthesis of intermediate compound 4-B

[0494] 4-A(1-(1-bromoethyl)-2-nitrobenzene)(1.0 eq), 2,6-diphenyl-d 10 1.2 eq of aniline, chlorophenylallyl[1,3-bis(2,6-diisopropylphenyl)-2-imidazolinene]palladium(II) (5 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 12 h. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and column chromatography (dichloromethane:hexane = 1:3) was used to obtain intermediate compound 4-B (yield: 75%).

[0495] Synthesis of intermediate compound 4-C

[0496] Intermediate compound 4-B (1.0 eq), Sn (3.5 eq), and HCl (5.5 eq) were dissolved in ethanol and stirred at 80 °C for 12 hours. The reaction mixture was cooled to room temperature and then neutralized with NaOH solution. Extraction was then performed using dichloromethane and water to obtain an organic layer, which was subsequently filtered through diatomaceous earth / silica gel. The filtrate was dried over anhydrous magnesium sulfate and concentrated, and column chromatography (MC:hexane = 1:3) was used to obtain intermediate compound 4-C (yield: 82%).

[0497] Synthesis of intermediate compound 4-D

[0498] Intermediate compound 4-C (1.2 eq), 2-(3-bromo-5-(tert-butyl)phenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 3 h. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (ethyl acetate:hexane = 1:9) to obtain intermediate compound 4-D (yield: 78%).

[0499] Synthesis of intermediate compound 4-E

[0500] Intermediate compound 4-D (1.0 eq) was dissolved in triethyl orthoformate (30 eq) at 80 °C, followed by the addition of 37% HCl (1.5 eq) and stirring at 80 °C for 12 hours. The reaction mixture was cooled to room temperature, and the reaction solvent was concentrated, followed by extraction with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (MC, MC: 1 vol% methanol, MC: 2 vol% methanol, MC: 5 vol% methanol) to obtain intermediate compound 4-E (yield: 89%).

[0501] Synthesis of intermediate compound 4-F

[0502] Intermediate compound 4-E (1.0 eq) and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), then distilled water was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was washed with distilled water and filtered to obtain a solid, which was then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate and concentrated to obtain intermediate compound 4-F (yield: 94%).

[0503] Synthesis of Compound 4

[0504] Intermediate compound 4-F (1.0 eq), dichloro(1,5-cyclooctadiene)platin(II) (1.1 eq), and sodium acetate (3.0 eq) were dissolved in anhydrous 1,4-dioxane and stirred at 120 °C for 4 days under nitrogen conditions. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and compound 4 was obtained by column chromatography (MC: 50 vol% hexane) (yield: 23%).

[0505] Synthesis Example 5: Synthesis of Compound 5

[0506]

[0507] Synthesis of intermediate compound 5-B

[0508] 5-A (1.0 eq), iodomethane (3.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 120 °C for 12 h. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and column chromatography was used to obtain intermediate compound 5-B (yield: 71%).

[0509] Synthesis of intermediate compound 5-C

[0510] Intermediate compound 5-B (1.0 eq), Sn (3.0 eq), and HCl (5.5 eq) were dissolved in ethanol and stirred at 80 °C for 12 hours. The reaction mixture was cooled to room temperature and then neutralized with NaOH solution. Extraction was then performed using dichloromethane and water to obtain an organic layer, which was subsequently filtered through diatomaceous earth / silica gel. The filtrate was dried over anhydrous magnesium sulfate and concentrated, and column chromatography (MC:hexane = 1:3) was used to obtain intermediate compound 5-C (yield: 91%).

[0511] Synthesis of intermediate compound 5-D

[0512] Intermediate compound 5-C (1.2 eq), 2-(3-bromo-5-(tert-butyl)phenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 3 h. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (ethyl acetate:hexane = 1:9) to obtain intermediate compound 5-D (yield: 73%).

[0513] Synthesis of intermediate compound 5-E

[0514] Intermediate compound 5-D (1.0 eq) was dissolved in triethyl orthoformate (30 eq) at 80 °C, followed by the addition of 37% HCl (1.5 eq) and stirring at 80 °C for 12 hours. The reaction mixture was cooled to room temperature, and the triethyl orthoformate was concentrated and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (MC, MC: 5 vol% methanol) to obtain intermediate compound 5-E (yield: 90%).

[0515] Synthesis of intermediate compound 5-F

[0516] Intermediate compound 5-E (1.0 eq) and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), and then distilled water was added, and the mixture was stirred at room temperature for about 8 hours. The reaction mixture was washed with distilled water and filtered to obtain a solid, which was then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate and concentrated to obtain intermediate compound 5-F (yield: 94%).

[0517] Synthesis of Compound 5

[0518] Intermediate compound 5-F (1.0 eq), dichloro(1,5-cyclooctadiene)platinum(II) (1.1 eq), and sodium acetate (3.0 eq) were dissolved in anhydrous 1,4-dioxane and stirred at 120 °C for 4 days under nitrogen conditions. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and compound 5 was obtained by column chromatography (MC: 50 vol% hexane) (yield: 21%).

[0519] Synthesis Example 6: Synthesis of Compound 6

[0520]

[0521] Synthesis of intermediate compound 6-B

[0522] 1-(2-bromopropan-2-yl)-2-nitrobenzene (1.0 eq), 2,6-diphenyl-d 10Aniline (1.2 eq), chlorophenylallyl[1,3-bis(2,6-diisopropylphenyl)-2-imidazolinene]palladium(II) (5 mol%) and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 120 °C for 12 h. The reaction mixture was cooled to room temperature and then extracted with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and column chromatography (dichloromethane:hexane = 1:3) was used to obtain intermediate compound 6-B (yield: 74%).

[0523] Synthesis of intermediate compound 6-C

[0524] Intermediate compound 6-B (1.0 eq), Sn (3.5 eq), and HCl (5.5 eq) were dissolved in ethanol and stirred at 80 °C for 12 hours. The reaction mixture was cooled to room temperature and then neutralized with NaOH solution. Extraction was then performed using dichloromethane and water to obtain an organic layer, which was subsequently filtered through diatomaceous earth / silica gel. The filtrate was dried over anhydrous magnesium sulfate and concentrated, and column chromatography (MC:hexane = 1:3) was used to obtain intermediate compound 6-C (yield: 89%).

[0525] Synthesis of intermediate compound 6-D

[0526] Intermediate compound 6-C (1.2 eq), 2-(3-bromo-5-(tert-butyl)phenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 3 hours. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (ethyl acetate:hexane = 1:9) to obtain intermediate compound 6-D (yield: 77%).

[0527] Synthesis of intermediate compound 6-E

[0528] Intermediate compound 6-D (1.0 eq) was dissolved in triethyl orthoformate (30 eq) at 80 °C, followed by the addition of 37% HCl (1.5 eq) and stirring at 80 °C for 12 hours. The reaction mixture was cooled to room temperature, and the reaction solvent was concentrated, followed by extraction with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (MC, MC: 1 vol% methanol, MC: 2 vol% methanol, MC: 5 vol% methanol) to obtain intermediate compound 6-E (yield: 89%).

[0529] Synthesis of intermediate compound 6-F

[0530] Intermediate compound 6-E (1.0 eq) and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), then distilled water was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was washed with distilled water and filtered to obtain a solid, which was then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated to obtain intermediate compound 6-F (yield: 95%).

[0531] Synthesis of Compound 6

[0532] Intermediate compound 6-F (1.0 eq), dichloro(1,5-cyclooctadiene)platin(II) (1.1 eq), and sodium acetate (3.0 eq) were dissolved in anhydrous 1,4-dioxane and stirred at 120 °C for 4 days under nitrogen conditions. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and compound 6 was obtained by column chromatography (MC: 50 vol% hexane) (yield: 25%).

[0533] Synthesis Example 7: Synthesis of Compound 7

[0534]

[0535] Synthesis of intermediate compound 7-B

[0536] 7-A (1.0 eq), iodomethane (3.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 120 °C for 12 hours. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and column chromatography was used to obtain intermediate compound 7-B (yield: 71%).

[0537] Synthesis of intermediate compound 7-C

[0538] Intermediate compound 7-B (1.0 eq), Sn (3.0 eq), and HCl (5.5 eq) were dissolved in ethanol and stirred at 80 °C for 12 hours. The reaction mixture was cooled to room temperature and then neutralized with NaOH solution. Extraction was then performed using dichloromethane and water to obtain an organic layer, which was subsequently filtered through diatomaceous earth / silica gel. The filtrate was dried over anhydrous magnesium sulfate and concentrated, and column chromatography (MC:hexane = 1:3) was used to obtain intermediate compound 7-C (yield: 91%).

[0539] Synthesis of intermediate compound 7-D

[0540] Intermediate compound 7-C (1.2 eq), 2-(3-bromo-5-(tert-butyl)phenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 3 hours. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (ethyl acetate:hexane = 1:9) to obtain intermediate compound 7-D (yield: 73%).

[0541] Synthesis of intermediate compound 7-E

[0542] Intermediate compound 7-D (1.0 eq) was dissolved in triethyl orthoformate (30 eq) at 80 °C, followed by the addition of 37% HCl (1.5 eq) and stirring at 80 °C for 12 hours. The reaction mixture was cooled to room temperature, and the triethyl orthoformate was concentrated, followed by three extractions with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (MC, MC: 5 vol% methanol) to obtain intermediate compound 7-E (yield: 90%).

[0543] Synthesis of intermediate compound 7-F

[0544] Intermediate compound 7-E (1.0 eq) and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), and then distilled water was added, and the mixture was stirred at room temperature for about 8 hours. The reaction mixture was washed with distilled water and filtered to obtain a solid, which was then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate and concentrated to obtain intermediate compound 7-F (yield: 94%).

[0545] Synthesis of Compound 7

[0546] Intermediate compound 7-F (1.0 eq), dichloro(1,5-cyclooctadiene)platinum(II) (1.1 eq), and sodium acetate (3.0 eq) were dissolved in anhydrous 1,4-dioxane and stirred at 120 °C for 4 days under nitrogen conditions. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and compound 7 was obtained by column chromatography (MC: 50 vol% hexane) (yield: 26%).

[0547] Synthesis Example 8: Synthesis of Compound 8

[0548]

[0549] Synthesis of intermediate compound 8-B

[0550] 8-A (1.0 eq), 2,6-diphenyl-d 10 Aniline (1.2 eq), Pd₂(dba)₃ (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 12 h. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (dichloromethane:hexane = 1:3) to obtain intermediate compound 8-B (yield: 84%).

[0551] Synthesis of intermediate compound 8-C

[0552] Intermediate compound 8-B (1.0 eq), Sn (3.0 eq), and HCl (5.5 eq) were dissolved in ethanol and stirred at 80 °C for 12 hours. The reaction mixture was cooled to room temperature and then neutralized with NaOH solution. Extraction was then performed using dichloromethane and water to obtain an organic layer, which was subsequently filtered through diatomaceous earth / silica gel. The filtrate was dried over anhydrous magnesium sulfate and concentrated, and column chromatography (MC:hexane = 1:3) was used to obtain intermediate compound 8-C (yield: 91%).

[0553] Synthesis of intermediate compound 8-D

[0554] Intermediate compound 8-C (1.2 eq), 2-(3-bromo-5-(tert-butyl)phenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 3 h. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (ethyl acetate:hexane = 1:9) to obtain intermediate compound 8-D (yield: 72%).

[0555] Synthesis of intermediate compound 8-E

[0556] Intermediate compound 8-D (1.0 eq) was dissolved in triethyl orthoformate (30 eq) at 80 °C, followed by the addition of 37% HCl (1.5 eq) and stirring at 80 °C for 12 hours. The reaction mixture was cooled to room temperature, and the reaction solvent was concentrated, followed by extraction with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (MC, MC: 1 vol% methanol, MC: 2 vol% methanol, MC: 5 vol% methanol) to obtain intermediate compound 8-E (yield: 95%).

[0557] Synthesis of intermediate compound 8-F

[0558] Intermediate compound 8-E (1.0 eq) and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), and then distilled water was added. The mixture was stirred at room temperature for about 8 hours. The reaction mixture was washed with distilled water and filtered to obtain a solid, which was then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate and concentrated to obtain intermediate compound 8-F (yield: 93%).

[0559] Synthesis of Compound 8

[0560] Intermediate compound 8-F (1.0 eq), dichloro(1,5-cyclooctadiene)platinum(II) (1.1 eq), and sodium acetate (3.0 eq) were dissolved in anhydrous 1,4-dioxane and stirred at 120 °C for 4 days under nitrogen conditions. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and compound 8 was obtained by column chromatography (MC: 50 vol% hexane) (yield: 22%).

[0561] Synthesis Example 9: Synthesis of Compound 9

[0562]

[0563] Synthesis of intermediate compound 9-B

[0564] 9-A (1.0 eq), iodomethane (5.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 120 °C for 12 hours. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and column chromatography was used to obtain intermediate compound 9-B (yield: 90%).

[0565] Synthesis of intermediate compound 9-C

[0566] Intermediate compound 9-B (1.0 eq), Sn (3.0 eq), and HCl (5.5 eq) were dissolved in ethanol and stirred at 80 °C for 12 hours. The reaction mixture was cooled to room temperature and then neutralized with NaOH solution. Extraction was then performed using dichloromethane and water to obtain an organic layer, which was subsequently filtered through diatomaceous earth / silica gel. The filtrate was dried over anhydrous magnesium sulfate and concentrated, and column chromatography (MC:hexane = 1:3) was used to obtain intermediate compound 9-C (yield: 93%).

[0567] Synthesis of intermediate compound 9-D

[0568] Intermediate compound 9-C (1.2 eq), 2-(3-bromo-5-(tert-butyl)phenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 3 h. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (ethyl acetate:hexane = 1:9) to obtain intermediate compound 9-D (yield: 76%).

[0569] Synthesis of intermediate compound 9-E

[0570] Intermediate compound 9-D (1.0 eq) was dissolved in triethyl orthoformate (30 eq) at 80 °C, followed by the addition of 37% HCl (1.5 eq) and stirring at 80 °C for 12 hours. The reaction mixture was cooled to room temperature, and the triethyl orthoformate was concentrated, followed by three extractions with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (MC, MC: 5 vol% methanol) to obtain intermediate compound 9-E (yield: 91%).

[0571] Synthesis of intermediate compound 9-F

[0572] Intermediate compound 9-E (1.0 eq) and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), and then distilled water was added. The mixture was stirred at room temperature for about 8 hours. The reaction mixture was washed with distilled water and filtered to obtain a solid, which was then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate and concentrated to obtain intermediate compound 9-F (yield: 96%).

[0573] Synthesis of Compound 9

[0574] Intermediate compound 9-F (1.0 eq), dichloro(1,5-cyclooctadiene)platinum(II) (1.1 eq), and sodium acetate (3.0 eq) were dissolved in anhydrous 1,4-dioxane and stirred at 120 °C for 4 days under nitrogen conditions. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and compound 9 was obtained by column chromatography (MC: 50 vol% hexane) (yield: 27%).

[0575] Synthesis Example 10: Synthesis of Compound 10

[0576]

[0577] Synthesis of intermediate compound 10-B

[0578] 10-A (1.0 eq), 2,6-diphenyl-d 10 Aniline (1.2 eq), Pd₂(dba)₃ (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 12 h. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and column chromatography was used to obtain intermediate compound 10-B (yield: 74%).

[0579] Synthesis of intermediate compound 10-C

[0580] Intermediate compound 10-B (1.0 eq), Sn (3.0 eq), and HCl (5.5 eq) were dissolved in ethanol and stirred at 80 °C for 12 hours. The reaction mixture was cooled to room temperature and then neutralized with NaOH solution. Extraction was then performed using dichloromethane and water to obtain an organic layer, which was subsequently filtered through diatomaceous earth / silica gel. The filtrate was dried over anhydrous magnesium sulfate and concentrated, and column chromatography was used to obtain intermediate compound 10-C (yield: 95%).

[0581] Synthesis of intermediate compound 10-D

[0582] Intermediate compound 10-C (1.2 eq), 2-(3-bromo-5-(tert-butyl)phenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 3 hours. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and column chromatography was used to obtain intermediate compound 10-D (yield: 70%).

[0583] Synthesis of intermediate compound 10-E

[0584] Intermediate compound 10-D (1.0 eq) was dissolved in triethyl orthoformate (30 eq) at 80 °C, followed by the addition of 37% HCl (1.5 eq) and stirring at 80 °C for 12 hours. The reaction mixture was cooled to room temperature, and the reaction solvent was concentrated, followed by extraction with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and then subjected to column chromatography (dichloromethane:methanol = 20:1) to obtain intermediate compound 10-E (yield: 91%).

[0585] Synthesis of intermediate compound 10-F

[0586] Intermediate compound 10-E (1.0 eq) and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), then distilled water was added and the mixture was stirred at room temperature for 4 hours. The reaction mixture was washed with distilled water and filtered to obtain a solid, which was then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated to obtain intermediate compound 10-F (yield: 95%).

[0587] Synthesis of Compound 10

[0588] Intermediate compound 10-F (1.0 eq), dichloro(1,5-cyclooctadiene)platin(II) (1.1 eq), and sodium acetate (3.0 eq) were dissolved in anhydrous 1,4-dioxane and stirred at 120 °C for 4 days under nitrogen conditions. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and compound 10 was obtained by column chromatography (MC: 50 vol% hexane) (yield: 27%).

[0589] Synthesis Example 11: Synthesis of Compound 11

[0590]

[0591] Synthesis of intermediate compound 11-B

[0592] 11-A (1.0 eq), iodomethane (3.0 eq), Pd(OAc)₂ (5 mol%), tri-tert-butylphosphine (10 mol%), and potassium carbonate (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 12 hours. The reaction mixture was cooled to room temperature and then extracted with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and column chromatography was used to obtain intermediate compound 11-B (yield: 87%).

[0593] Synthesis of intermediate compound 11-C

[0594] Intermediate compound 11-B (1.0 eq), Sn (3.0 eq), and HCl (5.5 eq) were dissolved in ethanol and stirred at 80 °C for 12 hours. The reaction mixture was cooled to room temperature and then neutralized with NaOH solution. Extraction was then performed using dichloromethane and water to obtain an organic layer, which was subsequently filtered through diatomaceous earth / silica gel. The filtrate was dried over anhydrous magnesium sulfate and concentrated, and column chromatography was used to obtain intermediate compound 11-C (yield: 92%).

[0595] Synthesis of intermediate compound 11-D

[0596] Intermediate compound 11-C (1.2 eq), 2-(3-bromo-5-(tert-butyl)phenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 4 hours. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and column chromatography was used to obtain intermediate compound 11-D (yield: 72%).

[0597] Synthesis of intermediate compound 11-E

[0598] Intermediate compound 11-D (1.0 eq) was dissolved in triethyl orthoformate (30 eq) at 80 °C, followed by the addition of 37% HCl (1.5 eq) and stirring at 80 °C for 12 hours. The reaction mixture was cooled to room temperature, and the triethyl orthoformate was concentrated, followed by three extractions with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and column chromatography was used to obtain intermediate compound 11-E (yield: 88%).

[0599] Synthesis of intermediate compound 11-F

[0600] Intermediate compound 11-E (1.0 eq) and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), and then distilled water was added. The mixture was stirred at room temperature for about 8 hours. The reaction mixture was washed with distilled water and filtered to obtain a solid, which was then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated to obtain intermediate compound 11-F (yield: 93%).

[0601] Synthesis of Compound 11

[0602] Intermediate compound 11-F (1.0 eq), dichloro(1,5-cyclooctadiene)platin(II) (1.1 eq), and sodium acetate (3.0 eq) were dissolved in anhydrous 1,4-dioxane and stirred at 120 °C for 4 days under nitrogen conditions. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and compound 11 was obtained by column chromatography (yield: 24%).

[0603] Synthesis Example 12: Synthesis of Compound 12

[0604]

[0605] Synthesis of intermediate compound 12-B

[0606] 12-A (1.0 eq), 2,6-diphenyl-d 10 Aniline (1.2 eq), Pd(OAc)₂ (5 mol%), tri-tert-butylphosphine (10 mol%), and potassium carbonate (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 12 h. The reaction mixture was cooled to room temperature and then extracted with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and column chromatography was used to obtain intermediate compound 12-B (yield: 70%).

[0607] Synthesis of intermediate compound 12-C

[0608] Intermediate compound 12-B (1.0 eq), Sn (3.0 eq), and HCl (5.5 eq) were dissolved in ethanol and stirred at 80 °C for 12 hours. The reaction mixture was cooled to room temperature and then neutralized with NaOH solution. Extraction was then performed using dichloromethane and water to obtain an organic layer, which was subsequently filtered through diatomaceous earth / silica gel. The filtrate was dried over anhydrous magnesium sulfate and concentrated, and column chromatography was used to obtain intermediate compound 12-C (yield: 88%).

[0609] Synthesis of intermediate compound 12-D

[0610] Intermediate compound 12-C (1.2 eq), 2-(3-bromo-5-(tert-butyl)phenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 3 hours. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and column chromatography was used to obtain intermediate compound 12-D (yield: 73%).

[0611] Synthesis of intermediate compound 12-E

[0612] Intermediate compound 12-D (1.0 eq) was dissolved in triethyl orthoformate (30 eq) at 80 °C, followed by the addition of 37% HCl (1.5 eq) and stirring at 80 °C for 12 hours. The reaction mixture was cooled to room temperature, and the reaction solvent was concentrated, followed by extraction with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and column chromatography was used to obtain intermediate compound 12-E (yield: 87%).

[0613] Synthesis of intermediate compound 12-F

[0614] Intermediate compound 12-E (1.0 eq) and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), then distilled water was added and the mixture was stirred at room temperature for 12 hours. The reaction mixture was washed with distilled water and filtered to obtain a solid, which was then extracted with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated to give intermediate compound 12-F (yield: 94%).

[0615] Synthesis of Compound 12

[0616] Intermediate compound 12-F (1.0 eq), dichloro(1,5-cyclooctadiene)platin(II) (1.1 eq), and sodium acetate (3.0 eq) were dissolved in anhydrous 1,4-dioxane and stirred at 120 °C for 4 days under nitrogen conditions. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and compound 12 was obtained by column chromatography (yield: ).

[0617] Evaluation Example 1

[0618] For each compound used in Synthetic Examples 1 through 12 and Comparative Example 1 below, quantum simulation was used to measure... 3 MLCT (%), Simulated Maximum Emission Wavelength (λ) max sim ), actual maximum transmission wavelength (λ) max exp )and 3 The MC energy, and the results are shown in Table 1.

[0619] In more detail, the properties of compounds 1 through 12, as well as compound A as a comparative compound, were evaluated. The highest occupied molecular orbital (HOMO) and LUMO energies were measured by differential pulse voltammetry. The properties were evaluated using B3LYP functionals. 3 The energy levels of the MC state were calculated using density functional theory (DFT) calculations with a Gaussian procedure, and measured at the B3LYP / 6-31G(d,p) level with structural optimization. 3 MLCT value (%).

[0620] [Table 1]

[0621]

[0622]

[0623]

[0624] Table 1 shows the compounds 1 through 12. 3 The value of MC is significantly greater than that of compound A. 3 The value of MC. Therefore, in each case of compounds 1 through 12, from 3 MCLT state transition to 3 The reduced probability of the MC state (non-emission state) allows for excellent stability in the excited state and can improve the efficiency and lifetime of organic light-emitting devices, including organometallic compounds.

[0625] [Example]

[0626] Example 1

[0627] As both the substrate and anode, it has a strength of 15Ω / cm. 2 The ITO glass substrate (manufactured by Corning) was cut to a size of 50mm × 50mm × 0.7mm, and ultrasonicated for 5 minutes each with isopropanol and pure water, followed by cleaning by irradiation with ultraviolet light and exposure to ozone for 30 minutes. The glass substrate was then loaded onto a vacuum deposition apparatus.

[0628] 2-TNATA was vacuum deposited on an ITO anode formed on a glass substrate to form a structure with... A hole injection layer of a certain thickness is formed, and NPB is vacuum-deposited on the hole injection layer to form a hole injection layer with a certain thickness. A hole transport layer of a certain thickness.

[0629] Bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS) and (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenylphosphine oxide (POPCPA) (here, the weight ratio of BCPDS to POPCPA is 1:1) as co-hosts and compound 1 as a dopant are co-deposited on the hole transport layer in a weight ratio of 90:10 to form a structure with The thickness of the emission layer.

[0630] Vacuum deposition of diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1) on the emitter layer to form a structure with... A hole-blocking layer of a certain thickness is formed, and Alq3 is vacuum-deposited on the hole-blocking layer to form a hole-blocking layer with a certain thickness. A thick electron transport layer is formed, and LiF is vacuum-deposited on the electron transport layer to form a layer with [missing information]. An electron-injected layer of a certain thickness is then vacuum-deposited on the electron-injected layer to form a layer with [missing information]. A cathode of a certain thickness is used to complete the fabrication of organic light-emitting devices.

[0631]

[0632] Examples 2 through 12 and Comparison Example 1

[0633] Except that the corresponding compounds shown in Table 1 are used instead of compound 1 as a dopant in forming the emission layer, the organic light-emitting devices are each fabricated in the same manner as in Example 1.

[0634] Evaluation Example 2

[0635] For each organic light-emitting device fabricated in Examples 1 through 12 and Comparative Example 1, the driving voltage, current density, luminance, luminous efficiency, emission color, and maximum emission wavelength were measured using a Kethley SMU236 and a PR650 luminance meter, and the results are shown in Table 2.

[0636] [Table 2]

[0637]

[0638]

[0639]

[0640] Referring to Table 2, it is confirmed that, compared with the organic light-emitting device of Comparative Example 1, each of Examples 1 to 12 has a lower driving voltage, a higher brightness level, a higher luminous efficiency, and / or a longer lifetime.

[0641] Considering the previously described organic light-emitting devices including the aforementioned organometallic compounds, they can have high brightness, high efficiency, and long lifespan.

[0642] When describing embodiments of the invention, the use of "may" refers to "one or more embodiments of the invention." It will be understood that when an element or layer is referred to as being "on" another element or layer, "connected to," or "bonded to" another element or layer, or "adjacent" to another element or layer, the element or layer may be directly on, directly connected to, or directly bonded to the other element or layer, or directly adjacent to the other element or layer, or one or more intermediate elements or layers may be present. Conversely, when an element or layer is referred to as being "directly on" another element or layer, "directly connected to," "directly bonded to," or "immediately adjacent" to another element or layer, no intermediate elements or layers are present.

[0643] As used herein, the terms “basically,” “about,” and similar terms are used as approximations rather than terms of degree and are intended to account for inherent deviations in measured or calculated values ​​that would be recognized by one of ordinary skill in the art. Furthermore, any numerical range described herein is intended to include all subranges containing the same numerical precision within the range. For example, the range “1.0 to 10.0” is intended to include all subranges between the minimum value 1.0 and the maximum value 10.0 (and inclusive of the minimum value 1.0 and the maximum value 10.0), i.e., all subranges having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit described herein is intended to include all lower numerical limits contained therein, and any minimum numerical limit described herein is intended to include all higher numerical limits contained therein. Therefore, the applicant reserves the right to amend this specification (including the claims) to expressly state any subranges contained within the ranges expressly stated herein. All such ranges are inherently described in this specification such that amendments to expressly state any such subranges will be required.

[0644] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. The description of features or aspects within each embodiment should generally be considered applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the spirit and scope as defined by the claims and their equivalents.

Claims

1. An organic light-emitting device, the organic light-emitting device comprising: First electrode; Second electrode; An organic layer, located between the first electrode and the second electrode, the organic layer including an emission layer; and At least one organometallic compound represented by Formula 1: <Formula 1> ， In Equation 1, M is selected from platinum, palladium, rhodium, iridium, ruthenium, and osmium. Y1 is N, and Y2 and Y3 are both independently C. T1 through T4 are all independent chemical bonds. When T1 is the chemical bond, Y1 and M are directly bonded; when T2 is the chemical bond, Y2 and M are directly bonded; when T3 is the chemical bond, Y3 and M are directly bonded; and when T4 is the chemical bond, A4 and M are directly bonded. Among the bonds between M and Y1, M and Y2, M and Y3, and M and A4, two bonds are coordinate bonds, and the other two are covalent bonds. A1 is a group represented by any one of formulas 2A-1 to 2A-5. A2 is a group represented by either formula 2B-2 or formula 2B-3. A3 is a group represented by formula 2C-1. ， In equations 2A-1 to 2A-5, 2B-2 and 2B-3, and 2C-1 Y 21 For N or C(R) 11a ), Y 22 For N or C(R) 12a ), Y 23 For N or C(R) 13a ), Y 24 For N or C(R) 14a ), Y 25 For N or C(R) 15a ), Y 26 For N or C(R) 16a ), Y 27 For N or C(R) 17a ), and Y 28 For N or C(R) 18a ), Z 21 For *'-C, C(R) 21a ) or N, and Z 22 For *'-C, Z 31 For *'-N, R 11a To R 18a and R 21a All are independently identical to R1 described in combination 1, and * indicates a combination bit with adjacent T1, T2, or T3, and *' indicates a combination bit with adjacent L1, L2, L3, or L4. A 11 It has a phenyl group or a cyclopentyl group. A 12 It has a cyclopentyl group. c11 is 1. c12 is either 0 or 1, and when c12 is 0, A 12 It does not exist. L1 to L4 are each independently selected from single bonds, *-S-*', *-Se-*', and *-O-*'. a1 to a3 are all independently 1, and a4 is 0. When a4 is 0, A4 and A1 are not connected to each other. R1 to R3, R 11 and R 12 Each is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, and substituted or unsubstituted methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, or hexyl. R4 is C1-C 20 Alkyl, C6-C 20 aryl, =O or =S, or both selected from C1-C substituted with at least one deuterium. 20 Alkyl groups and substituted C6-C groups having at least one deuterium 20 At least one of the aryl groups is substituted by C1-C 20 Alkyl or C6-C 20 Aryl, b1, b11, and b12 are all independent integers from 0 to 4. b2 is an integer from 0 to 6. b3 is an integer from 0 to 3. b4 is an integer from 1 to 3. Both * and *' represent bonding sites with adjacent atoms.

2. The organic light-emitting device according to claim 1, wherein, The energy level of the triplet metal neutral state of the at least one organometallic compound is 0.26 kcal / mol or greater.

3. The organic light-emitting device according to claim 1, wherein, The emitter layer includes at least one organometallic compound.

4. An organometallic compound, said organometallic compound being represented by Formula 1: <Formula 1> ， in, In Equation 1, M is selected from platinum, palladium, rhodium, iridium, ruthenium, and osmium. Y1 is N, and Y2 and Y3 are both independently C. T1 through T4 are all independent chemical bonds, wherein when T1 is the chemical bond, Y1 and M are directly bonded; when T2 is the chemical bond, Y2 and M are directly bonded; when T3 is the chemical bond, Y3 and M are directly bonded; and when T4 is the chemical bond, A4 and M are directly bonded. Of the bonds between M and Y1, M and Y2, M and Y3, and M and A4, two are coordinate bonds, and the other two are covalent bonds. A1 is a group represented by any one of formulas 2A-1 to 2A-5. A2 is a group represented by either formula 2B-2 or formula 2B-3. A3 is a group represented by formula 2C-1. ， In equations 2A-1 to 2A-5, 2B-2 and 2B-3, and 2C-1 Y 21 For N or C(R) 11a ), Y 22 For N or C(R) 12a ), Y 23 For N or C(R) 13a ), Y 24 For N or C(R) 14a ), Y 25 For N or C(R) 15a ), Y 26 For N or C(R) 16a ), Y 27 For N or C(R) 17a ), and Y 28 For N or C(R) 18a ), Z 21 For *'-C, C(R) 21a ) or N, and Z 22 For *'-C, Z 31 For *'-N, R 11a To R 18a and R 21a All are independently identical to R1 described in combination 1, and * indicates a combination bit with adjacent T1, T2, or T3, and *' indicates a combination bit with adjacent L1, L2, L3, or L4. A 11 It has a phenyl group or a cyclopentyl group. A 12 It has a cyclopentyl group. c11 is 1. c12 is either 0 or 1, and when c12 is 0, A 12 It does not exist. L1 to L4 are each independently selected from single bonds, *-S-*', *-Se-*', and *-O-*'. a1 to a3 are all independently 1, and a4 is 0. When a4 is 0, A4 and A1 are not connected to each other. R1 to R3, R 11 and R 12 Each is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, and substituted or unsubstituted methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, or hexyl. R4 is C1-C 20 Alkyl, C6-C 20 aryl, =O or =S, or both selected from C1-C substituted with at least one deuterium. 20 Alkyl groups and substituted C6-C groups having at least one deuterium 20 At least one of the aryl groups is substituted by C1-C 20 Alkyl or C6-C 20 Aryl, b1, b11, and b12 are all independent integers from 0 to 4. b2 is an integer from 0 to 6. b3 is an integer from 0 to 3. b4 is an integer from 1 to 3. Both * and *' represent bonding sites with adjacent atoms.

5. The organometallic compound according to claim 4, wherein, A1 is selected from pyridine, pyrimidine, pyrazine, and triazine groups. A2 is selected from carbazole group, indolepyridine group, and indolepyrimidine group, and A3 is selected from phenyl groups, pyridine groups, pyrimidine groups, pyrazine groups, and triazine groups.

6. The organometallic compound according to claim 4, wherein, Both L1 and L3 are single bonds, and L2 is *-O-*'.

7. The organometallic compound according to claim 4, wherein, The organometallic compound represented by Formula 1 is represented by one of Formulas 1-2 and 1-10: <Equation 1-2> <Formula 1-10> ,and Among them, in equations 1-2 and 1-10, M, A1 to A3, A 11 A 12 Y1 to Y3, L1 to L3, a1 to a3, R1 to R4, R 11 R 12 b1 to b3, b11 and b12 are all independently identical to those described in combination formula 1. X 11 All were independently selected from C(R) 21 (R) 22 C(=O) and C(=S), X 21 To X 23 Each is independently C(R) 21 ),and R 21 and R 22 All are independently identical to R1 described in Associative Formula 1.

8. The organometallic compound according to claim 4, wherein, The organometallic compound represented by Formula 1 is represented by Formula 1A: <Formula 1A> ,and In Equation 1A, M, A1, A3, A 11 A 12 , Y1, Y3, L2 to L3, R1, R3, R4, R 11 R 12 b1, b3, b4, b11, b12, c11, and c12 are all independently identical to those described in combination 1. X 31 To X 32 Each is independently C(R) 32 ), A 31 It is a phenyl group. b31 is an integer from 0 to 4, and R 4a R 31 and R 32 All are independently identical to R1 described in Associative Formula 1.

9. The organometallic compound according to claim 4, wherein the organometallic compound is selected from compounds 1 to 12: 。

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