Organometallic compound and organic light emitting device comprising the same

Abstract

Provided are an organometallic compound represented by Formula 1 and an organic light emitting device including the same. The substituents of Formula 1 are the same as described in the specification. Formula 1

Description

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0063269, filed May 26, 2020, in the Korean Intellectual Property Office, the disclosure of which is incorporated herein in its entirety by reference. TECHNICAL FIELD

[0002] One or more embodiments relate to an organometallic compound and an organic light emitting device including the same. BACKGROUND

[0003] An organic light emitting device (OLED) is a self-emitting device having a wide viewing angle, high contrast, short response time, and / or suitable (excellent) characteristics in luminance, driving voltage, and / or response speed, and producing a full-color image, compared to a related art device.

[0004] An OLED can include a first electrode on a substrate and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes provided from the first electrode can move toward the emission layer through the hole transport region, and electrons provided from the second electrode can move toward the emission layer through the electron transport region. Carriers such as holes and electrons recombine in the emission layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light. SUMMARY

[0005] Aspects according to one or more embodiments relate to a novel organometallic compound and an organic light emitting device including the same.

[0006] Additional aspects will be set forth in part in the description which follows, and in part will become apparent to those skilled in the art upon examination of the following description, or can be learned by practice of the presented embodiments of the disclosure.

[0007] According to an embodiment, an organometallic compound is represented by Formula 1.

[0008] Formula 1

[0009]

[0010] In Formula 1,

[0011] M1may be selected from the group consisting of 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] Y1to Y3may each independently be N or C,

[0013] T1to T4may each independently be a bond, O, S, B(R'), N(R'), P(R'), C(R')(R"), Si(R')(R"), Ge(R')(R"), or C(=O), when T1is a bond, Y1and M1are directly bound to each other, when T2is a bond, Y2and M1are directly bound to each other, when T3is a bond, Y3and M1are directly bound to each other, and when T4is a bond, A4and M1are directly bound to each other,

[0014] Two of the bonds selected from the bond between M1and Y1or T1, the bond between M1and Y2or T2, the bond between M1and Y3or T3, and the bond between M1and A4or T4may each be a coordinate bond, and the other two bonds can each be a covalent bond,

[0015] A1to A3may each independently be selected from C5-C 60 carbocyclyl and C1-C 60 heterocyclyl,

[0016] L1to L4may each independently be selected from a single bond, a double bond, *-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-*',

[0017] a1to a4may each independently be an integer of 0 to 3, and when a1is 0, A1and A2are not connected to each other, when a2is 0, A2and A3are not connected to each other, when a3is 0, A3and A4are not connected to each other, and when a4is 0, A4and A1are not connected to each other,

[0018] L 11 and L 12 may each independently be selected from *-C(R 11 )(R 12 )-*', *-C(R 11 )=*', *=C(R 11 )-*', and *-C(R 11 )=C(R 12 )-*',

[0019] a11and a12may each independently be an integer of 1 to 3,

[0020] R', R", R1to R6, and R 11and R 12 may each independently be selected from the group consisting of hydrogen, deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, substituted or unsubstituted C1-C 60 alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 alkynyl, substituted or unsubstituted C1-C 60 alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 aralkyl, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 heteroaryloxy, substituted or unsubstituted C1-C 60 heteroarylthio, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -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 can each independently be an integer of 0 to 20,

[0022] b4 can be an integer of 0 to 6,

[0023] R', R", the number of R1of b1, the number of R2of b2, the number of R3of b3, the number of R4of b4, R5, R6, R 11 and R 12 adjacent groups in R1, R2, R3, R4, R5, R6, R 60 carbocyclic group or substituted or unsubstituted C1-C 60 heterocyclic group,

[0024] * and *' can each represent a bonding site to an adjacent atom,

[0025] substituted C5-C 60carbocyclyl, substituted C1-C 60 heterocyclyl, substituted C1-C 60 alkyl, substituted C2-C 60 alkenyl, substituted C2-C 60 alkynyl, substituted C1-C 60 alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 heterocycloalkyl, substituted C3-C 10 cycloalkenyl, substituted C1-C 10 heterocycloalkenyl, substituted C6-C 60 aryl, substituted C6-C 60 aryloxy, substituted C6-C 60 aralkyl, substituted C1-C 60 heteroaryl, substituted C1-C 60 heteroaryloxy, substituted C1-C 60 heteroaralkyl, substituted monovalent non-aromatic condensed polycyclyl and substituted monovalent non-aromatic condensed heteropolycyclyl can be selected from the group consisting of:

[0026] deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 alkoxy,

[0027] each of which is independently substituted with from one to three of deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 aralkyl, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclyl, monovalent non-aromatic condensed heteropolycyclyl, -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 )(Q12 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 Alkyne 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 60Aryloxy 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 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 Alkyne 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, -Cl, -Br, -I and cyano. 60 Alkyl groups, substituted with at least one of deuterium, -F, -Cl, -Br, -I, and cyano groups, are C6-C. 60 Aryl, biphenyl, and terphenyl.

[0032] According to another embodiment, an organic light-emitting device includes a first electrode, a second electrode, and an organic layer comprising an emission layer located between the first electrode and the second electrode.

[0033] The organic light-emitting device includes at least one of the organometallic compounds represented by Formula 1. Attached Figure Description

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

[0035] Figure 1 This is a schematic cross-sectional view of an embodiment of an organic light-emitting device;

[0036] Figure 2 This is a schematic cross-sectional view of an embodiment of an organic light-emitting device;

[0037] Figure 3 A schematic cross-sectional view of an embodiment of an organic light-emitting device; and

[0038] Figure 4 This is a schematic cross-sectional view of an embodiment of an organic light-emitting device. Detailed Implementation

[0039] Now, reference will be made in more detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein 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.

[0040] According to embodiments of this disclosure, organometallic compounds are represented by the following formula 1:

[0041] Formula 1

[0042]

[0043] Triple-state metal neutrality of organometallic compounds ( 3 The energy levels of the triplet metal-centered state (MC state) (E) 3MC ) can be higher than the triplet metal-to-ligand charge-transfer state of organometallic compounds ( 3 The energy level of the MLCT state (triplet metal-to-ligand charge transfer state) (E 3MLCT ).

[0044] For example, organometallic compounds 3 Energy level E of MC state 3MC It can be approximately 0.41 kcal / mol or greater. For example, E 3MCIt can be about 0.81 kcal / mol or less, for example, about 0.41 kcal / mol to about 0.81 kcal / mol.

[0045] When organometallic compounds satisfy the above-described E 3MC When the range is reached, organometallic compounds from 3 MCLT state transition to non-emission state (i.e., 3 The probability of the excited state (MC state) can be low. Therefore, the stability of organometallic compounds in the excited state can be suitable (e.g., excellent), and can improve the efficiency and lifetime of organic light-emitting devices that include organometallic compounds.

[0046] For example, organometallic compounds 3 MLCT (%) (existing in) 3 The proportion in the MLCT state can be about 10% or more. For example, organometallic compounds... 3 MLCT (%) can be approximately 30% or less.

[0047] In Formula 1, M1 can be 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).

[0048] In the embodiments, M1 may be selected from Pt, Pd, Cu, Ag, Au, Rh, Ir, Ru and Os.

[0049] In the embodiments, M1 can be Pt, but the embodiments of this disclosure are not limited thereto.

[0050] In Equation 1, Y1 to Y3 can each be N or C independently.

[0051] T1 to T4 can each be independently a chemical bond, O, S, B(R'), N(R'), P(R'), C(R')(R"), Si(R')(R"), Ge(R')(R"), or C (=O). When T1 is a chemical bond, Y1 and M1 are directly bonded to each other; when T2 is a chemical bond, Y2 and M1 are directly bonded to each other; when T3 is a chemical bond, Y3 and M1 are directly bonded to each other; and when T4 is a chemical bond, A4 and M1 are directly bonded to each other.

[0052] Two of the bonds selected from the bond between M1and Y1or T1, the bond between M1and Y2or T2, the bond between M1and Y3or T3, and the bond between M1and A4or T4may each be a coordinate bond, and the other two bonds can each be a covalent bond. That is, of the four bonds including the bond between M1and Y1or T1, the bond between M1and Y2or T2, the bond between M1and Y3or T3, and the bond between M1and A4or T4, two bonds can each be a coordinate bond, and the other two bonds can each be a covalent bond.

[0053] In an embodiment, T1to T4may each be a chemical bond, Y1may be N, Y2may be C, and at least one bond selected from the bond between Y1and M1and the bond between Y2and M1may each be a coordinate bond.

[0054] For example, Y1may be N, and Y2and Y3may each be C, but embodiments of the present disclosure are not limited thereto.

[0055] A1to A3in Formula 1may each be independently selected from C5-C 60 carbocyclyl and C1-C 60 heterocyclyl.

[0056] In an embodiment, A1to A3may each be independently selected from:

[0057] a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a benzo[9,10]phenanthryl group, a pyrenyl group, a group selected from the group consisting of a phenyl group, a naphthyl group, an anthracenyl group, and a phenanthrenyl group.

[0058] In embodiments, i) A1may be selected from a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, and a triazinyl group, and / or

[0059] ii) A2may be selected from an indolyl group, a carbazolyl group, an indolopyridinyl group, and an indolopyrimidinyl group, and / or

[0060] iii) A3may be selected from a phenyl group, a naphthyl group, an anthracenyl group, and a phenanthrenyl group.

[0061] For example, A1may be selected from the group consisting of a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a triazine group, and A2may be selected from the group consisting of an indole group, a carbazole group, an indolopyridine group, and an indolopyrimidine group. For example, A1may be selected from the group consisting of a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a triazine group, and A3may be selected from the group consisting of a phenyl group, a naphthyl group, an anthracene group, and a phenanthrene group. For example, A2may be selected from the group consisting of an indole group, a carbazole group, an indolopyridine group, and an indolopyrimidine group, and A3may be selected from the group consisting of a phenyl group, a naphthyl group, an anthracene group, and a phenanthrene group. For example, A1may be selected from the group consisting of a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a triazine group, A2may be selected from the group consisting of an indole group, a carbazole group, an indolopyridine group, and an indolopyrimidine group, and A3may be selected from the group consisting of a phenyl group, a naphthyl group, an anthracene group, and a phenanthrene group.

[0062] In embodiments, ia) A1may be a group represented by one of Formula 2A-1 to Formula 2A-5, and / or

[0063] iia) A2may be a group represented by one of Formula 2B-1 to Formula 2B-3, and / or

[0064] iiia) A3may be a group represented by Formula 2C-1:

[0065]

[0066] In Formula 2A-1 to Formula 2A-5, Formula 2B-1 to Formula 2B-3, and Formula 2C-1,

[0067] Y 21 may be N or C(R 11a ), Y 22 may be N or C(R 12a ), Y 23 may be N or C(R 13a ), Y 24 may be N or C(R 14a ), Y 25 may be N or C(R 15a ), Y 26 may be N or C(R 16a ), Y 27 may be N or C(R 17a ), and Y 28 may be N or C(R 18a ),

[0068] Z 21 may be *'-C, C(R 21a ), or N, and Z 22 may be *'-C, C(R 22a ), or N,

[0069] Z 31 may be -N or N(R 31a ),

[0070] R 11a to R 18a , R 21a and R 22a , and R 31a are each independently the same as described in connection with R1in Formula 1,

[0071] * indicates a bonding site to an adjacent T1, T2, or T3, and *' indicates a bonding site to an adjacent L1, L2, L3, or L4.

[0072] For example, Y 22 may be C(R 12a ) in Formulae 2A-1 to 2A-5 and Formula 2C-1.

[0073] For example, R 12a may be hydrogen, C1-C 20 alkyl, or C1-C 20 alkyl substituted with at least one C1-C 20 alkyl group.

[0074] For example, in Formulae 2A-1 to 2A-5, Y 21 may be C(R 11a ), and Y 23 may be C(R 13a ). For example, R 11a and R 13a may each be hydrogen.

[0075] For example, in Formulae 2A-1 to 2A-5, Z 21 may be C(R 21a ), and Z 22 may be *'-C. For example, R 21a may be hydrogen.

[0076] For example, in Formulae 2B-1 to 2B-3, Y 21 may be C(R 11a ), Y 22 may be C(R 12a ), Y 23 may be C(R 13a ), Y 24 may be C(R 14a ), Y 25 may be C(R 15a ), Y 26 may be C(R 16a ), Y 27may be C(R 17a ) and Y 28 may be C(R 18a ). For example, R 11a through R 18a may each be hydrogen.

[0077] For example, in Formula 2B-1 through Formula 2B-3, Z 21 may be *'-C and Z 31 may be *'-N.

[0078] For example, in Formula 2C-1, Y 21 may be C(R 11a ) and Y 23 may be C(R 13a ). For example, R 11a may be hydrogen or C6-C 20 aryl substituted with at least one deuterium. For example, R 13a may be hydrogen.

[0079] For example, in Formula 2A-1 and Formula 2A-4, when Y 21 is C(R 11a ), Y 22 is C(R 12a ), and R 12a is C1-C 20 alkyl, R 11a may be C6-C 20 aryl substituted with at least one deuterium.

[0080] For example, in Formula 2C-1, Z 21 may be *'-C, Z 22 may be *'-C.

[0081] For example, A1may be a group represented by one of Formula 2A-1 through Formula 2A-5, and A2may be a group represented by one of Formula 2B-1 through Formula 2B-3. For example, A1may be a group represented by one of Formula 2A-1 through Formula 2A-5, and A3may be a group represented by Formula 2C-1. For example, A2may be a group represented by one of Formula 2B-1 through Formula 2B-3, and A3may be a group represented by Formula 2C-1. For example, A1may be a group represented by one of Formula 2A-1 through Formula 2A-5, A2may be a group represented by one of Formula 2B-1 through Formula 2B-3, and A3may be a group represented by Formula 2C-1.

[0082] In Equation 1, L1 to L4 can be 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 the embodiments, L1 to L4 can each be an independent single bond or *-O-*'.

[0084] In Equation 1, a1 to a4 can each be an independent integer 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. When a4 is 0, A4 and A1 are not connected to each other.

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

[0086] L in Formula 1 11 and L 12 Each can be independently selected from *-C(R) 11 (R) 12 )-*'、*-C(R 11 )=*'、*=C(R 11 )-*' and *-C(R 11 )=C(R 12 )-*'.

[0087] In Equation 1, a11 and a12 can both be independent integers from 1 to 3. a11 represents the result of L... 11 The number of groups indicated, a12 indicates the number of groups composed of L 12 The number of groups represented, and when a11 is 2 or greater, the number of a11 groups is L. 11 They can be the same or different from each other. When a12 is 2 or greater, the L of a12 numbers... 12 They can be the same as or different from each other.

[0088] In the embodiments, a11 and a12 can each be 1 or 2 independently.

[0089] In the embodiment, i)L 11 and L 12 Both can be *-C(R)11 (R) 12 )-*', a11 can be 2, and a12 can be 1.

[0090] ii)L 11 It can be *-C(R) 11 )=C(R 12 )-*',L 12 It can be *-C(R) 11 (R) 12 )-*', and a11 and a12 can both be 1, or

[0091] iii)L 11 It can be *-C(R) 11 (R) 12 )-*',L 12 It can be *-C(R) 11 )=C(R 12 )-*', and a11 and a12 can both be 1.

[0092] In Equation 1, R', R", R1 to R6 and R 11 and R 12 Each 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 60heteroarylsulfinyl, substituted or unsubstituted monovalent non-aromatic condensed polycyclyl, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclyl, -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),

[0093] b1 to b3 can each independently be an integer of 0 to 20,

[0094] b4 can be an integer of 0 to 6,

[0095] R', R", the number of R1 of b1, the number of R2 of b2, the number of R3 of b3, the number of R4 of b4, R5, R6, R 11 , and R 12 adjacent groups among R 60 , and R 60 may optionally be linked to each other to form a substituted or unsubstituted C5-C

[0096] In an embodiment, R', R", R1 to R6, R 11 , and R 12 may each independently be selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidine group, a hydrazine group, a hydrazone group, a C1-C 20 alkyl group, and a C1-C 20 alkoxy group;

[0097] each substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidine group, a hydrazine group, a hydrazone group, a C1-C 20 alkyl group, and a C1-C 20 alkoxy group; 20 alkyl group, and a C1-C 20 alkoxy group;

[0098] a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a pyrrolyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolyl group, an isoquinolyl group, a quinoxalyl group, a quinazolyl group, a cinnolinyl group, and a triazinyl group;

[0099] each substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidine group, a hydrazine group, a hydrazone group, a C1-C 20 alkyl group, a 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 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:

[0100] 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 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 Choose at least one of the C1-C 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

[0101] -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),

[0102] wherein Q1to Q3and Q 31 to Q 33 are each independently selected from:

[0103] hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, C1-C 20 alkoxy, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 20 aryl, C1-C 20 heteroaryl, monovalent non-aromatic condensed polycyclic group, and monovalent non-aromatic condensed heteropolycyclic group.

[0104] In an embodiment, when L 12 is *-C(R 11 )=C(R 12 )-* and a12is 1, R 11 and R 12 may be linked to each other to form a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group.

[0105] In an embodiment, the organometallic compound represented by Formula 1 can be a group represented by one of Formulae 1-1 to 1-6:

[0106]

[0107] wherein, in Formulae 1-1 to 1-6,

[0108] M1, A1to A3, Y1to Y3, L1to L3, a1to a3, R1to R3, and b1to b3 are each independently the same as respectively described above,

[0109] A 21 is the same as described in connection with A1,

[0110] R a to R k and R21 each independently the same as described in connection with R1, and

[0111] b21 is the same as described in connection with b1.

[0112] For example, A 21 may be a phenyl group.

[0113] For example, R a may be a C1-C 20 alkyl group substituted with at least one deuterium, a C6-C 20 aryl group, or a C6-C 20 aryl group substituted with at least one C6-C 20 aryl group substituted with at least one deuterium.

[0114] In embodiments, the organometallic compound represented by Formula 1 can be represented by Formula 1A:

[0115] Formula 1A

[0116]

[0117] wherein, in Formula 1A,

[0118] M1, A1, A3, Y1, Y3, L2, and L3, L 11 and L 12 , a11 and a12, R1, R3, b1 and b3 are each independently the same as described above,

[0119] X 31 and X 32 may each independently be N or C(R 32 ),

[0120] A 31 is the same as described in connection with A1,

[0121] R 4a through R 4e , R 31 and R 32 are each independently the same as described in connection with R1, and

[0122] b31 is the same as described in connection with b1.

[0123] In embodiments, the organometallic compound represented by Formula 1 can include at least one deuterium.

[0124] In embodiments, the organometallic compound represented by Formula 1 can include at least one selected from a C1-C 20 alkyl group substituted with at least one deuterium, and a C6-C 20 aryl group substituted with at least one deuterium.

[0125] In an embodiment, the organometallic compound represented by Formula 1 can be selected from Compound 1 to Compound 44, but embodiments of the present disclosure are not limited thereto:

[0126]

[0127]

[0128]

[0129]

[0130] Because, in the organometallic compound represented by Formula 1, the carbene ligand connected to the central metal (M1 in Formula 1) includes a bridged structure, the binding force between the central metal and the carbene ligand is enhanced, and thus the rigidity of the organometallic compound can be improved. Accordingly, the lifespan characteristics of the organic light emitting device using the organometallic compound can be improved.

[0131] In addition, because one or more deuteriums are included in the organometallic compound represented by Formula 1, the intermolecular vibration mode is reduced, so that the rigidity of the organometallic compound is improved, and thus the stability of the organometallic compound is improved, and a long lifespan effect of the organic light emitting device using the organometallic compound is obtained.

[0132] In an embodiment, because, in the organometallic compound represented by Formula 1, the carbene ligand has a condensed ring structure, the binding force between the central metal and the carbene ligand is enhanced due to 3 The MC energy level increases according to an increase in the sigma electron donor effect, and the stability can be improved.

[0133] In addition, in the organometallic compound represented by Formula 1, the element of the carbene ligand connected to the central metal is carbon, and the carbene ligand has a covalent bond with the central metal rather than a coordination bond, so that the binding force is increased and the hole transport characteristics and the electron transport characteristics can be simultaneously enhanced.

[0134] As a result, when the organometallic compound is applied to the organic light emitting device, the phenomenon in which the triplet exciton is converted to a non-emitting 3 MC state due to the rupture of the ligand can be reduced or prevented, so that the stability in the excited state is appropriate (e.g., excellent), and the organic light emitting device can have appropriate (e.g., excellent) lifespan and efficiency characteristics.

[0135] In an embodiment, the organometallic compound represented by Formula 1 can satisfy the ranges of E 3MC described above. Meanwhile, the transition of the organometallic compound represented by Formula 1 from the 3 MC LT state to the 3The possibility of MC states, which are non-emissive states, can be reduced. Thus, the stability of the organic metal compound in an excited state can be suitable (e.g., excellent), and can improve the efficiency and lifetime of an organic light emitting device including the organic metal compound.

[0136] The organic metal compound can emit blue light. For example, the organic metal compound can emit blue light having a maximum emission wavelength of about 440 nm or more and about 490 nm or less (bottom emission CIE x,y color coordinates X = 0.13, Y = 0.05 to 0.18), but embodiments of the present disclosure are not limited thereto. Thus, the organic metal compound represented by Formula 1 can be used to manufacture an organic light emitting device that emits blue light.

[0137] A person of ordinary skill in the art can recognize a method of synthesizing the organic metal compound represented by Formula 1 by referring to examples provided below.

[0138] At least one of such organic metal compounds represented by Formula 1 can be used between a pair of electrodes of an organic light emitting device. In embodiments, the organic metal compound can be included in an emission layer. The organic metal compound included in the emission layer can be used as a dopant. In one or more embodiments, the organic metal compound of Formula 1 can be used as a material for a cap layer located outside a pair of electrodes of an organic light emitting device.

[0139] Thus, according to another embodiment of the present disclosure, an organic light emitting device includes a first electrode; a second electrode facing the first electrode; an organic layer located between the first electrode and the second electrode; and at least one organic metal compound represented by Formula 1. For example, the organic layer includes at least one of the organic metal compounds.

[0140] The expression “(an organic layer) includes at least one of the organic metal compounds” as used herein can include a case in which “(an organic layer) includes the same organic metal compound represented by Formula 1” and a case in which “(an organic layer) includes two or more different organic metal compounds represented by Formula 1”.

[0141] For example, the organic layer can include the organic metal compound, and can include only Compound 1. In this embodiment, Compound 1 can be included in an emission layer of the organic light emitting device. In one or more embodiments, the organic layer can include Compound 1 and Compound 2 as the organic metal compounds. In this regard, Compound 1 and Compound 2 can exist in the same layer (e.g., both Compound 1 and Compound 2 can exist in the emission layer), or can exist in different layers (e.g., Compound 1 can exist in the emission layer, and Compound 2 can exist in an electron transport region).

[0142] In some embodiments,

[0143] The first electrode of the organic light emitting device can be an anode,

[0144] The second electrode of the organic light emitting device can be a cathode, and

[0145] The organic layer further includes a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,

[0146] The hole transport region includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and

[0147] The electron transport region can include a buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0148] The term "organic layer" as used herein refers to a single layer and / or a multi-layer between the first electrode and the second electrode of the organic light emitting device. The materials included in the "organic layer" are not limited to organic materials.

[0149] In an embodiment, the emission layer includes the organometallic compound represented by Formula 1, the emission layer further includes a host, and the amount of the host of the emission layer can be greater than the amount of the organometallic compound in the emission layer.

[0150] In an embodiment, the emission layer can further include a host, and the amount of the organometallic compound can be 0.1 parts by weight to 50 parts by weight, based on 100 parts by weight of the emission layer.

[0151] In an embodiment, the hole transport region can include a p-dopant having a lowest unoccupied molecular orbital (LUMO) energy level of less than about -3.5 eV.

[0152] Figure 1 Description of Drawings

[0153] Figure 1 is a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment. The organic light emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.

[0154] Hereinafter, the structure of the organic light emitting device 10 according to an embodiment and a method of manufacturing the organic light emitting device 10 will be described with reference to Figure 1

[0155] The first electrode 110

[0156] In Figure 1 ​In the meantime, the substrate can additionally be located under the first electrode 110 or over the second electrode 190. The substrate can be a glass substrate or a plastic substrate each having suitable (e.g., excellent) mechanical strength, thermal stability, transparency, surface flatness, handleability, and water resistance.

[0157] The first electrode 110 can be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 can be selected from materials having a high work function to facilitate hole injection.

[0158] The first electrode 110 can be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material for forming 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, although embodiments of the present disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material for forming 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, although embodiments of the present disclosure are not limited thereto.

[0159] The first electrode 110 can have a single layer structure or a multi-layer structure including two or more layers. For example, the first electrode 110 can have a three-layer structure of ITO / Ag / ITO, although the structure of the first electrode 110 is not limited thereto.

[0160] The organic layer 150

[0161] The organic layer 150 is located on the first electrode 110. The organic layer 150 can include an emission layer.

[0162] The organic layer 150 can further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 190.

[0163] The hole transport region in the organic layer 150

[0164] The hole transport region can have: i) a single layer structure including (e.g., consisting of) a single material; ii) a single layer structure including a plurality of different materials; or iii) a multi-layer structure having a plurality of layers including a plurality of different materials.

[0165] The hole transport region can include at least one layer selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer.

[0166] In an embodiment, the hole transport region can have a single layer structure including a plurality of different materials or a multi-layer structure having 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, in which, for each structure, the constituent layers are sequentially stacked in the order of the respective recitations from the first electrode 110, but the structure of the hole transport region is not limited thereto.

[0167] The hole transport region can 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), a compound represented by Formula 201, and a compound represented by Formula 202:

[0168]

[0169] Formula 201

[0170]

[0171] Formula 202

[0172]

[0173] In Formula 201 and Formula 202,

[0174] L 201 to L 204 may each be independently selected from substituted or unsubstituted C3-C 10 cycloalkylene, substituted or unsubstituted C1-C 10 heterocycloalkylene, substituted or unsubstituted C3-C 10 cycloalkenylene, substituted or unsubstituted C1-C 10 heterocycloalkenylene, substituted or unsubstituted C6-C 60 arylene, substituted or unsubstituted C1-C 60 heteroarylene, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0175] L 205may be selected from the group consisting of *-O-*, *-S-*, *-N(Q 201 )-*, substituted or unsubstituted C1-C 20 alkylene, substituted or unsubstituted C2-C 20 alkenylene, substituted or unsubstituted C3-C 10 cycloalkylene, substituted or unsubstituted C1-C 10 heterocycloalkylene, substituted or unsubstituted C3-C 10 cycloalkenylene, substituted or unsubstituted C1-C 10 heterocycloalkenylene, substituted or unsubstituted C6-C 60 arylene, substituted or unsubstituted C1-C 60 heteroarylene, substituted or unsubstituted bivalent non-aromatic condensed polycyclic group and substituted or unsubstituted bivalent non-aromatic condensed heteropolycyclic group,

[0176] xa1to xa4may each independently be an integer of 0 to 3,

[0177] xa5may be an integer of 1 to 10, and

[0178] R 201 to R 204 and Q 201 may each independently be selected from the group consisting of substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, 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 non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0179] For example, R 201 and R 202 may be optionally connected to each other via a single bond, dimethyl-methylene or diphenyl-methylene, and R 203 and R 204 may be optionally connected to each other via a single bond, dimethyl-methylene or diphenyl-methylene.

[0180] In an embodiment, in Formula 201 and Formula 202,

[0181] L 201 to L 205Each can be independently selected from:

[0182] 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

[0183] 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.

[0184] 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.

[0185] In one or more embodiments, xa1 to xa4 can each be independently 0, 1 or 2.

[0186] In one or more embodiments, xa5 can be 1, 2, 3 or 4.

[0187] 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

[0188] 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: 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.

[0189] Among them, Q 31 To Q 33 Each can be independently identical to the description above.

[0190] 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:

[0191] Fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl and dibenzothiopheneyl; and

[0192] 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.

[0193] However, the embodiments disclosed herein are not limited thereto.

[0194] In one or more embodiments, in formula 202, i)R 201 and R 202They 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.

[0195] In one or more embodiments, R in formula 202 201 To R 204 At least one of them can be selected from:

[0196] Carbazolyl; and

[0197] 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.

[0198] However, the embodiments disclosed herein are not limited thereto.

[0199] In one or more embodiments, the compound represented by formula 201 can be represented by the following formula 201A:

[0200] Formula 201A

[0201]

[0202] 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:

[0203] Formula 201A(1)

[0204]

[0205] 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:

[0206] Formula 201A-1

[0207]

[0208] In one or more embodiments, the compound represented by formula 202 can be represented by the following formula 202A:

[0209] Formula 202A

[0210]

[0211] In one or more embodiments, the compound represented by formula 202 can be represented by the following formula 202A-1:

[0212] Formula 202A-1

[0213]

[0214] In Equations 201A, 201A(1), 201A-1, 202A, and 202A-1,

[0215] L 201 To L 203 xa1 to xa3, xa5 and R 202 To R 204 R can be the same as described above. 211 and R 212 They can all independently bind with R 203 The same description, and

[0216] 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.

[0217] 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:

[0218]

[0219]

[0220]

[0221] 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 selected from the hole injection layer and the 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 hole transport region, hole injection layer, and hole transport layer thickness are all within these ranges.

[0222] 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.

[0223] p-doped agent

[0224] 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.

[0225] The charge-generating material can be, for example, a p-doped agent.

[0226] In the embodiments, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of -3.5 eV or less.

[0227] 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.

[0228] In embodiments, the p-doper may include at least one selected from the following compounds:

[0229] Quinone derivatives, such as tetracyanoquinone dimethyl ether (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl ether (F4-TCNQ);

[0230] Metal oxides, such as tungsten oxide and / or molybdenum oxide;

[0231] 1,4,5,8,9,12-hexaazabenzophenanthrene-hexanitrile (HAT-CN); and

[0232] The compound represented by the following formula 221,

[0233] However, the embodiments disclosed herein are not limited thereto:

[0234]

[0235]

[0236] Equation 221

[0237]

[0238] In Equation 221,

[0239] R 221 To R 223 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.

[0240] Emission layer in organic layer 150

[0241] 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.

[0242] The emitting layer may include a host and a dopant. The dopant may include at least one selected from phosphorescent dopant and fluorescent dopant. The phosphorescent dopant may include an organometallic compound represented by Formula 1.

[0243] 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.

[0244] The thickness of the emission layer can be approximately to approximately (For example, about to approximately Within these ranges, suitable (e.g., excellent) light-emitting characteristics can be obtained without significantly increasing the driving voltage when the thickness of the emitting layer is within these ranges.

[0245] The main body in the emission layer

[0246] In one or more embodiments, the body may include a compound represented by the following formula 301.

[0247] Formula 301

[0248] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21

[0249] In Equation 301,

[0250] Ar 301 C5-C can be substituted or unsubstituted. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group,

[0251] xb11 can be 1, 2, or 3.

[0252] 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 Hybrid aryl groups, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups, and substituted or unsubstituted divalent non-aromatic condensed heterocyclic groups.

[0253] xb1 can be an integer from 0 to 5.

[0254] 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-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 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

[0255] xb21 can be an integer from 1 to 5.

[0256] 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.

[0257] In the embodiment, Ar in formula 301 301 It can be selected from:

[0258] 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

[0259] 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,

[0260] 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.

[0261] When xb11 in equation 301 is two or greater, two or more Ar 301 It can be connected via a single key.

[0262] In one or more embodiments, the compound represented by formula 301 may be represented by one of formulas 301-1 and 301-2:

[0263] Formula 301-1

[0264]

[0265] Formula 301-2

[0266]

[0267] In Equations 301-1 and 301-2,

[0268] 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.

[0269] X 301 It can be O, S or N-[(L 304 ) xb4 -R 304 ],

[0270] R 311 To R 314 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, 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 ),

[0271] xb22 and xb23 can each be independently 0, 1, or 2.

[0272] L 301 xb1, R 301 and Q 31 To Q 33 Each of them can be independently identical to the ones described above.

[0273] L 302 To L 304 They can all independently bind with L 301 The descriptions are the same.

[0274] xb2 to xb4 can all be independently identical to those described in conjunction with xb1, and

[0275] R 302 To R 304 They can all independently bind with R 301 The descriptions are the same.

[0276] For example, L in Equations 301, 301-1, and 301-2 301 To L 304 Each can be independently selected from:

[0277] 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

[0278] 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) 32 The 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, phenanthreneridinyl, acridineyl, phenanthrene-pyridinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl,

[0279] Among them, Q 31 To Q 33 Each can be independently identical to the description above.

[0280] In the embodiments, R in Equations 301, 301-1, and 301-2 301 To R 304Each can be independently selected from:

[0281] 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

[0282] 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: 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.

[0283] Among them, Q 31 To Q 33 Each can be independently identical to the description above.

[0284] 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.

[0285] 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 compounds H1 to H55, but the embodiments of this disclosure are not limited thereto:

[0286]

[0287]

[0288]

[0289] In embodiments, the body may include at least one selected from silicon-containing compounds (e.g., BCPDS used in the examples below) and phosphine oxide-containing compounds (e.g., POPCPA used in the examples below).

[0290] The body may include only one compound or may include two or more compounds that are different from each other (e.g., the body in the example below includes BCPDS and POPCPA). In one or more embodiments, the body may alternatively have various suitable modifications.

[0291] Phosphorescent dopants in the emission layer of organic layer 150

[0292] Phosphorescent dopants may include organometallic compounds represented by Formula 1.

[0293] In addition, phosphorescent dopants may include organometallic complexes represented by the following formula 401:

[0294] Formula 401

[0295] M(L 401 ) xc1 (L 402 ) xc2

[0296] Formula 402

[0297]

[0298] In Equations 401 and 402,

[0299] 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).

[0300] L 401 The ligand can be represented by Equation 402, where xc1 can be 1, 2, or 3, and when xc1 is two or more, two or more L... 401 They can be the same or different from each other.

[0301] L 402 It can be an organic ligand, and xc2 can be an integer from 0 to 4, where when xc2 is two or greater, two or more L... 402 They can be the same or different from each other.

[0302] X 401 To X 404 They can each be nitrogen or carbon independently.

[0303] 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.

[0304] A 401 and A402 Each can be independently selected from C5-C 60 Carbocyclic or C1-C 60 Heterocyclic group,

[0305] 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,

[0306] X 406 It can be a single bond, O, or S.

[0307] 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,

[0308] xc11 and xc12 can both be independent integers from 0 to 10, and

[0309] In Equation 402, * and *' both represent the binding position with M in Equation 401.

[0310] In the embodiment, A in formula 402 401 and A 402 They 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.

[0311] 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.

[0312] In one or more embodiments, R in Formula 402 401 and R 402 Each can be independently selected from:

[0313] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 Alkoxy;

[0314] 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 20Alkoxy;

[0315] Cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiophenyl;

[0316] 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 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

[0317] -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 ),

[0318] 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.

[0319] In one or more embodiments, when xc1 in equation 401 is two 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 408They 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 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl or naphthyl), but the embodiments disclosed herein are not limited thereto.

[0320] L in Equation 401 402 It can be a monovalent, divalent, or trivalent organic ligand. For example, 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.

[0321] 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:

[0322]

[0323] Fluorescent dopants in the emission layer

[0324] Fluorescent dopants may include arylamine compounds or styreneamine compounds. Fluorescent dopants may include compounds represented by the following formula 501.

[0325] Formula 501

[0326]

[0327] In Equation 501,

[0328] Ar 501 C5-C can be substituted or unsubstituted. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group,

[0329] L 501 To L 503 Each can be independently selected from substituted or unsubstituted C3-C. 10Cycloalkylene, 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 nonaromatic condensed polycyclic groups and substituted or unsubstituted divalent nonaromatic condensed heterocyclic groups,

[0330] xd1 to xd3 can each be an independent integer from 0 to 3.

[0331] 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

[0332] xd4 can be an integer from 1 to 6.

[0333] In the embodiment, Ar in formula 501 501 It can be selected from:

[0334] 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

[0335] 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.

[0336] In one or more embodiments, L in Formula 501 501 To L 503 Each can be independently selected from:

[0337] 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

[0338] 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.

[0339] In one or more embodiments, R in Formula 501 501 and R 502 Each can be independently selected from:

[0340] 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

[0341] 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, 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.

[0342] 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.

[0343] In one or more embodiments, xd4 in Formula 501 can be 2, but the embodiments of this disclosure are not limited thereto.

[0344] For example, fluorescent dopants can be selected from compounds FD1 to FD22:

[0345]

[0346]

[0347]

[0348] 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.

[0349]

[0350] Electron transport region in organic layer 150

[0351] The electron transport region may have: i) a single-layer structure comprising a single material (e.g., composed of a single material); ii) a single-layer structure comprising multiple different materials; or iii) a multi-layer structure having multiple layers comprising multiple different materials.

[0352] 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.

[0353] For example, 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 stacked sequentially from the emitter layer in the order stated herein. However, embodiments of the electron transport region structure are not limited to these.

[0354] 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-depleted nitrogen-containing ring.

[0355] "π-electron-poor nitrogen-containing rings" refer to C1-C rings with at least one *-N=*' moiety as the cyclic component. 60 Heterocyclic group.

[0356] 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.

[0357] 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.

[0358] For example, the electron transport region may include a compound represented by the following formula 601:

[0359] Formula 601

[0360] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21

[0361] In Equation 601,

[0362] Ar 601 C5-C can be substituted or unsubstituted. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group,

[0363] xe11 can be 1, 2, or 3.

[0364] 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 nonaromatic condensed polycyclic groups and substituted or unsubstituted divalent nonaromatic condensed heterocyclic groups,

[0365] xe1 can be an integer from 0 to 5.

[0366] 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 ),

[0367] Q 601 To Q 603 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, and

[0368] xe21 can be an integer from 1 to 5.

[0369] In the 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.

[0370] In the embodiment, Ar in formula 601 601 It can be selected from:

[0371] 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

[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 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,

[0373] 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.

[0374] 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.

[0375] In one or more embodiments, Ar in Formula 601 601 It can be an anthracene group.

[0376] In one or more embodiments, the compound represented by formula 601 can be represented by formula 601-1:

[0377] Formula 601-1

[0378]

[0379] In Equation 601-1,

[0380] 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,

[0381] L 611 To L 613 They can all independently bind with L 601 The descriptions are the same.

[0382] xe611 to xe613 can all be independently identical to those described in conjunction with xe1.

[0383] R 611 To R 613 They can all independently bind with R 601 The descriptions are the same, and

[0384] 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.

[0385] In the embodiment, L in formula 601 601 L in Equation 601-1 611 To L 613 Each can be independently selected from:

[0386] 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

[0387] 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,

[0388] However, the embodiments disclosed herein are not limited thereto.

[0389] 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.

[0390] 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:

[0391] 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;

[0392] 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

[0393] -S(=O)2(Q 601 ) and -P(=O)(Q 601 (Q) 602 ),

[0394] Among them, Q 601 and Q 602 Each can be independently identical to the description above.

[0395] 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:

[0396]

[0397]

[0398]

[0399]

[0400] In one or more embodiments, the electron transport region may include at least one 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:

[0401]

[0402] 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 some embodiments, 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.

[0403] 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, suitable (e.g., excellent) hole blocking characteristics or suitable (e.g., 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.

[0404] The thickness of the electron transport layer can be approximately to approximately (For example, about to approximately Within the range described above, the electron transport layer can exhibit satisfactory electron transport characteristics without significantly increasing the driving voltage.

[0405] In addition to the materials described above, the electron transport region (e.g., the electron transport layer in the electron transport region) may also include metallic materials.

[0406] The metal-containing material may include at least one selected from alkali metal complexes and alkaline earth metal complexes. Alkali metal complexes may include metal ions selected from Li, Na, K, Rb, and Cs ions, while alkaline earth metal complexes may include metal ions selected from Be, Mg, Ca, Sr, and Ba ions. The ligands coordinated to the metal ions of the alkali metal or alkaline earth metal complexes may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, and cyclopentadiene, but the embodiments disclosed herein are not limited thereto.

[0407] For example, metallic materials may include Li complexes. Li complexes may include, for example, compounds ET-D1 (lithium hydroxyquinoline, LiQ) or ET-D2:

[0408]

[0409] 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.

[0410] The electron injection layer can have: i) a single-layer structure comprising a single material (e.g., composed of a single material); ii) a single-layer structure comprising multiple different materials; or iii) a multi-layer structure having multiple layers comprising multiple different materials.

[0411] 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.

[0412] The alkali metal can be selected from Li, Na, K, Rb, and Cs. In the embodiments, 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.

[0413] Alkaline earth metals can be selected from Mg, Ca, Sr and Ba.

[0414] Rare earth metals can be selected from Sc, Y, Ce, Tb, Yb and Gd.

[0415] Alkali metal compounds, alkaline earth metal compounds, and rare earth metal compounds may be selected from oxides and halides of alkali metals, alkaline earth metals, and rare earth metals (e.g., fluorides, chlorides, bromides, or iodides).

[0416] The alkali metal compound can 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 an embodiment, the alkali metal compound can be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, but the embodiments of the present disclosure are not limited thereto.

[0417] The alkaline earth metal compound can 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 an embodiment, the alkaline earth metal compound can be selected from BaO, SrO, and CaO, but the embodiments of the present disclosure are not limited thereto.

[0418] The rare earth metal compound can be selected from YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, and TbF3. In an embodiment, the rare earth metal compound can be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but the embodiments of the present disclosure are not limited thereto.

[0419] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex can include ions of alkali metals, alkaline earth metals, and rare earth metals as described above, and the ligands coordinated with the metal ions of the alkali metal complex, alkaline earth metal complex, or rare earth metal complex can 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.

[0420] 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, 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 comprising organic materials.

[0421] The thickness of the electron injection layer can be approximately to approximately (For example, about to approximately Within the range described above, the electron injection layer can exhibit satisfactory electron injection characteristics without significantly increasing the driving voltage.

[0422] Second electrode 190

[0423] The second electrode 190 is located on the organic layer 150 having such a structure. The second electrode 190 can be a cathode serving as an electron injection electrode. In this respect, the material used to form the second electrode 190 can be selected from metals, alloys, conductive compounds, and combinations thereof, all of which have relatively low work functions.

[0424] 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), ytterbium (Yb), silver-ytterbium (Ag-Yb), 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.

[0425] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.

[0426] Figures 2 to 4 Description

[0427] 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.

[0428] about Figures 2 to 4 The first electrode 110, the organic layer 150, and the second electrode 190 can be combined by reference. Figure 1 Use the given description to understand.

[0429] In each of the organic light-emitting devices 20 and 40, the light generated in the emission layer of the organic layer can pass outward through the first electrode 110, which serves as a semi-transparent electrode or a transmissive electrode, and the first capping layer 210. In each of the organic light-emitting devices 30 and 40, the light generated in the emission layer of the organic layer of the organic layer 150 can pass outward through the second electrode 190, which serves as a semi-transparent electrode or a transmissive electrode, and the second capping layer 220.

[0430] The first capping layer 210 and the second capping layer 220 can improve the external luminous efficiency according to the principle of constructive interference. Therefore, the light extraction efficiency of the organic light-emitting device 10 is improved, which makes the luminous efficiency of the organic light-emitting device 10 better.

[0431] Each of the first capping layer 210 and the second capping layer 220 may include a material having a refractive index of 1.6 or greater (at 589 nm).

[0432] The first capping layer 210 and the second capping layer 220 can improve the external luminescence efficiency according to the principle of constructive interference.

[0433] The first capping layer 210 and the second capping layer 220 can each be independently an organic capping layer including organic materials, an inorganic capping layer including inorganic materials, or a composite capping layer including both organic and inorganic materials.

[0434] 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 embodiments, at least one of the first capping layer 210 and the second capping layer 220 may each independently comprise an amine compound.

[0435] In an embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include a compound represented by formula 201 or a compound represented by formula 202.

[0436] 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, compounds CP1 to CP6, and β-NPB, but the embodiments of this disclosure are not limited thereto.

[0437]

[0438] 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.

[0439] 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-Blodget (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.

[0440] 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].

[0441] 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.

[0442] General definition of substituents

[0443] 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.

[0444] 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.

[0445] 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.

[0446] 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.

[0447] 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.

[0448] 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.

[0449] 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.

[0450] 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.

[0451] 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.

[0452] 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 dibenzothiopheneyl. When C1-C 60 heteroaryl and C1-C 60When each heteroaryl group comprises two or more rings, the two or more rings may condense together.

[0453] 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 -SA 103 (where A) 103 For C6-C 60 (aryl) represents a group.

[0454] 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.

[0455] 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 the 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 carbazolyl and 9H-xanthonyl. 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.

[0456] As used here, the term "C5-C" 60 "Carbocyclic group" refers to a monocyclic or polycyclic group that includes only carbon atoms as cyclic atoms and comprises 5 to 60 carbon 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.

[0457] As used here, the term "C1-C" 60A "heterocyclic group" refers to a group that, in addition to carbon (the number of carbon atoms can range from 1 to 60), uses at least one heteroatom selected from N, O, Si, P, and S as the cyclic atom, and is cyclic with C5-C6. 60 Carbon cyclic groups are groups with the same structure.

[0458] 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-C 10 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 Arylthio, substituted C1-C 60 heteroaryl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 At least one substituent among heteroarylsulfo, substituted monovalent nonaromatic condensed polycyclic group, and substituted monovalent nonaromatic condensed heterocyclic group may be selected from:

[0459] 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;

[0460] 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-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;

[0461] 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;

[0462] 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 Alkyne 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-C60 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

[0463] -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 ),

[0464] Among them, Q1 to Q3, 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 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C10 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, -Cl, -Br, -I and cyano. 60 Alkyl groups, substituted with at least one of deuterium, -F, -Cl, -Br, -I, and cyano groups, are C6-C. 60 Aryl, biphenyl, and terphenyl.

[0465] As used herein, the term "Ph" refers to phenyl, "Me" refers to methyl, "Et" refers to ethyl, and "tert-Bu" or "Bu" refers to... t "Refers to tert-butyl, as the term "OMe" used here refers to methyl methacrylate (MMA).

[0466] 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.

[0467] 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.

[0468] Unless otherwise defined, * and *' as used here refer to the bonding sites with adjacent atoms in the corresponding formula.

[0469] 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 describing the synthesis examples means using the same molar equivalent of B instead of the same molar equivalent of A.

[0470] Synthesis Example

[0471] Synthesis Example 1: Synthesis of Compound 1

[0472]

[0473] Synthesis of intermediate compound 1-A

[0474] 1,3-Diacetylimidazolin-2-one (1.0 equivalent) and cyclopentadiene (1.0 mol, 10 equivalent) were dissolved in m-xylene and stirred at 150 °C for 72 h. After depressurization, n-hexane was added to the reaction mixture, and the precipitate was removed by filtration. The filtered precipitate was dissolved in MeOH (250 mL) and 2 M HCl (250 mL), stirred at room temperature for 30 min, and then subjected to depressurization. The reaction mixture was extracted with water and dichloromethane to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated to synthesize intermediate compound 1-A (yield 54%).

[0475] Synthesis of intermediate compound 1-B

[0476] Under Ar conditions (e.g., in an inert Ar atmosphere), 20 mL of a solution of 10% Pd / C (70 mg) in ethyl acetate (EtOAc) was added to dissolve intermediate compound 1-A (30 mmol) in a solution of EtOAc (20 mL). After filling with hydrogen, the mixture was stirred for 1 hour at room temperature. The reaction mixture was washed with EtOAc and filtered through diatomaceous earth. The filtrate was concentrated to obtain intermediate compound 1-B (99% yield).

[0477] Synthesis of intermediate compound 1-C

[0478] Intermediate compound 1-B (2.0 equivalents) was dissolved in MeOH and dichloromethane and stirred at room temperature. After adding NaH (60% in mineral oil, 1.0 equivalents) at 0°C, the resulting mixture was stirred at room temperature for 4 hours. Following cold maceration with NH4Cl solution at 0°C, an extraction process was performed using water and dichloromethane. The obtained organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized with n-hexane to synthesize intermediate compound 1-C (93% yield).

[0479] Synthesis of intermediate compound 1-D

[0480] Intermediate compound 1-C (1.0 eq), iodomethane-d3 (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 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-D (yield: 75%).

[0481] Synthesis of intermediate compound 1-E

[0482] Intermediate compound 1-D (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 water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and intermediate compound 1-E (yield: 78%) was obtained by column chromatography (ethyl acetate:hexane = 1:9).

[0483] Synthesis of intermediate compound 1-F

[0484] Intermediate compound 1-E (3.5 mmol) was dissolved in tetrahydrofuran (THF) and stirred at room temperature. LiAlH4 (7 mmol) was added at 0 °C, followed by stirring at 50 °C for 2 hours. THF, NaOH solution, and H2O were added to the reaction mixture at 0 °C, and the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was filtered through diatomaceous earth / silica gel using THF and EtOAc under reduced pressure. The reaction mixture (1.0 eq) was dissolved in triethyl orthoformate (30 eq) at 80 °C, followed by the addition of 37% HCl (1.5 eq), and stirred at 80 °C for 12 hours. After cooling at room temperature, the triethyl orthoformate was concentrated (e.g., a triethyl orthoformate solution) and 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 (MC, MC: 5 vol% methanol) was used to obtain intermediate compound 1-F (yield: 87%).

[0485] Synthesis of intermediate compound 1-G

[0486] Intermediate compound 1-F (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 3 to 12 hours. After washing with distilled water and filtering to obtain a solid, it was extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated to synthesize intermediate compound 1-G (yield 96%).

[0487] Synthesis of Compound 1

[0488] Intermediate compound 1-G (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 then stirred at 120 °C under nitrogen conditions (e.g., under a nitrogen inert atmosphere) for 4 days. The reaction mixture was cooled to room temperature and then extracted three times with water to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated, and compound 1 was obtained by column chromatography (MC: 50 v / v hexane) (yield: 21%).

[0489] Synthesis Example 2: Synthesis of Compound 2

[0490]

[0491] Synthesis of intermediate compound 2-A

[0492] 1,3-Diacetylimidazolin-2-one (1.0 equivalent) and cyclopentadiene (1.0 mol, 10 equivalent) were dissolved in m-xylene and stirred at 150 °C for 72 h. After depressurization, n-hexane was added to the reaction mixture, and the precipitate was removed by filtration. The filtered precipitate was dissolved in MeOH (250 mL) and 2 M HCl (250 mL), stirred at room temperature for 30 min, and then subjected to depressurization. The reaction mixture was extracted with water and dichloromethane to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated to synthesize intermediate compound 2-A (yield 53%).

[0493] Synthesis of intermediate compound 2-B

[0494] Under Ar conditions (e.g., in an inert Ar atmosphere), 20 mL of a 10% Pd / C (70 mg) EtOAc solution was added to dissolve intermediate compound 2-A (30 mmol) in a solution of EtOAc (20 mL). After filling with hydrogen, the mixture was stirred for 1 hour at room temperature. The reaction mixture was washed with EtOAc and filtered through diatomaceous earth. The filtrate was concentrated to obtain the synthesized intermediate compound 2-B (99% yield).

[0495] Synthesis of intermediate compound 2-C

[0496] Intermediate compound 2-B (2.0 equivalents) was dissolved in MeOH and dichloromethane and stirred at room temperature. After adding NaH (60% in mineral oil, 1.0 equivalents) at 0°C, the resulting mixture was stirred at room temperature for 4 hours. Following cold maceration with NH4Cl solution at 0°C, an extraction process was performed using water and dichloromethane. The obtained organic layer was dried using anhydrous magnesium sulfate, concentrated, and recrystallized from n-hexane to synthesize intermediate compound 2-C (91% yield).

[0497] Synthesis of intermediate compound 2-D

[0498] Intermediate compound 2-C (1.0 eq), iodomethane-d3 (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 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 2-D (yield: 75%).

[0499] Synthesis of intermediate compound 2-E

[0500] Intermediate compound 2-D (1.2 eq), 2-(3-bromophenoxy)-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 water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and intermediate compound 2-E (yield: 78%) was obtained by column chromatography (ethyl acetate:hexane = 1:9).

[0501] Synthesis of intermediate compound 2-F

[0502] Intermediate compound 2-E (3.5 mmol) was dissolved in THF and stirred at room temperature. LiAlH4 (7 mmol) was added at 0 °C, followed by stirring at 50 °C for 2 hours. After adding THF, NaOH solution, and H2O to the reaction mixture at 0 °C, the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was filtered through diatomaceous earth / silica gel using THF and EtOAc under reduced pressure. After dissolving the reaction mixture (1.0 eq) in triethyl orthoformate (30 eq) at 80 °C, 37% HCl (1.5 eq) was added, and the mixture was stirred at 80 °C for 12 hours. After cooling at room temperature, the triethyl orthoformate was concentrated (e.g., a triethyl orthoformate solution) and 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 intermediate compound 2-F (yield: 87%) was obtained by column chromatography (MC, MC: 5 vol% methanol).

[0503] Synthesis of intermediate compound 2-G

[0504] Intermediate compound 2-F (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 to 12 hours. After washing with distilled water and filtering to obtain a solid, it was extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated to synthesize intermediate compound 2-G (yield 93%).

[0505] Synthesis of Compound 2

[0506] Intermediate compound 2-G (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 then stirred at 120 °C under nitrogen conditions (e.g., under a nitrogen inert atmosphere) for 4 days. The reaction mixture was cooled to room temperature and then extracted three times with water to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated, and compound 2 (yield: 18%) was obtained by column chromatography (MC: 50 v / v hexane).

[0507] Synthesis Example 3: Synthesis of Compound 4

[0508]

[0509] Synthesis of intermediate compound 4-D

[0510] Intermediate compound 1-C (1.0 eq), bromobenzene-d5 (2.0 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 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 4-D (yield: 77%).

[0511] Synthesis of intermediate compound 4-E

[0512] Intermediate compound 4-D (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 water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and intermediate compound 4-E (yield: 70%) was obtained by column chromatography (ethyl acetate:hexane = 1:9).

[0513] Synthesis of intermediate compound 4-F

[0514] Intermediate compound 4-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 3 to 12 hours. After washing with distilled water and filtering to obtain a solid, it was extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated to synthesize intermediate compound 4-F (yield 93%).

[0515] Synthesis of Compound 4

[0516] 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 then stirred at 120 °C under nitrogen conditions (e.g., under a nitrogen inert atmosphere) for 4 days. The reaction mixture was cooled to room temperature and then extracted three times with water to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated, and compound 4 was obtained by column chromatography (MC: 50 v / v hexane) (yield: 19%).

[0517] Synthesis Example 4: Synthesis of Compound 5

[0518]

[0519] Synthesis of intermediate compound 5-E

[0520] Intermediate compound 4-D (1.2 eq), 2-(3-bromophenoxy)-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 water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and intermediate compound 5-E (yield: 68%) was obtained by column chromatography (ethyl acetate:hexane = 1:9).

[0521] Synthesis of intermediate compound 5-F

[0522] Intermediate compound 5-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 to 12 hours. After washing with distilled water and filtering to obtain a solid, it was extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated to synthesize intermediate compound 5-F (yield 93%).

[0523] Synthesis of Compound 5

[0524] Intermediate compound 5-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 then stirred at 120 °C under nitrogen conditions (e.g., under a nitrogen inert atmosphere) for 4 days. The reaction mixture was cooled to room temperature and then extracted three times with water to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated, and compound 5 was obtained by column chromatography (MC: 50 v / v hexane) (yield: 17%).

[0525] Synthesis Example 5: Synthesis of Compound 7

[0526]

[0527] Synthesis of intermediate compound 7-A

[0528] Intermediate compound 1-C (1.0 eq), 2,6-diphenyl-d10-aniline (2.0 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 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-A (yield: 74%).

[0529] Synthesis of intermediate compound 7-B

[0530] Intermediate compound 7-A (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 water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and intermediate compound 7-B (yield: 72%) was obtained by column chromatography (ethyl acetate:hexane = 1:9).

[0531] Synthesis of intermediate compound 7-C

[0532] Intermediate compound 7-B (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 3 to 12 hours. After washing with distilled water and filtering to obtain a solid, it was extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated to synthesize intermediate compound 7-C (yield 93%).

[0533] Synthesis of Compound 7

[0534] Intermediate compound 7-C (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 then stirred at 120 °C under nitrogen conditions (e.g., under a nitrogen inert atmosphere) for 4 days. The reaction mixture was cooled to room temperature and then extracted three times with water to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated, and compound 7 was obtained by column chromatography (MC: 50 v / v hexane) (yield: 17%).

[0535] Synthesis Example 6: Synthesis of Compound 8

[0536]

[0537] Synthesis of intermediate compound 8-A

[0538] Intermediate compound 7-A (1.2 eq), 2-(3-bromophenoxy)-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 water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and intermediate compound 8-A (yield: 70%) was obtained by column chromatography (ethyl acetate:hexane = 1:9).

[0539] Synthesis of intermediate compound 8-B

[0540] Intermediate compound 8-A (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 to 12 hours. After washing with distilled water and filtering to obtain a solid, it was extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated to synthesize intermediate compound 8-B (yield 93%).

[0541] Synthesis of Compound 8

[0542] Intermediate compound 8-B (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 then stirred at 120 °C under nitrogen conditions (e.g., under a nitrogen inert atmosphere) for 4 days. The reaction mixture was cooled at room temperature and then extracted three times with water to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated, and compound 8 (yield: 18%) was obtained by column chromatography (MC 30 v / v: hexane).

[0543] Synthesis Example 7: Synthesis of Compound 12

[0544]

[0545] Synthesis of intermediate compound 12-A

[0546] 1,3-Diacetylimidazolin-2-one (1.0 equivalent) and cyclopentadiene (1.0 mol, 10 equivalent) were dissolved in m-xylene and stirred at 150 °C for 72 h. After depressurization, n-hexane was added to the reaction mixture, and the precipitate was removed by filtration. The filtered precipitate was dissolved in MeOH (250 mL) and 2M HCl (250 mL), stirred at room temperature for 30 min, and then subjected to depressurization. The reaction mixture was extracted with water and dichloromethane to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated to synthesize an intermediate compound. The intermediate compound was dissolved in MeOH and dichloromethane and stirred at room temperature. After adding NaH (60% in mineral oil, 1.0 equivalent) at 0 °C, the resulting mixture was stirred at room temperature for 4 h. After cold maceration with NH4Cl solution at 0 °C, the extraction process was performed using water and dichloromethane. The organic layer obtained by drying with anhydrous magnesium sulfate was concentrated and recrystallized with n-hexane to synthesize intermediate compound 12-A (yield 91%).

[0547] Synthesis of intermediate compound 12-B

[0548] Intermediate compound 12-A (1.0 eq), iodomethane-d3 (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 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: 80%).

[0549] Synthesis of intermediate compound 12-C

[0550] Intermediate compound 12-B (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 water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and intermediate compound 12-C (yield: 78%) was obtained by column chromatography (ethyl acetate:hexane = 1:9).

[0551] Synthesis of intermediate compound 12-D

[0552] Intermediate compound 12-C (3.5 mmol) was dissolved in THF and stirred at room temperature. LiAlH4 (7 mmol) was added at 0 °C, followed by stirring at 50 °C for 2 hours. After adding THF, NaOH solution, and H2O to the reaction mixture at 0 °C, the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was filtered through diatomaceous earth / silica gel using THF and EtOAc under reduced pressure. After dissolving the reaction mixture (1.0 eq) in triethyl orthoformate (30 eq) at 80 °C, 37% HCl (1.5 eq) was added, and the mixture was stirred at 80 °C for 12 hours. After cooling at room temperature, the triethyl orthoformate was concentrated (e.g., a triethyl orthoformate solution) and 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 intermediate compound 12-D (yield: 87%) was obtained by column chromatography (MC, MC: 5 vol% methanol).

[0553] Synthesis of intermediate compound 12-E

[0554] Intermediate compound 12-D (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 3 to 12 hours. After washing with distilled water and filtering to obtain a solid, it was extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated to synthesize intermediate compound 12-E (yield 96%).

[0555] Synthesis of Compound 12

[0556] Intermediate compound 12-E (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 then stirred at 120 °C under nitrogen conditions (e.g., under a nitrogen inert atmosphere) for 4 days. The reaction mixture was cooled at room temperature and then extracted three times with water to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated, and compound 12 was obtained by column chromatography (MC: 50 v / v hexane) (yield: 21%).

[0557] Synthesis Example 8: Synthesis of Compound 23

[0558]

[0559] Synthesis of intermediate compound 23-A

[0560] 1,3-Diacetylimidazolin-2-one (1.0 equivalent) and 5,5-dimethylcyclopentane-1,3-diene (1.0 mol, 10 equivalent) were dissolved in m-xylene and stirred at 150 °C for 72 h. After depressurization, n-hexane was added to the reaction mixture, and the precipitate was removed by filtration. The filtered precipitate was dissolved in MeOH (250 mL) and 2 M HCl (250 mL), stirred at room temperature for 30 min, and then subjected to depressurization. The reaction mixture was extracted with water and dichloromethane to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated to synthesize intermediate compound 23-A (yield 56%).

[0561] Synthesis of intermediate compound 23-B

[0562] Under Ar conditions (e.g., in an inert Ar atmosphere), 20 mL of a 10% Pd / C (70 mg) EtOAc solution was added to dissolve intermediate compound 23-A (15 mmol) in a solution of EtOAc (10 mL). After filling with hydrogen, the mixture was stirred for 1 hour at room temperature. The reaction mixture was washed with EtOAc and filtered through diatomaceous earth. The filtrate was concentrated to obtain the synthesized intermediate compound 23-B (99% yield).

[0563] Synthesis of intermediate compound 23-C

[0564] Intermediate compound 23-B (2.0 eq) was dissolved in n-ethanol (MeOH) and dichloromethane and stirred at room temperature. After adding NaH (60% in mineral oil, 1.0 equivalent) at 0 °C, the resulting mixture was stirred at room temperature for 4 hours. Following cold maceration with NH4Cl solution at 0 °C, an extraction process was performed using water and dichloromethane. The obtained organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized with n-hexane to synthesize intermediate compound 23-C (94% yield).

[0565] Synthesis of intermediate compound 23-D

[0566] Intermediate compound 23-C (1.0 eq), iodomethane-d3 (3.0 eq), Pd2(dba)3 (2 mol%), Sphos (1 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 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 23-D (yield: 78%).

[0567] Synthesis of intermediate compound 23-E

[0568] Intermediate compound 23-D (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 water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and intermediate compound 23-E (yield: 68%) was obtained by column chromatography (ethyl acetate:hexane = 1:9).

[0569] Synthesis of intermediate compound 23-F

[0570] Intermediate compound 23-E (7.0 mmol) was dissolved in THF and stirred at room temperature. LiAlH4 (14 mmol) was added at 0 °C, followed by stirring at 50 °C for 2 hours. THF, NaOH solution, and H2O were added to the reaction mixture at 0 °C, and the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was filtered through diatomaceous earth / silica gel using THF and EtOAc under reduced pressure. The reaction mixture (1.0 eq) was dissolved in triethyl orthoformate (30 eq) at 80 °C, followed by the addition of 37% HCl (1.5 eq), and stirred at 80 °C for 12 hours. After cooling at room temperature, the triethyl orthoformate was concentrated (e.g., a triethyl orthoformate solution) and 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 intermediate compound 23-F (yield: 85%) was obtained by column chromatography (MC, MC: 5 vol% methanol).

[0571] Synthesis of intermediate compound 23-G

[0572] Intermediate compound 23-F (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 3 to 12 hours. After washing with distilled water and filtering to obtain a solid, it was extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated to synthesize intermediate compound 23-G (yield 97%).

[0573] Synthesis of Compound 23

[0574] Intermediate compound 23-G (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 then stirred at 120 °C under nitrogen conditions (e.g., under a nitrogen inert atmosphere) for 4 days. The reaction mixture was cooled to room temperature and then extracted three times with water to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated, and compound 23 was obtained by column chromatography (MC: 50 v / v hexane) (yield: 22%).

[0575] Synthesis Example 9: Synthesis of Compound 35

[0576]

[0577] Synthesis of intermediate compound 35-A

[0578] 1,4-Dihydro-1,4-methylenenaphthalene (1.00 g) was dissolved in tert-butanol (7.8 mL) and H₂O (2.3 mL). An N-methylmorpholine N-oxide solution (4.8 M, 6.4 mL, 30.7 mmol in H₂O) was added, and after about 5 minutes, an OsO₄ solution (0.02 mL, 2 wt% in water) was added, and the mixture was stirred at 60 °C for 20 hours. After cooling the reaction mixture, the solvent was removed under reduced pressure, and the organic layer was obtained by extraction with water and ethyl acetate. After washing with acetone, the resulting product was filtered to synthesize intermediate compound 35-A (yield 86%).

[0579] Synthesis of intermediate compound 35-B

[0580] Trifluoroacetic anhydride (0.62 mL, 4.50 mmol) was slowly added to dimethyl sulfoxide (DMSO), and the solution was stirred at -78 °C for 10 min. The resulting mixture was added to a solution in which intermediate compound 35-A (264 mg, 1.50 mmol) was dissolved in THF (5 mL), and the mixture was stirred at -78 °C for 2 h. After adding Et3N (1.11 mL), the resulting mixture was stirred at -78 °C for 3 h and transferred to an ice bath, where it was stirred at 0 °C. The resulting mixture was cold-soaked in NH4Cl solution (10 mL), and then extracted with water and Et2O to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated, and intermediate compound 35-B (yield: 96%) was obtained by column chromatography (30% EtOAc).

[0581] Synthesis of intermediate compound 35-C

[0582] Intermediate compound 35-B (400 mg, 1.98 mmol) was dissolved in 10 mL of MeOH, and then NaOAc (389 mg, 4.75 mmol) and NH₂OH·HCl (550 mg, 7.92 mmol) were added. The mixture was then stirred at room temperature for 4 hours. The reaction mixture was extracted with water and EtOAc to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized from it using hexane and EtOAc in a 1:1 volume ratio to synthesize intermediate compound 35-C (yield 89%).

[0583] Synthesis of intermediate compound 35-D

[0584] Intermediate compound 35-C (1.75 mmol) was dissolved in MeOH, and then NiCl2 (3.50 mmol) was added and stirred at room temperature for 10 minutes. NaBH4 (17.5 mmol) was added at 0 °C, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was subjected to reduced pressure, dissolved in dichloromethane, and filtered through a diatomaceous earth pad. After extraction with 2 M HCl and dichloromethane, the mixture was subjected to reduced pressure to obtain intermediate compound 35-D (yield: 82%).

[0585] Synthesis of intermediate compound 35-E

[0586] Intermediate compound 35-D (1.0 eq), iodomethane-d3 (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 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 35-E (yield: 75%).

[0587] Synthesis of intermediate compound 35-F

[0588] Intermediate compound 35-E (1.2 eq), 2-(3-bromophenoxy)-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 water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated, and intermediate compound 35-F (yield: 77%) was obtained by column chromatography (ethyl acetate:hexane = 1:9).

[0589] Synthesis of intermediate compound 35-G

[0590] Intermediate compound 35-F (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. After cooling to room temperature, the triethyl orthoformate was concentrated (e.g., a triethyl orthoformate solution) and 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 intermediate compound 35-G (yield: 37%) was obtained by column chromatography (MC, MC: 5 vol% methanol).

[0591] Synthesis of intermediate compound 35-H

[0592] Intermediate compound 35-G (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 to 12 hours. After washing with distilled water and filtering to obtain a solid, it was extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated to synthesize intermediate compound 35-H (yield 94%).

[0593] Synthesis of Compound 35

[0594] Intermediate compound 35-H (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 then stirred at 120 °C under nitrogen conditions (e.g., under a nitrogen inert atmosphere) for 4 days. The reaction mixture was cooled to room temperature and then extracted three times with water to obtain an organic layer. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated, and compound 35 was obtained by column chromatography (MC: 50 v / v hexane) (yield: 23%).

[0595] Evaluation Example 1

[0596] Quantum simulations were used to evaluate each compound from Synthetic Examples 1 to 9 and Comparative Example 1. 3 MLCT (%), Simulated Maximum Emission Wavelength (λ) max sim )and 3 MC energy levels. The actual maximum emission wavelength (λ) for each compound was also measured. max exp The results are shown in Table 1.

[0597] In more detail, the properties of compounds 5 and 7, as well as compound A as a comparative compound, were evaluated, and the B3LYP functional method was used to evaluate the properties of each compound. 3 Energy level values ​​of the MC state. Calculations were performed using density functional theory (DFT) with a Gaussian procedure at the B3LYP, 6-31G(d,p) level, with structural optimization measurements. 3 MLCT (%) value.

[0598] Table 1

[0599]

[0600]

[0601]

[0602] Table 1 shows that compounds 1, 2, 4, 5, 7, 8, 12, 23, and 35... 3 The MC values ​​were all significantly higher than those of compound A. 3 MC value. Therefore, each of compounds 1, 2, 4, 5, 7, 8, 12, 23, and 35 is derived from... 3 MCLT state transition to non-emission state (i.e. 3 The probability of the MC state can be low. Therefore, the stability of each of compounds 1, 2, 4, 5, 7, 8, 12, 23 and 35 in the excited state can be suitable (e.g., excellent) and can improve the efficiency and lifetime of organic light-emitting devices including organometallic compounds.

[0603] Example

[0604] Example 1

[0605] The substrate and anode will have a strength of 15Ω / cm. 2 The ITO glass substrate (manufactured by Corning) was cut to a size of 50mm × 50mm × 0.7mm and then ultrasonicated with isopropanol and pure water for 5 minutes each. It was then irradiated with ultraviolet (UV) light for 30 minutes and exposed to ozone for cleaning. The resulting glass substrate was then loaded onto a vacuum deposition apparatus.

[0606] 2-TNATA was vacuum deposited onto an ITO anode on a glass substrate to form a structure with... A hole injection layer of a certain thickness is formed, and then NPB is vacuum deposited on the hole injection layer to form a layer with... A hole transport layer of a certain thickness.

[0607] The co-host material bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS) and (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenylphosphine oxide (POPCPA) (BCPDS to POPCPA weight ratio 1:1) and compound 1 as a dopant were co-deposited on the hole transport layer at a co-host to dopant weight ratio of 90:10 to form a structure with... The thickness of the emission layer.

[0608] Diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1) was deposited on the emitter layer to form a structure with... A hole-blocking layer of a certain thickness is formed, and Alq3 is deposited on the hole-blocking layer to form a hole-blocking layer with a certain thickness. A thick electron transport layer is formed by depositing LiF on the electron transport layer to create an electron transport layer with [missing information]. An electron-injected layer of a certain thickness is formed, and Al is vacuum-deposited onto 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.

[0609]

[0610] Examples 2 through 9 and comparison example 1

[0611] The organic light-emitting device is fabricated in the same manner as in Example 1, except that the corresponding compound shown in Table 1 is used instead of compound 1 as a dopant when forming the emission layer.

[0612] Evaluation Example 2

[0613] The driving voltage, current density, luminance, luminous efficiency, emission color, and maximum emission wavelength of each organic light-emitting device manufactured according to Examples 1 to 9 and Comparative Example 1 were measured using a Keithley SMU 236 and a PR650 luminance photometer. The results are shown in Table 2.

[0614] Table 2

[0615]

[0616]

[0617] Referring to Table 2, it is confirmed that each of the organic light-emitting devices in Examples 1 to 9 has a higher brightness level and higher luminous efficiency compared to the organic light-emitting device in Comparative Example 1.

[0618] According to one or more embodiments, organic light-emitting devices comprising organometallic compounds can have high brightness, high efficiency, and long lifespan.

[0619] When describing embodiments of the invention, the use of "may" refers to "one or more embodiments of the invention." Furthermore, the term "exemplary" is intended to indicate an example or illustration.

[0620] As used herein, the terms “substantially,” “approximately,” 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 stated herein is intended to include all subranges of the same numerical precision contained within the stated range. For example, the range “1.0 to 10.0” is intended to include all subranges between the stated minimum value of 1.0 and the stated maximum value of 10.0 (and includes both the stated minimum value of 1.0 and the stated maximum value of 10.0), i.e., 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 stated herein is intended to include all smaller numerical limits contained therein, and any minimum numerical limit stated in this specification is intended to include all larger 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 range expressly stated herein. This specification is intended to inherently describe all such scopes, such that modifications to explicitly state any such subscope would be appropriate.

[0621] 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 suitable 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; as well as An organic layer, including an emission layer, is located between the first electrode and the second electrode. The organic light-emitting device includes at least one organometallic compound represented by Formula 1: Formula 1 In Equation 1, M1 is selected from platinum, palladium, copper, silver, gold, rhodium, iridium, ruthenium, osmium, titanium, zirconium, hafnium, europium, terbium, and thulium. Y1 to Y3 are each independently N or C. T1 through 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"), or C (=O). When T1 is a chemical bond, Y1 and M1 are directly bonded to each other; when T2 is a chemical bond, Y2 and M1 are directly bonded to each other; when T3 is a chemical bond, Y3 and M1 are directly bonded to each other; and when T4 is a chemical bond, A4 and M1 are directly bonded to each other. Two of the following bonds are selected from the bonds between M1 and Y1 or T1, M1 and Y2 or T2, M1 and Y3 or T3, and M1 and A4 or T4: both must be coordinate bonds, and the other two bonds must be covalent bonds. A1 to A3 are all independently selected from C5-C 60 Carbocyclic groups and C1-C 60 Heterocyclic group, 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-*'. a1 through 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. L 11 and L 12 All are independently selected from *-C(R) 11 (R) 12 )-*'、*-C(R 11 )=*'、*=C(R 11 )-*' and *-C(R 11 )=C(R 12 )-*', a11 and a12 are both independent integers from 1 to 3. R', R", R1 to R6 and 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), b1 to b3 are all independent integers from 0 to 20. b4 is an integer from 0 to 6. R', R", R1 of b1 numbers, R2 of b2 numbers, R3 of b3 numbers, R4 of b4 numbers, R5, R6, R 11 and R 12 Adjacent groups in the C5-C may optionally connect to each other to form substituted or unsubstituted C5-C. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group, Both * and *' represent bonding sites with adjacent atoms, and The substituted C5-C 60 Carbocyclic group, the substituted C1-C 60 Heterocyclic groups, the substituted C1-C 60 Alkyl groups, the substituted C2-C 60 alkenyl, the substituted C2-C 60 alkynyl group, the substituted C1-C 60 Alkoxy groups, the substituted C3-C 10 cycloalkyl, the substituted C1-C 10 Heterocyclic alkyl groups, the substituted C3-C 10 cycloalkenyl, the substituted C1-C 10 Heterocyclic alkenyl groups, the substituted C6-C 60 Aryl, the substituted C6-C 60 aryloxy groups, the substituted C6-C 60 Arylthioyl, the substituted C1-C 60 heteroaryl, the substituted C1-C 60 Heteroaryl groups, the substituted C1-C 60 At least one substituent selected from the following: heteroarylsulfonyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heterocyclic group. 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; 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; 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; 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 Alkyne 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 -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 ), and 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 Alkyne 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, -Cl, -Br, -I and cyano. 60 Alkyl groups, substituted with at least one of deuterium, -F, -Cl, -Br, -I, and cyano groups, are C6-C. 60 Aryl, biphenyl, and terphenyl The prerequisite is that M1 is platinum, a4 is 0, and L... 11 and L 12 Each is independently *-C(R) 11 (R) 12 )-*'hour: b4 is 1 to 6; and The N-substitution connected to L4 is: C1-C substituted with at least one deuterium. 20 Alkyl groups, or C6-C groups substituted with at least one deuterium 20 The aryl group or the substituted C6-C group is substituted with at least one deuterium. 20 C6-C of aryl 20 Aryl.

2. The organic light-emitting device according to claim 1, wherein, The organometallic compound 3 Energy level E of MC state 3MC It is 0.41 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. The organic light-emitting device according to claim 3, wherein, The emission layer also includes a body, and based on 100 parts by weight of the emission layer, the amount of the at least one organometallic compound is from 0.1 parts by weight to 50 parts by weight.

5. The organic light-emitting device according to claim 3, wherein, The emission layer emits blue light with a maximum emission wavelength of 440nm to 490nm.

6. The organic light-emitting device according to claim 1, wherein, The first electrode is the anode. The second electrode is the cathode. The organic layer includes at least one organometallic compound. The organic layer further includes 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. The hole transport region includes a hole injection layer, a hole transport layer, an emission assist layer, and / or an electron blocking layer, and The electron transport region includes a buffer layer, a hole blocking layer, an electron transport layer, and / or an electron injection layer.

7. An organometallic compound, said organometallic compound being represented by Formula 1: Formula 1 in, In Equation 1, M1 is selected from platinum, palladium, copper, silver, gold, rhodium, iridium, ruthenium, osmium, titanium, zirconium, hafnium, europium, terbium, and thulium. Y1 to Y3 are each independently N or C. T1 through 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"), or C (=O). When T1 is a chemical bond, Y1 and M1 are directly bonded to each other; when T2 is a chemical bond, Y2 and M1 are directly bonded to each other; when T3 is a chemical bond, Y3 and M1 are directly bonded to each other; and when T4 is a chemical bond, A4 and M1 are directly bonded to each other. Two of the following bonds are selected from the bonds between M1 and Y1 or T1, M1 and Y2 or T2, M1 and Y3 or T3, and M1 and T4 or C: both must be coordinate bonds, and the other two bonds must be covalent bonds. A1 to A3 are all independently selected from C5-C 60 Carbocyclic groups and C1-C 60 Heterocyclic group, 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-*'. a1 through 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. L 11 and L 12 All are independently selected from *-C(R) 11 (R) 12 )-*'、*-C(R 11 )=*'、*=C(R 11 )-*' and *-C(R 11 )=C(R 12 )-*', a11 and a12 are both independent integers from 1 to 3. R', R", R1 to R6 and 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), b1 to b3 are all independent integers from 0 to 20. b4 is an integer from 0 to 6. R', R", R1 of b1 numbers, R2 of b2 numbers, R3 of b3 numbers, R4 of b4 numbers, R5, R6, R 11 and R 12 Adjacent groups in the C5-C may optionally connect to each other to form substituted or unsubstituted C5-C. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group, Both * and *' indicate bonding sites with adjacent atoms. The substituted C5-C 60 Carbocyclic group, the substituted C1-C 60 Heterocyclic groups, the substituted C1-C 60 Alkyl groups, the substituted C2-C 60 alkenyl, the substituted C2-C 60 alkynyl group, the substituted C1-C 60 Alkoxy groups, the substituted C3-C 10 cycloalkyl, the substituted C1-C 10 Heterocyclic alkyl groups, the substituted C3-C 10 cycloalkenyl, the substituted C1-C 10 Heterocyclic alkenyl groups, the substituted C6-C 60 Aryl, the substituted C6-C 60 aryloxy groups, the substituted C6-C 60 Arylthioyl, the substituted C1-C 60 heteroaryl, the substituted C1-C 60 Heteroaryl groups, the substituted C1-C 60 At least one substituent selected from the following: heteroarylsulfonyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heterocyclic group. 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; 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; 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; 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 Alkyne 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 -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 ), and 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 Alkyne 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, -Cl, -Br, -I and cyano. 60 Alkyl groups, substituted with at least one of deuterium, -F, -Cl, -Br, -I, and cyano groups, are C6-C. 60 Aryl, biphenyl, and terphenyl The prerequisite is that M1 is platinum, a4 is 0, and L... 11 and L 12 Each is independently *-C(R) 11 (R) 12 )-*'hour: b4 is 1 to 6; and The N-substitution connected to L4 is: C1-C substituted with at least one deuterium. 20 Alkyl groups, or C6-C groups substituted with at least one deuterium 20 The aryl group or the substituted C6-C group is substituted with at least one deuterium. 20 C6-C of aryl 20 Aryl.

8. The organometallic compound according to claim 7, wherein, A1 to A3 are all independently selected from: 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.

9. The organometallic compound according to claim 7, wherein, i)L 11 and L 12 All are *-C(R) 11 (R) 12 )-*', a11 is 2, and a12 is 1. ii)L 11 For *-C(R) 11 )=C(R 12 )-*',L 12 For *-C(R) 11 (R) 12 )-*', and both a11 and a12 are 1, or iii)L 11 For *-C(R) 11 (R) 12 )-*',L 12 For *-C(R) 11 )=C(R 12 )-*', and both a11 and a12 are 1.

10. The organometallic compound according to claim 7, wherein, The organometallic compound is represented by one of formulas 1-1 to 1-6: Among them, in equations 1-1 to 1-6, M1, A1 to A3, Y1 to Y3, L1 to L3, a1 to a3, R1 to R3, and b1 to b3 are all independently identical to those described in combination formula 1. A 21 The same as that described by A1 in Formula 1, R a To R k and R 21 Each of them is independently identical to R1 described in Associative Formula 1. b21 is the same as b1 in combination 1, and In Equation 1-1, the prerequisite is that when M1 is platinum, R a To replace C1-C with at least one deuterium 20 Alkyl groups, or C6-C groups substituted with at least one deuterium 20 The aryl group or the substituted C6-C group is substituted with at least one deuterium. 20 C6-C of aryl 20 Aryl.

11. The organometallic compound according to claim 7, wherein, The organometallic compound is selected from compounds 1 to 44:

Images