Light-emitting element and electronic device including same
By integrating π-electron deficient nitrogen-containing cyclic groups into the intermediate layer, the light-emitting device achieves enhanced luminous efficiency and longevity, addressing the limitations of existing elements.
Patent Information
- Application Number
- JP2021115852
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2020-07-13
- Filing Date
- 2021-07-13
- Publication Date
- 2026-01-09
- Estimated Expiration
- 2041-07-13
AI Technical Summary
Existing light-emitting elements face challenges in achieving high luminous efficiency and long lifespan.
Incorporating specific compounds represented by chemical formulas 1 and 3, which are π-electron deficient nitrogen-containing C1-C60 cyclic groups, into the intermediate layer of a light-emitting device to enhance luminous efficiency and longevity.
The light-emitting device exhibits improved driving voltage, current density, and luminous efficiency, making it suitable for high-quality electronic devices.
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Abstract
Description
[Technical Field]
[0001] The present invention relates to a light-emitting element and an electronic device including the same. [Background technology]
[0002] Among light-emitting elements, self-luminous elements not only have a wide viewing angle and excellent contrast, but also have a short response time and are excellent in brightness, driving voltage and response speed.
[0003] A light-emitting device may have a structure in which a first electrode is disposed on a substrate, and a hole transport region, a light-emitting layer, an electron transport region, and a second electrode are sequentially disposed on the first electrode. Holes injected from the first electrode travel to the light-emitting layer via the hole transport region, and electrons injected from the second electrode travel to the light-emitting layer via the electron transport region. Carriers such as holes and electrons recombine in the light-emitting layer region to generate excitons. Light is generated as the excitons change from their excited state to their ground state. [Prior art documents] [Patent documents]
[0004] [Patent Document 1] Japanese Patent Application Laid-Open No. 2007-045742 Summary of the Invention [Problem to be solved by the invention]
[0005] The problem to be solved by the present invention is to provide a light emitting element having high luminous efficiency and long life, and an electronic device including the same. [Means for solving the problem]
[0006] According to one embodiment of the present disclosure, A first electrode; a second electrode facing the first electrode; an intermediate layer disposed between the first electrode and the second electrode and including a light-emitting layer; The intermediate layer is i) a first compound represented by the following chemical formula 1; ii) at least one π-electron deficient nitrogen-containing C1-C 60 Cyclic group (πelectron-deficient nitrogen-containing C1-C 60 a second compound having a group represented by the following chemical formula 3; a fourth compound capable of emitting delayed fluorescence; or any combination thereof; A light-emitting device is provided in which the first compound, the second compound, the third compound, and the fourth compound are different from each other. [ka] ...(chemical formula 1) [ka] ...(chemical formula 3) (In the above Chemical Formula 1, M is platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu), In the above Chemical Formula 1, X1 to X4 are each independently C or N, In the formula 1, i) the bond between X1 and M is a coordinate bond, ii) one of the bonds between X2 and M, the bond between X3 and M, and the bond between X4 and M is a coordinate bond, and the remaining two are covalent bonds; In the above Chemical Formula 1, the ring CY1 is a group having a ring structure selected from i) an X1-containing five-membered ring, ii) an X1-containing five-membered ring to which at least one six-membered ring is fused, and iii) an X1-containing six-membered ring; In the above formula 1, the ring CY2 is C3-C 60 Carbocyclic group or C1-C 60 is a heterocyclic group, In the above Chemical Formula 1, X 31 ~X36 , and X 41 ~X 44 are, independently of each other, C or N, In the above Chemical Formula 1, X 51 are *-N(R5)-*', *-B(R5)-*', *-P(R5)-*', *-C(R 5a )(R 5b )-*', *-Si(R 5a )(R 5b )-*', *-Ge(R 5a )(R 5b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R5)=*', *=C(R5)-*', *-C(R 5a )=C(R 5b )-*', *-C(=S)-*' or *-C≡C-*', wherein the * and the *' are bonding positions to adjacent atoms, In the above Chemical Formula 1, L1 is a single bond, at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 is a heterocyclic group, In the above Chemical Formula 1, b1 is an integer of 1 to 5; In the above formula 1, R1 to R5, R 5a and R 5b are each independently a group represented by the following chemical formula 1-1, a group represented by the following chemical formula 1-2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, at least one R 10a Substituted or unsubstituted C1-C 60 alkyl group, at least one R 10a Substituted or unsubstituted C2-C 60 alkenyl group, at least one R 10a Substituted or unsubstituted C2-C 60 an alkynyl group, at least one R 10a Substituted or unsubstituted C1-C 60 an alkoxy group, at least one R10a Substituted or unsubstituted C3-C 60 Carbocyclic group, at least one R 10a Substituted or unsubstituted C1-C 60 Heterocyclic group, at least one R 10a Substituted or unsubstituted C6-C 60 an aryloxy group, at least one R 10a Substituted or unsubstituted C6-C 60 an arylthio group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2); [ka] ...(chemical formula 1-1) [ka] ...(Chemical formula 1-2) In the above Chemical Formula 1, c1 is an integer of 0 to 5, a1 and a4 are each independently an integer of 0 to 4, a2 is an integer of 0 to 10, a3 is an integer of 0 to 6, the sum of a1 to a4 is 1 or more, and a1 *-(L1) b1 -(R1) c1 at least one of the groups represented by the formula (I-1), at least one of the a2 R2s, at least one of the a3 R3s, at least one of the a4 R4s, or any combination thereof, are each independently a group represented by the formula (I-1) or a group represented by the formula (I-2), In the chemical formula 1-1 and the chemical formula 1-2, L7 is a single bond, at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 is a heterocyclic group, In the chemical formula 1-1 and the chemical formula 1-2, b7 is an integer of 1 to 5, In the chemical formula 1-1 and the chemical formula 1-2, the ring CY7 is C3-C 60 Carbocyclic group or C1-C 60 is a heterocyclic group, In the chemical formula 1-1 and the chemical formula 1-2, n7 is an integer of 1 to 5, In the above formula 1-1, the ring CY8 is a non-aromatic C3-C 60 Carbocyclic or non-aromatic C1-C 60 is a heterocyclic group, In the chemical formula 1-1 and the chemical formula 1-2, R7 to R9 are each independently a group represented by the chemical formula 1-1, a group represented by the chemical formula 1-2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, or at least one R 10a Substituted or unsubstituted C1-C 60 alkyl group, at least one R 10a Substituted or unsubstituted C2-C 60 alkenyl group, at least one R 10a Substituted or unsubstituted C2-C 60 an alkynyl group, at least one R 10a Substituted or unsubstituted C1-C 60 an alkoxy group, at least one R 10a Substituted or unsubstituted C3-C 60 Carbocyclic group, at least one R 10a Substituted or unsubstituted C1-C 60 Heterocyclic group, at least one R 10a Substituted or unsubstituted C6-C 60 an aryloxy group, at least one R 10a Substituted or unsubstituted C6-C 60 an arylthio group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2); In the formula 1-1 and the formula 1-2, a7 and a8 each independently represent an integer of 0 to 20; In the above-mentioned Chemical Formula 3, the ring CY 71and KanCY 72 are independently of each other, π-electron-rich C3-C 60 Cyclic group (πelectron-rich C3-C 60 cyclic group) or pyridinyl group, In Chemical Formula 3, X 71 is a single bond or a linking group containing O, S, N, B, C, Si, or any combination thereof; In the chemical formula 3, * represents the bonding position of the compound 3 to the adjacent atom, a1 *-(L1) b1 -(R1) c1 Two or more of the groups represented by the formula (I) are optionally bonded to each other, and at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 can form a heterocyclic group, Two or more of the a2 R2 may be optionally bonded to each other, and at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 can form a heterocyclic group, Two or more of the a3 R3 may be optionally bonded to each other, and at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 can form a heterocyclic group, Two or more of the a4 R4 may be optionally bonded to each other, and at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 can form a heterocyclic group, The aforementioned R1 to R5, R 5a and R5b two or more of the R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 can form a heterocyclic group, R 10a teeth, deuterium (-D), -F, -Cl, -Br, -I, hydroxyl, cyano, or nitro groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3-C 60 carbocyclic group, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ), -P(=O)(Q 11 )(Q 12 ), or any combination thereof, substituted or unsubstituted, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group or C1-C 60 alkoxy groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy groups, C3-C 60 carbocyclic group, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, -Si(Q 21 )(Q 22 )(Q23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ), -P(=O)(Q 21 )(Q 22 ), or any combination thereof, substituted or unsubstituted, C3-C 60 carbocyclic group, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group or C6-C 60 an arylthio group; or -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ); and yes The aforementioned Q1 to Q3, Q 11 ~Q 13 , Q 21 ~Q 23 , and Q 31 ~Q 33 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy group, or deuterium, -F, cyano group, C1-C 60 Alkyl groups, C1-C 60 C3-C substituted or unsubstituted with alkoxy, phenyl, biphenylyl, or any combination thereof 60 Carbocyclic group or C1-C 60 a heterocyclic group; The third compound is not CBP (4,4'-bis(9H-carbazol-9-yl)biphenyl) or mCBP (3,3'-di(9H-carbazol-9-yl)-1,1'-biphenyl) shown below. [ka]
[0007] According to another embodiment, an electronic device is provided that includes the light-emitting element.
[0008] According to yet another embodiment, there is provided an organometallic compound represented by Chemical Formula 1. [Effects of the Invention]
[0009] The light-emitting device of the present invention has excellent driving voltage and current density, as well as high luminous efficiency and long life, and is suitable for use in high-quality electronic devices. [Brief explanation of the drawings]
[0010] [Figure 1] 1 is a diagram schematically illustrating a structure of a light emitting device according to an embodiment. [Figure 2] 1 is a diagram illustrating a schematic structure of an electronic device according to an embodiment; [Figure 3] 10 is a diagram illustrating a schematic structure of an electronic device according to another embodiment. [Figure 4] 1 is a diagram showing electroluminescence (EL) spectra of the organic light-emitting devices of Examples 1 to 6, Example 11, and Comparative Example 1. [Figure 5] 1 is a diagram showing electroluminescence spectra of organic light-emitting devices according to Examples 1, 7, and 8. [Figure 6] 1 is a graph showing luminance vs. luminous efficiency of organic light-emitting devices according to Examples 1 to 8, Example 11, and Comparative Example 1. [Figure 7] 1 is a graph showing time-brightness graphs for the organic light-emitting devices of Examples 1 to 8, Example 11, and Comparative Example 1. DETAILED DESCRIPTION OF THE INVENTION
[0011] [Term definition] As used herein, C3-C 60 A carbocyclic group is a C3-C ring structure consisting of only carbon atoms. 60 means a cyclic group, C1-C 60 Heterocyclic groups are C1-C groups that contain, in addition to carbon, further heteroatoms. 60 means a cyclic group. C3-C 60 Carbocyclic groups and 1-C 60 Each heterocyclic group may be a monocyclic group consisting of one ring, or a polycyclic group in which two or more rings are fused together. For example, C1-C 60 The heterocyclic group has 3 to 61 ring atoms.
[0012] As used herein, a cyclic group is defined as a C-C 60 Carbocyclic groups and C1-C 60 Heterocyclic groups are also included.
[0013] In this specification, π-electron-rich C3-C 60 Cyclic group (π electron-rich C3-C 60 A ring-forming moiety is a C3-C cyclic group that does not contain *-N=*'. 60 Cyclic group, π-electron deficient nitrogen-containing C1-C 60 Cyclic group (π electron-deficient nitrogen-containing C1-C 60 cyclic group) is a ring-forming moiety, C1-C including *-N=*' 60 It means a heterocyclic group.
[0014] for example, C3-C 60The carbocyclic group may be i) a group T1, or ii) a fused ring group in which two or more groups T1 are fused to each other (e.g., a group having a ring structure selected from cyclopentadiene, adamantane, norbornane, benzene, pentalene, naphthalene, azulene, indacene, acenaphthylene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, perylene, pentaphene, heptalene, naphthacene, picene, hexacene, pentacene, rubicene, coronene, ovalene, indene, fluorene, spiro-bifluorene, benzofluorene, indenophenanthrene, and indenoanthracene, etc.), C1-C 60The heterocyclic group is i) a group T2, ii) a fused ring group in which two or more groups T2 are fused to each other, or iii) a fused ring group in which one or more groups T2 and one or more groups T1 are fused to each other (for example, pyrrole, thiophene, furan, indole, benzoindole, naphthoindole, isoindole, benzisoindole, naphthoisoindole, benzosilole, benzothiophene, benzofuran, carbazole, dibenzosilole, dibenzothiophene, dibenzofuran, indenocarbazole, indolocarbazole, benzofurocarbazole, benzothienocarbazole, benzosilolocarbazole, benzoindolocarbazole, benzocarbazole, benzonaphthofuran, benzonaphthothiophene, benzonaphthosilole, benzofurodibenzofuran, benzofurodibenzothiophene, benzothienodibenzo a group having a ring structure selected from thiophene, pyrazole, imidazole, triazole, oxazole, isoxazole, oxadiazole, thiazole, isothiazole, thiadiazole, benzopyrazole, benzimidazole, benzoxazole, benzisoxazole, benzothiazole, benzisothiazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, benzoquinoline, benzisoquinoline, quinoxaline, benzoquinoxaline, quinazoline, benzoquinazoline, phenanthroline, cinnoline, phthalazine, naphthyridine, imidazopyridine, imidazopyrimidine, imidazotriazine, imidazopyrazine, imidazopyridazine, azacarbazole, azafluorene, azadibenzosilole, azadibenzothiophene, azadibenzofuran, etc.), π-electron-rich C3-C 60 The cyclic group is i) a group T1, ii) a fused ring group in which two or more groups T1 are fused to each other, iii) a group T3, iv) a fused ring group in which two or more groups T3 are fused to each other, or v) a fused ring group in which one or more groups T3 and one or more groups T1 are fused to each other (e.g., C3-C 60a group having a ring structure selected from a carbocycle, pyrrole, thiophene, furan, indole, benzoindole, naphthoindole, isoindole, benzisoindole, naphthoisoindole, benzosilole, benzothiophene, benzofuran, carbazole, dibenzosilole, dibenzothiophene, dibenzofuran, indenocarbazole, indolocarbazole, benzofurocarbazole, benzothienocarbazole, benzosilolocarbazole, benzoindolocarbazole, benzocarbazole, benzonaphthofuran, benzonaphthothiophene, benzonaphthosilole, benzofurodibenzofuran, benzofurodibenzothiophene, benzothienodibenzothiophene, etc.), π-electron deficient nitrogen-containing C1-C 60 The cyclic group is i) a group T4, ii) a fused ring group in which two or more groups T4 are fused to each other, iii) a fused ring group in which one or more groups T4 and one or more groups T1 are fused to each other, iv) a fused ring group in which one or more groups T4 and one or more groups T3 are fused to each other, or v) a fused ring group in which one or more groups T4, one or more groups T1, and one or more groups T3 are fused to each other (e.g., pyrazole, imidazole, triazole, oxazole, isoxazole, oxadiazole, thiazole, isothiazole, thiadiazole, benzopyrazole, benzimidazole, benzoxazole, a group having a ring structure selected from the group consisting of benzophenone, benzisoxazole, benzothiazole, benzisothiazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, benzoquinoline, benzisoquinoline, quinoxaline, benzoquinoxaline, quinazoline, benzoquinazoline, phenanthroline, cinnoline, phthalazine, naphthyridine, imidazopyridine, imidazopyrimidine, imidazotriazine, imidazopyrazine, imidazopyridazine, azacarbazole, azafluorene, azadibenzosilole, azadibenzothiophene, azadibenzofuran, and the like), Group T1 is a group having a ring structure selected from cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutene, cyclopentene, cyclopentadiene, cyclohexene, cyclohexadiene, cycloheptene, adamantane, norbornane (or bicyclo[2.2.1]heptane), norbornene, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane, and benzene; Group T2 is a group having a ring structure selected from furan, thiophene, 1H-pyrrole, silole, borole, 2H-pyrrole, 3H-pyrrole, imidazole, pyrazole, triazole, tetrazole, oxazole, isoxazole, oxadiazole, thiazole, isothiazole, thiadiazole, azasilole, azaborole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, and tetrazine; Group T3 is a group having a ring structure selected from furan, thiophene, 1H-pyrrole, silole, and borole; Group T4 may be a group having a ring structure selected from 2H-pyrrole, 3H-pyrrole, imidazole, pyrazole, triazole, tetrazole, oxazole, isoxazole, oxadiazole, thiazole, isothiazole, thiadiazole, azasilole, azaborole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, and tetrazine.
[0015] As used herein, cyclic groups, C3-C 60 carbocyclic group, C1-C 60 Heterocyclic groups, π-electron-rich C3-C 60 Cyclic group or π-electron deficient nitrogen-containing C1-C 60The term "cyclic group" refers to a group, monovalent group, or polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) fused to any cyclic group, depending on the structure of the chemical formula in which the term is used. For example, a "group having a benzene ring structure" may be a benzo group, a phenyl group, a phenylene group, etc., which can be easily understood by a person skilled in the art based on the structure of the chemical formula containing the "group having a benzene ring structure."
[0016] For example, monovalent C3-C 60 Carbocyclic groups and monovalent C-C 60 Examples of heterocyclic groups are C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C1-C 60 Divalent C3-C, including heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups 60 Carbocyclic groups and divalent C1-C 60 Examples of heterocyclic groups are C3-C 10 Cycloalkylene groups, C1-C 10 Heterocycloalkylene groups, C3-C 10 Cycloalkenylene group, C1-C 10 Heterocycloalkenylene group, C6-C 60 Arylene groups, C1-C 60 It may include heteroarylene groups, divalent non-aromatic fused polycyclic groups, and divalent non-aromatic hetero-fused polycyclic groups.
[0017] As used herein, C1-C 60 Alkyl groups are C1-C 60 Linear or C1-C 60It means a branched aliphatic hydrocarbon monovalent group, and specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, and the like. 60 The alkylene group is C1-C 60 It means a divalent group having the same structure as an alkyl group.
[0018] As used herein, C2-C 60 Alkenyl groups are C2-C 60 It means a monovalent hydrocarbon group containing one or more carbon-carbon double bonds in the middle or at the end of the alkyl group, and specific examples thereof include ethenyl, propenyl, and butenyl groups. 60 The alkenylene group is C2-C 60 It means a divalent group having the same structure as an alkenyl group.
[0019] As used herein, C2-C 60 Alkynyl groups are C2-C 60 It means a monovalent hydrocarbon group containing one or more carbon-carbon triple bonds in the middle or at the end of the alkyl group, and specific examples thereof include an ethynyl group and a propynyl group. 60 The alkynylene group is C2-C 60 It means a divalent group having the same structure as an alkynyl group.
[0020] As used herein, C1-C 60 The alkoxy group is -OA. 101 (where A 101is C1-C 60 Specific examples include a methoxy group, an ethoxy group, an isopropyloxy group, and the like.
[0021] As used herein, C3-C 10 Cycloalkyl groups are C3-C 10 It means a monovalent saturated hydrocarbon cyclic group, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, and the like. 10 The cycloalkylene group is C3-C 10 It means a divalent group having the same structure as a cycloalkyl group.
[0022] As used herein, C1-C 10 Heterocycloalkyl groups are C1-C12 alkyl groups which, in addition to carbon atoms, further contain at least one heteroatom as a ring-forming atom. 10 It means a monovalent cyclic group, and specific examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, etc. 10 The heterocycloalkylene group is C1-C 10 It means a divalent group having the same structure as a heterocycloalkyl group.
[0023] As used herein, C3-C 10 The cycloalkenyl group is C3-C 10 It means a monovalent cyclic group that has at least one carbon-carbon double bond in the ring but does not have aromaticity, and specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. 10 The cycloalkenylene group is C3-C 10It means a divalent group having the same structure as a cycloalkenyl group.
[0024] As used herein, C1-C 10 A heterocycloalkenyl group is a C1-C12 alkyl group that contains, in addition to carbon atoms, at least one heteroatom as a ring-forming atom. 10 It is a monovalent cyclic group having at least one double bond in the ring. 10 Specific examples of heterocycloalkenyl groups include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like. 10 The heterocycloalkenylene group is a C1-C 10 It means a divalent group having the same structure as a heterocycloalkenyl group.
[0025] As used herein, C6-C 60 The aryl group is C6-C 60 means a monovalent group having an aromatic carbocyclic ring, C6-C 60 The arylene group is C6-C 60 means a divalent group having an aromatic carbocyclic ring. C6-C 60 Specific examples of the aryl group include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, and the like. 60 Aryl groups and C6-C 60 When the arylene group contains more than one ring, the two or more rings may be fused together.
[0026] As used herein, C1-C 60 A heteroaryl group further contains at least one heteroatom as a ring-forming atom in addition to carbon atoms, and is C-C 60 means a monovalent group having an aromatic heterocycle, C1-C 60The heteroarylene group further contains at least one heteroatom as a ring-forming atom in addition to carbon atoms, and is C-C 60 It means a divalent group having an aromatic heterocycle. C1-C 60 Specific examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, and the like. 60 Heteroaryl groups and C1-C 60 When a heteroarylene group contains more than one ring, the two or more rings may be fused together.
[0027] As used herein, a monovalent non-aromatic fused polycyclic group refers to a monovalent group (e.g., having 8 to 60 ring carbon atoms) in which two or more rings are fused together, the ring atoms are carbon, and the entire molecule is non-aromatic. Specific examples of monovalent non-aromatic fused polycyclic groups include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, and an indenoanthracenyl group. As used herein, a divalent non-aromatic fused polycyclic group refers to a divalent group having the same structure as a monovalent non-aromatic fused polycyclic group.
[0028] In this specification, a monovalent non-aromatic hetero-fused polycyclic group refers to a monovalent group in which two or more rings are fused together, which further contains at least one heteroatom as a ring-forming atom in addition to carbon atoms, and which has non-aromatic properties as a whole molecule (e.g., having 1 to 60 ring-forming carbon atoms). Specific examples of the monovalent non-aromatic hetero-condensed polycyclic group include a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphthoindolyl group, an isoindolyl group, a benzisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, and a thiadiazolyl group. , benzopyrazolyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, benzoxadiazolyl group, benzothiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, imidazotriazinyl group, imidazopyrazinyl group, imidazopyridazinyl group, indenocarbazolyl group, indolocarbazolyl group, benzofurocarbazolyl group, benzothienocarbazolyl group, benzosilolocarbazolyl group, benzoindolocarbazolyl group, benzocarbazolyl group, benzonaphthofuranyl group, benzonaphthothiophenyl group, benzonaphthosilolyl group, benzofurodibenzofuranyl group, benzofurodibenzothiophenyl group, benzothienodibenzothiophenyl group, etc. In this specification, a divalent non-aromatic hetero-condensed polycyclic group means a divalent group having the same structure as a monovalent non-aromatic hetero-condensed polycyclic group.
[0029] As used herein, C6-C 60 The aryloxy group is -OA. 102 (where A 102 is C6-C 60 A monovalent group represented by the formula C6-C 60 The arylthio group is -SA 103(where A 103 is C6-C 60 aryl group).
[0030] As used herein, "R 10a "teeth, deuterium (-D), -F, -Cl, -Br, -I, hydroxyl, cyano, or nitro groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3-C 60 carbocyclic group, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ), -P(=O)(Q 11 )(Q 12 ), or any combination thereof, substituted or unsubstituted, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group or C1-C 60 alkoxy groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy groups, C3-C 60 carbocyclic group, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ), -P(=O)(Q 21 )(Q 22 ), or any combination thereof, substituted or unsubstituted, C3-C 60 carbocyclic group, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group or C6-C 60 an arylthio group; or -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ); may also be used.
[0031] In this specification, Q1 to Q3, Q 11 ~Q 13 , Q 21 ~Q 23 , and Q 31 ~Q 33 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy group, or deuterium, -F, cyano group, C1-C 60 Alkyl groups, C1-C 60 C3-C substituted or unsubstituted with alkoxy, phenyl, biphenylyl, or any combination thereof 60 Carbocyclic group or C1-C 60 It may also be a heterocyclic group.
[0032] As used herein, heteroatom refers to any atom other than a carbon atom. Examples of heteroatoms include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
[0033] As used herein, "Ph" means a phenyl group, "Me" means a methyl group, "Et" means an ethyl group, "ter-Bu" or "But" means a tert-butyl group, and "OMe" means a methoxy group.
[0034] In this specification, the term "biphenylyl group" means a "phenyl group substituted with a phenyl group." The term "biphenylyl group" refers to a group in which the substituent is "C6-C 60 It belongs to the "substituted phenyl group" which is an "aryl group."
[0035] In this specification, the term "terphenylyl group" means a "phenyl group substituted with a biphenylyl group." The term "terphenylyl group" refers to a group in which the substituent is "C6-C 60 C6-C substituted with aryl groups 60 It belongs to the "substituted phenyl group" which is an "aryl group."
[0036] In this specification, unless otherwise defined, * and *' refer to the bonding positions to adjacent atoms in the chemical formula.
[0037] [Light-emitting element] The light-emitting device of the present invention includes a first electrode, a second electrode facing the first electrode, and an intermediate layer disposed between the first electrode and the second electrode and including a light-emitting layer. i) a first compound represented by the following chemical formula 1; ii) at least one π-electron deficient nitrogen-containing C1-C 60 a second compound including a cyclic group, a third compound including a group represented by the following Chemical Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof; The first compound, the second compound, the third compound, and the fourth compound are different from each other. [ka] ...(chemical formula 1) For an explanation of Chemical Formula 1, please refer to the following description of this specification. [ka] ...(chemical formula 3) In Chemical Formula 3, the ring CY 71 and KanCY 72 are independently of each other, π-electron-rich C3-C 60 a group having a ring structure or a pyridine ring structure, In Chemical Formula 3, X 71 is a single bond or a linking group containing O, S, N, B, C, Si, or any combination thereof; In Chemical Formula 3, * indicates the bonding position of the compound 3 to the adjacent atom.
[0038] CBP (4,4'-bis(9H-carbazol-9-yl)biphenyl) and mCBP (3,3'-di(9H-carbazol-9-yl)-1,1'-biphenyl) are excluded from the third compounds. [ka]
[0039] Explanation of Compounds 1 to 4 The second compound may include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, or any combination thereof.
[0040] For example, the light emitting device may further include at least one of a second compound and a third compound in addition to the first compound.
[0041] As another example, the light emitting device may further include a fourth compound in addition to the first compound.
[0042] As yet another example, the light-emitting element may contain all of the first to fourth compounds.
[0043] According to one embodiment, the intermediate layer may include a second compound, and may further include a third compound, a fourth compound, or a combination thereof in addition to the first compound and the second compound.
[0044] On the other hand, the fourth compound may be a compound in which the difference between the triplet energy level (eV) and the singlet energy level (eV) is 0 eV or more and 0.5 eV or less (or 0 eV or more and 0.3 eV or less).
[0045] For example, the fourth compound may be a compound containing at least one cyclic group containing each of B (boron) and N (nitrogen) as ring-forming atoms.
[0046] In yet another example, the fourth compound may be a C8-C cyclic ring containing two or more cyclic groups fused together while sharing a boron (B). 60 It may also be a polycyclic group-containing compound.
[0047] According to one embodiment, the fourth compound comprises one or more third rings and one or more fourth rings fused together; the third ring may be a group having a ring structure selected from cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclopentene, cyclohexene, cycloheptene, cyclooctene, adamantane, norbornene, norbornane, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane, benzene, pyridine, pyrimidine, pyridazine, pyrazine, and triazine; The fourth ring may be a group having a ring structure selected from 1,2-azaborinine, 1,3-azaborinine, 1,4-azaborinine, 1,2-dihydro-1,2-azaborinine, 1,4-oxaborinine, 1,4-thiaborinine, and 1,4-dihydroborinine.
[0048] According to other embodiments, the intermediate layer may include a fourth compound, and may further include a second compound, a third compound, or any combination thereof, in addition to the first compound and the fourth compound.
[0049] According to yet another embodiment, the intermediate layer may include a third compound, for example, the third compound does not include the compound represented by Formula 3-1 described herein.
[0050] i) the first compound and ii) the second compound, the third compound, the fourth compound, or any combination thereof may be included in the light-emitting layer in the intermediate layer.
[0051] The light-emitting layer can emit phosphorescence or fluorescence emitted from the first compound. For example, the phosphorescence or fluorescence emitted from the first compound can be blue light.
[0052] For example, the light-emitting layer of the light-emitting device includes a first compound and a second compound, and the first compound and the second compound can form an exciplex.
[0053] In yet another example, the light-emitting layer of the light-emitting device includes a first compound, a second compound, and a third compound, and the first compound and the second compound can form an exciplex.
[0054] As another example, the light emitting layer of the light emitting device may include a first compound and a fourth compound, and the fourth compound may play a role in improving color purity, luminous efficiency, and life characteristics of the light emitting device.
[0055] According to one embodiment, the second compound may include a compound represented by the following Chemical Formula 2: [ka] ...(chemical formula 2)
[0056] In Chemical Formula 2, L 51 ~L 53 are, independently of each other, a single bond, at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 is a heterocyclic group, b51 to b53 are each independently an integer of 1 to 5; X 54 is N or C(R 54 ) and X 55 is N or C(R 55 ) and X 56 is N or C(R 56 ) and X 54 ~X 56 At least one of the is N, R 51 ~R 56 For the explanation of each of the above, please refer to the descriptions in this specification. R 10a For the relevant explanation, please refer to the description in this specification.
[0057] According to other embodiments, the third compound may include a compound represented by the following chemical formula 3-1, a compound represented by the following chemical formula 3-2, a compound represented by the following chemical formula 3-3, a compound represented by the following chemical formula 3-4, a compound represented by the following chemical formula 3-5, or any combination thereof. [ka] ...(Chemical formula 3-1) [ka] ...(chemical formula 3-2) [ka] ...(Chemical formula 3-3) [ka] ...(Chemical formula 3-4) [ka] ...(chemical formula 3-5)
[0058] In Chemical Formula 3-1 to Chemical Formula 3-5, Ring CY 71 ~Kan CY 74 are independently of each other, π-electron-rich C3-C 60 a group having a ring structure or a pyridine ring structure, X 82 is a single bond, O, S, N-[(L 82 ) b82 -R 82 ], C(R 82a )(R 82b ) or Si(R 82a )(R 82b ) and X 83 is a single bond, O, S, N-[(L 83 ) b83 -R 83 ], C(R 83a )(R 83b ) or Si(R 83a )(R 83b ) and X 84 is O, S, N-[(L 84 ) b84 -R 84 ], C(R 84a )(R 84b ) or Si(R 84a )(R 84b) and X 85 is C or Si, L 81 ~L 85 are, independently of each other, a single bond, *-C(Q4)(Q5)-*', *-Si(Q4)(Q5)-*', at least one R 10a Substituted or unsubstituted π-electron rich C3-C 60 a cyclic group, or at least one R 10a Q4 and Q5 are described in the same specification as Q1, and b81 to b85 are each independently an integer of 1 to 5; R 71 ~R 74 , R 81 ~R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b For the explanation of each of the above, please refer to the descriptions in this specification. a71 to a74 are each independently an integer of 0 to 20, R 10a For the relevant explanation, please refer to the description in this specification.
[0059] According to yet another embodiment, the fourth compound may include a compound represented by formula 502 below, a compound represented by formula 503 below, or any combination thereof. [ka] ...(chemical formula 502) [ka] ...(chemical formula 503)
[0060] In Chemical Formula 502 and Chemical Formula 503, Ring A 501 ~Ring A 504are independent of each other, C3-C 60 Carbocyclic structure or C1-C 60 is a group having a heterocyclic structure, Y 505 is O, S, N(R 505 ), B(R 505 ), C(R 505a )(R 505b ) or Si(R 505a )(R 505b ) and Y 506 is O, S, N(R 506 ), B(R 506 ), C(R 506a )(R 506b ) or Si(R 506a )(R 506b ) and Y 507 is O, S, N(R 507 ), B(R 507 ), C(R 507a )(R 507b ) or Si(R 507a )(R 507b ) and Y 508 is O, S, N(R 508 ), B(R 508 ), C(R 508a )(R 508b ) or Si(R 508a )(R 508b ) and Y 51 and Y 52 are, independently of each other, B, P(=O) or S(=O), R 500a , R 500b , R 501 Or R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b For the explanation of each of the above, please refer to the descriptions in this specification. a501 to a504 are each independently an integer from 0 to 20, R10a For the relevant explanation, please refer to the description in this specification.
[0061] Explanation of chemical formulas In Chemical Formula 1, M is platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu).
[0062] In Chemical Formula 1, X1 to X4 are each independently C or N.
[0063] According to one embodiment, in Formula 1, X1 may be C, and C may be a carbon of a carbene moiety.
[0064] According to another embodiment, in Formula 1, X1 may be N.
[0065] According to yet another embodiment, X2 and X3 may be C and X4 may be N in Chemical Formula 1.
[0066] In Chemical Formula 1, i) the bond between X1 and M is a coordinate bond, and ii) one of the bonds between X2 and M, X3 and M, and X4 and M is a coordinate bond, and the remaining two are covalent bonds.
[0067] For example, in Chemical Formula 1, the bond between X2 and M and the bond between X3 and M may be a covalent bond, and the bond between X4 and M may be a coordinate bond.
[0068] In Chemical Formula 1, ring CY1 is a group having a ring structure selected from i) an X1-containing five-membered ring, ii) an X1-containing five-membered ring fused with at least one six-membered ring, and iii) an X1-containing six-membered ring. According to one embodiment, ring CY1 in Chemical Formula 1 may be i) an X1-containing five-membered ring, or ii) a group having a ring structure of an X1-containing five-membered ring fused with at least one six-membered ring. That is, ring CY1 may include a five-membered ring bonded to M in Chemical Formula 1 via X1.
[0069] For example, the five-membered ring containing X1 in ring CY1 of Chemical Formula 1 may be a group having a ring structure selected from pyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, and thiadiazole.
[0070] As yet another example, in ring CY1 of Chemical Formula 1, the six-membered ring that can be selectively fused to the X1-containing five-membered ring or the X1-containing six-membered ring may have a ring structure selected from benzene, pyridine, and pyrimidine.
[0071] JPEG0007796489000017.jpg37159 [ka] [ka]
[0072] In chemical formulas CY1-1 to CY1-42, Y1 is O, S, N, C or Si; * represents the bonding position to M in Chemical Formula 1; *' indicates the bonding position to the adjacent atom in Chemical Formula 1.
[0073] For example, X1 may be C in chemical formulas CY1-1 to CY1-8, and N in chemical formulas CY1-9 to CY1-42.
[0074] In Formula 1, ring CY2 is C3-C 60 Carbocyclic structure or C1-C 60 It may also be a group having a heterocyclic structure.
[0075] For example, ring CY2 may be a group having a ring structure selected from benzene, pyridine, pyrimidine, naphthalene, dibenzofuran, dibenzothiophene, carbazole, fluorene, and dibenzosilole.
[0076] JPEG0007796489000020.jpg37159 [ka]
[0077] In chemical formulas CY2-1 to CY2-11, Y2 is O, S, N, C or Si; * represents the bonding position to M in Chemical Formula 1; *' is the bonding position to ring CY1 in Chemical Formula 1, *" represents X in chemical formula 1. 51 This is the bonding position with
[0078] In Chemical Formula 1, X 31 ~X 36 , and X 41 ~X 44 are, independently of each other, C or N.
[0079] According to one embodiment, in Formula 1, X 31 ~X 36 , and X 41 ~X 44 may both be C.
[0080] In Chemical Formula 1, X 51 are *-N(R5)-*', *-B(R5)-*', *-P(R5)-*', *-C(R 5a )(R 5b )-*', *-Si(R 5a )(R 5b )-*', *-Ge(R 5a )(R 5b)-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R5)=*', *=C(R5)-*', *-C(R 5a )=C(R 5b )-*', *-C(=S)-*' or *-C≡C-*'. * and *' are the bonding positions to adjacent atoms. 5a and R 5b For the explanation of each of these, please refer to the respective descriptions in this specification. 5a and R 5b are selectively bonded to each other and at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 A heterocyclic group can be formed (see, for example, compound 109 below).
[0081] According to one embodiment, in Formula 1, X 51 are *-N(R5)-*', *-B(R5)-*', *-C(R 5a )(R 5b )-*', *-Si(R 5a )(R 5b )-*', *-S-*' or *-O-*'.
[0082] In Chemical Formula 1, L1 is a single bond, at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 It is a heterocyclic group.
[0083] In Chemical Formula 1, b1 represents the number of L1 and is an integer of 1 to 5. When b1 is 2 or more, the two or more L1 may be the same or different. For example, b1 may be 1 or 2.
[0084] In Chemical Formula 1, R1 to R5, R5a and R 5b are each independently a group represented by the following chemical formula 1-1, a group represented by the following chemical formula 1-2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, at least one R 10a Substituted or unsubstituted C1-C 60 alkyl group, at least one R 10a Substituted or unsubstituted C2-C 60 alkenyl group, at least one R 10a Substituted or unsubstituted C2-C 60 an alkynyl group, at least one R 10a Substituted or unsubstituted C1-C 60 an alkoxy group, at least one R 10a Substituted or unsubstituted C3-C 60 Carbocyclic group, at least one R 10a Substituted or unsubstituted C1-C 60 Heterocyclic group, at least one R 10a Substituted or unsubstituted C6-C 60 an aryloxy group, at least one R 10a Substituted or unsubstituted C6-C 60 an arylthio group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2). [ka] ...(chemical formula 1-1) [ka] ...(Chemical formula 1-2)
[0085] For the explanation of Chemical Formula 1-1 and Chemical Formula 1-2, please refer to the description in this specification.
[0086] In Chemical Formula 1, c1 is an integer of 0 to 5, a1 and a4 are each independently an integer of 0 to 4, a2 is an integer of 0 to 10, and a3 is an integer of 0 to 6. The sum of a1 to a4 is 1 or more, and a1 *-(L1) b1 -(R1) c1 At least one of the groups represented by the formula (a), at least one of the a2 R2s, at least one of the a3 R3s, at least one of the a4 R4s, or any combination thereof, is independently a group represented by the formula (1-1) or a group represented by the formula (1-2). That is, the organometallic compound represented by the formula (1) necessarily contains a group represented by the formula (1-1), a group represented by the formula (1-2), or any combination thereof.
[0087] According to one embodiment, in Chemical Formula 1, a4 is an integer of 1 to 4, and at least one of the a4 R4s may be, independently of one another, a group represented by Chemical Formula 1-1 or a group represented by Chemical Formula 1-2.
[0088] In Chemical Formula 1, L7 is a single bond, at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 It is a heterocyclic group.
[0089] In Chemical Formula 1, b7 represents the number of L7 and is an integer of 1 to 5. When b7 is 2 or more, the two or more L7 may be the same or different. For example, b7 may be 1 or 2.
[0090] In Chemical Formula 1-1 and Chemical Formula 1-2, ring CY7 is C3-C 60 Carbocyclic structure or C1-C 60 It may also be a group having a heterocyclic structure.
[0091] According to one embodiment, in Chemical Formula 1-1 and Chemical Formula 1-2, ring CY7 is i) a first ring, ii) a second ring, iii) a fused ring in which two or more first rings are fused to each other, iv) a fused ring in which two or more second rings are fused to each other, or v) a fused ring in which one or more first rings and one or more second rings are fused to each other; the first ring may be a group having a ring structure selected from cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclopentene, cyclohexene, cycloheptene, cyclooctene, adamantane, norbornene, norbornane, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane, and benzene; The second ring may be a group having a ring structure selected from pyrrole, furan, thiophene, silole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiadiazole, pyridine, pyrimidine, pyridazine, pyrazine, triazine, 1,2-azaborinine, 1,3-azaborinine, 1,4-azaborinine, 1,2-dihydro-1,2-azaborinine, 1,4-oxaborinine, 1,4-thiaborinine, and 1,4-dihydroborinine.
[0092] According to other embodiments, in Chemical Formula 1-1 and Chemical Formula 1-2, ring CY7 may be a group having a ring structure selected from benzene, naphthalene, phenanthrene, carbazole, [1,2]azaborinino[1,2-a][1,2]azaborinine, and benzo[1,2]azaborinino[1,2-a][1,2]azaborinine.
[0093] According to still another embodiment, in Chemical Formula 1-1 and Chemical Formula 1-2, ring CY7 may be a group represented by one of the following Chemical Formulas CY7-1 to CY7-33. [ka] [ka] [ka]
[0094] In Chemical Formulae CY7-1 to CY7-33, * indicates the bonding position with L7 in Chemical Formulae 1-1 and 1-2.
[0095] JPEG0007796489000027.jpg63161
[0096] Ring CY8 in formula 1-1 is a non-aromatic C3-C 60 Carbocyclic or non-aromatic C1-C 60 It may also be a group having a heterocyclic structure.
[0097] According to one embodiment, ring CY8 in Chemical Formula 1-1 may be a group having a ring structure selected from cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclopentene, cyclohexene, cycloheptene, cyclooctene, adamantane, norbornene, norbornane, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, and bicyclo[2.2.2]octane.
[0098] According to another embodiment, ring CY8 in chemical formula 1-1 may be a group represented by one of the following chemical formulas CY8-1 to CY8-8. [ka]
[0099] In Chemical Formulae CY8-1 to CY8-8, * indicates the bonding position to the adjacent atom in Chemical Formula 1-1, and *' indicates the bonding position to L7 in Chemical Formula 1-1.
[0100] In Chemical Formula 1-1 and Chemical Formula 1-2, the explanations for R7 to R9 can refer to the explanations for R1 in this specification.
[0101] In Chemical Formula 1-1 and Chemical Formula 1-2, a7 and a8 represent the number of R7 and R8, respectively, and are each independently an integer of 0 to 20. When a7 is 2 or more, two or more R7s may be the same or different from each other, and when a8 is 2 or more, two or more R8s may be the same or different from each other.
[0102] In Chemical Formula 1, i) a1 *-(L1) b1 -(R1) c1 Two or more of the groups represented by the formula (I) may be optionally linked to each other (via a single bond, a double bond, or a first linking group), and at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 ii) two or more of the a2 R2 may optionally be bonded to each other (via a single bond, a double bond, or a first linking group), and at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 a) a) R3 may form a heterocyclic group; and iii) two or more of the a3 R3 may be optionally bonded to each other (via a single bond, a double bond, or a first linking group), and at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 a) a) two or more of the a) R may optionally be bonded to each other (via a single bond, a double bond, or a first linking group), and at least one R 10a Substituted or unsubstituted C3-C 60a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 v) the above-mentioned R1 to R5, R 5a and R 5b two or more of the R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 The first linking group can form a heterocyclic group. 95 )-*', *-B(R 95 )-*', *-P(R 95 )-*', *-C(R 95a )(R 95b )-*', *-Si(R 95a )(R 95b )-*', *-Ge(R 95a )(R 95b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 95 )=*', *=C(R 95 )-*', *-C(R 95a )=C(R 95b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R95)=*', *=C(R95)-*', *-C(R95a)=C(R95b)-*', *-C(=S)-*' and *-C≡C-*'; 95 , R 95a and R 95b The explanations regarding these are given in this specification under the headings R 10a Please refer to the explanation related to this.
[0103] According to one embodiment, the first compound represented by Formula 1 may include at least one deuterium atom.
[0104] According to another embodiment, the group represented by Chemical Formula 1-1 and the group represented by Chemical Formula 1-2 may each contain at least one deuterium.
[0105] According to yet another embodiment, in Chemical Formula 1, 1) a1 is not 0, 2) a1 times *-(L1) b1 -(R1) c1 At least one of *-(L1) b1 -(R1) c1 In the formula, i) L1 is not a single bond, ii) at least one of c1 R1 is at least one R 10a Substituted or unsubstituted C3-C 60 Carbocyclic group, at least one R10a Substituted or unsubstituted C1-C 60 It may also be a heterocyclic group.
[0106] According to yet another embodiment, in Chemical Formula 1, *-(L1) b1 -(R1) c1 The group represented by may contain at least one deuterium.
[0107] JPEG0007796489000029.jpg45159 [ka]
[0108] In chemical formulas CY1(1) to CY1(6), For the description of X1, please refer to the description in this specification. L 11 For the explanation of L1 and c11, refer to the explanation of L1 and c1 in this specification, respectively. R 11 ~R 13 For the explanation of each of the above, please refer to the explanation of R1 in this specification. * represents the bonding position to M in Chemical Formula 1; *' indicates the bonding position to the adjacent atom in Chemical Formula 1. However, R11 ~R 13 Each of is not hydrogen.
[0109] According to one embodiment, in the chemical formula CY1(1) to the following chemical formula CY1(4), 1) L 11 is not a single bond, 2) c11 R 11 At least one of the 10a Substituted or unsubstituted C3-C 60 Carbocyclic group, at least one R10a Substituted or unsubstituted C1-C 60 It may also be a heterocyclic group.
[0110] For example, X1 may be C in the chemical formulas CY1(1) to CY1(4), and N in the chemical formulas CY1(5) and CY1(6).
[0111] As another example, in the chemical formulas CY1(1) to CY1(5), L 11 is at least one R 10a Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 30 It may also be a heterocyclic group.
[0112] JPEG0007796489000031.jpg45159 [ka] [ka]
[0113] In chemical formulas CY2(1) to CY2(26), For an explanation of X2, please refer to the description in this specification. X 21 is S, N(R 21 ), C(R 21 )(R22 ) or Si(R 21 )(R 22 ) and R 21 ~R 23 For the explanation of each of the above, refer to the explanation of R2 in this specification. * represents the bonding position to M in Chemical Formula 1; *' is the bonding position to ring CY1 in Chemical Formula 1, *" represents X in chemical formula 1. 51 This is the bonding position with However, R 21 ~R 23 Each of is not hydrogen.
[0114] JPEG0007796489000034.jpg49165 [ka]
[0115] In chemical formulas CY3(1) to CY3(7), For a description of X3, please refer to the description in this specification. R 31 ~R 36 For the explanation of each of the above, refer to the explanation of R3 in this specification. * represents the bonding position to M in Chemical Formula 1; *' is the bonding position to the adjacent atom in chemical formula 1, *" represents X in chemical formula 1. 51 This is the bonding position with However, R 31 ~R 36 Each of is not hydrogen.
[0116] JPEG0007796489000036.jpg37161 [ka]
[0117] In chemical formulas CY4(1) to CY4(8), For a description of X4, please refer to the description in this specification. T4 is a group represented by Chemical Formula 1-1 or a group represented by Chemical Formula 1-2, R 41 , R 43 and R 44 For the explanation of each of the above, refer to the explanation of R4 in this specification. * represents the bonding position to M in Chemical Formula 1; *' indicates the bonding position to the adjacent atom in Chemical Formula 1. However, R 41 , R 43 and R 44 Each of is not hydrogen.
[0118] In chemical formula 2, b51 to b53 are each L 51 ~L 53 b51 indicates the number of Ls, and is an integer between 1 and 5. If b51 is 2 or more, 51 are identical or different, and if b52 is 2 or more, then 2 or more L 52 are identical or different, and if b53 is 2 or more, then 2 or more L 53 may be the same as or different from each other. For example, b51 to b53 may be 1 or 2 independently.
[0119] In Chemical Formula 1 and Chemical Formula 2, L1, L7, and L 51 ~L 53 are independent of each other, a single bond; or Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl groups, C1-C 20Alkoxy group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, triazinyl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, dimethyldibenzosilolyl group, diphenyldibenzosilolyl group, -O(Q 31 ), -S(Q 31 ), -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -P(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), -P(=O)(Q 31 )(Q 32), or a phenylene group, a naphthylene group, an anthracenylene group, a phenanthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a cyclopentadienylene group, a furanylene group, a thiophenylene group, a silolylene group, an indenylene group, a fluorenylene group, an indolylene group, a carbazolylene group, a benzofuranylene group, a dibenzofuranylene group, a benzothiophene group, or a substituted or unsubstituted phenylene ... an nylene group, a dibenzothiophenylene group, a benzosilolylene group, a dibenzosilolylene group, an azafluorenylene group, an azacarbazolylene group, an azadibenzofuranylene group, an azadibenzothiophenylene group, an azadibenzosilolylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, and a phenanthrolinylene group, pyrrolylene group, pyrazolylene group, imidazolylene group, triazolylene group, oxazolylene group, isoxazolylene group, thiazolylene group, isothiazolylene group, oxadiazolylene group, thiadiazolylene group, benzopyrazolylene group, benzimidazolylene group, benzoxazolylene group, benzothiazolylene group, benzoxadiazolylene group, benzothiadiazolylene group, dibenzoxasilinylene group, dibenzothiaasilinylene a group, a dibenzodihydroazasilinylene group, a dibenzodihydrodisilinylene group, a dibenzodihydrosilinylene group, a dibenzodioxynylene group, a dibenzoxathiinylene group, a dibenzooxazinylene group, a dibenzopyranylene group, a dibenzodithiinylene group, a dibenzothiazinylene group, a dibenzothiopyranylene group, a dibenzocyclohexadienylene group, a dibenzodihydropyridinylene group or a dibenzodihydropyrazinylene group; Q 31 ~Q 33 are, independently of each other, hydrogen, deuterium, C1-C 20 Alkyl groups, C1-C 20 It is an alkoxy group, a phenyl group, a biphenylyl group, a terphenylyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group or a triazinyl group.
[0120] According to one embodiment, in Formula 2, L51 and R 51 Bond with L 52 and R 52 Bond with L 53 and R 53 Bonds with 2 or more L 51 Bonds between 2 or more L 52 Bonds between 2 or more L 53 The bond between L 51 and X in chemical formula 2 54 and X 55 The bond between the carbon and L 52 and X in chemical formula 2 54 and X 56 The bond between the carbon and L 53 and X in chemical formula 2 55 and X 56 The carbon bonds between the carbon atoms may each be a "carbon-carbon single bond."
[0121] In Chemical Formula 2, X 54 is N or C(R 54 ) and X 55 is N or C(R 55 ) and X 56 is N or C(R 56 ) and X 54 ~X 56 At least one of R is N. 54 ~R 56 For the explanation of X, please refer to the description in this specification. 54 ~X 56 Two or three of the may be N.
[0122] As used herein, R 51 ~R 56 , R 71 ~R 74 , R 81 ~R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b , R 500a , R 500b , R 501 ~R 508, R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, at least one R 10a substituted or unsubstituted, substituted or unsubstituted C1-C 60 alkyl group, at least one R 10a substituted or unsubstituted, substituted or unsubstituted C2-C 60 alkenyl group, at least one R 10a substituted or unsubstituted, substituted or unsubstituted C2-C 60 an alkynyl group, at least one R 10a substituted or unsubstituted, substituted or unsubstituted C1-C 60 an alkoxy group, at least one R 10a Substituted or unsubstituted C3-C 60 Carbocyclic group, at least one R10a Substituted or unsubstituted C1-C 60 Heterocyclic group, at least one R 10a Substituted or unsubstituted C6-C 60 an aryloxy group, at least one R 10a Substituted or unsubstituted C6-C 60 An arylthio group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2). For explanations of Q1 to Q3, please refer to the descriptions in this specification.
[0123] For example, i) in Chemical Formula 1, the remaining R1 to R5, R 5a , R 5b and R7 to R9, ii) in Chemical Formula 2, Chemical Formula 3-1 to Chemical Formula 3-5, Chemical Formula 502 and Chemical Formula 503, R 51 ~R56 , R 71 ~R 74 , R 81 ~R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b , R 500a , R 500b , R 501 ~R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b , and iii) R 10a are independent of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl group or C1-C 20 alkoxy groups; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, C1-C 10 C1-C substituted with an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenylyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof 20 Alkyl group or C1-C 20 alkoxy groups; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl groups, C1-C 20Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenylyl group, C1-C 10 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzo Quinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, -O(Q 31 ), -S(Q 31 ), -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -P(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), -P(=O)(Q 31 )(Q 32 ), or any combination thereof, substituted or unsubstituted, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantanyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenylyl, C1-C10 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazo a aryl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, an azadibenzosilolyl group, or a group represented by formula 91; or -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2); Q1 to Q3, and Q 31 ~Q 33 are independent of each other, -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H or -CD2CDH2; or Deuterium, C1-C 10The alkyl group may be an alkyl group, a phenyl group, a biphenylyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, which may be substituted or unsubstituted with any combination thereof. [ka] ...(chemical formula 91)
[0124] In chemical formula 91, Ring CY 91 and KanCY 92 are, independently of each other, at least one R 10a Substituted or unsubstituted C5-C 30 Carbocyclic structure or at least one R 10a Substituted or unsubstituted C1-C 30 is a group having a heterocyclic structure, X 91 is a single bond, O, S, N(R 91 ), B(R 91 ), C(R 91a )(R 91b ) or Si(R 91a )(R 91b ) and R 91 , R 91a and R 91b The explanations regarding these are given in this specification under the headings R 82 , R 82a and R 82b Please refer to the explanation regarding R 10a For a description of the above, please refer to the description in this specification. * indicates the bond position to the adjacent atom.
[0125] For example, in formula 91: Ring CY 91 and KanCY 92are, independently of each other, at least one R 10a a group having a ring structure selected from benzene, pyridine, pyrimidine, pyrazine, pyridazine and triazine, which is substituted or unsubstituted by R 91 , R 91a and R 91b are independent of each other, Hydrogen or C1-C 10 an alkyl group; or Deuterium, C1-C 10 The alkyl group may be an alkyl group, a phenyl group, a biphenylyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or a phenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, which may be unsubstituted or substituted with any combination thereof.
[0126] According to another embodiment, i) in Chemical Formula 1, the remaining R1 to R5, R 5a , R 5b and R7 to R9, ii) in Chemical Formula 2, Chemical Formula 3-1 to Chemical Formula 3-5, Chemical Formula 502 and Chemical Formula 503, R 51 ~R 56 , R 71 ~R 74 , R 81 ~R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b , R 500a , R 500b , R 501 ~R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b , and iii) R 10amay be, independently of one another, hydrogen, deuterium, -F, a cyano group, a nitro group, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a group represented by one of the following chemical formulas 9-1 to 9-19, a group represented by one of the following chemical formulas 10-1 to 10-246, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), or -P(=O)(Q1)(Q2) (however, for explanations of Q1 to Q3, see the description in this specification). [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0127] In Chemical Formula 9-1 to Chemical Formula 9-19 and Chemical Formula 10-1 to Chemical Formula 10-246, * indicates the bonding position to the adjacent atom, Ph is a phenyl group, and TMS is a trimethylsilyl group.
[0128] In chemical formulas 3-1 to 3-5, chemical formula 502, and chemical formula 503, a71 to a74, and a501 to a504 are R 71 ~R 74 , and R 501 ~R 504 a71 represents the number of R 71 may be the same or different from each other, and when a72 is 2 or more, two or more R 72 may be the same as or different from each other, and when a73 is 2 or more, two or more R 73 may be the same as or different from each other, and when a74 is 2 or more, two or more R 74 may be the same as or different from each other. When a501 is 2 or more, two or more R 501 may be the same as or different from each other, and when a502 is 2 or more, two or more R 502 may be the same as or different from each other, and when a503 is 2 or more, two or more R 503 may be the same as or different from each other, and when a504 is 2 or more, two or more R 504 The above-mentioned a71 to a74 and a501 to a504 are each independently an integer of 0 to 8.
[0129] In chemical formula 1, i) a1 *-(L1) b1 -(R1) c1 Two or more of the groups represented by the formula may be optionally linked to each other (via a single bond, a double bond, or a first linking group), and at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 ii) two or more of the a2 R2 may optionally be bonded to each other (via a single bond, a double bond, or a first linking group), and at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 a) two or more of the a) R may optionally be bonded to each other (via a single bond, a double bond, or a first linking group), and at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 a) a) two or more of the a) R may optionally be bonded to each other (via a single bond, a double bond, or a first linking group), and at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 v) the above-mentioned R1 to R5, R 5a and R 5b Two or more of the R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 The first linking group can form a heterocyclic group. 95 )-*', *-B(R95 )-*', *-P(R 95 )-*', *-C(R 95a )(R 95b )-*', *-Si(R 95a )(R 95b )-*', *-Ge(R 95a )(R 95b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 95 )=*', *=C(R 95 )-*', *-C(R 95a )=C(R 95b )-*', *-C(=S)-*' and *-C≡C-*', and 95 , R 95a and R 95b The explanations regarding R1 in this specification refer to the explanations regarding R2.
[0130] On the other hand, in Chemical Formula 2, *-(L 51 ) b51 -R 51 and *-(L 52 ) b52 -R 52 The group represented by is not a phenyl group.
[0131] According to one embodiment, in Formula 2, *-(L 51 ) b51 -R 51 and *-(L 52 ) b52 -R 52 The groups represented by may be the same as each other.
[0132] According to another embodiment, in Formula 2, *-(L 51 ) b51 -R 51 and *-(L 52 ) b52 -R 52 The groups represented by may be different from each other.
[0133] According to another embodiment, in Chemical Formula 2, b51 and b52 are 1, 2 or 3; 51 and L 52 are, independently of each other, at least one R 10a The group may be a phenylene group, a pyridinylene group, a pyrimidinylene group, a pyridazinylene group, a pyrazinylene group, or a triazinylene group, which may be substituted or unsubstituted by one of the following:
[0134] For example, in Formula 2, R 51 and R 52 are, independently of each other, at least one R 10a Substituted or unsubstituted C3-C 60 Carbocyclic group, at least one R 10a Substituted or unsubstituted C1-C 60 Heterocyclic group, at least one R 10a Substituted or unsubstituted C6-C 60 an aryloxy group, at least one R 10a Substituted or unsubstituted C6-C 60 an arylthio group, -C(Q1)(Q2)(Q3) or -Si(Q1)(Q2)(Q3); Q1 to Q3 are each independently deuterium, -F, a cyano group, C1-C 60 Alkyl groups, C1-C 60 C3-C substituted or unsubstituted with alkoxy, phenyl, biphenylyl, or any combination thereof 60 Carbocyclic group or C1-C 60 It may also be a heterocyclic group.
[0135] According to one embodiment, In Chemical Formula 2, *-(L 51 ) b51 -R 51 is a group represented by one of the following chemical formulas CY51-1 to CY51-26, and / or In the above Chemical Formula 2, *-(L 52 ) b52 -R 52is a group represented by one of the following chemical formulas CY52-1 to CY52-26, and / or In the above Chemical Formula 2, *-(L 53 ) b53 -R 53 The group represented by may be a group represented by one of the following chemical formulas CY53-1 to CY53-27, -C(Q1)(Q2)(Q3), or -Si(Q1)(Q2)(Q3). [ka] [ka] [ka] [ka] [ka] [ka]
[0136] In chemical formulas CY51-1 to CY51-26, chemical formulas CY52-1 to CY52-26, and chemical formulas CY53-1 to CY53-27, Y 63 is a single bond, O, S, N(R 63 ), B(R 63 ), C(R 63a )(R 63b ) or Si(R 63a )(R 63b ) and Y 64 is a single bond, O, S, N(R 64 ), B(R 64 ), C(R 64a )(R 64b ) or Si(R 64a )(R64b ) and Y 67 is a single bond, O, S, N(R 67 ), B(R 67 ), C(R 67a )(R 67b ) or Si(R 67a )(R 67b ) and Y 68 is a single bond, O, S, N(R 68 ), B(R 68 ), C(R 68a )(R 68b ) or Si(R 68a )(R 68b ) and In the chemical formula CY51-16 and the chemical formula CY51-17, Y 63 and Y 64 is not a single bond at the same time, In the chemical formula CY52-16 and the chemical formula CY52-17, Y 67 and Y 68 is not a single bond at the same time, R 51a ~R 51e , R 61 ~R 64 , R 63a , R 63b , R 64a and R 64b The explanations regarding these are given in this specification under the headings R 51 Please refer to the explanation regarding R 52a ~R 52e , R 65 ~R 68 , R 67a , R 67b , R 68a and R 68b The explanations regarding these are given in this specification under the headings R 52 Please refer to the explanation regarding R 53a ~R 53e , R 69a and R 69b The explanations regarding these are given in this specification under the headings R 53 Please refer to the explanation regarding * indicates the bond position to the adjacent atom. However, R51a ~R 51e Each of the is not hydrogen, but R 52a ~R 52e Each of the is not hydrogen, but R 53a ~R 53e Each of is not hydrogen.
[0137] for example, In chemical formulas CY51-1 to CY51-26 and chemical formulas CY52-1 to CY52-26, R 51a ~R 51e , and R 52a ~R 52e are independent of each other, Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenylyl group, C1-C 10Alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenylyl group, a C1-C6 alkyl group, a C1-C6 aryl ... 10Alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazo a aryl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, an azadibenzosilolyl group, or a group represented by formula 91; or -C(Q1)(Q2)(Q3) or -Si(Q1)(Q2)(Q3); Q1 to Q3 are independently deuterium, C1-C 10 a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, which is unsubstituted or substituted with an alkyl group, a phenyl group, a biphenylyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, or any combination thereof; In the chemical formula CY51-16 and the chemical formula CY51-17, i) Y 63 is O or S, and Y 64 is Si(R 64a )(R 64b ) or ii) Y 63 is Si(R 63a )(R 63b ) and Y 64 is O or S, In the chemical formula CY52-16 and the chemical formula CY52-17, i) Y 67 is O or S, and Y 68 is Si(R 68a )(R 68b ) or ii) Y 67 is Si(R 67a )(R 67b ) and Y 68 may be O or S.
[0138] On the other hand, in Chemical Formula 3-1 to Chemical Formula 3-5, L 81 ~L 85 are independent of each other, Single bond; *-C(Q4)(Q5)-*' or *-Si(Q4)(Q5)-*'; or Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, triazinyl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, dimethyldibenzosilolyl group, diphenyldibenzosilolyl group, -O(Q 31 ), -S(Q 31 ), -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -P(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), -P(=O)(Q 31 )(Q 32), or a phenylene group, naphthylene group, anthracenylene group, phenanthrenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, cyclopentadienylene group, furanylene group, thiophenylene group, silolylene group, indenylene group, fluorenylene group, indolylene group, carbazolylene group, benzofuranylene group, dibenzofuranylene group, benzothiophenylene group, dibenzothiophenylene group, benzosilolylene group, dibenzosilolylene group, azafluorenylene group, azacarbazolylene group, azadibenzofuranylene group, azadibenzothiophenylene group, a group, an azadibenzosilolylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a phenanthrolinylene group, a pyrrolylene group, a pyrazolylene group, an imidazolylene group, a triazolylene group, an oxazolylene group, an isoxazolylene group, a thiazolylene group, an isothiazolylene group, an oxadiazolylene group, a thiadiazolylene group, a benzopyrazolylene group, a benzimidazolylene group, a benzoxazolylene group, a benzothiazolylene group, a benzoxadiazolylene group, or a benzothiadiazolylene group; Q4, Q5, Q 31 ~Q 33 are, independently of each other, hydrogen, deuterium, C1-C 20 Alkyl groups, C1-C 20 It is an alkoxy group, a phenyl group, a biphenylyl group, a terphenylyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group or a triazinyl group.
[0139] JPEG0007796489000059.jpg223159 [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0140] In the chemical formulas CY71-1(1) to CY71-1(8), CY71-2(1) to CY71-2(8), CY71-3(1) to CY71-3(32), CY71-4(1) to CY71-4(32), and CY71-5(1) to CY71-5(8), X 81 ~X 85 , L 81 , b81, R 81 and R 85 For the explanation of each of the above, please refer to the descriptions in this specification. X 86 is a single bond, O, S, N(R 86 ), B(R 86 ), C(R 86a )(R 86b ) or Si(R 86a )(R 86b ) and X 87 is a single bond, O, S, N(R 87 ), B(R 87 ), C(R 87a )(R 87b ) or Si(R 87a )(R 87b ) and In the chemical formulas CY71-1(1) to CY71-1(8) and CY71-4(1) to CY71-4(32), X 86 and X 87 is not a single bond at the same time, X 88 is a single bond, O, S, N(R 88 ), B(R 88 ), C(R 88a )(R 88b ) or Si(R 88a )(R 88b ) and X 89 is a single bond, O, S, N(R 89 ), B(R 89 ), C(R 89a )(R 89b ) or Si(R 89a )(R 89b ) and In the chemical formulas CY71-2(1) to CY71-2(8), CY71-3(1) to CY71-3(32), and CY71-5(1) to CY71-5(8), X 88 and X 89 is not a single bond at the same time, R 86 ~R 89 , R 86a , R 86b , R 87a , R 87b , R 88a , R 88b , R 89a and R 89b The explanations regarding these are given in this specification under the headings R 81 Please refer to the explanation related to this.
[0141] Specific examples of compounds According to one embodiment, the first compound (the organometallic compound represented by Chemical Formula 1) may include at least one of Compound D1 to Compound D315 below, at least one of Compound 1 to Compound 120 below, or any combination thereof. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
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[0142] According to another embodiment, the second compound may include at least one of the following compounds ETH1 to ETH84: [ka] [ka] [ka] [ka] [ka] [ka]
[0143] According to yet another embodiment, the third compound may include at least one of the following compounds HTH1 to HTH52: [ka] [ka] [ka] [ka]
[0144] According to yet another embodiment, the fourth compound may include at least one of the following compounds DFD1 to DFD14. [ka] JPEG0007796489000111.jpg3070
[0145] JPEG0007796489000112.jpg57154
[0146] According to one embodiment, the light emitting device can satisfy at least one of the following <Condition 1> to <Condition 4>.
[0147] <Condition 1> LUMO (lowest unoccupied molecular orbital) energy level (eV) of the third compound > LUMO energy level (eV) of the first compound <Condition 2> LUMO energy level of the first compound (eV) > LUMO energy level of the second compound (eV) <Condition 3> HOMO (highest occupied molecular orbital) energy level (eV) of the first compound > HOMO energy level (eV) of the third compound <Condition 4> HOMO energy level of the third compound (eV) > HOMO energy level of the second compound (eV)
[0148] The HOMO energy level and the LUMO energy level of each of the first compound, the second compound, and the third compound are negative values, and are measured by a known method, for example, the method described in Evaluation Example 1 in this specification.
[0149] According to other embodiments, the absolute value of the difference between the LUMO energy level of the first compound and the LUMO energy level of the second compound may be 0.1 eV or more and 1.0 eV or less, or the absolute value of the difference between the LUMO energy level of the first compound and the LUMO energy level of the third compound may be 0.1 eV or more and 1.0 eV or less, and the absolute value of the difference between the HOMO energy level of the first compound and the HOMO energy level of the second compound may be 1.25 eV or less (e.g., 1.25 eV or less and 0.2 eV or more), or the absolute value of the difference between the HOMO energy level of the first compound and the HOMO energy level of the third compound may be 1.25 eV or less (e.g., 1.25 eV or less and 0.2 eV or more).
[0150] By satisfying the above-mentioned relationship between the LUMO energy level and the HOMO energy level, the injection balance of holes and electrons in the light-emitting layer is realized.
[0151] The light emitting device may have the structure of the following first or second embodiment.
[0152] Description of the first embodiment According to a first embodiment, the first compound is included in an emitting layer in an intermediate layer of a light-emitting device, and the emitting layer further includes a host, where the first compound and the host are different from each other, and the emitting layer can emit phosphorescence or fluorescence emitted from the first compound. That is, according to the first embodiment, the first compound is a dopant or an emitter. For example, the first compound is a phosphorescent dopant or a phosphorescent emitter.
[0153] The phosphorescence or fluorescence emitted from the first compound may be blue light.
[0154] The light-emitting layer may further include an auxiliary dopant, which can effectively transfer energy to the first compound, which is a dopant or emitter, and improve the light-emitting efficiency from the first compound.
[0155] The assisting dopant may be different from the first compound and the host.
[0156] For example, the co-dopant may be a delayed fluorescent emitting compound.
[0157] As another example, the auxiliary dopant may be a compound containing at least one cyclic group containing B (boron) and N (nitrogen) as ring-forming atoms, respectively.
[0158] Description of the second embodiment According to the second embodiment, the first compound is included in an emission layer in an intermediate layer of the light-emitting device, and the emission layer further includes a host and a dopant, the first compound, the host, and the dopant being different from each other, and the emission layer can emit phosphorescence or fluorescence (e.g., delayed fluorescence) emitted from the dopant.
[0159] For example, in the second embodiment, the first compound may not be a dopant but may act as an auxiliary dopant that transfers energy to the dopant (or emitter).
[0160] As another example, in the second embodiment, the first compound may function as a dopant (or an emitter) and also as an auxiliary dopant that transfers energy to the dopant (or the emitter).
[0161] For example, in the second embodiment, the phosphorescence or fluorescence emitted from the dopant (or emitter) may be blue phosphorescence or blue fluorescence (e.g., blue delayed fluorescence).
[0162] In the second embodiment, the dopant (or emitter) may be a phosphorescent dopant material (e.g., an organometallic compound represented by Chemical Formula 1, an organometallic compound represented by Chemical Formula 401, or any combination thereof, as used herein), or any fluorescent dopant material (e.g., a compound represented by Chemical Formula 501, a compound represented by Chemical Formula 502, a compound represented by Chemical Formula 503, or any combination thereof, as used herein).
[0163] In the first and second embodiments, the blue light may be blue light having a maximum emission wavelength in the range of 390 nm to 500 nm, 410 nm to 490 nm, 430 nm to 480 nm, 440 nm to 475 nm, or 455 nm to 470 nm.
[0164] In the first embodiment, the assisting dopant may include, for example, a fourth compound represented by Formula 502 or Formula 503 herein.
[0165] In the first and second embodiments, the host may be any host material (e.g., a compound represented by Formula 301, a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof, as used herein).
[0166] Alternatively, in the first and second embodiments, the host may be the second compound, the third compound, or any combination thereof described herein.
[0167] According to yet another embodiment, the light emitting device may further include at least one of a first capping layer disposed on the outside of the first electrode and a second capping layer disposed on the outside of the second electrode, and at least one of the first capping layer and the second capping layer may include the organometallic compound represented by Chemical Formula 1. For further details regarding the first capping layer and / or the second capping layer, please refer to the descriptions herein.
[0168] According to one embodiment, the light emitting device comprises: a first capping layer disposed on the outer side of the first electrode, the first capping layer comprising an organometallic compound represented by Chemical Formula 1; a second capping layer disposed on the outside of the second electrode, the second capping layer comprising an organometallic compound represented by Formula 1; or The first capping layer and the second capping layer may be included.
[0169] In this specification, "(the intermediate layer and / or the capping layer) comprises an organometallic compound represented by Chemical Formula 1" can also be interpreted as "(the intermediate layer and / or the capping layer) may comprise one organometallic compound belonging to the category of Chemical Formula 1, or two or more different organometallic compounds belonging to the category of Chemical Formula 1."
[0170] For example, the intermediate layer and / or capping layer may contain only Compound D1 as the organometallic compound. In this case, Compound D1 may be contained in the light-emitting layer of the light-emitting device. Alternatively, the intermediate layer may contain Compound D1 and Compound D2 as the organometallic compounds. In this case, Compound D1 and Compound D2 may be contained in the same layer (e.g., Compound D1 and Compound D2 may both be contained in the light-emitting layer) or in different layers (e.g., Compound D1 may be contained in the light-emitting layer and Compound D2 may be contained in the electron transport region).
[0171] In this specification, the term "intermediate layer" refers to any single and / or multiple layers disposed between a first electrode and a second electrode in a light-emitting element.
[0172] According to yet another embodiment, there is provided an electronic device including the above-described light-emitting element. The electronic device may further include a thin film transistor. For example, the electronic device may further include a thin film transistor including a source electrode and a drain electrode, and the first electrode of the light-emitting element may be electrically connected to the source electrode or the drain electrode. Meanwhile, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. For further details regarding the electronic device, please refer to the descriptions herein.
[0173] According to yet another embodiment, there is provided an organometallic compound represented by Chemical Formula 1. The description of Chemical Formula 1 is incorporated herein by reference.
[0174] In the organometallic compound represented by chemical formula 1, the sum of a1 to a4 is 1 or more, and a1 *-(L1) b1 -(R1) c1 At least one of the groups represented by the formula (I), at least one of the a2 R2s, at least one of the a3 R3s, at least one of the a4 R4s, or any combination thereof, are independently a group represented by the following chemical formula 1-1 or a group represented by the following chemical formula 1-2. [ka] ...(chemical formula 1-1) [ka] ...(Chemical formula 1-2)
[0175] That is, the organometallic compound represented by Chemical Formula 1 necessarily contains a group represented by Chemical Formula 1-1 and / or a group represented by Chemical Formula 1-2.
[0176] The partial structure represented by ring CY7 in Chemical Formula 1-1 and Chemical Formula 1-2, the partial structure represented by ring CY8 in Chemical Formula 1-1, and R8 and R9 in Chemical Formula 1-2 each have a high triplet energy level (e.g., a high triplet energy level of about 0.01 eV or more). As a result, in Chemical Formula 1, both energy transfer by metal-to-ligand charge transfer (MLCT) and energy transfer by intramolecular through-space charge transfer can be activated. In addition, Chemical Formula 1-1 and Chemical Formula 1-2 can have structural rigidity due to ring CY7.
[0177] Therefore, a light emitting device (e.g., an organic light emitting device) including the organometallic compound represented by Chemical Formula 1 (or the first compound represented by Chemical Formula 1) as described above can have high color purity, high luminous efficiency, low driving voltage, and long life.
[0178] According to one embodiment, the organometallic compound represented by Chemical Formula 1 can emit blue light. For example, the organometallic compound represented by Chemical Formula 1 can emit blue light having a maximum emission wavelength in the range of 390 nm to 500 nm, 410 nm to 490 nm, 430 nm to 480 nm, 440 nm to 475 nm, or 455 nm to 470 nm.
[0179] According to other embodiments, the organometallic compound represented by Chemical Formula 1 may have a color purity in which the back-emission CIEx coordinate is in the range of 0.12 to 0.15, or 0.13 to 0.14, and the back-emission CIEy coordinate is in the range of 0.06 to 0.25, 0.10 to 0.20, or 0.13 to 0.20.
[0180] Those skilled in the art will be able to recognize how to synthesize the organometallic compound represented by Chemical Formula 1 by referring to the synthesis examples and / or working examples provided below.
[0181] Explanation of Figure 1 1 is a schematic cross-sectional view of a light emitting device 10 according to an embodiment of the present invention. The light emitting device 10 includes a first electrode 110, an intermediate layer 130, and a second electrode 150. Hereinafter, the structure and manufacturing method of the light emitting device 10 according to an embodiment of the present invention will be described with reference to FIG.
[0182] <First electrode 110> A substrate may be additionally disposed below the first electrode 110 or above the second electrode 150 in FIG. 1. The substrate may be a glass substrate or a plastic substrate. The substrate may also be a flexible substrate. The substrate may include a plastic having excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.
[0183] The first electrode 110 is formed by depositing a first electrode material on the substrate using, for example, a vapor deposition method or a sputtering method. When the first electrode 110 is an anode, a high work function material that easily injects holes can be used as the first electrode material.
[0184] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. To form the first electrode 110 as a transmissive electrode, the first electrode material may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. Alternatively, to form the first electrode 110 as a semi-transmissive electrode or a reflective electrode, the first electrode material may be magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
[0185] The first electrode 110 may have a single-layer structure consisting of a single layer, or a multi-layer structure including multiple layers, for example, a three-layer structure of ITO / Ag / ITO.
[0186] <Middle class 130> An intermediate layer 130 is disposed on the first electrode 110. The intermediate layer 130 includes a light-emitting layer.
[0187] The intermediate layer 130 may further include a hole transport region disposed between the first electrode 110 and the light-emitting layer, and an electron transport region disposed between the light-emitting layer and the second electrode 150.
[0188] In addition to various organic compounds, the intermediate layer 130 may further include metal-containing compounds such as organometallic compounds, inorganic compounds such as quantum dots, and the like.
[0189] The intermediate layer 130 may include: i) two or more light-emitting units sequentially stacked between the first electrode 110 and the second electrode 150; and ii) a charge generation layer disposed between the two light-emitting units. When the intermediate layer 130 includes the light-emitting units and the charge generation layer, the light-emitting device 10 is a tandem light-emitting device.
[0190] <Hole transport region in the intermediate layer 130> The hole transport region can have i) a single layer structure consisting of a single layer made of a single material, ii) a single layer structure consisting of a single layer containing multiple different materials, or iii) a multilayer structure including multiple layers containing multiple different materials.
[0191] The hole transport region may include a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting assist layer, an electron blocking layer (EBL), or any combination thereof.
[0192] For example, the hole transport region may have a multilayer structure of a hole injection layer / hole transport layer, a hole injection layer / hole transport layer / light emitting auxiliary layer, a hole injection layer / light emitting auxiliary layer, a hole transport layer / light emitting auxiliary layer, or a hole injection layer / hole transport layer / electron blocking layer, which are stacked in this order from the first electrode 110.
[0193] The hole transport region may include a compound represented by Chemical Formula 201 below, a compound represented by Chemical Formula 202 below, or any combination thereof. [ka] ...(chemical formula 201) [ka] ...(chemical formula 202)
[0194] In Chemical Formula 201 and Chemical Formula 202, L 201 ~L 204 are, independently of each other, at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 is a heterocyclic group, L 205 *-O-*', *-S-*', *-N(Q 201 )-*', at least one R 10a Substituted or unsubstituted C1-C 20 an alkylene group, at least one R 10a Substituted or unsubstituted C2-C 20 alkenylene group, at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 is a heterocyclic group, xa1 to xa4 are each independently an integer of 0 to 5, xa5 is an integer between 1 and 10, R201 ~R 204 , and Q 201 are, independently of each other, at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 is a heterocyclic group, R 201 and R 202 is optionally a single bond, at least one R 10a a C1-C5 alkylene group substituted or unsubstituted with at least one R 10a at least one R bonded to each other via a C2-C5 alkenylene group substituted or unsubstituted with 10a Substituted or unsubstituted C8-C 60 Polycyclic groups (such as carbazolyl groups) can be formed (see, for example, compound HT16 below), R 203 and R 204 is optionally a single bond, at least one R 10a a C1-C5 alkylene group substituted or unsubstituted with at least one R 10a and at least one R 10a Substituted or unsubstituted C8-C 60 can form polycyclic groups, na1 is one of integers 1 to 4.
[0195] For example, each of chemical formula 201 and chemical formula 202 may contain at least one of groups represented by the following chemical formulas CY201 to CY217. [ka]
[0196] In chemical formulas CY201 to CY217, R 10b and R 10c The explanations regarding these are given in this specification under the headings R 10aPlease refer to the explanation of the CY 201 ~Kan CY 204 are independent of each other, C3-C 20 Carbocyclic group or C1-C 20 At least one hydrogen atom in Formulas CY201 to CY217 is a heterocyclic group, and R 10a or is unsubstituted.
[0197] According to one embodiment, in the formulas CY201 to CY217, the ring CY 201 ~Kan CY 204 may each independently be a group having a ring structure selected from benzene, naphthalene, phenanthrene, and anthracene.
[0198] According to another embodiment, each of Chemical Formula 201 and Chemical Formula 202 may include at least one of groups represented by Chemical Formulas CY201 to CY203.
[0199] According to still another embodiment, chemical formula 201 may include at least one of groups represented by chemical formulas CY201 to CY203 and at least one of groups represented by chemical formulas CY204 to CY217, respectively.
[0200] According to yet another embodiment, xa1 in formula 201 is 1, and R 201 is a group represented by one of chemical formulas CY201 to CY203, xa2 is 0, and R 202 may be a group represented by one of chemical formulas CY204 to CY207.
[0201] According to still another embodiment, each of chemical formula 201 and chemical formula 202 may not include groups represented by chemical formulas CY201 to CY203.
[0202] According to still another embodiment, each of chemical formula 201 and chemical formula 202 may not include any of the groups represented by chemical formulas CY201 to CY203, but may include at least one of the groups represented by chemical formulas CY204 to CY217.
[0203] In still another embodiment, each of chemical formula 201 and chemical formula 202 may not include groups represented by chemical formulas CY201 to CY217.
[0204] For example, the hole transport region may include one of Compounds HT1 through HT44 below, 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), or any combination thereof. [ka] [ka] [ka] [ka] [ka] [ka] [Chemical formula] [Chemical formula] [Chemical formula]
[0205] The thickness of the hole transport region may be from about 5 nm to about 1,000 nm, for example, from about 10 nm to about 400 nm. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be from about 10 nm to about 900 nm, for example, from about 10 nm to about 100 nm, and the thickness of the hole transport layer may be from about 5 nm to about 200 nm, for example, from about 10 nm to about 150 nm. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the above ranges, sufficient hole transport characteristics can be obtained without a substantial increase in the driving voltage.
[0206] The light-emission assisting layer is a layer that compensates for the optical resonance distance according to the wavelength of the light emitted from the light-emitting layer and improves the light emission efficiency, and the electron blocking layer is a layer that prevents the injection of electrons from the electron transport region. The light-emission assisting layer and the electron blocking layer may contain substances such as those included in the above-described hole transport region.
[0207] <p-type dopant> In addition to the substances as described above, the hole transport region may contain a charge generation substance for improving conductivity. The charge generation substance may be uniformly or non-uniformly dispersed in the hole transport region (for example, in the form of a single layer composed of the charge generation substance). [[ID=X]]<X>
[0208] The charge generation substance may be, for example, a p-type dopant.
[0209] For example, the LUMO energy level of the p-type dopant may be -3.5 eV or less.
[0210] According to one embodiment, the p-type dopant may include a quinone derivative, a cyano group-containing compound, an element EL1-containing compound, and an element EL2-containing compound, or any combination thereof.
[0211] Examples of quinone derivatives may include TCNQ, F4-TCNQ, and the like.
[0212] Examples of the cyano group-containing compound may include HAT-CN, a compound represented by the following chemical formula 221, and the like. [ka] [ka] ...(chemical formula 221)
[0213] In chemical formula 221, R 221 ~R 223 are, independently of each other, at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 is a heterocyclic group, R 221 ~R 223 At least one of the groups, independently of one another, is a cyano group, -F, -Cl, -Br, -I, a C-C substituted with a cyano group, -F, -Cl, -Br, -I, or any combination thereof. 20 C3-C substituted with alkyl groups, or any combination thereof 60 Carbocyclic group or C1-C 60 It is a heterocyclic group.
[0214] In the element EL1-containing compound and the element EL2-containing compound, the element EL1 is a metal, a metalloid, or a combination thereof, and the element EL2 is a nonmetal, a metalloid, or a combination thereof.
[0215] Examples of the metal include alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.), alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.), transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Cs), and the like. (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.), post-transition metals (e.g., zinc (Zn), indium (In), tin (Sn), etc.), lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), ruthenium (Lu), etc.), etc.).
[0216] The metalloid may include, for example, silicon (Si), antimony (Sb), tellurium (Te), and the like.
[0217] The non-metals may include, for example, oxygen (O), halogens (eg, F, Cl, Br, I, etc.), and the like.
[0218] For example, the element EL1-containing compound and the element EL2-containing compound may include a metal oxide, a metal halide (e.g., a metal fluoride, a metal chloride, a metal bromide, a metal iodide, etc.), a metalloid halide (e.g., a metalloid fluoride, a metalloid chloride, a metalloid bromide, a metalloid iodide, etc.), a metal telluride, or any combination thereof.
[0219] Metal oxides may include, for example, tungsten oxides (e.g., WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxides (e.g., VO, VO2, VO2O5, etc.), molybdenum oxides (MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), rhenium oxides (e.g., ReO3, etc.), etc.
[0220] Metal halides may include, for example, alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, lanthanide metal halides, and the like.
[0221] Alkali metal halides may include, for example, LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, and the like.
[0222] Alkaline earth metal halides may include, for example, BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, BaI2, and the like.
[0223] Examples of the transition metal halides include titanium halides (e.g., TiF4, TiCl4, TiBr4, TiI4, etc.), zirconium halides (e.g., ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), hafnium halides (e.g., HfF4, HfCl4, HfBr4, HfI4, etc.), vanadium halides (e.g., VF3, VCl3, VBr3, VI3, etc.), niobium halides (e.g., NbF3, NbCl3, NbBr3, NbI3, etc.), tantalum halides (e.g., TaF3, TaCl3, TaBr3, TaI3, etc.), chromium halides (e.g., CrF3, CrCl3, CrBr3, CrI3, etc.), molybdenum halides (e.g., MoF3, MoCl3, MoBr3, MoI3, etc.), tungsten halides (e.g., WF3, WCl3, WBr3, WI3, etc.), manganese halides (e.g., MnF2, MnCl2, MnBr2, MnI2, etc.), technetium halides (e.g., TcF2, TcCl2, TcBr2, TcI2, etc.), rhenium halides (e.g., ReF2, ReCl2, ReBr2, ReI2, etc.), iron halides (e.g., FeF2, FeCl2, FeBr2, FeI2, etc.), ruthenium halides (e.g., RuF2, RuCl2, RuBr2, RuI2, etc.), osmium halides (e.g., OsF2, OsCl2, OsBr2, OsI2, etc.), cobalt halides (e.g., CoF2, CoCl2, CoBr2, CoI2, etc.), rhodium halides (e.g., RhF2, RhCl2, RhBr2, RhI2, etc.), iridium halides (e.g., IrF2, IrCl2, IrBr2, IrI2, etc.), nickel halides (e.g., NiF2, NiCl2, NiBr2, NiI2, etc.), palladium halides (e.g., PdF2, PdCl2, PdBr2, PdI2, etc.), platinum halides (e.g., PtF2, PtCl2, PtBr2, PtI2, etc.), copper halides (e.g., CuF, CuCl, CuBr, CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.), gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.), and the like.
[0224] Post-transition metal halides may include, for example, zinc halides (eg, ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), tin halides (eg, SnI2, etc.), and the like.
[0225] Lanthanide metal halides may include, for example, YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3SmCl3, YbBr, YbBr2, YbBr3SmBr3, YbI, YbI2, YbI3, SmI3, and the like.
[0226] Metalloid halides may include, for example, antimony halides (e.g., SbCl5, etc.).
[0227] Examples of metal tellurides include alkali metal tellurides (e.g., Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g., TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe , RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, CuTe, CuTe, AgTe, AgTe, AuTe, etc.), post-transition metal tellurides (e.g., ZnTe, etc.), lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.), and the like.
[0228] <Light-emitting layer in intermediate layer 130> When the light emitting device 10 is a full-color light emitting device, the light emitting layer may be patterned into a red light emitting layer, a green light emitting layer, and / or a blue light emitting layer for each individual subpixel. Alternatively, the light emitting layer may have a structure in which two or more layers selected from the red light emitting layer, the green light emitting layer, and the blue light emitting layer are stacked in contact with or spaced apart from each other, or a structure in which two or more materials selected from the red light emitting material, the green light emitting material, and the blue light emitting material are mixed without layer division, thereby emitting white light.
[0229] According to one embodiment, the light-emitting layer may include a host and a dopant (or an emitter). In addition to the host and the dopant (or the emitter), the light-emitting layer may further include an auxiliary dopant that promotes energy transfer to the dopant (or the emitter). When the light-emitting layer includes the dopant (or the emitter) and the auxiliary dopant, the dopant (or the emitter) and the auxiliary dopant are different from each other.
[0230] In this specification, the first compound can act as a dopant (or emitter) or as an auxiliary dopant.
[0231] The content of the dopant (or emitter) in the light-emitting layer may be about 0.01 to about 15 parts by weight based on 100 parts by weight of the host.
[0232] The thickness of the light-emitting layer may be about 10 nm to about 100 nm, for example, about 20 nm to about 60 nm. When the thickness of the light-emitting layer satisfies the above-mentioned range, excellent light-emitting properties can be exhibited without a substantial increase in driving voltage.
[0233] <host> The host in the light-emitting layer can include a second compound, a third compound, or any combination thereof described herein.
[0234] The host may also include a compound represented by the following chemical formula 301: [Ar 301 ] xb11-[(L 301 ) xb1 -R 301 ] xb21 ...(chemical formula 301)
[0235] In chemical formula 301, Ar 301 and L 301 are, independently of each other, at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 is a heterocyclic group, xb11 is 1, 2, or 3, xb1 is an integer between 0 and 5, R 301 is hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, or at least one R 10a Substituted or unsubstituted C1-C 60 alkyl group, at least one R 10a Substituted or unsubstituted C2-C 60 alkenyl group, at least one R 10a Substituted or unsubstituted C2-C 60 an alkynyl group, at least one R 10a Substituted or unsubstituted C1-C 60 an alkoxy group, at least one R 10a Substituted or unsubstituted C3-C 60 Carbocyclic group, at least one R10a Substituted or unsubstituted C1-C 60 Heterocyclic group, -Si(Q 301 )(Q 302 )(Q 303 ), -N(Q 301 )(Q 302 ), -B(Q 301 )(Q 302 ), -C(=O)(Q 301 ), -S(=O)2(Q 301 ) or -P(=O)(Q 301 )(Q 302 ) and xb21 is an integer between 1 and 5, Q 301 ~Q 303 For the explanations regarding Q1, please refer to the explanations regarding Q2 in this specification.
[0236] For example, in chemical formula 301, when xb11 is 2 or more, 2 or more Ar 301 may be bonded to each other via a single bond.
[0237] As another example, the host may include a compound represented by the following formula 301-1, a compound represented by the following formula 301-2, or any combination thereof. [ka] ...(chemical formula 301-1) [ka] ...(chemical formula 301-2)
[0238] In Chemical Formula 301-1 to Chemical Formula 301-2, Ring A 301 ~Ring A 304 are, independently of each other, at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 is a heterocyclic group, X 301 is O, S, N-[(L 304 ) xb4 -R 304 ], C(R 304 )(R 305 ) or Si(R 304 )(R 305 ) and xb22 and xb23 are independently 0, 1 or 2; L 301 , xb1 and R 301 For the explanation of each of the above, please refer to the descriptions in this specification. L 302 ~L 304 The explanations for L 301 Please refer to the explanation regarding The explanations for xb2 to xb4 are independent of each other and refer to the explanation for xb1. R 302 ~R 305 , and R 311 ~R 314 The explanations related to 301 Please refer to the explanation related to this.
[0239] As yet another example, the host may include an alkaline earth metal complex, such as a Be complex (e.g., compound H55 below), a Mg complex, a Zn complex, or any combination thereof.
[0240] As yet another example, the host may include one of Compounds H1 to H124 below, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthylene-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), or any combination thereof. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0241] Alternatively, the host may comprise a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof.
[0242] The host may include only one type of compound or two or more different compounds, and various variations are possible.
[0243] <Phosphorescent dopant> The light-emitting layer may include a first compound as described herein as a phosphorescent dopant.
[0244] Alternatively, when the light-emitting layer includes a first compound as described herein, and the first compound acts as a helping dopant, the light-emitting layer can include a phosphorescent dopant.
[0245] The phosphorescent dopant may include at least one transition metal as the central metal.
[0246] The phosphorescent dopant may include monodentate ligands, bidentate ligands, tridentate ligands, tetradentate ligands, pentadentate ligands, hexadentate ligands, or any combination thereof.
[0247] The phosphorescent dopant may be electrically neutral.
[0248] For example, the phosphorescent dopant may include an organometallic compound represented by Formula 401: M(L 401 ) xc1 (L 402 )xc2...(Chemical formula 401) [ka] ...(chemical formula 402)
[0249] In Chemical Formula 401 and Chemical Formula 402, M is a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)); L 401 is a ligand represented by the above chemical formula 402, xc1 is 1, 2 or 3, and when xc1 is 2 or more, two or more L 401 are either identical to each other or different, L 402is an organic ligand, xc2 is 0, 1, 2, 3, or 4, and when xc2 is 2 or more, two or more L 402 are either identical to each other or different, X 401 and X 402 are, independently of each other, nitrogen or carbon, Ring A 401 and Ring A 402 are independent of each other, C3-C 60 Carbocyclic group or C1-C 60 is a heterocyclic group, T 401 is a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*', *-C(Q 411 )(Q 412 )-*', *-C(Q 411 )=C(Q 412 )-*', *-C(Q 411 )=*' or *=C=C*', X 403 and X 404 are, independently of each other, chemical bonds (e.g., covalent or coordinate bonds), O, S, N(Q 413 ), B(Q 413 ), P(Q 413 ), C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ) and Q 411 ~Q 414 For the explanation of each of the above, please refer to the explanation of Q1 in this specification. R 401 and R 402 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, at least one R 10a Substituted or unsubstituted C1-C 20 alkyl group, at least one R 10a Substituted or unsubstituted C1-C 20 an alkoxy group, at least one R 10a Substituted or unsubstituted C3-C 60Carbocyclic group, at least one R10a Substituted or unsubstituted C1-C 60 Heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 ), -N(Q 401 )(Q 402 ), -B(Q 401 )(Q 402 ), -C(=O)(Q 401 ), -S(=O)2(Q 401 ) or -P(=O)(Q 401 )(Q 402 ) and Q 401 ~Q 403 For the explanation of each of the above, please refer to the explanation of Q1 in this specification. xc11 and xc12 are each independently an integer of 0 to 10; In the chemical formula 402, * and *' represent the chemical formula 401 This is the bonding position with M in
[0250] For example, in formula 402, i) X 401 is nitrogen and X 402 may be carbon, or ii) X 401 and X 402 may both be nitrogen.
[0251] As another example, in chemical formula 402, when xc1 is 2 or more, 2 or more L 401 In this case, two rings A 401 is optionally a linking group, T 402 or two rings A 402 is optionally a linking group, T 403 (See Compounds PD1 to PD4 below, and Compound PD7 below). 402 and T 403 The explanations regarding these are given in this specification under the headings T 401 Please refer to the explanation related to this.
[0252] L in Chemical Formula 401402 can be any organic ligand. For example, L 402 may include a halogen group, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), a -C(=O), an isonitrile group, a -CN group, a phosphorous group (e.g., a phosphine group, a phosphite group, etc.), or any combination thereof.
[0253] The phosphorescent dopant may include, for example, one of the following compounds PD1 to PD25, or any combination thereof. [ka] [ka] [ka]
[0254] <Fluorescent dopant> When the light-emitting layer comprises a first compound as described herein, and the first compound acts as a helping dopant, the light-emitting layer may further comprise a fluorescent dopant.
[0255] Alternatively, when the light-emitting layer includes a first compound as described herein, and the first compound performs the role of a phosphorescent dopant, the light-emitting layer may further include a helping dopant.
[0256] The fluorescent dopant and the auxiliary dopant may, independently of one another, comprise an arylamine compound, a styrylamine compound, a boron-containing compound, or any combination thereof.
[0257] For example, the fluorescent dopant and the assisting dopant may each independently comprise a compound represented by the following formula 501: [ka] ...(chemical formula 501)
[0258] In chemical formula 501, Ar 501 , L 501 ~L 503 , R 501 and R 502 are, independently of each other, at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 is a heterocyclic group, xd1 to xd3 are independently 0, 1, 2, or 3; xd4 is 1, 2, 3, 4, 5, or 6.
[0259] For example, Ar in formula 501 501 may contain a fused ring group in which three or more monocyclic groups are fused together (for example, an anthracenyl group, a chrysenyl group, a pyrenyl group, etc.).
[0260] As another example, xd4 in chemical formula 501 may be 2.
[0261] For example, the fluorescent dopant and the assisting dopant may include one of the following compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof. [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0262] Alternatively, the fluorescent dopant and the co-dopant may each independently comprise a fourth compound represented by Formula 502 or Formula 503, as described herein.
[0263] [Electron transport region in intermediate layer 130] The electron transport region can have i) a single layer structure consisting of a single layer of a single material, ii) a single layer structure consisting of a single layer containing multiple different materials, or iii) a multilayer structure including multiple layers containing multiple different materials.
[0264] The electron transport region may include a buffer layer, a hole blocking layer (EBL), an electron modulating layer, an electron transport layer (ETL), an electron injection layer (EIL), or any combination thereof.
[0265] For example, the electron transport region may have a structure such as an electron transport layer / electron injection layer, a hole blocking layer / electron transport layer / electron injection layer, an electron modulating layer / electron transport layer / electron injection layer, or a buffer layer / electron transport layer / electron injection layer, which are stacked in this order from the light emitting layer.
[0266] The electron transport region (e.g., a buffer layer, a hole blocking layer, an electron modulating layer, or an electron transport layer in the electron transport region) is preferably a π-electron deficient nitrogen-containing C1-C 60 It may also include non-metal-containing compounds that contain cyclic groups.
[0267] For example, the electron transport region may include a compound represented by formula 601 below. [Ar 601 ] xe11-[(L 601 ) xe1 -R 601 ] xe21 ...(chemical formula 601)
[0268] In chemical formula 601, Ar 601 and L 601 are, independently of each other, at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 is a heterocyclic group, xe11 is 1, 2 or 3, xe1 is 0, 1, 2, 3, 4 or 5, R 601 is at least one R 10a Substituted or unsubstituted C3-C 60 Carbocyclic group, at least one R10a Substituted or unsubstituted C1-C 60 Heterocyclic group, -Si(Q 601 )(Q 602 )(Q 603 ), -C(=O)(Q 601 ), -S(=O)2(Q 601 ) or -P(=O)(Q 601 )(Q 602 ) and Q 601 ~Q 603 For the explanation of each of the above, please refer to the explanation of Q1 in this specification. xe21 is 1, 2, 3, 4 or 5, The aforementioned Ar 601 , L 601 and R 601 At least one of the groups, independently of each other, is selected from the group consisting of at least one R 10a Substituted or unsubstituted π-electron deficient nitrogen-containing C1-C 60 It is a cyclic group.
[0269] For example, in chemical formula 601, when xe11 is 2 or more, 2 or more Ar 601can be bonded to each other via a single bond.
[0270] As another example, Ar in formula 601 601 may be a substituted or unsubstituted anthracenyl group.
[0271] As yet another example, the electron transport region may include a compound represented by the following formula 601-1: [ka] ...(chemical formula 601-1)
[0272] In chemical formula 601-1, X 614 is N or C(R 614 ) and X 615 is N or C(R 615 ) and X 616 is N or C(R 616 ) and X 614 ~X 616 At least one of is N, L 611 ~L 613 The explanations related to 601 Please refer to the explanation regarding For explanations of xe611 to xe613, please refer to the explanations of xe1. R 611 ~R 613 The explanations related to 601 Please refer to the explanation regarding R 614 ~R 616 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C1-C 20 Alkyl groups, C1-C 20 an alkoxy group, at least one R 10a Substituted or unsubstituted C3-C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 60 It is a heterocyclic group.
[0273] For example, in chemical formula 601 and chemical formula 601-1, xe1 and xe611 to xe613 may be 0, 1, or 2, independently of each other.
[0274] The electron transport region may include one of Compounds ET1 to ET45 below, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ, NTAZ, or any combination thereof. [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0275] The thickness of the electron transport region may be about 16 nm to about 500 nm, for example, about 10 nm to about 400 nm. When the electron transport region includes a buffer layer, a hole blocking layer, an electron modulating layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron modulating layer may be, independently of one another, about 2 nm to about 100 nm, for example, about 3 nm to about 30 nm, and the thickness of the electron transport layer may be about 10 nm to about 100 nm, for example, about 15 nm to about 50 nm. When the thicknesses of the buffer layer, the hole blocking layer, the electron modulating layer, the electron transport layer, and / or the electron transport layer satisfy the above-mentioned ranges, sufficient electron transport properties can be obtained without a substantial increase in driving voltage.
[0276] The electron transport region (for example, the electron transport layer in the electron transport region) may further contain a metal-containing material in addition to the materials described above.
[0277] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and the metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. The ligands coordinated to the metal ions of the alkali metal complex and the alkaline earth metal complex may, independently of one another, include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0278] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, the following compound ET-D1(LiQ) or the following compound ET-D2. [ka]
[0279] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 150. The electron injection layer may be in direct contact with the second electrode 150.
[0280] The electron injection layer may have i) a single layer structure consisting of a single layer made of a single material, ii) a single layer structure consisting of a single layer containing a plurality of different materials, or iii) a multilayer structure having a plurality of layers containing a plurality of different materials.
[0281] The electron injection layer may comprise an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0282] The alkali metals may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metals may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metals may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0283] The alkali metal-containing compound, alkaline earth metal-containing compound, and rare earth metal-containing compound may include oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), tellurides, or any combination thereof, of the alkali metals, alkaline earth metals, and rare earth metals, respectively.
[0284] The alkali metal-containing compound may include an alkali metal oxide such as Li2O, Cs2O, or K2O, an alkali metal halide such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI, or any combination thereof. The alkaline earth metal-containing compound may include BaO, SrO, CaO, Ba x Sr1-x O (where x is a real number satisfying 0 < x < 1), Ba x Ca 1-x It may contain an alkaline earth metal compound such as O (where x is a real number satisfying 0 < x < 1). The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. Further, the rare earth metal-containing compound may include a lanthanoid metal telluride. Examples of the lanthanoid metal telluride may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, Lu2Te3, etc.
[0285] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex include i) one of the ions of the alkali metal, alkaline earth metal, and rare earth metal as described above, and ii) as a ligand that binds to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0286] The electron injection layer may be composed only of the alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkaline earth metal-containing compound, rare earth metal-containing compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof as described above, and may further contain an organic substance (for example, the compound represented by Chemical Formula 601).
[0287] According to one embodiment, the electron injection layer may be i) composed of an alkali metal-containing compound (e.g., an alkali metal halide), or ii) composed of (a) an alkali metal-containing compound (e.g., an alkali metal halide) and (b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI:Yb co-deposited layer, a RbI:Yb co-deposited layer, etc.
[0288] When the electron injection layer further contains an organic substance, the alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkaline earth metal-containing compound, rare earth metal-containing compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof is uniformly or non-uniformly dispersed in a matrix containing the organic substance.
[0289] The thickness of the electron injection layer may be about 0.1 nm to about 10 nm, or about 0.3 nm to about 9 nm. When the thickness of the electron injection layer satisfies the above-mentioned range, sufficient electron injection characteristics can be obtained without a substantial increase in driving voltage.
[0290] <Second electrode 150> The second electrode 150 is disposed on the intermediate layer 130. The second electrode 150 is a cathode, which is an electron injection electrode. In this case, the material for the second electrode 150 may be a metal, alloy, electrically conductive compound, or any combination thereof, which has a low work function.
[0291] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0292] The second electrode 150 may have a single layer structure, which is a single layer, or a multi-layer structure having multiple layers.
[0293] <Capping layer> A first capping layer may be disposed on the outer side of the first electrode 110, and / or a second capping layer may be disposed on the outer side of the second electrode 150. Specifically, the light emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the intermediate layer 130, and the second electrode 150 are stacked in this order, a structure in which the first electrode 110, the intermediate layer 130, the second electrode 150, and the second capping layer are stacked in this order, or a structure in which the first capping layer, the first electrode 110, the intermediate layer 130, the second electrode 150, and the second capping layer are stacked in this order.
[0294] In the intermediate layer 130 of the light-emitting element 10, light generated from the light-emitting layer may be extracted to the outside through the first electrode 110, which is a semi-transparent electrode or a transparent electrode, and the first capping layer, and in the intermediate layer 130 of the light-emitting element 10, light generated from the light-emitting layer may be extracted to the outside through the second electrode 150, which is a semi-transparent electrode or a transparent electrode, and the second capping layer.
[0295] The first and second capping layers can improve the external light emitting efficiency due to the principle of constructive interference, thereby increasing the light extraction efficiency of the light emitting device 10 and improving the light emitting efficiency of the light emitting device 10.
[0296] Each of the first and second capping layers may include a material having a refractive index (@589 nm) of 1.6 or greater.
[0297] The first capping layer and the second capping layer may be, independently of each other, an organic capping layer containing an organic material, an inorganic capping layer containing an inorganic material, or a composite capping layer containing an organic material and an inorganic material.
[0298] At least one of the first capping layer and the second capping layer may, independently of one another, comprise a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may optionally be substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. According to one embodiment, at least one of the first capping layer and the second capping layer may, independently of one another, comprise an amino group-containing compound.
[0299] For example, at least one of the first capping layer and the second capping layer may, independently of one another, include the compound represented by the aforementioned formula 201, the compound represented by the formula 202, or any combination thereof.
[0300] According to another embodiment, at least one of the first capping layer and the second capping layer may independently contain one of the aforementioned compounds HT28 to HT33, one of the following compounds CP1 to CP6, β-NPB, or any of these compounds. [ka] [ka]
[0301] [Electronic equipment] The light-emitting element is included in various electronic devices, such as a light-emitting device, an authentication device, and the like.
[0302] An electronic device (e.g., a light-emitting device) may further include, in addition to a light-emitting element, i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and / or the color conversion layer are disposed in at least one traveling direction of light emitted from the light-emitting element. For example, the light emitted from the light-emitting element is blue light or white light. See above for a description of the light-emitting element. According to one embodiment, the color conversion layer may include quantum dots.
[0303] The electronic device may include a first substrate, the first substrate including a plurality of sub-pixel regions, the color filter including a plurality of color filter regions corresponding to the plurality of sub-pixel regions, and the color conversion layer including a plurality of color conversion regions corresponding to the plurality of sub-pixel regions.
[0304] A pixel defining film is disposed between the plurality of sub-pixel regions to define each of the sub-pixel regions.
[0305] The color filter may further include a plurality of color filter regions and a light-shielding pattern arranged between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light-shielding pattern arranged between the plurality of color conversion regions.
[0306] The color filter regions (or color conversion regions) may include a first region emitting a first color light, a second region emitting a second color light, and / or a third region emitting a third color light, where the first color light, the second color light, and / or the third color light may have different maximum emission wavelengths. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, the color filter regions (or color conversion regions) may include quantum dots. For example, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include quantum dots. For details regarding quantum dots, please refer to the description herein. The first region, the second region, and / or the third region may each further include a scatterer.
[0307] For example, the light-emitting element may emit a first light, the first region may absorb the first light and emit a first-1 color light, the second region may absorb the first light and emit a second-1 color light, and the third region may absorb the first light and emit a third-1 color light. In this case, the first-1 color light, the second-1 color light, and the third-1 color light may have different maximum emission wavelengths. Specifically, the first light may be blue light, the first-1 color light may be red light, the second-1 color light may be green light, and the third-1 color light may be blue light.
[0308] The electronic device may further include a thin film transistor (TFT) in addition to the light emitting element described above. The TFT may include a source electrode, a drain electrode, and an active layer, and one of the source electrode and the drain electrode may be electrically connected to one of the first electrode and the second electrode of the light emitting element.
[0309] The thin film transistor may further include a gate electrode, a gate insulating film, and the like.
[0310] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, or the like.
[0311] The electronic device may further include a sealing part that seals the light-emitting element. The sealing part may be disposed between the color filter and / or color conversion layer and the light-emitting element. The sealing part allows light from the light-emitting element to be extracted to the outside while simultaneously preventing external air and moisture from penetrating into the light-emitting element. The sealing part may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing part may be a thin-film sealing layer including one or more organic and / or inorganic layers. When the sealing part is a thin-film sealing layer, the electronic device may be flexible.
[0312] In addition to the color filter and / or color conversion layer, various functional layers may be additionally disposed on the sealing portion depending on the application of the electronic device. The functional layer may include, for example, a touchscreen layer, a polarizing layer, etc. The touchscreen layer may be a decompression touchscreen layer, an electrostatic touchscreen layer, or an infrared touchscreen layer. The authentication device may be, for example, a biometric authentication device that authenticates an individual using biometric information (e.g., fingertip, pupil, etc.).
[0313] The authentication device may further include a biometric information collecting means in addition to the light-emitting element as described above.
[0314] Electronic devices are also used in various displays, light sources, lighting, personal computers (PCs) (e.g., mobile PCs), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game consoles, medical equipment (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram display devices, ultrasound diagnostic devices, and endoscopic display devices), fish finders, various measuring instruments, gauges (e.g., gauges for vehicles, aircraft, and ships), projectors, and the like.
[0315] Description of Figures 2 and 3 FIG. 2 is a cross-sectional view of a light emitting device according to one embodiment of the present invention.
[0316] The light emitting device of FIG. 2 includes a substrate 100, a thin film transistor (TFT), a light emitting element, and an encapsulation part 300 that seals the light emitting element.
[0317] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be disposed on the substrate 100. The buffer layer 210 may prevent impurities from penetrating through the substrate 100 and may provide a flat surface on the top of the substrate 100.
[0318] A thin film transistor (TFT) may be disposed on the buffer layer 210. The thin film transistor (TFT) may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
[0319] The active layer 220 includes an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and includes a source region, a drain region, and a channel region.
[0320] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be disposed on the active layer 220 , and the gate electrode 240 may be disposed on the gate insulating film 230 .
[0321] An interlayer insulating film 250 may be disposed on the gate electrode 240. The interlayer insulating film 250 is disposed between the gate electrode 240 and the source electrode 260, and between the gate electrode 240 and the drain electrode 270, to insulate them.
[0322] A source electrode 260 and a drain electrode 270 may be disposed on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may be disposed to contact the exposed source region and the drain region of the active layer 220.
[0323] Such a thin film transistor (TFT) is electrically connected to the light emitting element to drive the light emitting element, and is covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. The light emitting element is provided on the passivation layer 280. The light emitting element includes a first electrode 110, an intermediate layer 130, and a second electrode 150.
[0324] The first electrode 110 is also disposed on the passivation layer 280. The passivation layer 280 may be disposed so as to expose a predetermined region without covering the entire drain electrode 270, and the first electrode 110 may be disposed so as to be connected to the exposed drain electrode 270.
[0325] A pixel defining layer 290 including an insulating material may be disposed on the first electrode 110. The pixel defining layer 290 exposes a predetermined region of the first electrode 110, and the intermediate layer 130 may be formed in the exposed region. The pixel defining layer 290 may be a polyimide-based or polyacrylic-based organic film. Although not shown in FIG. 2 , some or more layers of the intermediate layer 130 may extend onto the pixel defining layer 290 and be disposed in the form of a common layer.
[0326] The second electrode 150 may be disposed on the intermediate layer 130, and a capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
[0327] The encapsulation part 300 may be disposed on the capping layer 170. The encapsulation part 300 is disposed on the light emitting device and can protect the light emitting device from moisture and oxygen. The encapsulation part 300 is made of silicon nitride (SiN x ), silicon oxide (SiO x ), indium tin oxide, indium zinc oxide, or an inorganic film containing any combination thereof; polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), an epoxy resin (e.g., AGE (aliphatic glycidyl ether), etc.), or an organic film containing any combination thereof; or a combination of an inorganic film and an organic film.
[0328] FIG. 3 is a cross-sectional view of a light emitting device according to another embodiment of the present invention.
[0329] The light emitting device of Figure 3 is the same as the light emitting device of Figure 2, except that a light-blocking pattern 500 and a functional region 400 are additionally disposed on top of the encapsulation unit 300. The functional region 400 may be i) a color filter region, ii) a color conversion region, or iii) a combination of a color filter region and a color conversion region. According to one embodiment, the light emitting element included in the light emitting device of Figure 3 is a tandem light emitting element.
[0330] [Manufacturing method] Each layer included in the hole transport region, the light emitting layer, and the electron transport region can be formed in a predetermined region using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, ink jet printing, laser printing, and laser induced thermal imaging (LITI) method.
[0331] When each layer included in the hole transport region, the light emitting layer, and each layer included in the electron transport region are formed by the vacuum deposition method, the deposition conditions are, for example, a deposition temperature of about 100 to about 500° C., a deposition temperature of about 10 -8 ~about 10 -3 The degree of vacuum of torr and the deposition rate range of about 0.01 to about 100 Å / sec are selected in consideration of the material contained in the layer to be formed and the structure of the layer to be formed. [Example]
[0332] The compound and light-emitting device according to one embodiment of the present invention will be described in more detail below with reference to synthesis examples and examples. In the synthesis examples below, when the expression "B was used instead of A" is used, the molar equivalents of A and B are the same.
[0333] Synthesis Example 1 (Synthesis of Compound D6) [ka]
[0334] (Synthesis of Intermediate D6-1) 25.0 g (70.8 mmol) of 9-(4-bromopyridin-2-yl)-2-methoxy-9H-carbazole was mixed with 700 mL of tetrahydrofuran. The reaction temperature was lowered to -78 °C, and 39 mL of N-BuLi solution (2.0 M in hexane) was added. The mixture was stirred at the same temperature for 1 hour. 21.3 g (141.6 mmol) of 2-adamantanone was then added, and the reaction temperature was raised to room temperature and stirred for 24 hours. After the reaction was completed, NaHCO3 solution was added, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with saturated aqueous NaCl and dried over sodium sulfate. The resulting product was purified by column chromatography to obtain 22.3 g (52.5 mmol) of intermediate D6-1.
[0335] (Synthesis of intermediate D6-2) 22.3 g (52.5 mmol) of the obtained intermediate D6-1 and 21.0 g (157.5 mmol) of AlCl3 were stirred with an excess amount of benzene under nitrogen at room temperature for 24 hours. After the reaction was completed, NaHCO3 solution was added to neutralize the mixture, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with saturated aqueous sodium chloride solution and then dried over sodium sulfate. The resulting product was purified by column chromatography to obtain 20.0 g (41.2 mmol) of intermediate D6-2.
[0336] (Synthesis of intermediate D6-3) 20.2 g (41.7 mmol) of the obtained intermediate D6-2 was suspended in an excess amount of HBr solution, heated, and stirred at 110°C for 24 hours. After the reaction was completed, the mixture was cooled to room temperature and neutralized with an appropriate amount of NaHCO3. 300 mL of distilled water was added, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with saturated aqueous sodium chloride solution and dried over MgSO4. The obtained product was purified by column chromatography to obtain 18.9 g (39.5 mmol) of intermediate D6-3.
[0337] (Synthesis of intermediate D6-4) The resulting intermediate D6-3 (15.4 g, 32.7 mmol), 1,3-dibromobenzene (8.2 g, 34.6 mmol), KPO (13.9 g, 65.4 mmol, 2.0 equivalents), CuI (0.6 g, 3.3 mmol, 0.1 equivalents), and di([1,1'-biphenyl]-2-yl)oxamide (1.3 g, 3.3 mmol) were placed in a reaction vessel and suspended in 80 mL of dimethyl sulfoxide. The mixture was then heated and stirred at 160°C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, 300 mL of distilled water was added, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with saturated aqueous sodium chloride and dried over sodium sulfate. The resulting product was purified by column chromatography to yield 16.5 g (26.3 mmol) of intermediate D6-4.
[0338] (Synthesis of Intermediate D6-5) The obtained intermediate D6-4 was 23.8 g (38.1 mmol), N'-([1,1':3',1"-terphenyl]-2'-yl-2,2",3,3",4,4",5,5",6,6"-d 10 15.8 g (45.7 mmol) of benzene-1,2-diamine, 0.4 g (0.76 mmol, 0.02 equiv.) of Pd2(dba), 0.6 g (1.52 mmol, 0.04 equiv.) of SPhos, and 4.8 g (49.5 mmol, 1.6 equiv.) of NaOtBu were placed in a reaction vessel and suspended in 100 mL of toluene (0.1 M). The mixture was heated and stirred at 120 °C for 4 hours. After the reaction was completed, the mixture was cooled to room temperature, 300 mL of distilled water was added, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with saturated aqueous sodium chloride and dried over sodium sulfate. The resulting product was purified by column chromatography to yield 23.6 g (26.5 mmol) of intermediate D6-5.
[0339] (Synthesis of Intermediate D6-6) 23.2 g (26.0 mmol) of the obtained intermediate D6-5, 216 mL (1.3 mol, 50.0 equivalents) of triethyl orthoformate, and 0.9 mL (31.2 mmol, 1.2 equivalents) of HCl (37%) were placed in a reaction vessel, heated, and stirred at 80° C. for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and the resulting solid was filtered and washed with ether. The washed solid was then dried to obtain 22.5 g (23.4 mmol) of intermediate D6-6.
[0340] (Synthesis of Intermediate D6-7) The resulting intermediate D6-6 (21.1 g, 22.5 mmol) and NH4PF6 (11.0 g, 67.5 mmol, 3.0 equivalents) were placed in a reaction vessel and suspended in a mixture of 100 mL of methyl alcohol and 50 mL of water (2:1 volume ratio), followed by stirring at room temperature for 24 hours. After the reaction was completed, the resulting solid was filtered and washed with ether. The washed solid was then dried to obtain 26.0 g (16.8 mmol) of intermediate D6-7.
[0341] (Synthesis of Compound D6) The resulting intermediate D6-7 (16.5 g, 15.8 mmol), dichloro(1,5-cyclooctadiene)platinum (6.2 g, 16.7 mmol, 1.1 equivalents), and NaOAc (3.9 g, 47.4 mmol, 3.0 equivalents) were suspended in 300 mL of 1,4-dioxane (0.025 M) and heated to 110°C with stirring for 72 hours. After the reaction was completed, the mixture was cooled to room temperature, 250 mL of distilled water was added, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with aqueous NaCl and dried over MgSO4. The resulting product was purified by column chromatography to yield 5.5 g (5.1 mmol) of compound D6.
[0342] Synthesis Example 2 (Synthesis of Compound D12) [ka]
[0343] (Synthesis of intermediate D12-2) 22.3 g (52.5 mmol) of the above intermediate D6-1, 21.0 g (157.5 mmol) of AlCl3, and 4a,8a-azaboranaphthalene (1.0 equivalent) were stirred with excess dichloromethane at 40°C for 24 hours under nitrogen. After the reaction was completed, NaHCO3 solution was added to neutralize the mixture, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with saturated aqueous sodium chloride and then dried over sodium sulfate. The resulting product was purified by column chromatography to obtain intermediate D12-2.
[0344] (Synthesis of intermediate D12-3) Intermediate D12-3 was obtained using the same method as for synthesizing intermediate D6-3 in Synthesis Example 1 above, except that intermediate D12-2 was used instead of intermediate D6-2.
[0345] (Synthesis of intermediate D12-4) Intermediate D12-4 was obtained using the same method as that for synthesizing intermediate D6-4 in Synthesis Example 1 above, except that intermediate D12-3 was used instead of intermediate D6-3.
[0346] (Synthesis of intermediate D12-5) Intermediate D12-5 was obtained using the same method as that for synthesizing intermediate D6-5 in Synthesis Example 1 above, except that intermediate D12-4 was used instead of intermediate D6-4.
[0347] (Synthesis of intermediate D12-6) Intermediate D12-6 was obtained using the same method as that for synthesizing intermediate D6-6 in Synthesis Example 1 above, except that intermediate D12-5 was used instead of intermediate D6-5.
[0348] (Synthesis of intermediate D12-7) Intermediate D12-7 was obtained using the same method as that for synthesizing Intermediate D6-7 in Synthesis Example 1 above, except that Intermediate D12-6 was used instead of Intermediate D6-6.
[0349] (Synthesis of Compound D12) The same method as used to synthesize compound D6 in Synthesis Example 1 above was used, except that intermediate D12-7 was used instead of intermediate D6-7, to obtain 5.60 g (4.90 mmol) of compound D12.
[0350] Synthesis Example 3 (Synthesis of Compound D27) [ka]
[0351] (Synthesis of intermediate D27-4) Intermediate D27-4 was synthesized using the same method as that for intermediate D12-4 in Synthesis Example 2 above, except that 1,3-dibromo-5-(tert-butyl)benzene was used instead of 1,3-dibromobenzene.
[0352] (Synthesis of intermediate D27-5) Intermediate D27-5 was obtained using the same method as that for synthesizing intermediate D12-5 in Synthesis Example 2 above, except that intermediate D27-4 was used instead of intermediate D12-4.
[0353] (Synthesis of intermediate D27-6) Intermediate D27-6 was obtained using the same method as that for synthesizing intermediate D12-6 in Synthesis Example 2 above, except that intermediate D27-5 was used instead of intermediate D12-5.
[0354] (Synthesis of intermediate D27-7) Intermediate D27-7 was obtained using the same method as that for synthesizing intermediate D12-7 in Synthesis Example 2 above, except that intermediate D27-6 was used instead of intermediate D12-6.
[0355] (Synthesis of Compound D27) The same method as used to synthesize compound D12 in Synthesis Example 2 above was used, except that intermediate D27-7 was used instead of intermediate D12-7, to obtain 5.88 g (4.90 mmol) of compound D27.
[0356] Synthesis Example 4 (Synthesis of Compound D81) [ka]
[0357] (Synthesis of intermediate D81-4) Intermediate D81-4 was synthesized using the same method as that for intermediate D6-4 in Synthesis Example 1 above, except that (3,5-dibromophenyl)methanetriyl)tribenzene was used instead of 1,3-dibromobenzene.
[0358] (Synthesis of intermediate D81-5) Intermediate D81-5 was obtained using the same method as that for synthesizing Intermediate D6-5 in Synthesis Example 1 above, except that Intermediate D81-4 was used instead of Intermediate D6-4.
[0359] Synthesis of intermediate D81-6 Intermediate D81-6 was obtained using the same method as that for synthesizing intermediate D6-6 in Synthesis Example 1 above, except that intermediate D81-5 was used instead of intermediate D6-5.
[0360] Synthesis of intermediate D81-7 Intermediate D81-7 was obtained using the same method as for synthesizing intermediate D6-7 in Synthesis Example 1 above, except that intermediate D81-6 was used instead of intermediate D6-6.
[0361] (Synthesis of Compound D81) The same method as used to synthesize compound D6 in Synthesis Example 1 above was used, except that intermediate D81-7 was used instead of intermediate D6-7, to obtain 5.22 g (3.95 mmol) of compound D81.
[0362] Synthesis Example 5 (Synthesis of Compound D302) [ka]
[0363] (Synthesis of Intermediate D302-1) Intermediate D302-1 was synthesized using the same method as that for intermediate D6-1 in Synthesis Example 1 above, except that acetone-d6 was used instead of 2-adamantanone.
[0364] (Synthesis of intermediate D302-2) Intermediate D302-2 was obtained using the same method as for synthesizing intermediate D6-2 in Synthesis Example 1 above, except that intermediate D302-1 was used instead of intermediate D6-1.
[0365] (Synthesis of intermediate D302-3) Intermediate D302-3 was obtained using the same method as for synthesizing intermediate D6-3 in Synthesis Example 1 above, except that intermediate D302-2 was used instead of intermediate D6-2.
[0366] (Synthesis of intermediate D302-4) Intermediate D302-4 was obtained using the same method as for synthesizing intermediate D6-4 in Synthesis Example 1 above, except that intermediate D302-3 was used instead of intermediate D6-3.
[0367] (Synthesis of intermediate D302-5) Intermediate D302-5 was obtained using the same method as for synthesizing Intermediate D6-5 in Synthesis Example 1 above, except that Intermediate D302-4 was used instead of Intermediate D6-4.
[0368] (Synthesis of intermediate D302-6) Intermediate D302-6 was obtained using the same method as for synthesizing Intermediate D6-6 in Synthesis Example 1 above, except that Intermediate D302-5 was used instead of Intermediate D6-5.
[0369] (Synthesis of intermediate D302-7) Intermediate D302-7 was obtained using the same method as for synthesizing Intermediate D6-7 in Synthesis Example 1 above, except that Intermediate D302-6 was used instead of Intermediate D6-6.
[0370] (Synthesis of Compound D302) The same method as used to synthesize compound D6 in Synthesis Example 1 above was used, except that intermediate D302-7 was used instead of intermediate D6-7, to obtain 5.73 g (5.69 mmol) of compound D302.
[0371] Compounds synthesized in Synthesis Examples 1 to 5 1 The H NMR and MALDI-TOF MS results are shown in Table 1 below. Methods for synthesizing compounds other than those synthesized in Synthesis Examples 1 to 5 will be readily apparent to those skilled in the art with reference to the above synthesis routes and raw materials. [Table 1]
[0372] Evaluation example 1 The HOMO energy level and LUMO energy level of each of compounds D6, D12, D27, D81 and D302 were evaluated by the method shown in Table 2 below, and the results are shown in Table 3. [Table 2] [Table 3] [ka]
[0373] Evaluation example 2 Compounds ETH66, HTH29, and D6 were applied to a quartz substrate at 10-7 torrA 40 nm thick film 1 was produced by vacuum co-evaporation at a vacuum degree of 1000 MPa. The contents of compounds ETH66, HTH29, and D6 were adjusted so that the weight ratio of compound ETH66 to compound HTH29 was 3:7 and the content of compound D6 was 10 parts by weight per 100 parts by weight of the film. Next, films 2 to 5 were produced by the same method as film 1, except that compounds D12, D27, D81, and D302 were used, respectively, instead of compound D6.
[0374] The emission spectra of each of Films 1 to 5 were measured using a Quantaurus-QY Absolute PL quantum yield spectrometer (Hamamatsu Photonics, Shizuoka) equipped with a xenon light source, a monochromator, a photonic multichannel analyzer, and an integrating sphere, and running PLQY measurement software. The excitation wavelength was scanned from 320 nm to 380 nm at 10 nm intervals, and the spectrum measured at an excitation wavelength of 340 nm was selected. The maximum emission wavelength of the dopant contained in each film was determined from the spectrum, and the results are summarized in Table 4 below.
[0375] Next, the luminescence quantum efficiency of each of films 1 to 5 was measured using a Quantaurus-QY Absolute PL quantum yield spectrometer (Hamamatsu Photonics K.K., Shizuoka) by scanning the excitation wavelength from 320 nm to 380 nm at 10 nm intervals. The luminescence quantum efficiency measured at an excitation wavelength of 340 nm was then taken, and the luminescence quantum efficiency of the dopant contained in each film was calculated from this, and is summarized in Table 4. [Table 4] [ka]
[0376] It can be seen from Table 4 that Compounds D6, D12, D27, D81 and D302 emit blue light with excellent PLQY.
[0377] Evaluation example 3 For each of films 1 to 5, a PicoQuant FluoTime 300 TRPL measurement meter and a PicoQuant PLS340 pumping source (excitation wavelength = 340 nm, spectral width = 20 nm) were used to measure the PL spectrum at room temperature. The wavelength of the main peak of the spectrum was then determined, and the number of photons emitted from each film at the main peak wavelength was measured over time using time-correlated single photon counting (TCSPC) by applying a photon pulse (pulse width = 500 picoseconds) to each film using the PLS340. A TRPL curve that was sufficiently fittable was then obtained. An exponential decay function greater than or equal to 1 was fitted to the results obtained, and the T for each of films 1 to 5 was calculated. decay The decay time (Ex), i.e., the decay time, was calculated and the results are summarized in Table 5. The function used for fitting is shown in Equation 1 below, and the T obtained from each exponential decay function used for fitting is decay The maximum value of T decay At this time, the same measurement was repeated once more under dark conditions (a state in which the pumping signal incident on the specified film was blocked) for the same measurement time as that for determining the TRPL curve, to obtain a baseline or background signal curve, which was used as the baseline for fitting.
number
[0378] It can be seen from Table 5 that Compounds D6, D12, D27, D81 and D302 have excellent decay times.
[0379] Example 1 As an anode, 15 Ω / cm 2 A glass substrate (manufactured by Corning) on which ITO (120 nm) was formed was cut into a size of 50 mm × 50 mm × 0.7 mm, and ultrasonically cleaned using isopropyl alcohol and pure water for 5 minutes each, then irradiated with ultraviolet light for 30 minutes, and exposed to ozone for cleaning, and then placed in a vacuum deposition apparatus.
[0380] 2-TNATA was vacuum-deposited on the anode to form a 60-nm-thick hole-injection layer, and 4,4'-bis[N-(1-naphthyl)-N-phenylaminobiphenyl (NPB)] was vacuum-deposited on the hole-injection layer to form a 30-nm-thick hole-transport layer.
[0381] A 40 nm-thick light-emitting layer was formed on the hole-transporting layer by vacuum deposition of Compound D6 (first compound), Compound ETH66 (second compound), and Compound HTH29 (third compound). The content of Compound D6 was 10 wt% based on the total weight (100 wt%) of the light-emitting layer, and the weight ratio of Compound ETH66 to Compound HTH29 was adjusted to 3:7.
[0382] An organic light-emitting element was fabricated by vacuum-depositing the compound ETH2 on the light-emitting layer to form a 5-nm-thick hole-blocking layer, vacuum-depositing Alq3 on the hole-blocking layer to form a 30-nm-thick electron-transporting layer, vacuum-depositing LiF on the electron-transporting layer to form a 1-nm-thick electron-injecting layer, and vacuum-depositing Al to form a 300-nm-thick cathode. [ka]
[0383] Examples 2 to 6 An organic light-emitting device was fabricated in the same manner as in Example 1, except that the compounds listed in Table 6 were used as the first compound, the second compound, and the third compound in forming the light-emitting layer.
[0384] Evaluation example 4 1,000 cd / m of the organic light-emitting devices fabricated in Examples 1 to 6 2 Driving voltage (V), color purity (CIEx,y), luminous efficiency (cd / A), color conversion efficiency (cd / A / y), maximum emission wavelength (nm) and lifetime (T 95 ) were measured using a Keithley MU 236 and a luminance meter PR650, respectively, and the results are shown in Tables 6 and 7, respectively. In Table 7, the life (T 95 ) is the time (Hr) required for the luminance to reach 95% of the initial luminance. Meanwhile, the electroluminescence spectra, luminance vs. luminous efficiency graphs, and time vs. luminance graphs of Examples 1 to 6 are shown in Figures 4, 6, and 7, respectively. [Table 6] [Table 7] [ka] [ka]
[0385] It can be seen from Tables 6 and 7 that the organic light emitting devices of Examples 1 to 6 emit deep blue light and have excellent driving voltage, color purity, luminous efficiency, color conversion efficiency and lifespan.
[0386] Example 7 An organic light-emitting device was fabricated in the same manner as in Example 1, except that, instead of vacuum-depositing Compound D6 (first compound), Compound ETH66 (second compound), and Compound HTH29 (third compound) on the hole transport layer during the formation of the light-emitting layer, Compound D6 (first compound), Compound ETH66 (second compound), Compound HTH29 (third compound), and Compound DFD1 (fourth compound) were vacuum-deposited on the hole transport layer. Here, the content of Compound D6 was 10 wt% based on the total weight (100 wt%) of the light-emitting layer, the content of Compound DFD1 was 0.5 wt% based on the total weight (100 wt%) of the light-emitting layer, and the weight ratio of Compound ETH66 to Compound HTH29 was adjusted to 3:7.
[0387] Example 8 An organic light-emitting device was produced in the same manner as in Example 7, except that the compound DFD2 was used as the fourth compound instead of the compound DFD1.
[0388] Evaluation example 5 1,000 cd / m of the organic light-emitting devices fabricated in Examples 7 and 8 2 Driving voltage (V), color purity (CIEx,y), luminous efficiency (cd / A), color conversion efficiency (cd / A / y), maximum emission wavelength (nm) and lifetime (T 95 ) were measured using the same method as in Evaluation Example 4, and the results are shown in Tables 8 and 9, respectively. Meanwhile, electroluminescence spectra, luminance vs. luminous efficiency graphs, and time vs. luminance graphs of Examples 7 and 8 are shown in FIGS. 5 to 7, respectively. [Table 8] [Table 9] [ka] [ka]
[0389] From Tables 8 and 9, it can be seen that the organic light emitting devices of Examples 7 and 8 emit deep blue light and have excellent driving voltage, color purity, luminous efficiency, color conversion efficiency, and lifespan.
[0390] Example 11 An organic light-emitting device was fabricated in the same manner as in Example 1, except that, instead of forming a 40 nm-thick light-emitting layer by vacuum-depositing Compound D6 (first compound), Compound ETH29 (second compound), and Compound HTH66 (third compound) on the hole-transporting layer, a 30 nm-thick light-emitting layer was formed by vacuum-depositing Compound D6 (first compound) and Compound HTH29 (third compound). Here, the content of Compound D6 was adjusted to 10 wt% based on the total weight (100 wt%) of the light-emitting layer.
[0391] Comparative Example 1 An organic light emitting device was fabricated in the same manner as in Example 11, except that the compound CE1 was used instead of the compound D6 when forming the light emitting layer.
[0392] Evaluation Example 6 1,000 cd / m of the organic light-emitting devices fabricated in Example 11 and Comparative Example 1 2 Driving voltage (V), color purity (CIEx,y), luminous efficiency (cd / A), color conversion efficiency (cd / A / y), maximum emission wavelength (nm) and lifetime (T 95 @room temperature) were measured using the same method as in Evaluation Example 4, and the results are shown in Tables 10 and 11, respectively. Meanwhile, electroluminescence spectra, luminance vs. luminous efficiency graphs, and time vs. luminance graphs of Example 11 and Comparative Example 1 are shown in Figures 4, 6, and 7, respectively. [Table 10] [Table 11] [ka]
[0393] From Tables 10 and 11, it can be seen that the organic light emitting device of Example 11 emits deep blue light and has superior driving voltage, color purity, luminous efficiency, color conversion efficiency, and lifespan characteristics compared to the organic light emitting device of Comparative Example 1. [Explanation of symbols]
[0394] 10 Organic light-emitting device 100 boards 110 1st electrode 130 Middle Class 150 2nd electrode 170 Capping Layer 210 Buffer Layer 220 Active layer 230 Gate insulating film 240 gate electrode 250 Interlayer insulating film 260 Source Electrode 270 Drain electrode 280 Passivation Layer 290 pixel-defined membrane 300 Sealing part 400 Functional Area 500 shading area
Claims
1. A first electrode; a second electrode facing the first electrode; an intermediate layer disposed between the first electrode and the second electrode and including a light-emitting layer; The intermediate layer is i) a first compound represented by the following chemical formula 1; ii) a second compound including a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, or any combination thereof; a third compound including a compound represented by the following chemical formula 3-1, a compound represented by the following chemical formula 3-2, a compound represented by the following chemical formula 3-3, a compound represented by the following chemical formula 3-4, a compound represented by the following chemical formula 3-5, or any combination thereof; a fourth compound capable of emitting delayed fluorescence, or any combination thereof; The first compound, the second compound, the third compound, and the fourth compound are different from each other. 【Chemistry 1】 ...(chemical formula 1) (In the above Chemical Formula 1, M is platinum (Pt) or palladium (Pd), In the above formula 1, X 1 is C, and X 2 to X 4 are, independently of each other, C or N, In the above Chemical Formula 1, i) X 1 The bond between X and M is a coordinate bond; 2 and M, X 3 and M, and X 4 one of the bonds between and M is a coordinate bond and the other two are covalent bonds; In the above Formula 1, the ring CY 1 i) X 1 ii) a group having at least one fused five-membered ring, or ii) a group having at least one fused six-membered ring, 1 the X 1-containing five-membered ring is a pyrrole group, a pyrazole group, an imidazole group, or a triazole group, and the six-membered ring that can be selectively fused to the X 1-containing five-membered ring is a benzene group, a pyridine group, or a pyrimidine group; In the above Formula 1, the ring CY 2 is a benzene group, a pyridine group, a pyrimidine group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, or a dibenzosilole group, In the above formula 1, X 31 ~X 36 , and X 41 ~X 44 are, independently of each other, C or N, In the above formula 1, X 51 is *-N(R 5 )-*', *-B(R 5 )-*', *-P(R 5 )-*', *-C(R 5a ) (R 5b )-*', *-Si(R 5a ) (R 5b )-*', *-Ge(R 5a ) (R 5b )-*', *-S-*', *-Se-*' or *-O-*', wherein the * and the *' are bonding positions to adjacent atoms, In the formula 1, b1 is an integer of 1 to 5; In the above formula 1, R 1 ~R 5 , R 5a and R 5b are each independently a group represented by the following chemical formula 1-1, a group represented by the following chemical formula 1-2, hydrogen, deuterium, —F, a cyano group, at least one R 10a Substituted or unsubstituted C 1 -C 60 an alkyl group, at least one R 10a Substituted or unsubstituted C 2 -C 60 alkenyl group, at least one R 10a Substituted or unsubstituted C 1 -C 60 an alkoxy group, at least one R 10a Substituted or unsubstituted C 3 -C 60 a carbocyclic group, at least one R10a Substituted or unsubstituted C 1 -C 60 Heterocyclic group, at least one R 10a Substituted or unsubstituted C 6 -C 60 an aryloxy group, at least one R 10a Substituted or unsubstituted C 6 -C 60 arylthio group, —C(Q 1 ) (Q 2 ) (Q 3 ), -Si(Q 1 ) (Q 2 ) (Q 3 ), -N(Q 1 ) (Q 2 ), -B(Q 1 ) (Q 2 ), -C(=O)(Q 1 ), -S(=O) 2 (Q 1 ), or -P(=O)(Q 1 ) (Q 2 ) and 【Transformation 3】 ...(Chemical formula 1-1) 【Chemistry 4】 ...(Chemical formula 1-2) In the formula 1, c1 is an integer of 0 to 5, a1 and a4 are each independently an integer of 0 to 4, a2 is an integer of 0 to 8, and a3 is an integer of 0 to 6, provided that the sum of a1 to a4 is 1 or more, and a2 R 2 At least one of a3 R 3 At least one of a4 R 4 At least one of these, or any combination thereof, independently represents a group represented by Chemical Formula 1-1 or a group represented by Chemical Formula 1-2, In the chemical formulas 1, 1-1 and 1-2, L 1 and L 7 are independent of each other, a single bond, or At least one R 10a a substituted or unsubstituted benzene group, naphthalene group, phenanthrene group, cyclopentadiene group, furan group, thiophene group, silole group, indene group, fluorene group, indole group, carbazole group, benzofuran group, dibenzofuran group, benzothiophene group, dibenzothiophene group, benzosilole group, or dibenzosilole group; In Chemical Formula 1-1 and Chemical Formula 1-2, b7 is an integer of 1 to 5; In the above Chemical Formula 1-1 and Chemical Formula 1-2, the ring CY 7 is C 3 -C 60 Carbocyclic group or C 1 -C 60 is a heterocyclic group, In Chemical Formula 1-1 and Chemical Formula 1-2, n7 is an integer of 1 to 5; In the above Chemical Formula 1-1, the ring CY 8 is a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a cyclooctene group, an adamantane group, a norbornene group, a norbornane group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, or a bicyclo[2.2.2]octane group, R in the above Chemical Formula 1-1 7 and R 8 and R 7 in the chemical formula 1-2 are each independently a group represented by the chemical formula 1-1, a group represented by the chemical formula 1-2, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, at least one R 10a Substituted or unsubstituted C 1 -C 60 an alkyl group, at least one R 10a Substituted or unsubstituted C 2 -C 60 alkenyl group, at least one R 10a Substituted or unsubstituted C 2 -C 60 an alkynyl group, at least one R 10a Substituted or unsubstituted C 1 -C 60 an alkoxy group, at least one R 10a Substituted or unsubstituted C 3 -C 60 a carbocyclic group, at least one R10a Substituted or unsubstituted C 1 -C 60 Heterocyclic group, at least one R 10a Substituted or unsubstituted C 6 -C 60 an aryloxy group, at least one R 10a Substituted or unsubstituted C 6 -C 60 arylthio group, —C(Q 1 ) (Q 2 ) (Q 3 ), -Si(Q 1 ) (Q 2 ) (Q 3 ), -N(Q 1 ) (Q 2 ), -B(Q 1 ) (Q 2 ), -C(=O)(Q 1 ), -S(=O) 2 (Q 1 ), or -P(=O)(Q 1 ) (Q 2 ) and In the formula 1-2, R 8 and R 9 are each independently a C 1 -C 60 alkyl group substituted or unsubstituted with at least one R 10a , a C 3 -C 60 carbocyclic group substituted or unsubstituted with at least one R 10a , or a C 1 -C 60 heterocyclic group substituted or unsubstituted with at least one R 10a ; In the formula 1-1 and the formula 1-2, a7 and a8 are each independently an integer of 0 to 15; <Chemical formula 3-1> 【change】 <Chemical formula 3-2> 【change】 <Chemical formula 3-3> 【change】 <Chemical formula 3-4> 【change】 <Chemical formula 3-5> 【change】 In the above Chemical Formulas 3-1 to 3-5, rings CY 71 to CY 84 each independently represent a π-electron-rich C 3 -C 60 cyclic group or a pyridine group; X 82 is a single bond, O, S, N—[(L 82 ) b82 —R 82 ], C(R 82a )(R 82b ) or Si(R 82a )(R 82b ); X 83 is a single bond, O, S, N—[(L 83 ) b83 —R 83 ], C(R 83a )(R 83b ) or Si(R 83a )(R 83b ); X 84 is O, S, N—[(L 84 ) b84 —R 84 ], C(R 84a )(R 84b ) or Si(R 84a )(R 84b ); X 85 is C or Si; L 81 to L 85 are each independently a single bond, *-C(Q 4 )(Q 5 )-*', *-Si(Q 4 )(Q 5 )-*', a π-electron rich C 3 -C 60 cyclic group unsubstituted or substituted with at least one R 10a , or a pyridine group unsubstituted or substituted with at least one R 10a ; b81 to b85 are each independently an integer from 1 to 5; R 71 to R 74 , R 81 to R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b are each independently hydrogen, deuterium, —F, a cyano group, a C 1 -C 60 alkyl group substituted or unsubstituted with at least one R 10a , a C 2 -C 60 alkenyl group substituted or unsubstituted with at least one R 10a , a C 1 -C 60 alkenyl group substituted or unsubstituted with at least one R 10a , a C 3 -C 60 carbocyclic group substituted or unsubstituted with at least one R 10a , a C 1 -C 60 heterocyclic group substituted or unsubstituted with at least one R 10a , C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ) or —P(═O)(Q 1 )(Q 2 ); a71 to a74 are each independently an integer from 0 to 20; a1 *-(L 1 ) b1 - (R 1 ) c1 Two or more of the groups represented by 10a Substituted or unsubstituted C 3 -C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C 1 -C 60 forming a heterocyclic group, a2 R 2 two or more of the R 10a Substituted or unsubstituted C 3 -C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C 1 -C 60 forming a heterocyclic group, a3 R 3 two or more of the R 10a Substituted or unsubstituted C 3 -C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C 1 -C 60 forming a heterocyclic group, a4 R 4 two or more of the R 10a Substituted or unsubstituted C 3 -C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C 1 -C 60 forming a heterocyclic group, The aforementioned R 1 ~R 5 , R 5a and R 5b two or more of the R 10a Substituted or unsubstituted C 3 -C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C 1 -C 60 forming a heterocyclic group, The R 10a teeth, deuterium (-D), -F, or a cyano group; Deuterium, -F, cyano group, -Si(Q 11 ) (Q 12 ) (Q 13 ), or any combination thereof, substituted or unsubstituted, C 1 -C 60 Alkyl group, C 2 -C 60 alkenyl group, or C 1 -C 60 an alkoxy group; Deuterium, -F, cyano group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 1 -C 60 Alkoxy group, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 arylthio group, -Si(Q 21 ) (Q 22 ) (Q 23 ), (Q 22 ), -C(=O)(Q 21 ), -S(=O) 2 (Q 21 ), -P(=O)(Q 21 ) (Q 22 ), or any combination thereof, substituted or unsubstituted, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group or C 6 -C 60 an arylthio group; or -Si(Q 31 ) (Q 32 ) (Q 33 ); and The aforementioned Q 1 ~Q 3 , Q4 to Q5, Q 11 ~Q 13 , Q 21 ~Q 23 , and Q 31 ~Q 33 are independent of each other, C 1 -C 60 alkyl groups, or Deuterium, -F, cyano group, C 1 -C 60 Alkyl group, C 1 -C 60 C which is unsubstituted or substituted with an alkoxy group, a phenyl group, a biphenylyl group, or any combination thereof 3 -C 60 Carbocyclic group or C 1 -C 60 a heterocyclic group; The third compound is not CBP or mCBP described below. 【Transformation 5】
2. The light-emitting device according to claim 1 , wherein the intermediate layer comprises the second compound.
3. The light-emitting device of claim 2 , wherein the intermediate layer further comprises the third compound, the fourth compound, or a combination thereof.
4. 2. The light-emitting device according to claim 1, wherein the fourth compound is a compound containing at least one cyclic group containing B (boron) and N (nitrogen) as ring-forming atoms.
5. the fourth compound includes a fused ring in which one or more third rings and one or more fourth rings are fused to each other, the third ring is a group having a ring structure selected from cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclopentene, cyclohexene, cycloheptene, cyclooctene, adamantane, norbornene, norbornane, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane, benzene, pyridine, pyrimidine, pyridazine, pyrazine, and triazine; 2. The light-emitting element according to claim 1, wherein the fourth ring is a group having a ring structure selected from 1,2-azaborinin, 1,3-azaborinin, 1,4-azaborinin, 1,2-dihydro-1,2-azaborinin, 1,4-oxaborinin, 1,4-thiaborinine, and 1,4-dihydroborinine.
6. The light-emitting device according to claim 1 , wherein the intermediate layer comprises the fourth compound.
7. i) the first compound, and ii) the second compound, the third compound, the fourth compound, or any combination thereof, are contained in the light-emitting layer; The light-emitting device according to claim 1 , wherein the light-emitting layer emits phosphorescence or fluorescence emitted from the first compound.
8. The light-emitting device according to claim 7 , wherein the phosphorescence or fluorescence emitted from the first compound is blue light.
9. In the above Chemical Formula 1, a4 is an integer of 1 to 4, and the a4 R 4 2. The light-emitting device according to claim 1, wherein at least one of the following is, independently of each other, a group represented by Chemical Formula 1-1 or a group represented by Chemical Formula 1-2.
10. In the above Chemical Formula 1-1 and Chemical Formula 1-2, the ring CY 7 is i) a first ring, ii) a second ring, iii) a fused ring in which two or more first rings are fused to each other, iv) a fused ring in which two or more second rings are fused to each other, or v) a fused ring in which one or more first rings and one or more second rings are fused to each other, the first ring is a group having a ring structure selected from cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclopentene, cyclohexene, cycloheptene, cyclooctene, adamantane, norbornene, norbornane, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane, and benzene; 2. The light-emitting element according to claim 1, wherein the second ring is a group having a ring structure selected from pyrrole, furan, thiophene, silole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiadiazole, pyridine, pyrimidine, pyridazine, pyrazine, triazine, 1,2-azaborinin, 1,3-azaborinin, 1,4-azaborinin, 1,2-dihydro-1,2-azaborinin, 1,4-oxaborinin, 1,4-thiaborinine, and 1,4-dihydroborinine.
11. In the above Chemical Formula 1-1, the ring CY 8 The light-emitting device according to claim 1, wherein is a group represented by one of the following chemical formulas CY8-1 to CY8-8. 【Transformation 6】 (In the chemical formulas CY8-1 to CY8-8, * indicates the bonding position to the adjacent atom in chemical formula 1, and *' indicates the bonding position to L7 in chemical formula 1-.)
12. The light emitting device of claim 1 , wherein the second compound comprises a compound represented by the following Chemical Formula 2: 【Transformation 7】 ...(chemical formula 2) (In the above Chemical Formula 2, L 51 ~L 53 are each independently a single bond, at least one R 10a Substituted or unsubstituted C 3 -C 60 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C 1 -C 60 is a heterocyclic group, b51 to b53 are each independently an integer from 1 to 5; X 54 is N or C(R 54 ) and X 55 is N or C(R 55 ) and X 56 is N or C(R 56 ) and X 54 Or X 56 At least one of them is N, R 51 ~R 56 are each independently hydrogen, deuterium, —F, a cyano group, at least one R 10a Substituted or unsubstituted C 1 -C 60 an alkyl group, at least one R 10a Substituted or unsubstituted C 2 -C 60 alkenyl group, at least one R 10a Substituted or unsubstituted C 1 -C 60 an alkoxy group, at least one R 10a Substituted or unsubstituted C 3 -C 60 a carbocyclic group, at least one R10a Substituted or unsubstituted C 1 -C 60 Heterocyclic group, at least one R 10a Substituted or unsubstituted C 6 -C 60 an aryloxy group, at least one R 10a Substituted or unsubstituted C 6 -C 60 arylthio group, —C(Q 1 ) (Q 2 ) (Q 3 ), -Si(Q 1 ) (Q 2 ) (Q 3 ), -N(Q 1 ) (Q 2 ), -B(Q 1 ) (Q 2 ), -C(=O)(Q 1 ), -S(=O) 2 (Q 1 ), or -P(=O)(Q 1 ) (Q 2 )
13. The light-emitting device of claim 1 , wherein the fourth compound comprises a compound represented by the following chemical formula 502, a compound represented by the following chemical formula 503, or any combination thereof: 【Chemistry 12】 ...(Chemical formula 502) 【Chemistry 13】 ...(Chemical formula 503) (In the chemical formula 502 and the chemical formula 503, Ring A 501 ~Ring A 504 are, independently of each other, C 3 -C 60 Carbocyclic group or C 1 -C 60 is a heterocyclic group, Y 505 is O, S, N (R 505 ), B(R 505 ), C(R 505a ) (R 505b ) or Si(R 505a ) (R 505b ) and Y 506 is O, S, N (R 506 ), B(R 506 ), C(R 506a ) (R 506b ) or Si(R 506a ) (R 506b ) and Y 507 is O, S, N (R 507 ), B(R 507 ), C(R 507a ) (R 507b ) or Si(R 507a ) (R 507b ) and Y 508 is O, S, N (R 508 ), B(R 508 ), C(R 508a ) (R 508b ) or Si(R 508a ) (R 508b ) and Y 51 and Y 52 are, independently of each other, B, P(=O) or S(=O), R 500a , R 500b , R 501 ~R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b are each independently hydrogen, deuterium, —F, a cyano group, at least one R 10a Substituted or unsubstituted C 1 -C 60 an alkyl group, at least one R 10a Substituted or unsubstituted C 2 -C 60 alkenyl group, at least one R 10a Substituted or unsubstituted C 1 -C 60 an alkoxy group, a C substituted or unsubstituted with at least one R 1 -C 60 an alkoxy group, at least one R 10a Substituted or unsubstituted C 3 -C 60 a carbocyclic group, at least one R10a Substituted or unsubstituted C 1 -C 60 Heterocyclic group, at least one R 10a Substituted or unsubstituted C 6 -C 60 an aryloxy group, at least one R 10a Substituted or unsubstituted C 6 -C 60 arylthio group, —C(Q 1 ) (Q 2 ) (Q 3 ), -Si(Q 1 ) (Q 2 ) (Q 3 ), -N(Q 1 ) (Q 2 ), -B(Q 1 ) (Q 2 ), -C(=O)(Q 1 ), -S(=O) 2 (Q 1 ), or -P(=O)(Q 1 ) (Q 2 ) and a501 to a504 are each independently an integer from 0 to 20.
14. An electronic device comprising a light-emitting element according to any one of claims 1 to 13.
15. further comprising a thin film transistor; the thin film transistor includes a source electrode and a drain electrode; The electronic device according to claim 14 , wherein the first electrode of the light-emitting element is electrically connected to at least one of a source electrode and a drain electrode of the thin film transistor.
16. 15. The electronic device of claim 14, further comprising a color filter, a color conversion layer, a touchscreen layer, a polarizing layer, or any combination thereof.
Citation Information
Patent Citations
Manufacturing method of transition metal complex and transition metal complex
JP2007045742A
Methods of manufacturing gate insulating film, organic transistor, and organic electroluminescent display device, and display
JP2008140786A
Organic light-emitting element and electronic device including the same
JP2019169710A
Organometallic compound, organic light-emitting device including the organometallic compound and electronic apparatus including the organic light-emitting device
JP2021084910A
Organometallic compound, organic light emitting device including the same and a composition for diagnosing including the same
KR1020200076583A