Fused ring compound, light-emitting device including the same, and electronic device
Patent Information
- Application Number
- CN202210105984.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2021-02-01
- Filing Date
- 2022-01-28
- Publication Date
- 2026-09-22
- Estimated Expiration
- 2042-01-28
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Figure CN114843411B_ABST
Abstract
Description
[0001] Cross-references to related applications
[0002] This application claims priority and benefit to Korean Patent Application No. 10-2021-0014337, filed on February 1, 2021, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field
[0003] One or more aspects of embodiments of this disclosure relate to fused ring compounds, light-emitting devices including fused ring compounds, and electronic devices including light-emitting devices. Background Technology
[0004] The light-emitting device is a self-emitting device, which has excellent or appropriate characteristics in terms of wide viewing angle, high contrast, short response time and / or brightness, driving voltage and / or response speed.
[0005] An example light-emitting device includes a first electrode on a substrate, and a hole transport region, an emitter layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes supplied from the first electrode can move towards the emitter layer through the hole transport region, and electrons supplied from the second electrode can move towards the emitter layer through the electron transport region. Charge carriers (such as holes and electrons) can then recombine in the emitter layer to generate excitons. These excitons can transition from an excited state to a ground state, thereby generating light. Summary of the Invention
[0006] One or more aspects of embodiments of this disclosure relate to novel fused-ring compounds, light-emitting devices including fused-ring compounds, and electronic devices including light-emitting devices.
[0007] Other aspects will be set forth in part in the description which follows, and will be apparent in part from the description, or may be learned by practice of the embodiments presented in this disclosure.
[0008] One or more embodiments of this disclosure provide fused-ring compounds represented by Formula 1:
[0009] Formula 1
[0010]
[0011] In formula 1 (e.g., a triterpenoid molecule, for example having a core formed by the fusion of a bicyclic [2.2.2]octane with three independent phenyl groups at each pair of non-bridged carbon atoms),
[0012] G1 can be a group represented by Formula 2, and
[0013] G2 can be a group represented by one of formulas 3A to 3C.
[0014] Formula 2
[0015]
[0016] Formula 3A
[0017]
[0018] Formula 3B
[0019]
[0020] 3C
[0021]
[0022] In Equations 1, 2, and 3A to 3C
[0023] X 31 It can be N(R) 35 ), O or S,
[0024] Z 31 It can be C(R) 36 ) or N, Z 32 It can be C(R) 37 ) or N, Z 33 It can be C(R) 38 ) or N, and Z 31 To Z 33 At least one of them can be N,
[0025] L 21 To L 23 and L 31 To L 34 Each can be independently a single bond, unsubstituted, or bonded by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0026] a21 to a23 and a31 to a34 can each be an integer selected from 1 to 3 independently.
[0027] Ar 21 To Ar 23 Ar 31 and Ar 32 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups or -Si(Q1)(Q2)(Q3),
[0028] b21 to b23, b31 and b32 can each be an integer selected from 1 to 5 independently.
[0029] R1 to R5 and R 31 To R 38 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic group, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy, unsubstituted, or with at least one R 10a Replacement C6-C 60 Arylthioyl, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2),
[0030] c1, c2, and c33 can each be an integer selected from 1 to 3 independently.
[0031] c3, c31, c32, and c34 can each be an integer selected from 1 to 4 independently, and
[0032] R 10a Possible forms:
[0033] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro,
[0034] Each of the following C1-C that was not replaced or was replaced by: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60Aryloxy group, C6-C 60 Arylthioyl, -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,
[0035] Each of the following C3-Cs was not replaced or was replaced by the others 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 aryloxy or C6-C 60 Aryl thiols: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthioyl, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) or any combination thereof, or
[0036] -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 ),
[0037] Among them, Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 They can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy groups, or C3-C groups that are either unsubstituted or substituted with the following: 60 carbonyl group or C1-C 60 Heterocyclic groups: deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, phenyl, biphenyl, or any combination thereof.
[0038] One or more embodiments of this disclosure provide a light-emitting device comprising: a first electrode, a second electrode facing the first electrode, and an interlayer between the first electrode and the second electrode and including an emitting layer, wherein the light-emitting device may include a fused ring compound represented by Formula 1.
[0039] One or more embodiments of this disclosure provide an electronic device including a light-emitting device. Attached Figure Description
[0040] The above and other aspects, features, and advantages of certain embodiments of this disclosure will become more apparent from the following description taken in conjunction with the accompanying drawings, wherein:
[0041] Figure 1 This is a schematic cross-sectional view of the light-emitting device according to an embodiment;
[0042] Figure 2 This is a schematic cross-sectional view of a light-emitting device according to an embodiment; and
[0043] Figure 3 This is a schematic cross-sectional view of a light-emitting device according to another embodiment. Detailed Implementation
[0044] Reference will now be made in more detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout and are not repeatedly described. In this regard, embodiments may take different forms and should not be construed as limited to the descriptions set forth herein. Therefore, embodiments are described below with reference to the accompanying drawings only to explain aspects of this description. As used herein, the term “and / or” includes any and all combinations of one or more of the associated enumerated items. Throughout this disclosure, the expression “at least one of a, b, and c” indicates only a, only b, only c, both a and b (e.g., simultaneously), both a and c (e.g., simultaneously), both b and c (e.g., simultaneously), all of a, b, and c, or variations thereof.
[0045] As used herein, the singular forms “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise. It will be further understood that the terms “include,” “including,” “comprise,” and / or “comprising,” when used in this specification, specify the presence of the described features, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more other features, steps, operations, elements, components, and / or groups thereof.
[0046] As used herein, the terms “use,” “using,” and “used” are considered synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively. As used herein, expressions such as “at least one of,” “one of,” and “selected from” before / after a list of elements modify the entire list of elements, but not individual elements of the list. Furthermore, the use of “may” when describing embodiments of this disclosure refers to “one or more embodiments of this disclosure.”
[0047] Fused ring compounds can be represented by Formula 1:
[0048] Formula 1
[0049]
[0050] In Equation 1,
[0051] G1 can be a group represented by Formula 2, and
[0052] G2 can be a group represented by one of formulas 3A to 3C:
[0053] Formula 2
[0054]
[0055] Formula 3A
[0056]
[0057] Formula 3B
[0058]
[0059] 3C
[0060]
[0061] In Equation 3B, X 31 It can be N(R) 35 ), O or S.
[0062] In equation 3C, Z 31 It can be C(R) 36 ) or N, Z 32 It can be C(R) 37 ) or N, Z 33 It can be C(R) 38 ) or N, and Z 31 To Z 33 At least one of them can be N.
[0063] In the implementation method, in formula 3C,
[0064] Z 31 It can be N or Z 32 It can be C(R) 37 ), and Z 33 It can be C(R) 38 ),
[0065] Z 31 It can be C(R) 36 Z 32 It can be N, and Z 33 It can be C(R) 38 ),
[0066] Z 31 It can be C(R) 36 Z 32 It can be C(R) 37 ), and Z 33 It can be N,
[0067] Z 31 and Z 32 Each can be N, and Z 33 It can be C(R) 38 ),
[0068] Z 32 and Z 33 Each can be N, and Z31 It can be C(R) 36 ),
[0069] Z 31 and Z 33 Each can be N, and Z 32 It can be C(R) 37 ),or
[0070] Z 31 To Z 33 Each can be N.
[0071] In Equations 2 and 3A to 3C, L 21 To L 23 and L 31 To L 34 Each can be independently a single bond, unsubstituted, or bonded by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group.
[0072] In Equations 2 and 3A to 3C, a21 to a23 and a31 to a34 can respectively indicate L. 21 To L 23 and L 31 To L 34 The quantity. a21 to a23 and a31 to a34 can each be an integer selected from 1 to 3 independently.
[0073] In the implementation, L 21 To L 23 and L 31 To L 34 Each can be independently:
[0074] Single key; or
[0075] Each of the following is either unsubstituted or substituted: phenyl, pentanenyl, indene, naphthyl, azuleyl, heptenyl, indaneyl, acenaphtheyl, fluorenyl, spiro-difluorenyl, spiro-benzofluorenyl-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthreneyl, phenanthreneyl, anthraceneyl, fluoranyl, pyreneyl, 1,2-benzophenanthreneyl, tetraphenyl, lavany, peryleneyl, pyrroleyl, thiopheneyl, furanyl, thiorheyl, imidazolyl, pyrazolyl, thiazolyl, isothiazyl Azolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazole, benzothiophenyl, dibenzothiophenyl, quinolinyl, isoquinolinyl, benzimidazolyl, imidazopyridyl or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, pentanenyl, indene, naphthyl, azuleyl, heptenyl, indaneyl, acenaphthyl, fluorenyl, spiro-difluorenyl, spiro-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthraceneyl, fluoranyl, pyrene, 1,2-benzophenanthreneyl, tetraphenyl, lavany, peryl, pyrroleyl, thiopheneyl, furanyl, thiopheneyl Imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, benzothiophenyl, dibenzothiophenyl, quinolinyl, isoquinolinyl, benzimidazolyl, imidazopyridyl, imidazopyrimidinyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) or any combination thereof,
[0076] Q 31 To Q 33 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl.
[0077] In one or more embodiments, L 21 To L 23 and L 31 To L 34 Each can be independently represented by one of the groups from Formula 3-1 to Formula 3-24:
[0078]
[0079]
[0080] Among them, in equations 3-1 to 3-24,
[0081] Y1 can be C(Z3)(Z4), Si(Z5)(Z6), N(Z7), O, or S.
[0082] Z1 to Z7 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene, 1,2-benzo[a]phenanthryl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, dibenzothiopheneyl, quinolinyl, isoquinolinyl, benzimidazolyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) or -B(Q 31 (Q) 32 ),
[0083] d3 can be an integer selected from 1 to 3.
[0084] d4 can be an integer selected from 1 to 4.
[0085] d5 can be an integer selected from 1 to 5.
[0086] d6 can be an integer selected from 1 to 6.
[0087] d8 can be an integer selected from 1 to 8.
[0088] Q 31 To Q 33 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, and
[0089] *, *', and *” each indicate a binding site with an adjacent atom.
[0090] In some embodiments, in Equations 2 and 3A to 3C, a21 to a23 and a31 to a34 may each be 1, and L 21 To L 23 and L 31 To L 34 Each can be an independent single bond or a group represented by one of formulas 3-1 to 3-3 and 3-24:
[0091]
[0092] Among them, in equations 3-1 to 3-3 and equation 3-24,
[0093] Z1, d3, and d4 can be understood by referring to the descriptions of Z1, d3, and d4 provided in this document, and
[0094] *, *', and *” each indicate a binding site with an adjacent atom.
[0095] In Equations 2 and 3C, Ar 21 To Ar 23 Ar 31 and Ar 32 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups or -Si(Q1)(Q2)(Q3),
[0096] Q1 to Q3 can each be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy groups; or C3-C groups that are unsubstituted or substituted with the following: 60 carbonyl group or C1-C 60 Heterocyclic groups: deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, phenyl, biphenyl, or any combination thereof.
[0097] In the implementation method, Ar 21 To Ar 23 Ar 31 and Ar 32 Each can be independently:
[0098] Each of the following is either unsubstituted or substituted: cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, terphenyl, fluorenyl, spiro-difluorenyl, spiro-cyclopentane-fluorenyl, spiro-cyclohexane-fluorenyl, spiro-fluorenyl-benzo[fluorenyl], benzo[fluorenyl], dibenzo[fluorenyl], phenatenyl, phenanthrene, anthracene, fluoranyl, triphenylene, pyrene, 1 2-Benzenyl, Perylene, Pentenyl, Hexaphenyl, Pentaphenyl, Pyrrole, Thiophene, Furanyl, Thirrolyl, Imidazolyl, Pyrazolyl, Thiazolyl, Isothiazolyl, Oxazolyl, Isoxazolyl, Pyridyl, Pyrazinyl, Pyrimidinyl, Pyridazinyl, Triazinyl, Indolyl, Isoyindolyl, Indolyl, Puryl, Quinolinyl, Isoquinolinyl, Benzoquinolinyl, Phtharazinyl, Naphthidyl, Quinoxolinyl, Quinazolinyl, Pyrolinyl, Phenyridyl, Phenyridyl, Acridineyl, Phenyrrolinyl, Phenazinyl, Benzimidazolyl, Benzofuranyl, Benzothiophene, Benzothiopyrroleyl, Benzoisothiazolyl, Benzooxazolyl, Benzoisooxazolyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Dibenzofuranyl, Dibenzothiophene, Dibenzothiopyrroleyl, Carbohydrate Azolyl, benzocarbazoyl, dibenzocarbazoyl, azafluorenyl, azaspiro-difluorenyl, azacarbazoyl, diazacarbazoyl, azadibenzofuranyl, azadibenzothiopheneyl, azadibenzothiopheneyl, imidazopyridyl or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, terphenyl, fluorenyl, spiro-difluorenyl, spiro-cyclopentane-fluorenyl, spiro-cyclohexane-fluorenyl, spiro-fluorenyl-benzo[fluorenyl], benzo[fluorenyl], dibenzo[fluorenyl], phenanthrenyl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthrene, perylene, penfenyl, hexaphenyl, pentaphenyl, pyrroleyl, thiopheneyl, furanyl, thiopheneyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indoleyl, isoyindolyl, indazoleyl, purineyl, quinolinyl, iso Quinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiopheneyl, benzothiopyrrolyl, benzoisothiazolyl, benzooxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, dibenzofuranyl, dibenzothiopheneyl, dibenzothiopyrrolyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, azafluorenyl, azaspiro-difluorenyl, azacarbazoleyl, diazacarbazoleyl, azadibenzofuranyl, azadibenzothiopheneyl, azadibenzothiopyrrolyl, imidazopyridyl, imidazopyrimidinyl, -Si(Q) 31 (Q) 32 (Q)33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) or any combination thereof; or
[0099] -Si(Q1)(Q2)(Q3),
[0100] Among them, Q1 to Q3 and Q 31 To Q 33 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl.
[0101] In one or more embodiments, Ar in Formula 2 and Formula 3C 21 To Ar 23 Ar 31 and Ar 32 Each can be independently represented by a group from Formula 5-1 to Formula 5-19 or -Si(Q1)(Q2)(Q3):
[0102]
[0103]
[0104] Among them, in equations 5-1 to 5-19,
[0105] Y 51 It can be O, S, N (Z) 53 ), C(Z) 54 (Z) 55 ) or Si(Z 56 (Z) 57 ),
[0106] Z 51 To Z 57 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, pyrene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, dibenzothiopheneyl, quinolinyl, isoquinolinyl, benzimidazolyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) or -B(Q 31 (Q) 32 ),
[0107] e3 can be an integer selected from 1 to 3.
[0108] e4 can be an integer selected from 1 to 4.
[0109] e5 can be an integer selected from 1 to 5.
[0110] e6 can be an integer selected from 1 to 6.
[0111] e7 can be an integer selected from 1 to 7, and
[0112] e9 can be an integer selected from 1 to 9.
[0113] Among them, Q1 to Q3 and Q 31 To Q 33 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, and
[0114] * Indicates the binding site with adjacent atoms.
[0115] In some implementations, Ar 21 To Ar 23 Ar 31 and Ar 32 Each can be independently represented by one of the groups from Formula 6-1 to Formula 6-42:
[0116]
[0117]
[0118] Among them, in equations 6-1 to 6-42,
[0119] “t-Bu” represents tert-butyl.
[0120] “Ph” represents phenyl.
[0121] "TMS" stands for trimethylsilyl.
[0122] “TPS” stands for triphenylsilyl, and
[0123] * Indicates the binding site with adjacent atoms.
[0124] In the implementation method, in Equation 2, L 21 To L 23 It can be a single bond or a group represented by one of Formulas 3-1 to 3-3 and 3-24, and Ar 21 To Ar 23 Each of these can be a group represented by one of Formulas 6-1, 6-14, 6-15, 6-18, and 6-36:
[0125]
[0126]
[0127] Among them, in equations 3-1 to 3-3, 3-24, 6-1, 6-14, 6-15, 6-18, and 6-36,
[0128] Z1, d3, and d4 can be understood by referring to the descriptions of Z1, d3, and d4 provided in this document.
[0129] Q 31 To Q 33 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl,
[0130] “Ph” represents phenyl, and
[0131] *, *', and *” each indicate a binding site with an adjacent atom.
[0132] In one or more embodiments, in Equation 2, by *-(L 21 ) a21 -(Ar 21 ) b21 、*-(L 22 ) a22 -(Ar 22 ) b22 and *-(L 23 ) a23 -(Ar 23 ) b23 The represented groups can each be independently represented by one of the groups represented by formulas 2A-1 to 2A-7:
[0133]
[0134] Among them, in equations 2A-1 to 2A-7,
[0135] * Indicates the binding site with adjacent atoms.
[0136] In Equations 1, 2, and 3A to 3C, R1 to R5 and R 31 To R 38 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic group, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy, unsubstituted, or with at least one R 10a Replacement C6-C 60 Arylthioyl, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2),
[0137] Q1 to Q3 can each be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy groups; or C3-C groups that are unsubstituted or substituted with the following: 60 carbonyl group or C1-C 60 Heterocyclic groups: deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 alkoxy, phenyl, biphenyl, or any combination thereof
[0138] c1, c2, and c33 can each be an integer selected from 1 to 3 independently, and
[0139] c3, c31, c32, and c34 can each be an integer selected from 1 to 4 independently.
[0140] In the embodiments, the fused-ring compound represented by Formula 1 can satisfy one of the following criteria:
[0141] (i) At least one of R1 to R5 in Equation 1 can be deuterium.
[0142] (ii) Ar in Equation 2 21 To Ar 23 At least one of them can be replaced by deuterium.
[0143] (iii) When G2 is a group represented by formula 3A, R 31 and R 32 At least one of them can be deuterium, or R 31 and R 32 At least one of them can be replaced by deuterium.
[0144] (iv) When G2 is a group represented by formula 3B, R 33 and R 34 At least one of them can be deuterium, or R 33 To R 35 At least one of them can be replaced by deuterium.
[0145] (v) When G2 is a group represented by formula 3C, Ar 31 and Ar 32 At least one of them can be replaced by deuterium, or
[0146] One of (vi)(iii) to (v), and any combination of (i) and (ii).
[0147] In the implementation, in Formula 1, R1 to R5 can each be hydrogen.
[0148] In some embodiments, R in Formulas 3A to 3C 31 To R 38 Each can be independently: hydrogen, deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isonyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, tert-decyl or -Si(Q1)(Q2)(Q3); or
[0149] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothiophene, carbazole, or dibenzothiophene: deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, tert-decyl, phenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothiophene, carbazole, dibenzothiophene, -Si(Q) 31 (Q) 32 (Q) 33 ) or any combination thereof,
[0150] Among them, Q1 to Q3 and Q 31 To Q 33 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl.
[0151] In some implementations, R 31 To R 38 Each of these groups can independently be hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isonyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, tert-decyl, -Si(Q1)(Q2)(Q3) or a group represented by one of formulas 6-1 to 6-42:
[0152]
[0153]
[0154] In Equations 6-1 to 6-42, "t-Bu" represents tert-butyl.
[0155] “Ph” indicates phenyl, and “TMS” indicates trimethylsilyl, “TPS” indicates triphenylsilyl, and * indicates the binding site with adjacent atoms.
[0156] In an implementation, G1 in Formula 1 can be a group represented by Formula 2(1):
[0157] Equation 2(1)
[0158]
[0159] In Equation 2(1),
[0160] R 21 To R 23 Each can be independently associated with R 10a same,
[0161] c21 to c23 can each be an integer selected from 0 to 5 independently, and
[0162] * Indicates the binding site with adjacent atoms.
[0163] In some implementations, in equation 2(1), R 21 To R 23 Each can be independently:
[0164] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl or C1-C 20 Alkoxy;
[0165] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, dibenzothiopheneyl, quinolinyl, isoquinolinyl, or benzimidazolyl; or
[0166] -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) or -B(Q 31 (Q) 32 ).
[0167] In the implementation, in Formula 1, G2 can be a group represented by one of Formulas 3C(1) to 3C(5):
[0168]
[0169]
[0170] In equations 3C(1) to 3C(5),
[0171] L 34 It can be a group represented by formula 3-2 or formula 3-3.
[0172] L 32 L33 a32, a33, Ar 31 Ar 32 b31 and b32 can be respectively obtained through L in reference formula 3C 32 L 33 a32, a33, Ar 31 Ar 32 To understand from the descriptions of b31 and b32, and
[0173] * Indicates the binding site with adjacent atoms.
[0174] In some embodiments, in equations 3C(1) to 3C(5),
[0175] L 32 and L 33 Each can be an independent single bond or a group represented by one of formulas 3-1 to 3-3.
[0176] a32 and a33 can each be 1.
[0177] Ar 31 and Ar 32 Each can be independently represented by a group from Formula 6-1 to Formula 6-42, and
[0178] b31 and b32 can each be 1.
[0179] R 10a It can be: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, or nitro;
[0180] Each of the following C1-C that was not replaced or was replaced by: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthioyl, -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;
[0181] Each of the following C3-Cs was not replaced or was replaced by the others 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 aryloxy or C6-C 60 Aryl thiols: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthioyl, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) or any combination thereof; or
[0182] -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
[0183] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each can be independently represented as: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C60 Alkoxy groups; or C3-C groups that are unsubstituted or substituted with the following: 60 carbonyl group or C1-C 60 Heterocyclic groups: deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, phenyl, biphenyl, or any combination thereof.
[0184] For example, the fused-ring compound represented by Formula 1 may be selected from compounds A-1 to A-240 and compounds C-1 to C-136, but the embodiments are not limited thereto:
[0185]
[0186]
[0187]
[0188]
[0189]
[0190]
[0191]
[0192]
[0193]
[0194]
[0195]
[0196]
[0197]
[0198]
[0199]
[0200]
[0201]
[0202]
[0203]
[0204]
[0205] Fused-ring compounds represented by Formula 1 can have a tripterene core with high electron transport capacity, thus exhibiting high electron transport capacity (e.g., transport capability). For example, the G1 and G2 substituents can be attached to the 1'- and 8'- positions of the tripterene core, respectively, thus giving the fused-ring compound represented by Formula 1 a structure with large intramolecular interactions (e.g., the G1 and G2 substituents can participate in spatial interactions with each other due to their large size and position on the tripterene core). Consequently, the dihedral angle between the two phenyl groups (e.g., between the G1-substituted phenyl group and the G2-substituted phenyl group on the tripterene core) can be increased (e.g., to alleviate strain in the molecule), thus giving the fused-ring compound represented by Formula 1 a high triplet energy.
[0206] The G1 substituent can be a silyl group bonded to the tripterene core via a single bond (e.g., direct bonding), thus the dihedral angle in the core may increase due to the steric effect of the bulky silyl group as the G1 substituent. Therefore, the fused-ring compound represented by Formula 1 can have a high triplet energy level, and the fused-ring compound represented by Formula 1 can have excellent or suitable properties for use as a sandwich material (e.g., a luminescent material) in a light-emitting device.
[0207] In one or more embodiments, by incorporating a hole-transporting group represented by Formula 3A or Formula 3B into the tripterene core, control over the energy levels and polarity of the fused-ring compound represented by Formula 1 can be facilitated by the introduction of one or more suitable substituents and changes in substitution positions (e.g., via the N atom in Formula 3A or via the C atom in the benzene ring in Formula 3B). Therefore, the fused-ring compound represented by Formula 1 can have a high charge balance, and a light-emitting device comprising the fused-ring compound represented by Formula 1 can have high luminous efficiency.
[0208] In one or more embodiments, the fused-ring compound represented by Formula 1 can have improved electron transport properties by incorporating an electron-transporting group represented by Formula 3C into the triterpenoid core, thereby facilitating energy transfer. For example, when the fused-ring compound represented by Formula 1 is included in the interlayer (e.g., emitting layer, electron transport layer, and / or hole blocking layer) of the light-emitting device, the light-emitting device can have high luminous efficiency and / or long lifetime.
[0209] Therefore, electronic devices (e.g., light-emitting devices) that include fused-ring compounds represented by Formula 1 can have low driving voltage, high luminous efficiency, long lifetime and / or high colorimetric purity.
[0210] By referring to the synthetic examples and embodiments described herein, those skilled in the art can readily understand the method for synthesizing the fused-ring compounds represented by Formula 1.
[0211] Fused ring compounds represented by Formula 1 can be used in light-emitting devices (e.g., organic light-emitting devices).
[0212] According to one or more embodiments, the light-emitting device may include: a first electrode; a second electrode facing the first electrode; and an interlayer between the first electrode and the second electrode, including an emitting layer, wherein the light-emitting device may include a fused ring compound represented by Formula 1.
[0213] As used herein, the term "interlayer" can refer to a single layer and / or multiple layers located between the first and second electrodes in a light-emitting device.
[0214] In an embodiment, the interlayer in the light-emitting device may include a fused-ring compound represented by Formula 1. For example, the emitting layer may include a fused-ring compound represented by Formula 1.
[0215] In one or more embodiments, the emitting layer may include a host and a dopant, wherein the content of the host in the emitting layer may be greater than the content of the dopant in the emitting layer, and the host may include a fused-ring compound represented by Formula 1. For example, a fused-ring compound represented by Formula 1 may be used as the host. The dopant may include a phosphorescent dopant and / or a thermally activated delayed fluorescence (TADF) dopant.
[0216] In one or more embodiments, the host may include a fused-ring compound represented by Formula 1, and the dopant may emit blue light. In some embodiments, the dopant may include a transition metal and m ligands, where m may be an integer selected from 1 to 6. The ligands may be the same or different from each other, and at least one of the m ligands may be bonded to the transition metal via a carbon-transition metal bond, and the carbon-transition metal bond may be a coordinate bond. For example, at least one of the m ligands may be a carbaene ligand (e.g., the dopant may be or include Ir(pmp)3, etc.). The transition metal may be, for example, iridium (Ir), platinum (Pt), osmium (Os), palladium (Pd), rhodium (Rh), or gold (Au). The emitting layer and the dopant may be understood by referring to the description of the emitting layer and the dopant provided herein.
[0217]
[0218] In one or more embodiments, the dopant may include a fused-ring compound represented by Formula 1 (e.g., when the content of the host in the emitter layer is greater than the content of the dopant in the emitter layer). For example, a fused-ring compound represented by Formula 1 may be used as a dopant.
[0219] In one embodiment, the emitting layer in the light-emitting device can emit blue light with a maximum emission wavelength in the range of about 390 nanometers (nm) to about 440 nm, but the embodiment is not limited thereto.
[0220] In some implementations...
[0221] The first electrode of the light-emitting device can be the anode.
[0222] The second electrode of the light-emitting device can be a cathode.
[0223] The interlayer may further include a hole transport region between the first electrode and the emitter layer, and an electron transport region between the emitter layer and the second electrode.
[0224] The hole transport region may include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof, and
[0225] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0226] In one or more embodiments, the light-emitting device may include a capping layer located outside the first electrode or the second electrode.
[0227] In one or more embodiments, the light-emitting device may further include at least one of a first capping layer located outside the first electrode and a second capping layer located outside the second electrode, and at least one of the first capping layer and the second capping layer may include a fused-ring compound represented by Formula 1. The first capping layer and the second capping layer can be understood by referring to the description of the first capping layer and the second capping layer provided herein, respectively.
[0228] In some embodiments, the light-emitting device may include:
[0229] A first capping layer located outside the first electrode and comprising a fused ring compound represented by Formula 1;
[0230] Located outside the second electrode and comprising a second capping layer of a fused-ring compound represented by Formula 1; or
[0231] First capping layer and second capping layer (e.g., simultaneously).
[0232] As used herein, the expression “(the interlayer and / or capping layer) comprises at least one fused-ring compound of Formula 1” can be interpreted as meaning that “(the interlayer and / or capping layer) may comprise one (e.g., type or kind) fused-ring compound of Formula 1, or two or more different (e.g., type or kind) fused-ring compounds of Formula 1”.
[0233] For example, the interlayer may include only compound A-1 as a fused-ring compound represented by Formula 1. In this embodiment, compound A-1 may be included in the emitting layer of the light-emitting device. In some embodiments, compounds A-1 and A-2 may be included in the interlayer as fused-ring compounds represented by Formula 1. In this embodiment, compounds A-1 and A-2 may be included in the same layer (e.g., both compounds A-1 and A-2 may be included in the emitting layer simultaneously, for example) or in different layers (e.g., compound A-1 may be included in the emitting layer, and compound A-2 may be included in the electron transport region).
[0234] According to one or more embodiments, the electronic device may include a light-emitting device. The electronic device may further include a thin-film transistor. In some embodiments, the electronic device may further include a thin-film transistor comprising a source electrode and a drain electrode, and a first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode. The electronic device may further include a color filter, a color conversion layer, a touchscreen layer, a polarizing layer, or any combination thereof. The electronic device can be understood by referring to the description of the electronic device provided herein.
[0235] [ Figure 1 [Description]
[0236] Figure 1 This is a schematic diagram of a light-emitting device 10 according to an embodiment. The light-emitting device 10 may include a first electrode 110, a sandwich layer 130, and a second electrode 150.
[0237] The following text will combine Figure 1 The structure of the light-emitting device 10 according to the embodiment and the method of manufacturing the light-emitting device 10 according to the embodiment are described.
[0238] [First Electrode 110]
[0239] exist Figure 1 In this configuration, the substrate may be additionally located below the first electrode 110 and / or above the second electrode 150. The substrate may be a glass substrate and / or a plastic substrate. The substrate may be a flexible substrate comprising a plastic having excellent or suitable heat resistance and / or durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.
[0240] The first electrode 110 can be formed by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, a high work function material that can easily inject holes can be used as the material for the first electrode 110.
[0241] The first electrode 110 may be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In some embodiments, when the first electrode 110 is a semi-transparent electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof may be used as the material for forming the first electrode 110.
[0242] The first electrode 110 may have a single-layer structure consisting of a single layer or a multi-layer structure including two or more layers. In some embodiments, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.
[0243] [Mezzanine 130]
[0244] The interlayer 130 may be on the first electrode 110. The interlayer 130 may include an emitter layer.
[0245] The interlayer 130 may further include a hole transport region between the first electrode 110 and the emitter layer, and an electron transport region between the emitter layer and the second electrode 150.
[0246] In addition to one or more suitable organic materials, the interlayer 130 may further include metal-containing compounds (such as organometallic compounds) and / or inorganic materials (such as quantum dots).
[0247] The interlayer 130 may include: i) at least two emitting units stacked sequentially between the first electrode 110 and the second electrode 150; and ii) a charge generation layer located between the at least two emitting units. When the interlayer 130 includes at least two emitting units and a charge generation layer, the light-emitting device 10 may be a series light-emitting device.
[0248] [Hole transport region in interlayer 130]
[0249] The hole transport region may have i) a single-layer structure comprising a single layer (e.g., composed of a single layer) of a single material (e.g., composed of a single material), ii) a single-layer structure comprising a single layer (e.g., composed of a single layer) of a single material (e.g., composed of a single layer) of a single layer of a single material, or iii) a multi-layer structure having multiple layers of a single material.
[0250] The hole transport region may include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof.
[0251] For example, the hole transport region may have a multi-layer structure, such as a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, wherein the layers of each structure are stacked sequentially on the first electrode 110 in their respective described order.
[0252] The hole transport region may include the compound represented by Formula 201, the compound represented by Formula 202, or any combination thereof:
[0253] Formula 201
[0254]
[0255] Formula 202
[0256]
[0257] Among them, in equations 201 and 202,
[0258] L 201 To L 204 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0259] L 205 It can be *-O-*', *-S-*', or *-N(Q) 201 )-*', unsubstituted or by at least one R 10a Replacement C1-C 20 Alkylene, unsubstituted, or with at least one R 10a Replacement C2-C 20 alkenyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0260] xa1 to xa4 can each be an integer selected from 0 to 5 independently.
[0261] xa5 can be an integer selected from 1 to 10.
[0262] R 201 To R 204 and Q 201 Each can be independently unsubstituted or by at least one R 10aReplacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0263] R 201 and R 202 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form an unsubstituted or substituted compound with at least one R group. 10a Replacement C8-C 60 Polycyclic groups (e.g., carbazole group, etc.) (e.g., compound HT16 described herein),
[0264] R 203 and R 204 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form an unsubstituted or substituted compound with at least one R group. 10a Replacement C8-C 60 Polycyclic groups, and
[0265] na1 can be an integer selected from 1 to 4.
[0266] In some embodiments, formulas 201 and 202 may each include at least one of the groups represented by formulas CY201 to CY217:
[0267]
[0268] In formulas CY201 to CY217, R 10b and R 10c Each can refer to R. 10a To understand from the description, CY 201 To CY 204 Each can be independently C3-C 20 carbonyl group or C1-C 20 Heterocyclic group, and at least one hydrogen in formulas CY201 to CY217 may be unsubstituted or R 10a replace.
[0269] In some embodiments, in formulas CY201 to CY217, the ring CY 201 To CY 204 Each can be independently phenyl, naphthyl, phenanthryl or anthracene.
[0270] In one or more embodiments, Formula 201 and Formula 202 may each include at least one of the groups represented by Formula CY201 to Formula CY203.
[0271] In one or more embodiments, Formula 201 may include at least one of the groups represented by Formulas CY201 to CY203 and at least one of the groups represented by Formulas CY204 to CY217.
[0272] In one or more embodiments, in formula 201, xa1 can be 1, R 201 It can be any group represented by formula CY201 to CY203, xa2 can be 0, and R 202 It can be a group represented by formulas CY204 to CY207.
[0273] In one or more embodiments, Formula 201 and Formula 202 may each exclude groups represented by Formulas CY201 to CY203.
[0274] In one or more embodiments, Formula 201 and Formula 202 may each exclude the groups represented by Formulas CY201 to CY203, and include at least one of the groups represented by Formulas CY204 to CY217.
[0275] In one or more embodiments, Formula 201 and Formula 202 may each exclude groups represented by Formulas CY201 to CY217.
[0276] In some embodiments, the hole transport region may include one of compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), or any combination thereof:
[0277]
[0278]
[0279]
[0280]
[0281]
[0282] The thickness of the hole transport region can be approximately to approximately For example, about to approximately Within the range. When the hole transport region includes a hole injection layer, a hole transport layer, and any combination thereof, the thickness of the hole injection layer can be approximately... to approximately For example, about to approximately Within a certain range, the thickness of the hole transport layer can be approximately to approximately For example, about to approximately Within these ranges, when the thicknesses of the hole transport region, hole injection layer, and hole transport layer are all within these ranges, excellent or adequate hole transport characteristics can be obtained without a significant increase in the driving voltage.
[0283] The emission aid layer can increase light emission efficiency by compensating for the optical resonant distance according to the wavelength of the light emitted by the emission layer. The electron blocking layer prevents or reduces electron leakage from the emission layer into the hole transport region. Materials that may be included in the hole transport region may also be included in both the emission aid layer and the electron blocking layer.
[0284] [p-dopant]
[0285] The hole transport region may include a charge-generating material and the aforementioned materials to improve the conductivity of the hole transport region. The charge-generating material may be substantially uniformly or non-uniformly dispersed in the hole transport region (e.g., as a monolayer composed of charge-generating material).
[0286] Charge-generating materials may include, for example, p-dopers.
[0287] In some implementations, the lowest unoccupied molecular orbital (LUMO) level of the p-dopant may be -3.5 eV or less.
[0288] In some embodiments, the p-doper may include quinone derivatives, cyano-containing compounds, compounds containing elements EL1 and EL2, or any combination thereof.
[0289] Examples of quinone derivatives may include TCNQ and / or F4-TCNQ, etc.
[0290] Examples of cyano-containing compounds may include HAT-CN and / or compounds represented by formula 221, etc.
[0291]
[0292] Equation 221
[0293]
[0294] In Equation 221,
[0295] R 221 To R 223 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, and
[0296] R 221 To R 223 At least one of them can be independently: C3-C replaced by the following 60 carbonyl group or C1-C 60 Heterocyclic groups: cyano; -F; -Cl; -Br; -I; C1-C substituted with cyano, -F, -Cl, -Br, -I or any combination thereof 20 Alkyl groups; or any combination thereof.
[0297] In compounds containing elements EL1 and EL2, element EL1 may be a metal, a metalloid, or a combination thereof, and element EL2 may be a nonmetal, a metalloid, or a combination thereof.
[0298] Examples of metals may include: alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb) and / or cesium (Cs); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr) and / or barium (Ba); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co) Rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag) and / or gold (Au), etc.; later transition metals (e.g., zinc (Zn), indium (In) and / or tin (Sn), etc.); and / or lanthanides (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) and / or lutetium (Lu), etc.), etc.
[0299] Examples of metalloids may include silicon (Si), antimony (Sb), and / or tellurium (Te).
[0300] Examples of nonmetals may include oxygen (O) and / or halogens (e.g., F, Cl, Br, I, etc.).
[0301] For example, compounds containing elements EL1 and EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides and / or metal iodides), quasi-metal halides (e.g., quasi-metal fluorides, quasi-metal chlorides, quasi-metal bromides and / or quasi-metal iodides), metal tellurides, or any combination thereof.
[0302] Examples of metal oxides may include tungsten oxides (e.g., WO, W2O3, WO2, WO3 and / or W2O5, etc.), vanadium oxides (e.g., VO, V2O3, VO2 and / or V2O5, etc.), molybdenum oxides (MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.) and / or rhenium oxides (e.g., ReO3, etc.).
[0303] Examples of metal halides may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and / or lanthanide metal halides.
[0304] Examples of alkali metal halides may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and / or CsI, etc.
[0305] Examples of alkaline earth metal halides may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2 and / or BaI2, etc.
[0306] Examples of transition metal halides may include titanium halides (e.g., TiF4, TiCl4, TiBr4 and / or TiI4, etc.), zirconium halides (e.g., ZrF4, ZrCl4, ZrBr4 and / or ZrI4, etc.), hafnium halides (e.g., HfF4, HfCl4, HfBr4 and / or HfI4, etc.), vanadium halides (e.g., VF3, VCl3, VBr3 and / or VI3, etc.), niobium halides (e.g., NbF3, NbCl3, NbBr3 and / or NbI3, etc.), and tantalum halides (e.g., TaF3, TaCl3, TaBr3, etc.). 3. TaI3, etc.), chromium halides (e.g., CrF3, CrCl3, CrBr3 and / or CrI3, etc.), molybdenum halides (e.g., MoF3, MoCl3, MoBr3, MoI3, etc.), tungsten halides (e.g., WF3, WCl3, WBr3 and / or WI3, etc.), manganese halides (e.g., MnF2, MnCl2, MnBr2 and / or MnI2, etc.), technetium halides (e.g., TcF2, TcCl2, TcBr2 and / or TcI2, etc.), rhenium halides (e.g., ReF2, ReCl2, ReBr2 and / or Re... I2, etc.), iron halides (e.g., FeF2, FeCl2, FeBr2 and / or FeI2, etc.), ruthenium halides (e.g., RuF2, RuCl2, RuBr2 and / or RuI2, etc.), osmium halides (e.g., OsF2, OsCl2, OsBr2 and / or OsI2, etc.), cobalt halides (e.g., CoF2, CoCl2, CoBr2 and / or CoI2, etc.), rhodium halides (e.g., RhF2, RhCl2, RhBr2 and / or RhI2, etc.), iridium halides (e.g., IrF2, IrCl2, IrBr2 and / or IrI2, etc.). IrI2, etc.), nickel halides (e.g., NiF2, NiCl2, NiBr2 and / or NiI2), palladium halides (e.g., PdF2, PdCl2, PdBr2 and / or PdI2), platinum halides (e.g., PtF2, PtCl2, PtBr2 and / or PtI2), copper halides (e.g., CuF, CuCl, CuBr and / or CuI), silver halides (e.g., AgF, AgCl, AgBr and / or AgI) and / or gold halides (e.g., AuF, AuCl, AuBr and / or AuI).
[0307] Examples of post-transition metal halides may include zinc halides (e.g., ZnF2, ZnCl2, ZnBr2 and / or ZnI2, etc.), indium halides (e.g., InI3, etc.) and / or tin halides (e.g., SnI2, etc.).
[0308] Examples of lanthanide metal halides may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3 and / or SmI3, etc.
[0309] Examples of metal halide may include antimony halides (e.g., SbCl5, etc.).
[0310] Examples of metal tellurides may include alkali metal tellurides (e.g., Li₂Te, Na₂Te, K₂Te, Rb₂Te and / or Cs₂Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe and / or BaTe, etc.), and transition metal tellurides (e.g., TiTe₂, ZrTe₂, HfTe₂, V₂Te₃, Nb₂Te₃, Ta₂Te₃, Cr₂Te₃, Mo₂Te₃, W₂Te₃, MnTe, TcTe, ReTe, FeT₂Te). e, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe and / or Au2Te, etc.), post-transition metal tellurides (e.g., ZnTe, etc.) and / or lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe and / or LuTe, etc.).
[0311] [Emitting layer in interlayer 130]
[0312] When the light-emitting device 10 is a full-color light-emitting device, the emitting layer can be patterned as a red emitting layer, a green emitting layer, and / or a blue emitting layer according to the sub-pixels. In one or more embodiments, the emitting layer may have a stacked structure. The stacked structure may include two or more layers selected from red, green, and blue emitting layers. In some embodiments, the two or more layers may be in direct contact with each other. In some embodiments, the two or more layers may be separated from each other. In one or more embodiments, the emitting layer may include two or more materials selected from red, green, and blue emitting materials. The two or more materials may be mixed with each other in a single layer. The two or more materials mixed with each other in a single layer can emit white light.
[0313] The emitting layer may include a host and a dopant. The dopant may be a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
[0314] Based on 100 parts by weight of the host, the amount of dopant in the emitter layer can be from about 0.01 parts by weight to about 15 parts by weight.
[0315] In some implementations, the emission layer may include quantum dots.
[0316] The emission layer may include a delayed fluorescence material. The delayed fluorescence material may be used as a host or dopant in the emission layer.
[0317] The thickness of the emission layer can be approximately to approximately Within the scope, and in some implementations, in approximately to approximately Within these ranges, improved luminescence properties can be obtained without a significant increase in driving voltage when the thickness of the emitting layer is within any of these ranges.
[0318] [main body]
[0319] The main body may include fused ring compounds represented by Formula 1.
[0320] [Phosphorescent dopant]
[0321] Phosphorescent dopants may include at least one transition metal as the center metal.
[0322] Phosphorescent dopants may include monodentate ligands, dipentate ligands, tridentate ligands, tetradentate ligands, pentadentate ligands, hexadentate ligands, or any combination thereof.
[0323] Phosphorescent dopants can be electrically neutral.
[0324] In some embodiments, the phosphorescent dopant may include an organometallic complex represented by formula 401:
[0325] Formula 401
[0326] M(L 401 ) xc1 (L 402 ) xc2 ,
[0327] In Equation 401,
[0328] M can be 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), and / or thulium (Tm)).
[0329] L 401 The ligand can be represented by Equation 402, and xc1 can be 1, 2, or 3, and when xc1 is 2 or greater, at least two L... 401 They can be the same or different from each other.
[0330] Formula 402
[0331]
[0332] L 402 It can be an organic ligand, and c2 can be an integer selected from 0 to 4, and when xc2 is 2 or greater, at least two L... 402 They can be the same or different from each other.
[0333] In Equation 402,
[0334] X 401 and X 402 They can be nitrogen or carbon independently.
[0335] Ring A 401 And Ring A 402 Each can be independently C3-C 60 carbonyl group or C1-C 60 Heterocyclic group,
[0336] T 401 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q) 411 )-*'、*-C(Q 411 (Q) 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 ) = *' or * = C = *',
[0337] X 403 and X 404 Each can be an independent chemical bond (e.g., covalent or coordinate), O, S, N (Q) 413 ), B(Q) 413 ), P(Q 413 ), C(Q 413 (Q) 414 ) or Si(Q 413 (Q) 414 ),
[0338] Q 411 To Q 414 Each can be independently identical to Q1.
[0339] R 401 and R 402 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 20 Alkyl, unsubstituted, or with at least one R 10a Replacement C1-C 20 Alkyl, unsubstituted, or with at least one R 10aReplacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 401 (Q) 402 (Q) 403 -N(Q) 401 (Q) 402 -B(Q) 401 (Q) 402 -C(=O)(Q) 401 -S(=O)2(Q) 401 ) or -P(=O)(Q 401 (Q) 402 ),
[0340] Q 401 To Q 403 Each can be independently identical to Q1.
[0341] xc11 and xc12 can each be an integer selected from 0 to 10 independently, and
[0342] In Equation 402, * and *' each indicate the binding site with M in Equation 401.
[0343] In one or more embodiments, in formula 402, i)X 401 It can be nitrogen, and X 402 It can be carbon, or ii)X 401 and X 402 They can all be nitrogen (e.g., simultaneously).
[0344] In one or more embodiments, when xc1 in equation 401 is 2 or greater, at least two L 401 The two rings A in 401 Optionally via T as a linking group 402 Combined, or two rings A 402 Optionally via T as a linking group 403 (See compounds PD1 through PD4 and PD7). T 402 and T 403 Each can be independently associated with T 401 same.
[0345] L in Equation 401 402 It can be any suitable organic ligand. For example, L 402 It can be a halogen group, a diketone group (e.g., an acetylacetone group), a carboxylic acid group (e.g., a pyridine carboxylic acid group), -C (=O), an isonitrile group, -CN, or a phosphorus-containing group (e.g., a phosphine group or a phosphite group).
[0346] The phosphorescent dopant may be, for example, one of compounds PD1 to PD25 or any combination thereof:
[0347]
[0348] [Fluorescent dopant]
[0349] Fluorescent dopants may include amine-containing compounds, styrene-containing compounds, or any combination thereof.
[0350] In some embodiments, the fluorescent dopant may include a compound represented by formula 501:
[0351] Formula 501
[0352]
[0353] In Equation 501,
[0354] Ar 501 L 501 To L 503 R 501 and R 502 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0355] xd1 to xd3 can each be independently 0, 1, 2, or 3, and
[0356] xd4 can be 1, 2, 3, 4, 5 or 6.
[0357] In some implementations, in formula 501, Ar 501 It may include a fused ring group in which at least three monocyclic groups are fused (e.g., anthracene, 1,2-benzophenanthrene or pyrene).
[0358] In some implementations, xd4 in Equation 501 can be 2.
[0359] In some embodiments, the fluorescent dopant may include one of compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof:
[0360]
[0361]
[0362]
[0363] [Delayed fluorescence materials]
[0364] The emission layer may include a delayed fluorescence material.
[0365] The delayed fluorescence material described herein can be any suitable compound that can emit delayed fluorescence according to the delayed fluorescence emission mechanism.
[0366] The delayed fluorescence material included in the emission layer can be used as a host or a dopant, depending on the type (variety) of other materials included in the emission layer.
[0367] In some embodiments, the difference between the triplet energy level (eV) and the singlet energy level (eV) of the delayed fluorescent material can be about 0 eV or greater and about 0.5 eV or less. When the difference between the triplet energy level (eV) and the singlet energy level (eV) of the delayed fluorescent material is within this range, the upconversion from the triplet state to the singlet state of the delayed fluorescent material can occur efficiently (e.g., with high efficiency), thus improving the luminous efficiency of the light-emitting device 10, etc.
[0368] In some embodiments, the delayed fluorescence material may include: i) at least one electron donor (e.g., a π-electron-rich C3-C 60 Cyclic groups, such as carbazole groups, and at least one electron acceptor (e.g., sulfoxide, cyano, π-electron-deficient nitrogen-containing C1-C groups). 60 Materials containing cyclic groups, etc., and / or ii) including C8-C alloys containing at least two cyclic groups fused together and sharing boron (B). 60 Materials with polycyclic groups, etc.
[0369] Examples of delayed fluorescence materials may include at least one of compounds DF1 to DF9:
[0370]
[0371]
[0372] [Quantum dot]
[0373] The emission layer may include quantum dots.
[0374] As used herein, the term "quantum dot" refers to a crystal of a semiconductor compound and may include any suitable material capable of emitting one or more appropriate emission wavelengths of light depending on the size of the crystal.
[0375] The diameter of quantum dots can be, for example, in the range of about 1 nm to about 10 nm.
[0376] Quantum dots can be synthesized through wet chemical processes, metal-organic chemical vapor deposition, molecular beam epitaxy, or any similar process.
[0377] Wet chemistry processes are methods for growing quantum dot crystals by mixing precursor materials with organic solvents. During crystal growth, the organic solvent naturally acts as a dispersant on the surface of the quantum dot crystals and controls their growth. Therefore, wet chemistry processes are easier to perform than vapor deposition processes (such as metal-organic chemical vapor deposition (MOCVD) and / or molecular beam epitaxy (MBE)). Furthermore, the growth of quantum dot particles can be controlled or selected at a lower manufacturing cost.
[0378] Quantum dots may include group II-VI semiconductor compounds; group III-V semiconductor compounds; group III-VI semiconductor compounds; group I-III-VI semiconductor compounds; group IV-VI semiconductor compounds; group IV elements or compounds; or any combination thereof.
[0379] Examples of group II-VI semiconductor compounds may include: binary compounds (such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe and / or MgS); ternary compounds (such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnS, CdZnS, CdSeTe ... nSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe and / or MgZnS); quaternary compounds (such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and / or HgZnSTe); or any combination thereof.
[0380] Examples of Group III-V semiconductor compounds may include binary compounds (such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, and / or InSb); ternary compounds (such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAIP, InNAs, InNSb, InPAs, and / or InPSb); quaternary compounds (such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and / or InAlPSb); or any combination thereof. In some embodiments, the Group III-V semiconductor compounds may further include Group II elements. Examples of group III-V semiconductor compounds that further include group II elements may include InZnP, InGaZnP, and / or InAlZnP, etc.
[0381] Examples of group III-VI semiconductor compounds may include binary compounds (such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3 and / or InTe, etc.); ternary compounds (such as InGaS3 and / or InGaSe3, etc.); or any combination thereof.
[0382] Examples of semiconductor compounds of the I-III-VI may include ternary compounds (such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, AgAlO2, or any combination thereof).
[0383] Examples of group IV-VI semiconductor compounds may include binary compounds (such as SnS, SnSe, SnTe, PbS, PbSe and / or PbTe); ternary compounds (such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe and / or SnPbTe); quaternary compounds (such as SnPbSSe, SnPbSeTe and / or SnPbSTe); or any combination thereof.
[0384] Group IV elements or compounds can be single-element materials (such as Si and / or Ge); binary compounds (such as SiC and / or SiGe); or any combination thereof.
[0385] The single element included in multi-element compounds (such as binary, ternary and / or quaternary compounds) may exist in its particles in substantially uniform or non-uniform concentrations.
[0386] Quantum dots can have a single structure (including a spatially substantially uniform concentration of each element in the quantum dot) or a core-shell dual structure (e.g., including a concentration of each element in the quantum dot that varies between the core and the shell). In some embodiments, the material included in the core may be different from the material included in the shell.
[0387] The shell of a quantum dot can serve as a protective layer to prevent or reduce chemical denaturation of the nucleus to maintain semiconductor properties, and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be single-layered or multi-layered. The interface between the nucleus and the shell can have a concentration gradient in which the concentration of elements present in the shell decreases towards the nucleus.
[0388] Examples of shells for quantum dots include metal, quasi-metallic, or non-metallic oxides, semiconductor compounds, or combinations thereof. Examples of metal, quasi-metallic, or non-metallic oxides may include: binary compounds (such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and / or NiO); ternary compounds (such as MgAl2O4, CoFe2O4, NiFe2O4, and / or CoMn2O4); and any combinations thereof. Examples of semiconductor compounds may include group II-VI semiconductor compounds; group III-V semiconductor compounds; group III-VI semiconductor compounds; group I-III-VI semiconductor compounds; group IV-VI semiconductor compounds; or any combinations thereof. In some embodiments, the semiconductor compound may be CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
[0389] Quantum dots can have a full width at half maximum (FWHM) of a spectrum with emission wavelengths of about 45 nm or less, about 40 nm or less, or about 30 nm or less. When the FWHM of a quantum dot is within this range, color purity or color reproducibility can be improved. In some embodiments, because light emitted through a quantum dot is emitted in all directions, optical viewing angles can be improved.
[0390] In some implementations, quantum dots may be spherical, conical, multi-armed or cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanosheets.
[0391] By adjusting the size of the quantum dots, the band gap can also be adjusted, thereby obtaining one or more suitable wavelengths of light in the quantum dot emitting layer. By utilizing quantum dots of various suitable sizes, light-emitting devices capable of emitting light of various suitable wavelengths can be realized. In some embodiments, the size of the quantum dots can be selected so that they can emit red, green, and / or blue light. In some embodiments, the size of the quantum dots can be selected so that they can emit white light by combining one or more suitable light colors.
[0392] [Electron transport region in interlayer 130]
[0393] The electron transport region may have i) a single-layer structure comprising a single layer (e.g., composed of a single layer) of a single material (e.g., composed of a single material), ii) a single-layer structure comprising a single layer (e.g., composed of a single layer) of a single material (e.g., composed of a single layer) of a single layer of a single material, or iii) a multilayer structure having multiple layers of a single material.
[0394] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0395] In some embodiments, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the layers of each structure are stacked sequentially on the emitter layer in their respective described order.
[0396] Electron transport regions (e.g., buffer layers, hole blocking layers, electron control layers, or electron transport layers within electron transport regions) may include metal-free compounds comprising at least one π-electron-deficient nitrogen-containing C1-C. 60 Cyclic groups.
[0397] In some embodiments, the electron transport region may include a compound represented by formula 601:
[0398] Formula 601
[0399] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 ,
[0400] In Equation 601,
[0401] Ar 601 and L 601 Each can be independently unsubstituted or by at least one R 10aReplacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0402] xe11 can be 1, 2, or 3.
[0403] xe1 can be 0, 1, 2, 3, 4, or 5.
[0404] R 601 It can be unsubstituted or by at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q) 601 ) or -P(=O)(Q 601 (Q) 602 ),
[0405] Q 601 To Q 603 Each can be independently identical to Q1.
[0406] xe21 can be 1, 2, 3, 4, or 5, and
[0407] Ar 601 L 601 and R 601 At least one of them can be independently unsubstituted or by at least one R. 10a Substituted π-electron-deficient nitrogen-containing C1-C 60 Cyclic groups.
[0408] In some implementations, when xe11 in formula 601 is 2 or greater, at least two Ar 601 It can be linked via a single bond.
[0409] In some implementations, in formula 601, Ar 601 It can be a substituted or unsubstituted anthracene group.
[0410] In some embodiments, the electron transport region may include a compound represented by formula 601-1:
[0411] Formula 601-1
[0412]
[0413] In Equation 601-1,
[0414] X 614 It can be N or C(R) 614 ), X 615 It can be N or C(R) 615 ), X 616 It can be N or C(R) 616 ), selected from X 614 To X 616 At least one of them can be N,
[0415] L 611 To L 613 Each can be independently associated with L 601 same,
[0416] xe611 to xe613 can each be independently identical to xe1.
[0417] R 611 To R 613 Each can be independently associated with R 601 Same, and
[0418] R 614 To R 616 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group.
[0419] For example, in Equations 601 and 601-1, xe1 and xe611 to xe613 can each be 0, 1 or 2 independently.
[0420] The electron transport region may include one of compounds ET1 to ET45, 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:
[0421]
[0422]
[0423]
[0424] The thickness of the electron transport region can be approximately to approximately For example, about to approximately Within the range. When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, hole blocking layer, or electron control layer can each be independently within approximately [a certain range]. to approximately For example, about to approximately Within a certain range, and the thickness of the electron transport layer can be approximately... to approximately For example, about to approximately Within these ranges, when the thicknesses of the buffer layer, hole blocking layer, electron control layer, electron transport layer, and / or electron transport region are each within these ranges, excellent or adequate electron transport characteristics can be obtained without a significant increase in the driving voltage.
[0425] In addition to the materials mentioned above, the electron transport region (e.g., the electron transport layer in the electron transport region) may further include a metallic material.
[0426] Metal-containing materials may include alkali metal complexes, alkaline earth metal complexes, or any combination thereof. The metal ions in alkali metal complexes may be lithium (Li) ions, sodium (Na) ions, potassium (K) ions, rubidium (Rb) ions, or cesium (Cs) ions. The metal ions in alkaline earth metal complexes may be beryllium (Be) ions, magnesium (Mg) ions, calcium (Ca) ions, strontium (Sr) ions, or barium (Ba) ions. Each ligand coordinated to the metal ions of the alkali metal complex and alkaline earth metal complex may independently be hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, cyclopentadiene, or any combination thereof.
[0427] For example, metallic materials may include Li complexes. Li complexes may include, for example, compounds ET-D1(Liq) or ET-D2:
[0428]
[0429] The electron transport region may include an electron injection layer to facilitate the injection of electrons from the second electrode 150. The electron injection layer may be in direct contact with the second electrode 150.
[0430] The electron injection layer may have i) a single-layer structure including a single layer (for example, consisting of a single layer), wherein the single layer includes a single material (for example, consisting of a single material), ii) a single-layer structure including a single layer (for example, consisting of a single layer), wherein the single layer includes a plurality of different materials, or iii) a multilayer structure having a plurality of layers, wherein the plurality of layers include a plurality of different materials.
[0431] The electron injection layer may include alkali metals, alkaline earth metals, rare earth metals, alkali metal-containing compounds, alkaline earth metal-containing compounds, rare earth metal-containing compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof.
[0432] The alkali metal may be lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), or any combination thereof. The alkaline earth metal may be magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), or any combination thereof. The rare earth metal may be scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb), gadolinium (Gd), or any combination thereof.
[0433] The alkali metal-containing compound, the alkaline earth metal-containing compound and the rare earth metal-containing compound may each independently be one or more oxides, one or more halides (for example, fluoride, chloride, bromide or iodide), one or more tellurides of each of the alkali metal, the alkaline earth metal and the rare earth metal, or any combination thereof.
[0434] The alkali metal-containing compound may be one or more alkali metal oxides (such as Li2O, Cs2O and / or K2O), one or more alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI and / or KI), or any combination thereof. The alkaline earth metal-containing compound may include one or more alkaline earth metal oxides (such as BaO, SrO, CaO, Ba x Sr 1-x O (wherein x is a real number satisfying 0<x<1) and / or Ba x Ca 1-xO (wherein 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. In some embodiments, the rare earth metal-containing compound may include lanthanide metal tellurides. Examples of lanthanide metal tellurides may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3 and / or Lu2Te3, etc.
[0435] Alkali metal complexes, alkaline earth metal complexes and rare earth metal complexes may include: i) metal ions of alkali metals, alkaline earth metals and rare earth metals as respectively described above, and ii) ligands bonded to the metal ions, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0436] The electron injection layer may include (e.g., consist of) alkali metals, alkaline earth metals, rare earth metals, alkali metal-containing compounds, alkaline earth metal-containing compounds, rare earth metal-containing compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof as described above. In some embodiments, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).
[0437] In some embodiments, the electron injection layer may include (e.g., consist of) i) an alkali metal-containing compound (e.g., an alkali metal halide); or ii) 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. In some embodiments, the electron injection layer may be a KI:Yb co-deposited layer and / or a RbI:Yb co-deposited layer, etc.
[0438] When the electron injection layer further includes an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkaline earth metal-containing compound, rare earth metal-containing compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof may be substantially uniformly or non-uniformly dispersed in a matrix including the organic material.
[0439] The thickness of the electron injection layer can be approximately to approximately Within the scope, and in some implementations, in approximately to approximately Within these ranges, excellent or adequate electron injection characteristics can be obtained without a significant increase in driving voltage when the thickness of the electron injection layer is within any of these ranges.
[0440] [Second electrode 150]
[0441] The second electrode 150 may be located on the interlayer 130. In one embodiment, the second electrode 150 may serve as a cathode, acting as an electron injection electrode. In this embodiment, the material used to form the second electrode 150 may be a material with a low work function, such as a metal, alloy, conductive compound, or any combination thereof.
[0442] 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 transmission electrode, a semi-transmission electrode, or a reflection electrode.
[0443] The second electrode 150 may have a single-layer structure or a multi-layer structure comprising two or more layers.
[0444] [Capping layer]
[0445] The first capping layer may be located outside the first electrode 110, and / or the second capping layer may be located outside the second electrode 150. In some embodiments, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are stacked sequentially in the order described herein, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked sequentially in the order described herein, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked sequentially in the order described herein.
[0446] In the light-emitting device 10, light emitted from the emitting layer in the interlayer 130 can pass through the first electrode 110 (which may be a semi-transparent electrode or a transmissive electrode) and through the first capping layer to reach the outside. In the light-emitting device 10, light emitted from the emitting layer in the interlayer 130 can pass through the second electrode 150 (which may be a semi-transparent electrode or a transmissive electrode) and through the second capping layer to reach the outside.
[0447] Based on the principle of constructive interference, the first and second capping layers can improve the external luminescence efficiency. Therefore, the optical extraction efficiency of the light-emitting device 10 can be increased, thereby improving the luminescence efficiency of the light-emitting device 10.
[0448] The first and second capping layers may each comprise a material having a refractive index of 1.6 or higher (at 589 nm).
[0449] The first capping layer and the second capping layer can each be independently a capping layer including organic materials, an inorganic capping layer including inorganic materials, or an organic-inorganic composite capping layer including both organic and inorganic materials.
[0450] At least one of the first and second capping layers may independently comprise a carbocyclic compound, a heterocyclic compound, an amino-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthyl phthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, heterocyclic compound, and amino-containing compound may optionally be substituted with substituents containing oxygen (O), nitrogen (N), sulfur (S), selenium (Se), silicon (Si), fluorine (F), chlorine (Cl), bromine (Br), iodine (I), or any combination thereof. In some embodiments, at least one of the first and second capping layers may independently comprise an amino-containing compound.
[0451] In some embodiments, at least one of the first capping layer and the second capping layer may each independently comprise a compound represented by formula 201, a compound represented by formula 202, or any combination thereof.
[0452] In one or more embodiments, at least one of the first capping layer and the second capping layer may each independently comprise one of compounds HT28 to HT33, one of compounds CP1 to CP6, β-NPB, or any combination thereof:
[0453]
[0454] [membrane]
[0455] The fused-ring compound represented by Formula 1 may be included in one or more suitable films. According to one or more embodiments, films comprising the fused-ring compound represented by Formula 1 may be provided. The film may be, or serve as, for example, an optical component (or, a light control component) (e.g., a color filter, a color conversion component, a capping layer, a light extraction efficiency improvement layer, a selective light absorption layer, a polarizing layer, and / or a content dot layer, etc.), a light-blocking component (e.g., a light-reflecting layer or a light-absorbing layer), or a protective component (e.g., an insulating layer or a dielectric material layer).
[0456] [Electronic Devices]
[0457] The light-emitting device may be included in one or more suitable electronic devices. In some embodiments, the electronic device including the light-emitting device may be a light-emitting device or an authentication device.
[0458] In addition to the light-emitting device, the electronic device (e.g., the light-emitting device) may further include i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and / or color conversion layer may be disposed in at least one direction of travel of the light emitted from the light-emitting device. For example, the light emitted from the light-emitting device may be blue light or white light. The light-emitting device can be understood by referring to the description provided herein. In some embodiments, the color conversion layer may include quantum dots. The quantum dots may be, for example, the quantum dots described herein.
[0459] An electronic device may include a first substrate. The first substrate may include a plurality of sub-pixel regions, a color filter may include a plurality of color filter regions corresponding to the plurality of sub-pixel regions, and a color conversion layer may include a plurality of color conversion regions corresponding to the plurality of sub-pixel regions.
[0460] A pixel-defining film can be located between multiple sub-pixel regions to define each sub-pixel region.
[0461] The color filter may further include a plurality of color filter regions and a light-blocking pattern between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light-blocking pattern between the plurality of color conversion regions.
[0462] Multiple color filter regions (or multiple 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, wherein the first color light, the second color light, and / or the third color light may have different maximum emission wavelengths. In some embodiments, 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. In some embodiments, each of the multiple color filter regions (or multiple color conversion regions) may include a quantum dot. In some embodiments, the first region may include a red quantum dot, the second region may include a green quantum dot, and the third region may not include a quantum dot. Quantum dots can be understood by referring to the description of quantum dots provided herein. The first region, the second region, and / or the third region may each further include a scatterer.
[0463] In some embodiments, the light-emitting device can emit a first light, a first region can absorb the first light to emit 1-1 color light, a second region can absorb the first light to emit 2-1 color light, and a third region can absorb the first light to emit 3-1 color light (e.g., by transmitting or absorbing and emitting the first light as 3-1 color light). In this embodiment, the 1-1 color light, the 2-1 color light, and the 3-1 color light can each have a different maximum emission wavelength. In some embodiments, the first light can be blue light, the 1-1 color light can be red light, the 2-1 color light can be green light, and the 3-1 color light can be blue light.
[0464] In addition to the light-emitting device, the electronic device may further include a thin-film transistor. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, wherein 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 device.
[0465] Thin-film transistors may further include gate electrodes and / or gate insulating films, etc.
[0466] The active layer may include crystalline silicon, amorphous silicon, organic semiconductors and / or oxide semiconductors.
[0467] The electronic device may further include an encapsulation unit for sealing the light-emitting device. The encapsulation unit may be located between the color filter and / or color conversion layer and the light-emitting device. The encapsulation unit allows light to pass from the light-emitting device to the outside while (e.g., synchronously) preventing or reducing the penetration of air and moisture into the light-emitting device. The encapsulation unit may be a sealing substrate comprising a transparent glass and / or a plastic substrate. The encapsulation unit may be a thin-film encapsulation layer comprising at least one of an organic layer and an inorganic layer. When the encapsulation unit is a thin-film encapsulation layer, the electronic device may be flexible.
[0468] In addition to color filters and / or color conversion layers, one or more suitable functional layers may be disposed on the package unit, depending on the intended use of the electronic device. Examples of functional layers may include a touchscreen layer and / or a polarization layer, etc. The touchscreen layer may be a resistive touchscreen layer, a capacitive touchscreen layer, or an infrared beam touchscreen layer. The authentication device may be, for example, a biometric authentication device that identifies an individual based on biometric information (e.g., fingertip and / or pupil, etc.).
[0469] In addition to the aforementioned light-emitting device, the certification equipment may further include a bioassay information collection unit.
[0470] Electronic devices may be suitable for one or more suitable displays, light sources, lighting, personal computers (e.g., mobile personal computers), cellular phones, digital cameras, electronic notebooks, electronic dictionaries, video game consoles, medical devices (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram recorders, ultrasound diagnostic devices, or endoscopic display devices), fish finders, one or more suitable measuring devices, instruments (e.g., instruments for automobiles, airplanes, and / or ships), and / or projectors.
[0471] [ Figure 2 and Figure 3 [Description]
[0472] Figure 2 This is a schematic cross-sectional view of a light-emitting device according to an embodiment.
[0473] Figure 2 The light-emitting device may include a substrate 100, a thin-film transistor, a light-emitting device, and a packaging unit 300 that seals the light-emitting device.
[0474] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be on the substrate 100. The buffer layer 210 prevents or reduces the penetration of impurities into the substrate 100 and provides a flat surface on the substrate 100.
[0475] The thin-film transistor may be on the buffer layer 210. The thin-film transistor may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
[0476] The active layer 220 may include inorganic semiconductors (such as silicon and / or polysilicon), organic semiconductors or oxide semiconductors, and includes a source region, a drain region and a channel region.
[0477] A gate insulating film 230 for insulating the active layer 220 and the gate electrode 240 may be on the active layer 220, and the gate electrode 240 may be on the gate insulating film 230.
[0478] The interlayer insulating film 250 may be on the gate electrode 240. The interlayer insulating film 250 may be between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to provide insulation between them.
[0479] The source electrode 260 and the drain electrode 270 may be 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 adjacent to the exposed source region and the exposed drain region of the active layer 220.
[0480] This thin-film transistor can be electrically connected to a light-emitting device to drive the light-emitting device, and can be 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 device may be on the passivation layer 280. The light-emitting device may include a first electrode 110, a sandwich layer 130, and a second electrode 150.
[0481] The first electrode 110 may be on the passivation layer 280. The passivation layer 280 may not completely cover the drain electrode 270, and may expose a specific area of the drain electrode 270, and the first electrode 110 may be configured to connect to the exposed area of the drain electrode 270.
[0482] Pixel defining film 290 may be on first electrode 110. Pixel defining film 290 may expose a defined area or predetermined area of first electrode 110, and interlayer 130 may be formed in the exposed area of first electrode 110. Pixel defining film 290 may be a polyimide or polyacrylic acid organic film. In some embodiments, some higher layers of interlayer 130 may extend to the upper portion of pixel defining film 290 and may be provided as common layers.
[0483] The second electrode 150 may be on the interlayer 130, and the 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.
[0484] The encapsulation unit 300 may be on the capping layer 170. The encapsulation unit 300 may be on the light-emitting device to protect it from moisture and / or oxygen. The encapsulation unit 300 may include an inorganic film, which may include silicon nitride (SiN). x ), silicon dioxide (SiO) x Indium tin oxide, indium zinc oxide, or any combination thereof; organic membranes, including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resins (e.g., polymethyl methacrylate and / or polyacrylic acid), epoxy resins (e.g., aliphatic glycidyl ether (AGE)), or any combination thereof; or combinations of inorganic and organic membranes.
[0485] Figure 3 This is a schematic cross-sectional view of a light-emitting device according to another embodiment.
[0486] Figure 3 The light-emitting device shown can be used with Figure 2 The light-emitting devices shown are substantially similar (e.g., identical), except that the light-shielding pattern 500 and functional region 400 may additionally be located on 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. In some embodiments, Figure 3 The light-emitting devices shown may be cascaded light-emitting devices.
[0487] [Manufacturing Method]
[0488] The layers constituting the hole transport region, the emission layer, and the electron transport region can each be formed in a designated or predetermined region using one or more suitable methods (such as vacuum deposition, spin coating, casting, Langmuir-Brookett (LB) deposition, inkjet printing, laser printing, and / or laser-induced thermal imaging).
[0489] When the layers constituting the hole transport region, the emitter layer, and the electron transport region are formed independently by vacuum deposition, the vacuum deposition can be performed at a deposition temperature ranging from about 100°C to about 500°C, and at a deposition temperature of about 10°C. -8 To about 10 -3 The vacuum level within the range of Torr and at approximately 0.01 angstroms per second ( ( / second) to approximately The deposition is carried out at a rate in the range of / second, depending on the material to be included in each layer and the structure of each layer to be formed.
[0490] [General Definition of the Terminology]
[0491] As used in this article, the term "C3-C" 60 "Carbocyclic group" refers to a cyclic group consisting only of carbon atoms, with 3 to 60 carbon atoms as cyclic atoms. For example, the term "C1-C" as used herein... 60 A "heterocyclic group" refers to a cyclic group having 1 to 60 carbon atoms in addition to the heteroatom that forms the ring (other than carbon atoms). (C3-C) 60 Carbocyclic groups and C1-C 60 Heterocyclic groups can each be a monocyclic group consisting of one ring or a polycyclic group in which at least two rings are fused. For example, C1-C 60 The number of cyclic atoms in a heterocyclic group can range from 3 to 61.
[0492] As used herein, the term "cyclic group" may include C3-C 60 Carbocyclic groups and C1-C 60 Heterocyclic group.
[0493] The term "π-electron-rich C3-C" 60 "Cyclic group" refers to a cyclic group having 3 to 60 carbon atoms and excluding (e.g., precluding) *-N=*' as a cyclic moiety. The term "π-electron-deficient nitrogen-containing C1-C" is also used herein. 60 "Cyclic group" refers to a heterocyclic group having 1 to 60 carbon atoms and *-N=*' as the cyclic part.
[0494] In some implementations...
[0495] C3-C 60 The carbocyclic group may be i) a T1 group (as defined below) or ii) a group in which at least two T1 groups are fused together (e.g., cyclopentadienyl, adamantyl, norbornel, phenyl, pentaenyl, naphthyl, azuleyl, indaryl, acenaphthenic, phenanthyl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenantyl, peryl, penfenyl, heptaenyl, tetraphenyl, framyl, hexaphenyl, pentaphenyl, rubidyl, keratyl, ovoleyl, indole, fluorenyl, spiro-difluorenyl, benzofluorenyl, indolephenyl or indoleanthryl).
[0496] C1-C 60 The heterocyclic group may be i) a T2 group (as defined below), ii) a group in which at least two T2 groups are fused, or iii) a group in which at least one T2 group is fused with at least one T1 group (e.g., pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, naphthoisoindole, benzothiophene, benzofuranyl, carbazole, dibenzothiophene, dibenzothiophene, dibenzofuranyl, indocarbazole, indolecarbazole, benzofuranocarbazole, benzothiophenecarbazole, benzothiophenecarbazole, benzoindocarbazole, benzocarbazole, benzonaphthofuranyl, benzonaphthophene, benzonaphthothiophene, benzofuranodibenzofuranyl, benzofuranyl Benzethienyl, benzothienylbenzyl, pyrazolyl, imidazole, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, benzopyrazolyl, benzimidazolyl, benzooxazolyl, benzisooxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzyl (e.g., benzo[i]isoquinolinyl, quinoxalinyl, benzo[i]quinoxalinyl, quinazolinyl, benzo[i]quinazolinyl, phenanthrolinyl, cenolinyl, phthalazinyl, naphthidyl, imidazo[i]pyridinyl, imidazo[i]pyrimidinyl, imidazo[i]triazinyl, imidazo[i]pyrazinyl, imidazo[i]pyridazinyl, azacarbazoyl, azafluorenyl, azadibenzothiophene, azadibenzofuranyl, etc.)
[0497] C3-C rich in π electrons 60 The cyclic group may be i) a T1 group, ii) a fused group in which at least two T1 groups are fused, iii) a T3 group (as defined below), iv) a fused group in which at least two T3 groups are fused, or v) a fused group in which at least one T3 group is fused with at least one T1 group (e.g., C3-C). 60Carbocyclic, 1H-pyrrole, thiorrole, borocyclopentadienyl, 2H-pyrrole, 3H-pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, naphthoisoindole, benzothiorrole, benzothiophene, benzofuranyl, carbazole, dibenzothiorrole, dibenzothiophene, dibenzofuranyl, indole-carbazole, benzofuran-carbazole, benzothiophene-carbazole, benzothiorrole-carbazole, benzoindole-carbazole, benzocarbazole, benzonaphthofuranyl, benzonaphthophene, benzonaphthorrole, benzofuran-dibenzofuranyl, benzofuran-dibenzothiophene, benzothiophene-dibenzothiophene, etc.), and
[0498] Nitrogen-containing C1-C lacking π electrons 60 The cyclic group may be i) a T4 group (as defined below), ii) a group in which at least two T4 groups are fused, iii) a group in which at least one T4 group is fused with at least one T1 group, iv) a group in which at least one T4 group is fused with at least one T3 group, or v) a group in which at least one T4 group, at least one T1 group, and at least one T3 group are fused (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazole). The following groups are listed: benzoxazolyl, benzoisoxazolyl, benzothiazolyl, benzoisothiazolyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinel, cenolinyl, phthalazinyl, naphthidyl, imidazopyridyl, imidazopyrimidyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiophene, azadibenzothiophene, and azadibenzofuranyl, etc.
[0499] The T1 group can be cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornane (or bicyclo[2.2.1]heptane)yl, norbornenyl, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane, or phenyl.
[0500] The T2 group can be furanyl, thiophene, 1H-pyrrolyl, thiophene, borocyclopentadienyl, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathiazolyl, azaboracyclopentadienyl, pyridinyl, pyrimidinyl, pyrazinyl, pyrazinyl, triazinyl, tetraazinyl, pyrrolylalkyl, imidazolyl, dihydropyrrolyl, piperidinyl, tetrahydropyridinyl, dihydropyridinyl, hexahydropyrimidinyl, tetrahydropyrimidinyl, dihydropyrimidinyl, piperazinyl, tetrahydropyrazinyl, dihydropyrazinyl, tetrahydropyrazinyl, or dihydropyrazinyl.
[0501] The T3 group can be furanyl, thiophene, 1H-pyrrole, thiophene, or borocyclopentadienyl, and
[0502] The T4 group can be 2H-pyrrole, 3H-pyrrole, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, azirthiolyl, aziboranecyclopentadienyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, or tetraazinyl.
[0503] As used in this article, the terms "cyclic group" and "C3-C" are similar to those used in this article. 60 "Carbocyclic group", "C1-C" 60 Heterocyclic groups, π-electron-rich C3-C 60 "Cyclic groups" or "nitrogen-containing C1-C groups lacking π electrons" 60 "Cyclic group" can be a group fused with any suitable cyclic group, monovalent group, or polyvalent group (e.g., divalent, trivalent, and / or tetravalent group, etc.), depending on the structure of the formula to which the term is applied. For example, "phenyl" can be a benzene ring, phenyl, and / or phenylene, etc., and this can be understood by those skilled in the art based on the structure of formulas including "phenyl".
[0504] Unit price C3-C 60 Carbocyclic groups and monovalent C1-C 60 Examples of heterocyclic groups may include C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups. Divalent C3-C 60 Carbocyclic groups and divalent C1-C 60 Examples of heterocyclic groups may include C3-C 10 Cycloalkylene, C1-C 10 Heterocyclic alkyl, C3-C10 Cycloalkylene, C1-C 10 Heterocyclic alkenyl, C6-C 60 aryl, C1-C 60 Hypoaryl, divalent non-aromatic fused polycyclic groups and divalent non-aromatic fused heterocyclic groups.
[0505] As used in this article, the term "C1-C" 60 "Alkyl" refers to a monovalent group in a straight-chain or branched aliphatic hydrocarbon having 1 to 60 carbon atoms, for example, C1-C64. 20 Alkyl or C1-C 10 Alkyl groups, and examples thereof may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, and / or tert-decyl. As used herein, the term "C1-C" is... 60 "alkylene" refers to C1-C 60 Alkyl groups have essentially the same structure as divalent groups.
[0506] As used in this article, the term "C2-C" 60 "Alkenyl" refers to the group formed at C2-C. 60 An alkyl group having at least one carbon-carbon double bond at its middle or end. Examples include vinyl, propenyl, and / or butenyl groups. As used herein, the term "C2-C" is used... 60 "Alkenyl" refers to C2-C 60 Alkenes are divalent groups with essentially the same structure.
[0507] As used in this article, the term "C2-C" 60 "Alkyne group" refers to the group at C2-C 60 The alkyl group has at least one carbon-carbon triple bond at its middle or end. Examples may include ethynyl and / or propynyl groups. As used herein, the term "C2-C" is used... 60 "Immyneyl" refers to C2-C 60 Alkynes are divalent groups with essentially the same structure.
[0508] As used in this article, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 Alkyl groups, for example, C1-C 20 Alkoxy or C1-C 10 Alkyl groups. Examples include methoxy, ethoxy, and isopropoxy groups.
[0509] As used in this article, the term "C3-C" 10 "Cycloalkyl" refers to a monocyclic cyclic group consisting of 3 to 10 carbon atoms in a monovalent saturated hydrocarbon. For example, the C3-C group used in this article... 10 Examples of cycloalkyl groups may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornelyl (bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, and / or bicyclo[2.2.2]octyl. As used herein, the term "C3-C" may also be used. 10 "Cycloalkylene" refers to C3-C 10 Cycloalkyl groups have divalent groups with essentially the same structure.
[0510] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent cyclic group comprising at least one heteroatom other than a carbon atom as a cyclic atom and having 1 to 10 carbon atoms. Examples may include 1,2,3,4-oxatriazolyl, tetrahydrofuranyl, and / or tetrahydrothiophenyl. The term "C1-C" as used herein... 10 "Heterocyclic alkyl" refers to C1-C 10 Heterocyclic alkyl groups have divalent groups with essentially the same structure.
[0511] As used in this article, the term "C3-C" 10 "Cycloalkenyl" refers to a monovalent cyclic group having 3 to 10 carbon atoms, at least one carbon-carbon double bond in its ring, and not being aromatic. Examples include cyclopentenyl, cyclohexenyl, and / or cycloheptenyl. As used herein, the term "C3-C" is also relevant. 10 "Biopylene" refers to C3-C 10 Cycloalkenyl groups are divalent groups with essentially the same structure.
[0512] As used in this article, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent cyclic group comprising at least one heteroatom other than a carbon atom as a cyclic atom, having 1 to 10 carbon atoms, and having at least one double bond in its ring. C1-C 10 Examples of heterocyclic alkenyl groups may include 4,5-dihydro-1,2,3,4-oxarizolyl, 2,3-dihydrofuranyl, and / or 2,3-dihydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkyl" refers to C1-C 10 Heterocyclic alkyl groups have divalent groups with essentially the same structure.
[0513] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system (with 6 to 60 carbon atoms). For example, the term "C6-C" as used herein...60 "Arylene" refers to a divalent group that has a carbocyclic aromatic system (with 6 to 60 carbon atoms). C6-C 60 Examples of aryl groups may include phenyl, pentanenyl, naphthyl, azulel, indole, acenaphthel, phenanthyl, phenanthryl, anthracene, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentanenyl, heptanenyl, tetraphenyl, framyl, hexaphenyl, pentaphenyl, rubiginyl, myristyl, and / or ovoxyl. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups independently comprises two or more rings, the corresponding rings can fused together.
[0514] As used in this article, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system, which further includes at least one heteroatom other than a carbon atom as a cyclic atom and 1 to 60 carbon atoms. The term "C1-C" is used herein. 60 "Hypo-heteroaryl" refers to a divalent group having a heterocyclic aromatic system, which further includes at least one heteroatom other than a carbon atom as a cyclic atom and 1 to 60 carbon atoms. C1-C 60 Examples of heteroaryl groups may include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzo[a]quinolinyl, isoquinolinyl, benzo[a]isoquinolinyl, quinoxalinyl, benzo[a]quinoxalinyl, quinazolinyl, benzo[a]quinazolinyl, cyclolinyl, phenanthrolinel, phthalazinyl, and / or naphthidyl. When C1-C 60 heteroaryl and C1-C 60 When each heteroaryl group independently comprises two or more rings, the corresponding rings can fused together.
[0515] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group having two or more fused rings and with only carbon atoms (e.g., 8 to 60 carbon atoms) as cyclic atoms, wherein the molecular structure is nonaromatic when considered as a whole. Examples of monovalent nonaromatic fused polycyclic groups may include indenyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, indeno[a]phenanthryl, and / or indeno[a]anthrayl. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having substantially the same structure as a monovalent nonaromatic fused polycyclic group.
[0516] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group having two or more fused rings and at least one heteroatom other than carbon atoms (e.g., 1 to 60 carbon atoms) as a cyclic atom, wherein the molecular structure is nonaromatic when considered as a whole. Examples of monovalent nonaromatic fused heterocyclic groups may include 9,9-dihydroacridinyl and 9H-xanthonyl. As used herein, the term "divalent nonaromatic fused heterocyclic group" refers to a divalent group having substantially the same structure as a monovalent nonaromatic fused heterocyclic group.
[0517] As used in this article, the term "C6-C" 60 "Aryloxy" indicator - OA 102 (where A) 102 For C6-C 60 (aryl), and as used herein, C6-C 60 Aryl thioyl indicator - SA 103 (where A) 103 For C6-C 60 Aryl).
[0518] As used in this article, the term "C7-C" 60 "Arylalkyl" refers to -A 104 A 105 (where A) 104 Can be C1-C 54 Alkylene, and A 105 It can be C6-C 59 Aryl), and as used herein by the term "C2-C 60 "Heteroarylalkyl" refers to -A 106 A 107 (where A) 106 Can be C1-C 59 Alkylene, and A 107 Can be C1-C 59 (Miscellaneous aromatic compounds).
[0519] As used in this article, the term "R" 10a "Can be:
[0520] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl, cyano, or nitro;
[0521] Each of the following C1-C that was not replaced or was replaced by: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group or C1-C 60 Alkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Arylalkyl, C2-C 60 heteroarylalkyl, -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;
[0522] Each of the following C3-Cs was not replaced or was replaced by the others 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroarylalkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Arylalkyl, C2-C 60 heteroarylalkyl, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) or any combination thereof; or
[0523] -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 ).
[0524] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each can be independently represented as: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy groups; C3-C groups that are unsubstituted or substituted with the following: 60 carbonyl group or C1-C 60 Heterocyclic groups: deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, phenyl, biphenyl, or any combination thereof; C7-C 60 arylalkyl; or C2-C 60 Heteroarylalkyl.
[0525] As used herein, the term "heteroatom" refers to any atom other than a carbon atom. Examples of heteroatoms may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
[0526] As used herein, the term “third-row transition metals” may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), and / or gold (Au).
[0527] In this article, "Ph" represents phenyl, "Me" represents methyl, "Et" represents ethyl, and "tert-Bu" or "Bu" represents ethyl. t " " indicates tert-butyl, and "OMe" as used in this article indicates methoxy.
[0528] As used in this article, the term "biphenyl" refers to a phenyl group that has been substituted with a phenyl group. "Biphenyl" belongs to the group with a C6-C... 60 A phenyl group with an aryl group as a substituent. As used herein, the term "terphenyl" refers to a phenyl group substituted with a biphenyl group or a phenyl group substituted with two phenyl groups.
[0529] "Triphenyl" belongs to the group that has C6-C 60 Aryl-substituted C6-C 60 Aryl or C6-C 60 Aryl groups are substituted phenyl groups.
[0530] Unless otherwise defined, the symbols *, *' and *” used herein refer to binding sites with adjacent atoms in the corresponding formula or part.
[0531] The compounds and luminescent devices according to one or more embodiments will be described in more detail below with reference to synthesis examples and embodiments. The phrase "using B instead of A" used in describing the synthesis examples means that the amount of B is the same as the amount of A in molar equivalents.
[0532] [Example]
[0533] Synthesis Example 1: Synthesis of compound A-1
[0534] The fused-ring compound A-1 according to one or more embodiments can be synthesized, for example, according to reaction scheme 1:
[0535] Reaction Scheme 1
[0536]
[0537] (Synthetic intermediate A-1-1)
[0538] 1,8-Dibromoanthracene (CAS No. 131276-24-9) / amyl nitrite (CAS No. 110-46-3) and 2-aminobenzoic acid (CAS No. 118-92-3) were reacted to obtain intermediate A-1-1. Intermediate A-1-1 was subjected to liquid chromatography-mass spectrometry (LC-MS) to identify its M+1 peak.
[0539] C 20 H 12 Br2: M+1 410.93
[0540] (Synthetic intermediate A-1-2)
[0541] Intermediate A-1-1 was reacted with n-BuLi, followed by reaction with trichlorophenylsilane (CAS No. 76-86-8) to obtain intermediate A-1-2. Intermediate A-1-2 was subjected to liquid chromatography-mass spectrometry (LC-MS) to identify its M+1 peak.
[0542] C 38 H 27 BrSi: M+1 591.10
[0543] (Synthetic compound A-1)
[0544] 5 g of intermediate A-1-2, 1.4 g of 9H-carbazole (CAS No. 86-74-8), 1.2 g of sodium tert-butoxide, 0.3 g of tris(dibenzylacetone)dipalladium(0), 0.3 mL of tritert-butylphosphine, and 45 mL of toluene were added to a reaction vessel and refluxed for 24 hours. Once the reaction was complete, the reaction solution was extracted with ethyl acetate, and the resulting organic layer was dried over magnesium sulfate. After evaporation of the solvent, the residue was separated and purified by silica gel column chromatography to give 4.3 g of compound A-1 (yield: 75%). The final product was analyzed by LC-MS and... 1 Compound A-1 was identified by ¹H-NMR.
[0545] Synthesis Example 2: Synthesis of compound A-12
[0546] Fused ring compound A-12 according to one or more embodiments can be synthesized, for example, according to reaction scheme 2.
[0547] Reaction Scheme 2
[0548]
[0549] (Synthetic intermediate A-12-1)
[0550] Bromobenzene-d5 (CAS No. 4165-57-5) and intermediate A-1-1 were each reacted with n-BuLi, followed by reaction with dichlorodiphenylsilane (CAS No. 80-10-4) to obtain intermediate A-12-1. Intermediate A-12-1 was subjected to liquid chromatography-mass spectrometry (LC-MS) to identify its M+1 peak.
[0551] C 38 H 22 D5BrSi: M+1 596.15
[0552] (Synthetic compound A-12)
[0553] 4.5 g of intermediate A-12-1, 2.5 g of 3,9'-bi-9H-carbazole (CAS No. 18628-07-4), 1.1 g of sodium tert-butoxide, 0.27 g of tris(dibenzylacetone)dipalladium(0), 0.25 mL of tri-tert-butylphosphine, and 40 mL of toluene were added to a reaction vessel and refluxed for 24 hours. Once the reaction was complete, the reaction solution was extracted with ethyl acetate, and the resulting organic layer was dried over magnesium sulfate. After evaporation of the solvent, the residue was separated and purified by silica gel column chromatography to give 4.4 g of compound A-12 (yield: 70%). The final product was analyzed by LC-MS and... 1 Compound A-12 was identified by ¹H-NMR.
[0554] Synthesis Example 3: Synthesis of compound A-39
[0555] Fused ring compound A-39 according to one or more embodiments can be synthesized, for example, according to reaction scheme 3.
[0556] Reaction scheme 3
[0557]
[0558] (Synthetic intermediate A-39-1)
[0559] 3-Bromo-9H-carbazole (CAS No. 1592-95-6) was reacted with 2-dibenzothiophene boric acid (CAS No. 668983-97-9) in the presence of a Pd catalyst to obtain intermediate A-39-1. Intermediate A-39-1 was subjected to liquid chromatography-mass spectrometry (LC-MS) to identify its M+1 peak.
[0560] C 24 H 15 NS: M+1 350.11
[0561] (Synthetic intermediate A-39-2)
[0562] Intermediate A-39-2 was synthesized in essentially the same manner as intermediate A-12-1, except that 3-bromo-1,1'-biphenyl (CAS No. 2113-57-7) was used instead of bromobenzene-d5 (CAS No. 4165-57-5). Intermediate A-39-2 was subjected to LC-MS to identify its M+1 peak.
[0563] C 44 H 31 BrSi: M+1 667.13
[0564] (Synthetic compound A-39)
[0565] 2.4 g of intermediate A-39-1, 4.5 g of intermediate A-39-2, 0.97 g of sodium tert-butoxide, 0.25 g of tris(dibenzylacetone)palladium(0), 0.2 mL of tri-tert-butylphosphine, and 35 mL of toluene were added to a reaction vessel and refluxed for 24 hours. Once the reaction was complete, the reaction solution was extracted with ethyl acetate, and the resulting organic layer was dried over magnesium sulfate. After evaporation of the solvent, the residue was separated and purified by silica gel column chromatography to give 4.6 g of compound A-39 (yield: 73%). The final product was analyzed by LC-MS and... 1 Compound A-39 was identified by ¹H-NMR.
[0566] Synthesis Example 4: Synthesis of compound A-127
[0567] The fused-ring compound A-127 according to one or more embodiments can be synthesized, for example, according to reaction scheme 4.
[0568] Reaction scheme 4
[0569]
[0570] (Synthetic compound A-127)
[0571] 4 g of intermediate A-39-2, 1.3 g of dibenzofuranboronic acid (CAS No. 100124-06-9), 1.6 g of potassium carbonate, 0.35 g of tetra(triphenylphosphine)palladium(0), 32 mL of tetrahydrofuran, and 8 mL of water were added to a reaction vessel and refluxed for 24 hours. Once the reaction was complete, the reaction solution was extracted with ethyl acetate, and the resulting organic layer was dried over magnesium sulfate. After evaporation of the solvent, the residue was separated and purified by silica gel column chromatography to give 3.1 g of compound A-127 (yield: 70%). The final product was analyzed by LC-MS and... 1 Compound A-127 was identified by ¹H-NMR.
[0572] Synthesis Example 5: Synthesis of compound A-175
[0573] The fused-ring compound A-175 according to one or more embodiments can be synthesized, for example, according to reaction scheme 5.
[0574] Reaction scheme 5
[0575]
[0576] (Synthetic intermediate A-175-1)
[0577] Intermediate A-175-1 was synthesized in essentially the same manner as intermediate A-12-1, except that bromobenzene-d5 (CAS No. 4165-57-5) was replaced with 4-bromo-1,1'-biphenyl (CAS No. 92-66-0). Intermediate A-175-1 was subjected to LC-MS to identify its M+1 peak.
[0578] C 44 H 31 BrSi: M+1 667.17
[0579] (Synthetic compound A-175)
[0580] 4.5 g of intermediate A-175-1, 2 g of 9-phenyl-3-carbazoleboric acid (CAS No. 854952-58-2), 2.3 g of potassium carbonate, 0.4 g of tetra(triphenylphosphine)palladium(0), 40 mL of tetrahydrofuran, and 10 mL of water were added to a reaction vessel and refluxed for 24 hours. Once the reaction was complete, the reaction solution was extracted with ethyl acetate, and the resulting organic layer was dried over magnesium sulfate. After evaporation of the solvent, the residue was separated and purified by silica gel column chromatography to give 3.8 g of compound A-175 (yield: 68%). The final product was analyzed by LC-MS and... 1 Compound A-175 was identified by ¹H-NMR.
[0581] Synthesis Example 6: Synthesis of compound C-6
[0582] The fused-ring compound C-6 according to one or more embodiments can be synthesized, for example, according to reaction scheme 6.
[0583] Reaction scheme 6
[0584]
[0585] (Synthetic intermediate C-6-1)
[0586] Intermediate A-12-1 was reacted with bis(pinacol)diboron (CAS No. 73183-34-3) in the presence of a Pd catalyst to obtain intermediate C-6-1. Intermediate C-6-1 was subjected to LC-MS to identify its M+1 peak.
[0587] C 44 H 34 D5BO2Si: M+1 644.32
[0588] (Synthetic compound C-6)
[0589] 5 g of intermediate C-6-1, 2.1 g of 2-chloro-4,6-diphenyl-1,3,5-triazine (CAS No. 3842-55-5), 2.7 g of potassium carbonate, 0.45 g of tetra(triphenylphosphine)palladium(0), 40 mL of tetrahydrofuran, and 10 mL of water were added to a reaction vessel and refluxed for 24 hours. Once the reaction was complete, the reaction solution was extracted with ethyl acetate, and the resulting organic layer was dried over magnesium sulfate. After evaporation of the solvent, the residue was separated and purified by silica gel column chromatography to give 3.9 g of compound C-6 (yield: 68%). The final product was analyzed by LC-MS and... 1 Compound C-6 was identified by 1H-NMR.
[0590] Synthesis Example 7: Synthesis of compound C-11
[0591] The fused-ring compound C-11 according to one or more embodiments can be synthesized, for example, according to reaction scheme 7.
[0592] Reaction Scheme 7
[0593]
[0594] (Synthetic intermediate C-11-1)
[0595] Intermediate C-11-1 was synthesized in essentially the same manner as intermediate A-12-1, except that 5'-bromo-1,1':3',1”-terphenyl (CAS No. 103068-20-8) was used instead of bromobenzene-d5 (CAS No. 4165-57-5). Intermediate C-11-1 was subjected to LC-MS to identify its M+1 peak.
[0596] C 50 H 35 BrSi: M+1 743.15
[0597] (Synthetic intermediate C-11-2)
[0598] Intermediate C-11-2 was synthesized in essentially the same manner as intermediate C-6-1, except that intermediate C-11-1 was used instead of intermediate A-12-1. Intermediate C-11-2 was subjected to LC-MS to identify its M+1 peak.
[0599] C 56 H 47 BO2Si: M+1 791.33
[0600] (Synthetic compound C-11)
[0601] 4 g of intermediate C-11-2, 1.35 g of 2-chloro-4,6-diphenylpyrimidine (CAS No. 2915-16-4), 1.75 g of potassium carbonate, 0.3 g of tetra(triphenylphosphine)palladium(0), 28 mL of tetrahydrofuran, and 7 mL of water were added to a reaction vessel and refluxed for 24 hours. Once the reaction was complete, the reaction solution was extracted with ethyl acetate, and the resulting organic layer was dried over magnesium sulfate. After evaporation of the solvent, the residue was separated and purified by silica gel column chromatography to give 3 g of compound C-11 (yield: 65%). The final product was analyzed by LC-MS and... 1 Compound C-11 was identified by ¹H-NMR.
[0602] Synthesis Example 8: Synthesis of compound C-19
[0603] The fused-ring compound C-19 according to one or more embodiments can be synthesized, for example, according to reaction scheme 8.
[0604] Reaction Scheme 8
[0605]
[0606] (Synthetic intermediate C-19-1)
[0607] Intermediate C-19-1 was synthesized in essentially the same manner as intermediate C-6-1, except that intermediate A-1-2 was used instead of intermediate A-12-1. Intermediate C-19-1 was subjected to LC-MS to identify its M+1 peak.
[0608] C 44 H 39 BO2Si: M+1 639.30
[0609] (Synthetic compound C-19)
[0610] 5 g of intermediate C-19-1, 2.1 g of 4-chloro-2,6-diphenylpyridine (CAS No. 133785-60-1), 2.7 g of potassium carbonate, 0.45 g of tetra(triphenylphosphine)palladium(0), 40 mL of tetrahydrofuran, and 10 mL of water were added to a reaction vessel and refluxed for 24 hours. Once the reaction was complete, the reaction solution was extracted with ethyl acetate, and the resulting organic layer was dried over magnesium sulfate. After evaporation of the solvent, the residue was separated and purified by silica gel column chromatography to give 4 g of compound C-19 (yield: 70%). The final product was analyzed by LC-MS and... 1 Compound C-19 was identified by ¹H NMR.
[0611] Synthesis Example 9: Synthesis of compound C-33
[0612] The fused-ring compound C-33 according to one or more embodiments can be synthesized, for example, according to reaction scheme 9.
[0613] Reaction Scheme 9
[0614]
[0615] (Synthetic intermediate C-33-1)
[0616] 9H-carbazole (CAS No. 86-74-8) was reacted with n-BuLi, followed by reaction with 2,4-dichloro-6-phenyl-1,3,5-triazine (CAS No. 1700-02-3) to obtain intermediate C-33-1. Intermediate C-33-1 was subjected to LC-MS to identify its M+1 peak.
[0617] C 21 H 13 ClN4: M+1 357.08
[0618] (Synthetic intermediate C-33-2)
[0619] Intermediate C-33-2 was synthesized in essentially the same manner as intermediate C-6-1, except that intermediate A-39-2 was used instead of intermediate A-12-1. Intermediate C-33-2 was subjected to LC-MS to identify its M+1 peak.
[0620] C 50 H 43 BO2Si: M+1 715.30
[0621] (Synthetic compound C-33)
[0622] 2.5 g of intermediate C-33-1, 5 g of intermediate C-33-2, 2.5 g of potassium carbonate, 0.4 g of tetra(triphenylphosphine)palladium(0), 40 mL of tetrahydrofuran, and 10 mL of water were added to a reaction vessel and refluxed for 24 hours. Once the reaction was complete, the reaction solution was extracted with ethyl acetate, and the resulting organic layer was dried over magnesium sulfate. After evaporation of the solvent, the residue was separated and purified by silica gel column chromatography to give 4 g of compound C-33 (yield: 64%). The final product was analyzed by LC-MS and... 1 Compound C-33 was identified by ¹H-NMR.
[0623] Synthesis Example 10: Synthesis of compound C-55
[0624] The fused-ring compound C-55 according to one or more embodiments can be synthesized, for example, according to reaction scheme 10.
[0625] Reaction Scheme 10
[0626]
[0627] (Synthetic intermediate C-55-1)
[0628] 2,4-Dichloro-6-phenyl-1,3,5-triazine (CAS No. 1700-02-3) was reacted with [3-(triphenylsilyl)phenyl]boronic acid (CAS No. 1253915-58-1) in the presence of a Pd catalyst to obtain intermediate C-55-1. Intermediate C-55-1 was subjected to LC-MS to identify its M+1 peak.
[0629] C 33 H 24 ClN3Si: M+1 526.13
[0630] (Synthetic compound C-55)
[0631] 4.9 g of intermediate C-19-1, 4 g of intermediate C-55-1, 2.6 g of potassium carbonate, 0.44 g of tetra(triphenylphosphine)palladium(0), 40 mL of tetrahydrofuran, and 10 mL of water were added to a reaction vessel and refluxed for 24 hours. Once the reaction was complete, the reaction solution was extracted with ethyl acetate, and the resulting organic layer was dried over magnesium sulfate. After evaporation of the solvent, the residue was separated and purified by silica gel column chromatography to give 4.6 g of compound C-55 (yield: 60%). The final product was analyzed by LC-MS and... 1 Compound C-55 was identified by ¹H-NMR.
[0632] Synthesis Example 11: Synthesis of compound C-61
[0633] The fused-ring compound C-61 according to one or more embodiments can be synthesized, for example, according to reaction scheme 11.
[0634] Reaction Scheme 11
[0635]
[0636] (Synthetic intermediate C-61-1)
[0637] 9H-carbazole (CAS No. 86-74-8) was reacted with n-BuLi, followed by reaction with 2,4,6-trichloro-1,3,5-triazine (CAS No. 108-77-0) to obtain intermediate C-61-1. Intermediate C-61-1 was subjected to LC-MS to identify its M+1 peak.
[0638] C 15 H8Cl2N4: M+1 315.00
[0639] (Synthetic intermediate C-61-2)
[0640] Intermediate C-61-1 was reacted with [4-(triphenylsilyl)phenyl]boronic acid (CAS No. 852475-03-7) in the presence of a Pd catalyst to obtain intermediate C-61-2. Intermediate C-61-2 was subjected to LC-MS to identify its M+1 peak.
[0641] C 39 H 27 ClN4Si: M+1 615.17
[0642] (Synthetic compound C-61)
[0643] 4.2 g of intermediate C-19-1, 4 g of intermediate C-61-2, 2.6 g of potassium carbonate, 0.38 g of tetra(triphenylphosphine)palladium(0), 32 mL of tetrahydrofuran, and 8 mL of water were added to a reaction vessel and refluxed for 24 hours. Once the reaction was complete, the reaction solution was extracted with ethyl acetate, and the resulting organic layer was dried over magnesium sulfate. After evaporation of the solvent, the residue was separated and purified by silica gel column chromatography to give 3.9 g of compound C-61 (yield: 55%). The final product was analyzed by LC-MS and... 1 Compound C-61 was identified by ¹H-NMR.
[0644] The compounds synthesized in Examples 1 to 11 were obtained by means of 1 Identification was performed by ¹H-NMR and mass spectrometry / fast atom bombardment (MS / FAB). The results are shown in Table 1. Those skilled in the art can readily understand the method for synthesizing compounds other than those shown in Table 1 by referring to the above-described synthetic scheme and starting materials.
[0645] Table 1
[0646]
[0647] Example 1
[0648] Corning 15 ohms / cm² (Ω / cm) 2 ) The ITO glass substrate is cut into 50 mm × 50 mm × 0.7 mm pieces, sonicated in isopropyl alcohol and pure water for 5 minutes each, and cleaned by exposure to ultraviolet light and ozone to use the glass substrate as an anode. The glass substrate is then mounted into a vacuum deposition apparatus.
[0649] N,N'-bis(1-naphthyl)-N,N'-diphenylbenzidine (NPB) was vacuum deposited onto a substrate until... The thickness is adjusted to form a hole injection layer. Subsequently, mCP is vacuum-deposited onto the hole injection layer to a thickness of [missing information]. The thickness is increased to form a hole transport layer.
[0650] Compound A-1 (the host compound) and Ir(pmp)3 (the dopant compound) were co-deposited on the hole transport layer at a weight ratio of 92:8. The thickness is adjusted to form the emission layer.
[0651] Then, 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ) was deposited on the emitter layer until... The thickness is such that an electron transport layer is formed.
[0652] Depositing LiF onto the electron transport layer to The thickness is such that an electron injection layer is formed, and Al is vacuum deposited on the electron injection layer to a thickness of [missing information]. The thickness is increased to form the cathode, thus completing the formation of the LiF / Al electrode. Therefore, a light-emitting device is manufactured.
[0653] Examples 2 to 11
[0654] The other light-emitting device was manufactured in essentially the same manner as in Example 1, except that the compounds shown in Table 2 were used instead of compound A-1 to form the emitting layer.
[0655] Comparative Examples 1 to 7
[0656] The other light-emitting device was manufactured in essentially the same manner as in Example 1, except that compound mCP and compounds CP-1 to CP-6 were used instead of compound A-1 to form the emitting layer.
[0657]
[0658]
[0659] To evaluate the characteristics of the light-emitting devices according to Examples 1 to 11 and Comparative Examples 1 to 7, at a speed of 10 mA / cm², the following tests were conducted. 2 The driving voltage, current density, and maximum quantum yield were measured at the current density of the light-emitting device. The driving voltage and current density of each light-emitting device were measured using a source meter (Keithley Instrument, 2400 series). The maximum quantum yield of each light-emitting device was measured using a Hamamatsu AbsolutePL measurement system C9920-2-12. In the evaluation of the maximum quantum yield, the luminance / current density was measured using a luminance meter calibrated with wavelength sensitivity, and the maximum quantum yield was calculated under the assumption of an angular luminance distribution (Lambertian) on a perfectly diffuse surface. The evaluation results of the light-emitting devices are shown in Table 2.
[0660] Table 2
[0661]
[0662]
[0663] Referring to the results in Table 2, it was found that the light-emitting devices of Examples 1 to 11 each have a low driving voltage and / or a high maximum quantum yield compared to the light-emitting devices of Comparative Examples 1 to 7.
[0664] As is evident from the preceding description, the fused-ring compound represented by Formula 1 can have high triplet energy, and therefore, light-emitting devices including fused-ring compounds represented by Formula 1 can exhibit high luminous efficiency.
[0665] As used herein, the terms “substantially,” “about,” and similar terms are used as terms of approximation, not degree, and are intended to describe the inherent biases of measured or calculated values that would be recognized by one of ordinary skill in the art. As used herein, “about” or “approximation” includes the stated value and means within an acceptable range of deviation for a particular value, determined by one of ordinary skill in the art taking into account the measurement in question and the errors associated with the measurement of the particular quantity (i.e., limitations of the measurement system). For example, “about” may mean within one or more standard deviations of the stated value, or within ±30%, ±20%, ±10%, or ±5% of the stated value.
[0666] Any numerical range set forth herein is intended to include all subranges of the same numerical precision falling within the set forth range. For example, the range “1.0 to 10.0” is intended to include (and inclusive) the stated minimum value of 1.0 and the stated maximum value of 10.0, that is, all subranges having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limit set forth herein is intended to include all lower numerical limits falling within it, and any minimum numerical limit set forth herein is intended to include all higher numerical limits falling within it. Therefore, the applicant reserves the right to amend this specification (including the claims) to expressly set forth any subrange falling within the range expressly set forth herein.
[0667] It should be understood that the embodiments described herein are for descriptive purposes only and are not intended to be limiting. The description of features or aspects in each embodiment should generally be considered applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, those skilled in the art will understand that various suitable changes in form and detail may be made therein without departing from the spirit and scope defined by the appended claims and their equivalents.
Claims
1. A light-emitting device, comprising: First electrode; The second electrode facing the first electrode; as well as An interlayer comprising an emission layer is provided between the first electrode and the second electrode. The light-emitting device comprises a fused-ring compound represented by Formula 1: Formula 1 In Equation 1, G1 is a group represented by Formula 2, and G2 is a group represented by one of formulas 3A to 3C: Formula 2 Formula 3A Formula 3B 3C Among them, in Equations 1, 2, and 3A to 3C, X 31 For N(R) 35 ), O or S, Z 31 For C(R) 36 ) or N, Z 32 For C(R) 37 ) or N, Z 33 For C(R) 38 ) or N, and Z 31 To Z 33 At least one of them is N, L 21 To L 23 and L 31 To L 34 Each is independently a single bond, unsubstituted, or affected by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group, a21 to a23 and a31 to a34 are each independent integers selected from 1 to 3. Ar 21 To Ar 23 Ar 31 and Ar 32 Each independently is either unsubstituted or by at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups or -Si(Q1)(Q2)(Q3), b21 to b23, b31 and b32 are each independent integers selected from 1 to 5. R1 to R5 and R 31 To R 38 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic group, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60 Arylthioyl, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), c1, c2, and c33 are each an independent integer selected from 1 to 3. c3, c31, c32, and c34 are each independent integers selected from 1 to 4. *Indicates the binding site with adjacent atoms, and R 10a for: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro; Each of the following C1-C that was not replaced or was replaced by: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 Alkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthioyl, -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; Each of the following C3-Cs was not replaced or was replaced by the others 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 aryloxy or C6-C 60 Aryl thiols: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthioyl, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) or any combination thereof; 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 Among them, Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each of the following is independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy groups; or C3-C groups that are unsubstituted or substituted with the following: 60 Carbocyclic or C1-C 60 Heterocyclic groups: deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, phenyl, biphenyl, or any combination thereof.
2. The light-emitting device of claim 1, wherein the emitting layer comprises the fused ring compound represented by Formula 1.
3. The light-emitting device of claim 1, wherein the emitting layer comprises a host and a dopant, the content of the host in the emitting layer is greater than the content of the dopant in the emitting layer, and the host comprises the fused ring compound represented by Formula 1.
4. The light-emitting device of claim 1, wherein the emitting layer comprises a host and a dopant, the content of the host in the emitting layer is greater than the content of the dopant in the emitting layer, and the dopant comprises the fused ring compound represented by Formula 1.
5. The light-emitting device of claim 2, wherein the emitting layer is used to emit blue light having a maximum emission wavelength in the range of 390 nm to 440 nm.
6. The light-emitting device as claimed in claim 1, wherein the first electrode is an anode. The second electrode is a cathode. The interlayer further includes a hole transport region between the first electrode and the emitter layer, and an electron transport region between the emitter layer and the second electrode. The hole transport region includes a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof, and The electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
7. An electronic device comprising a light-emitting device as described in any one of claims 1 to 6.
8. The electronic device of claim 7, further comprising a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.
9. A fused-ring compound represented by Formula 1: Formula 1 in, In Equation 1, G1 is a group represented by Formula 2, and G2 is a group represented by one of formulas 3A to 3C: Formula 2 Formula 3A Formula 3B 3C Among them, in Equations 1, 2, and 3A to 3C, X 31 For N(R) 35 ), O or S, Z 31 For C(R) 36 ) or N, Z 32 For C(R) 37 ) or N, Z 33 For C(R) 38 ) or N, and Z 31 To Z 33 At least one of them is N, L 21 To L 23 and L 31 To L 34 Each is independently a single bond, unsubstituted, or affected by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group, a21 to a23 and a31 to a34 are each independent integers selected from 1 to 3. Ar 21 To Ar 23 Ar 31 and Ar 32 Each independently is either unsubstituted or by at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups or -Si(Q1)(Q2)(Q3), b21 to b23, b31 and b32 are each independent integers selected from 1 to 5. R1 to R5 and R 31 To R 38 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic group, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60 Arylthioyl, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), c1, c2, and c33 are each independent integers selected from 1 to 3. c3, c31, c32, and c34 are each independent integers selected from 1 to 4. *Indicates the binding site with adjacent atoms, and R 10a for: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro; Each of the following C1-C that was not replaced or was replaced by: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 Alkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthioyl, -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; Each of the following C3-Cs was not replaced or was replaced by the others 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 aryloxy or C6-C 60 Aryl thiols: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthioyl, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) or any combination thereof; 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 Among them, Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each of the following is independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy groups; or C3-C groups that are unsubstituted or substituted with the following: 60 Carbocyclic or C1-C 60 Heterocyclic groups: deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, phenyl, biphenyl, or any combination thereof.
10. The fused-ring compound of claim 9, wherein L in formula 2 and formulas 3A to 3C 21 To L 23 and L 31 To L 34 Each independently is: Single key; or Each of the following is either unsubstituted or substituted: phenyl, pentanenyl, indene, naphthyl, azuleyl, heptenyl, indaneyl, acenaphtheyl, fluorenyl, spiro-difluorenyl, spiro-benzofluorenyl-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthreneyl, phenanthreneyl, anthraceneyl, fluoranyl, pyreneyl, 1,2-benzophenanthreneyl, tetraphenyl, lavany, peryleneyl, pyrroleyl, thiopheneyl, furanyl, thiorheyl, imidazolyl, pyrazolyl, thiazolyl, isothiazyl Azolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazole, benzothiophenyl, dibenzothiophenyl, quinolinyl, isoquinolinyl, benzimidazolyl, imidazopyridyl or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, pentanenyl, indene, naphthyl, azuleyl, heptenyl, indaneyl, acenaphthyl, fluorenyl, spiro-difluorenyl, spiro-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthraceneyl, fluoranyl, pyrene, 1,2-benzophenanthreneyl, tetraphenyl, lavany, peryl, pyrroleyl, thiopheneyl, furanyl, thiopheneyl Imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, benzothiophenyl, dibenzothiophenyl, quinolinyl, isoquinolinyl, benzimidazolyl, imidazopyridyl, imidazopyrimidinyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) or any combination thereof, and Q 31 To Q 33 Each independently is C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl.
11. The fused-ring compound of claim 9, wherein a21 to a23 and a31 to a34 in formulas 2 and 3A to 3C are each 1, and L 21 To L 23 and L 31 To L 34 Each is independently a single bond or a group represented by one of formulas 3-1 to 3-3 and 3-24: in, In equations 3-1 to 3-3 and 3-24 Z1 can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, or C1-C. 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, pyrene, 1,2-benzo[a]phenanthryl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, quinolinyl, isoquinolinyl, benzimidazolyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) or -B(Q 31 (Q) 32 ), d3 is an integer selected from 1 to 3, and d4 is an integer selected from 1 to 4, and Q 31 To Q 33 Each independently is C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, and *, *', and *” each indicate a binding site with an adjacent atom.
12. The fused-ring compound of claim 9, wherein Ar in formula 2 and formula 3C 21 To Ar 23 Ar 31 and Ar 32 Each independently is: Each of the following is either unsubstituted or substituted: cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, terphenyl, fluorenyl, spiro-difluorenyl, spiro-cyclopentane-fluorenyl, spiro-cyclohexane-fluorenyl, spiro-fluorenyl-benzo[fluorenyl], benzo[fluorenyl], dibenzo[fluorenyl], phenatenyl, phenanthrene, anthracene, fluoranyl, triphenylene, pyrene, 1 2-Benzenyl, Perylene, Pentenyl, Hexaphenyl, Pentaphenyl, Pyrrole, Thiophene, Furanyl, Thirrolyl, Imidazolyl, Pyrazolyl, Thiazolyl, Isothiazolyl, Oxazolyl, Isoxazolyl, Pyridyl, Pyrazinyl, Pyrimidinyl, Pyridazinyl, Triazinyl, Indolyl, Isoyindolyl, Indolyl, Puryl, Quinolinyl, Isoquinolinyl, Benzoquinolinyl, Phtharazinyl, Naphthidyl, Quinoxolinyl, Quinazolinyl, Pyrolinyl, Phenyridyl, Phenyridyl, Acridineyl, Phenyrrolinyl, Phenazinyl, Benzimidazolyl, Benzofuranyl, Benzothiophene, Benzothiopyrroleyl, Benzoisothiazolyl, Benzooxazolyl, Benzoisooxazolyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Dibenzofuranyl, Dibenzothiophene, Dibenzothiopyrroleyl, Carbohydrate Azolyl, benzocarbazoyl, dibenzocarbazoyl, azafluorenyl, azaspiro-difluorenyl, azacarbazoyl, diazacarbazoyl, azadibenzofuranyl, azadibenzothiopheneyl, azadibenzothiopheneyl, imidazopyridyl or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, terphenyl, fluorenyl, spiro-difluorenyl, spiro-cyclopentane-fluorenyl, spiro-cyclohexane-fluorenyl, spiro-fluorenyl-benzo[fluorenyl], benzo[fluorenyl], dibenzo[fluorenyl], phenanthrenyl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthrene, perylene, penfenyl, hexaphenyl, pentaphenyl, pyrroleyl, thiopheneyl, furanyl, thiopheneyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indoleyl, isoyindolyl, indazoleyl, purineyl, quinolinyl, iso Quinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiopheneyl, benzothiopyrrolyl, benzoisothiazolyl, benzooxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, dibenzofuranyl, dibenzothiopheneyl, dibenzothiopyrrolyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, azafluorenyl, azaspiro-difluorenyl, azacarbazoleyl, diazacarbazoleyl, azadibenzofuranyl, azadibenzothiopheneyl, azadibenzothiopyrrolyl, imidazopyridyl, imidazopyrimidinyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) or any combination thereof; or -Si(Q1)(Q2)(Q3), and Among them, Q1 to Q3 and Q 31 To Q 33 Each independently is C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl.
13. The fused-ring compound of claim 9, wherein Ar in formula 2 and formula 3C 21 To Ar 23 Ar 31 and Ar 32 Each is independently represented by a group or -Si(Q1)(Q2)(Q3) from formula 5-1 to 5-19: in, In equations 5-1 to 5-19, Y 51 is O, S, N(Z 53 ), C(Z 54 )(Z 55 ) or Si(Z 56 )(Z 57 ), Z 51 To Z 57 Each of these groups can be independently represented as hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, or C1-C. 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, pyrene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, dibenzothiopheneyl, quinolinyl, isoquinolinyl, benzimidazolyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) or -B(Q 31 (Q) 32 ), e3 is an integer selected from 1 to 3. e4 is an integer selected from 1 to 4. e5 is an integer selected from 1 to 5. e6 is an integer selected from 1 to 6. e7 is an integer selected from 1 to 7, and e9 is an integer selected from 1 to 9, and Among them, Q1 to Q3 and Q 31 To Q 33 Each independently is C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, and * Indicates the binding site with adjacent atoms.
14. The fused-ring compound of claim 9, wherein Ar in formula 2 and formula 3C 21 To Ar 23 Ar 31 and Ar 32 Each is independently represented by one of the formulas 6-1 to 6-42: and in, In equations 6-1 to 6-42, "t-Bu" represents tert-butyl. "Ph" represents phenyl. "TMS" stands for trimethylsilyl. "TPS" stands for triphenylsilyl, and * Indicates the binding site with adjacent atoms.
15. The fused-ring compound of claim 9, wherein: (i) At least one of R1 to R5 in Equation 1 is deuterium. (ii) Ar in Equation 2 21 To Ar 23 At least one of them is replaced by deuterium. (iii) When G2 is a group represented by formula 3A, R 31 and R 32 At least one of them is deuterium, or R 31 and R 32 At least one of them is replaced by deuterium. (iv) When G2 is a group represented by formula 3B, R 33 and R 34 At least one of them is deuterium, or R 33 To R 35 At least one of them is replaced by deuterium. (v) When G2 is a group represented by formula 3C, Ar 31 and Ar 32 At least one of them is replaced by deuterium, or One of (vi)(iii) to (v), and any combination of (i) and (ii).
16. The fused-ring compound of claim 9, wherein R in formula 3A to 3C 31 To R 38 Each independently represents: hydrogen, deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isonyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, tert-decyl or -Si(Q1)(Q2)(Q3); or Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothiophene, carbazole, or dibenzothiophene: deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, tert-decyl, phenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothiophene, carbazole, dibenzothiophene, -Si(Q) 31 (Q) 32 (Q) 33 ) or any combination thereof, and Among them, Q1 to Q3 and Q 31 To Q 33 Each independently is C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl.
17. The fused-ring compound of claim 9, wherein G1 in formula 1 is a group represented by formula 2(1): Equation 2(1) and in, In equation 2(1), R 21 To R 23 Each independently with R 10a same, c21 to c23 are each an independent integer selected from 0 to 5, and * Indicates the binding site with adjacent atoms.
18. The fused-ring compound of claim 9, wherein G2 in formula 1 is represented by one of formulas 3C(1) to 3C(5): in, In equations 3C(1) to 3C(5), L 34 It is a single bond or a group represented by formula 3-2 or formula 3-3. and Among them, in equations 3-2 and 3-3, Z1 can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, or C1-C. 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, pyrene, 1,2-benzo[a]phenanthryl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, quinolinyl, isoquinolinyl, benzimidazolyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) or -B(Q 31 (Q) 32 ), d4 is an integer selected from 1 to 4. Q 31 To Q 33 Each independently is C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, and L 32 L 33 、a32、a33、Ar 31 Ar 32 b31 and b32 are each independently identical to those defined in Equation 3C, and * and *' each indicate the binding site with the adjacent atom.
19. The fused-ring compound of claim 18, wherein, In equations 3C(1) to 3C(5), L 32 and L 33 Each is independently a single bond or a group represented by one of formulas 3-1 to 3-3. a32 and a33 are each 1. Ar 31 and Ar 32 Each is independently a group represented by one of formulas 6-1 to 6-42, and b31 and b32 are each 1: and In Equation 3-1, Z1 and d4 are each independently identical to those described by combining Equations 3-2 and 3-3, and In Equations 3-1 to 3-3, * and *' each indicate a binding site with an adjacent atom. Among them, in equations 6-1 to 6-42, "t-Bu" represents tert-butyl. "Ph" represents phenyl. "TMS" stands for trimethylsilyl. "TPS" stands for triphenylsilyl, and * Indicates the binding site with adjacent atoms.
20. The fused-ring compound of claim 9, wherein the fused-ring compound represented by Formula 1 is selected from compounds A-1 to A-240 and compounds C-1 to C-136:
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