Organic light emitting device
By using a polycyclic compound represented by Formula 1 as the host material in an organic light-emitting device to form an organic layer, the problems of insufficient efficiency and color purity of existing OLEDs are solved, and a high-efficiency and high-color-purity light-emitting effect is achieved.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- SAMSUNG ELECTRONICS CO LTD
- Filing Date
- 2021-03-05
- Publication Date
- 2026-04-21
AI Technical Summary
Existing organic light-emitting devices (OLEDs) are insufficient in terms of efficiency and color purity, making it difficult to meet high-performance requirements.
A polycyclic compound represented by Formula 1 is used as the main material of the organic layer, and its content is controlled to be less than that of the main compound to form an organic layer between the first electrode and the second electrode, thereby improving luminous efficiency and color purity.
This improves the luminous efficiency and color purity of organic light-emitting devices, meeting the requirements of high-performance displays.
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Figure CN113363398B_ABST
Abstract
Description
[0001] Cross-reference to related applications
[0002] This application is based on and claims priority to Korean Patent Application No. 10-2020-0027988 filed on March 5, 2020, and Korean Patent Application No. 10-2021-0021419 filed on February 17, 2021, the disclosures of which are incorporated herein by reference in their entirety. Technical Field
[0003] This disclosure relates to organic light-emitting devices. Background Technology
[0004] Organic light-emitting devices (OLEDs) are self-emitting devices that, compared to conventional devices, have a wide viewing angle, high contrast, short response time, and excellent brightness, driving voltage, and response speed characteristics, and can produce full-color images.
[0005] An OLED includes an anode, a cathode, and an organic layer between the anode and cathode, including an emitter layer. A hole transport region is located between the anode and the emitter layer, and an electron transport region is located between the emitter layer and the cathode. Holes supplied from the anode can move towards the emitter layer through the hole transport region, and electrons supplied from the cathode can move towards the emitter layer through the electron transport region. Holes and electrons recombine in the emitter layer to generate excitons. These excitons can transition from an excited state to a ground state, thereby producing light. Summary of the Invention
[0006] One or more embodiments include organic light-emitting devices with high efficiency and high color purity.
[0007] Other aspects will be set forth in part in the description which follows, and in part will be apparent from the description, or may be learned by practice of the embodiments presented in this disclosure.
[0008] According to one aspect of the implementation, the organic light-emitting device may include a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, including an emitting layer.
[0009] The organic layer may include a polycyclic compound represented by Formula 1 and a host, and
[0010] The content of the polycyclic compound may be less than the content of the main component.
[0011] Formula 1
[0012]
[0013] Formula 1A
[0014]
[0015] In Equations 1 and 1A,
[0016] Ar1 can be a group represented by formula 1A.
[0017] Rings CY1 and CY2 can each be independently C5-C. 30 Carbocyclic groups or C1-C 30 Heterocyclic groups,
[0018] Y1 can be B, N, P, P (=O), P (=S), Al, Ga, As, Si (R5), or Ge (R5).
[0019] X1 and X2 can be independently selected from O, S, Se, N(R6), C(R6)(R7), Si(R6)(R7), Ge(R6)(R7), and P(=O)(R6).
[0020] L1 and L 11 Each can be independently selected from single-bonded, substituted, or unsubstituted C5-C bonds. 30 Carbocyclic groups and substituted or unsubstituted C1-C 30 Heterocyclic groups,
[0021] a1 and a11 can each be an integer from 1 to 3 independently.
[0022] When a1 is 2 or greater, at least two L1s can be the same or different from each other, and when a11 is 2 or greater, at least two L1s can be the same or different from each other. 11 They can be the same or different from each other.
[0023] R1, R2, R3, R4, R5, R6, R7, R 11 and R 12 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C groups. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7), and -P(=O)(Q8)(Q9),
[0024] R1 and R2 may optionally combine to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups,
[0025] b1 and b2 can each be an integer between 0 and 10 independently.
[0026] When b1 is 2 or greater, at least two R1s can be the same or different from each other, and when b2 is 2 or greater, at least two R2s can be the same or different from each other.
[0027] b11 can be an integer from 1 to 5.
[0028] When b11 is 2 or greater, at least two Rs 11 They can be the same or different from each other.
[0029] b12 can be an integer from 1 to 8.
[0030] When b12 is 2 or greater, at least two Rs 12 They can be the same or different from each other.
[0031] c11 can be an integer from 1 to 8.
[0032] When c11 is 2 or greater, at least two -(L) 11 ) a11 -(R 11 ) b11 They can be the same or different from each other.
[0033] The sum of b12 and c11 can be 9.
[0034] Replacement C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthio-, substituted C7-C 60 Aryl groups, substituted C1-C 60 The heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and at least one substituent of the substituted monovalent non-aromatic fused heterocyclic group may be selected from...
[0035] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, and C1-C 60 Alkoxy
[0036] Each is selected from at least one of the following C1-C substituted. 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, and C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 14 (Q) 15 -B(Q) 16 (Q) 17), and -P(=O)(Q 18 (Q) 19 ),
[0037] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups.
[0038] Each is selected from at least one of the following C3-C substituted. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 24(Q) 25 -B(Q) 26 (Q) 27 ), and -P(=O)(Q 28 (Q) 29 ),and
[0039] -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 34 (Q) 35 -B(Q) 36 (Q) 37 ), and -P(=O)(Q 38 (Q) 39 ),
[0040] Among them, Q1-Q9, Q 11 -Q 19 Q 21 -Q 29 , and Q 31 -Q 39 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C groups. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups. Attached Figure Description
[0041] The above and other aspects, features and advantages of some embodiments will become clearer from the following description taken in conjunction with the accompanying drawings, wherein:
[0042] Figure 1A schematic cross-sectional view of an organic light-emitting device according to an embodiment; and
[0043] Figure 2A-2C Each diagram schematically illustrates the energy transfer in the emitting layer of the organic light-emitting device according to an embodiment. Detailed Implementation
[0044] An organic light-emitting device may include: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, including an emitting layer, wherein the organic layer may include a polycyclic compound represented by Formula 1 and a host, and the content of the polycyclic compound may be less than the content of the host.
[0045] The polycyclic compound may include compounds represented by Formula 1:
[0046] Formula 1
[0047]
[0048] Formula 1A
[0049]
[0050] Among them, in Equations 1 and 1A,
[0051] Ar1 can be a group represented by Formula 1A. In Formula 1A, * indicates a binding site with Formula 1.
[0052] In Equation 1, rings CY1 to CY2 can each be independently represented as C5-C. 30 Carbocyclic groups or C1-C 30 Heterocyclic groups.
[0053] In embodiments, CY1 and CY2 may each be independently selected from A group, B group, a fused ring in which at least two groups selected from A group are fused, a fused ring in which at least two groups selected from B group are fused, and a fused ring in which at least one group selected from A group and at least one group selected from B group are fused.
[0054] Group A can be selected from cyclopent-1,3-diene groups, indene groups, azulene groups, phenyl groups, naphthyl groups, anthracene groups, phenanthrene groups, tetraphenyl groups, butylphenyl groups, pyrene groups, etc. Groups, benzo[9,10]phenanthrene groups, and fluorene groups, and
[0055] The B group can be selected from furan groups, thiophene groups, pyrrole groups, borocyclopentadienyl groups, thiophene groups, pyrrolidinyl groups, imidazole groups, thiazole groups, triazole groups, etc. azole group, iso- The following groups are included: azole group, isothiazole group, pyridine group, pyrimidine group, pyridazine group, triazine group, indole group, isoindole group, indazine group, quinoline group, isoquinoline group, quinoxaline group, isoquinoxaline group, carbazole group, dibenzofuran group, dibenzothiophene group, dibenzothiophene group, and dibenzoborone heterocyclopentadiene group.
[0056] In one or more embodiments, group A may be selected from phenyl groups, naphthyl groups, and anthracene groups, and group B may be selected from carbazole groups, dibenzofuran groups, dibenzothiophene groups, dibenzothiophene groups, and dibenzoborane groups.
[0057] For example, CY1 and CY2 can be independently selected from phenyl groups, naphthyl groups, anthracene groups, and fluorene groups, but the implementation is not limited to this.
[0058] In Equation 1, Y1 can be B, N, P, P (=O), P (=S), Al, Ga, As, Si (R5), or Ge (R5). For example, Y1 can be B, N, P, P (=O), P (=S), Al, or Ga.
[0059] In Equation 1, X1 and X2 can be independently selected from O, S, Se, N(R6), C(R6)(R7), Si(R6)(R7), Ge(R6)(R7), and P(=O)(R6).
[0060] In the implementation, X1 and X2 can be the same as each other. For example, X1 and X2 can each be O, S, N (R6), C (R6)(R7), or Si (R6)(R7), but the implementation is not limited to this.
[0061] In one or more embodiments, X1 and X2 may be different from each other. For example, X1 may be 0 and X2 may be S; X1 may be 0 and X2 may be N(R6); X1 may be 0 and X2 may be C(R6)(R7); X1 may be 0 and X2 may be Si(R6)(R7); X1 may be S and X2 may be N(R6); X1 may be S and X2 may be C(R6)(R7); X1 may be S and X2 may be Si(R6)(R7); X1 may be N(R6) and X2 may be C(R6)(R7); X1 may be N(R6) and X2 may be Si(R6)(R7); or X1 may be C(R6)(R7) and X2 may be Si(R6)(R7). For example, X2 can be O and X1 can be S; X2 can be O and X1 can be N(R6); X2 can be O and X1 can be C(R6)(R7); X2 can be O and X1 can be Si(R6)(R7); X2 can be S and X1 can be N(R6); X2 can be S and X1 can be C(R6)(R7); X2 can be S and X1 can be Si(R6)(R7); X2 can be N(R6) and X1 can be C(R6)(R7); X2 can be N(R6) and X1 can be Si(R6)(R7); or X2 can be C(R6)(R7) and X1 can be Si(R6)(R7).
[0062] In the implementation, Y1 can be B, and X1 and X2 can each be independently selected from O, S, Se, N(R6), C(R6)(R7), and Si(R6)(R7), but the implementation is not limited to this.
[0063] In Equations 1 and 1A, L1 and L 11 Each can be independently selected from single-bonded, substituted, or unsubstituted C5-C bonds. 30 Carbocyclic groups, and substituted or unsubstituted C1-C 30 Heterocyclic groups.
[0064] In the implementation, L1 and L 11 Each can be selected independently:
[0065] single bond;
[0066] Phenylidene, indene, naphthylene, azulene, heptadienyl, acenaphthene, fluorene, phenenyl, phenanthrene, anthracene, fluorenyl, benzo[9,10]phenanthrene, pyrene, and phenyl base; and
[0067] Each of the following is substituted with at least one of the following: phenylene, indene, naphthene, azene, heptadeneyl, acenaphthene, fluorene, phenentheneyl, phenanthrene, anthraceneyl, fluorenthraceneyl, benzo[9,10]phenanthrene, pyreneyl, and phenentheneylyl Groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups; and
[0068] Each of the following is selected as a substituted phenylene, indene, naphthene, azene, heptadeninyl, acenaphthene, fluorene, phenenenyl, phenanthrene, anthracene, fluorenyl, benzo[9,10]phenanthrene, pyrene, and phenenthene The radicals are each selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 At least one substituted phenyl, indenyl, naphthyl, azulel, heptalenyl, acenaphthel, fluorenyl, phenatenyl, anthracenel, fluoranyl, benzo[9,10]phenanthryl, pyrene, and heteroaryl, monovalent non-aromatic fused heterocyclic group, and monovalent non-aromatic fused heterocyclic group. The method is based on this, but the implementation is not limited to this.
[0069] For example, L1 and L 11The components can be selected from single bonds and groups represented by formulas 3-1 to 3-32, but the implementation is not limited thereto:
[0070]
[0071]
[0072] Among them, in equations 3-1 to 3-32,
[0073] Z 31 The following groups can be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl groups and C1-C 60 Mixed aromatics,
[0074] Each is selected from at least one of the following C3-C substituted. 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl groups and C1-C 60 Heteroaryl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 24 (Q) 25 -B(Q) 26 (Q) 27 ), and -P(=O)(Q 28 (Q) 29 ),
[0075] e4 can be an integer from 1 to 4.
[0076] e6 can be an integer from 1 to 6.
[0077] e8 can be an integer from 1 to 8, and
[0078] * and *' each represent a binding site with an adjacent atom.
[0079] In Equations 1 and 1A, a1 and a11 can each be independent integers from 1 to 3, and when a1 is 2 or greater, at least two L1s can be the same or different from each other, and when a11 is 2 or greater, at least two L1s can be different from each other. 11 They may be the same as or different from each other.
[0080] In equations 1 and 1A, R1, R2, R3, R4, R5, R6, R7, R 11 and R 12 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C groups. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C1-C 60 The polycyclic aromatic hydrocarbon group (PAH), substituted or unsubstituted monovalent non-aromatic fused polycyclic aromatic hydrocarbon group (PAH), -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7), and -P(=O)(Q8)(Q9) are used, and in Formula 1, R1 and R2 may optionally be combined to form a substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.
[0081] In one or more embodiments, in Formula 1, R1 and R2 can each be independently selected from:
[0082] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano (CN), nitro, amino, C1-C 60 Alkyl groups and C1-C 60 Alkoxy;
[0083] Each of the C1-Cs is replaced by at least one of the following: 60 Alkyl and C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano (CN), nitro, amino, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, and base;
[0084] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazineyl, dibenzofuranyl, dibenzothiophenylyl, and carbazoleyl;
[0085] Each of the following is substituted with at least one of the following: cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthraceneyl, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, and carbazoleyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, C1-C 60 Alkyl, C1-C 60 Alkoxy, C7-C 60 Aryl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, diazolyl, triazine, dibenzofuranyl, dibenzothiophene, carbazole, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 34 (Q) 35 -B(Q) 36 (Q) 37 ), and -P(=O)(Q 38 (Q) 39 );and
[0086] -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7), and -P(=O)(Q8)(Q9), but the implementation is not limited to these.
[0087] In some implementations, R1 and R2 can be independently selected from:
[0088] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, and tert-hexyl;
[0089] Each of the following is substituted with at least one of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, and tert-hexyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, and phenyl.
[0090] In the implementation, at least one of R1 and R2 may be selected from formulas 5-1 and 5-2, but the implementation is not limited thereto:
[0091]
[0092] In equations 5-1 and 5-2,
[0093] R 51 -R 55 Each can be independently:
[0094] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, phenyl, biphenyl, and terphenyl; and
[0095] Each of the following is substituted with at least one of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, and tert-hexyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, and phenyl.
[0096] R 54 and R 55 They can optionally combine with each other to form heterocycles, and
[0097] b54 and b55 can each be an integer between 0 and 4 independently.
[0098] For example, in Equation 5-1, R 51 -R 53One of them can be phenyl, and R 51 -R 53 The other two can be selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, and tert-hexyl.
[0099] For example, in Equation 5-1, R 51 -R 53 Each of these can be independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, and tert-hexyl. For example, in Formula 5-1, R 51 -R 53 Each can be a methyl group.
[0100] For example, in Equation 5-2, R 54 and R 55 They can combine with each other to form a pentagonal ring with the ring-forming atom N.
[0101] In one or more embodiments, in Formula 1, R3 and R4 can each be independently selected from:
[0102] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, and tert-hexyl;
[0103] Each of the following is substituted with at least one of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, and tert-hexyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, and phenyl, but the embodiments are not limited thereto.
[0104] For example, R3 and R4 can each be hydrogen.
[0105] In the implementation method, in Equation 1, R5, R6, and R7 can each be independently selected from:
[0106] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, and tert-hexyl;
[0107] Each of the following is substituted with at least one of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, and tert-hexyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, and phenyl.
[0108] Phenyl, biphenyl, naphthyl, fluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl;
[0109] Each of the following is substituted with at least one of the following: phenyl, biphenyl, naphthyl, fluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl, but the embodiments are not limited thereto.
[0110] In the implementation method, in formula 1A, R 11 Options 4-1 to 4-42 are optional.
[0111] R 12 The following can be selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, and tert-hexyl;
[0112] Each of the following is substituted with at least one of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, and tert-hexyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, and phenyl, but the embodiments are not limited thereto:
[0113]
[0114]
[0115] Among them, in equations 4-1 to 4-42,
[0116] Y 31 It can be O, S, C(Z) 45 (Z) 46 ), N(Z 47 ), or Si(Z) 48 (Z) 49 ),
[0117] Z 41 -Z 49 Each can be selected independently:
[0118] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, C7-C 60 Aryl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazineyl, dibenzofuranyl, dibenzothiophenylyl, and carbazoleyl;
[0119] Each of the following is substituted with at least one of the following: cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazine, dibenzofuranyl, dibenzothiopheneyl, and carbazoleyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy groups and C7-C 60 Aryl groups, such as cumyl groups, are used, but the implementation methods are not limited to this.
[0120] f3 can be an integer from 1 to 3.
[0121] f4 can be an integer from 1 to 4.
[0122] f5 can be an integer from 1 to 5.
[0123] f6 can be an integer from 1 to 6.
[0124] f7 can be an integer from 1 to 7.
[0125] f9 can be an integer from 1 to 9, and
[0126] * indicates a binding site with an adjacent atom.
[0127] In Equation 1, b1 and b2 can each be an integer from 0 to 10 independently, and when b1 is 2 or greater, at least two R1s can be the same or different from each other, and when b2 is 2 or greater, at least two R2s can be the same or different from each other.
[0128] In Equation 1A, b11 can be an integer from 1 to 5, and when b11 is 2 or greater, at least two R... 11 They may be the same as or different from each other.
[0129] In Equation 1A, b12 can be an integer from 1 to 8, and when b12 is 2 or greater, at least two R... 12 They may be the same as or different from each other.
[0130] In Equation 1A, c11 can be an integer from 1 to 8, and when c11 is 2 or greater, at least two -(L) 11 ) a11 -(R 11 ) b11 They may be the same as or different from each other.
[0131] In Equation 1A, the sum of b12 and c11 can be 9. For example, b12 can be 8, and c11 can be 1.
[0132] In the implementation, formula 1A can be selected from formulas 1A-1 to 1A-5:
[0133]
[0134]
[0135] Among them, in equations 1A-1 to 1A-5,
[0136] L 11 a 11 R 11 and b 11 You can refer to the L provided in this article respectively 11 a 11 R 11 and b 11 Based on the description,
[0137] R 21 -R 29 Each can refer to the R provided in this article. 12 Understanding based on the description, and
[0138] * indicates a binding site with an adjacent atom.
[0139] In an embodiment, the polycyclic compound may include a compound represented by any one of formulas 2-1 to 2-8:
[0140]
[0141]
[0142] Among them, in equations 2-1 to 2-8,
[0143] Y1, X1, X2, R1, R2, R3, R4, R5, L1, a1, and Ar1 can be understood by referring to the descriptions of Y1, X1, X2, R1, R2, R3, R4, R5, L1, a1, and Ar1 provided in this document.
[0144] In an embodiment, the polycyclic compound may be selected from compounds 1 to 468:
[0145]
[0146]
[0147]
[0148]
[0149]
[0150]
[0151]
[0152]
[0153]
[0154]
[0155]
[0156]
[0157]
[0158]
[0159]
[0160]
[0161]
[0162]
[0163] As in Formula 1, the core containing element Y1 in the polycyclic compound can have a planar structure with multiple resonances and a rigid framework fused together by sharing benzene rings. Therefore, the polycyclic compound can exhibit high color purity. Simultaneously, the fluorescent emitter represented by Formula 1 can include an anthracene group having a lowest excited triplet state (T1*) similar to the lowest excited triplet state (T1) of the core structure, and the efficiency is significantly improved because the resonance between T1 and T1* via reverse intersystem crossing (RISC) through a spin-orbit coupling (SOC) mechanism can be enhanced.
[0164] Compounds with multiple resonance structures in related fields can achieve improved color purity, but efficiency improvements cannot be achieved due to reduced spatial overlap between the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO). On the other hand, donor-acceptor structures in which the HOMO and LUMO are spatially spaced to reduce the ΔEst value have been proposed to improve efficiency. In this embodiment, efficiency is improved; however, the oscillator strength is reduced, thereby decreasing color purity. Color purity and efficiency are in a trade-off relationship.
[0165] However, since organic light-emitting devices according to one or more embodiments may include polycyclic compounds represented by Formula 1, both color purity and efficiency can be improved by using a triple resonance mechanism that simultaneously employs multiple resonance mechanisms and a resonance mechanism between triplet states.
[0166] In an embodiment, the polycyclic compound represented by Formula 1 may be a fluorescent emitter.
[0167] In an embodiment, the emission layer may further include a sensitizer that satisfies Equation 1, and the content of the host compound may be greater than the total content of the sensitizer and the polycyclic compound.
[0168] Equation 1
[0169] ΔE ST ≤0.3eV
[0170] In equation 1, ΔE STThis represents the energy level gap between the lowest excited singlet level (S1) and the lowest excited triplet level (T1).
[0171] Here, triplet and singlet energy levels can be evaluated using density functional theory (DFT) methods, where the structure is optimized at the B3LYP and 6-31G(d,p) levels according to the Gaussian procedure.
[0172] The sensitizer and the polycyclic compound can satisfy conditions 1 and 2:
[0173] Condition 1
[0174] T 衰减 (PC) <T 衰减 (S)
[0175] Condition 2
[0176] T 衰减 (PC) < 1.5 μs
[0177] Among them, in conditions 1 and 2,
[0178] T 衰减 (PC) represents the decay time of the polycyclic compound, and
[0179] T 衰减 (S) represents the decay time of the sensitizer.
[0180] The decay time of the polycyclic compound was calculated using time-resolved photoluminescence (TRPL) spectra of a 40 nm thick film (hereinafter referred to as the "film (CD)") at room temperature, which was obtained by: at 10 -7 Under vacuum pressure, the host and dopant (i.e., the polycyclic compound) included in the emission layer are vacuum co-deposited on a quartz substrate at a weight ratio of 90:10.
[0181] The decay time of the sensitizer was calculated using the TRPL of a 40 nm thick film (hereinafter referred to as "film (S)") at room temperature, which was obtained by: at 10 -7 Under vacuum pressure, the host and sensitizer included in the emission layer are vacuum co-deposited on a quartz substrate at a weight ratio of 90:10.
[0182] It is generally known that triplet excitons remain in the excited state for extended periods, thus contributing to a reduction in the lifetime of organic light-emitting devices (OLEDs). However, according to this disclosure, the polycyclic compound is used to reduce the time that triplet excitons of the sensitizer remain in the excited state during this period. Therefore, OLEDs incorporating the polycyclic compound can have an extended lifetime.
[0183] In one or more embodiments, the more triplet excitons the sensitizer has, the more excess energy accumulates in the sensitizer, resulting in more thermal excitons. That is, the amount of triplet excitons in the sensitizer is proportional to the amount of thermal excitons. The thermal excitons break various chemical bonds of compounds included in the emitter layer and / or compounds present at the interface between the emitter layer and other layers, causing the compounds to degrade. Therefore, the lifetime of the organic light-emitting device can be reduced. However, according to this disclosure, by using polycyclic compounds, the triplet excitons of the sensitizer can be rapidly converted into singlet excitons of the polycyclic compound, ultimately reducing the amount of thermal excitons and improving the lifetime of the organic light-emitting device.
[0184] In this respect, “thermal excitons” are generated or increased by: exciton-exciton annihilation due to the increase in exciton density in the emitter layer, exciton-charge annihilation due to charge imbalance in the emitter layer, and / or radical ion pairs due to the transfer of electrons between the host and the dopant (e.g., the polycyclic compound).
[0185] In order to rapidly convert the triplet exciton of the sensitizer into the singlet exciton of the polycyclic compound, condition 1 should be satisfied.
[0186] Furthermore, since the polycyclic compound emits fluorescence, it can provide an organic light-emitting device with high color purity. In particular, since condition 2 is satisfied, the singlet excitons of the polycyclic compound in the excited state at room temperature can be rapidly transferred, and therefore, the singlet states of the polycyclic compound in the excited state do not accumulate, and the lifetime of the organic light-emitting device can be improved.
[0187] Furthermore, when condition 3 is further satisfied, the transition from the triplet exciton of the sensitizer to the singlet exciton of the polycyclic compound can occur more smoothly. Therefore, the lifetime of the organic light-emitting device can be further extended.
[0188] Condition 3
[0189] T 衰减 (PC) / T 衰减 (S)<0.5
[0190] Among them, in condition 3,
[0191] T 衰减 (PC) represents the decay time of the polycyclic compound, and
[0192] T 衰减 (S) represents the decay time of the sensitizer.
[0193] In one or more embodiments, the organic light-emitting device may further satisfy condition 4:
[0194] Condition 4
[0195] BDE(S)–T1(S)<3.0eV
[0196] Among them, in condition 4,
[0197] BDE(S) is the bond dissociation energy level of the sensitizer, and
[0198] T1(S) is the lowest excited triplet energy level of the sensitizer.
[0199] Finally, the organic light-emitting device can achieve the target level of lifetime by satisfying the following condition 5:
[0200] Condition 5
[0201] R(Hex) / e 10 <15
[0202] Among them, in condition 5,
[0203] R(Hex) is the rate of thermal exciton production.
[0204] In this respect, R(Hex) undergoes the photochemical stability (photochemical stability) of the organic light-emitting device, and is thus calculated by the Gaussian 09 program according to the following equation C.
[0205] Equation C
[0206] R(Hex) = a × T 衰减 (S)×e -(BDE(S)–T 1(S))
[0207] In equation C,
[0208] a is an arbitrary constant.
[0209] T 衰减 (S) represents the decay time of the sensitizer.
[0210] BDE(S) is the bond dissociation energy level of the sensitizer, and
[0211] T1(S) is the lowest excited triplet energy level of the sensitizer.
[0212] The thermal exciton generation rate is estimated as (decay time) × e -(BDE-T1) Proportional, and in order to obtain the target level of lifetime for the organic light-emitting device, (thermal exciton generation rate) / e 10 It should be less than 15.
[0213] In this regard, the degradation analysis (PCS) of organic light-emitting devices is calculated according to the following equation P:
[0214] Equation P
[0215] PCS (%) = I2 / I1 × 100
[0216] In equation P,
[0217] The maximum light intensity of I1 for the film formed by depositing the PCS of the compound to be measured is obtained by the following PL spectrum: the PL spectrum was obtained immediately after the formation of the film at room temperature in an Ar atmosphere in which external air is blocked, using a He-Cd laser from KIMMON-KOHA Inc. (excitation wavelength = 325 nm, laser power density = 100 mW / cm²). 2 Evaluation, and
[0218] The maximum light intensity of I2 for the film formed by depositing the compound to be measured by its PCS is obtained by the following PL spectrum: the PL spectrum is obtained at room temperature in an Ar atmosphere in which external air is blocked by exposing the film to a He-Cd laser of KIMMON-KOHA Inc. (excitation wavelength = 325 nm, and laser power density = 100 mW / cm²) as the pump laser used to evaluate I1. 2 The assay was performed for 3 hours and then evaluated using a He-Cd laser (excitation wavelength = 325 nm) from KIMMON-KOHA Inc. In the case of the sensitizer, reverse intersystem crossing (RISC) and / or intersystem crossing (ISC) actively occur, allowing excitons generated at the host to be transported to the polycyclic compound.
[0219] Specifically, reference will be made to Figure 2A Describe the total energy transfer of the organic light-emitting device according to the embodiment.
[0220] Singlet and triplet excitons are formed at the host region in the emitter layer, and the energy of the singlet and triplet excitons formed at the host region is transferred to the sensitizer, and then through... Energy transfer (FRET) is transferred to the polycyclic compound. At this point, to achieve the high efficiency and long lifetime of organic light-emitting devices, the thermal excitons generated in the emitter layer must be controlled, which requires optimization of energy transfer.
[0221] Specifically, reference will be made to Figure 2B Describes the total energy transfer (Type I) of the organic light-emitting device according to an embodiment. This is when the sensitizer satisfies ΔE. ST The case of thermally activated delayed fluorescence (TADF) emitters under conditions ≤0.3 eV.
[0222] 25% of the energy of the singlet excitons formed at the host is transferred to the sensitizer via FRET, and 75% of the energy of the triplet excitons formed at the host is transferred to the singlet and triplet states of the sensitizer. The energy transferred to the triplet state undergoes RISC to become the singlet state, and then the singlet state energy of the sensitizer is transferred to the polycyclic compound via FRET.
[0223] Specifically, reference will be made to Figure 2C The overall energy transfer of the organic light-emitting device according to the embodiment is described (Type II). In this case, the sensitizer is an organometallic compound including Pt.
[0224] 75% of the energy of the triplet excitons formed at the host is transferred to the sensitizer via Dexter energy transfer, and 25% of the energy of the singlet excitons formed at the host is transferred to the singlet and triplet states of the sensitizer. The energy transferred to the singlet state undergoes ISC to become the triplet state, and then the triplet state energy of the sensitizer is transferred to the polycyclic compound via FRET.
[0225] Therefore, by transferring all singlet and triplet excitons generated in the emitter layer to the dopant, an organic light-emitting device with improved efficiency can be obtained. Furthermore, since an organic light-emitting device with significantly reduced energy loss can be obtained, the lifetime characteristics of the organic light-emitting device can be improved.
[0226] The amount of the sensitizer in the emission layer can be from about 5% by weight to about 50% by weight, relative to the total weight of the emission layer. Within these ranges, efficient energy transfer in the emission layer can be achieved, and thus, an organic light-emitting device with high efficiency and long lifetime can be obtained.
[0227] In one or more embodiments, the host, polycyclic compound, and sensitizer may further satisfy condition 6:
[0228] Condition 6
[0229] T1(H)≥T1(S)≥S1(PC)
[0230] Among them, in condition 6,
[0231] T1(H) is the lowest excited triplet state energy level of the host.
[0232] S1(PC) is the lowest excited singlet state energy level of the polycyclic compound, and
[0233] T1(S) is the lowest excited triplet energy level of the sensitizer.
[0234] When the host, the polycyclic compound, and the sensitizer each satisfy condition 6, triplet excitons can be efficiently transferred from the host to the polycyclic compound, and thus, an organic light-emitting device with improved efficiency can be obtained.
[0235] The emission layer may consist of the host, the polycyclic compound, and the sensitizer. That is, the emission layer may not further include materials other than the host, the polycyclic compound, and the sensitizer.
[0236] In one or more embodiments, the emitting layer may further include a photoluminescent dopant, and the content of the host may be greater than the total content of the photoluminescent dopant and the polycyclic compound represented by Formula 1. The photoluminescent dopant may include a photoluminescent dopant having suitable S1 and T1 energy levels to receive energy from the excitation S1 energy level of the polycyclic compound. In this embodiment, the polycyclic compound may be used as an energy-transferable sensitizer, and the polycyclic compound and the photoluminescent dopant may similarly satisfy the equations for the sensitizer and the polycyclic compound.
[0237] The method for synthesizing the polycyclic compounds represented by Formula 1 will be apparent to those skilled in the art by referring to the synthesis examples provided herein.
[0238] In an embodiment, in the organic light-emitting device...
[0239] The first electrode can be the anode, and the second electrode can be the cathode.
[0240] The organic layer may 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.
[0241] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and
[0242] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof, but the implementation is not limited thereto.
[0243] The emitting layer can emit blue light. For example, the blue light can have a wavelength in the range of about 440 nm to about 490 nm.
[0244] Figure 1 This is a schematic diagram of an exemplary embodiment of the organic light-emitting device 10. In the following sections, [the following will discuss...] Figure 1 This describes an exemplary embodiment of the structure of an organic light-emitting device and an exemplary embodiment of a method for manufacturing an organic light-emitting device. The organic light-emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked.
[0245] A substrate may be disposed below the first electrode 11 or above the second electrode 19. Any substrate used in conventional organic light-emitting devices may be used as the substrate, and the substrate may be a glass substrate or a transparent polymer substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling (processing), and water resistance.
[0246] The first electrode 11 can be formed by depositing or sputtering a material for forming the first electrode 11 onto a substrate. The first electrode 11 can be an anode. The material used to form the first electrode 11 can be selected from materials having a high work function to facilitate hole injection. The first electrode 11 can be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. The material used to form the first electrode 11 can be, for example, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) can be used as the material for forming the first electrode.
[0247] The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more layers. In an exemplary embodiment, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 11 is not limited to this.
[0248] The organic layer 15 is disposed on the first electrode 11.
[0249] The organic layer 15 may include a hole transport region, an emitter layer, and an electron transport region.
[0250] The hole transport region can be located between the first electrode 11 and the emitter layer.
[0251] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof.
[0252] The hole transport region may consist of only a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer / hole transport layer structure or a hole injection layer / hole transport layer / electron blocking layer structure, which are stacked sequentially from the first electrode 11 in the order stated herein.
[0253] The hole injection layer can be formed on the first electrode 11 by using one or more suitable methods selected from vacuum deposition, spin coating, tape casting, or Langmuir-Broguet (LB) deposition.
[0254] When a hole injection layer is formed by vacuum deposition, the deposition conditions can be varied depending on the compound used to form the hole injection layer, as well as the structure and thermal properties of the hole injection layer. In an exemplary embodiment, the deposition conditions may include a deposition temperature of about 100°C to about 500°C, and about 10 -8 To about 10 -3 The vacuum pressure of Tor and the treaty / seconds to approximately The deposition rate is 1 / s. However, the deposition conditions are not limited to this.
[0255] When spin coating is used to form the hole injection layer, the coating conditions can be varied depending on the material used to form the hole injection layer, as well as the structure and thermal properties of the hole injection layer. In an exemplary embodiment, the coating speed can be from about 2,000 rpm to about 5,000 rpm, and the temperature at which heat treatment is performed after coating to remove the solvent can be from about 80°C to about 200°C. However, the coating conditions are not limited to these.
[0256] By referring to the conditions used to form the hole injection layer, the conditions used to form the hole transport layer and the electron blocking layer can be understood.
[0257] The hole transport region may include m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-sulfonated styrene) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-sulfonated styrene) (PANI / PSS), compounds represented by formula 201, compounds represented by formula 202, or combinations thereof:
[0258]
[0259]
[0260] Formula 201
[0261]
[0262] Formula 202
[0263]
[0264] Ar in Equation 201 101 and Ar 102 Each can be independently:
[0265] Phenylidene, cyclopentadienyl, indene, naphthyl, azulene, heptadienyl, acenaphthene, fluorene, phenenyl, phenanthrene, anthracene, fluoranyl, benzo[9,10]phenanthrene, pyrene, phenylene alkyl, tetraphenylene, terephthalyl, perylene, or pentaphenylene; or
[0266] Each of the following substituted groups is phenylene, cyclopentadienylene, indene, naphthylene, azulene, heptadienylene, acenaphthene, fluorene, phenenylene, phenanthrene, anthracene, fluorenylene, benzo[9,10]phenanthrene, pyrene, etc. alkyl, tetraphenylene, terephthalyl, perylene, or pentaphenylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups.
[0267] In Equation 201, xa and xb can each be an integer from 0 to 5, or they can be 0, 1, or 2. In an exemplary embodiment, xa can be 1 and xb can be 0, but the implementation of this disclosure is not limited thereto.
[0268] R in equations 201 and 202 101 -R 108 R 111 -R 119 and R 121 -R 124 Each can be independently:
[0269] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, or C1-C 10 Alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), or C1-C 10Alkyl groups (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.);
[0270] Each of the following C1-C is replaced: 10 Alkyl or C1-C 10 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, or combinations thereof;
[0271] Phenyl, naphthyl, anthraceneyl, fluorenyl, and pyrene; or
[0272] The phenyl, naphthyl, anthraceneyl, fluorenyl, and pyrene groups, respectively, are substituted with the following: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, C1-C 10 Alkoxy groups, or combinations thereof, but the embodiments described herein are not limited thereto.
[0273] R in Equation 201 109 It can be: phenyl, naphthyl, anthraceneyl, and pyridyl; or
[0274] Each of the following groups is substituted: phenyl, naphthyl, anthraceneyl, and pyridyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, anthraceneyl, pyridyl, or combinations thereof.
[0275] In one embodiment, the compound represented by formula 201 may be represented by formula 201A, but the embodiments of this disclosure are not limited thereto:
[0276] Formula 201A
[0277]
[0278] R in Equation 201A 101 R 111 R 112 and R 109 Same as described above.
[0279] In exemplary embodiments, the compounds represented by formula 201 and formula 202 may include compounds HT1 to HT20, but embodiments of this disclosure are not limited thereto:
[0280]
[0281]
[0282]
[0283] 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 and a hole transport layer, the thickness of the hole injection layer can be approximately... to approximately and for example about to approximately Within a certain range, and the thickness of the hole transport layer can be approximately [missing information]. to approximately and for example about to approximately Within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage when the hole transport region, hole injection layer, and thickness of the hole transport layer are within these ranges.
[0284] In addition to these materials, the hole transport region may further include a charge-generating material for improving conductivity. The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region.
[0285] The charge-generating material may be, for example, a p-doper. The p-doper may be a quinone derivative, a metal oxide, or a compound containing a cyano group, but embodiments of this disclosure are not limited thereto. Non-limiting examples of the p-doper are quinone derivatives such as tetracyanoquinone dimethylane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethylane (F4-TCNQ); metal oxides such as tungsten oxide or molybdenum oxide; and compounds containing a cyano group such as, but not limited to, the following compounds HT-D1 or HT-D2:
[0286]
[0287] The hole transport region may include a buffer layer.
[0288] Furthermore, the buffer layer can compensate for the optical resonance distance according to the wavelength of the light emitted from the emission layer, and thus the efficiency of the formed organic light-emitting device can be improved.
[0289] The hole transport region may further include an electron blocking layer. The electron blocking layer may include, for example, mCP, but the material used therein is not limited to this:
[0290]
[0291] The emitter layer can then be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, etc. When the emitter layer is formed by vacuum deposition or spin coating, the deposition or coating conditions can be similar to those used when forming the hole injection layer, although the deposition or coating conditions can be varied depending on the compound used to form the emitter layer.
[0292] When the organic light-emitting device is a full-color organic light-emitting device, the emitting layer can be patterned as a red emitting layer, a green emitting layer, and a blue emitting layer. In one or more embodiments, due to the stacked structure including red, green, and / or blue emitting layers, the emitting layer can emit white light.
[0293] The emitter layer may include a host and a dopant, and the dopant may include a polycyclic compound represented by Formula 1.
[0294] The subject may include at least one of the following: TPBi, TBADN, ADN (also known as "DNA"), CBP, CDBP, TCP, mCP, and compounds H50 to H52:
[0295]
[0296] In one or more embodiments, the body may further comprise a compound represented by formula 301.
[0297] Formula 301
[0298]
[0299] Ar in Formula 301 111 and Ar 112 Each can be independently:
[0300] Phenylidene, naphthylene, phenanthrene, pyrene, or any combination thereof; or
[0301] Each of the following is substituted with at least one of the following: phenylene, naphthylene, phenanthrene, pyrene, or any combination thereof: phenyl, naphthyl, anthracene, or any combination thereof.
[0302] Ar in Formula 301 113 -Ar 116 Each can be independently:
[0303] C1-C 10 Alkyl, phenyl, naphthyl, phenanthryl, pyrene, or any combination thereof; or
[0304] Each of the following is substituted by at least one of the following: phenyl, naphthyl, phenanthryl, pyrene, or any combination thereof: phenyl, naphthyl, anthracene, or any combination thereof.
[0305] In Equation 301, g, h, i, and j can each be an integer from 0 to 4, and the sum can be, for example, 0, 1, or 2.
[0306] Ar in Formula 301 113 -Ar 116 Each can be independently:
[0307] C1-C replaced by at least one of the following 10 Alkyl groups: phenyl, naphthyl, anthracene, or any combination thereof;
[0308] Phenyl, naphthyl, anthraceneyl, pyrene, phenanthryl, fluorenyl, or any combination thereof;
[0309] Each of the following is substituted with at least one of the following: phenyl, naphthyl, anthraceneyl, pyrene, phenanthryl, fluorenyl, or any combination thereof: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkyl, phenyl, naphthyl, anthraceneyl, pyrene, phenanthryl, fluorenyl, or any combination thereof; or
[0310] However, the implementation of this disclosure is not limited thereto.
[0311] In one or more embodiments, the body may include a compound represented by the formula 302:
[0312] Formula 302
[0313]
[0314] Ar in Equation 302 122 -Ar 125 Regarding Ar in Equation 301 113 The details are the same.
[0315] Ar in Equation 302 126 and Ar 127 Each can be independently C1-C 10 Alkyl (e.g., methyl, ethyl, or propyl).
[0316] In Equation 302, k and l can each be an integer from 0 to 4 independently. For example, k and l can be 0, 1, or 2.
[0317] When the emitter layer comprises a substrate and a dopant, the amount of the dopant may be in the range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the substrate, but the embodiments of this disclosure are not limited thereto.
[0318] The thickness of the emission layer can be approximately to approximately For example, about to approximately Within these ranges, excellent light emission characteristics can be obtained without a significant increase in driving voltage when the thickness of the emitting layer is within any of these ranges.
[0319] Then, an electron transmission region can be set on the emission layer.
[0320] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
[0321] In an exemplary embodiment, the electron transport region may have a hole blocking layer / electron transport layer / electron injection layer structure or an electron transport layer / electron injection layer structure, but the structure of the electron transport region is not limited to these. The electron transport layer may have a multilayer structure or a single-layer structure comprising two or more different materials.
[0322] By referring to the conditions for forming the hole injection layer, the conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer constituting the electron transport region can be understood.
[0323] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP and Bphen, but may also include other materials:
[0324]
[0325] The thickness of the hole-blocking layer can be approximately to approximately For example, about to approximately Within these ranges, when the thickness of the hole blocking layer is within these ranges, the hole blocking layer can have improved hole blocking capability without a significant increase in driving voltage.
[0326] The electron transport layer may further include BCP, Bphen, Alq3, BAlq, TAZ, NTAZ, or combinations thereof.
[0327]
[0328] In one or more embodiments, the electronic transport layer may include, but is not limited to, ET1 to ET25:
[0329]
[0330]
[0331]
[0332] The thickness of the electron transport layer can be approximately to approximately For example, about to approximately Within the range described above, when the thickness of the electron transport layer is within the range described above, the electron transport layer can have satisfactory electron transport characteristics without a significant increase in driving voltage.
[0333] In addition to the materials described above, the electron transport layer may further include a material comprising metal.
[0334] The metal-containing material may include lithium (Li) complexes. The Li complexes may include, for example, compounds ET-D1 (lithium 8-hydroxyquinoline, LiQ) or ET-D2.
[0335]
[0336] The electron transport region may include an electron injection layer (EIL) that facilitates the inflow of electrons from the second electrode 19 therein.
[0337] The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, or combinations thereof.
[0338] The thickness of the electron injection layer can be approximately to approximately For example, about to approximately Within the range described above, when the thickness of the electron injection layer is within the range described above, the electron injection layer can have satisfactory electron injection characteristics without a significant increase in driving voltage.
[0339] The second electrode 19 may be formed on the organic layer 15. The second electrode 19 may be a cathode. The material used to form the second electrode 19 may be selected from metals, alloys, conductive compounds, and combinations thereof having relatively low work function. In exemplary embodiments, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be used as the material for forming the second electrode 19. In one or more embodiments, for the fabrication of a top-emitting light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.
[0340] As mentioned above, [the text has already been referenced]. Figure 1 Organic light-emitting devices have been described, but embodiments of the present disclosure are not limited thereto.
[0341] As used in this article, the term "C5-C" 30 A "carbocyclic group" refers to a saturated or unsaturated cyclic group with only 5-30 carbon atoms as cyclic atoms. (C5-C) 30 The carbon ring group can be a monocyclic group or a polycyclic group.
[0342] As used in this article, the term "C1-C" 30 A "heterocyclic group" refers to a saturated or unsaturated cyclic group that has at least one N, O, P, Si, S, or any combination thereof as a cyclic atom in addition to 1-30 carbon atoms. C1-C 30 Heterocyclic groups can be monocyclic or polycyclic.
[0343] As used in this article, the term "C1-C" 60 "alkyl" refers to a straight-chain or branched monovalent group of a saturated aliphatic hydrocarbon having 1-60 carbon atoms, and non-limiting examples include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. The term "C1-C" is used herein. 60 "alkylene" refers to a compound with C1-C2 atoms. 60 Divalent groups with the same structure as alkyl groups.
[0344] 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 are monovalent groups, and non-limiting examples include methoxy, ethoxy, and isopropoxy.
[0345] As used in this article, the term "C2-C" 60 "Alkenyl" refers to the group formed by the carbon atoms in the C2-C2 group. 60A hydrocarbon group formed by substituting at least one carbon-carbon double bond into the middle or end of an alkyl group, and examples include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" is used... 60 "Alkenyl" refers to a group with a C2-C ratio. 60 Divalent groups with the same structure as alkenyl groups.
[0346] As used in this article, the term "C2-C" 60 "Alkyne" refers to the group formed by the combination of C2-C... 60 A hydrocarbon group formed by substituting at least one carbon-carbon triple bond into the middle or end of an alkyl group, and examples include ethynyl and propynyl. As used herein, the term "C2-C" is used... 60 "Alynyl group" refers to a group with a C2-C group. 60 Divalent groups with the same structure as alkynyl groups.
[0347] As used in this article, the term "C3-C" 10 "Cycloalkyl" refers to a monocyclic saturated hydrocarbon group having 3-10 carbon atoms, and non-limiting examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. The term "C3-C" is used herein. 10 "Cycloalkylene" refers to a compound with C3-C66 atoms. 10 Divalent groups with the same structure as cycloalkyl groups.
[0348] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, P, Si, and S as a cyclic atom and 1-10 carbon atoms, and non-limiting examples include tetrahydrofuranyl and tetrahydrothiophenylyl. The term "C1-C" is used as is herein. 10 "Heterocyclic alkyl" refers to a compound with C1-C2 atoms. 10 Divalent groups with the same structure as heterocyclic alkyl groups.
[0349] As used in this article, the term "C3-C" 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3-10 carbon atoms and at least one carbon-carbon double bond in its ring and not being aromatic, and non-limiting examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. The term "C3-C" is used herein. 10 "Cyclopentene" refers to a group with a C3-C6 bond structure. 10 A divalent group with the same structure as a cycloalkenyl group.
[0350] As used in this article, the term "C1-C" 10"Heterocyclic alkenyl" refers to a monovalent monocyclic group that has at least one heteroatom selected from N, O, P, Si, and S as a cyclic atom, 1-10 carbon atoms, and at least one double bond and is not aromatic. C1-C 10 Non-limiting examples of heterocyclic alkenyl groups include 2,3-dihydrofuranyl and 2,3-dihydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl" refers to a group that has a C1-C2 bond structure. 10 Divalent groups with the same structure as heterocyclic alkenyl groups.
[0351] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system with 6-60 carbon atoms, and as used herein, "C6-C". 60 "Arylene" refers to a divalent group that has a carbocyclic aromatic system with 6-60 carbon atoms. (C6-C) 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, and Base. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, the rings may be fused together.
[0352] As used in this article, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group in a heterocyclic aromatic system having at least one heteroatom selected from N, O, P, Si, and S as a cyclic atom and 1-60 carbon atoms. The term "C1-C" is used herein. 60 "Hypo-heteroaryl" refers to a divalent group in a heterocyclic aromatic system having at least one heteroatom selected from N, O, P, Si, and S as a cyclic atom and 1-60 carbon atoms. (C1-C) 60 Non-limiting examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C1-C 60 heteroaryl and C1-C 60 When each heteroaryl group comprises two or more rings, the rings can fused together.
[0353] As used in this article, the term "C6-C" 60 "Aryloxy group" refers to -OA 102 (where A) 102 For C6-C 60 (aryl), and the C6-C used in this article 60 Arylthioyl group represents -SA 103 (where A) 103 For C6-C 60 Aryl).
[0354] As used in this article, the term "C7-C" 60 "Aryl" refers to -A 104 A 105 (where A) 104 For C1-C 54 Alkylene, and A 105 For C6-C 59 Aryl). C7-C 60 Non-limiting examples of aralkyl groups are cumyl (isopropylphenyl).
[0355] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group having two or more rings fused together, having only carbon atoms (e.g., the number of carbon atoms can range from 8 to 60) as cyclic atoms, and lacking aromaticity in its overall molecular structure. Non-limiting examples of monovalent nonaromatic fused polycyclic groups include the fluorene group. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused polycyclic group.
[0356] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group having two or more fused rings, having heteroatoms selected from N, O, P, Si, and S as cyclic atoms in addition to carbon atoms (e.g., the number of carbon atoms can range from 2 to 60), and not being aromatic in its overall molecular structure. Non-limiting examples of monovalent nonaromatic fused heterocyclic groups include the carbazole group. As used herein, the term "divalent nonaromatic fused heterocyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused heterocyclic group.
[0357] Replacement C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthio-, substituted C7-C 60 Aryl groups, substituted C1-C 60At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group may be:
[0358] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, or C1-C 60 Alkoxy;
[0359] Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, and C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(=O)(Q) 18 (Q) 19 ) or combinations thereof;
[0360] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups;
[0361] Each of the following C3-C is replaced: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(=O)(Q) 28 (Q) 29 ), or a combination thereof,
[0362] -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 34 (Q) 35 -B(Q) 36 (Q) 37 -P(=O)(Q) 38 (Q) 39 ),and
[0363] Q1-Q9, Q11 -Q 19 Q 21 -Q 29 , and Q 31 -Q 39 Each can be independently hydrogen, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic fused polycyclic group, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic group.
[0364] As used in this article, the term "room temperature" refers to approximately 25°C.
[0365] As used herein, the terms “biphenyl” and “terphenyl” refer to monovalent groups in which two or three phenyl groups are connected to each other by single bonds.
[0366] The compounds and organic light-emitting devices according to the embodiments will be described in detail below with reference to the synthesis examples and examples. However, the organic light-emitting devices are not limited thereto. The phrase "using B instead of A" used in describing the synthesis examples means that, in molar equivalents, the amount of A used is the same as the amount of B used.
[0367] Example
[0368] Synthesis Example 1: Synthesis of Compound 158
[0369]
[0370] Synthesis of intermediate 158(a)
[0371] 2.09 g (17.11 mmol) of phenylboronic acid, 5.0 g (14.88 mmol) of 9,10-dibromoanthracene, 1.72 g (1.49 mmol) of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4), 4.11 g (29.76 mmol) of potassium carbonate (K2CO3), and 1.22 g (2.98 mmol) of S-phos (2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl) were added to 50 mL of tetrahydrofuran and 50 mL of distilled water, followed by heating under reflux. Once the reaction was complete, the resulting mixture was cooled to room temperature. The organic layer was then extracted with ethyl acetate and dried over anhydrous sodium sulfate (Na2SO4) for concentration, followed by separation by silica gel column chromatography (dichloromethane / hexane). The solid obtained was recrystallized from hexane to give 4.23 g of white solid, intermediate 158(a) (yield: 85%).
[0372] LC-mass spectrometry (calculated value: 333.23 g / mol, measured value: 334.2 g / mol(M+1))
[0373] Synthesis of intermediate 158(b)
[0374] 4.2 g (12.60 mmol) of intermediate 158(a), 4.8 g (18.91 mmol) of bis(pinacol)diboron, 3.09 g (31.51 mmol) of potassium acetate (AcOK), and 0.46 g (0.63 mmol) of 1,1'-[bis(diphenylphosphino)ferrocene]palladium(II) dichloride Pd(dppf)Cl2 were added to the reaction vessel, and the mixture was dissolved in 30 mL of dioxane and stirred at 100 °C. Once the reaction was complete, the resulting mixture was cooled to room temperature and extracted with ethyl acetate and water to obtain an organic layer. The obtained organic layer was concentrated by filtration through silica gel column chromatography. The resulting solid intermediate 158(b) was used in subsequent reactions without any further purification. (4.1 g, yield: 86%)
[0375] LC-mass spectrometry (calculated value: 380.19 g / mol, measured value: 381.3 g / mol(M+1))
[0376] Synthesis of Compound 158
[0377] 5.99 g (15.76 mmol) of intermediate 158(b), 4.0 g (13.13 mmol) of 7-chloro-5,9-dioxa-13b-boronanaphene[3,2,1-de]anthracene, 0.38 g (0.66 mmol) of bis(dibenzylacetone)palladium(0)Pd(dba)2, 5.58 g (26.27 mmol) of tripotassium phosphate (K3PO4), and 1.08 g (2.63 mmol) of S-phos were added to 40 mL of toluene and 40 mL of distilled water. The mixture was then heated under reflux. Once the reaction was complete, the resulting mixture was cooled to room temperature. The organic layer was then extracted with ethyl acetate and dried over anhydrous sodium sulfate (Na2SO4) for concentration, followed by separation by silica gel column chromatography (dichloromethane / hexane). The solid obtained was recrystallized from hexane to give 3.6 g of a yellow solid, compound 158 (yield: 52%).
[0378] LC-mass spectrometry (calculated value: 522.41 g / mol, measured value: 523.4 g / mol(M+1))
[0379] Synthesis Example 2: Synthesis of Compound 160
[0380] Synthesis of Compound 160
[0381]
[0382] Compound 160 was synthesized in 4.2 g in substantially the same manner as in the synthesis of compound 158 in Synthetic Example 1, except that 2,12-di-tert-butyl-7-chloro-5,9-dioxa-13b-boronanaphen[3,2,1-de]anthracene was used instead of 7-chloro-5,9-dioxa-13b-boronanaphen[3,2,1-de]anthracene (yield: 69%).
[0383] LC-mass spectrometry (calculated value: 634.3 g / mol, measured value: 635.3 g / mol(M+1))
[0384] Synthesis Example 3: Synthesis of Compound 170
[0385] Synthesis of Compound 170
[0386]
[0387] Compound 170 was synthesized in 4.2 g in substantially the same manner as in the synthesis of compound 158 in Synthetic Example 1, except that 3,11-di-tert-butyl-7-chloro-5,9-dioxa-13b-boronanaphen[3,2,1-de]anthracene was used instead of 7-chloro-5,9-dioxa-13b-boronanaphen[3,2,1-de]anthracene (yield: 69%).
[0388] LC-mass spectrometry (calculated value: 634.3 g / mol, measured value: 635.3 g / mol(M+1))
[0389] Synthesis Example 4: Synthesis of Compound 165
[0390]
[0391] Synthesis of intermediate 165(a)
[0392] Intermediate 165(a) was synthesized in substantially the same manner as in the synthesis of compound 158(a) in Synthesis Example 1, except that (3-bromophenyl)boronic acid was used instead of phenylboronic acid (yield: 86%).
[0393] LC-mass spectrometry (calculated value: 408.05 g / mol, measured value: 409.05 g / mol(M+1))
[0394] Synthesis of intermediate 165(b)
[0395] Intermediate 165(a) was synthesized in substantially the same manner as in the synthesis of compound 158(b) in Synthesis Example 1, except that intermediate 165(a) was used instead of intermediate 158(a) (yield: 99%).
[0396] LC-mass spectrometry (calculated value: 456.23 g / mol, measured value: 457.2 g / mol(M+1))
[0397] Synthesis of Compound 165
[0398] 2.6 g of compound 165 was synthesized in substantially the same manner as in the synthesis of compound 158 in Synthesis Example 1, except that intermediate 165(b) was used instead of intermediate 158(b) (yield: 43%).
[0399] LC-mass spectrometry (calculated value: 598.21 g / mol, measured value: 599.31 g / mol (M+1))
[0400] Synthesis Example 5: Synthesis of Compound 167
[0401] Synthesis of Compound 167
[0402]
[0403] Compound 167 was synthesized in essentially the same manner as in the synthesis of compound 160 in Synthesis Example 2, except that intermediate 165(b) was used instead of intermediate 158(b) (yield: 55%).
[0404] LC-mass spectrometry (calculated value: 710.34 g / mol, measured value: 711.3 g / mol (M+1))
[0405] Evaluation Example 1: Material Property Evaluation
[0406] Table 1 shows the optical band gap E of some polycyclic compounds represented by Equation 1, such as compounds 158, 160, and 170. g S1 energy level, PL spectrum, and half-width (FWHM). The results are shown in Table 2.
[0407] Table 1
[0408]
[0409] Table 2
[0410]
[0411] Referring to the results in Table 2, it was found that the polycyclic compound represented by Formula 1 has excellent luminescence properties and suitable electrical properties for use as a dopant in electronic devices such as organic light-emitting devices.
[0412] Evaluation Example 2: Evaluation of Photoluminescent Quantum Yield (PLQY) and Decay Time
[0413] (1) Thin film preparation
[0414] The quartz substrate was prepared by washing with chloroform and pure water. Then, the compounds shown in Table 2 (99.5 wt% PMMA: 0.5 wt% of each compound) were dissolved individually in dichloromethane for use in spin coating. Thus, a film with a thickness of 30 nm was produced.
[0415] (2) Evaluation of photoluminescence quantum yield
[0416] The photoluminescence quantum yield in the thin film was evaluated using a Hamamatsu Photonics absolute PL quantum yield measurement system (Hamamatsu Photonics, Ltd., Shizuoka, Japan) equipped with a xenon lamp source, monochromator, photon multichannel analyzer, and integrating sphere, and employing PLQY measurement software. Accordingly, the PLQY of the thin films of the compounds shown in Table 2 was measured.
[0417] (3) Evaluation of decay time
[0418] The photoluminescence (PL) spectra of each film were evaluated at room temperature using a time-resolved photoluminescence (TRPL) measurement system, FluoTime 300 (available from PicoQuant), and a pump source, PLS340 (available from PicoQuant, excitation wavelength = 340 nm, spectral width = 20 nm). The wavelength of the main peak in the PL spectrum was then determined, and the number of photons emitted at the wavelength of the main peak for each film was repeatedly measured over time using time-correlated single-photon counting (TCSPC) while a photon pulse (pulse width = 500 picoseconds, ps) was applied to the film via the PLS340, thereby obtaining a TRPL curve suitable for adequate fitting. The TPL of the film was obtained by fitting the results to at least two exponential decay functions. 衰减 (E x (decay time). The function used for fitting is as described in Equation 1, and takes the decay time T that has the maximum value among the respective values of the exponential decay function used for fitting. 衰减 As T 衰减 (E x The decay time is the remaining decay time. The results are shown in Table 3. Using the remaining decay time T... 衰减 The value is used to determine the lifetime of typical fluorescence that will decay. Here, the same measurement is repeated again in the dark state (i.e., the state in which the pump signal incident on each of the films is blocked) during the same measurement time as that used to obtain the TRPL curve, thereby obtaining a baseline for fitting or a background signal curve that can be used as a baseline:
[0419] Equation 1
[0420]
[0421] Table 3
[0422]
[0423] Referring to the results shown in Table 3, it was found that the polycyclic compounds represented by Formula 1, such as compounds 158, 160 and 170, are suitable as dopants and have excellent PLQY (in films) and decay time characteristics.
[0424] Example 1
[0425] The glass substrate on which the ITO electrode is formed is cut into dimensions of 50 mm × 50 mm × 0.5 mm. The glass substrate is then ultrasonically treated in acetone, isopropanol, and pure water for approximately 15 minutes in each solvent, and cleaned by exposure to ultraviolet light and ozone for 30 minutes.
[0426] Subsequently, HAT-CN is deposited on the ITO electrode (anode) of the glass substrate to form a structure with... A hole injection layer of a certain thickness is formed, and NPB is deposited on the hole injection layer to form a hole injection layer with a thickness of [missing information]. A first hole transport layer of a certain thickness is formed, and TCTA is deposited on the first hole transport layer to form a layer with... A second hole transport layer of a certain thickness is formed, and mCP is deposited on the second hole transport layer to form a layer with... An electron blocking layer of a certain thickness.
[0427] The host, sensitizer, and emitter, as shown in Table 4, are co-deposited on the electron blocking layer at a predetermined weight ratio to thereby form a layer having The thickness of the emission layer.
[0428] DBFPO is deposited on the emitter layer to form a structure with A hole-blocking layer of a certain thickness was formed. DBFPO and LiQ were co-deposited on the hole-blocking layer at a weight ratio of 5:5 to form a hole-blocking layer with [missing information]. An electron transport layer of a certain thickness is formed. LiQ is deposited on the electron transport layer to form an electron transport layer with a thickness of [missing information]. An electron-injected layer of a certain thickness is formed. Aluminum (Al) is deposited on the electron-injected layer to form a layer with... A cathode of a certain thickness is used to complete the fabrication of organic light-emitting devices.
[0429]
[0430] Examples 2 to 5 and Comparative Examples 1 to 3
[0431] The organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 4 were used in the formation of the emitting layer.
[0432] Table 4
[0433]
[0434]
[0435]
[0436]
[0437] Evaluation Example 3: Evaluation of the characteristics of organic light-emitting devices
[0438] The driving voltage, T95 lifetime (which represents the time (in hours) it takes for the brightness of each organic light-emitting device to decrease to 95% of its initial brightness) and quantum yield of the organic light-emitting devices manufactured in Examples 1 to 5 and Comparative Examples 1 to 3 were measured, and the relative values for Comparative Example 3 are shown in Table 5.
[0439] Table 5
[0440]
[0441] Referring to the results in Table 5, it was found that the organic light-emitting devices of Examples 1 to 5 and Comparative Example 3 have high efficiency and / or long lifetime characteristics, and that the organic light-emitting devices of Comparative Examples 1 and 2 do not have light-emitting characteristics because there is no energy transfer to the dopant.
[0442] As is clear from the preceding description, the organic light-emitting device according to the embodiments can have high efficiency and high color purity.
Claims
1. Organic light-emitting devices, including: First electrode; Second electrode; as well as An organic layer comprising an emission layer is located between the first electrode and the second electrode. The emitter layer comprises a polycyclic compound represented by Formula 1 and a host, wherein the content of the polycyclic compound is less than the content of the host: Formula 1 Formula 1A Among them, in Equations 1 and 1A, Ar1 is a group represented by formula 1A. Cycles CY1 and CY2 are each independently C5-C. 30 Carbocyclic groups or C1-C 30 Heterocyclic groups, Y1 can be B, N, P, P (=O), P (=S), Al, Ga, As, Si (R5), or Ge (R5). X1 and X2 are each independently selected from O, S, Se, N(R6), C(R6)(R7), Si(R6)(R7), Ge(R6)(R7), and P(=O)(R6). L1and L 11 each independently is selected from a single bond, substituted or unsubstituted C5-C 30 carbocyclic group and substituted or unsubstituted C1-C 30 heterocyclic group, a1 and a11 are each independent integers from 1 to 3. when a1 is 2 or more, at least two L1are the same or different from each other, and when a11 is 2 or more, at least two L 11 are the same or different from each other, R1, R2, R3, R4, R5, R6, R7, R 11 and R 12 Each group is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C groups. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7), and -P(=O)(Q8)(Q9), R1and R2are optionally joined to form a substituted or unsubstituted C5-C 30 carbocyclic group or a substituted or unsubstituted C1-C 30 heterocyclic group, b1 and b2 are each independent integers between 0 and 10. When b1 is 2 or greater, at least two R1s are either the same or different from each other, and when b2 is 2 or greater, at least two R2s are either the same or different from each other. b11 is an integer between 1 and 5. when b11 is 2 or more, at least two R 11 the same as or different from each other, b12 is an integer from 1 to 8. when b12 is 2 or more, at least two R 12 the same as or different from one another, c11 is an integer from 1 to 8. when c11 is 2 or more, at least two -(L 11 ) a11 -(R 11 ) b11 each other or different, The sum of b12 and c11 is 9. Replacement C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthio-, substituted C7-C 60 Aryl groups, substituted C1-C 60 The heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and at least one substituent of the substituted monovalent non-aromatic fused heterocyclic group are selected from: Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, and C1-C 60 Alkoxy; Each is selected from at least one of the following C1-C substituted. 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, and C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 14 (Q) 15 -B(Q) 16 (Q) 17 ), and -P(=O)(Q 18 (Q) 19 ); C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups; Each is selected from at least one of the following C3-C substituted. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 24 (Q) 25 -B(Q) 26 (Q) 27 ), and -P(=O)(Q 28 (Q) 29 );and -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 34 )(Q 35 ), -B(Q 36 )(Q 37 ), and -P(=O)(Q 38 )(Q 39 ), Among them, Q1-Q9, Q 11 -Q 19 Q 21 -Q 29 , and Q 31 -Q 39 Each group is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C groups. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups. The polycyclic compound is a fluorescent emitter. The emission layer further includes a sensitizer that satisfies Equation 1: Equation 1 ΔΕ ST ≤ 0.3 eV wherein in equation 1, ΔE ST represents the energy gap between the lowest excited singlet state energy level (S1) and the lowest excited triplet state energy level (T1), Both the sensitizer and the polycyclic compound satisfy conditions 1 and 2: Condition 1 T 衰减 (PC)<T 衰减 (S) Condition 2 T 衰减 (PC) < 1.5 µs Among them, in conditions 1 and 2, T 衰减 (PC) represents the decay time of the polycyclic compound, and T 衰减 (S) represents the decay time of the sensitizer.
2. The organic light-emitting device as claimed in claim 1, wherein Y1 is B, and X1 and X2 are each independently selected from O, S, Se, N(R6), C(R6)(R7), and Si(R6)(R7).
3. The organic light-emitting device of claim 1, wherein CY1 and CY2 are each independently selected from A group, B group, a fused ring formed by the fusion of at least two groups selected from A group, a fused ring formed by the fusion of at least two groups selected from B group, and a fused ring formed by the fusion of at least one group selected from A group and at least one group selected from B group. wherein A groups are selected from the group consisting of cyclopenta-1,3-dienyl groups, indenyl groups, phenyl groups, naphthyl groups, anthracenyl groups, phenanthrenyl groups, naphthacenyl groups, butalyl groups, pyrenyl groups, phenanthrenyl groups, naphthacenyl groups, butalyl groups, pyrenyl groups, chrysenyl groups, fluoranthenyl groups, benz[9,10]phenanthrenyl groups, and fluorenyl groups, and The B group is selected from furan groups, thiophene groups, pyrrole groups, borocyclopentadienyl groups, thiophene groups, pyrrolidinyl groups, imidazole groups, thiazole groups, and triazole groups. azole group, iso- The following groups are included: azole group, isothiazole group, pyridine group, pyrimidine group, pyridazine group, triazine group, indole group, isoindole group, indazine group, quinoline group, isoquinoline group, quinoxaline group, isoquinoxaline group, carbazole group, dibenzofuran group, dibenzothiophene group, dibenzothiophene group, and dibenzoborone heterocyclopentadiene group.
4. The organic light-emitting device of claim 1, wherein CY1 and CY2 are each independently selected from phenyl groups, naphthyl groups, anthracene groups, and fluorene groups.
5. The organic light emitting device of claim 1, wherein L1and L 11 each is independently selected from the group consisting of: single bond; Phenylidene, indene, naphthylene, phenylene alkyl, heptadeneyl, acenaphthene, fluoreneyl, phenentheneyl, anthraceneyl, fluoreneyl, benzo[9,10]phenentheneyl, pyreneyl, and phenentheneyl base; and Each is substituted with at least one of the following: phenylene, indenylene, naphthylene, or phenylene oxide. alkyl, heptadeneyl, acenaphthene, fluoreneyl, phenenyl, anthraceneyl, fluoreneyl, benzo[9,10]phenenyl, pyreneyl, and phenenyl Groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups; and Each is substituted with at least one of the following: phenylene, indenylene, naphthylene, or phenylene oxide. alkyl, heptadeneyl, acenaphthene, fluoreneyl, phenenyl, anthraceneyl, fluoreneyl, benzo[9,10]phenenyl, pyreneyl, and phenenyl The radicals are each selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 At least one substituted phenyl, indenyl, or naphthyl group of a heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heterocyclic group. yl, heptalenyl, acenaphthyl, fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthyl, pyrene, and base.
6. The organic light emitting device of claim 1, wherein L1and L 11 is selected from a single bond and a group represented by one of Formulae 3-1 to 3-32: wherein In equations 3-1 to 3-32, Z 31 Selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl groups and C1-C 60 heteroaryl; and Each is selected from at least one of the following C3-C substituted. 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl groups and C1-C 60 Heteroaryl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 24 (Q) 25 -B(Q) 26 (Q) 27 ), and -P(=O)(Q 28 (Q) 29 ), e4 is an integer from 1 to 4. e6 is an integer from 1 to 6. e8 is an integer from 1 to 8, and and each represents a site of attachment to an adjacent atom.
7. The organic light-emitting device of claim 1, wherein R1 and R2 are each independently selected from: hydrogen, deuterium, -F, -CI, -Br, -I, hydroxyl, cyano (CN), nitro, amino, Ci-C 60 alkyl, and Ci-C 60 alkoxy; Each of the C1-Cs is replaced by at least one of the following: 60 Alkyl and C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano (CN), nitro, amino, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, and base; Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazineyl, dibenzofuranyl, dibenzothiophenylyl, and carbazoleyl; Each of the following is substituted with at least one of the following: cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthraceneyl, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, and carbazoleyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano (CN), nitro, amino, C1-C 60 Alkyl, C1-C 60 Alkoxy, C7-C 60 Aryl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, diazolyl, triazine, dibenzofuranyl, dibenzothiophene, carbazole, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 34 (Q) 35 -B(Q) 36 (Q) 37 ), and -P(=O)(Q 38 (Q) 39 );and -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7), and -P(=O)(Q8)(Q9).
8. The organic light-emitting device of claim 1, wherein at least one of R1 and R2 is selected from the groups represented by formulas 5-1 and 5-2: wherein, In equations 5-1 and 5-2, R 51 -R 55 each independently selected from the group consisting of: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, phenyl, biphenyl, and terphenyl; and Each of the following is substituted with at least one of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, and tert-hexyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, and phenyl. R 54 and R 55 optionally taken together with one another to form a heterocyclic ring, and b54 and b55 are each independent integers between 0 and 4.
9. The organic light-emitting device of claim 1, wherein R3 and R4 are each independently selected from: Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, and tert-hexyl; Each of the following is substituted with at least one of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, and tert-hexyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, and phenyl.
10. The organic light-emitting device of claim 1, wherein R3 and R4 are each hydrogen.
11. The organic light-emitting device of claim 1, wherein R5, R6, and R7 are each independently selected from: Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, and tert-hexyl; Each of the following is substituted with at least one of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, and tert-hexyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, and phenyl. Phenyl, biphenyl, naphthyl, fluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl; Each of the following is substituted with at least one of the following: phenyl, biphenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiopheneyl.
12. The organic light-emitting device as claimed in claim 1, wherein... R 11 selected from the group consisting of formulae 4-1 to 4-42; R 12 Selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, and tert-hexyl; and Each of the following is substituted with at least one of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, and tert-hexyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, and phenyl. wherein, In equations 4-1 to 4-42, Y 31 is O, S, C(Z 45 )(Z 46 ), N(Z 47 ), or Si(Z 48 )(Z 49 ), Z 41 -Z 49 each independently selected from the group consisting of: Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, C7-C 60 Aryl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazineyl, dibenzofuranyl, dibenzothiophenylyl, and carbazoleyl; Each of the following is substituted with at least one of the following: cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazine, dibenzofuranyl, dibenzothiopheneyl, and carbazoleyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkyl groups and cumyl groups, f3 is an integer between 1 and 3. f4 is an integer from 1 to 4. f5 is an integer between 1 and 5. f6 is an integer from 1 to 6. f7 is an integer from 1 to 7. f9 is an integer from 1 to 9, and represents a binding site to an adjacent atom.
13. The organic light-emitting device of claim 1, wherein formula 1A is selected from formulas 1A-1 to 1A-5: Among them, in equations 1A-1 to 1A-5, L 11 , a 11 , R 11 , and b 11 are each understood by reference to the description of L 11 , a 11 , R 11 , and b 11 in claim 1, respectively, R 21 -R 29 each by reference to the description of R 12 in claim 1, and represents a binding site to an adjacent atom.
14. The organic light-emitting device of claim 1, wherein the polycyclic compound comprises a compound represented by any one of formulas 2-1 to 2-8: wherein In equations 2-1 to 2-8, Y1, X1, X2, R1, R2, R3, R4, R5, L1, a1, and Ar1 are understood by reference to the descriptions of Y1, X1, X2, R1, R2, R3, R4, R5, L1, a1, and Ar1 in claim 1.
15. The organic light-emitting device of claim 1, wherein the polycyclic compound is selected from compounds 1 to 468: 。 16. The organic light-emitting device of claim 1, wherein the emitting layer further comprises a photoluminescent dopant, and the content of the host is greater than the content of the polycyclic compound and the photoluminescent dopant.
17. The organic light-emitting device of claim 1, wherein the first electrode is an anode, the second electrode is a cathode, the organic layer includes a hole transport region between the first electrode and the emitting layer and an electron transport region between the emitting layer and the second electrode, the hole transport region including a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and the electron transport region including a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
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