Light-emitting element, fused polycyclic compound for light-emitting element, display device including light-emitting element, and electronic device including light-emitting element
By using fused polycyclic compounds as emission layer materials in organic electroluminescent elements, the luminous efficiency and service life are improved, the problems of high driving voltage and low luminous efficiency in the prior art are solved, and an efficient display effect is achieved.
Patent Information
- Application Number
- CN202510234238.9
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2024-03-04
- Filing Date
- 2025-02-28
- Publication Date
- 2025-09-05
AI Technical Summary
Existing organic electroluminescent elements have shortcomings in terms of high driving voltage, low luminous efficiency and short service life, making it difficult to meet the needs of high-efficiency display.
A fused polycyclic compound is used as the emission layer material. By improving the structural design of the light-emitting element, including the first electrode, the second electrode and the emission layer, the fused polycyclic compound with a specific structure is used to improve the luminous efficiency and extend the service life.
The luminous efficiency and service life of the organic electroluminescent element are improved, and the display quality of the display device is enhanced.
Smart Images

Figure CN120590420A_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2024-0030963, filed on March 4, 2024, in the Korean Intellectual Property Office, the disclosure of which is incorporated herein by reference in its entirety. Technical Field
[0003] One or more embodiments of the present disclosure relate to a light-emitting element, a fused polycyclic compound for a light-emitting element, a display device including the light-emitting element, and an electronic device including the light-emitting element. Background Art
[0004] Recently, a lot of research and development work has been done on organic electroluminescent display devices as image display devices. Unlike liquid crystal display devices, organic electroluminescent display devices are self-luminous (i.e., self-luminous display devices). In these devices, holes and electrons are injected from a first electrode and a second electrode, respectively. These holes and electrons (charges) recombine in the emission layer of the organic electroluminescent display device, and the recombination causes the luminescent material including the organic compound in the emission layer to emit light, thereby realizing the display of an image.
[0005] When organic electroluminescent elements are applied to display devices, they are expected to exhibit (have) low driving voltage, high luminous efficiency, and long element life. Consequently, ongoing research and development is focused on materials for organic electroluminescent elements that can stably achieve (obtain) these desired characteristics.
[0006] In recent years, in order to realize efficient organic electroluminescent elements, technologies related to phosphorescence emission using triplet energy levels and / or technologies related to fluorescence emission using triplet-triplet annihilation (TTA), in which singlet excitons are generated by collision of triplet excitons, have been explored and developed. For example, thermally activated delayed fluorescence (TADF) materials that utilize the delayed fluorescence phenomenon are being actively researched and developed. Summary of the Invention
[0007] One or more aspects of the embodiments of the present disclosure are directed to a light emitting element in which light emitting efficiency and element life are improved.
[0008] One or more aspects of the embodiments of the present disclosure relate to a fused polycyclic compound capable of improving the luminous efficiency and service life of a light-emitting element.
[0009] One or more aspects of embodiments of the present disclosure relate to a display device including a light emitting element, in which light emitting efficiency and element lifespan are improved, thereby having excellent or appropriate display quality.
[0010] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the presented embodiments.
[0011] According to one or more embodiments of the present disclosure, a light-emitting element includes a first electrode, a second electrode opposite to the first electrode (e.g., facing the first electrode), and an emission layer between the first electrode and the second electrode, wherein the emission layer includes a fused polycyclic compound represented by Formula 1 as the first compound:
[0012] Formula 1
[0013]
[0014] In Formula 1, q, w and e may each independently be an integer selected from 0 to 3; r may be an integer selected from 0 to 2; q21, w31, e41 and r51 may each independently be an integer selected from 0 to 4; the sum of q, w, e and r is 1 or greater; if q is 0 (for example, when q is 0), q2 is an integer selected from 0 to 4, if q is 1 (for example, when q is 1), q2 is an integer selected from 0 to 2, and if q is 2 or 3 (for example, when q is 2 or 3), q2 is 0; if w is 0 (for example, when w is 0), w2 is an integer selected from 0 to 4, if w is 1 (for example, when w is 1), w 2 is an integer selected from 0 to 2, and if w is 2 or 3 (for example, when w is 2 or 3), w2 is 0; if e is 0 (for example, when e is 0), e2 is an integer selected from 0 to 4, if e is 1 (for example, when e is 1), e2 is an integer selected from 0 to 2, and if e is 2 or 3 (for example, when e is 2 or 3), e2 is 0; if r is 0 (for example, when r is 0), r2 is an integer selected from 0 to 3, if r is 1 (for example, when r is 1), r2 is 0 or 1, and if r is 2 (for example, when r is 2), r2 is 0; X1 may be O or S; X2 may be O, S or NT 20 ; and X3 can be O, S or NT 30 ; T1 may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms; T 20 、T 30 T, T2, T3, T4, T5 and T6 may each independently be hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms; and T 21 、T 31 、T 41 and T 51Each may independently be hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms and / or may independently bond with an adjacent group to form a ring.
[0015] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by Formula 1-1:
[0016] Formula 1-1
[0017]
[0018] In Formula 1-1, A may be hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms; a may be an integer selected from 0 to 9; and q, w, e, r, q21, w31, e41, r51, q2, w2, e2, r2, X1, X2, X3, T 20 、T 30 、T2、T3、T4、T5、T6、T 21 、T 31 、T 41 and T 51 may each independently be the same as defined in Formula 1.
[0019] In one or more embodiments, the fused polycyclic compound represented by Formula 1 as the first compound may be represented by Formula 2-1 or Formula 2-2:
[0020] Formula 2-1
[0021]
[0022] Formula 2-2
[0023]
[0024] In formula 2-1 and formula 2-2, q, w, e, r, q21, w31, e41, r51, q2, w2, e2, r2, T1, T 20 、T 30 、T2、T3、T4、T5、T6、T 21 、T 31 、T 41 and T 51 may each independently be the same as defined in Formula 1.
[0025] In one or more embodiments, in Formula 1, T1 may be a substituted or unsubstituted biphenyl group.
[0026] In one or more embodiments, in Formula 1, T1 may be an unsubstituted o-biphenyl group (ie, biphenyl-2-yl, T1 is an unsubstituted biphenyl group, and the unsubstituted biphenyl group is connected to the N atom via the 2-carbon atom thereof).
[0027] In one or more embodiments, in Formula 1, T 20 and T 30 Each of may be a substituted or unsubstituted terphenyl group.
[0028] In one or more embodiments, in Formula 1, T 20 and T 30 Each of may be an unsubstituted m-terphenyl group.
[0029] In one or more embodiments, the fused polycyclic compound represented by Formula 1 above as the first compound may be represented by any one selected from Formula 3-1 to Formula 3-7:
[0030] Formula 3-1
[0031]
[0032] Formula 3-2
[0033]
[0034] Formula 3-3
[0035]
[0036] Formula 3-4
[0037]
[0038] Formula 3-5
[0039]
[0040] Formula 3-6
[0041]
[0042] Formula 3-7
[0043]
[0044] In Equations 3-1 to 3-7, T 201 、T 202 、T 203 、T 204 、T 205、T 206 and T 207 each independently may be hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms and / or may be bonded with an adjacent group to form a ring, Q201, Q202, and Q203 may each independently be an integer selected from 0 to 6, Q204, Q205, Q206, and Q207 may each independently be an integer selected from 0 to 8, and W, E, R, W31, E41, R51, W2, E2, R2, X1, X2, X3, T1, T2 20 、T 30 、T3、T4、T5、T6、T 31 、T 41 and T 51 may each independently be the same as defined in Formula 1.
[0045] In one or more embodiments, the fused polycyclic compound represented by Formula 1 as the first compound may be represented by any one selected from Formula 4-1 to Formula 4-7:
[0046] Formula 4-1
[0047]
[0048] Formula 4-2
[0049]
[0050] Formula 4-3
[0051]
[0052] Formula 4-4
[0053]
[0054] Formula 4-5
[0055]
[0056] Formula 4-6
[0057]
[0058] Formula 4-7
[0059]
[0060] In equations 4-1 to 4-7, T 301 、T302 、T 303 、T 304 、T 305 、T 306 and T 307 may each independently be hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms and / or may be bonded with an adjacent group to form a ring, w301, w302 and w303 may each independently be an integer selected from 0 to 6, w304, w305, w306 and w307 may each independently be an integer selected from 0 to 8, and q, e, r, q21, e41, r51, q2, e2, r2, X1, X2, X3, T1, T2 20 、T 30 、T2、T4、T5、T6、T 21 、T 41 and T 51 may each independently be the same as defined in Formula 1.
[0061] In one or more embodiments, the fused polycyclic compound represented by Formula 1 as the first compound may be represented by any one selected from Formula 5-1 to Formula 5-7:
[0062] Formula 5-1
[0063]
[0064] Formula 5-2
[0065]
[0066] Formula 5-3
[0067]
[0068] Formula 5-4
[0069]
[0070] Formula 5-5
[0071]
[0072] Formula 5-6
[0073]
[0074] Formula 5-7
[0075]
[0076] In Equations 5-1 to 5-7, T 401 、T 402 、T 403 、T 404 、T 405 、T 406 and T 407 each independently may be hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms and / or may be bonded with an adjacent group to form a ring, e401, e402 and e403 may each independently be an integer selected from 0 to 6, e404, e405, e406 and e407 may each independently be an integer selected from 0 to 8, and q, w, r, q21, w31, r51, q2, w2, r2, X1, X2, X3, T1, T2 20 、T 30 、T2、T3、T5、T6、T 21 、T 31 and T 51 may each independently be the same as defined in Formula 1.
[0077] In one or more embodiments, the fused polycyclic compound represented by Formula 1 as the first compound may be represented by any one selected from Formula 6-1 to Formula 6-3:
[0078] Formula 6-1
[0079]
[0080] Formula 6-2
[0081]
[0082] Formula 6-3
[0083]
[0084] In the above formulas 6-1 to 6-3, T 501 To T 503Each of them may be independently hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, R501 and R502 may each be independently an integer selected from 0 to 5, R503 is an integer selected from 0 to 3, and Q, W, E, Q21, W31, E41, Q2, W2, E2, X1, X2, X3, T1, T2 20 、T 30 、T2、T3、T4、T6、T 21 、T 31 and T 41 may each independently be the same as defined in Formula 1.
[0085] In one or more embodiments, the emission layer may further include at least one of a second compound represented by Formula HT-1, a third compound represented by Formula ET-1, and a fourth compound represented by Formula D-1:
[0086] Formula HT-1
[0087]
[0088] In formula HT-1, M1 to M8 can each independently be N or CR 51 , L1 may be a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, Y a Can be direct connection, CR 52 R 53 or SiR 54 R 55 ,Ar a may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and R 51 to R 55 Each may independently be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted thiol, substituted or unsubstituted oxy, substituted or unsubstituted amino, substituted or unsubstituted boron, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 60 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 60 ring carbon atoms and / or may be bonded to an adjacent group to form a ring.
[0089] Formula ET-1
[0090]
[0091] In formula ET-1, Z a to Z c At least one of them can be N, and the rest can be CR 56 , R 56 may be hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, b1 to b3 may each independently be an integer selected from 0 to 10, Ar b to Ar d Each of L2 to L4 may be independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and each of L2 to L4 may be independently directly linked, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.
[0092] Formula D-1
[0093]
[0094] In formula D-1, Q1 to Q4 may each independently be C or N, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring group having 5 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 ring carbon atoms, X 11 To X 14 Can be directly connected or *-O-*, L 11 To L 13 Can be directly connected, *-O-*, *-S-*, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, -* refers to a portion connected to C1 to C4, b11 to b13 may each independently be 0 or 1, R 61 to R 66may each independently be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted thiol, substituted or unsubstituted oxy, substituted or unsubstituted amino, substituted or unsubstituted boron, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 60 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 60 ring carbon atoms, and / or selected from R 61 to R 66 One or more of d1 to d4 are independently bonded to an adjacent group to form a ring, and d1 to d4 may each be an integer selected from 0 to 4 independently.
[0095] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be any one selected from the compounds listed in Compound Group 1.
[0096] Compound Group 1
[0097]
[0098]
[0099]
[0100]
[0101]
[0102]
[0103]
[0104]
[0105]
[0106]
[0107]
[0108]
[0109]
[0110]
[0111]
[0112]
[0113]
[0114]
[0115]
[0116]
[0117]
[0118] According to one or more embodiments of the present disclosure, a display device includes a substrate layer, a circuit layer on the substrate layer, and a display element layer arranged on the circuit layer and including a light-emitting element, wherein the light-emitting element includes a first electrode, a second electrode on the first electrode, and an emission layer between the first electrode and the second electrode and including a fused polycyclic compound represented by Formula 1 as a first compound.
[0119] Formula 1
[0120]
[0121] In Formula 1, q, w, and e may each independently be an integer selected from 0 to 3, r may be an integer selected from 0 to 2, q21, w31, e41, and r51 may each independently be an integer selected from 0 to 4, the sum of q, w, e, and r is 1 or greater, if q is 0 (for example, when q is 0), q2 is an integer selected from 0 to 4, if q is 1 (for example, when q is 1), q2 is an integer selected from 0 to 2, and if q is 2 or 3 (for example, when q is 2 or 3), q2 is 0, if w is 0 (for example, when w is 0), w2 is an integer selected from 0 to 4, if w is 1 (for example, when w is 1), w2 is an integer selected from 0 to 2, and if w is 2 or 3 (for example, when w is 2 or 3), w2 is 0, if e is 0 (for example, when e is 0), e2 is an integer selected from 0 to 4, if e is 1 (for example, when e is 1), e2 is an integer selected from 0 to 2, and if e is 2 or 3 (for example, when e is 2 or 3), e2 is 0, if r is 0 (for example, when r is 0), r2 is an integer selected from 0 to 3, and if r is 1 (for example, when r is 1), r2 is 0 or 1, and if r is 2 (for example, when r is 2), r2 is 0, X1 may be O or S, and X2 may be O, S or NT 20 , and X3 can be O, S or NT 30 , T1 may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, T 20 、T 30T2, T3, T4, T5 and T6 may each independently be hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, and T 21 、T 31 、T 41 and T 51 Each may independently be hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms and / or may independently bond with an adjacent group to form a ring.
[0122] In one or more embodiments, the light emitting element may further include a capping layer on the second electrode, and the capping layer may have a refractive index of about 1.6 or greater with respect to light in a wavelength range of about 550 nanometers (nm) to about 660 nm.
[0123] In one or more embodiments, the display device may further include a light control layer on the display element layer and including quantum dots, wherein the light emitting element may emit a first color light, and the light control layer may include: a first light control component including first quantum dots configured to convert the first color light into a second color light having a longer wavelength than the wavelength of the first color light; a second light control component including second quantum dots configured to convert the first color light into a third color light having a longer wavelength than the wavelength of each of the first color light and the second color light; and a third light control component configured to transmit the first color light.
[0124] In one or more embodiments, the display device may further include a color filter layer on the light control layer, wherein the color filter layer may include a first color filter configured to transmit a second color light, a second color filter configured to transmit a third color light, and a third color filter configured to transmit the first color light.
[0125] According to one or more embodiments of the present disclosure, there is provided a fused polycyclic compound represented by Formula 1:
[0126] Formula 1
[0127]
[0128] In Formula 1, q, w and e may each independently be an integer selected from 0 to 3, r may be an integer selected from 0 to 2, q21, w31, e41 and r51 may each independently be an integer selected from 0 to 4, the sum of q, w, e and r is 1 or greater, if q is 0 (for example, when q is 0), q2 is an integer selected from 0 to 4, if q is 1 (for example, when q is 1), q2 is an integer selected from 0 to 2, and if q is 2 or 3 (for example, when q is 2 or 3), q2 is 0, if w is 0 (for example, when w is 0), w2 is an integer selected from 0 to 4, if w is 1 (for example, when w is 1), w2 is an integer selected from 0 to 2, and if w is 2 or 3 (for example, when w is 2 or 3), w2 is 0, if e is 0 (for example, when e is 0), e2 is an integer selected from 0 to 4, if e is 1 (for example, when e is 1), e2 is an integer selected from 0 to 2, and if e is 2 or 3 (for example, when e is 2 or 3), e2 is 0, if r is 0 (for example, when r is 0), r2 is an integer selected from 0 to 3, and if r is 1 (for example, when r is 1), r2 is 0 or 1, and if r is 2 (for example, when r is 2), r2 is 0, X1 may be O or S, and X2 may be O, S or NT 20 , and X3 can be O, S or NT 30 , T1 may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, T 20 、T 30 T2, T3, T4, T5 and T6 may each independently be hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, and T 21 、T 31 、T 41 and T 51 Each may independently be hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms and / or may independently bond with an adjacent group to form a ring.
[0129] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by Formula 1-1:
[0130] Formula 1-1
[0131]
[0132] In Formula 1-1, A may be hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, a may be an integer selected from 0 to 9, and q, w, e, r, q21, w31, e41, r51, q2, w2, e2, r2, X1, X2, X3, T 20 、T 30 、T2、T3、T4、T5、T6、T 21 、T 31 、T 41 and T 51 may each independently be the same as defined in Formula 1.
[0133] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by Formula 2-1 or Formula 2-2:
[0134] Formula 2-1
[0135]
[0136] Formula 2-2
[0137]
[0138] In formula 2-1 and formula 2-2, q, w, e, r, q21, w31, e41, r51, q2, w2, e2, r2, T1, T 20 、T 30 、T2、T3、T4、T5、T6、T 21 、T 31 、T 41 and T 51 may each independently be the same as defined in Formula 1.
[0139] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by any one selected from Formula 3-1 to Formula 3-7:
[0140] Formula 3-1
[0141]
[0142] Formula 3-2
[0143]
[0144] Formula 3-3
[0145]
[0146] Formula 3-4
[0147]
[0148] Formula 3-5
[0149]
[0150] [Formula 3-6]
[0151]
[0152] Formula 3-7
[0153]
[0154] In Equations 3-1 to 3-7, T 201 、T 202 、T 203 、T 204 、T 205 、T 206 and T 207 each independently may be hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms and / or may be independently bonded to an adjacent group to form a ring, Q201, Q202, and Q203 may each independently be an integer selected from 0 to 6, Q204, Q205, Q206, and Q207 may each independently be an integer selected from 0 to 8, and W, E, R, W31, E41, R51, W2, E2, R2, X1, X2, X3, T1, T2 20 、T 30 、T3、T4、T5、T6、T 31 、T 41 and T 51 may each independently be the same as defined in Formula 1. BRIEF DESCRIPTION OF THE DRAWINGS
[0155] The accompanying drawings are included to provide a further understanding of the present disclosure and are incorporated into and constitute a part of this disclosure. The accompanying drawings illustrate example embodiments of the present disclosure and, together with the description, serve to explain the principles of the present disclosure. The above and / or other aspects of the present disclosure should become apparent from the following description of the embodiments in conjunction with the accompanying drawings, and the above and / or other aspects of the present disclosure should be understood from the following description of the embodiments in conjunction with the accompanying drawings. In the drawings:
[0156] Figure 1is a plan view of a display device according to one or more embodiments of the present disclosure;
[0157] Figure 2 is a cross-sectional view of a display device according to one or more embodiments of the present disclosure;
[0158] Figure 3 A cross-sectional view schematically illustrating a light emitting element according to one or more embodiments of the present disclosure;
[0159] Figure 4 A cross-sectional view schematically illustrating a light emitting element according to one or more embodiments of the present disclosure;
[0160] Figure 5 A cross-sectional view schematically illustrating a light emitting element according to one or more embodiments of the present disclosure;
[0161] Figure 6 A cross-sectional view schematically illustrating a light emitting element according to one or more embodiments of the present disclosure;
[0162] Figure 7 and Figure 8 Each is a cross-sectional view of a display device according to one or more embodiments of the present disclosure;
[0163] Figure 9 A cross-sectional view illustrating a display device according to one or more embodiments of the present disclosure;
[0164] Figure 10 A cross-sectional view illustrating a display device according to one or more embodiments of the present disclosure; and
[0165] Figure 11 A view for explaining a vehicle in which a display device is arranged according to one or more embodiments of the present disclosure. DETAILED DESCRIPTION
[0166] The present disclosure may be modified in one or more suitable ways and has many forms, and therefore will be exemplified in the drawings and described in more detail in the detailed description of the present disclosure. However, it should be understood that the present disclosure is not intended to be limited to the specific forms disclosed, but rather is intended to cover all modifications, equivalents, and alternatives that fall within the spirit and scope of the present disclosure.
[0167] When explaining each drawing, the same reference numerals are used to refer to the same elements. In the accompanying drawings, for the sake of clarity of the present disclosure, the size of each structure may be magnified for illustration. It will be understood that although the terms "first" and / or "second" etc. may be used in this article to describe one or more appropriate components, these components should not be limited by these terms. These terms are merely used to distinguish one component from another. For example, without departing from the scope of the example embodiments of the present disclosure, the first component may be referred to as the second component, and similarly, the second component may be referred to as the first component. As used herein, unless the context clearly indicates otherwise, the singular forms "a", "an", "one" and "said" are intended to also include plural forms. Further, when describing an embodiment of the present disclosure, the use of "may" refers to "one or more embodiments of the present disclosure".
[0168] In the present disclosure, it will be understood that the terms "comprise(s) / comprising", "include(s) / including", and / or "have(has) / having", etc. indicate the presence of features, quantities, steps, operations, components, parts, and / or one or more combinations thereof (e.g., any appropriate combination) disclosed in the present disclosure, but do not exclude the possibility of the presence or addition of one or more other features, quantities, steps, operations, components, parts, and / or one or more combinations thereof (e.g., any appropriate combination). As used herein, the terms "and", "or", and "and / or" may include any and all combinations of one or more associated listed items. Expressions such as "at least one of", "one of", and "selected from..." when preceding / following a list of elements modify the entire list of elements and do not modify the individual elements of the list. For example, "at least one of a, b, and c," "at least one selected from a, b, and c," and / or "at least one selected from a to c," etc., may indicate only a, only b, only c, both a and b (e.g., a and b simultaneously), both a and c (e.g., a and c simultaneously), both b and c (e.g., b and c simultaneously), all of a, b, and c, or variations thereof. " / " as used herein may be interpreted as "and" or "or," depending on the context.
[0169] In the present disclosure, if a layer, film, region or plate is referred to as being “on” or “in the upper part” of another layer, film, region or plate (for example, when a layer, film, region or plate is referred to as being “on” or “in the upper part” of another layer, film, region or plate), it may not only be “directly on” the layer, film, region or plate, but one or more intervening layers, films, regions or plates may also be present therebetween. In contrast, if a layer, film, region or plate is referred to as being “under” or “under” another layer, film, region or plate (for example, when a layer, film, region or plate is referred to as being “under” or “under” another layer, film, region or plate), it may not only be directly under the layer, film, region or plate, but one or more intervening layers, films, regions or plates may also be present therebetween. In addition, it will be understood that if a component is referred to as being "on" another component (for example, when a component is referred to as being "on" another component), it can be disposed above the other component or also disposed below the other component. In contrast, "directly on..." can mean that there are no additional layers, films, regions, panels, etc. between the layer, film, region, panel, etc. and the other component. For example, "directly on..." can mean that two layers or two components are disposed without utilizing another component (for example, an adhesive component) between the two layers or two components.
[0170] In the present disclosure, the term "substituted or unsubstituted" may refer to being unsubstituted or substituted with at least one substituent selected from the group consisting of deuterium, halogen, cyano, nitro, amino, amine, silyl, oxy, sulfenyl, sulfinyl, sulfonyl, carbonyl, boron, phosphine oxide, phosphine sulfide, alkyl, alkenyl, alkynyl, hydrocarbon ring, aryl, and heterocyclic groups. In addition, each of the substituents exemplified above may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group or a phenyl group substituted with a phenyl group.
[0171] In the present disclosure, the phrase "bonding to an adjacent group to form a ring" may refer to a group bonding to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. Hydrocarbon rings include aliphatic hydrocarbon rings and / or aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and / or aromatic heterocycles. The hydrocarbon ring and heterocycle may each be monocyclic or polycyclic. In addition, the ring formed by bonding to each other may be connected to another ring to form a spiro structure.
[0172] In the present disclosure, the term "adjacent group" may refer to a substituent that replaces an atom directly connected to the atom substituted by the corresponding substituent, another substituent that replaces the atom substituted by the corresponding substituent, or a substituent that is spatially closest to the corresponding substituent. For example, the two methyl groups in 1,2-dimethylbenzene can be interpreted as "adjacent groups" to each other, and the two ethyl groups in 1,1-diethylcyclopentane can be interpreted as "adjacent groups" to each other. In addition, the two methyl groups in 4,5-dimethylphenanthrene can be interpreted as "adjacent groups" to each other.
[0173] In the present disclosure, examples of halogen may include fluorine, chlorine, bromine, or iodine.
[0174] In the present disclosure, the alkyl group may be linear or branched. The number of carbon atoms in the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of the alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, n-nonyl, n-decyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecanyl, and n-dodecanyl. alkyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl and / or n-triacontyl, etc., but embodiments of the present disclosure are not limited thereto.
[0175] In the present disclosure, a cycloalkyl group may refer to a cyclic alkyl group. The number of carbon atoms in the cycloalkyl group may be 3 to 50, 3 to 30, 3 to 20, or 3 to 10. Examples of cycloalkyl groups may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, 1-adamantyl, 2-adamantyl, isobornyl, and / or bicycloheptyl, but embodiments of the present disclosure are not limited thereto.
[0176] In the present disclosure, an alkenyl group refers to a hydrocarbon group having at least one carbon-carbon double bond in the middle or at the end of an alkyl group having 2 or more carbon atoms. The alkenyl group may be linear or branched. The number of carbon atoms in the alkenyl group is not particularly limited, and for example, may be 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl, and / or styrylvinyl, but embodiments of the present disclosure are not limited thereto.
[0177] In the present disclosure, an alkynyl group refers to a hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the end of an alkyl group having 2 or more carbon atoms. The alkynyl group may be linear or branched. Although the number of carbon atoms in the alkynyl group is not particularly limited, it may be 2 to 30, 2 to 20, or 2 to 10. Examples of alkynyl groups may include ethynyl and / or propynyl, etc., but embodiments of the present disclosure are not limited thereto.
[0178] In the present disclosure, the hydrocarbon ring group refers to any functional group or substituent derived from an aliphatic hydrocarbon ring. The hydrocarbon ring group may be a saturated hydrocarbon ring group having 5 to 20 ring-forming carbon atoms.
[0179] In the present disclosure, an aryl group refers to any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring carbon atoms in the aryl group may be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentyl, hexyl, triphenylene, pyrenyl, benzofluoranthenyl, and / or 1,2-triphenylenyl, but embodiments of the present disclosure are not limited thereto.
[0180] In the present disclosure, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Examples of substituted fluorenyl groups are as follows. However, embodiments of the present disclosure are not limited thereto.
[0181]
[0182] As used herein, a heterocyclic group refers to any functional group or substituent derived from a ring containing at least one of B, O, N, P, Si, S, and Se as a heteroatom. The heterocyclic group may include an aliphatic heterocyclic group and / or an aromatic heterocyclic group. The aromatic heterocyclic group may be a heteroaryl group. The aliphatic heterocyclic group and the aromatic heterocyclic group may each be monocyclic or polycyclic.
[0183] In the present disclosure, the heterocyclic group may contain at least one of B, O, N, P, Si, S and Se as a heteroatom. If the heterocyclic group contains two or more heteroatoms (for example, when the heterocyclic group contains two or more heteroatoms), the two or more heteroatoms may be the same or different from each other. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and includes heteroaryl groups. The number of ring carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20 or 2 to 10.
[0184] In the present disclosure, the aliphatic heterocyclic group may include at least one of B, O, N, P, Si, S, and Se as a heteroatom. The number of ring carbon atoms in the aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of the aliphatic heterocyclic group may include an oxiranyl group, a thiirane group, a pyrrolidinyl group, a piperidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, a thianyl group, a tetrahydropyranyl group, and / or a 1,4-dioxanyl group, but embodiments of the present disclosure are not limited thereto.
[0185] In the present disclosure, the heteroaryl group may contain at least one of B, O, N, P, Si, S and Se as a heteroatom. If the heteroaryl group contains two or more heteroatoms (for example, when the heteroaryl group contains two or more heteroatoms), the two or more heteroatoms may be the same or different from each other. The heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring carbon atoms in the heteroaryl group may be 2 to 30, 2 to 20 or 2 to 10. Examples of heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothiphenyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiadiazolyl, phenothiazinyl, dibenzothiaryl and / or dibenzofuranyl, but embodiments of the present disclosure are not limited thereto.
[0186] In the present disclosure, the above description of an aryl group can be applied to an arylene group, except that the arylene group is a divalent group. The above description of a heteroaryl group can be applied to a heteroarylene group, except that the heteroarylene group is a divalent group.
[0187] In the present disclosure, the silyl group may include an alkylsilyl group and / or an arylsilyl group. The alkyl group in the alkylsilyl group may be linear, branched or cyclic. The number of carbon atoms in the alkylsilyl group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylsilyl group is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of silyl groups may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl and / or phenylsilyl, but embodiments of the present disclosure are not limited thereto.
[0188] In the present disclosure, the number of carbon atoms in the carbonyl group is not particularly limited, but may be 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group may have the following structure, but embodiments of the present disclosure are not limited thereto.
[0189]
[0190] In the present disclosure, the number of carbon atoms in the sulfinyl group or the sulfonyl group is not particularly limited, and for example, may be 1 to 30. The sulfinyl group may include an alkylsulfinyl group and / or an arylsulfinyl group. The sulfonyl group may include an alkylsulfonyl group and / or an arylsulfonyl group.
[0191] In the present disclosure, a thio group may include an alkylthio group and / or an arylthio group. A thio group may refer to a sulfur atom bonded to an alkyl group or an aryl group as defined above. The alkyl group in the alkylthio group may be linear, branched, or cyclic. The number of carbon atoms in the alkylthio group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylthio group is not specifically limited, but may be, for example, 6 to 30, 6 to 20, or 6 to 15. Examples of thio groups may include methylthio, ethylthio, propylthio, pentylthio, hexylthio, octylthio, dodecylthio, cyclopentylthio, cyclohexylthio, phenylthio, and naphthylthio, but embodiments of the present disclosure are not limited thereto.
[0192] In the present disclosure, an oxy group may refer to an oxygen atom bonded to an alkyl group or an aryl group as defined above. The oxy group may include an alkoxy group and / or an aryloxy group. The alkoxy group may be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the aryloxy group is not specifically limited, but may be, for example, 6 to 30, 6 to 20, or 6 to 15. Examples of oxy groups may include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, and / or benzyloxy, but embodiments of the present disclosure are not limited thereto.
[0193] As used herein, a boryl group may refer to a boron atom bonded to an alkyl or aryl group as defined above. Boryl groups include alkylboryl groups and / or arylboryl groups. The alkyl group in the alkylboryl group may be linear, branched, or cyclic. The number of carbon atoms in the alkylboryl group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylboryl group is not specifically limited, but may be, for example, 6 to 30, 6 to 20, or 6 to 15. Examples of boryl groups may include dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl, and / or phenylboryl, but embodiments of the present disclosure are not limited thereto.
[0194] In the present disclosure, the number of carbon atoms in the amine group is not specifically limited, for example, it can be 1 to 30. The amine group can include an alkylamine group and / or an arylamine group. The alkyl group in the alkylamine group can be linear, branched or cyclic. The number of carbon atoms in the alkylamine group is not specifically limited, but can be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylamine group is not specifically limited, but can be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of amine groups can include methylamine, dimethylamine, phenylamine, diphenylamine, naphthylamine and / or 9-methyl-anthrylamine, etc., but embodiments of the present disclosure are not limited thereto. In the present disclosure, the term "amine group" is used interchangeably with the term "amino group".
[0195] In the specification, a sulfinyl group may refer to -S(=O)- combined with an alkyl group or an aryl group as defined above. The number of carbon atoms of the sulfinyl group is not particularly limited, but may be 1 to 30, 1 to 20, or 1 to 10. The sulfinyl group may include an alkylsulfinyl group and an arylsulfinyl group. For example, the sulfinyl group may have the following structure, but is not limited thereto.
[0196]
[0197] In the specification, a sulfonyl group may refer to -S(=O)2- combined with an alkyl group or an aryl group as defined above. The number of carbon atoms in the sulfonyl group is not particularly limited, but may be 1 to 30, 1 to 20, or 1 to 10. The sulfonyl group may include an alkylsulfonyl group and an arylsulfonyl group. For example, the sulfonyl group may have the following structure, but is not limited thereto.
[0198]
[0199] In the specification, the phosphine oxide group may mean -P(=O)- combined with the alkyl group or aryl group defined above. The number of carbon atoms of the phosphine oxide group is not particularly limited, but may be 1 to 30, 1 to 20, or 1 to 10. The phosphine oxide group may include an alkyl phosphine oxide group and an aryl phosphine oxide group. For example, the phosphine oxide group may have the following structure, but is not limited thereto.
[0200]
[0201] In the specification, the phosphinyl sulfide group may refer to -P(=S)- combined with an alkyl group or an aryl group as defined above. The number of carbon atoms in the phosphinyl sulfide group is not particularly limited, but may be 1 to 30, 1 to 20, or 1 to 10. The phosphinyl sulfide group may include an alkylphosphinyl sulfide group and an arylphosphinyl sulfide group. For example, the phosphinyl sulfide group may have the following structure, but is not limited thereto.
[0202]
[0203] In the present disclosure, the alkyl group in the alkoxy group, alkylthio group, alkylsulfonyl group, alkylsulfinyl group, alkylaryl group, alkylamino group, alkylboryl group, alkylsilyl group, alkylphosphine oxide group, alkylphosphine sulfide group, and alkylamine group may be the same as exemplified above.
[0204] In the present disclosure, the aryl group in the aryloxy group, arylthio group, arylsulfonyl group, arylsulfinyl group, arylamino group, arylboryl group, arylsilyl group, arylphosphine oxide group, arylphosphine sulfide group, and arylamine group may be the same as exemplified above.
[0205] In this disclosure, a direct connection may refer to a single bond.
[0206] In this disclosure, and "-*" each refer to the location to be linked.
[0207] In the specification, “an integer selected from 0 to 10” refers to an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10. The description of the above numerical range is also applicable to any other numerical range appearing in the specification, for example, an integer selected from 0 and 1, an integer selected from 0 to 2, an integer selected from 0 to 3, an integer selected from 0 to 4, an integer selected from 0 to 5, an integer selected from 0 to 6, an integer selected from 0 to 7, an integer selected from 0 to 8 and an integer selected from 0 to 9, etc.
[0208] Hereinafter, exemplary embodiments of the present disclosure will be described in more detail with reference to the accompanying drawings. In the present disclosure, the term "display device" may be used interchangeably with "display apparatus," and the term "light emitting device" may be used interchangeably with the term "light emitting element."
[0209] Figure 1 1 is a plan view illustrating a display device DD according to one or more embodiments of the present disclosure. Figure 2 is a cross-sectional view of a display device DD according to one or more embodiments. Figure 2 To explain the Figure 1 1 is a cross-sectional view of a portion of the display device DD taken along line II'.
[0210] The display device DD may include a display panel DP and an optical layer PP disposed on the display panel DP. The display panel DP may include light-emitting devices ED-1, ED-2, and ED-3. The display device DD may include a plurality of light-emitting devices ED-1, ED-2, and ED-3. The optical layer PP may be disposed on the display panel DP to control light reflected in the display panel DP due to external light. The optical layer PP may include, for example, a polarizing layer and / or a color filter layer. In one or more embodiments, the optical layer PP may not be provided in the display device DD.
[0211] The base substrate BL may be disposed on the optical layer PP. The base substrate BL may be a member providing a base surface, and the optical layer PP is disposed on the base surface. The base substrate BL may be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, embodiments of the present disclosure are not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. In one or more embodiments, the base substrate BL may not be provided.
[0212] The display device DD according to one or more embodiments may further include a filling layer. The filling layer may be disposed between the display device layer DP-ED and the base substrate BL. The filling layer may be an organic material layer. The filling layer may include at least one of an acrylic resin, a silicone resin, and an epoxy resin.
[0213] The display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display device layer DP-ED. The display device layer (also referred to as a display element layer) DP-ED may include a pixel defining film PDL, light-emitting devices ED-1, ED-2, and ED-3 arranged between respective portions of the pixel defining film PDL, and an encapsulation layer TFE arranged on the light-emitting devices ED-1, ED-2, and ED-3.
[0214] The base layer BS may be a member that provides a base surface, and the display device layer DP-ED is arranged on the base surface. The base layer BS may be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, the embodiments of the present disclosure are not limited thereto, and the base layer BS may be an inorganic layer, an organic layer, or a composite material layer.
[0215] In one or more embodiments, the circuit layer DP-CL may be disposed on the base layer BS, and the circuit layer DP-CL may include a plurality of transistors. Each of the plurality of transistors may include a control electrode, an input electrode, and an output electrode. For example, in one or more embodiments, the circuit layer DP-CL may include switching transistors and driving transistors for driving the light-emitting devices ED-1, ED-2, and ED-3 of the display device layer DP-ED.
[0216] Each of the light emitting devices ED-1, ED-2, and ED-3 may have a configuration according to a method described in more detail later. Figures 3 to 6 Each of the light-emitting devices ED-1, ED-2, and ED-3 may include a first electrode EL1, a hole transport region HTR, respective emission layers EML-R, EML-G, and EML-B, an electron transport region ETR, and a second electrode EL2.
[0217] Figure 2 An embodiment is illustrated in which the emission layers EML-R, EML-G, and EML-B of the light-emitting devices ED-1, ED-2, and ED-3, respectively, are arranged in the openings OH defined in the pixel-defining film PDL, and the hole transport region HTR, the electron transport region ETR, and the second electrode EL2 are each provided as a common layer in the entire light-emitting devices ED-1, ED-2, and ED-3. However, the embodiments of the present disclosure are not limited thereto, and for example, in one or more embodiments, the hole transport region HTR and the electron transport region ETR may each be provided by patterning inside the openings OH defined in the pixel-defining film PDL. For example, in one or more embodiments, the hole transport region HTR of the light-emitting devices ED-1, ED-2, and ED-3, the emission layers EML-R, EML-G, and EML-B, and the electron transport region ETR may be provided by patterning using an inkjet printing method.
[0218] The encapsulation layer TFE may cover the light-emitting devices ED-1, ED-2, and ED-3. The encapsulation layer TFE may seal the light-emitting elements ED-1, ED-2, and ED-3 in the display device layer DP-ED. The encapsulation layer TFE may be a thin film encapsulation layer. The encapsulation layer TFE may be formed by laminating one or more layers. The encapsulation layer TFE may include at least one insulating layer. The encapsulation layer TFE according to one or more embodiments may include at least one inorganic film (hereinafter, encapsulation-inorganic film). The encapsulation layer TFE according to one or more embodiments may include at least one organic film (hereinafter, encapsulation-organic film) and at least one encapsulation-inorganic film.
[0219] The encapsulation-inorganic film protects the display device layer DP-ED from moisture / oxygen, and the encapsulation-organic film protects the display device layer DP-ED from foreign matter (e.g., dust particles). The encapsulation-inorganic film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, and / or aluminum oxide, etc., but the embodiments of the present disclosure are not specifically limited thereto. In one or more embodiments, the encapsulation-organic film may include an acrylic compound and / or an epoxy compound, etc. In one or more embodiments, the encapsulation-organic film may include a photopolymerizable organic material, but the embodiments of the present disclosure are not specifically limited thereto.
[0220] The encapsulation layer TFE may be disposed on the second electrode EL2 and may be disposed to fill the open holes OH.
[0221] refer to Figure 1 and Figure 2 , the display device DD may include a non-emission area NPXA and emission areas PXA-R, PXA-G, and PXA-B. The emission areas PXA-R, PXA-G, and PXA-B may be areas where light generated by the respective light-emitting devices ED-1, ED-2, and ED-3 is emitted. On a plane (e.g., in a plan view), the emission areas PXA-R, PXA-G, and PXA-B may be spaced and / or separated (e.g., spaced apart or separated) from each other.
[0222] Each of the light-emitting areas PXA-R, PXA-G, and PXA-B may be an area divided by a pixel-defining film PDL. The non-light-emitting area NPXA may be an area between adjacent light-emitting areas PXA-R, PXA-G, and PXA-B, corresponding to the pixel-defining film PDL. In one or more embodiments, the light-emitting areas PXA-R, PXA-G, and PXA-B may correspond to pixels, respectively. The pixel-defining film PDL may divide the light-emitting devices ED-1, ED-2, and ED-3. The respective emission layers EML-R, EML-G, and EML-B of the light-emitting devices ED-1, ED-2, and ED-3 may be arranged in the openings OH defined in the pixel-defining film PDL and separated from each other.
[0223] The light emitting areas PXA-R, PXA-G, and PXA-B may be divided into a plurality of groups according to the colors of the lights generated from the light emitting devices ED-1, ED-2, and ED-3. Figure 1 and Figure 2 In the display device DD of one or more embodiments described in the accompanying drawings, three light-emitting regions PXA-R, PXA-G, and PXA-B that emit red, green, and blue light, respectively, are schematically illustrated. For example, the display device DD of one or more embodiments may include a red light-emitting region PXA-R, a green light-emitting region PXA-G, and a blue light-emitting region PXA-B that are separated from each other.
[0224] In a display device DD according to one or more embodiments, a plurality of light-emitting devices ED-1, ED-2, and ED-3 may emit light beams having different wavelength ranges. For example, in one or more embodiments, the display device DD may include a first light-emitting device ED-1 that emits red light, a second light-emitting device ED-2 that emits green light, and a third light-emitting device ED-3 that emits blue light. For example, in one or more embodiments, the red light-emitting region PXA-R, the green light-emitting region PXA-G, and the blue light-emitting region PXA-B of the display device DD may correspond to the first light-emitting device ED-1, the second light-emitting device ED-2, and the third light-emitting device ED-3, respectively.
[0225] However, the embodiments of the present disclosure are not limited thereto, and the first to third light-emitting devices ED-1, ED-2, and ED-3 may emit light beams in substantially the same wavelength range, or at least one light-emitting device may emit light beams in a wavelength range different from that of the other light-emitting devices. For example, in one or more embodiments, the first to third light-emitting devices ED-1, ED-2, and ED-3 may all emit blue light.
[0226] The light emitting regions PXA-R, PXA-G, and PXA-B in the display device DD according to one or more embodiments may be arranged in a stripe form. Figure 1 , a plurality of red light-emitting areas PXA-R may be arranged along the second direction axis DR2, a plurality of green light-emitting areas PXA-G may be arranged along the second direction axis DR2, and a plurality of blue light-emitting areas PXA-B may be arranged along the second direction axis DR2. In addition, the red light-emitting areas PXA-R, the green light-emitting areas PXA-G, and the blue light-emitting areas PXA-B may be alternately arranged along the first direction axis DR1 in the following order.
[0227] Figure 1 and Figure 2 While all of the light-emitting regions PXA-R, PXA-G, and PXA-B have been described as having the same area, embodiments of the present disclosure are not limited thereto. Therefore, the light-emitting regions PXA-R, PXA-G, and PXA-B may have different areas depending on the wavelength range of the emitted light. In this regard, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may refer to areas when viewed on a plane defined by the first and second direction axes DR1 and DR2 (e.g., areas in a plan view). The third direction axis DR3 may be perpendicular to the plane defined by the first and second direction axes DR1 and DR2.
[0228] In one or more embodiments, the arrangement of the light emitting areas PXA-R, PXA-G, and PXA-B is not limited to Figure 1 The configuration explained in the above description may be provided, and the order of arranging the red light-emitting areas PXA-R, the green light-emitting areas PXA-G, and the blue light-emitting areas PXA-B may be provided in one or more appropriate combinations according to the characteristics of the display quality desired or required in the display device DD. For example, in one or more embodiments, the arrangement of the light-emitting areas PXA-R, PXA-G, and PXA-B may be in a honeycomb pattern. Arrangement form (eg, RGBG matrix, RGBG structure or RGBG matrix structure) or diamond Arrangement format (e.g., a display (e.g., an OLED display) containing red, blue, and green (RGB) light-emitting regions arranged in a diamond shape). Diamond is a registered trademark of Samsung Display Co., Ltd. is a trademark of Samsung Display Co., Ltd.
[0229] In one or more embodiments, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may be different from each other. For example, in one or more embodiments, the area of the green light-emitting region PXA-G may be smaller than the area of the blue light-emitting region PXA-B, but the embodiments of the present disclosure are not limited thereto.
[0230] Below, Figures 3 to 6 Each is a cross-sectional view schematically illustrating a light-emitting element ED according to one or more embodiments of the present disclosure. Each light-emitting element ED according to one or more embodiments may include a first electrode EL1, a second electrode EL2 opposing the first electrode EL1 (e.g., the second electrode EL2 facing the first electrode EL1), and at least one functional layer disposed between the first electrode EL1 and the second electrode EL2. The light-emitting element ED according to one or more embodiments may include a fused polycyclic compound according to one or more embodiments, which will be described in more detail later, in at least one functional layer.
[0231] Figures 3 to 6 Each of the light-emitting elements ED explained in the embodiment may include a hole transport region HTR, an emission layer EML, and an electron transport region ETR stacked in sequence (e.g., stacked in the order described) as at least one functional layer. For example, each of the light-emitting elements ED of the embodiment may include a first electrode EL1, a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode EL2 stacked in sequence (e.g., stacked in the order described).
[0232] and Figure 3 compared to, Figure 4 A cross-sectional view of a light emitting element ED according to one or more embodiments is illustrated, wherein the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Figure 3 compared to, Figure 5 A cross-sectional view of a light emitting element ED according to one or more embodiments is illustrated, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL. Figure 4 compared to, Figure 6 A cross-sectional view of the light emitting element ED according to one or more embodiments is illustrated, which includes the capping layer CPL disposed on the second electrode EL2 .
[0233] The light-emitting element ED of one or more embodiments may include the fused polycyclic compound of one or more embodiments, which will be described in more detail later, in at least one functional layer included in the light-emitting element ED. The light-emitting element ED of one or more embodiments may include the fused polycyclic compound of one or more embodiments in at least one of the hole transport region HTR, the emission layer EML, and the electron transport region ETR. For example, the emission layer EML in the light-emitting element ED of one or more embodiments may include the fused polycyclic compound of one or more embodiments.
[0234] The first electrode EL1 has conductivity (for example, is a conductor). The first electrode EL1 may be formed of a metal material, a metal alloy, and / or a conductive compound. The first electrode EL1 may be an anode or a cathode. However, the embodiments of the present disclosure are not limited thereto. In one or more embodiments, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode. The first electrode EL1 may include at least one selected from silver (Ag), magnesium (Mg), copper (Cu), aluminum (Al), platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), neodymium (Nd), iridium (Ir), chromium (Cr), lithium (Li), calcium (Ca), lithium fluoride (LiF), molybdenum (Mo), titanium (Ti), tungsten (W), indium (In), tin (Sn), and zinc (Zn), a compound selected from two or more thereof, a mixture selected from two or more thereof, or an oxide thereof.
[0235] If the first electrode EL1 is a transmissive electrode (for example, when the first electrode EL1 is a transmissive electrode), the first electrode EL1 may include a transparent metal oxide (for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO)). If the first electrode EL1 is a transflective electrode or a reflective electrode (for example, when the first electrode EL1 is a transflective electrode or a reflective electrode), the first electrode EL1 may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, and W, a compound thereof, or a mixture thereof (for example, a mixture of Ag and Mg), or a material having a multilayer structure, such as LiF / Ca (a stack structure of LiF and Ca) or LiF / Al (a stack structure of LiF and Al). In one or more embodiments, the first electrode EL1 may have a multilayer structure including a reflective film or a transflective film formed of one or more of the above materials, and a transparent conductive film formed of ITO, IZO, ZnO and / or ITZO, etc. For example, in one or more embodiments, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but the embodiments of the present disclosure are not limited thereto. In one or more embodiments, the first electrode EL1 may include one of the above metal materials, a combination of at least two of the above metal materials and / or any oxide of the above metal materials, etc. The thickness of the first electrode EL1 may be about 700 angstroms. to about For example, in one or more embodiments, the thickness of the first electrode EL1 may be about 100 Å. to about
[0236] The hole transport region HTR may be provided on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, a buffer layer, an emission auxiliary layer, and an electron blocking layer EBL. The thickness of the hole transport region HTR may be, for example, about 100 Å. to about
[0237] The hole transport region HTR may have a single-layer structure of a single layer formed of a single material, a single-layer structure of a single layer formed of a plurality of different materials, or a multi-layer structure including a plurality of layers formed of a plurality of different materials.
[0238] For example, in one or more embodiments, the hole transport region HTR may have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or may have a single-layer structure formed of a hole injection material and / or a hole transport material. In one or more embodiments, the hole transport region HTR may have a single-layer structure formed of a plurality of different materials, or a structure in which hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / buffer layer, hole injection layer HIL / buffer layer, hole transport layer HTL / buffer layer, or hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are stacked in this order (e.g., in the order described) from the first electrode EL1, but the embodiments of the present disclosure are not limited thereto.
[0239] The hole transport region HTR may be formed using one or more appropriate methods such as vacuum deposition, spin coating, casting, Langmuir-Brockett (LB) method, inkjet printing, laser printing, and / or laser induced thermal imaging (LITI) method.
[0240] In one or more embodiments, the hole transport region HTR may include a compound represented by Formula H-1:
[0241] Formula H-1
[0242]
[0243] In formula H-1, L1 and L2 may each independently be a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. a and b may each independently be an integer selected from 0 to 10. In one or more embodiments, if a and b are each an integer of 2 or greater (for example, when a and b are each an integer of 2 or greater), multiple L1 and multiple L2 may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.
[0244] In formula H-1, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. In addition, in formula H-1, Ar3 may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.
[0245] In one or more embodiments, the compound represented by formula H-1 may be a monoamine compound. In one or more embodiments, the compound represented by formula H-1 may be a diamine compound in which at least one selected from Ar1 to Ar3 includes an amino group as a substituent. In one or more embodiments, the compound represented by formula H-1 may be a carbazole compound including a substituted or unsubstituted carbazole group in at least one of Ar1 and Ar2, or a fluorene compound including a substituted or unsubstituted fluorene group in at least one of Ar1 and Ar2.
[0246] The compound represented by formula H-1 may be any one selected from the compounds listed in compound group H. However, the compounds listed in compound group H are merely examples, and the compound represented by formula H-1 is not limited to the compounds listed in compound group H:
[0247] Compound Group H
[0248]
[0249]
[0250] In one or more embodiments, the hole transport region HTR may include one or more selected from the following: a phthalocyanine compound (eg, copper phthalocyanine), N 1 ,N 1’ -([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 ,N 4 -dimethylphenyl-1,4-diamine) (DNTPD), 4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris[N-(2-naphthyl)-N-phenylamino]triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (PAN I / DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyetherketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetrakis(pentafluorophenyl)borate] and / or dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), etc.
[0251] In one or more embodiments, the hole transport region HTR may include one or more selected from the following: carbazole derivatives (e.g., N-phenylcarbazole and / or polyvinylcarbazole), fluorene derivatives and triphenylamine derivatives (e.g., N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD) and / or 1,3-bis(N-carbazolyl)benzene (mCP)), etc.
[0252] In one or more embodiments, the hole transport region HTR may include one or more selected from the group consisting of 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), 9-phenyl-9H-3,9'-bicarbazole (CCP), and 1,3-bis(1,8-dimethyl-9H-carbazole-9-yl)benzene (mDCP).
[0253] The hole transport region HTR may include one or more of the above-mentioned compounds of the hole transport region HTR in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.
[0254] The thickness of the hole transport region HTR may be about to about For example, about to about If the hole transport region HTR includes the hole injection layer HIL (for example, when the hole transport region HTR includes the hole injection layer HIL), the hole injection layer HIL may have, for example, about to about If the hole transport region HTR includes the hole transport layer HTL (for example, when the hole transport region HTR includes the hole transport layer HTL), the hole transport layer HTL may have a thickness of about to about For example, if the hole transport region HTR includes the electron blocking layer EBL (for example, when the hole transport region HTR includes the electron blocking layer EBL), the electron blocking layer EBL may have a thickness of about to about If the thickness of the hole transport region HTR, the thickness of the hole injection layer HIL, the thickness of the hole transport layer HTL, and the thickness of the electron blocking layer EBL satisfy the above ranges (for example, when the thickness of the hole transport region HTR, the thickness of the hole injection layer HIL, the thickness of the hole transport layer HTL, and the thickness of the electron blocking layer EBL satisfy the above ranges), satisfactory hole transport characteristics can be achieved without significantly increasing the driving voltage.
[0255] In one or more embodiments, in addition to the above materials, the hole transport region HTR may further include a charge generation material to increase electrical conductivity (e.g., electrical conductivity). The charge generation material may be uniformly (e.g., substantially uniformly) or non-uniformly dispersed in the hole transport region HTR. The charge generation material may be, for example, a p-dopant. The p-dopant may include at least one of a metal halide, a quinone derivative, a metal oxide, and a cyano group-containing compound, but the embodiments of the present disclosure are not limited thereto. For example, in one or more embodiments, the p-dopant may include a metal halide (e.g., CuI and / or RbI), a quinone derivative (e.g., tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ)), a metal oxide (e.g., tungsten oxide and / or molybdenum oxide) and / or a cyano-containing compound (e.g., dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) and / or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile (NDP9)), etc., but the embodiments of the present disclosure are not limited thereto.
[0256] As described above, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR may further include at least one of a buffer layer and an electron blocking layer EBL. The buffer layer can compensate for the resonance distance according to the wavelength of light emitted from the emission layer EML, thereby increasing luminous efficiency. Materials that can be included in the hole transport region HTR can be used as materials included in the buffer layer. The electron blocking layer EBL is a layer used to prevent or reduce electron injection from the electron transport region ETR into the hole transport region HTR.
[0257] In one or more embodiments, an emission layer EML may be provided on the hole transport region HTR. The emission layer EML may have, for example, approximately to about or about to about The emission layer EML may have a single-layer structure of a single layer formed of a single material, a single-layer structure of a single layer formed of a plurality of different materials, or a multi-layer structure of a plurality of layers formed of a plurality of different materials.
[0258] The light-emitting element ED of one or more embodiments may include a fused polycyclic compound represented by Formula 1 in at least one functional layer arranged between the first electrode EL1 and the second electrode EL2. The emission layer EML in the light-emitting element ED according to one or more embodiments may include the fused polycyclic compound of one or more embodiments. In one or more embodiments, the emission layer EML may include the fused polycyclic compound of one or more embodiments as a dopant. The fused polycyclic compound of one or more embodiments may be a dopant material of the emission layer EML. In the present disclosure, the fused polycyclic compound of one or more embodiments may be referred to as a first compound.
[0259] The fused polycyclic compound of one or more embodiments may include a core comprising a first fused ring structure and a second fused ring structure. The core may be represented by the following formula x. The first fused ring structure includes a structure in which the first to third aromatic rings are fused via a first boron atom, a nitrogen atom, and a first heteroatom X1. The second fused ring structure includes a structure in which the third to fifth aromatic rings are fused via a second boron atom, a second heteroatom X2, and a third heteroatom X3. The first fused ring structure and the second fused ring structure are connected and conjugated via the third aromatic ring.
[0260] Formula x
[0261]
[0262] In the first fused ring structure, the first aromatic ring and the third aromatic ring are connected via the first boron atom and the nitrogen atom. The second aromatic ring and the third aromatic ring are connected via the first boron atom and the first heteroatom X1. The first aromatic ring and the second aromatic ring are connected via the first boron atom. The first boron atom is connected to all of the first to third aromatic rings.
[0263] In the second fused ring structure, the third aromatic ring and the fourth aromatic ring are connected via the second boron atom and the second heteroatom X2. The fourth aromatic ring and the fifth aromatic ring are connected via the second boron atom and the third heteroatom X3. The third aromatic ring and the fifth aromatic ring are connected via the second boron atom. The second boron atom is connected to all of the third to fifth aromatic rings. The third aromatic ring is simultaneously (e.g., synchronously) bonded to each of the first boron atom, the second boron atom, the nitrogen atom, the first heteroatom X1, and the second heteroatom X2. The third aromatic ring can serve as a linking group connecting the first fused ring structure and the second fused ring structure.
[0264] The fused polycyclic compound of one or more embodiments may be represented by Formula 1:
[0265] Formula 1
[0266]
[0267] The fused polycyclic compound represented by Formula 1 according to one or more embodiments includes a core represented by Formula X. In Formula 1, the aromatic ring substituted by T2 is the first aromatic ring, the aromatic ring substituted by T3 is the second aromatic ring, the aromatic ring substituted by T6 is the third aromatic ring, the aromatic ring substituted by T5 is the fourth aromatic ring, and the aromatic ring substituted by T4 is the fifth aromatic ring.
[0268] In Formula 1, T1 may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. In one or more embodiments, T1 may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. In one or more embodiments, T1 may be a substituted or unsubstituted biphenyl group. The fused polycyclic compound of one or more embodiments may be represented by Formula 1-1:
[0269] Formula 1-1
[0270]
[0271] In Formula 1-1, A may be hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms. For example, in one or more embodiments, A may be hydrogen.
[0272] In Formula 1-1, a may be an integer selected from 0 to 9. In Formula 1-1, if a is 0, the fused polycyclic compound of one or more embodiments may not be substituted by A. The embodiment in which a is 9 and all A are hydrogen may be the same as the embodiment in which a is 0. If a is an integer of 2 or greater (for example, when a is an integer of 2 or greater), the plurality of A's may all be the same or at least one selected from the plurality of A's may be different from the others.
[0273] In formula 1-1, q, w, e, r, q21, w31, e41, r51, q2, w2, e2, r2, X1, X2, X3, T 20 、T 30 、T2、T3、T4、T5、T6、T 21 、T 31 、T 41 and T 51 The descriptions of may be the same as those described in Formula 1.
[0274] In Formula 1, X1 may be O or S. For example, in one or more embodiments, X1 may be O. X2 may be O, S, or NT 20 For example, in one or more embodiments, X2 may be NT 20 . X3 can be O, S or NT 30 For example, in one or more embodiments, X3 may be O. In Formula 1, if X1 is O (for example, when X1 is O), X2 is NT 20 , and X3 is O, the fused polycyclic compound of one or more embodiments can be represented by Formula 2-1. In Formula 1, if X1 is O (for example, when X1 is O), X2 is NT 20 , and X3 is NT 30 , the fused polycyclic compound of one or more embodiments can be represented by Formula 2-2.
[0275] Formula 2-1
[0276]
[0277] Formula 2-2
[0278]
[0279] In formula 2-1 and formula 2-2, q, w, e, r, q21, w31, e41, r51, q2, w2, e2, r2, T1, T 20 、T 30 、T2、T3、T4、T5、T6、T 21 、T 31 、T 41 and T 51 The descriptions of are the same as those described in Formula 1.
[0280] In formula 1, T 20 、T 30 T2, T3, T4, T5 and T6 may each independently be hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms. In one or more embodiments, T 20 and T 30 Each of T can be independently substituted or unsubstituted terphenyl. For example, in one or more embodiments, T 20 and T 30Each of T2, T3 and T4 may be independently an unsubstituted m-terphenyl group. In one or more embodiments, T2, T3 and T4 may be each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, in one or more embodiments, T2, T3 and T4 may be each independently an unsubstituted phenyl group or an unsubstituted carbazolyl group. In one or more embodiments, T5 may be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. For example, in one or more embodiments, T5 may be an unsubstituted tert-butyl group. In one or more embodiments, T6 may be hydrogen.
[0281] In formula 1, T 21 、T 31 、T 41 and T 51 Each of the groups may independently be hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms and / or may independently bond with an adjacent group to form a ring. In one or more embodiments, T 21 、T 31 、T 41 and T 51 and T are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. 21 、T 31 、T 41 and T 51 Each independently may be an unsubstituted tert-butyl group or an unsubstituted phenyl group.
[0282] In Formula 1, q21, w31, e41, and r51 may each independently be an integer selected from 0 to 4. In Formula 1, if q21 is 0 (for example, when q21 is 0), the fused polycyclic compound of one or more embodiments may not be T 21 Where q21 is 4 and T 21 The embodiment in which all are hydrogen can be the same as the embodiment in which q21 is 0. If q21 is an integer of 2 or greater (for example, when q21 is an integer of 2 or greater), multiple T 21 Can be the same, or selected from multiple T 21 In Formula 1, if w31 is 0 (for example, when w31 is 0), the fused polycyclic compound of one or more embodiments may not be T 31Where w31 is 4 and T 31 The embodiment in which all are hydrogen may be the same as the embodiment in which w31 is 0. If w31 is an integer of 2 or greater (for example, when w31 is an integer of 2 or greater), multiple T 31 Can be the same, or selected from multiple T 31 In Formula 1, if e41 is 0 (for example, when e41 is 0), the fused polycyclic compound of one or more embodiments may not be T 41 Wherein e41 is 4 and T 41 The embodiment in which all are hydrogen can be the same as the embodiment in which e41 is 0. If e41 is an integer of 2 or greater (for example, when e41 is an integer of 2 or greater), multiple T 41 Can be the same, or selected from multiple T 41 In Formula 1, if r51 is 0 (for example, when r51 is 0), the fused polycyclic compound of one or more embodiments may not be T 51 Where r51 is 4 and T 51 The embodiment in which all are hydrogen can be the same as the embodiment in which r51 is 0. If r51 is an integer of 2 or greater (for example, when r51 is an integer of 2 or greater), multiple T 51 Can be the same, or selected from multiple T 51 At least one of may be different from the others.
[0283] In Formula 1, if q is 0 (for example, when q is 0), q2 is an integer selected from 0 to 4, if q is 1 (for example, when q is 1), q2 is an integer selected from 0 to 2, and if q is 2 or 3 (for example, when q is 2 or 3), q2 is 0. In Formula 1, if q2 is 0 (for example, when q2 is 0), the fused polycyclic compound of one or more embodiments may not be substituted with T2. If q2 is an integer of 2 or greater (for example, when q2 is an integer of 2 or greater), a plurality of T2s may all be the same, or at least one selected from a plurality of T2s may be different from the others.
[0284] In Formula 1, if w is 0 (for example, when w is 0), w2 is an integer selected from 0 to 4, if w is 1 (for example, when w is 1), w2 is an integer selected from 0 to 2, and if w is 2 or 3 (for example, when w is 2 or 3), w2 is 0. In Formula 1, if w2 is 0 (for example, when w2 is 0), the fused polycyclic compound of one or more embodiments may not be substituted with T3. If w2 is an integer of 2 or greater (for example, when w2 is an integer of 2 or greater), a plurality of T3 may be the same, or at least one of the plurality of T3 may be different from the others.
[0285] In Formula 1, if e is 0 (for example, when e is 0), e2 is an integer selected from 0 to 4, if e is 1 (for example, when e is 1), e2 is an integer selected from 0 to 2, and if e is 2 or 3 (for example, when e is 2 or 3), e2 is 0. In Formula 1, if e2 is 0 (for example, when e2 is 0), the fused polycyclic compound of one or more embodiments may not be substituted with T4. If e2 is an integer of 2 or greater (for example, when e2 is an integer of 2 or greater), a plurality of T4 may be the same, or at least one of the plurality of T4 may be different from the others.
[0286] In Formula 1, if r is 0 (for example, when r is 0), r2 is an integer selected from 0 to 3, and if r is 1 (for example, when r is 1), r2 is 0 or 1. In Formula 1, if r2 is 0 (for example, when r2 is 0), the fused polycyclic compound of one or more embodiments may not be substituted with T5. If r2 is an integer of 2 or greater (for example, when r2 is an integer of 2 or greater), a plurality of T5 may be the same, or at least one of the plurality of T5 may be different from the others.
[0287] In Formula 1, q, w, and e may each independently be an integer selected from 0 to 3. r may be an integer selected from 0 to 2. The sum of q, w, e, and r is 1 or greater. For example, at least one of q, w, e, and r is not 0. For example, in one or more embodiments, q may be 1 and each of w, e, and r may be 0.
[0288] In Formula 1, if q is 1 (for example, when q is 1), the fused polycyclic compound of one or more embodiments may be represented by any one selected from Formula 3-1 to Formula 3-3:
[0289] Formula 3-1
[0290]
[0291] Formula 3-2
[0292]
[0293] Formula 3-3
[0294]
[0295] In Formula 1, if q is 2 (for example, when q is 2), the fused polycyclic compound of one or more embodiments may be represented by any one selected from Formula 3-4 to Formula 3-6:
[0296] Formula 3-4
[0297]
[0298] Formula 3-5
[0299]
[0300] Formula 3-6
[0301]
[0302] In Formula 1, if q is 3 (for example, when q is 3), the fused polycyclic compound of one or more embodiments may be represented by Formula 3-7:
[0303] Formula 3-7
[0304]
[0305] In Equations 3-1 to 3-7, T 201 、T 202 、T 203 、T 204 、T 205 、T 206 and T 207 Each of the groups may independently be hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms and / or may be bonded to an adjacent group to form a ring. In one or more embodiments, T 201 、T 202 、T 203 、T 204 、T 205 、T 206 and T 207 Each of the substituted or unsubstituted aryl groups has 6 to 30 ring carbon atoms. 201 、T 202 、T 203 、T 204 、T 205 、T 206 and T 207 Each independently may be an unsubstituted phenyl group.
[0306] In Formula 3-1 to Formula 3-7, q201, q202, and q203 may each independently be an integer selected from 0 to 6, and q204, q205, q206, and q207 may each independently be an integer selected from 0 to 8.
[0307] In Formula 3-1, if q201 is 0 (for example, when q201 is 0), the fused polycyclic compound of one or more embodiments may not be T 201Where q201 is 6 and T 201 The embodiment in which all are hydrogen can be the same as the embodiment in which q201 is 0. If q201 is an integer of 2 or greater (for example, when q201 is an integer of 2 or greater), multiple T 201 Can be the same, or selected from multiple T 201 At least one of may be different from the others.
[0308] In Formula 3-2, if q202 is 0 (for example, when q202 is 0), the fused polycyclic compound of one or more embodiments may not be T 202 Where q202 is 6 and T 202 The embodiment in which all are hydrogen can be the same as the embodiment in which q202 is 0. If q202 is an integer of 2 or greater (for example, when q202 is an integer of 2 or greater), multiple T 202 Can be the same, or selected from multiple T 202 At least one of may be different from the others.
[0309] In Formula 3-3, if q203 is 0 (for example, when q203 is 0), the fused polycyclic compound of one or more embodiments may not be T 203 Wherein q203 is 6 and T 203 The embodiment in which all are hydrogen can be the same as the embodiment in which q203 is 0. If q203 is an integer of 2 or greater (for example, when q203 is an integer of 2 or greater), multiple T 203 Can be the same, or selected from multiple T 203 At least one of may be different from the others.
[0310] In Formula 3-4, if q204 is 0 (for example, when q204 is 0), the fused polycyclic compound of one or more embodiments may not be T 204 Where q204 is 8 and T 204 The embodiment in which all are hydrogen can be the same as the embodiment in which q204 is 0. If q204 is an integer of 2 or greater (for example, when q204 is an integer of 2 or greater), multiple T 204 Can be the same, or selected from multiple T 204 At least one of may be different from the others.
[0311] In Formula 3-5, if q205 is 0 (for example, when q205 is 0), the fused polycyclic compound of one or more embodiments may not be T 205 Wherein q205 is 8 and T 205The embodiment in which all are hydrogen can be the same as the embodiment in which q205 is 0. If q205 is an integer of 2 or greater (for example, when q205 is an integer of 2 or greater), multiple T 205 Can be the same, or selected from multiple T 205 At least one of may be different from the others.
[0312] In Formula 3-6, if q206 is 0 (for example, when q206 is 0), the fused polycyclic compound of one or more embodiments may not be T 206 Where q206 is 8 and T 206 The embodiment in which all are hydrogen can be the same as the embodiment in which q206 is 0. If q206 is an integer of 2 or greater (for example, when q206 is an integer of 2 or greater), multiple T 206 Can be the same, or selected from multiple T 206 At least one of may be different from the others.
[0313] In Formula 3-7, if q207 is 0 (eg, when q207 is 0), the fused polycyclic compound of one or more embodiments may not be T 207 Where q207 is 8 and T 207 The embodiment in which all are hydrogen can be the same as the embodiment in which q207 is 0. If q207 is an integer of 2 or greater (for example, when q207 is an integer of 2 or greater), multiple T 207 Can be the same, or selected from multiple T 207 At least one of may be different from the others.
[0314] In formulas 3-1 to 3-7, w, e, r, w31, e41, r51, w2, e2, r2, X1, X2, X3, T1, T 20 、T 30 、T3、T4、T5、T6、T 31 、T 41 and T 51 The descriptions of may be the same as those described in Formula 1.
[0315] In Formula 1, if w is 1 (for example, when w is 1), the fused polycyclic compound of one or more embodiments may be represented by any one selected from Formula 4-1 to Formula 4-3:
[0316] Formula 4-1
[0317]
[0318] Formula 4-2
[0319]
[0320] Formula 4-3
[0321]
[0322] In Formula 1, if w is 2 (for example, when w is 2), the fused polycyclic compound of one or more embodiments may be represented by any one selected from Formula 4-4 to Formula 4-6:
[0323] Formula 4-4
[0324]
[0325] Formula 4-5
[0326]
[0327] Formula 4-6
[0328]
[0329] In Formula 1, if w is 3 (for example, when w is 3), the fused polycyclic compound of one or more embodiments may be represented by Formulas 4-7:
[0330] Formula 4-7
[0331]
[0332] In equations 4-1 to 4-7, T 301 、T 302 、T 303 、T 304 、T 305 、T 306 and T 307 Each of the groups may independently be hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms and / or may be bonded to an adjacent group to form a ring. In one or more embodiments, T 301 、T 302 、T 303 、T 304 、T 305 、T 306 and T 307 and T are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. 301 、T 302 、T 303 、T 304 、T305 、T 306 and T 307 Each independently may be an unsubstituted tert-butyl group or an unsubstituted phenyl group.
[0333] In Formula 4-1 to Formula 4-7, w301, w302, and w303 may each independently be an integer selected from 0 to 6, and w304, w305, w306, and w307 may each independently be an integer selected from 0 to 8.
[0334] In Formula 4-1, if w301 is 0 (for example, when w301 is 0), the fused polycyclic compound of one or more embodiments may not be T 301 Where w301 is 6 and T 301 The embodiment in which all are hydrogen can be the same as the embodiment in which w301 is 0. If w301 is an integer of 2 or greater (for example, when w301 is an integer of 2 or greater), multiple T 301 Can be the same, or selected from multiple T 301 At least one of may be different from the others.
[0335] In Formula 4-2, if w302 is 0 (for example, when w302 is 0), the fused polycyclic compound of one or more embodiments may not be T 302 Where w302 is 6 and T 302 The embodiment in which all are hydrogen can be the same as the embodiment in which w302 is 0. If w302 is an integer of 2 or greater (for example, when w302 is an integer of 2 or greater), multiple T 302 Can be the same, or selected from multiple T 302 At least one of may be different from the others.
[0336] In Formula 4-3, if w303 is 0 (for example, when w303 is 0), the fused polycyclic compound of one or more embodiments may not be T 303 Where w303 is 6 and T 303 The embodiment in which all are hydrogen can be the same as the embodiment in which w303 is 0. If w303 is an integer of 2 or greater (for example, when w303 is an integer of 2 or greater), multiple T 303 Can be the same, or selected from multiple T 303 At least one of may be different from the others.
[0337] In Formula 4-4, if w304 is 0 (for example, when w304 is 0), the fused polycyclic compound of one or more embodiments may not be T 304 Where w304 is 8 and T 304The embodiment in which all are hydrogen can be the same as the embodiment in which w304 is 0. If w304 is an integer of 2 or greater (for example, when w304 is an integer of 2 or greater), multiple T 304 Can be the same, or selected from multiple T 304 At least one of may be different from the others.
[0338] In Formula 4-5, if w305 is 0 (for example, when w305 is 0), the fused polycyclic compound of one or more embodiments may not be T 305 Where w305 is 8 and T 305 The embodiment in which all are hydrogen can be the same as the embodiment in which w305 is 0. If w305 is an integer of 2 or greater (for example, when w305 is an integer of 2 or greater), multiple T 305 Can be the same, or selected from multiple T 305 At least one of may be different from the others.
[0339] In Formula 4-6, if w306 is 0 (for example, when w306 is 0), the fused polycyclic compound of one or more embodiments may not be T 306 Where w306 is 8 and T 306 The embodiment in which all are hydrogen can be the same as the embodiment in which w306 is 0. If w306 is an integer of 2 or greater (for example, when w306 is an integer of 2 or greater), multiple T 306 Can be the same, or selected from multiple T 306 At least one of may be different from the others.
[0340] In Formula 4-7, if w307 is 0 (for example, when w307 is 0), the fused polycyclic compound of one or more embodiments may not be T 307 substituted. Embodiment wherein w307 is 8 and T 307 are all hydrogen, which is the same as the embodiment in which w307 is 0. If w307 is an integer of 2 or greater (for example, when w307 is an integer of 2 or greater), multiple T 307 Can be the same, or selected from multiple T 307 At least one of may be different from the others.
[0341] In formulas 4-1 to 4-7, q, e, r, q21, e41, r51, q2, e2, r2, X1, X2, X3, T1, T 20 、T 30 、T2、T4、T5、T6、T 21 、T 41 and T 51 The descriptions of may be the same as those described in Formula 1.
[0342] In Formula 1, if e is 1 (for example, when e is 1), the fused polycyclic compound of one or more embodiments may be represented by any one selected from Formula 5-1 to Formula 5-3:
[0343] Formula 5-1
[0344]
[0345] Formula 5-2
[0346]
[0347] Formula 5-3
[0348]
[0349] In Formula 1, if e is 2 (for example, when e is 2), the fused polycyclic compound of one or more embodiments may be represented by any one selected from Formula 5-4 to Formula 5-6:
[0350] Formula 5-4
[0351]
[0352] Formula 5-5
[0353]
[0354] Formula 5-6
[0355]
[0356] In Formula 1, if e is 3 (for example, when e is 3), the fused polycyclic compound of one or more embodiments may be represented by Formulas 5-7:
[0357] Formula 5-7
[0358]
[0359] In Equations 5-1 to 5-7, T 401 、T 402 、T 403 、T 404 、T 405 、T 406 and T 407Each of the groups may independently be hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms and / or may be bonded to an adjacent group to form a ring. In one or more embodiments, T 401 、T 402 、T 403 、T 404 、T 405 、T 406 and T 407 Each independently may be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. For example, in one or more embodiments, T 401 、T 402 、T 403 、T 404 、T 405 、T 406 and T 407 Each independently may be an unsubstituted tert-butyl group.
[0360] In Formula 5-1 to Formula 5-7, e401, e402, and e403 may each independently be an integer selected from 0 to 6, and e404, e405, e406, and e407 may each independently be an integer selected from 0 to 8.
[0361] In Formula 5-1, if e401 is 0 (for example, when e401 is 0), the fused polycyclic compound of one or more embodiments may not be T 401 Wherein e401 is 6 and T 401 The embodiment in which all are hydrogen can be the same as the embodiment in which e401 is 0. If e401 is an integer of 2 or greater (for example, when e401 is an integer of 2 or greater), multiple T 401 Can be the same, or selected from multiple T 401 At least one of may be different from the others.
[0362] In Formula 5-2, if e402 is 0 (for example, when e402 is 0), the fused polycyclic compound of one or more embodiments may not be T 402 Where e402 is 6 and T 402 The embodiment in which all are hydrogen can be the same as the embodiment in which e402 is 0. If e402 is an integer of 2 or greater (for example, when e402 is an integer of 2 or greater), multiple T 402 Can be the same, or selected from multiple T 402 At least one of may be different from the others.
[0363] In Formula 5-3, if e403 is 0 (for example, when e403 is 0), the fused polycyclic compound of one or more embodiments may not be T 403 Wherein e403 is 6 and T 403 The embodiment in which all are hydrogen can be the same as the embodiment in which e403 is 0. If e403 is an integer of 2 or greater (for example, when e403 is an integer of 2 or greater), multiple T 403 Can be the same, or selected from multiple T 403 At least one of may be different from the others.
[0364] In Formula 5-4, if e404 is 0 (for example, when e404 is 0), the fused polycyclic compound of one or more embodiments may not be T 404 Wherein e404 is 8 and T 404 The embodiment in which all are hydrogen can be the same as the embodiment in which e404 is 0. If e404 is an integer of 2 or greater (for example, when e404 is an integer of 2 or greater), multiple T 404 Can be the same, or selected from multiple T 404 At least one of may be different from the others.
[0365] In Formula 5-5, if e405 is 0 (for example, when e405 is 0), the fused polycyclic compound of one or more embodiments may not be T 405 Wherein e405 is 8 and T 405 The embodiment in which all are hydrogen can be the same as the embodiment in which e405 is 0. If e405 is an integer of 2 or greater (for example, when e405 is an integer of 2 or greater), multiple T 405 Can be the same, or selected from multiple T 405 At least one of may be different from the others.
[0366] In Formula 5-6, if e406 is 0 (for example, when e406 is 0), the fused polycyclic compound of one or more embodiments may not be T 406 Where e406 is 8 and T 406 The embodiment in which all are hydrogen can be the same as the embodiment in which e406 is 0. If e406 is an integer of 2 or greater (for example, when e406 is an integer of 2 or greater), multiple T 406 Can be the same, or selected from multiple T 406 At least one of may be different from the others.
[0367] In Formula 5-7, if e407 is 0 (eg, when e407 is 0), the fused polycyclic compound of one or more embodiments may not be T 407 Where e407 is 8 and T407 The embodiment in which all are hydrogen can be the same as the embodiment in which e407 is 0. If e407 is an integer of 2 or greater (for example, when e407 is an integer of 2 or greater), multiple T 407 Can be the same, or selected from multiple T 407 At least one of may be different from the others.
[0368] In the above formulas 5-1 to 5-7, q, w, r, q21, w31, r51, q2, w2, r2, X1, X2, X3, T1, T 20 、T 30 、T2、T3、T5、T6、T 21 、T 31 and T 51 The descriptions of may be the same as those described in Formula 1.
[0369] In Formula 1, if r is 1 (for example, when r is 1), the fused polycyclic compound of one or more embodiments may be represented by Formula 6-1 or Formula 6-2:
[0370] Formula 6-1
[0371]
[0372] Formula 6-2
[0373]
[0374] In Formula 1, if r is 0 (for example, when r is 0), the fused polycyclic compound of one or more embodiments may be represented by Formula 6-3:
[0375] Formula 6-3
[0376]
[0377] In Equations 6-1 to 6-3, T 501 To T 503 and R are each independently hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms. For example, in one or more embodiments, T 501 and T 502 may each independently be hydrogen, and T 503 It may be an unsubstituted tert-butyl group.
[0378] In Formula 6-1 to Formula 6-3, r501 and r502 may each independently be an integer selected from 0 to 5, and r503 may be an integer selected from 0 to 3.
[0379] In Formula 6-1, if r501 is 0 (for example, when r501 is 0), the fused polycyclic compound of one or more embodiments may not be T 501 Where r501 is 5 and T 501 The embodiment in which all are hydrogen can be the same as the embodiment in which r501 is 0. If r501 is an integer of 2 or greater (for example, when r501 is an integer of 2 or greater), multiple T 501 Can be the same, or selected from multiple T 501 At least one of may be different from the others.
[0380] In Formula 6-2, if r502 is 0 (for example, when r502 is 0), the fused polycyclic compound of one or more embodiments may not be T 502 Where r502 is 5 and T 502 The embodiment in which all are hydrogen can be the same as the embodiment in which r502 is 0. If r502 is an integer of 2 or greater (for example, when r502 is an integer of 2 or greater), multiple T 502 Can be the same, or selected from multiple T 502 At least one of may be different from the others.
[0381] In Formula 6-3, if r503 is 0 (for example, when r503 is 0), the fused polycyclic compound of one or more embodiments may not be T 503 Where r503 is 3 and T 503 The embodiment in which all are hydrogen can be the same as the embodiment in which r503 is 0. If r503 is an integer of 2 or greater (for example, when r503 is an integer of 2 or greater), multiple T 503 Can be the same, or selected from multiple T 503 At least one of may be different from the others.
[0382] In equations 6-1 to 6-3, q, w, e, q21, w31, e41, q2, w2, e2, X1, X2, X3, T1, T 20 、T 30 、T2、T3、T4、T6、T 21 、T 31 and T 41 The descriptions of may be the same as those described in Formula 1.
[0383] In one or more embodiments, the fused polycyclic compound of one or more embodiments represented by any one selected from Formula 1, Formula 1-1, Formula 2-1, Formula 3-1 to Formula 3-7, Formula 4-1 to Formula 4-7, Formula 5-1 to Formula 5-7, and Formula 6-1 to Formula 6-3 may include at least one deuterium as a substituent.
[0384] The fused polycyclic compound of one or more embodiments may be any one selected from the compounds listed in compound group 1. At least one functional layer included in the light-emitting element ED of one or more embodiments may include at least one fused polycyclic compound selected from the compounds listed in compound group 1. The light-emitting element ED of one or more embodiments may include at least one fused polycyclic compound selected from the compounds listed in compound group 1 in the emission layer EML.
[0385] Compound Group 1
[0386]
[0387]
[0388]
[0389]
[0390]
[0391]
[0392]
[0393]
[0394]
[0395]
[0396]
[0397]
[0398]
[0399]
[0400]
[0401]
[0402]
[0403]
[0404]
[0405]
[0406]
[0407] In the exemplary compounds presented in Compound Group 1, "D" refers to deuterium.
[0408] The fused polycyclic compound generally included in the emission layer of the organic electroluminescent element has high planarity and therefore has strong intermolecular interactions, which deteriorates the stability of the fused polycyclic compound, and if the fused polycyclic compound has a structure in which two oxygen atoms are simultaneously (e.g., synchronously) bonded to a boron atom (e.g., when the fused polycyclic compound has a structure in which two oxygen atoms are simultaneously (e.g., synchronously) bonded to a boron atom), there are limitations and problems in that the fused polycyclic compound is easily decomposed in the post-synthesis purification process.
[0409] The fused polycyclic compound of one or more embodiments includes a core comprising the above-mentioned first fused ring structure and the second fused ring structure, thereby achieving high luminous efficiency and long element service life. For example, by including a first fused ring structure comprising a boron atom, a nitrogen atom and a heteroatom, rather than a structure in which the boron atom and two oxygen atoms of the fused polycyclic compound contained in the emission layer of a common organic electroluminescent element are fused simultaneously (for example, synchronously), the spatial characteristics of the fused polycyclic compound are increased, thereby reducing the intermolecular interaction between the fused polycyclic compound molecules, and having the effect of improving the stability of the fused polycyclic compound. In addition, in the fused polycyclic compound of one or more embodiments, due to steric hindrance, the biphenyl and / or terphenyl substituted at the nitrogen atom are located on different planes from the first fused ring structure and the second fused ring structure, and therefore have the effect of further enhancing the spatial characteristics of the fused polycyclic compound. In addition, the first fused ring structure or the second fused ring structure may include at least one of a naphthyl, a phenanthrenyl and a pyrenyl to reduce the lowest triplet excitation energy level (T1) of the fused polycyclic compound, and therefore the fused polycyclic compound can exhibit high thermal stability and chemical stability.
[0410] The fused polycyclic compound represented by Formula 1 of one or more embodiments may be a light-emitting material having a central wavelength of light emission in the range of about 430 nm to about 490 nm. For example, the fused polycyclic compound represented by Formula 1 of one or more embodiments may be a blue thermally activated delayed fluorescence (TADF) dopant. However, the embodiments of the present disclosure are not limited thereto, and if the fused polycyclic compound of one or more embodiments is used as a light-emitting material (for example, when the fused polycyclic compound of one or more embodiments is used as a light-emitting material), the fused polycyclic compound as the first compound / dopant may be used as a dopant material emitting light in one or more appropriate wavelength regions, such as a red emitting dopant or a green emitting dopant.
[0411] The emission layer EML in the light emitting element ED of one or more embodiments may emit delayed fluorescence. For example, the emission layer EML may emit thermally activated delayed fluorescence (TADF).
[0412] In one or more embodiments, the emission layer EML of the light-emitting element ED may emit blue light. For example, the emission layer EML of the light-emitting element ED (e.g., the organic electroluminescent element ED) of one or more embodiments may emit blue light within a wavelength range of about 490 nm or less. However, the embodiments of the present disclosure are not limited thereto, and the emission layer EML may emit green light or red light.
[0413] In one or more embodiments, the fused polycyclic compound of one or more embodiments may be included in the emission layer EML. The fused polycyclic compound of one or more embodiments may be included in the emission layer EML as a dopant material. The fused polycyclic compound of one or more embodiments may be a thermally activated delayed fluorescent material. The fused polycyclic compound of one or more embodiments may be used as a thermally activated delayed fluorescent dopant. For example, in the light-emitting element ED of one or more embodiments, the emission layer EML may include at least one of the fused polycyclic compounds listed in the above-mentioned compound group 1 as a thermally activated delayed fluorescent dopant. However, the application of the fused polycyclic compound of one or more embodiments is not limited thereto.
[0414] In one or more embodiments, the emission layer EML may include the fused polycyclic compound represented by Formula 1 as a first compound, and may further include at least one of a second compound represented by Formula HT-1, a third compound represented by Formula ET-1, and a fourth compound represented by Formula D-1.
[0415] In one or more embodiments, the emission layer EML may include the fused polycyclic compound represented by Formula 1 as a first compound, and may further include at least one of a second compound represented by Formula HT-1 and a third compound represented by Formula ET-1.
[0416] In one or more embodiments, the emission layer EML may further include a second compound represented by Formula HT-1. In one or more embodiments, the second compound may serve as a hole transport host material of the emission layer EML.
[0417] Formula HT-1
[0418]
[0419] In formula HT-1, M1 to M8 can each independently be N or CR 51 For example, in one or more embodiments, all of M1 to M8 may be CR 51In one or more embodiments, any one selected from M1 to M8 may be N, and the rest may be CR 51 .
[0420] In Formula HT-1, L1 may be a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. For example, in one or more embodiments, L1 may be a directly linked, substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, and / or a substituted or unsubstituted divalent carbazolyl group, etc., but the embodiments of the present disclosure are not limited thereto.
[0421] In formula HT-1, Y a Can be direct connection, CR 52 R 53 or SiR 54 R 55 For example, it may refer to two six-membered rings (eg, two benzene rings) connected to the nitrogen atom in formula HT-1 being directly connected, In formula HT-1, if Y a For direct connection (for example, when Y a is directly linked), the second compound represented by Formula HT-1 may include a carbazole moiety.
[0422] In formula HT-1, Ar a It may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in one or more embodiments, Ar a The group may be a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and / or a substituted or unsubstituted biphenyl group, but the embodiments of the present disclosure are not limited thereto.
[0423] In formula HT-1, R 51 to R 55 Each of the following may independently be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted thiol, substituted or unsubstituted oxy, substituted or unsubstituted amine, substituted or unsubstituted boron, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 60 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 60 ring carbon atoms. In one or more embodiments, the group selected from R 51 to R 55One or more of can be independently bonded to adjacent groups to form a ring. For example, in one or more embodiments, R 51 to R 55 Can be each independently hydrogen or deuterium. In one or more embodiments, R 51 to R 55 Each independently may be an unsubstituted methyl group or an unsubstituted phenyl group.
[0424] In one or more embodiments, the second compound represented by Formula HT-1 may be any one selected from the compounds listed in Compound Group 2. The emission layer EML may include at least one selected from the compounds listed in Compound Group 2 as a hole transport host material.
[0425] Compound Group 2
[0426]
[0427]
[0428]
[0429] In the exemplary compounds presented in Compound Group 2, "D" may refer to deuterium, and "Ph" may refer to substituted or unsubstituted phenyl. For example, in the exemplary compounds presented in Compound Group 2, "Ph" may refer to unsubstituted phenyl.
[0430] In one or more embodiments, the emission layer EML may further include a third compound represented by Formula ET-1. For example, the third compound may serve as an electron transport host material for the emission layer EML.
[0431] Formula ET-1
[0432]
[0433] In formula ET-1, Z a to Z c At least one of them can be N, and the rest can be CR 56 For example, in one or more embodiments, the group consisting of Z a to Z c Any one of them may be N, and the rest may each independently be CR 56 In these embodiments, the third compound represented by Formula ET-1 may include a pyridine moiety. In one or more embodiments, the compound selected from Z a to Z c Two of them can be N, and the rest can be CR 56In these embodiments, the third compound represented by Formula ET-1 may include a pyrimidine moiety. In one or more embodiments, Z a to Z c Both may be N. In these embodiments, the third compound represented by Formula ET-1 may include a triazine moiety.
[0434] In formula ET-1, R 56 It may be hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms.
[0435] In Formula ET-1, b1 to b3 may each independently be an integer selected from 0 to 10.
[0436] In formula ET-1, Ar b to Ar d and R are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. b to Ar d Each independently may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted carbazolyl group.
[0437] In Formula ET-1, L2 to L4 may each independently be a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. In one or more embodiments, if b1 to b3 are an integer of 2 or greater (for example, when b1 to b3 are an integer of 2 or greater), multiple L2 to multiple L4 may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.
[0438] In one or more embodiments, the third compound may be any one of the compounds selected from compound group 3. The light emitting element ED according to one or more embodiments may include any one of the compounds selected from compound group 3.
[0439] Compound Group 3
[0440]
[0441]
[0442]
[0443]
[0444]
[0445]
[0446]
[0447]
[0448] In the exemplary compounds presented in Compound Group 3, "D" refers to deuterium, and "Ph" refers to unsubstituted phenyl.
[0449] In one or more embodiments, the emission layer (EML) may include a second compound and a third compound, and the second compound and the third compound may form an exciplex. In the emission layer (EML), an exciplex may be formed by a hole transport host and an electron transport host. In this regard, the lowest triplet excitation energy level of the exciplex formed by the hole transport host and the electron transport host may correspond to the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the electron transport host and the highest occupied molecular orbital (HOMO) energy level of the hole transport host.
[0450] For example, in one or more embodiments, the absolute value of the lowest triplet excitation energy level (T1) of the exciplex formed by the hole transport host and the electron transport host may be about 2.4 eV to about 3.0 eV. In addition, the lowest triplet excitation energy level of the exciplex may be a value less than the energy gap of each host material. The exciplex may have a lowest triplet excitation energy level of about 3.0 eV or less as the energy gap between the hole transport host and the electron transport host.
[0451] In one or more embodiments, the emission layer (EML) may further include a fourth compound in addition to the first to third compounds described above. The fourth compound may serve as a sensitizer for the emission layer (EML). Energy may be transferred from the fourth compound to the first compound, thereby emitting light.
[0452] For example, in one or more embodiments, the emission layer EML may include an organic metal complex as the fourth compound, the organic metal complex containing platinum (Pt) as a central metal atom and a ligand connected to the central metal atom. The emission layer EML in the light-emitting element ED of one or more embodiments may include a compound represented by Formula D-1 as the fourth compound:
[0453] Formula D-1
[0454]
[0455] In formula D-1, Q1 to Q4 may each independently be C or N.
[0456] In formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring group having 5 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 ring carbon atoms.
[0457] In formula D-1, X 11 To X 14 Can be directly connected or *-O-* independently. For example, in one or more embodiments, selected from X 11 To X 14 One of them can be *-O-*, and the other X 11 To X 14 Each of can be a direct connection.
[0458] In formula D-1, L 11 To L 13 Can be directly connected, *-O-*, *-S-*, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. 11 To L 13 In the figure, “-*” indicates the portion connected to C1 to C4.
[0459] In Formula D-1, b11 to b13 may each independently be 0 or 1. If b11 is 0 (e.g., when b11 is 0), C1 and C2 may not be connected to each other. If b12 is 0 (e.g., when b12 is 0), C2 and C3 may not be connected to each other. If b13 is 0 (e.g., when b13 is 0), C3 and C4 may not be connected to each other.
[0460] In formula D-1, R 61 to R 66 Each of the following may independently be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted thiol, substituted or unsubstituted oxy, substituted or unsubstituted amine, substituted or unsubstituted boron, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 60 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 60 ring carbon atoms. In one or more embodiments, the group selected from R 61 to R 66One or more of can independently bond with adjacent groups to form a ring. In one or more embodiments, R 61 to R 66 Each independently may be a substituted or unsubstituted methyl group or a substituted or unsubstituted tert-butyl group.
[0461] In Formula D-1, d1 to d4 may each independently be an integer selected from 0 to 4. In Formula D-1, if each of d1 to d4 is 0 (for example, when each of d1 to d4 is 0), the fourth compound may not be R 61 to R 64 Each of d1 to d4 is 4 and R 61 to R 64 The embodiment in which each of d1 to d4 is hydrogen may be the same as the embodiment in which each of d1 to d4 is 0. When each of d1 to d4 is an integer of 2 or greater, the plurality of R 61 To multiple R 64 Can be the same as each other, or selected from multiple R 61 To multiple R 64 At least one of may be different from the others.
[0462] In formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring group or a substituted or unsubstituted heterocyclic group represented by any one of C-1 to C-5:
[0463]
[0464] In C-1 to C-5, P1 can be C-* or CR 74 , P2 can be N-* or NR 81 , P3 can be N-* or NR 82 , P4 can be C-* or CR 88 , and P6 can be C-* or CR 90 . R 71 to R 90 Each may independently be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms and / or may be bonded with an adjacent group to form a ring.
[0465] In addition, in C-1 to C-5, corresponds to a portion connected to Pt as a central metal atom, and "-*" corresponds to a portion connected to adjacent cyclic groups C1 to C4 or an adjacent linking group L 11 To L 13 part.
[0466] The emission layer (EML) of one or more embodiments may include a fused polycyclic compound represented by Formula 1 as a first compound and at least one selected from second to fourth compounds. For example, in one or more embodiments, the emission layer (EML) may include a first compound, a second compound, and a third compound. In the emission layer (EML), the second compound and the third compound may form an exciplex, and energy may be transferred from the exciplex to the first compound, thereby emitting light.
[0467] In one or more embodiments, the emission layer EML may include a first compound, a second compound, a third compound, and a fourth compound. In the emission layer EML, the second compound and the third compound may form an exciplex, and energy may be transferred from the exciplex to the fourth compound and the first compound, thereby emitting light. In one or more embodiments, the fourth compound may be a sensitizer. The fourth compound included in the emission layer EML in the light-emitting element ED of one or more embodiments may serve as a sensitizer to transfer energy from the host to the first compound, which is a light-emitting dopant. For example, in one or more embodiments, the fourth compound, which serves as an auxiliary dopant, accelerates the energy delivery to the first compound, which is a light-emitting dopant, thereby increasing the emission ratio of the first compound. Therefore, the emission layer EML of one or more embodiments may improve luminous efficiency. In addition, if the energy delivered to the first compound increases (for example, when the energy delivered to the first compound increases), the excitons formed in the emission layer EML do not accumulate inside the emission layer EML but emit light quickly, thereby reducing the degradation of the light-emitting element ED. Therefore, the element service life of the light-emitting element ED of one or more embodiments may be increased.
[0468] The light-emitting element ED of one or more embodiments may include all of the first compound, the second compound, the third compound, and the fourth compound, and the emission layer EML may include a combination of two host materials and two dopant materials. In the light-emitting element ED of one or more embodiments, the emission layer EML may simultaneously (e.g., synchronously) include the second compound and the third compound as two different hosts, the first compound emitting delayed fluorescence, and the fourth compound including the organometallic complex, thereby exhibiting excellent or appropriate luminous efficiency characteristics.
[0469] In one or more embodiments, the fourth compound represented by Formula D-1 may be any one selected from the compounds listed in Compound Group 4. The emission layer EML may include at least one selected from the compounds listed in Compound Group 4 as a sensitizer material.
[0470] Compound Group 4
[0471]
[0472]
[0473]
[0474]
[0475] In the exemplary compounds presented in Compound Group 4, "D" refers to deuterium.
[0476] In one or more embodiments, the light-emitting element ED may include a plurality of emission layers EML. A plurality of emission layers EML may be provided by stacking in sequence. For example, in one or more embodiments, the light-emitting element ED including a plurality of emission layers EML may emit white light (e.g., combined white light). The light-emitting element ED including a plurality of emission layers EML may be a light-emitting element having a series structure. When the light-emitting element ED includes a plurality of emission layers EML, at least one emission layer EML may include a fused polycyclic compound represented by Formula 1 as the first compound. In addition, if the light-emitting element ED includes a plurality of emission layers EML (e.g., when the light-emitting element ED includes a plurality of emission layers EML), at least one emission layer EML may include all of the first compound, the second compound, the third compound, and the fourth compound as described above.
[0477] When the emission layer EML in the light-emitting element ED of one or more embodiments includes all of the first compound, the second compound, the third compound, and the fourth compound, the content (e.g., amount) of the first compound relative to the total weight of the first compound, the second compound, the third compound, and the fourth compound may be from about 0.1 wt % to about 5 wt %. However, the embodiments of the present disclosure are not limited thereto. When the content (e.g., amount) of the first compound satisfies the above ratio, energy transfer from the second compound and the third compound to the first compound can be increased, thereby increasing luminous efficiency and element service life.
[0478] The content (e.g., amount) of the second compound and the third compound in the emission layer (EML) may be the remaining content (e.g., amount) other than the weight of the first compound and the fourth compound. For example, in one or more embodiments, the content (e.g., amount) of the second compound and the third compound in the emission layer (EML) may be from about 65 wt % to about 95 wt % relative to the total weight of the first compound, the second compound, the third compound, and the fourth compound.
[0479] A weight ratio of the second compound to the third compound in the total weight of the second compound and the third compound may be about 3:7 to about 7:3.
[0480] When the content (e.g., amount) of the second compound and the third compound satisfies the above ratio, the charge balance characteristics in the emission layer EML are improved, and thus the luminous efficiency and the life of the element can be increased. When the content (e.g., amount) of the second compound and the third compound deviates from the above ratio range, the charge balance in the emission layer EML is destroyed, and thus the luminous efficiency can be reduced and the light-emitting element can be easily degraded.
[0481] In one or more embodiments, when the emission layer EML further includes a fourth compound, the content (e.g., amount) of the fourth compound in the emission layer EML may be from about 10 wt % to about 30 wt % relative to the total weight of the first compound, the second compound, the third compound, and the fourth compound. However, the embodiments of the present disclosure are not limited thereto. When the content (e.g., amount) of the fourth compound satisfies the above content (e.g., amount), energy transfer from the host to the first compound as a light-emitting dopant can be increased, thereby improving the luminescence ratio and, therefore, improving the luminous efficiency of the emission layer EML. When the fourth compound included in the emission layer EML satisfies the above content (e.g., amount) ratio range, excellent or appropriate luminous efficiency and long element service life of the light-emitting element ED can be achieved.
[0482] In the light-emitting element ED of one or more embodiments, the emission layer EML may further include at least one of an anthracene derivative, a pyrene derivative, a fluoranthene derivative, a 1,2-triphenylene derivative, a dihydrobenzanthracene derivative, and a triphenylene derivative. For example, in one or more embodiments, the emission layer EML may include an anthracene derivative and / or a pyrene derivative.
[0483] exist Figures 3 to 6 In each of the light-emitting elements ED of the embodiments described above, the emission layer EML may further include a suitable host and / or dopant in addition to the above-described host and dopant, and for example, in one or more embodiments, the emission layer EML may include a compound represented by Formula E-1. The compound represented by Formula E-1 may be used as a fluorescent host material.
[0484] Formula E-1
[0485]
[0486] In formula E-1, R 31 to R 40Each of the groups independently may be hydrogen, deuterium, halogen, substituted or unsubstituted silyl, substituted or unsubstituted thiol, substituted or unsubstituted oxy, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms and / or may be bonded to an adjacent group to form a ring. In one or more embodiments, the group selected from R 31 to R 40 One or more of them may each independently bond with an adjacent group to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated heterocyclic ring or an unsaturated heterocyclic ring.
[0487] In Formula E-1, c and d may each independently be an integer selected from 0 to 5.
[0488] The compound represented by formula E-1 may be any one selected from compound E1 to compound E19:
[0489]
[0490]
[0491] In one or more embodiments, the emission layer EML may include a compound represented by Formula E-2a or Formula E-2b. The compound represented by Formula E-2a or Formula E-2b may be used as a phosphorescent host material.
[0492] Formula E-2a
[0493]
[0494] In Formula E-2a, a may be an integer selected from 0 to 10, and L a It may be a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In one or more embodiments, if a is an integer of 2 or greater (for example, when a is an integer of 2 or greater), multiple L a Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.
[0495] In formula E-2a, A1 to A5 may each independently be N or CR i . R a to R iEach of the groups independently may be hydrogen, deuterium, a substituted or unsubstituted amino group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms and / or may be bonded to an adjacent group to form a ring. In one or more embodiments, the group selected from R a to R i One or more of them may be bonded to an adjacent group to form a hydrocarbon ring or a heterocyclic ring containing N, O and / or S as ring atoms.
[0496] In one or more embodiments, in Formula E-2a, two or three selected from A1 to A5 may be N, and the remaining may be CR i .
[0497] Formula E-2b
[0498]
[0499] In Formula E-2b, Cbz1 and Cbz2 may each independently be an unsubstituted carbazolyl group or a carbazolyl group substituted with an aryl group having 6 to 30 ring carbon atoms. b It may be a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In one or more embodiments, b may be an integer selected from 0 to 10, and if b is an integer of 2 or greater (for example, when b is an integer of 2 or greater), multiple L b Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.
[0500] The compound represented by Formula E-2a or Formula E-2b may be any one selected from the compounds listed in Compound Group E-2. However, the compounds listed in Compound Group E-2 are merely examples, and the compounds represented by Formula E-2a or Formula E-2b are not limited to the compounds listed in Compound Group E-2.
[0501] Compound Group E-2
[0502]
[0503]
[0504] In one or more embodiments, the emission layer EML may further include a general material suitable in the art as a host material. For example, the emission layer EML may include at least one of the following as a host material: bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide (POPCPA), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(N-carbazol-1,1'-biphenyl (CBP), 1,3-bis(N-carbazol-2-yl)benzene (mCP), 2,8-bis(diphenylphosphino)dibenzo[b,d]furan (PPF), 4,4',4"-tris(N-carbazol-3-yl)triphenylamine (TCTA), and 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi). However, the embodiments of the present disclosure are not limited thereto, and for example, tris(8-hydroxyquinoline)aluminum (Alq3), 9,10-di(naphthalene-2-yl)anthracene (ADN), 2-tert-butyl-9,10-di(naphthalene-2-yl)anthracene (TBADN), distyrylarene (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), 3,3'-bis(9H-carbazol-9-yl)-1,1'-biphenyl (mCBP), hexaphenylcyclotrisiloxane (DPSiO3) and / or octaphenylcyclotetrasiloxane (DPSiO4), etc. may be used as the host material.
[0505] In one or more embodiments, the emission layer EML may include a compound represented by Formula Ma. The compound represented by Formula Ma may serve as a phosphorescent dopant material.
[0506] Formula Ma
[0507]
[0508] In formula Ma, Y1 to Y4 and Z1 to Z4 can each independently be CR1 or N, R1 to R4 can each independently be hydrogen, deuterium, substituted or unsubstituted amine, substituted or unsubstituted thiol, substituted or unsubstituted oxy, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms and / or can be bonded to an adjacent group to form a ring. In formula Ma, m is 0 or 1, and n is 2 or 3. In formula Ma, if m is 0 (for example, when m is 0), n is 3, and if m is 1 (for example, when m is 1), n is 2.
[0509] The compound represented by the formula Ma can be used as a phosphorescent dopant.
[0510] The compound represented by formula Ma may be any one selected from compound M-a1 to compound M-a25. However, compound M-a1 to compound M-a25 are merely examples, and the compound represented by formula Ma is not limited to compound M-a1 to compound M-a25.
[0511]
[0512]
[0513] In one or more embodiments, the emission layer EML may further include a compound represented by any one selected from Formula Fa to Formula Fc. The compound represented by any one selected from Formula Fa to Formula Fc may be used as a fluorescent dopant material.
[0514] Style
[0515]
[0516] In the formula Fa, R a to R j Two of them may be independently substituted by *-NAr1Ar2. a to R j The other groups not substituted by *-NAr1Ar2 in the above-mentioned group may each independently be hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.
[0517] In *-NAr1Ar2, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in one or more embodiments, at least one of Ar1 and Ar2 may be a heteroaryl group containing O or S as a ring atom.
[0518] Formula Fb
[0519]
[0520] In formula Fb, R a and R b Each of Ar1 to Ar4 may be independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or may be bonded to an adjacent group to form a ring. Ar1 to Ar4 may be independently substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 ring carbon atoms.
[0521] In Formula Fb, U and V may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocycle having 2 to 30 ring carbon atoms. In one or more embodiments, at least one selected from Ar1 to Ar4 may be a heteroaryl group containing O or S as a ring atom.
[0522] In Formula Fb, the number of rings represented by U and V may be each independently 0 or 1. For example, in Formula Fb, if the number of U or V is 1 (for example, when the number of U or V is 1), one ring constitutes a part of the fused ring at the portion indicated by U or V, and if the number of U or V is 0 (for example, when the number of U or V is 0), there is no ring indicated by U or V. For example, if the number of U is 0 and the number of V is 1 (for example, when the number of U is 0 and the number of V is 1), or if the number of U is 1 and the number of V is 0 (for example, when the number of U is 1 and the number of V is 0), the fused ring having a fluorene core in Formula Fb may be a cyclic compound having four rings. In one or more embodiments, if the number of U and V is each 0 (for example, when the number of U and V is each 0), the fused ring having a fluorene core in Formula Fb may be a cyclic compound having three rings. In one or more embodiments, if the number of U and V is each 1 (for example, when the number of U and V is each 1), the condensed ring having a fluorene core in Formula Fb may be a cyclic compound having five rings.
[0523] Formula Fc
[0524]
[0525] In formula Fc, A1 and A2 can each independently be O, S, Se or NR m , and R m It may be hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 11 Each may independently be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted amino, substituted or unsubstituted boron, substituted or unsubstituted oxy, substituted or unsubstituted thiol, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms and / or may be bonded to an adjacent group to form a ring.
[0526] In one or more embodiments, in Formula Fc, A1 and A2 can each independently bond to a substituent of an adjacent ring to form a fused ring. For example, if A1 and A2 can each independently be NR m (For example, when A1 and A2 can each independently be NR m In one or more embodiments, A1 may be bonded to R4 or R5 to form a condensed ring. In one or more embodiments, A2 may be bonded to R7 or R8 to form a condensed ring.
[0527] In one or more embodiments, the emission layer EML may further include one or more selected from the following as appropriate dopant materials: styryl derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino) phenyl)-N-phenylaniline (N-BDAVBi) and 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi)), perylene and its derivatives (for example, 2,5,8,11-tetra-tert-butylperylene (TBP)), and pyrene and its derivatives (for example, 1,1'-dipyrene, 1,4-dipyrenylbenzene and 1,4-bis(N,N-diphenylamino)pyrene), etc.
[0528] In one or more embodiments, the emission layer EML may further include a suitable phosphorescent dopant material. For example, a metal complex containing iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm) may be used as a phosphorescent dopant. For example, bis(4,6-difluorophenylpyridyl-N,C2') picolinyl iridium (III) (FIrpic), bis(2,4-difluorophenylpyridyl)-tetrakis(1-pyrazolyl) borate iridium (III) (FIr6), or octaethylporphyrin platinum (PtOEP) may be used as a phosphorescent dopant. However, the embodiments of the present disclosure are not limited thereto.
[0529] In one or more embodiments, the emissive layer may include quantum dots.
[0530] In this disclosure, a quantum dot refers to a crystal of a semiconductor compound. Depending on the size of the crystal, the quantum dot can emit light at one or more suitable emission wavelengths. By adjusting the ratio of elements in the quantum dot compound, the quantum dot can emit light at one or more suitable emission wavelengths.
[0531] The quantum dots may have, for example, a diameter of about 1 nm to about 10 nm. In the present disclosure, when the quantum dots, a plurality of quantum dots, or quantum dot particles are spherical, "diameter" indicates the particle size or average particle size, and when the particles are non-spherical, "diameter" indicates the major axis length or average major axis length. The diameter of the particles can be measured using a scanning electron microscope or a particle size analyzer. As a particle size analyzer, for example, a HORIBA, LA-950 laser particle size analyzer can be used. When the size of the particles is measured using a particle size analyzer, the average particle size is referred to as D 50 . D 50 It refers to the average diameter of particles whose cumulative volume corresponds to 50 vol% in a particle size distribution (e.g., cumulative distribution), and refers to the value of the particle size corresponding to 50% from the smallest particle when the total number of particles in a distribution curve accumulated in order from the smallest particle size to the largest particle size is 100%.
[0532] The quantum dots may be synthesized by a wet chemical process, a metal organic chemical vapor deposition (MOCVD) process, a molecular beam epitaxy (MBE) process, and / or similar processes.
[0533] The wet chemical process is a method in which a precursor material of a quantum dot is mixed with an organic solvent to grow quantum dot particle crystals. As the quantum dot particle crystals grow, the organic solvent naturally acts as a dispersant that coordinates on the surface of the quantum dot particle crystals and controls the growth of the quantum dot particle crystals. Therefore, the wet chemical process can control the growth of quantum dot particle crystals through a process that is easier to perform than vapor deposition methods (such as metal organic chemical vapor deposition processes or molecular beam epitaxy processes) and is also performed at a low cost.
[0534] In one or more embodiments, the emission layer EML may include a quantum dot material. In one or more embodiments, the quantum dot may have a core / shell structure. The core of the quantum dot may be selected from a II-VI compound, a III-VI compound, a I-III-VI compound, a III-V compound, a III-II-V compound, a IV-VI compound, a Group IV element, a Group IV compound, and / or a combination thereof (e.g., any suitable combination).
[0535] The II-VI compound may be selected from the group consisting of a binary compound selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof (e.g., any suitable mixture); a ternary compound selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdS, and CdS; CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof (e.g., any suitable mixture); and a quaternary compound selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and mixtures thereof (e.g., any suitable mixture).
[0536] The Group III-VI compounds may include binary compounds (eg, In2S3 and / or In2Se3), ternary compounds (eg, InGaS3 and / or InGaSe3), or any combination thereof.
[0537] The Group I-III-VI compounds may be selected from: ternary compounds selected from the group consisting of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2 and mixtures thereof (e.g., any suitable mixtures); and / or quaternary compounds (e.g., AgInGaS, AgInGaS2, AgInGaSe, AgInGaSe2, CuInGaS and / or CuInGaS2).
[0538] The III-V compound may be selected from the group consisting of: a binary compound selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof (e.g., any suitable mixture); a ternary compound selected from the group consisting of GaNPs, GaNAs, GaNSb, GaPAs, GaPSb, AlNPs, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, In In one or more embodiments, the Group III-V compound may further include a Group II metal. For example, InZnP or the like may be selected as the Group III-II-V compound.
[0539] The Group IV-VI compound may be selected from the group consisting of a binary compound selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof (e.g., any suitable mixture); a ternary compound selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof (e.g., any suitable mixture); and a quaternary compound selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof (e.g., any suitable mixture). The Group IV element may be selected from the group consisting of Si, Ge, and mixtures thereof (e.g., any suitable mixture). The Group IV compound may be a binary compound selected from the group consisting of SiC, SiGe, and mixtures thereof (e.g., any suitable mixture).
[0540] Each element included in a multi-element compound (e.g., a binary compound, a ternary compound, or a quaternary compound) may be present in a substantially uniform or non-uniform concentration distribution in the particle. For example, the above formula refers to the type (species) of elements included in the compound, and the ratio of elements in the compound may be different. For example, AgInGaS2 may refer to AgInGaS2. x Ga 1-x S2 (where 0<x<1).
[0541] In one or more embodiments, the quantum dot may have a single structure in which the concentration of each element included in the quantum dot is substantially uniform, or may have a core / shell dual structure. For example, in the case of a core / shell dual structure, the material included in the core may be different from the material included in the shell.
[0542] The shell of a quantum dot can serve as a protective layer to prevent or reduce chemical degeneration of the core to maintain semiconductor properties and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient in which the concentration of the element present in the shell decreases toward the center of the core.
[0543] In one or more embodiments, the quantum dot may have the core / shell structure described above including a core containing nanocrystals and a shell around the core (e.g., surrounding the core). Examples of the shell of the quantum dot may include metal oxides, non-metal oxides, semiconductor compounds, and / or combinations thereof (e.g., any suitable combination).
[0544] For example, the metal oxide or non-metal oxide used for the shell may be a binary compound, such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4 and / or NiO; or a ternary compound, such as MgAl2O4, CoFe2O4, NiFe2O4 and / or CoMn2O4, but the embodiments of the present disclosure are not limited thereto.
[0545] Furthermore, examples of semiconductor compounds suitable as shells may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP and / or AlSb, etc., but embodiments of the present disclosure are not limited thereto.
[0546] Each element included in a polynary compound (e.g., a binary compound or a ternary compound) may be present in the particle in a substantially uniform or non-uniform concentration distribution. For example, a formula may refer to the type (species) of elements included in a compound, but the ratio of elements in the compound may be different.
[0547] The quantum dots may have an emission spectrum having a full width at half maximum (FWHM) of about 45 nm or less, about 40 nm or less, or about 30 nm or less, and within the above ranges, the color purity and / or color reproducibility of the quantum dots may be improved. In addition, light emitted by such quantum dots is emitted in all directions, thereby improving a wide viewing angle.
[0548] In addition, although the form of quantum dots is not particularly limited as long as it is a form commonly used in the art, quantum dots in the form of, for example, spherical nanoparticles, pyramidal nanoparticles, multi-arm nanoparticles, cubic nanoparticles, nanotubes, nanowires, nanofibers and / or nanoplates can be used.
[0549] As the size of the quantum dots is adjusted or the ratio of elements in the quantum dot compound is adjusted, the energy band gap of the quantum dots can be controlled, and thus light in one or more appropriate wavelength ranges can be obtained in the quantum dot emission layer. Therefore, when using quantum dots as above (for example, using quantum dots of different sizes or different ratios of elements in the quantum dot compound), a light-emitting element ED that emits light in one or more appropriate wavelength ranges can be implemented. For example, the size of the quantum dots or the ratio of elements in the quantum dot compound can be selected to ensure that the quantum dots emit red light, green light and / or blue light. In one or more embodiments, the quantum dots can be configured to emit white light by combining one or more appropriate colors of light.
[0550] exist Figures 3 to 6 In each of the light emitting elements ED of the embodiment illustrated in FIG, an electron transport region ETR may be provided on the emission layer EML. The electron transport region ETR may include at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL, but the embodiments of the present disclosure are not limited thereto.
[0551] The electron transport region ETR may have a single-layer structure of a single layer formed of a single material, a single-layer structure of a single layer formed of a plurality of different materials, or a multi-layer structure including a plurality of layers formed of a plurality of different materials.
[0552] For example, in one or more embodiments, the electron transport region ETR may have a single-layer structure of an electron injection layer EIL or an electron transport layer ETL or may have a single-layer structure formed of an electron injection material and / or an electron transport material. In one or more embodiments, the electron transport region ETR may have a single-layer structure formed of a plurality of different materials or may have a structure in which the electron transport layer ETL / electron injection layer EIL or the hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL are stacked in order (for example, in the order of description) from the emission layer EML, but the embodiments of the present disclosure are not limited thereto. The electron transport region ETR may have, for example, about to about thickness.
[0553] The electron transport region ETR may be formed using one or more appropriate methods such as vacuum deposition, spin coating, casting, Langmuir-Brockett (LB) method, inkjet printing, laser printing, and / or laser induced thermal imaging (LITI) method.
[0554] In one or more embodiments, the electron transport region ETR may include a compound represented by Formula ET-2:
[0555] Formula ET-2
[0556]
[0557] In formula ET-2, at least one selected from X1 to X3 may be N, and the rest may be CR a . R a Ar1 to Ar3 may each independently be hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.
[0558] In Formula ET-2, a to c may each independently be an integer selected from 0 to 10. In Formula ET-2, L1 to L3 may each independently be a directly attached, substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. In one or more embodiments, if a to c are each independently an integer of 2 or greater (for example, when a to c are each independently an integer of 2 or greater), multiple L1 to multiple L3 may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.
[0559] In one or more embodiments, the electron transport region ETR may include an anthracene compound. However, the embodiments of the present disclosure are not limited thereto, and the electron transport region ETR may include, for example, tris(8-hydroxyquinoline)aluminum (Alq3), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthothracene, 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene. )benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3-(biphenyl-4-yl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole ( t Bu-PBD), bis(2-methyl-8-hydroxyquinolinato-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinolinato-10-hydroxy)beryllium (Bebq2), 9,10-di(naphthalen-2-yl)anthracene (ADN), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB), and / or mixtures thereof (e.g., any suitable mixture).
[0560] In one or more embodiments, the electron transport region ETR may include at least one selected from the group consisting of compounds ET1 to ET36:
[0561]
[0562]
[0563]
[0564] In one or more embodiments, the electron transport region ETR may include a metal halide (e.g., LiF, NaCl, CsF, RbCl, RbI, CuI and / or KI), a lanthanide metal (e.g., Yb) or a co-deposited material of a metal halide and a lanthanide metal. For example, in one or more embodiments, the electron transport region ETR may include KI:Yb, RbI:Yb and / or LiF:Yb as a co-deposited material. In one or more embodiments, a metal oxide (e.g., Li2O and / or BaO) and / or 8-hydroxyquinoline lithium (Liq) may be used to form the electron transport region ETR, but the embodiments of the present disclosure are not limited thereto. The electron transport region ETR may also be formed from a mixture material of an electron transport material and an insulating organic metal salt. The insulating organic metal salt may be a material having an energy band gap of about 4 eV or greater. For example, the insulating organic metal salt may include, for example, one or more of a metal acetate, a metal benzoate, a metal acetoacetate, a metal acetylacetonate and a metal stearate.
[0565] In one or more embodiments, in addition to one or more of the above materials, the electron transport region ETR may further include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1) and 4,7-diphenyl-1,10-phenanthroline (Bphen), but the embodiments of the present disclosure are not limited thereto.
[0566] The electron transport region ETR may include one or more of the above-described compounds of the electron transport region ETR in at least one of the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.
[0567] If the electron transport region ETR includes the electron transport layer ETL (for example, when the electron transport region ETR includes the electron transport layer ETL), the electron transport layer ETL may have a thickness of about to about For example, about to about If the thickness of the electron transport layer ETL satisfies the aforementioned range (for example, when the thickness of the electron transport layer ETL satisfies the aforementioned range), satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage. If the electron transport region ETR includes the electron injection layer EIL (for example, when the electron transport region ETR includes the electron injection layer EIL), the electron injection layer EIL may have a thickness of about to about For example, about to about If the thickness of the electron injection layer EIL satisfies the above range (eg, when the thickness of the electron injection layer EIL satisfies the above range), satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0568] The second electrode EL2 may be provided on the electron transport region ETR. In one or more embodiments, the second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anode, but the embodiments of the present disclosure are not limited thereto. For example, if the first electrode EL1 is an anode (for example, when the first electrode EL1 is an anode), the second electrode EL2 may be a cathode, and if the first electrode EL1 is a cathode (for example, when the first electrode EL1 is a cathode), the second electrode EL2 may be an anode.
[0569] The second electrode EL2 may be a transmissive electrode, a transflective electrode, or a reflective electrode. If the second electrode EL2 is a transmissive electrode (for example, when the second electrode EL2 is a transmissive electrode), the second electrode EL2 may be formed of a transparent metal oxide, for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO).
[0570] If the second electrode EL2 is a transflective electrode or a reflective electrode (for example, when the second electrode EL2 is a transflective electrode or a reflective electrode), the second electrode EL2 may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, and W, a compound thereof, or a mixture thereof (for example, AgMg, AgYb, or MgYb), or a material having a multilayer structure, such as LiF / Ca (a stacked structure of LiF and Ca) or LiF / Al (a stacked structure of LiF and Al). In one or more embodiments, the second electrode EL2 may have a multilayer structure including a reflective film or a transflective film formed of one or more of the above materials, and a transparent conductive film formed of ITO, IZO, ZnO, and / or ITZO. For example, in one or more embodiments, the second electrode EL2 may include one of the above metal materials, a combination of at least two of the above metal materials (for example, any appropriate combination), and / or oxides of the above metal materials.
[0571] In one or more embodiments, the second electrode EL2 may be connected to an auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode (eg, when the second electrode EL2 is connected to the auxiliary electrode), resistance of the second electrode EL2 may be reduced.
[0572] In one or more embodiments, a capping layer CPL may be further disposed on the second electrode EL2 of the light emitting element ED of one or more embodiments. The capping layer CPL may include a plurality of layers or a single layer.
[0573] In one or more embodiments, the capping layer CPL may be an organic layer or an inorganic layer. For example, if the capping layer CPL contains an inorganic material (for example, when the capping layer CPL contains an inorganic material), the inorganic material may include an alkali metal compound (for example, LiF), an alkaline earth metal compound (for example, MgF2), SiON, SiN x and / or SiO y wait.
[0574] For example, in one or more embodiments, if the capping layer CPL includes an organic material (for example, when the capping layer CPL includes an organic material), the organic material may include N,N'-bis(naphthalene-1-yl)-N,N'-bis(phenyl)-2,2'-dimethylbenzidine (α-NPD), NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4,N4',N4'-tetrakis(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15) and / or 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), or may include an epoxy resin or an acrylate (for example, methacrylate). However, embodiments of the present disclosure are not limited thereto. For example, the capping layer CPL may include at least one selected from Compounds P1 to P5:
[0575]
[0576]
[0577] In one or more embodiments, the capping layer CPL may have a refractive index of about 1.6 or greater. For example, in one or more embodiments, the capping layer CPL may have a refractive index of about 1.6 or greater for light having a wavelength ranging from about 550 nm to about 660 nm.
[0578] Figures 7 to 10 Each of them is a cross-sectional view of a display device according to one or more embodiments of the present disclosure. Figures 7 to 10 When describing the display device of the embodiment, for the sake of brevity, the description of the display device in the embodiment will not be repeated. Figures 1 to 6 Instead of repeating the feature descriptions already described in , only their differences will be mainly described.
[0579] refer to Figure 7According to one or more embodiments, the display device DD-a may include a display panel DP including a display device layer DP-ED (also referred to as a display element layer), a light control layer CCL and a color filter layer CFL arranged on the display panel DP. Figure 7 In one or more embodiments explained in , the display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display device layer DP-ED, and the display device layer DP-ED may include a light emitting element ED.
[0580] The light emitting element ED may include a first electrode EL1, a hole transport region HTR disposed on the first electrode EL1, an emission layer EML disposed on the hole transport region HTR, an electron transport region ETR disposed on the emission layer EML, and a second electrode EL2 disposed on the electron transport region ETR. In one or more embodiments, the above Figures 3 to 6 The structure of any one of the light emitting elements ED can be similarly applied to Figure 7 The structure of the light-emitting element ED explained in .
[0581] The emission layer EML of the light emitting element ED included in the display device DD-a according to one or more embodiments may include the condensed polycyclic compound of the one or more embodiments described above.
[0582] refer to Figure 7 , the emission layer EML may be arranged in the opening OH defined in the pixel-defining film PDL. For example, the emission layer EML divided by the pixel-defining film PDL and provided to correspond to each of the emission areas PXA-R, PXA-G, and PXA-B may emit light within substantially the same wavelength range. In the display device DD-a of one or more embodiments, the emission layer EML may emit blue light. In one or more embodiments, the emission layer EML may be provided as a common layer throughout the entire emission areas PXA-R, PXA-G, and PXA-B.
[0583] The light control layer (CCL) may be disposed on the display panel DP. The light control layer (CCL) may include a light converter. The light converter may be, for example, quantum dots and / or phosphors. The light converter may convert the wavelength of provided light and emit converted light. For example, the light control layer (CCL) may be a layer containing quantum dots or a layer containing phosphors.
[0584] The light-control layer CCL may include a plurality of light-control parts CCP1, CCP2, and CCP3. The plurality of light-control parts CCP1, CCP2, and CCP3 may be spaced apart and / or separated (eg, spaced apart or separated) from each other.
[0585] refer to Figure 7, the dividing pattern BMP may be disposed between the light control parts CCP1 , CCP2 , and CCP3 that are spaced apart and / or separated (eg, spaced apart or separated) from each other, but embodiments of the present disclosure are not limited thereto. Figure 7 It is explained that the dividing pattern BMP does not overlap with the light control parts CCP1 , CCP2 , and CCP3 , however, in one or more embodiments, at least a portion of edges of the light control parts CCP1 , CCP2 , and CCP3 may overlap with the dividing pattern BMP.
[0586] The light control layer CCL may include: a first light control component CCP1, which contains first quantum dots QD1 that convert the first color light provided from the light emitting element ED into the second color light; a second light control component CCP2, which contains second quantum dots QD2 that convert the first color light into the third color light; and a third light control component CCP3 that transmits the first color light.
[0587] In one or more embodiments, the first light control component CCP1 may provide red light as the second color light, and the second light control component CCP2 may provide green light as the third color light. The third light control component CCP3 may provide blue light by transmitting blue light as the first color light provided by the light-emitting element ED. For example, in one or more embodiments, the first quantum dot QD1 may be a red quantum dot that emits red light, and the second quantum dot QD2 may be a green quantum dot that emits green light. The same contents as above regarding quantum dots apply to quantum dots QD1 and QD2.
[0588] In one or more embodiments, the light control layer CCL may further include a scatterer SP. The first light control component CCP1 may include first quantum dots QD1 and a scatterer SP, the second light control component CCP2 may include second quantum dots QD2 and a scatterer SP, and the third light control component CCP3 may not include (e.g., may exclude) any quantum dots but include a scatterer SP.
[0589] The scatterers SP may be inorganic particles. For example, the scatterers SP may include at least one of TiO2, ZnO, Al2O3, SiO2, and hollow silica. In one or more embodiments, the scatterers SP may include any one selected from TiO2, ZnO, Al2O3, SiO2, and hollow silica, or may be a mixture of at least two materials selected from TiO2, ZnO, Al2O3, SiO2, and hollow silica.
[0590] The first light control component CCP1, the second light control component CCP2, and the third light control component CCP3 may respectively include base resins BR1, BR2, and BR3 in which quantum dots QD1 and QD2 and scatterers SP are dispersed, respectively. In one or more embodiments, the first light control component CCP1 may include first quantum dots QD1 and scatterers SP dispersed in the first base resin BR1, the second light control component CCP2 may include second quantum dots QD2 and scatterers SP dispersed in the second base resin BR2, and the third light control component CCP3 may include scatterers SP dispersed in the third base resin BR3.
[0591] The base resins BR1, BR2, and BR3 are media in which the quantum dots QD1 and QD2 and the scatterers SP are dispersed, respectively, and may be formed from one or more suitable resin compositions, which may generally be referred to as binders. For example, the base resins BR1, BR2, and BR3 may each independently be an acrylic resin, a urethane resin, a silicone resin, and / or an epoxy resin, etc. The base resins BR1, BR2, and BR3 may each be a transparent resin. In one or more embodiments, the first base resin BR1, the second base resin BR2, and the third base resin BR3 may be the same as or different from each other.
[0592] In one or more embodiments, the light control layer CCL may include an isolation layer BFL1. The isolation layer BFL1 may be used to prevent or reduce the penetration of moisture and / or oxygen (hereinafter, referred to as "moisture / oxygen"). The isolation layer BFL1 may block the light control components CCP1, CCP2, and CCP3 from being exposed to moisture / oxygen. In one or more embodiments, the isolation layer BFL1 may cover the light control components CCP1, CCP2, and CCP3. In one or more embodiments, the isolation layer BFL2 may be provided between the light control components CCP1, CCP2, and CCP3 and the color filters CF1, CF2, and CF3.
[0593] Isolation layers BFL1 and BFL2 may each include at least one inorganic layer. For example, in one or more embodiments, isolation layers BFL1 and BFL2 may each include an inorganic material. For example, isolation layers BFL1 and BFL2 may each independently include silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride, and / or a metal film that ensures light transmittance. In one or more embodiments, isolation layers BFL1 and BFL2 may each independently further include an organic film. Isolation layers BFL1 and BFL2 may be formed of a single layer or multiple layers.
[0594] In the display device DD-a of one or more embodiments, the color filter layer CFL may be disposed on the light control layer CCL. For example, in one or more embodiments, the color filter layer CFL may be disposed directly on the light control layer CCL. In these embodiments, the isolation layer BFL2 may not be provided.
[0595] The color filter layer CFL may include color filters CF1, CF2, and CF3. The color filter layer CFL may include a first color filter CF1 configured to transmit a second color light, a second color filter CF2 configured to transmit a third color light, and a third color filter CF3 configured to transmit the first color light. For example, in one or more embodiments, the first color filter CF1 may be a red filter, the second color filter CF2 may be a green filter, and the third color filter CF3 may be a blue filter. The color filters CF1, CF2, and CF3 may each include a polymerized photosensitive resin and a pigment and / or dye. The first color filter CF1 may include a red pigment and / or a red dye, the second color filter CF2 may include a green pigment and / or a green dye, and the third color filter CF3 may include a blue pigment and / or a blue dye.
[0596] In one or more embodiments, the third color filter CF3 may not include (e.g., may exclude) any pigment or dye. The third color filter CF3 may include a polymerized photosensitive resin and may not include (e.g., may exclude) any pigment or dye. The third color filter CF3 may be transparent. The third color filter CF3 may be formed of a transparent photosensitive resin.
[0597] In addition, in one or more embodiments, the first color filter CF1 and the second color filter CF2 may each be a yellow filter. The first color filter CF1 and the second color filter CF2 may not be separated but provided as one color filter.
[0598] In one or more embodiments, the color filter layer CFL may further include a light shielding member. The light shielding member may be a black matrix. The light shielding member may include an organic light shielding material or an inorganic light shielding material containing a black pigment and / or a black dye. The light shielding member may prevent or reduce light leakage and may separate adjacent color filters CF1, CF2, and CF3.
[0599] The first to third color filters CF1 , CF2 , and CF3 may be arranged to correspond to the red, green, and blue light emitting regions PXA-R, PXA-G, and PXA-B, respectively.
[0600] In one or more embodiments, a base substrate BL may be disposed on the color filter layer CFL. The base substrate BL may be a member providing a base surface, on which the color filter layer CFL and / or the light control layer CCL are disposed. The base substrate BL may be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, embodiments of the present disclosure are not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. In one or more embodiments, the base substrate BL may not be provided.
[0601] Figure 8 A cross-sectional view illustrating a portion of a display device according to one or more embodiments. In the display devices DD-TD of one or more embodiments, the light-emitting element ED-BT may include a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3. The light-emitting element ED-BT may include a first electrode EL1 and a second electrode EL2 facing each other, and a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3 sequentially stacked in a thickness direction between the first electrode EL1 and the second electrode EL2. The light-emitting structures OL-B1, OL-B2, and OL-B3 may each include an emission layer EML ( Figure 7 ) and the hole transport region HTR( Figure 7 ) and electron transport region ETR( Figure 7 ), the emission layer EML is located between the hole transport region HTR and the electron transport region ETR.
[0602] For example, the light emitting elements ED-BT included in the display devices DD-TD of one or more embodiments may be light emitting elements having a tandem structure and including a plurality of emission layers EML.
[0603] exist Figure 8 In one or more embodiments described in the accompanying drawings, all light beams emitted from the light-emitting structures OL-B1, OL-B2, and OL-B3 may be blue light. However, the embodiments of the present disclosure are not limited thereto, and the light beams emitted from the light-emitting structures OL-B1, OL-B2, and OL-B3 may have different wavelength ranges. For example, in one or more embodiments, the light-emitting element ED-BT including a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3 emitting light beams having different wavelength ranges may emit white light (e.g., combined white light).
[0604] The charge generation layers CGL1 and CGL2 may be disposed between two adjacent light emitting structures OL-B1, OL-B2, and OL-B3, respectively. The charge generation layers CGL1 and CGL2 may each independently include a p-type (species) charge (e.g., P-charge) generation layer and / or an n-type (species) charge (e.g., N-charge) generation layer.
[0605] At least one of the light-emitting structures OL-B1, OL-B2, and OL-B3 included in the display devices DD-TD selected from one or more embodiments may include the fused polycyclic compound of one or more embodiments. For example, at least one of the multiple emission layers included in the light-emitting elements ED-BT may include the fused polycyclic compound of one or more embodiments.
[0606] refer to Figure 9 The display device DD-b according to one or more embodiments may include light emitting elements ED-1, ED-2, and ED-3, in each of which two emission layers are stacked. Figure 2 Compared to the display device DD of one or more embodiments described in Figure 9 The display device DD-b illustrated in FIG2 is different in that each of the first to third light-emitting elements ED-1, ED-2, and ED-3 includes two emission layers stacked in the thickness direction. In each of the first to third light-emitting elements ED-1, ED-2, and ED-3, the two emission layers can emit light in substantially the same wavelength region.
[0607] In one or more embodiments, the first light-emitting device ED-1 may include a first red emission layer EML-R1 and a second red emission layer EML-R2. The second light-emitting device ED-2 may include a first green emission layer EML-G1 and a second green emission layer EML-G2. In addition, the third light-emitting device ED-3 may include a first blue emission layer EML-B1 and a second blue emission layer EML-B2. The emission auxiliary component OG may be separately arranged between the first red emission layer EML-R1 and the second red emission layer EML-R2, between the first green emission layer EML-G1 and the second green emission layer EML-G2, and between the first blue emission layer EML-B1 and the second blue emission layer EML-B2.
[0608] The emission auxiliary component OG may include a single layer or multiple layers. The emission auxiliary component OG may include a charge generation layer. In one or more embodiments, the emission auxiliary component OG may include an electron transport region (not shown), a charge generation layer (not shown), and a hole transport region (not shown) stacked in sequence (for example, stacked in the order described). The emission auxiliary component OG may be provided as a common layer throughout the first to third light-emitting elements ED-1, ED-2, and ED-3. However, the embodiments of the present disclosure are not limited thereto, and the emission auxiliary component OG may be provided by patterning in an opening OH defined in the pixel defining film PDL.
[0609] The first red emission layer EML-R1, the first green emission layer EML-G1, and the first blue emission layer EML-B1 may each be arranged between the emission auxiliary component OG and the electron transport region ETR. The second red emission layer EML-R2, the second green emission layer EML-G2, and the second blue emission layer EML-B2 may each be arranged between the hole transport region HTR and the emission auxiliary component OG.
[0610] For example, in one or more embodiments, the first light-emitting element ED-1 may include a first electrode EL1, a hole transport region HTR, a second red emission layer EML-R2, an emission auxiliary component OG, a first red emission layer EML-R1, an electron transport region ETR, and a second electrode EL2 stacked in sequence (e.g., stacked in the order described). The second light-emitting element ED-2 may include a first electrode EL1, a hole transport region HTR, a second green emission layer EML-G2, an emission auxiliary component OG, a first green emission layer EML-G1, an electron transport region ETR, and a second electrode EL2 stacked in sequence (e.g., stacked in the order described). The third light-emitting element ED-3 may include a first electrode EL1, a hole transport region HTR, a second blue emission layer EML-B2, an emission auxiliary component OG, a first blue emission layer EML-B1, an electron transport region ETR, and a second electrode EL2 stacked in sequence (e.g., stacked in the order described).
[0611] In one or more embodiments, an optical auxiliary layer PL may be disposed on the display device layers DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL may be disposed on the display panel DP and control light reflected in the display panel DP due to external light. In one or more embodiments, the optical auxiliary layer PL may not be provided in the display devices DD-TD.
[0612] Figure 9 At least one emission layer included in the display device DD-b of one or more embodiments described above may include the fused polycyclic compound of the one or more embodiments. For example, in one or more embodiments, at least one of the first blue emission layer EML-B1 and the second blue emission layer EML-B2 may include the fused polycyclic compound of one or more embodiments.
[0613] and Figure 8 and Figure 9 different, Figure 10The display device DD-c is illustrated as including four light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1. The light-emitting element ED-CT may include a first electrode EL1 and a second electrode EL2 facing each other, and first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 stacked in the thickness direction between the first electrode EL1 and the second electrode EL2. The light-emitting structures OL-C1, OL-B1, OL-B2, and OL-B3 are stacked in sequence, and a charge generation layer CGL1 is disposed between the light-emitting structures OL-B1 and OL-C1, a charge generation layer CGL2 is disposed between the light-emitting structures OL-B1 and OL-B2, and a charge generation layer CGL3 is disposed between the light-emitting structures OL-B2 and OL-B3. In one or more embodiments, among the four light-emitting structures, the first to third light-emitting structures OL-B1, OL-B2, and OL-B3 may emit blue light, and the fourth light-emitting structure OL-C1 may emit green light. However, the embodiments of the present disclosure are not limited thereto, and the first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may emit light beams in different wavelength regions.
[0614] The charge generation layers CGL1, CGL2, and CGL3 arranged between adjacent light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may each independently include a p-type (kind) charge (e.g., P-charge) generation layer and / or an n-type (kind) charge (e.g., N-charge) generation layer.
[0615] At least one of the light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 included in the display device DD-c selected from one or more embodiments may include the fused polycyclic compound of the one or more embodiments described above. For example, in one or more embodiments, at least one of the first to third light-emitting structures OL-B1, OL-B2, and OL-B3 may include the fused polycyclic compound of the one or more embodiments described above.
[0616] The light-emitting element ED according to one or more embodiments of the present disclosure may include the fused polycyclic compound represented by Formula 1 according to one or more embodiments in at least one functional layer disposed between the first electrode EL1 and the second electrode EL2, thereby exhibiting excellent or appropriate luminous efficiency and improved element life characteristics. For example, the fused polycyclic compound according to one or more embodiments may be included in the emission layer EML of the light-emitting element ED according to one or more embodiments, and the light-emitting element ED according to one or more embodiments may exhibit long element life characteristics.
[0617] In one or more embodiments, the electronic device may include: a display device including a plurality of light-emitting elements and a control unit for controlling the display device. The electronic device of one or more embodiments may be a device activated by an electrical signal. The electronic device may include a display device of one or more appropriate embodiments. For example, the electronic device may include not only large electronic devices (such as televisions, monitors, or outdoor billboards), but also small and medium-sized electronic devices (such as personal computers, laptop computers, personal digital assistants, display devices for vehicles, game consoles, portable electronic devices, or cameras).
[0618] Figure 11 For explaining a view of a vehicle AM in which first to fourth display devices DD-1, DD-2, DD-3 and DD-4 are arranged. At least one selected from the first to fourth display devices DD-1, DD-2, DD-3 and DD-4 may include Figure 1 and Figure 2 as well as Figures 7 to 10 The description shows one identical configuration among the display devices DD, DD-TD, DD-a, DD-b, and DD-c.
[0619] Figure 11 The vehicle AM is described, but this is merely an example, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may be arranged in other transportation equipment (e.g., bicycles, motorcycles, trains, ships, and / or airplanes). In one or more embodiments, at least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4, selected from the display devices DD, DD-TD, DD-a, DD-b, and DD-c of one or more embodiments, may be used in a personal computer, a laptop computer, a personal digital assistant, a game console, a portable electronic device, a television, a monitor, and / or an outdoor billboard. These are provided merely as example embodiments, and therefore, the display devices may be used in other electronic devices unless departing from the present disclosure.
[0620] At least one selected from the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include a reference Figures 3 to 6 The light-emitting element ED according to one or more embodiments is described.
[0621] The light-emitting element ED of one or more embodiments may include the fused polycyclic compound of one or more embodiments. At least one selected from the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include a light-emitting element ED including the fused polycyclic compound of one or more embodiments, thereby improving display life.
[0622] refer to Figure 11 The vehicle AM may include a steering wheel HA and a gearshift GR for driving the vehicle AM. In addition, the vehicle AM may include a front window GL arranged to face the driver.
[0623] The first display device DD-1 may be arranged in a first area overlapping the steering wheel HA. For example, the first display device DD-1 may be a digital instrument panel displaying first information about the vehicle AM. The first information may include a first scale indicating the driving speed of the vehicle AM, a second scale indicating the engine speed (i.e., revolutions per minute (RPM)), and / or an image indicating the fuel status. The first scale and the second scale may each be displayed as a digital image.
[0624] The second display device DD-2 may be arranged in a second area opposite to (e.g., facing) the driver's seat and overlapping the front window GL. The driver's seat may be a seat facing the steering wheel HA. For example, the second display device DD-2 may be a head-up display (HUD) that displays second information of the vehicle AM. The second display device DD-2 may be optically transparent. The second information may include a numerical value indicating the driving speed and may further include information such as the current time. In one or more embodiments, the second information of the second display device DD-2 may be projected onto the front window GL to be displayed.
[0625] The third display device DD-3 may be positioned in a third area adjacent to the gearshift GR. For example, the third display device DD-3 may be positioned between the driver's seat and the passenger seat and may be a central information display (CID) for the vehicle AM, for displaying third information. The passenger seat may be a seat that is separate and / or detached (e.g., spaced or separated) from the driver's seat, with the gearshift GR positioned between the passenger seat and the driver's seat. The third information may include information about traffic (e.g., navigation information), information about music, radio, or video (or images), and / or information about the temperature inside the vehicle AM.
[0626] The fourth display device DD-4 may be separate and / or detachable (e.g., spaced apart or separated) from the steering wheel HA and the gearshift GR and may be positioned in a fourth area adjacent to the side of the vehicle AM. For example, the fourth display device DD-4 may be a digital sideview mirror that displays the fourth information. The fourth display device DD-4 may display an image of the exterior of the vehicle AM captured by a camera module CM positioned outside the vehicle AM. The fourth information may include an image of the exterior of the vehicle AM.
[0627] The first to fourth information items are examples, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may further display information about the interior and exterior of the vehicle AM. The first to fourth information items may each include different information. However, embodiments of the present disclosure are not limited thereto, and some of the first to fourth information items may include the same information.
[0628] Hereinafter, with reference to Examples and Comparative Examples, the fused polycyclic compound according to one or more embodiments of the present disclosure and the light-emitting element according to one or more embodiments will be described in more detail. In addition, the Examples described herein are only explained to facilitate understanding of the present disclosure, and the scope of the present disclosure is not limited thereto.
[0629] Example
[0630] 1. Synthesis of the fused polycyclic compound of the embodiment
[0631] First, the synthesis method of the fused polycyclic compound according to the exemplary embodiment will be described in more detail by explaining the synthesis method of Compound 1, Compound 3, Compound 4, Compound 9, Compound 13, Compound 23, Compound 33, Compound 49, Compound 67, Compound 93, and Compound 131 as fused polycyclic compounds. In addition, the synthesis method of the fused polycyclic compound as described herein is only an example, and the synthesis method of the fused polycyclic compound according to one or more embodiments of the present disclosure is not limited to the following examples.
[0632] (1) Synthesis of fused polycyclic compound 1
[0633]
[0634]
[0635]
[0636] Synthesis of intermediate 1-(1)
[0637] In an Ar atmosphere, 1,3-dibromo-5-fluorobenzene (6.42 g, 25.29 mmol) and [1,1'-biphenyl]-4-ol (5.16 g, 30.34 mmol), K2CO3 (15.73 g, 113.78 mmol) and N-methylpyrrolidone (NMP) (64 mL) were added and mixed, and the resulting mixture was heated for about 24 hours while maintaining the ambient temperature at about 140°C. The mixture was then cooled and diluted with CH2Cl2, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and then liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 1-(1) (8.58 g, yield: 84%). The molecular weight of intermediate 1-(1) was about 404 as measured by fast atom bombardment mass spectrometry (FAB MS).
[0638] Synthesis of intermediate 1-(2)
[0639] In an Ar atmosphere, intermediate 1-(1) (8.33 g, 20.61 mmol), N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine (7.29 g, 22.68 mmol), Pd(OAc)2 (0.14 g, 0.62 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) (XantPhos) (0.72 g, 1.24 mmol) and tBuONa (2.38 g, 24.74 mmol) were added to 103 mL of toluene, and the resulting mixture was heated at about 100 ° C. and stirred for about 8 hours. After cooling to room temperature, water was added thereto, and the resulting mixture was filtered through celite, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 1-(2) (11.69 g, yield: 88%). The molecular weight of intermediate 1-(2) was about 645 as measured by FAB MS.
[0640] Synthesis of intermediate 1-(3)
[0641] In an Ar atmosphere, 1-bromo-3-(tert-butyl)-5-fluorobenzene (6.23 g, 26.96 mmol), naphthalene-1-ol (4.66 g, 32.35 mmol) and K CO (16.77 g, 121.31 mmol) are added to 62 mL of NMP, and while ambient temperature is maintained at approximately 140 ° C, the resulting mixture is heated for approximately 24 hours. The mixture is then cooled and diluted with CH Cl, water is added thereto, and the resulting mixture is filtered through diatomaceous earth, and then liquid separation is carried out to concentrate the organic layer. The organic layer is purified by silica gel column chromatography to provide intermediate 1-(3) (8.62 g, yield: 90%). As measured by FAB MS, the molecular weight of intermediate 1-(3) is approximately 355.
[0642] Synthesis of intermediate 1-(4)
[0643] In an Ar atmosphere, intermediate 1-(3) (8.51 g, 23.95 mmol), [1,1':3',1"-terphenyl]-2'-amine (7.05 g, 28.74 mmol), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2) (1.38 g, 2.4 mmol), P(tBu)3·HBF4 (1.39 g, 4.79 mmol) and tBuONa (5.29 g, 55.09 mmol) were added to 119 mL of toluene, and the resulting mixture was heated at about 100°C and stirred for about 8 hours. After cooling to room temperature, water was added thereto, and the resulting mixture was filtered through celite, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 1-(4) (10.95 g, yield: 88%). The molecular weight of intermediate 1-(4) was about 520 as measured by FAB MS.
[0644] Synthesis of intermediate 1-(5)
[0645] A small amount of toluene (about 10 mL) was added to intermediate 1-(4) (1.80 g, 3.46 mmol), intermediate 1-(2) (11.16 g, 17.32 mmol), CuI (1.39 g, 7.27 mmol) and KCO (4.79 g, 34.64 mmol), and the resulting mixture was heated for about 24 hours while maintaining the ambient temperature at about 215° C. The mixture was then cooled and diluted with CHCl, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 1-(5) (2.78 g, yield: 74%). The molecular weight of intermediate 1-(5) was about 1083 as measured by FAB MS.
[0646] Synthesis of compound 1
[0647] In an Ar atmosphere, intermediate 1-(5) (2.62 g, 2.42 mmol) is dissolved in o-dichlorobenzene (ODCB) (24 mL), BBr3 (1.21 g, 4.84 mmol) is added thereto, and the resulting mixture is heated at about 170 ° C and stirred for about 10 hours. Then, the mixture is cooled to room temperature, N, N-diisopropylethylamine (DIPEA) (3.74 g, 29.02 mmol) is added thereto, water is added thereto, and the resulting mixture is filtered through diatomaceous earth, and liquid separation is performed to concentrate the organic layer. The organic layer is purified by silica gel column chromatography to obtain compound 1 (0.88 g, yield: 33%). As measured by FAB MS, the molecular weight of compound 1 is about 1099.
[0648] By sublimation (350℃, 2.7×10 -3 Pa) was further purified and used for the evaluation of light-emitting device characteristics.
[0649] (2) Synthesis of fused polycyclic compound 3
[0650]
[0651]
[0652] Synthesis of intermediate 3-(1)
[0653] In an Ar atmosphere, 1-bromo-3-(tert-butyl)-5-fluorobenzene (5.32 g, 23.02 mmol), phenanthrene-9-ol (5.37 g, 27.62 mmol) and K CO (14.32 g, 103.59 mmol) are added to 53 mL of NMP, and while ambient temperature is maintained at approximately 140 ° C, the resulting mixture is heated for approximately 24 hours. The mixture is then cooled and diluted with CH Cl, water is added thereto, and the resulting mixture is filtered through diatomaceous earth, and liquid separation is performed to concentrate the organic layer. The organic layer is purified by silica gel column chromatography to provide intermediate 3- (1) (8.12 g, yield: 87%). As measured by FAB MS, the molecular weight of intermediate 3- (1) is approximately 405.
[0654] Synthesis of intermediate 3-(2)
[0655] In an Ar atmosphere, intermediate 3-(1) (7.75 g, 19.12 mmol), [1,1':3',1"-terphenyl]-2'-amine (5.63 g, 22.94 mmol), Pd(dba)2 (1.1 g, 1.91 mmol), P(tBu)3·HBF4 (1.11 g, 3.82 mmol) and tBuONa (4.23 g, 43.98 mmol) were added to 95 mL of toluene, and the resulting mixture was heated at about 100°C and stirred for about 8 hours. After cooling to room temperature, water was added thereto, and the resulting mixture was filtered through celite, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 3-(2) (9.15 g, yield: 84%). The molecular weight of intermediate 3-(2) was about 570 as measured by FAB MS.
[0656] Synthesis of intermediate 3-(3)
[0657] A small amount of toluene (about 10 mL) was added to intermediate 3-(2) (2.3 g, 4.04 mmol), intermediate 1-(2) (13.01 g, 20.18 mmol), CuI (1.61 g, 8.48 mmol) and KCO (5.58 g, 40.37 mmol), and the resulting mixture was heated for about 24 hours while maintaining the ambient temperature at about 215° C. The mixture was then cooled and diluted with CHCl, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 3-(3) (3.57 g, yield: 78%). The molecular weight of intermediate 3-(3) was about 1133 as measured by FAB MS.
[0658] Synthesis of compound 3
[0659] In an Ar atmosphere, intermediate 3-(3) (3.22 g, 2.84 mmol) was dissolved in ODCB (28 mL), BBr (1.42 g, 5.68 mmol) was added thereto, and the resulting mixture was heated at approximately 170 ° C and stirred for approximately 10 hours. The mixture was then cooled to room temperature, DIPEA (4.4 g, 34.09 mmol) was added thereto, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to obtain compound 3 (1.24 g, yield: 38%). The molecular weight of compound 3 was approximately 1149 as measured by FAB MS.
[0660] By sublimation (370℃, 2.8×10 -3Pa) was further purified and used for the evaluation of light-emitting device characteristics.
[0661] (3) Synthesis of fused polycyclic compound 4
[0662]
[0663]
[0664] Synthesis of intermediate 4-(1)
[0665] In an Ar atmosphere, 1-bromo-3-(tert-butyl)-5-fluorobenzene (4.11 g, 17.78 mmol), pyrene-4-ol (4.66 g, 21.34 mmol) and K CO (11.06 g, 80.03 mmol) were added to 41 mL of NMP and the resulting mixture was heated for about 24 hours while maintaining the ambient temperature at about 140° C. The mixture was then cooled and diluted with CH Cl, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 4-(1) (6.18 g, yield: 81%). The molecular weight of intermediate 4-(1) was about 429 as measured by FAB MS.
[0666] Synthesis of intermediate 4-(2)
[0667] In an Ar atmosphere, intermediate 4-(1) (5.95 g, 13.86 mmol), [1,1':3',1"-terphenyl]-2'-amine (4.08 g, 16.63 mmol), Pd(dba)2 (0.8 g, 1.39 mmol), P(tBu)3·HBF4 (0.8 g, 2.77 mmol) and tBuONa (3.06 g, 31.87 mmol) were added to 69 mL of toluene, and the resulting mixture was heated at about 100°C and stirred for about 8 hours. After cooling to room temperature, water was added thereto, and the resulting mixture was filtered through celite, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 4-(2) (7.32 g, yield: 89%). The molecular weight of intermediate 4-(2) was about 594 as measured by FAB MS.
[0668] Synthesis of intermediate 4-(3)
[0669] A small amount of toluene (about 10 mL) was added to intermediate 4-(2) (3.14 g, 5.29 mmol), intermediate 1-(2) (17.04 g, 26.44 mmol), CuI (2.12 g, 11.11 mmol) and KCO (7.31 g, 52.88 mmol), and the resulting mixture was heated for about 24 hours while maintaining the ambient temperature at about 215° C. The mixture was then cooled and diluted with CHCl, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 4-(3) (4.47 g, yield: 73%). The molecular weight of intermediate 4-(3) was about 1157 as measured by FAB MS.
[0670] Synthesis of compound 4
[0671] In an Ar atmosphere, intermediate 4-(3) (4.13 g, 3.64 mmol) was dissolved in ODCB (36 mL), BBr (1.83 g, 7.29 mmol) was added thereto, and the resulting mixture was heated at approximately 170 ° C and stirred for approximately 10 hours. The mixture was then cooled to room temperature, DIPEA (5.64 g, 43.72 mmol) was added thereto, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to obtain compound 4 (1.21 g, yield: 29%). The molecular weight of compound 4 was approximately 1149 as measured by FAB MS.
[0672] By sublimation (370℃, 2.6×10 -3 Pa) was further purified and used for the evaluation of light-emitting device characteristics.
[0673] (4) Synthesis of fused polycyclic compound 9
[0674]
[0675]
[0676] Synthesis of intermediate 9-(1)
[0677] In an Ar atmosphere, 3-bromonaphthalene-1-ol (4.11 g, 17.63 mmol), 3-fluoro-1,1'-biphenyl (3.64 g, 21.16 mmol) and K2CO3 (10.97 g, 79.35 mmol) were added to 41 mL of NMP and the resulting mixture was heated for about 24 hours while maintaining the ambient temperature at about 140°C. The mixture was then cooled and diluted with CH2Cl2, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 9-(1) (5.16 g, yield: 78%). The molecular weight of intermediate 9-(1) was about 375 as measured by FAB MS.
[0678] Synthesis of intermediate 9-(2)
[0679] In an Ar atmosphere, intermediate 9-(1) (4.88 g, 13 mmol), [1,1':3',1"-terphenyl]-2'-amine (3.83 g, 15.6 mmol), Pd(dba)2 (0.75 g, 1.3 mmol), P(tBu)3·HBF4 (0.75 g, 2.6 mmol) and tBuONa (2.87 g, 29.91 mmol) were added to 65 mL of toluene, and the resulting mixture was heated at about 100°C and stirred for about 8 hours. After cooling to room temperature, water was added thereto, and the resulting mixture was filtered through celite, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 9-(2) (5.97 g, yield: 85%). The molecular weight of intermediate 9-(2) was about 540 as measured by FAB MS.
[0680] Synthesis of intermediate 9-(3)
[0681] A small amount of toluene (about 10 mL) was added to intermediate 9-(2) (5.56 g, 10.3 mmol), intermediate 1-(2) (33.21 g, 51.51 mmol), CuI (4.12 g, 21.64 mmol) and KCO (14.24 g, 103.02 mmol), and the resulting mixture was heated for about 24 hours while maintaining the ambient temperature at about 215° C. The mixture was then cooled and diluted with CHCl, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 9-(3) (8.75 g, yield: 77%). The molecular weight of intermediate 9-(3) was about 1103 as measured by FAB MS.
[0682] Synthesis of compound 9
[0683] In an Ar atmosphere, intermediate 9-(3) (8.58 g, 7.78 mmol) was dissolved in ODCB (78 mL), BBr (3.9 g, 15.55 mmol) was added thereto, and the resulting mixture was heated at approximately 170 ° C and stirred for approximately 10 hours. The mixture was then cooled to room temperature, DIPEA (12.04 g, 93.31 mmol) was added thereto, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to obtain compound 9 (2.09 g, yield: 24%). The molecular weight of compound 9 was approximately 1119 as measured by FAB MS.
[0684] By sublimation (340℃, 2.7×10 -3 Pa) was further purified and used for the evaluation of light-emitting device characteristics.
[0685] (5) Synthesis of fused polycyclic compound 13
[0686]
[0687]
[0688]
[0689] Synthesis of intermediate 13-(1)
[0690] In an Ar atmosphere, 1,3-dibromo-5-fluorobenzene (5.02 g, 19.77 mmol), naphthalene-2-ol (3.42 g, 23.73 mmol) and K2CO3 (12.3 g, 88.97 mmol) were added to 50 mL of NMP and the resulting mixture was heated for about 24 hours while maintaining the ambient temperature at about 140 ° C. The mixture was then cooled and diluted with CH2Cl2, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 13-(1) (5.83 g, yield: 78%). The molecular weight of intermediate 13-(1) was about 378 as measured by FAB MS.
[0691] Synthesis of intermediate 13-(2)
[0692] In an Ar atmosphere, intermediate 13-(1) (5.66 g, 14.97 mmol), N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine (5.29 g, 16.47 mmol), Pd(OAc)2 (0.1 g, 0.45 mmol), XantPhos (0.52 g, 0.9 mmol) and tBuONa (1.73 g, 17.97 mmol) were added to 74 mL of toluene, and the resulting mixture was heated at about 100 ° C and stirred for about 8 hours. After cooling to room temperature, water was added thereto, and the resulting mixture was filtered through celite, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 13-(2) (8.06 g, yield: 87%). The molecular weight of intermediate 13-(2) was about 619 as measured by FAB MS.
[0693] Synthesis of intermediate 13-(3)
[0694] In an Ar atmosphere, 1,3-dibromo-5-(tert-butyl)benzene (6.04 g, 20.68 mmol), [1,1':3',1"-terphenyl]-2'-amine (12.69 g, 51.71 mmol), Pd(dba)2 (1.19 g, 2.07 mmol), P(t-Bu)3·HBF4 (1.2 g, 4.14 mmol) and tBuONa (4.57 g, 47.57 mmol) were added to 103 mL of toluene, and the resulting mixture was heated at about 100°C and stirred for about 8 hours. After cooling to room temperature, water was added thereto, and the resulting mixture was filtered through celite, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 13-(3) (11.43 g, yield: 89%). The molecular weight of intermediate 13-(3) was about 621 as measured by FAB MS.
[0695] Synthesis of intermediate 13-(4)
[0696] A small amount of toluene (about 10 mL) was added to intermediate 13-(3) (11.03 g, 20.44 mmol), 3-iodo-1,1'-biphenyl (28.62 g, 102.19 mmol), CuI (8.17 g, 42.92 mmol) and KCO (28.25 g, 204.38 mmol), and the resulting mixture was heated for about 24 hours while maintaining the ambient temperature at about 215°C. The mixture was then cooled and diluted with CHCl, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 13-(4) (7.58 g, yield: 48%). The molecular weight of intermediate 13-(4) was about 773 as measured by FAB MS.
[0697] Synthesis of intermediate 13-(5)
[0698] A small amount of toluene (about 10 mL) was added to intermediate 13-(4) (2.88 g, 3.73 mmol), intermediate 13-(2) (11.52 g, 18.63 mmol), CuI (1.49 g, 7.82 mmol) and KCO (5.15 g, 37.26 mmol), and the resulting mixture was heated for about 24 hours while maintaining the ambient temperature at about 215° C. The mixture was then cooled and diluted with CHCl, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 13-(5) (3.61 g, yield: 74%). The molecular weight of intermediate 13-(5) was about 1311 as measured by FAB MS.
[0699] Synthesis of compound 13
[0700] In an Ar atmosphere, intermediate 13-(5) (3.22 g, 2.46 mmol) was dissolved in ODCB (25 mL), BBr was added thereto (1.23 g, 4.91 mmol), and the resulting mixture was heated at approximately 170 ° C and stirred for approximately 10 hours. The mixture was then cooled to room temperature, DIPEA (3.8 g, 29.48 mmol) was added thereto, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to obtain compound 13 (1.82 g, yield: 56%). The molecular weight of compound 13 was approximately 1326 as measured by FAB MS.
[0701] By sublimation (350℃, 2.4×10 -3Pa) was further purified and used for the evaluation of light-emitting device characteristics.
[0702] (6) Synthesis of fused polycyclic compound 23
[0703]
[0704] Synthesis of intermediate 23-(1)
[0705] In an Ar atmosphere, intermediate 1-(1) (5.23 g, 12.94 mmol), N-([1,1'-biphenyl]-2-yl)naphthalene-2-amine (4.21 g, 14.24 mmol), Pd(OAc)2 (0.09 g, 0.39 mmol), XantPhos (0.45 g, 0.78 mmol) and tBuONa (1.49 g, 15.53 mmol) were added to 64 mL of toluene, and the resulting mixture was heated at about 100° C. and stirred for about 8 hours. After cooling to room temperature, water was added thereto, and the resulting mixture was filtered through celite, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 23-(1) (6.00 g, yield: 75%). The molecular weight of intermediate 23-(1) was about 619 as measured by FAB MS.
[0706] Synthesis of intermediate 23-(2)
[0707] A small amount of toluene (about 10 mL) was added to intermediate 23-(1) (5.89 g, 9.52 mmol), intermediate 13-(4) (36.8 g, 47.61 mmol), CuI (3.81 g, 20 mmol) and KCO (13.16 g, 95.22 mmol), and the resulting mixture was heated for about 24 hours while maintaining the ambient temperature at about 215° C. The mixture was then cooled and diluted with CHCl, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 23-(2) (8.86 g, yield: 71%). The molecular weight of intermediate 23-(2) was about 1311 as measured by FAB MS.
[0708] Synthesis of compound 23
[0709] In an Ar atmosphere, intermediate 23-(2) (8.55 g, 6.52 mmol) was dissolved in ODCB (65 mL), BBr was added thereto (3.27 g, 13.05 mmol), and the resulting mixture was heated at approximately 170 ° C and stirred for approximately 10 hours. The mixture was then cooled to room temperature, DIPEA (10.1 g, 78.28 mmol) was added thereto, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to obtain compound 23 (3.89 g, yield: 45%). The molecular weight of compound 23 was approximately 1326 as measured by FAB MS.
[0710] By sublimation (360℃, 2.8×10 -3 Pa) was further purified and used for the evaluation of light-emitting device characteristics.
[0711] (7) Synthesis of fused polycyclic compound 33
[0712]
[0713]
[0714]
[0715] Synthesis of intermediate 33-(1)
[0716] A small amount of toluene (about 10 mL) was added to intermediate 13-(3) (8.36 g, 13.47 mmol), 1-chloro-3-iodobenzene (16.05 g, 67.33 mmol), CuI (5.39 g, 28.28 mmol) and KCO (18.61 g, 134.66 mmol), and the resulting mixture was heated for about 24 hours while maintaining the ambient temperature at about 215° C. The mixture was then cooled and diluted with CHCl, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 33-(1) (4.04 g, yield: 41%). The molecular weight of intermediate 33-(1) was about 731 as measured by FAB MS.
[0717] Synthesis of intermediate 33-(2)
[0718] A small amount of toluene (about 10 mL) was added to intermediate 33-(1) (2.33 g, 3.19 mmol), intermediate 13-(2) (9.85 g, 15.93 mmol), CuI (1.27 g, 6.69 mmol) and KCO (4.4 g, 31.86 mmol), and the resulting mixture was heated for about 24 hours while maintaining the ambient temperature at about 215° C. The mixture was then cooled and diluted with CHCl, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 33-(2) (2.51 g, yield: 62%). The molecular weight of intermediate 33-(2) was about 1269 as measured by FAB MS.
[0719] Synthesis of intermediate 33-(3)
[0720] In an Ar atmosphere, intermediate 33-(2) (2.41 g, 1.9 mmol) was dissolved in ODCB (19 mL), BBr (0.95 g, 3.8 mmol) was added thereto, and the resulting mixture was heated at about 170 ° C and stirred for about 10 hours. The mixture was then cooled to room temperature, DIPEA (2.94 g, 22.79 mmol) was added thereto, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 33-(3) (1.34 g, yield: 55%). The molecular weight of intermediate 33-(3) was about 1285 as measured by FAB MS.
[0721] Synthesis of compound 33
[0722] In an Ar atmosphere, intermediate 33-(3) (1.22 g, 0.95 mmol), 9H-carbazole (0.19 g, 1.14 mmol), Pd(dba)2 (0.05 g, 0.09 mmol), P(tBu)3·HBF4 (0.06 g, 0.19 mmol) and tBuONa (0.21 g, 2.18 mmol) were added to 4 mL of toluene, and the resulting mixture was heated at about 100°C and stirred for about 8 hours. After cooling to room temperature, water was added thereto, and the resulting mixture was filtered through celite, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to obtain compound 33 (1.14 g, yield: 85%). As measured by FAB MS, the molecular weight of compound 33 was about 1415.
[0723] By sublimation (370℃, 2.8×10 -3Pa) was further purified and used for the evaluation of light-emitting device characteristics.
[0724] (8) Synthesis of fused polycyclic compound 49
[0725]
[0726]
[0727]
[0728] Synthesis of intermediate 49-(1)
[0729] In an Ar atmosphere, 1,3-dibromo-5-fluorobenzene (4.58 g, 18.04 mmol) and 3-chlorophenol (2.78 g, 21.65 mmol) and K2CO3 (11.22 g, 81.17 mmol) were added to 45 mL of NMP and the resulting mixture was heated for about 24 hours while maintaining the ambient temperature at about 140 ° C. The mixture was then cooled and diluted with CH2Cl2, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 49-(1) (5.75 g, yield: 88%). The molecular weight of intermediate 49-(1) was about 362 as measured by FAB MS.
[0730] Synthesis of intermediate 49-(2)
[0731] In an Ar atmosphere, intermediate 49-(1) (5.44 g, 13.46 mmol), N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine (4.76 g, 14.81 mmol), Pd(OAc)2 (0.09 g, 0.4 mmol), XantPhos (0.47 g, 0.81 mmol) and tBuONa (1.55 g, 16.15 mmol) were added to 67 mL of toluene, and the resulting mixture was heated at about 100 ° C and stirred for about 8 hours. After cooling to room temperature, water was added thereto, and the resulting mixture was filtered through celite, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 49-(2) (7.22 g, yield: 89%). The molecular weight of intermediate 49-(2) was about 603 as measured by FAB MS.
[0732] Synthesis of intermediate 49-(3)
[0733] A small amount of toluene (about 10 mL) was added to intermediate 1-(4) (1.21 g, 2.33 mmol), intermediate 49-(2) (7.02 g, 11.64 mmol), CuI (0.93 g, 4.89 mmol) and KCO (3.22 g, 23.28 mmol), and the resulting mixture was heated for about 24 hours while maintaining the ambient temperature at about 215° C. The mixture was then cooled and diluted with CHCl, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 49-(3) (1.89 g, yield: 78%). The molecular weight of intermediate 49-(3) was about 1042 as measured by FAB MS.
[0734] Synthesis of intermediate 49-(4)
[0735] In an Ar atmosphere, intermediate 49-(3) (1.54 g, 1.48 mmol) was dissolved in ODCB (15 mL), BBr 3 (0.74 g, 2.96 mmol) was added thereto, and the resulting mixture was heated at about 170° C. and stirred for about 10 hours. The mixture was then cooled to room temperature, DIPEA (2.29 g, 17.74 mmol) was added thereto, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 49-(4) (0.97 g, yield: 62%). The molecular weight of intermediate 49-(4) was about 1057 as measured by FAB MS.
[0736] Synthesis of compound 49
[0737] In an Ar atmosphere, intermediate 49-(4) (0.88 g, 0.83 mmol), 9H-carbazole (0.17 g, 1 mmol), Pd(dba) 2 (0.05 g, 0.08 mmol), P(tBu) 3 · HBF 4 (0.05 g, 0.17 mmol) and tBuONa (0.18 g, 1.91 mmol) were added to 4 mL of toluene, and the resulting mixture was heated at about 100 ° C and stirred for about 8 hours. After cooling to room temperature, water was added thereto, and the resulting mixture was filtered through celite, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to obtain compound 49 (0.81 g, yield: 82%). As measured by FAB MS, the molecular weight of compound 49 was about 1188.
[0738] By sublimation (360℃, 2.6×10 -3Pa) was further purified and used for the evaluation of light-emitting device characteristics.
[0739] (9) Synthesis of fused polycyclic compound 67
[0740]
[0741]
[0742]
[0743] Synthesis of intermediate 67-(1)
[0744] In an Ar atmosphere, intermediate 1-(1) (12.53 g, 31.01 mmol), N-(3-chlorophenyl)-[1,1'-biphenyl]-2-amine (9.54 g, 34.11 mmol), Pd(OAc)2 (0.21 g, 0.93 mmol), XantPhos (1.08 g, 1.86 mmol) and tBuONa (3.58 g, 37.21 mmol) were added to 55 mL of toluene, and the resulting mixture was heated at about 100 ° C and stirred for about 8 hours. After cooling to room temperature, water was added thereto, and the resulting mixture was filtered through celite, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 67-(1) (14.02 g, yield: 75%). The molecular weight of intermediate 67-(1) was about 603 as measured by FAB MS.
[0745] Synthesis of intermediate 67-(2)
[0746] A small amount of toluene (about 10 mL) was added to intermediate 1-(4) (2.26 g, 4.35 mmol), intermediate 67-(1) (13.11 g, 21.74 mmol), CuI (1.74 g, 9.13 mmol) and KCO (6.01 g, 43.49 mmol), and the resulting mixture was heated for about 24 hours while maintaining the ambient temperature at about 215° C. The mixture was then cooled and diluted with CHCl, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 67-(2) (3.22 g, yield: 71%). The molecular weight of intermediate 67-(2) was about 1042 as measured by FAB MS.
[0747] Synthesis of intermediate 67-(3)
[0748] In an Ar atmosphere, intermediate 67-(2) (3.02 g, 2.9 mmol) was dissolved in ODCB (29 mL), BBr 3 (1.45 g, 5.8 mmol) was added thereto, and the resulting mixture was heated at about 170° C. and stirred for about 10 hours. The mixture was then cooled to room temperature, DIPEA (4.49 g, 34.79 mmol) was added thereto, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 67-(3) (1.99 g, yield: 65%). The molecular weight of intermediate 67-(3) was about 1057 as measured by FAB MS.
[0749] Synthesis of compound 67
[0750] In an Ar atmosphere, intermediate 67-(3) (1.84 g, 1.74 mmol), 9H-carbazole (0.35 g, 2.09 mmol), Pd(dba)2 (0.10 g, 0.17 mmol), P(tBu)3·HBF4 (0.10 g, 0.35 mmol) and tBuONa (0.38 g, 4 mmol) were added to 8 mL of toluene, and the resulting mixture was heated at about 100°C and stirred for about 8 hours. After cooling to room temperature, water was added thereto, and the resulting mixture was filtered through celite, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to obtain compound 67 (1.53 g, yield: 74%). As measured by FAB MS, the molecular weight of compound 67 was about 1188.
[0751] By sublimation (360℃, 2.6×10 -3 Pa) was further purified and used for the evaluation of light-emitting device characteristics.
[0752] (10) Synthesis of fused polycyclic compound 93
[0753]
[0754]
[0755] Synthesis of intermediate 93-(1)
[0756] In an Ar atmosphere, 1,3-dibromo-5-fluorobenzene (4.11 g, 16.19 mmol) and [1,1'-biphenyl]-4-thiol (3.62 g, 19.42 mmol) and K2CO3 (10.07 g, 72.84 mmol) were added to 41 mL of NMP and the resulting mixture was heated for about 24 hours while maintaining the ambient temperature at about 140°C. The mixture was then cooled and diluted with CH2Cl2, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 93-(1) (6.26 g, yield: 92%). The molecular weight of intermediate 93-(1) was about 420 as measured by FAB MS.
[0757] Synthesis of intermediate 93-(2)
[0758] In an Ar atmosphere, intermediate 93-(1) (6.03 g, 14.35 mmol), N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine (5.07 g, 15.79 mmol), Pd(OAc)2 (0.1 g, 0.43 mmol), XantPhos (0.5 g, 0.86 mmol) and tBuONa (1.66 g, 17.22 mmol) were added to 71 mL of toluene, and the resulting mixture was heated at about 100° C. and stirred for about 8 hours. After cooling to room temperature, water was added thereto, and the resulting mixture was filtered through celite, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 93-(2) (6.83 g, yield: 72%). The molecular weight of intermediate 93-(2) was about 661 as measured by FAB MS.
[0759] Synthesis of intermediate 93-(3)
[0760] A small amount of toluene (about 10 mL) was added to intermediate 1-(4) (1.01 g, 1.94 mmol), intermediate 93-(2) (6.42 g, 9.72 mmol), CuI (0.78 g, 4.08 mmol) and KCO (2.69 g, 19.43 mmol), and the resulting mixture was heated for about 24 hours while maintaining the ambient temperature at about 215° C. The mixture was then cooled and diluted with CHCl, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 93-(3) (1.47 g, yield: 69%). The molecular weight of intermediate 93-(3) was about 1099 as measured by FAB MS.
[0761] Synthesis of compound 93
[0762] In an Ar atmosphere, intermediate 93-(3) (3.02 g, 2.75 mmol) was dissolved in ODCB (27 mL), BBr (1.38 g, 5.49 mmol) was added thereto, and the resulting mixture was heated at approximately 170° C. and stirred for approximately 10 hours. The mixture was then cooled to room temperature, DIPEA (4.25 g, 32.96 mmol) was added thereto, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to obtain compound 93 (2.21 g, yield: 72%). The molecular weight of compound 93 was approximately 1115 as measured by FAB MS.
[0763] By sublimation (370℃, 2.4×10 -3 Pa) was further purified and used for the evaluation of light-emitting device characteristics.
[0764] (11) Synthesis of fused polycyclic compound 131
[0765]
[0766]
[0767] Synthesis of intermediate 131-(1)
[0768] In an Ar atmosphere, 1-bromo-3-(tert-butyl)-5-fluorobenzene (2.51 g, 10.86 mmol), naphthalene-1-thiol (2.09 g, 13.03 mmol) and K CO (6.75 g, 48.87 mmol) were added to 25 mL of NMP and the resulting mixture was heated for about 24 hours while maintaining the ambient temperature at about 140° C. The mixture was then cooled and diluted with CH Cl, water was added thereto, and the resulting mixture was filtered through diatomaceous earth and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 131-(1) (3.51 g, yield: 87%). The molecular weight of intermediate 131-(1) was about 371 as measured by FAB MS.
[0769] Synthesis of intermediate 131-(2)
[0770] In an Ar atmosphere, intermediate 131-(1) (1.84 g, 4.96 mmol), [1,1':3',1"-terphenyl]-2'-amine (1.46 g, 5.95 mmol), Pd(dba)2 (0.28 g, 0.5 mmol), P(tBu)3·HBF4 (0.29 g, 0.99 mmol) and tBuONa (1.1 g, 11.4 mmol) were added to 24 mL of toluene, and the resulting mixture was heated at about 100°C and stirred for about 8 hours. After cooling to room temperature, water was added thereto, and the resulting mixture was filtered through celite, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 131-(2) (2.28 g, yield: 86%). The molecular weight of intermediate 131-(2) was about 536 as measured by FAB MS.
[0771] Synthesis of intermediate 131-(3)
[0772] A small amount of toluene (about 10 mL) was added to intermediate 131-(2) (1.01 g, 1.89 mmol), intermediate 93-(2) (6.23 g, 9.43 mmol), CuI (0.75 g, 3.96 mmol) and KCO (2.61 g, 18.85 mmol), and the resulting mixture was heated for about 24 hours while maintaining the ambient temperature at about 215° C. The mixture was then cooled and diluted with CHCl, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to provide intermediate 131-(3) (1.30 g, yield: 62%). The molecular weight of intermediate 131-(3) was about 1116 as measured by FAB MS.
[0773] Synthesis of compound 131
[0774] In an Ar atmosphere, intermediate 131-(3) (1.24 g, 1.11 mmol) was dissolved in ODCB (11 mL), BBr (0.56 g, 2.22 mmol) was added thereto, and the resulting mixture was heated at about 170 ° C and stirred for about 10 hours. Then, the mixture was cooled to room temperature, DIPEA (1.72 g, 13.34 mmol) was added thereto, water was added thereto, and the resulting mixture was filtered through diatomaceous earth, and liquid separation was performed to concentrate the organic layer. The organic layer was purified by silica gel column chromatography to obtain compound 131 (0.85 g, yield: 68%). As measured by FAB MS, the molecular weight of compound 131 was about 1131.
[0775] By sublimation (380℃, 2.5×10-3 Pa) was further purified and used for the evaluation of light-emitting device characteristics.
[0776] 1. Manufacturing and evaluation of light-emitting components
[0777] The light-emitting elements of the embodiments comprising the fused polycyclic compounds of the embodiments in the emission layer were manufactured as follows. Compound 1, Compound 3, Compound 4, Compound 9, Compound 13, Compound 23, Compound 33, Compound 49, Compound 67, Compound 93, and Compound 131, which are fused polycyclic compounds of the above-mentioned embodiment compounds, were used as dopant materials for the emission layer to manufacture the light-emitting elements of Examples 1 to 11, respectively. Comparative Examples 1 to 9 correspond to light-emitting elements manufactured by using Comparative Example Compounds X1 to X9, respectively, as dopant materials for the emission layer.
[0778] Example compounds
[0779]
[0780] Comparative Example Compounds
[0781]
[0782] Manufacturing of light-emitting components
[0783] ITO was used to form a 150 nm thick first electrode, dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) was used to form a 10 nm thick hole injection layer on the first electrode, N,N'-bis(naphthalene-1-yl)-N,N'-bis(phenyl)-2,2'-dimethylbenzidine (α-NPD) was used to form an 80 nm thick hole transport layer on the hole injection layer, and 1,3-bis(N-carbazolyl)benzene (mCP) was used to form a 5 nm thick emission auxiliary layer on the hole transport layer. Based on the Example compounds or Comparative Example compounds and 3,3 1 wt% of the Example compound or the Comparative Example compound was doped into 3,3'-bis(9H-carbazol-9-yl)-1,1'-biphenyl (mCBP) to form a 20 nm thick emission layer on the emission-assisting layer, 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi) was used to form a 30 nm thick electron transport layer on the emission layer, LiF was used to form a 0.5 nm thick electron injection layer on the electron transport layer, and Al was used to form a 100 nm thick second electrode on the electron injection layer. Each layer was formed by a deposition method in a vacuum atmosphere.
[0784] The compounds used to manufacture the light-emitting elements of Examples and Comparative Examples are disclosed herein. These compounds are suitable materials, and commercial products were purified by sublimation and used to manufacture the devices.
[0785]
[0786] Evaluation of light-emitting element characteristics
[0787] The evaluation results of each of the light-emitting elements in Examples 1 to 11 and Comparative Examples 1 to 9 are listed in Table 1. The maximum emission wavelength (λ max ), attenuation values (%) and relative service life (LT50) are listed in Table 1 for comparison.
[0788] The maximum emission wavelength (λ) in the characteristic evaluation results of each of the Examples and Comparative Examples shown in Table 1 was measured using an external quantum efficiency measurement device (C9920-12 manufactured by Hamamatsu Photonics Co., Ltd., Japan). max ), attenuation value (%) and relative service life (LT50). Maximum emission wavelength (λ max ) represents the wavelength showing the maximum value of the emission intensity in the emission spectrum. The attenuation value represents the ratio of luminous efficiency reduction at high brightness and is based on 1 cd / m 2 Brightness and 1000cd / m 2 In addition, by 800cd / m 2 The relative service life (LT50) is represented by the time it takes for the brightness to be reduced to half at the initial brightness of 1.0. The relative service life (LT50) is shown relative to the result of Comparative Example 3 set to 1.0.
[0789] Table 1
[0790]
[0791]
[0792] With reference to the results of Table 1, it can be confirmed that the examples of the light-emitting elements (in each example, the fused polycyclic compound according to the embodiment of the present disclosure is used as a light-emitting material) each have an attenuation value low compared to the attenuation value of the comparative example, and therefore prevent or reduce the reduction in luminous efficiency even at high brightness, and improve the element service life characteristics. The fused polycyclic compound of one or more embodiments includes a core comprising the above-mentioned first fused ring structure and the second fused ring structure, thereby achieving high luminous efficiency and long element service life. In particular, by including a first fused ring structure comprising a boron atom, a nitrogen atom and a heteroatom, rather than a structure in which the boron atom and two oxygen atoms of the fused polycyclic compound contained in the emission layer of a conventional organic electroluminescent element are simultaneously (for example, synchronously) fused, the spatial characteristics of the fused polycyclic compound are increased, thereby reducing the intermolecular interaction between the molecules of the fused polycyclic compound, which has the effect of improving the stability of the fused polycyclic compound. In addition, in the fused polycyclic compound of one or more embodiments, due to steric hindrance, the biphenyl group and / or terphenyl group substituted at the nitrogen atom is located on a different plane from the first fused ring structure and the second fused ring structure, and thus has the effect of further enhancing the spatial characteristics of the fused polycyclic compound. In addition, the first fused ring structure or the second fused ring structure may include at least one of a naphthyl group, a phenanthrenyl group, and a pyrenyl group to reduce the lowest triplet excitation energy level (T1) of the fused polycyclic compound, and thus the fused polycyclic compound can exhibit high thermal stability and chemical stability.
[0793] In other words, the fused polycyclic compound described in the present disclosure includes a core with two fused ring structures, which enhances luminous efficiency and component service life. By incorporating a boron atom, a nitrogen atom and a heteroatom into the first fused ring structure, due to increasing spatial characteristics, reducing molecular interactions, and improving the stability of the fused polycyclic compound. In addition, the biphenyl or terphenyl attached to the nitrogen atom is located on a different plane from the first fused ring structure and the second fused ring structure, further enhancing spatial characteristics. Including naphthyl, phenanthrenyl and / or pyrenyl in the ring structure reduces the lowest triplet excitation energy level, produces high thermal stability and chemical stability. When Examples 1 to 11 are compared with Comparative Examples 1 to 9, the long component service life of the light-emitting component has been achieved in each embodiment, and even at high brightness, luminous efficiency degradation is prevented or reduced. For example, the relative service life (LT50) of Examples 1 to 11 improves by 3.1 times to 23.5 times. The example compounds included in Examples 1 to 11 may each include a core including the first condensed ring structure and the second condensed ring structure as described above, thereby achieving high luminous efficiency and long device life.
[0794] Compared to the Example, Comparative Examples 1, 2, and 4 each had degraded attenuation characteristics and device lifespan. Compared to the Example compounds, Comparative Example Compounds X1, X2, and X4, respectively included in Comparative Examples 1, 2, and 4, may have degraded material stability due to the inclusion of only one boron atom. Accordingly, compared to the light-emitting elements of the Example, the light-emitting elements of Comparative Examples 1, 2, and 4 may have reduced device lifespan and degraded attenuation characteristics.
[0795] Comparative Example Compound X3 and Comparative Example Compound X5, respectively included in Comparative Example 3 and Comparative Example 5, each include a structure in which two fused ring structures are connected, but differ from the Example compounds in that the two fused rings are connected to each other and do not include a structure of a fused ring structure containing a boron atom, a nitrogen atom, and a heteroatom (O or S), and therefore may have low planarity and degraded stability. Accordingly, compared to the light-emitting element of the embodiment, the element service life of each of the light-emitting elements of Comparative Example 3 and Comparative Example 5 may be reduced, and the attenuation characteristics may be degraded.
[0796] Like the Example compounds, the Comparative Example Compound X6 included in Comparative Example 6 includes a structure in which two fused ring structures are connected, but does not include a fused ring structure containing one boron atom, one nitrogen atom, and one heteroatom (O or S), and therefore may have low planarity and degraded stability. Accordingly, compared to the light-emitting element of the Example, the element service life of the light-emitting element of Comparative Example 6 may be reduced, and the attenuation characteristics may be degraded.
[0797] As with the embodiment compounds, the comparative example compound X7 included in comparative example 7 includes a fused ring structure, wherein two fused ring structures are linked together, and include a boron atom, a nitrogen atom, and a heteroatom (O or S), but does not include at least one of a naphthyl group, a phenanthrenyl group, and a pyrenyl group, and therefore the lowest triplet excitation energy level (T1) of the fused polycyclic compound may not be reduced, and does not include a biphenyl group or a terphenyl group, and therefore the planarity of the molecule is high, making the intermolecular interaction relatively strong than that of the embodiment compounds, and therefore material stability may be degraded. Accordingly, compared with the light-emitting element of the embodiment, the element service life of the light-emitting element of comparative example 7 may be reduced, and attenuation characteristics may be degraded.
[0798] As with embodiment compounds, the comparative example compound X8 included in comparative example 8 includes a structure in which two fused ring structures are connected, but includes a fused ring structure containing a boron atom and two oxygen atoms so that it can be easily decomposed in a post-synthesis purification process. In addition, comparative example compound X8 does not include biphenyl or terphenyl, and therefore has a high molecular planarity, and the intermolecular interaction is relatively strong than the intermolecular interaction of embodiment compounds. Therefore, the stability of the material can be degraded. Accordingly, compared with the light-emitting component of embodiment, the element service life of the light-emitting component of comparative example 8 can be reduced, and attenuation characteristics can be degraded.
[0799] As with embodiment compounds, the comparative example compound X9 included in comparative example 9 includes a structure in which two fused ring structures are connected, but includes a fused ring structure containing a boron atom and two oxygen atoms so that it can be easily decomposed in a post-synthesis purification process. In addition, the fused ring structure containing a boron atom and two oxygen atoms has a higher planarity than the fused ring structure containing a boron atom, a nitrogen atom and a heteroatom (O or S), so intermolecular interaction is strong, so as to degrade stability. Accordingly, compared with the light-emitting component of embodiment, the element service life of the light-emitting component of comparative example 9 can be reduced, and attenuation characteristics can be degraded.
[0800] By including the fused polycyclic compound of one or more embodiments, the light-emitting element of one or more embodiments of the present disclosure can exhibit improved element characteristics with high luminous efficiency and long element life.
[0801] The fused polycyclic compound of one or more embodiments may be included in an emission layer of a light-emitting element to contribute to high luminous efficiency and long element life of the light-emitting element.
[0802] By including the light-emitting element of one or more embodiments, the display device / apparatus of one or more embodiments can exhibit excellent or appropriate display quality.
[0803] As utilized herein, the terms "substantially," "about," or similar terms are used as terms of approximation and not as terms of degree, and are intended to take into account the inherent deviations in measurements or calculations that one of ordinary skill in the art would recognize. As used herein, "about" is inclusive of the recited value and means within an acceptable range of deviation determined for the particular value by one of ordinary skill in the art taking into account the measurements in question and the errors associated with the measurement of the particular quantity (i.e., limitations of the measurement system). For example, "about" can mean within one or more standard deviations of the recited value, or within ±30%, ±20%, ±10%, or ±5% of the recited value.
[0804] In the context of this application and unless otherwise defined, the terms "use," "using," and "used" may be considered synonymous with the terms "utilize," "utilizing," and "utilized," respectively.
[0805] Any numerical range set forth in this article is intended to include all subranges of the same numerical precision that fall within the range set forth. For example, the range of "1.0 to 10.0" is intended to include between the minimum value of 1.0 set forth and the maximum value of 10.0 set forth (and including 1.0 and 10.0), that is, all subranges with a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limit set forth in this article is intended to include all lower numerical limits that fall therein and any minimum numerical limit set forth in this specification is intended to include all higher numerical limits that fall therein. Accordingly, the applicant reserves the right to amend this disclosure, including the claims, to explicitly set forth any subrange that falls within the range explicitly set forth herein.
[0806] The light-emitting elements, display devices / devices, electronic devices, devices for manufacturing the same, or any other related devices / devices or components according to the embodiments of the present disclosure described herein may be implemented using any appropriate hardware, firmware (e.g., application specific integrated circuits), software, or a combination of software, firmware, and hardware. For example, the various components of the device may be formed on an integrated circuit (IC) chip or on separate IC chips. Further, the various components of the device may be implemented on a flexible printed circuit film, a tape carrier package (TCP), or a printed circuit board (PCB), or formed on a substrate. Further, the various components of the device may be processes or threads that run on one or more processors in one or more computing devices, execute computer program instructions, and interact with other system components for performing the various functions described herein. The computer program instructions are stored in a memory that can be implemented in a computing device using a standard storage device such as, for example, a random access memory (RAM). The computer program instructions may also be stored in other non-temporary computer-readable media such as, for example, a CD-ROM or a flash drive. Furthermore, those skilled in the art will recognize that the functionality of various computing devices may be combined or integrated into a single computing device, or the functionality of a particular computing device may be distributed across one or more other computing devices without departing from the scope of the embodiments of the present disclosure.
[0807] In the present disclosure, each appropriate feature of the various embodiments of the present disclosure may be partially or completely combined together or combined with each other, and may be technically interlocked and operated in various appropriate ways, and unless otherwise stated or implied, each embodiment may be implemented independently of each other or in combination with each other in any appropriate manner.
[0808] Although the present disclosure has been described with reference to example embodiments thereof, it will be understood that the present disclosure should not be limited to these embodiments, but one or more appropriate changes and modifications may be made by those skilled in the art without departing from the spirit and scope of the present disclosure.
[0809] Accordingly, the technical scope of the present disclosure is not intended to be limited to the contents set forth in the detailed description of the present disclosure, but is intended to be defined by the claims and their equivalents.
Claims
1. A fused polycyclic compound represented by Formula 1: Formula 1 in, In formula 1, q, w and e are each independently an integer selected from 0 to 3, r is an integer selected from 0 to 2, q21, w31, e41 and r51 are each independently an integer selected from 0 to 4, The sum of q, w, e and r is 1 or greater, When q is 0, q2 is an integer selected from 0 to 4, when q is 1, q2 is an integer selected from 0 to 2, and when q is 2 or 3, q2 is 0, When w is 0, w2 is an integer selected from 0 to 4, when w is 1, w2 is an integer selected from 0 to 2, and when w is 2 or 3, w2 is 0, When e is 0, e2 is an integer selected from 0 to 4, when e is 1, e2 is an integer selected from 0 to 2, and when e is 2 or 3, e2 is 0, When r is 0, r2 is an integer selected from 0 to 3, when r is 1, r2 is 0 or 1, and when r is 2, r2 is 0, X1 is O or S, X2 is O, S or NT 20 , X3 is O, S or NT 30 , T1 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, T 20 、T 30 T2, T3, T4, T5 and T6 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, and T 21 、T 31 、T 41 and T 51 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms and / or bonds to an adjacent group to form a ring.
2. The fused polycyclic compound according to claim 1, wherein the fused polycyclic compound represented by Formula 1 is represented by Formula 1-1: Formula 1-1 In formula 1-1, A is hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, a is an integer selected from 0 to 9, and q, w, e, r, q21, w31, e41, r51, q2, w2, e2, r2, X1, X2, X3, T 20 、T 30 、T2、T3、T4、T5、T6、T 21 、T 31 、T 41 and T 51 are each independently the same as defined in Formula 1.
3. The fused polycyclic compound according to claim 1, wherein the fused polycyclic compound represented by Formula 1 is represented by Formula 2-1 or Formula 2-2: Formula 2-1 Formula 2-2 In formula 2-1 and formula 2-2, q, w, e, r, q21, w31, e41, r51, q2, w2, e2, r2, T1, T 20 、T 30 、T2、T3、T4、T5、T6、T 21 、T 31 、T 41 and T 51 are each independently the same as defined in Formula 1.
4. The fused polycyclic compound according to claim 1, wherein the fused polycyclic compound represented by Formula 1 is represented by any one selected from Formula 3-1 to Formula 3-7: Formula 3-1 Formula 3-2 Formula 3-3 Formula 3-4 Formula 3-5 Formula 3-6 Formula 3-7 In formula 3-1 to formula 3-7, T 201 、T 202 、T 203 、T 204 、T 205 、T 206 and T 207 each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, and / or is bonded to an adjacent group to form a ring, q201, q202 and q203 are each independently an integer selected from 0 to 6, q204, q205, q206 and q207 are each independently an integer selected from 0 to 8, and w, e, r, w31, e41, r51, w2, e2, r2, X1, X2, X3, T1, T 20 、T 30 、T3、T4、T5、T6、T 31 、T 41 and T 51 are each independently the same as defined in Formula 1.
5. A light-emitting element, comprising: a first electrode; a second electrode opposite to the first electrode; as well as an emitting layer between the first electrode and the second electrode, wherein the emission layer comprises the fused polycyclic compound according to any one of claims 1 to 4 as a first compound. The light-emitting element according to claim 5 , wherein in Formula 1, T 1 is a substituted or unsubstituted biphenyl group. 7 . The light-emitting element according to claim 6 , wherein in Formula 1, T1 is an unsubstituted biphenyl group, and the unsubstituted biphenyl group is connected to the N atom via the 2-carbon atom thereof.
8. The light-emitting element according to claim 5, wherein in Formula 1, T 20 and T 30 Each of is a substituted or unsubstituted terphenyl group.
9. The light-emitting element according to claim 8, wherein in Formula 1, T 20 and T 30 Each of the groups is an unsubstituted m-terphenyl group.
10. The light-emitting element according to claim 5, wherein the condensed polycyclic compound represented by Formula 1 as the first compound is represented by any one selected from Formula 4-1 to Formula 4-7: Formula 4-1 Formula 4-2 Formula 4-3 Formula 4-4 Formula 4-5 Formula 4-6 Formula 4-7 In formulas 4-1 to 4-7, T 301 、T 302 、T 303 、T 304 、T 305 、T 306 and T 307 each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, and / or is bonded to an adjacent group to form a ring, w301, w302 and w303 are each independently an integer selected from 0 to 6, w304, w305, w306 and w307 are each independently an integer selected from 0 to 8, and q, e, r, q21, e41, r51, q2, e2, r2, X1, X2, X3, T1, T 20 、T 30 、T2、T4、T5、T6、T 21 、T 41 and T 51 are each independently the same as defined in Formula 1.
11. The light-emitting element according to claim 5, wherein the fused polycyclic compound represented by Formula 1 as the first compound is represented by any one selected from Formula 5-1 to Formula 5-7: Formula 5-1 Formula 5-2 Formula 5-3 Formula 5-4 Formula 5-5 Formula 5-6 Formula 5-7 In formulas 5-1 to 5-7, T 401 、T 402 、T 403 、T 404 、T 405 、T 406 and T 407 each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, and / or is bonded to an adjacent group to form a ring, e401, e402 and e403 are each independently an integer selected from 0 to 6, e404, e405, e406 and e407 are each independently an integer selected from 0 to 8, and q, w, r, q21, w31, r51, q2, w2, r2, X1, X2, X3, T1, T 20 、T 30 、T2、T3、T5、T6、T 21 、T 31 and T 51 are each independently the same as defined in Formula 1.
12. The light-emitting element according to claim 5, wherein the fused polycyclic compound represented by Formula 1 as the first compound is represented by any one selected from Formula 6-1 to Formula 6-3: Formula 6-1 Formula 6-2 Formula 6-3 In equations 6-1 to 6-3, T 501 to T 503 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, r501 and r502 are each independently an integer selected from 0 to 5, r503 is an integer selected from 0 to 3, and q, w, e, q21, w31, e41, q2, w2, e2, X1, X2, X3, T1, T 20 、T 30 、T2、T3、T4、T6、T 21 、T 31 and T 41 are each independently the same as defined in Formula 1.
13. The light-emitting element according to claim 5, wherein the emission layer further comprises at least one of a second compound represented by Formula HT-1, a third compound represented by Formula ET-1, and a fourth compound represented by Formula D-1: Formula HT-1 in, In formula HT-1, M1 to M8 are each independently N or CR 51 , L1 is a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, Y a For direct connection, CR 52 R 53 or SiR 54 R 55 , Ar a is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and R 51 to R 55 Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted thiol, substituted or unsubstituted oxy, substituted or unsubstituted amino, substituted or unsubstituted boron, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 60 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 60 ring carbon atoms, and / or bonds with an adjacent group to form a ring; Formula ET-1 Wherein, in formula ET-1, Selected from Z a to Z c At least one of them is N, and the rest are CR 56 , R 56 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, b1 to b3 are each independently an integer selected from 0 to 10, Ar b to Ar d are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and L2 to L4 are each independently a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms; and Formula D-1 Wherein, in formula D-1, Q1 to Q4 are each independently C or N, C1 to C4 are each independently a substituted or unsubstituted hydrocarbon ring group having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 ring carbon atoms, X 11 To X 14 Each independently is directly connected or *-O-*, L 11 To L 13 Each is independently connected to direct connection, *-O-*, *-S-*, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, -* denotes a moiety connected to C1 to C4, b11 to b13 are each independently 0 or 1, R 61 to R 66 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted thiol, substituted or unsubstituted oxy, substituted or unsubstituted amino, substituted or unsubstituted boron, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 60 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 60 ring carbon atoms, and / or selected from R 61 to R 66 One or more of the groups independently bond to adjacent groups to form a ring, and d1 to d4 are each independently an integer selected from 0 to 4.
14. The light-emitting element according to claim 5, wherein the first compound is any one selected from the compounds listed in Compound Group 1: Compound Group 1 15. A display device comprising: basal layer; a circuit layer on the base layer; as well as A display element layer is on the circuit layer and includes the light emitting element according to any one of claims 5 to 14.
16. The display device according to claim 15, wherein the light emitting element further comprises a capping layer on the second electrode, and The capping layer has a refractive index of 1.6 or greater with respect to light in a wavelength range of 550 nm to 660 nm.
17. The display device according to claim 15, further comprising a light control layer on the display element layer and comprising quantum dots, wherein the light emitting element emits light of a first color, and The light control layer comprises: a first light control component including a first quantum dot configured to convert the first color light into a second color light having a longer wavelength than the first color light; a second light control member including second quantum dots configured to convert the first color light into a third color light having a longer wavelength region than a wavelength region of each of the first color light and the second color light; as well as The third light control component is configured to transmit the first color light.
18. The display device according to claim 17, further comprising a color filter layer on the light control layer, The color filter layer comprises: a first color filter configured to transmit light of the second color; a second color filter configured to transmit the third color light; as well as A third color filter is configured to transmit the first color light.
19. An electronic device comprising the display device according to any one of claims 15 to 18.
20. The electronic device according to claim 19, comprising at least one of a television, a monitor, an outdoor billboard, a personal computer, a laptop computer, a personal digital terminal, a display device for a vehicle, a game console, a portable electronic device, and a camera.
Citation Information
Patent Citations
Rug for preventing noise transmission
KR1020240030963A