Fused ring compound and organic light-emitting device including same
A novel fused ring compound enhances hole transport and injection in organic light-emitting devices, enabling low voltage operation, high brightness, and extended lifespan.
Patent Information
- Application Number
- JP2018116725
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2017-06-20
- Filing Date
- 2018-06-20
- Publication Date
- 2025-01-09
- Estimated Expiration
- 2038-06-20
AI Technical Summary
Existing organic light-emitting devices face challenges in achieving low voltage operation, high brightness, and long lifespan, with a need for novel materials that enhance hole transport and injection capabilities.
The introduction of a fused ring compound represented by a specific chemical formula, which can be incorporated into the organic layer of the device, including a hole transport region and light-emitting layer, to improve hole transport and injection abilities.
The fused ring compound enables the device to operate at low voltage, emit light with high brightness, and maintain high efficiency and longevity.
Smart Images

Figure 0007610915000258 
Figure 0007610915000259 
Figure 0007610915000260
Abstract
Description
[Technical field]
[0001] The present invention relates to a fused ring compound and an organic light-emitting device including the same. [Background technology]
[0002] An organic light-emitting device is a self-emitting device that has a wider viewing angle, better contrast, and a shorter response time than conventional devices, and is excellent in terms of luminance, driving voltage, and response speed.
[0003] An organic light emitting device may have a structure in which a first electrode is disposed on a substrate, and a hole-transport region, a light emitting layer, an electron-transport region, and a second electrode are sequentially formed on the first electrode. Holes injected from the first electrode move to the light emitting layer via the hole transport region, and electrons injected from the second electrode move to the light emitting layer via the electron transport region. The hole and electron carriers recombine in the light emitting layer to generate excitons. Light is generated as the excitons relax from the excited state to the ground state. [Prior art documents] [Patent documents]
[0004] [Patent Document 1] US Patent Application Publication No. 2002 / 0028346 Summary of the Invention [Problem to be solved by the invention]
[0005] One of the problems to be solved by the present invention is to provide a novel fused ring compound and an organic light-emitting device containing the same. [Means for solving the problem]
[0006] According to one aspect of the present invention, there is provided a fused ring compound represented by the following formula 1: [ka] In chemical formula 1, X 1 is O, S, Se, C(R 4 )(R 5 ), Si(R 4 )(R 5 ) and B(R 4 ), Ring A 1 , A 2 and A 3 are independent of each other, C 5 -C 60 Carbocyclic groups, and C 2 -C 30 heterocyclic groups, L 1 From L 9 are each independently a substituted or unsubstituted C 3 -C 10 Cycloalkylene groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene groups, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene groups, substituted or unsubstituted C 1 -C 60 is selected from a heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, and a substituted or unsubstituted divalent non-aromatic fused polycyclic heterocyclic group; a1 to a9 are independently selected from integers from 0 to 5; Ar 1 From Ar 6 are each independently a substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 1 -C 60 is selected from a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused polycyclic heterocyclic group; b1 to b6 are independently selected from integers from 1 to 5; R 1 From R 5 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl groups, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 1 -C 60Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic groups, -Si(Q 1 )(Q 2 )(Q 3 ), -N(Q 1 )(Q 2 ), -B(Q 1 )(Q 2 ), -C(=O)(Q 1 ), -S(=O) 2 (Q 1 ), and -P(=O)(Q 1 )(Q 2 ), c1 to c3 are independently selected from integers from 0 to 5; n1 to n3 are each independently 0 or 1, but n1+n2+n3 is 1; Replaced C 3 -C 10 Cycloalkylene groups, substituted C 1 -C 10 Heterocycloalkylene groups, substituted C 3 -C 10 Cycloalkenylene groups, substituted C 1 -C 10 Heterocycloalkenylene groups, substituted C 6 -C 60 Arylene Groups, Substituted C 1 -C 60 Heteroarylene groups, substituted divalent nonaromatic condensed polycyclic groups, substituted divalent nonaromatic condensed heteropolycyclic groups, substituted C 1 -C 60 Alkyl groups, substituted C 2 -C 60 Alkenyl groups, substituted C 2 -C 60 Alkynyl groups, substituted C 1 -C 60 Alkoxy groups, substituted C 3 -C 10 Cycloalkyl groups, substituted C 1 -C 10 Heterocycloalkyl groups, substituted C 3 -C 10 Cycloalkenyl groups, substituted C1 -C 10 Heterocycloalkenyl Groups, Substituted C 6 -C 60 Aryl groups, substituted C 6 -C 60 Aryloxy groups, substituted C 6 -C 60 Arylthio groups, substituted C 1 -C 60 At least one of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituent of the substituted monovalent non-aromatic fused polycyclic heterocyclic group is Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups and C 1 -C 60 Alkoxy groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12), -C(=O)(Q 11 ), -S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) substituted with at least one selected from 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups and C 1 -C 60 Alkoxy groups; C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups and terphenyl groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 ) substituted with at least one selected from 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups; and -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32); Q 1 From Q 3 , Q 11 From Q 13 , Q 21 From Q 23 , and Q 31 From Q 33 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 Alkyl-substituted C 6 -C 60 Aryl group, C 6 -C 60 Aryl-substituted C 6 -C 60 Aryl Group C 1 -C 60 Heteroaryl groups, C 1 -C 60 Alkyl-substituted C 1 -C 60 Heteroaryl groups, C 6 -C 60 Aryl-substituted C 1 -C 60 It is selected from a heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic hetero-fused polycyclic group, a biphenyl group, and a terphenyl group.
[0007] According to another aspect of the present invention, there is provided an organic light-emitting device comprising a first electrode, a second electrode opposed to the first electrode, and an organic layer interposed between the first electrode and the second electrode and including a light-emitting layer, wherein the organic layer contains one or more of the above-mentioned fused ring compounds. Effect of the Invention
[0008] The organic light emitting device including the fused ring compound according to the present invention can be driven at a low voltage, emit light with high luminance, and have high efficiency and a long life. [Brief description of the drawings]
[0009] [Figure 1] 1 is a schematic diagram illustrating a structure of an organic light emitting device according to an embodiment. [Diagram 2] 1 is a schematic diagram illustrating a structure of an organic light emitting device according to an embodiment. [Diagram 3] 1 is a schematic diagram illustrating a structure of an organic light emitting device according to an embodiment. [Figure 4] 1 is a schematic diagram illustrating a structure of an organic light emitting device according to an embodiment. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0010] The fused ring compound of the present invention is represented by the following chemical formula 1: [ka]
[0011] In formula 1, X 1 is O, S, Se, C(R 4 )(R 5 ), Si(R 4 )(R 5 ) and B(R 4 ), where R 4 and R 5 The explanation regarding this will be given later.
[0012] For example, in formula 1, X 1 is O,C(R 4 )(R5 ), Si(R 4 )(R 5 ) and B(R 4 ), but is not limited thereto. In formula 1, ring A 1 , ring A 2 and Ring A 3 Each is fused to an adjacent seven-membered ring by sharing a carbon. 1 , A 2 and A 3 are independent of each other, C 5 -C 60 Carbocyclic groups and C 2 -C 30 heterocyclic groups.
[0013] For example, in formula 1, ring A 1 , A 2 and A 3 are each independently selected from a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, a chrysene ring, a triphenylene ring, an indene ring, a fluorene ring, a benzofluorene ring, a spiro-bifluorene ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a pyrrole ring, an imidazole ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a quinazoline ring, a triazine ring, an indenopyrazine ring, an indenopyridine ring, a phenanthroline ring and a phenanthridine ring.
[0014] According to one embodiment, in Formula 1, ring A 1 , A 2 and A 3 are each independently selected from a benzene ring, a naphthalene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring and a quinazoline ring.
[0015] According to another embodiment, in Formula 1, ring A 1 , A 2 and A 3are each independently a benzene ring or a naphthalene ring, but are not limited thereto.
[0016] In formula 1, L 1 From L 9 are each independently a substituted or unsubstituted C 3 -C 10 Cycloalkylene groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene groups, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene groups, substituted or unsubstituted C 1 -C 60 It is selected from a heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, and a substituted or unsubstituted divalent non-aromatic fused polycyclic heterocyclic group.
[0017] For example, in formula 1, L 1 From L 9are each independently a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a spiro-benzofluorene-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a pyrrolylene group, a thiophenylene group, a furanylene group, a silolylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an indolylene group, an isoindolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, a benzofuranylene group, a benzothiophenylene group, a benzosilolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzo thiophenylene groups, dibenzosilolylene groups, carbazolylene groups, benzocarbazolylene groups, dibenzocarbazolylene groups, thiadiazolylene groups, imidazopyridinylene groups, imidazopyrimidinylene groups, oxazolopyridinylene groups, thiazolopyridinylene groups, benzonaphthyridinylene groups, azafluorenylene groups, azaspiro-bifluorenylene groups, azacarbazolylene groups, azadibenzofuranylene groups, azadibenzothiophenylene groups and azadibenzosilolylene groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, C 3 -C10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups, terphenyl groups and -Si(Q 31 )(Q 32 )(Q 33), each of which is substituted with at least one selected from the group consisting of a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a spiro-benzofluorene-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, and a chrysenylene group. a perylenylene group, a pentaphenylene group, a pyrrolylene group, a thiophenylene group, a furanylene group, a silolylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an indolylene group, an isoindolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthylene group, Lysinylene group, quinoxalinylene group, quinazolinylene group, cinnolinylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzimidazolylene group, benzofuranylene group, benzothiophenylene group, benzosilolylene group, isobenzothiazolylene group, benzoxazolylene group, isobenzoxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzo a thiophenylene group, a dibenzosilolylene group, a carbazolylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a thiadiazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, an oxazolopyridinylene group, a thiazolopyridinylene group, a benzonaphthyridinylene group, an azafluorenylene group, an azaspiro-bifluorenylene group, an azacarbazolylene group, an azadibenzofuranylene group, an azadibenzothiophenylene group, and an azadibenzosilolylene group; Q 31 From Q 33 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, pyridinyl groups, pyrimidinyl groups, pyrazinyl groups, quinolinyl groups, isoquinolinyl groups, quinoxalinyl groups, and quinazolinyl groups; and C 1 -C 10 Alkyl group, C 1 -C 10 and selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, and a quinazolinyl group, each of which is substituted with at least one selected from an alkoxy group and a phenyl group.
[0018] As yet another example, in Formula 1, L 1 From L 9 are each independently selected from the group represented by one of the following chemical formulas 3-1 to 3-102: [ka] [ka] [ka] [ka] [ka] [ka]
[0019] In chemical formulas 3-1 to 3-102, Y 1 is O, S, C(Z 3 )(Z 4 ), N(Z 5 ) or Si(Z 6 )(Z 7 ) and Z 1 From Z 7are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 alkoxy groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclopentenyl groups, cyclohexenyl groups, phenyl groups, biphenyl groups, terphenyl groups, pentalenyl groups, indenyl groups, naphthyl groups, azulenyl groups, heptalenyl groups, indacenyl groups, acenaphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenalenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, Triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, isoindolyl group group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, adiazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilolyl group, -Si(Q 31 )(Q 32 )(Q33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ), Q 31 From Q 33 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10 alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, pyridinyl groups, pyrimidinyl groups, pyrazinyl groups, quinolinyl groups, isoquinolinyl groups, quinoxalinyl groups, and quinazolinyl groups; and C 1 -C 10 Alkyl group, C 1 -C 10 a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, and a quinazolinyl group, each of which is substituted with at least one selected from an alkoxy group and a phenyl group; d2 is selected from the integers 0 to 2; d3 is selected from the integers 0 to 3; d4 is selected from the integers 0 to 4; d5 is selected from the integers 0 to 5; d6 is selected from the integers 0 to 6; d8 is selected from the integers 0 to 8; * and *' are bonding sites with adjacent atoms.
[0020] According to one embodiment, in Formula 1, L 1 From L 9 are each independently selected from the groups represented by the above chemical formulas 3-1 to 3-24; In chemical formulas 3-1 to 3-24, Z 1 From Z 7are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Also selected from, but not limited to, alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenanthrenyl groups, anthracenyl groups, pyrenyl groups, chrysenyl groups, carbazolyl groups, dibenzofuranyl groups and dibenzothiophenyl groups.
[0021] According to another embodiment, in Formula 1, L 1 From L 9 are independently selected from the groups represented by the following chemical formulas 4-1 to 4-57: [ka] [ka] [ka] [ka] [ka]
[0022] In chemical formulas 4-1 to 4-57, Ph is a phenyl group, and * and *' are bonding sites with adjacent atoms.
[0023] According to yet another embodiment, in Formula 1, L 1 From L 9 are each independently selected from the groups represented by formulas 4-1 to 4-35, but are not limited thereto.
[0024] In Chemical Formula 1, a1 to a9 are each independently selected from integers of 0 to 5. a1 is L 1 If a1 is 0, then *-(L 1 ) a1 -*' is a single bond, and when a1 is 2 or more, two or more L 1 may be the same or different. The explanation of a2 to a9 can be understood with reference to the explanation of a1 and the structure of Chemical Formula 1.
[0025] According to one embodiment, in Chemical Formula 1, a1 to a9 are, independently of one another, 0, 1 or 2. According to another embodiment, in Chemical Formula 1, a1 to a9 are, independently of one another, 0 or 1.
[0026] In formula 1, Ar 1 From Ar 6 are each independently a substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 1 -C 60 It is selected from a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused polycyclic heterocyclic group.
[0027] For example, in formula 1, Ar 1 From Ar 6are each independently a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a spiro-benzofluorene-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, Chrysenyl group, perylenyl group, pentaphenyl group, pyrrolyl group, thiophenyl group, furanyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, isoindolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyl group, A thiridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzo azothiophenyl, dibenzosilolyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, oxazolopyridinyl, thiazolopyridinyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl and azadibenzosilolyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group, terphenyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32), each of which is substituted with at least one selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a spiro-benzofluorene-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, and a triphenylenyl group. group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, pyrrolyl group, thiophenyl group, furanyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, isoindolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzo azathiophenyl group, dibenzosilolyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, oxazolopyridinyl group, thiazolopyridinyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group and azadibenzosilolyl group; Q 1 From Q 3 , and Q 31 From Q 33 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, pyridinyl groups, pyrimidinyl groups, pyrazinyl groups, quinolinyl groups, isoquinolinyl groups, quinoxalinyl groups, and quinazolinyl groups; and C 1 -C 10 Alkyl group, C 1 -C 10 and selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, and a quinazolinyl group, each of which is substituted with at least one selected from an alkoxy group and a phenyl group.
[0028] As yet another example, in Formula 1, Ar 1 From Ar 6 are independently selected from the groups represented by the following chemical formulas 5-1 to 5-50 and 6-1 to 6-124. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0029] In the chemical formulas 5-1 to 5-50 and 6-1 to 6-124, Y 31 and Y 32 are independent of each other, O, S, C(Z 33 )(Z 34 ), N(Z 35 ) or Si(Z 36 )(Z 37 ) and Y 41 is N or C(Z 41 ), and Y 42 is N or C(Z 42 ), and Y 43 is N or C(Z 43 ), and Y 44 is N or C(Z 44 ), and Y 51 is N or C(Z 51 ), and Y 52 is N or C(Z 52 ), and Y 53 is N or C(Z 53 ), and Y 54 is N or C(Z 54 ) and In formulas 6-118 to 5-121, Y 41 From Y 43 At least one of, and Y 51 From Y 54 At least one of is N, In the formula 6-122, Y 41 From Y 44 At least one of, and Y 51 From Y 54 At least one of is N, Z 31 From Z 38 , Z 41 From Z 44 , and Z 51 From Z 54 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -CF 3 , hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20alkoxy groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclopentenyl groups, cyclohexenyl groups, phenyl groups, biphenyl groups, terphenyl groups, pentalenyl groups, indenyl groups, naphthyl groups, azulenyl groups, heptalenyl groups, indacenyl groups, acenaphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenalenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, Triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, isoindolyl group , indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, -Zolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilolyl group and -Si(Q 31 )(Q 32 )(Q 33 ), Q 1 From Q 3 , and Q 31 From Q 33 are independent of each other, C 1 -C 10Alkyl group, C 1 -C 10 alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, pyridinyl groups, pyrimidinyl groups, pyrazinyl groups, quinolinyl groups, isoquinolinyl groups, quinoxalinyl groups, and quinazolinyl groups; and C 1 -C 10 Alkyl group, C 1 -C 10 a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, and a quinazolinyl group, each of which is substituted with at least one selected from an alkoxy group and a phenyl group; e2 is selected from the integers 0 to 2, e3 is selected from the integers 0 to 3, e4 is selected from the integers 0 to 4; e5 is selected from the integers 0 to 5; e6 is selected from the integers 0 to 6, e7 is selected from the integers 0 to 7, e9 is selected from the integers 0 to 9, * indicates a bonding site with an adjacent atom.
[0030] According to one embodiment, in Formula 1, Ar 1 From Ar 6 are independently selected from the groups represented by the following formulae 9-1 to 9-116 and 10-1 to 10-121: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0031] In formulae 9-1 to 9-116 and formulae 10-1 to 10-121, Ph is a phenyl group, and * is a bonding site with the adjacent atom.
[0032] According to another embodiment, in Formula 1, Ar1 From Ar 6 are independently selected from the groups represented by the above chemical formulas 5-1 to 5-50 and 6-1 to 6-3 (for example, the groups represented by the above chemical formulas 9-1 to 9-116 and 10-1 to 10-3).
[0033] In Formula 1, b1 to b6 are each independently selected from integers of 1 to 5. b1 is Ar 1 When b1 is 2 or more, two or more Ar 1 may be the same or different. The explanation of b2 to b6 can be understood with reference to the explanation of b1 and the structure of Chemical Formula 1.
[0034] According to one embodiment, in Formula 1, b1 to b6 are, independently of one another, 1 or 2. According to another embodiment, in Formula 1, b1 to b6 are, independently of one another, 1 or 2.
[0035] In formula 1, R 1 From R 5 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl groups, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60Aryl groups, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic groups, -Si(Q 1 )(Q 2 )(Q 3 ), -N(Q 1 )(Q 2 ), -B(Q 1 )(Q 2 ), -C(=O)(Q 1 ), -S(=O) 2 (Q 1 ), and -P(=O)(Q 1 )(Q 2 ) is selected.
[0036] For example, in formula 1, R 1 From R 5 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 20 Alkyl group and C 1 -C 20 Alkoxy groups; C substituted with at least one of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino and hydrazono groups; 1 -C 20 Alkyl group and C 1 -C 20 Alkoxy groups; Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthyl, fluorenyl, spiro-bifluorenyl, spiro-benzofluorene-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, pyrrolyl group, thiophenyl group, furanyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, isoindolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, ben azoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzo furanyl, dibenzothiophenyl, dibenzosilolyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, oxazolopyridinyl, thiazolopyridinyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, and azadibenzosilolyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1-C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups, terphenyl groups and -Si(Q 31 )(Q 32 )(Q 33a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a spiro-benzofluorene-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanyl group, Anthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, pyrrolyl group, thiophenyl group, furanyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, isoindolyl group, indazolyl group, purinyl group, quinolinyl group, iso Quinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzyl group, azafuranyl group, dibenzothiophenyl group, dibenzosilolyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, oxazolopyridinyl group, thiazolopyridinyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group and azadibenzosilolyl group; Q 31 From Q 33 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, pyridinyl groups, pyrimidinyl groups, pyrazinyl groups, quinolinyl groups, isoquinolinyl groups, quinoxalinyl groups, and quinazolinyl groups; and C 1 -C 10 Alkyl group, C 1 -C 10 and selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, and a quinazolinyl group, each of which is substituted with at least one selected from an alkoxy group and a phenyl group.
[0037] According to one embodiment, in Formula 1, R 1 From R 5 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, mesityl group and -Si(Q 1 )(Q 2 )(Q 3 ) (However, Q 1 From Q 3 are independent of each other, C 1 -C 20 Alkyl group, C 1 -C 20 alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups and naphthyl groups).
[0038] According to another embodiment, in Formula 1, R 1 From R 3 is hydrogen and R 4 and R 5 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 20 Alkyl group, C1 -C 20 It is selected from an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a mesityl group.
[0039] In Formula 1, c1 to c3 are each independently selected from integers of 0 to 5. c1 is R 1 If c1 is 2 or more, there are two or more R 1 may be the same or different. The explanation regarding c2 and c3 can be understood with reference to the explanation regarding c1 and the structure of Chemical Formula 1.
[0040] According to one embodiment, in Chemical Formula 1, c1 to c3 are, independently of each other, 0 or 1. According to another embodiment, in Chemical Formula 1, c1 to c3 are 0.
[0041] In Chemical Formula 1, n1 to n3 are each independently 0 or 1, but n1+n2+n3 is 1. n1 is [ka] indicates the number of groups represented.
[0042] According to one embodiment, in Chemical Formula 1, n1 and n2 are 0 and n3 is 1; alternatively, n1 and n3 are 0 and n2 is 1. Alternatively, n1 is 1 and n2 and n3 are 0. That is, the number of amino groups contained in the fused ring compound is 1.
[0043] For example, the fused ring compound may be represented by one of formulas 1A to 1C below. [ka]
[0044] In chemical formulas 1A to 1C, X 1 , ring A 1 From A 3 , L 1 From L 9 , a1 to a9, Ar 1 From Ar6 , b1 to b6, R 1 From R 3 The explanation regarding c1 to c3 is as described above.
[0045] According to another embodiment, the fused ring compound is represented by one of the following formulas 1-1 to 1-11: [ka] [ka]
[0046] In chemical formulas 1-1 to 1-11, X 1 , L 1 From L 9 , a1 to a9, Ar 1 From Ar 6 , b1 to b6, R 1 From R 3 The explanation regarding c1 to c3 is as follows.
[0047] For example, in chemical formulas 1-1 to 1-11, X 1 is O, S, C(R 4 )(R 5 ), Si(R 4 )(R 5 ) and B(R 4 ), L 1 From L 9 are independently selected from the groups represented by chemical formulas 3-1 to 3-102 (e.g., the groups represented by chemical formulas 4-1 to 4-57); a1 to a9 are each independently 0 or 1; Ar 1 From Ar 6 are independently selected from the groups represented by formulae 5-1 to 5-50 and 6-1 to 6-124 (e.g., the groups represented by formulae 9-1 to 9-116 and 10-1 to 10-121); b1 through b6 are 1, R 1 From R 3 is hydrogen, and R 4 and R 5 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 selected from alkoxy, phenyl, biphenyl, terphenyl and mesityl groups; c1 to c3 are 0 or 1.
[0048] According to another embodiment, the fused ring compound is represented by one of the following formulas 1(1) to 1(18): [ka] [ka] [ka]
[0049] Chemical formulas 1(1) to 1(18) R 4 and R 5 is as described above, R m1 From R m4 are R 1 Please refer to the description of R m5 From R m7 are R 2 Please refer to the description of R m8 From R m13 are R 3 Please refer to the description of In the chemical formulas 1(1), 1(3), 1(4), 1(6), 1(7), 1(9), 1(10), 1(12), 1(13), 1(15), 1(16) and 1(18), R m1 From R m7one of which is selected from the groups represented by the following chemical formulas N-1 to N-41; In the chemical formulas 1(2), 1(5), 1(8), 1(11), 1(14) and 1(17), R m1 From R m13 is selected from the groups represented by the following chemical formulas N-1 to N-41: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0050] In chemical formulas N-1 to N-41, * indicates the bonding site with the adjacent atom.
[0051] According to another embodiment, the fused ring compound is represented by one of formulas 1(1) to 1(18), wherein R 4 , R 5 , R m1 From R m13 is one of compounds 1 to 3608 listed in Table 1 below, but is not limited thereto: [Table 1] TIFF0007610915000066.tif239170TIFF0007610915000067.tif237170TIFF0007610915000068.tif241170TIFF0007610915000069.tif237170TIFF0007610915000070.tif237170TIFF0007610915000071.tif239170TIFF0007610915000072.tif240170TIFF0007610915000073.tif238170TIFF0007610915000074.tif239170TIFF0007610915000075.tif238170TIFF0007610915000076.tif237170TIFF0007610915000077.tif240170TIFF0007610915000078.tif239170TIFF0007610915000079.tif238170TIFF0007610915000080.tif238170TIFF0007610915000081.tif239170TIFF0007610915000082.tif238170TIFF0007610915000083.tif239170TIFF0007610915000084.tif240170TIFF0007610915000085.tif240170TIFF0007610915000086.tif239170TIFF0007610915000087.tif237170TIFF0007610915000088.tif239170TIFF0007610915000089.tif240170TIFF0007610915000090.tif236170TIFF0007610915000091.tif238170TIFF0007610915000092.tif237170TIFF0007610915000093.tif239170TIFF0007610915000094.tif238170TIFF0007610915000095.tif238170TIFF0007610915000096.tif237170TIFF0007610915000097.tif240170TIFF0007610915000098.tif238170TIFF0007610915000099.tif236170TIFF0007610915000100.tif238170TIFF0007610915000101.tif238170TIFF0007610915000102.tif236170TIFF0007610915000103.tif237170TIFF0007610915000104.tif237170TIFF0007610915000105.tif237170TIFF0007610915000106.tif238170TIFF0007610915000107.tif238170TIFF0007610915000108.tif239170TIFF0007610915000109.tif239170TIFF0007610915000110.tif238170TIFF0007610915000111.tif239170TIFF0007610915000112.tif236170TIFF0007610915000113.tif237170TIFF0007610915000114.tif238170TIFF0007610915000115.tif237170TIFF0007610915000116.tif237170TIFF0007610915000117.tif236170TIFF0007610915000118.tif238170TIFF0007610915000119.tif239170TIFF0007610915000120.tif236170TIFF0007610915000121.tif236170TIFF0007610915000122.tif238170TIFF0007610915000123.tif239170TIFF0007610915000124.tif236170TIFF0007610915000125.tif237170TIFF0007610915000126.tif239170TIFF0007610915000127.tif239170TIFF0007610915000128.tif237170TIFF0007610915000129.tif239170TIFF0007610915000130.tif238170TIFF0007610915000131.tif238170TIFF0007610915000132.tif239170TIFF0007610915000133.tif240170TIFF0007610915000134.tif239170TIFF0007610 915000135.tif238170TIFF0007610915000136.tif238170TIFF0007610915000137.tif238170TIFF0007610915000138.tif156170.
[0052] In Table 1, H is hydrogen, Me is a methyl group, Ph is a phenyl group, and Mes is a mesityl group.
[0053] The fused ring compound represented by Chemical Formula 1 has the following Core A (see Chemical Formula 1' below). Core A has a structure in which three types of cyclic groups are fused to a seven-membered ring, which improves structural stability. In addition, by changing the type of cyclic group, it is easy to control the hole transport ability and hole injection ability. [ka] Chemical formula 1´
[0054] In the fused ring compound represented by Chemical Formula 1, n1 to n3 are each independently 0 or 1, and n1+n2+n3 is 1. That is, the fused ring compound represented by Chemical Formula 1 is a monoamine-based compound in which the number of amino groups contained in the compound is 1. As a result, the fused ring compound can have high hole transport ability and hole injection ability.
[0055] Therefore, an electronic device, for example, an organic light emitting device, using the fused ring compound represented by Chemical Formula 1 can be driven at a low voltage, can emit light with high brightness, and has high efficiency and a long life. A method for synthesizing the fused ring compound represented by Chemical Formula 1 will be understood by those skilled in the art with reference to the examples described below.
[0056] At least one of the fused ring compounds represented by Chemical Formula 1 is used between a pair of electrodes of an organic light emitting device. For example, the fused ring compound may be included in at least one of a hole transport region and an emission layer. Alternatively, the fused ring compound represented by Chemical Formula 1 may be used as a material of a capping layer located outside the region sandwiched between the pair of electrodes of an organic light emitting device.
[0057] Thus, according to one embodiment, there is provided an organic light emitting device comprising a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode and including a light emitting layer, wherein the organic layer comprises one or more fused ring compounds represented by Chemical Formula 1.
[0058] In this specification, "(the organic layer) contains one or more fused ring compounds" is interpreted as "(the organic layer) may contain one fused ring compound belonging to the category of Chemical Formula 1, or two or more different fused ring compounds belonging to the category of Chemical Formula 1."
[0059] For example, the organic layer may contain only compound 1 as a fused ring compound. In this case, compound 1 may be present in the light-emitting layer of the organic light-emitting device. Alternatively, the organic layer may contain compound 1 and compound 2 as fused ring compounds. In this case, compound 1 and compound 2 may be present in the same layer (e.g., compound 1 and compound 2 are both present in the light-emitting layer) or may be present in different layers (e.g., compound 1 is present in the light-emitting layer, and compound 2 is present in the hole transport layer or hole injection layer).
[0060] According to one embodiment, The first electrode of the organic light-emitting device is an anode, The second electrode of the organic light-emitting device is a cathode, The organic layer of the organic light-emitting device includes a hole transport region interposed between the first electrode and the light-emitting layer, and an electron transport region interposed between the light-emitting layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, a light-emitting assist layer, an electron blocking layer, or any combination thereof; The electron transport region may include a hole blocking layer, a buffer layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0061] According to one embodiment, the hole transport region may include a fused ring compound represented by Chemical Formula 1. The hole transport region may include a hole transport layer, and the hole transport layer may include a compound represented by Chemical Formula 1. Alternatively, the hole transport region may include a hole injection layer, and the hole injection layer may include a compound represented by Chemical Formula 1, but the structure of the hole transport region is not limited thereto.
[0062] According to another embodiment, the light emitting layer may include a fused ring compound represented by Chemical Formula 1. The light emitting layer may further include a host in addition to the fused ring compound represented by Chemical Formula 1. According to one embodiment, the light emitting layer of the organic light emitting device includes a host and a dopant, the host may include a fluorescent host, and the dopant may include the fused ring compound represented by Chemical Formula 1, but the structure of the light emitting layer is not limited thereto.
[0063] The organic light emitting device may further include at least one of a first capping layer disposed on a path where light generated in the light emitting layer is extracted to the outside through a first electrode, and a second capping layer disposed on a path where light generated in the light emitting layer is extracted to the outside through a second electrode, and at least one of the first capping layer and the second capping layer may include one or more fused ring compounds. For example, the organic light emitting device may have i) a structure in which a first electrode, an organic layer, a second electrode, and a second capping layer are sequentially stacked, ii) a structure in which a first capping layer, a first electrode, an organic layer, and a second electrode are sequentially stacked, or iii) a structure in which a first capping layer, a first electrode, an organic layer, a second electrode, and a second capping layer are sequentially stacked, and at least one of the first capping layer and the second capping layer may include a fused ring compound.
[0064] In this specification, the term "organic layer" refers to any single and / or multiple layers interposed between a first electrode and a second electrode in an organic light-emitting device. The material contained in the "organic layer" is not limited to an organic material.
[0065] [Explanation regarding Figure 1] 1 is a schematic cross-sectional view of an organic light-emitting device 10 according to one embodiment of the present invention. The organic light-emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.
[0066] Hereinafter, a structure and a method for manufacturing an organic light emitting device 10 according to an embodiment of the present invention will be described with reference to FIG.
[0067] [First electrode 110] 1, a substrate is additionally disposed below the first electrode 110 or above the second electrode 190. As the substrate, a glass substrate or a plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness can be used.
[0068] The first electrode 110 is formed by depositing a first electrode material on a substrate using, for example, a deposition method or a sputtering method. When the first electrode 110 is an anode, the first electrode material is selected from materials having a high work function so as to facilitate hole injection.
[0069] The first electrode 110 is a reflective electrode, a semi-transparent electrode, or a transparent electrode. To form the first electrode 110 as a transparent electrode, the material for the first electrode is selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2Alternatively, to form the first electrode 110, which is a semi-transmissive electrode or a reflective electrode, the material for the first electrode is selected from, but is not limited to, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof.
[0070] The first electrode 110 may have a single-layer structure, which is a single layer, or a multi-layer structure having multiple layers, for example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but is not limited thereto.
[0071] [Organic layer 150] The organic layer 150 is disposed on the first electrode 110. The organic layer 150 includes an emitting layer.
[0072] The organic layer 150 may further include a hole transport region interposed between the first electrode 110 and the light emitting layer, and an electron transport region interposed between the light emitting layer and the second electrode 190.
[0073] [Hole transport region in organic layer 150] The hole transport region can have i) a monolayer structure having a single layer of a single material, ii) a monolayer structure having a single layer of multiple different materials, or iii) a multilayer structure having multiple layers of multiple different materials.
[0074] The hole transport region may include at least one layer selected from a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting auxiliary layer, and an electron blocking layer (EBL).
[0075] For example, the hole transport region may have a single layer structure consisting of a single layer made of multiple different materials, or may have a multi-layer structure of a hole injection layer / hole transport layer, a hole injection layer / hole transport layer / light emitting auxiliary layer, a hole injection layer / light emitting auxiliary layer, a hole transport layer / light emitting auxiliary layer, or a hole injection layer / hole transport layer / electron blocking layer, which are stacked in this order from the first electrode 110, but is not limited to these.
[0076] According to one embodiment, the hole transport region may include a fused ring compound represented by Chemical Formula 1. For example, the hole transport region may include a hole transport layer, and the hole transport layer may include a fused ring compound represented by Chemical Formula 1. In another example, the hole transport region may include a hole injection layer, and the hole injection layer may include a fused ring compound represented by Chemical Formula 1.
[0077] Alternatively, the hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by the following chemical formula 201, and a compound represented by the following chemical formula 202. [ka] [ka] [ka] Chemical formula 201 [ka] Chemical formula 202
[0078] In chemical formulas 201 and 202, L 201 From L 204 are each independently a substituted or unsubstituted C 3 -C 10 Cycloalkylene groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene groups, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene groups, substituted or unsubstituted C 1 -C 60 is selected from a heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, and a substituted or unsubstituted divalent non-aromatic fused polycyclic heterocyclic group; L 205 *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C 1 -C 20 Alkylene group, substituted or unsubstituted C 2 -C 20 Alkenylene group, substituted or unsubstituted C 3 -C 10 Cycloalkylene groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene groups, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene groups, substituted or unsubstituted C 1 -C 60 is selected from a heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, and a substituted or unsubstituted divalent non-aromatic fused polycyclic heterocyclic group; xa1 to xa4 are independently selected from integers of 0 to 3; xa5 is selected from the integers 1 to 10; R 201 From R 204 , and Q 201 are each independently a substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 1 -C 60 It is selected from a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused polycyclic heterocyclic group.
[0079] For example, in formula 202, R 201 and R 202 may be linked to each other via a single bond, a dimethylmethylene group, or a diphenylmethylene group; R 203 and R 204 may be linked to each other via a single bond, a dimethylmethylene group, or a diphenylmethylene group.
[0080] According to one embodiment, in formulas 201 and 202: L 201 From L 205are each independently a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picene group, an nylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubycenylene group, a coronenylene group, an ovalenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, and a pyridinylene group; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10Phenyl groups substituted with alkyl groups, phenyl groups substituted with -F, pentalenyl groups, indenyl groups, naphthyl groups, azulenyl groups, heptalenyl groups, indacenyl groups, acenaphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenalenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, triphenylenyl groups, pyrenyl groups, chrysenyl groups, naphthyl groups, Tacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, pyridinyl, -Si(Q 31 )(Q 32 )(Q 33 ), and -N(Q 31 )(Q 32 a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, or a naphthacenylene group, each of which is substituted with at least one selected from the group consisting of groups, picenylene groups, perylenylene groups, pentaphenylene groups, hexacenylene groups, pentacenylene groups, rubicenylene groups, coronenylene groups, ovalenylene groups, thiophenylene groups, furanylene groups, carbazolylene groups, indolylene groups, isoindolylene groups, benzofuranylene groups, benzothiophenylene groups, dibenzofuranylene groups, dibenzothiophenylene groups, benzocarbazolylene groups, dibenzocarbazolylene groups, dibenzosilolylene groups and pyridinylene groups; Q 31 From Q 33 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10It is selected from an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group.
[0081] According to another embodiment, xa1 to xa4 are, independently of each other, 0, 1 or 2.
[0082] According to yet other embodiments, xa5 is 1, 2, 3 or 4.
[0083] According to yet another embodiment, R 201 From R 204 , and Q 201 are each independently a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthyl group, tacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl and pyridinyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10Phenyl groups substituted with alkyl groups, phenyl groups substituted with -F, pentalenyl groups, indenyl groups, naphthyl groups, azulenyl groups, heptalenyl groups, indacenyl groups, acenaphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenalenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, triphenylenyl groups, pyrenyl groups, chrysenyl groups, naphthyl groups, Tacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, pyridinyl, -Si(Q 31 )(Q 32 )(Q 33 ), and -N(Q 31 )(Q 32 ), each of which is substituted with at least one selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, and a chrysenyl group. , naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl and pyridinyl; 31 From Q 33 The explanation regarding this is as described above.
[0084] According to yet another embodiment, in formula 201, R 201 From R 203at least one of which is independently selected from the group consisting of fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10 A phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, but is not limited thereto.
[0085] According to yet another embodiment, in formula 202, i) R 201 and R 202 are linked to each other via a single bond, and / or ii) R 203 and R 204 are linked to each other via a single bond.
[0086] According to yet another embodiment, in formula 202, R 201 From R 204 And at least one of them is Carbazolyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1 -C 10 A phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a carbazolyl group substituted with at least one selected from a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, but is not limited thereto.
[0087] The compound represented by chemical formula 201 is also represented by chemical formula 201A below. [ka] Chemical formula 201A
[0088] For example, the compound represented by formula 201 may also be represented by the following formula 201A(1), but is not limited thereto: [ka] Chemical formula 201A(1)
[0089] As yet another example, the compound represented by formula 201 may also be represented by the following formula 201A-1, but is not limited thereto: [ka] Chemical formula 201A-1
[0090] On the other hand, the compound represented by chemical formula 202 is also represented by the following chemical formula 202A. [ka] Chemical formula 202A
[0091] According to yet another embodiment, the compound represented by formula 202 may also be represented by formula 202A-1: [ka] Chemical formula 202A-1
[0092] Chemical formulas 201A, 201A(1), 201A-1, 202A and 202A-1, L 201 From L 203 , xa1 to xa3, xa5, and R 202 From R 204 The explanation regarding is as above. R 211 and R 212 The explanation regarding R 203 Refer to the explanation regarding R 213 From R 217 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10 Phenyl groups substituted with alkyl groups, phenyl groups substituted with -F, pentalenyl groups, indenyl groups, naphthyl groups, azulenyl groups, heptalenyl groups, indacenyl groups, acenaphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenalenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, triphenylenyl groups, pyrenyl groups, chrysenyl groups, naphthaceyl groups, The alkyl group is selected from the group consisting of a phenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group.
[0093] The hole transport region may include at least one compound selected from the following compounds HT1 to HT39, but is not limited thereto. [ka] [ka] [ka]
[0094] The thickness of the hole transport region is about 10 nm or more and about 10,00 nm or less, for example, about 10 nm or more and about 1,00 nm or less. When the hole transport region includes at least one layer of the hole injection layer and the hole transport layer, the thickness of the hole injection layer is about 10 nm or more and about 9,00 nm or less, for example, about 10 nm or more and about 1,00 nm or less, and the thickness of the hole transport layer is about 5 nm or more and about 2,00 nm or less, for example, about 10 nm or more and about 1,50 nm or less. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the above-mentioned ranges, satisfactory hole transport properties can be obtained without a substantial increase in driving voltage.
[0095] The light-emitting auxiliary layer is a layer that adjusts the optical resonance distance according to the wavelength of light emitted from the light-emitting layer and increases the light extraction efficiency, and the electron blocking layer is a layer that prevents electron injection from the electron transport region. The light-emitting auxiliary layer and the electron blocking layer may contain the above-mentioned materials.
[0096] [p-dopant] In addition to the materials described above, the hole transport region may further include a charge generating material to enhance electrical conductivity. The charge generating material may be dispersed uniformly or non-uniformly within the hole transport region.
[0097] The charge generating material can be, for example, a p-dopant.
[0098] According to one embodiment, the lowest unoccupied molecular orbital (LUMO) level of the p-dopant may be less than or equal to -3.5 eV.
[0099] The p-dopant may include at least one selected from quinone derivatives, metal oxides, and cyano group-containing compounds, but is not limited thereto.
[0100] For example, the p-dopant may include at least one selected from the group consisting of quinone derivatives such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ); metal oxides such as tungsten oxide and molybdenum oxide; 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile (HAT-CN); and compounds represented by the following chemical formula 221, but are not limited thereto. [ka] HAT-CN [ka] F4-TCNQ [ka] chemical formula 221
[0101] In the chemical formula 221, R 221 From R 223 are each independently a substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C60 Aryl groups, substituted or unsubstituted C 1 -C 60 R is selected from a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused polycyclic heterocyclic group; 221 From R 223 At least one of the C substituted with a cyano group, -F, -Cl, -Br, -I, or -F 1 -C 20 Alkyl group, C substituted with -Cl 1 -C 20 C substituted with alkyl group, -Br 1 -C 20 C substituted with alkyl group and -I 1 -C 20 It has at least one substituent selected from an alkyl group.
[0102] [Light-emitting layer in organic layer 150] When the organic light emitting device 10 is used in a full color display device, the light emitting layer is patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer for each subpixel. Alternatively, the light emitting layer may have a structure in which two or more layers selected from a red light emitting layer, a green light emitting layer, and a blue light emitting layer are stacked in contact with each other or at a distance from each other, or a structure in which two or more materials selected from a red light emitting material, a green light emitting material, and a blue light emitting material are mixed in the same layer, and white light can be emitted. The light emitting layer may include a fused ring compound represented by Chemical Formula 1.
[0103] The light-emitting layer may include a host and a dopant. The dopant may include at least one of a phosphorescent dopant and a fluorescent dopant.
[0104] In the light-emitting layer, the content of the dopant is generally selected in the range of about 0.01 to about 15 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.
[0105] The thickness of the light-emitting layer is about 10 nm or more and about 1.00 nm or less, for example, about 20 nm or more and about 60 nm or less. When the thickness of the light-emitting layer satisfies this range, excellent light-emitting characteristics can be exhibited without a substantial increase in driving voltage.
[0106] [Host in the light-emitting layer] The host may include a compound represented by formula 301 below. [ka] chemical formula 301
[0107] In chemical formula 301, Ar 301 is a substituted or unsubstituted C 5 -C 60 a carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group; xb11 is 1, 2 or 3; L 301 is a substituted or unsubstituted C 3 -C 10 Cycloalkylene groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene groups, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene groups, substituted or unsubstituted C 1 -C 60 is selected from a heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, and a substituted or unsubstituted divalent non-aromatic fused polycyclic heterocyclic group; xb1 is selected from the integers 0 to 5; R 301 is deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl groups, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic groups, -Si(Q 301 )(Q 302 )(Q 303 ), -N(Q 301 )(Q 302 ), -B(Q 301 )(Q 302 ), -C(=O)(Q 301 ), -S(=O) 2 (Q 301 ), and -P(=O)(Q 301 )(Q 302 ), xb21 is selected from integers from 1 to 5; Q 301 From Q 303 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10 It may also be selected from, but is not limited to, alkoxy, phenyl, biphenyl, terphenyl and naphthyl groups.
[0108] According to one embodiment, in formula 301, Ar 301 teeth, naphthalene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, indenoanthracene, dibenzofuran, and dibenzothiophene groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, and a dibenzothiophene group; Q 31 From Q 33 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10 It is selected from, but not limited to, an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
[0109] In the formula 301, when xb11 is 2 or more, two or more Ar 301 are also linked to each other via a single bond.
[0110] According to another embodiment, the compound represented by formula 301 may also be represented by formula 301-1 or 301-2: [ka] Chemical formula 301-1 [ka] Chemical formula 301-2
[0111] Chemical formulas 301-1 and 301-2: A 301 From A 304 are independently selected from a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a pyridine group, a pyrimidine group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, an indole group, a carbazole group, a benzocarbazole group, a dibenzocarbazole group, a furan group, a benzofuran group, a dibenzofuran group, a naphthofuran group, a benzonaphthofuran group, a dinaphthofuran group, a thiophene group, a benzothiophene group, a dibenzothiophene group, a naphthothiophene group, a benzonaphthothiophene group, and a dinaphthothiophene group; X 301 is O, S or N-[(L 304 ) xb4 -R 304 ], R 311 From R 314 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ), xb22 and xb23 are independently 0, 1 or 2; L 301 , xb1, R 301 , and Q 31 From Q 33 The explanation regarding is as described above. L 302 From L 304 The explanations for L 301 Refer to the explanation regarding The explanations of xb2 to xb4 refer to the explanation of xb1 independently of each other. R 302 From R 304 The explanations related to 301 Please refer to the explanation related to.
[0112] For example, in formulas 301, 301-1 and 301-2, L 301 From L 304 are independent of each other, Phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindolylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylene group, imidazolylene group, pyrazolylene group, thiazolylene group , isothiazolylene groups, oxazolylene groups, isoxazolylene groups, thiadiazolylene groups, oxadiazolylene groups, pyrazinylene groups, pyrimidinylene groups, pyridazinylene groups, triazinylene groups, quinolinylene groups, isoquinolinylene groups, benzoquinolinylene groups, phthalazinylene groups, naphthyridinylene groups, quinoxalinylene groups, quinazolinylene groups, cinnolinylene groups, phenanthridinylene groups, acridinylene groups, phenanthrolinylene groups, phenazinylene groups, benzimidazolylene groups, isobenzothiazolylene groups, benzoxazolylene groups, isobenzoxazolylene groups, triazolylene groups, tetrazolylene groups, imidazopyridinylene groups, imidazopyrimidinylene groups, and azacarbazolylene groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazo -aryl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, or a pyrazolylene group, groups, thiazolylene groups, isothiazolylene groups, oxazolylene groups, isoxazolylene groups, thiadiazolylene groups, oxadiazolylene groups, pyrazinylene groups, pyrimidinylene groups, pyridazinylene groups, triazinylene groups, quinolinylene groups, isoquinolinylene groups, benzoquinolinylene groups, phthalazinylene groups, naphthyridinylene groups, quinoxalinylene groups, quinazolinylene groups, cinnolinylene groups, phenanthridinylene groups, acridinylene groups, phenanthrolinylene groups, phenazinylene groups, benzimidazolylene groups, isobenzothiazolylene groups, benzoxazolylene groups, isobenzoxazolylene groups, triazolylene groups, tetrazolylene groups, imidazopyridinylene groups, imidazopyrimidinylene groups and azacarbazolylene groups; Q 31 From Q 33 The explanation regarding this is as described above.
[0113] As another example, in formulas 301, 301-1 and 301-2, R 301 From R 304 are independent of each other, Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, pyridinyl, imidazolyl, pyrazolyl , thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazo -aryl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group and an azacarbazolyl group; Q 31 From Q 33 The explanation regarding this is as described above.
[0114] As yet another example, the host may include an alkaline earth metal complex, for example, the host may be selected from a Be complex (e.g., compound H55 below), a Mg complex, and a Zn complex.
[0115] The host may include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and the following compounds H1 to H55, but is not limited thereto. [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0116] [Phosphorescent dopants included in the light-emitting layer of organic layer 150] The phosphorescent dopant may include an organometallic complex represented by formula 401: [ka] chemical formula 401 [ka] chemical formula 401
[0117] In chemical formula 401, M is selected from iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh) and thulium (Tm); L 401 is selected from the ligands represented by formula 402, xc1 is 1, 2 or 3, and when xc1 is 2 or more, two or more L 401 may be the same or different, L 402 is an organic ligand, xc2 is selected from an integer of 0 to 4, and when xc2 is 2 or more, two or more L 402 may be the same or different, X 401 From X 404 are, independently of each other, nitrogen or carbon; X 401 and X 403 are linked via a single or double bond, and X 402 and X 404 is linked via a single or double bond, A 401 and A 402 are independent of each other, C 5 -C 60 Carbocyclic group or C 1 -C 60 is a heterocyclic group, X 405 is a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*', *-C(Q 411 )(Q 412 )-*', *-C(Q 411 )=C(Q 412 )-*', *-C(Q 411 )=*' or *=C(Q 411 )=*', Q 411 and Q 412 is hydrogen, deuterium, C 1 -C 20 Alkyl group, C 1 -C 20an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group; X 406 is a single bond, O or S, R 401 and R 402 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 20 Alkyl groups, substituted or unsubstituted C 1 -C 20 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic groups, -Si(Q 401 )(Q 402 )(Q 403 ), -N(Q 401 )(Q 402 ), -B(Q 401 )(Q 402 ), -C(=O)(Q 401 ), -S(=O) 2 (Q 401 ), and -P(=O)(Q 401 )(Q 402 ), Q 401 From Q 403 are independent of each other, C1 -C 10 Alkyl group, C 1 -C 10 Alkoxy group, C 6 -C 20 Aryl groups and C 1 -C 20 heteroaryl groups; xc11 and xc12 are independently selected from integers of 0 to 10; In chemical formula 402, * and *' are binding sites to M in chemical formula 401.
[0118] According to one embodiment, in formula 402, A 401 and A 402 are also independently selected from the group consisting of benzene, naphthalene, fluorene, spiro-bifluorene, indene, pyrrole, thiophene, furan, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, quinoline, isoquinoline, benzoquinoline, quinoxaline, quinazoline, carbazole, benzimidazole, benzofuran, benzothiophene, isobenzothiophene, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran and dibenzothiophene.
[0119] According to another embodiment, in formula 402, i) X 401 is nitrogen and X 402 is carbon, or ii) X 401 and X4 02 Both are nitrogen.
[0120] According to yet another embodiment, in formula 402, R 401 and R 402 are independent of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C20 Alkyl group and C 1 -C 20 Alkoxy groups; C substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a phenyl group, a naphthyl group, a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, and a norbornenyl group; 1 -C 20 Alkyl group and C 1 -C 20 Alkoxy groups; cyclopentyl group, cyclohexyl group, adamantanyl group, norbornanyl group, norbornenyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 a few groups selected from an alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; cyclopentyl, cyclohexyl, adamantanyl, norbornanyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl groups, each substituted with at least one of the following: -Si(Q 401 )(Q 402 )(Q 403 ), -N(Q 401 )(Q 402 ), -B(Q 401 )(Q 402 ), -C(=O)(Q 401 ), -S(=O) 2 (Q 401 ) and -P(=O)(Q 401 )(Q 402 ); Q 401 From Q 403 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10 It is selected from, but not limited to, an alkoxy group, a phenyl group, a biphenyl group, and a naphthyl group.
[0121] According to yet another embodiment, in formula 401, when xc1 is 2 or more, two or more L 401 In this case, two A 401 is a linking group, X 407 Alternatively, two A 402 is a linking group, X 408 (see compounds PD1 to PD4 and PD7 below). 407 and X 408 are, independently of each other, a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 413 )-*', *-C(Q 413 )(Q 414 )-*' or *-C(Q 413 )=C(Q 414 )-*'(where Q 413 and Q 414 are independently hydrogen, deuterium, and C 1 -C 20 Alkyl group, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl or naphthyl groups), but are not limited thereto.
[0122] Chemical Formula 401 L 402 is any monovalent, divalent or trivalent organic ligand. For example, L 402 is selected from, but is not limited to, halogen, diketone (e.g., acetylacetonate), carboxylic acid (e.g., picolinate), -C(=O), isonitrile, -CN, and phosphorus (e.g., phosphine, phosphite).
[0123] Alternatively, the phosphorescent dopant may be selected from, for example, but not limited to, the following compounds PD1 to PD25. [ka] [ka] [ka]
[0124] [Fluorescent dopants in the light-emitting layer] The fluorescent dopant may include a fused ring compound represented by Chemical Formula 1. Alternatively, the fluorescent dopant may include an arylamine compound or a styrylamine compound.
[0125] The fluorescent dopant may include a compound represented by formula 501: [ka] chemical formula 501 In the chemical formula 501, Ar 501 is a substituted or unsubstituted C 5 -C 60 Carbocyclic groups, or substituted or unsubstituted C 1 -C 60 is a heterocyclic group, L 501 From L 503are each independently a substituted or unsubstituted C 3 -C 10 Cycloalkylene groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene groups, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene groups, substituted or unsubstituted C 1 -C 60 is selected from a heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, and a substituted or unsubstituted divalent non-aromatic fused polycyclic heterocyclic group; xd1 to xd3 are independently selected from integers from 0 to 3; R 501 and R 502 are each independently a substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 1 -C 60 is selected from a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused polycyclic heterocyclic group; xd4 is selected from integers from 1 to 6.
[0126] According to one embodiment, the compound represented by formula 501 is Ar501 teeth, a naphthalene ring, a heptalene ring, a fluorene ring, a spiro-bifluorene ring, a benzofluorene ring, a dibenzofluorene ring, a phenalene ring, a phenanthrene ring, an anthracene ring, a fluoranthene ring, a triphenylene ring, a pyrene ring, a chrysene ring, a naphthacene ring, a picene ring, a perylene ring, a pentaphene ring, an indenoanthracene ring, and an indenophenanthrene ring; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 and a naphthalene ring, a heptalene ring, a fluorene ring, a spiro-bifluorene ring, a benzofluorene ring, a dibenzofluorene ring, a phenalene ring, a phenanthrene ring, an anthracene ring, a fluoranthene ring, a triphenylene ring, a pyrene ring, a chrysene ring, a naphthacene ring, a picene ring, a perylene ring, a pentaphene ring, an indenoanthracene ring, and an indenophenanthrene ring, each of which is substituted with at least one selected from an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
[0127] According to another embodiment, in formula 501, L 501 From L 503 are independent of each other, phenylene groups, naphthylene groups, fluorenylene groups, spiro-bifluorenylene groups, benzofluorenylene groups, dibenzofluorenylene groups, phenanthrenylene groups, anthracenylene groups, fluoranthenylene groups, triphenylenylene groups, pyrenylene groups, chrysenylene groups, perylenylene groups, pentaphenylene groups, hexacenylene groups, pentacenylene groups, thiophenylene groups, furanylene groups, carbazolylene groups, indolylene groups, isoindolylene groups, benzofuranylene groups, benzothiophenylene groups, dibenzofuranylene groups, dibenzothiophenylene groups, benzocarbazolylene groups, dibenzocarbazolylene groups, dibenzosilolylene groups, pyridinylene groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridinyl group. a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group;
[0128] According to yet another embodiment, in formula 501, R 501 and R 502 are independent of each other, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl and pyridinyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, triphenylenyl groups, pyrenyl groups, chrysenyl groups, perylenyl groups, pentaphenyl groups, hexacenyl groups, pentacenyl groups, thiophenyl groups, furanyl groups, carbazolyl groups, indolyl groups, isoindolyl groups, benzofuranyl groups, benzothiophenyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, benzocarbazolyl groups, dibenzocarbazolyl groups, dibenzosilolyl groups, pyridinyl groups and -Si(Q 31 )(Q 32 )(Q 33phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl and pyridinyl groups, Q 31 From Q 33 is C 1 -C 10 Alkyl group, C 1 -C 10 It is also selected from alkoxy, phenyl, biphenyl, terphenyl and naphthyl groups.
[0129] According to yet another embodiment, xd4 in formula 501 is 2, but is not limited thereto.
[0130] For example, the fluorescent dopant is selected from the following compounds FD1 to FD22. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0131] Alternatively, the fluorescent dopant is selected from the following compounds, but is not limited thereto: [ka] [ka]
[0132] [Electron transport region in organic layer 150] The electron transport region can have i) a monolayer structure consisting of a single layer of a single material, ii) a monolayer structure consisting of a single layer of multiple different materials, or iii) a multilayer structure having multiple layers consisting of multiple different materials.
[0133] The electron transport region may include, but is not limited to, at least one selected from a buffer layer, a hole blocking layer, an electron modulating layer, an electron transport layer (ETL), and an electron injection layer.
[0134] For example, the electron transport region may have a structure such as, but is not limited to, an electron transport layer / electron injection layer, a hole blocking layer / electron transport layer / electron injection layer, an electron control layer / electron transport layer / electron injection layer, or a buffer layer / electron transport layer / electron injection layer, which are stacked in this order from the light emitting layer.
[0135] An electron transport region (eg, a buffer layer, a hole blocking layer, an electron modulating layer, or an electron transport layer in an electron transport region) may comprise a non-metal-containing compound that contains at least one π-electron deficient nitrogen-containing ring.
[0136] A "π-electron deficient nitrogen-containing ring" is a ring-forming unit having at least one *-N=*' unit.1 -C 60 It means a heterocyclic group.
[0137] For example, the "π-electron deficient nitrogen-containing ring" is i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' unit, ii) a heteropolycyclic group in which two or more of the 5- to 7-membered heteromonocyclic groups having at least one *-N=*' unit are condensed with each other, or iii) a heteropolycyclic group in which at least one of the 5- to 7-membered heteromonocyclic groups having at least one *-N=*' unit and at least one C 5 -C 60 A heteropolycyclic group is a group in which a carbocyclic group and a heterocyclic group are fused together.
[0138] Specific examples of the π-electron deficient nitrogen-containing ring include, but are not limited to, an imidazole ring, a pyrazole ring, a thiazole ring, an isothiazole ring, an oxazole ring, an isoxazole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, an indazole ring, a purine ring, a quinoline ring, an isoquinoline ring, a benzoquinoline ring, a phthalazine ring, a naphthyridine ring, a quinoxaline ring, a quinazoline ring, a cinnoline ring, a phenanthridine ring, an acridine ring, a phenanthroline ring, a phenazine ring, a benzimidazole ring, an isobenzothiazole ring, a benzoxazole ring, an isobenzoxazole ring, a triazole ring, a tetrazole ring, an oxadiazole ring, a triazine ring, a thiadiazole ring, an imidazopyridine ring, an imidazopyrimidine ring, and an azacarbazole ring.
[0139] For example, the electron transport region may include a compound represented by formula 601 below. [ka] chemical formula 601
[0140] In chemical formula 601, Ar 601 is a substituted or unsubstituted C 5 -C 60Carbocyclic groups, or substituted or unsubstituted C 1 -C 60 is a heterocyclic group, xe11 is 1, 2 or 3, L 601 is a substituted or unsubstituted C 3 -C 10 Cycloalkylene groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene groups, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene groups, substituted or unsubstituted C 1 -C 60 is selected from a heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, and a substituted or unsubstituted divalent non-aromatic fused polycyclic heterocyclic group; xe1 is selected from the integers 0 to 5, R 601 is a substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic groups, -Si(Q 601 )(Q 602)(Q 603 ), -C(=O)(Q 601 ), -S(=O) 2 (Q 601 ), and -P(=O)(Q 601 )(Q 602 ), Q 601 From Q 603 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group; xe21 is selected from integers from 1 to 5.
[0141] According to one embodiment, xe11 Ar 601 , and xe21 R 601 At least one of the above may contain the above-mentioned π-electron deficient nitrogen-containing ring.
[0142] According to one embodiment, the ring Ar601 in formula 601 is Benzene group, naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentaphene group, indenoanthracene group, dibenzofuran group, dibenzothiophene group, carbazole group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group , pyridazine groups, indazole groups, purine groups, quinoline groups, isoquinoline groups, benzoquinoline groups, phthalazine groups, naphthyridine groups, quinoxaline groups, quinazoline groups, cinnoline groups, phenanthridine groups, acridine groups, phenanthroline groups, phenazine groups, benzimidazole groups, isobenzothiazole groups, benzoxazole groups, isobenzoxazole groups, triazole groups, tetrazole groups, oxadiazole groups, triazine groups, thiadiazole groups, imidazopyridine groups, imidazopyrimidine groups and azacarbazole groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine ... a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; Q 31 From Q 33 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10 It is selected from an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group.
[0143] In formula 601, if xe11 is 2 or more, two or more Ar 601 are also linked to each other via a single bond.
[0144] According to another embodiment, the compound represented by formula 601 is Ar 601 is an anthracene group.
[0145] According to yet another embodiment, the compound represented by formula 601 may also be represented by formula 601-1: [ka] Chemical formula 601-1
[0146] In the chemical formula 601-1, X 614 is N or C(R 614 ) and X 615 is N or C(R 615 ) and X 616 is N or C(R 616 ) and X 614 From X 616 At least one of is N, L 611 From L 613 are independent of each other, L 601 Refer to the explanation regarding xe611 to xe613 are independent of each other, please refer to the explanation for xe1. R 611 From R 613 are, independently of each other, R 601 Refer to the explanation regarding R 614 From R 616 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 It is selected from an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group.
[0147] According to one embodiment, in formulas 601 and 601-1, L 601 , and L 611 From L 613 are independent of each other, Phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindolylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylene group, imidazolylene group, pyrazolylene group, thiazolylene group , isothiazolylene groups, oxazolylene groups, isoxazolylene groups, thiadiazolylene groups, oxadiazolylene groups, pyrazinylene groups, pyrimidinylene groups, pyridazinylene groups, triazinylene groups, quinolinylene groups, isoquinolinylene groups, benzoquinolinylene groups, phthalazinylene groups, naphthyridinylene groups, quinoxalinylene groups, quinazolinylene groups, cinnolinylene groups, phenanthridinylene groups, acridinylene groups, phenanthrolinylene groups, phenazinylene groups, benzimidazolylene groups, isobenzothiazolylene groups, benzoxazolylene groups, isobenzoxazolylene groups, triazolylene groups, tetrazolylene groups, imidazopyridinylene groups, imidazopyrimidinylene groups, and azacarbazolylene groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, azolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group , a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexaphenylene group ... a cenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group,triazinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinnolinylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzimidazolylene group, isobenzothiazolylene group, benzoxazolylene group, isobenzoxazolylene group, triazolylene group, tetrazolylene group, imidazopyridinylene group, imidazopyrimidinylene group and azacarbazolylene group; but are not limited thereto.
[0148] According to another embodiment, in formulas 601 and 601-1, xe1 and xe611 through xe613 are 0, 1 or 2, independently of each other.
[0149] According to yet another embodiment, in formulas 601 and 601-1, R 601 , and R 611 From R 613 are independent of each other, Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, pyridinyl, imidazolyl, pyrazolyl a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, azolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexa ... Saccenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group,benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl groups; and -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ); Q 601 and Q 602 The explanation regarding this is as described above.
[0150] The electron transport region may include at least one compound selected from the following compounds ET1 to ET36, but is not limited thereto. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0151] Alternatively, the electron transport region may include at least one compound selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-4-(4-ethylphenyl)-5-(4-tert-butylphenyl)-4H-1,2,4-triazole (TAZ), and NTAZ. [ka]
[0152] The thickness of the buffer layer, the hole blocking layer, or the electron control layer may be, independently of one another, from about 2 nm to about 1.00 nm, for example, from about 3 nm to about 30 nm. When the thickness of the buffer layer, the hole blocking layer, or the electron control layer satisfies the above-mentioned range, excellent hole blocking properties or electron control properties can be obtained without a substantial increase in driving voltage.
[0153] The thickness of the electron transport layer is about 10 nm or more and about 1.00 nm or less, for example, about 15 nm or more and about 50 nm or less. When the thickness of the electron transport layer satisfies the above-mentioned range, satisfactory electron transport properties can be obtained without a substantial increase in driving voltage.
[0154] The electron transport region (eg, an electron transport layer in an electron transport region) may further include a metal-containing material in addition to the materials described above.
[0155] The metal-containing substance may include at least one selected from an alkali metal complex and an alkaline earth metal complex. The metal ion of the alkali metal complex is selected from Li ion, Na ion, K ion, Rb ion, and Cs ion, and the metal ion of the alkaline earth metal complex is selected from Be ion, Mg ion, Ca ion, Sr ion, and Ba ion. The ligands coordinated to the metal ion of the alkali metal complex and the alkaline earth metal complex are each independently selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but are not limited thereto.
[0156] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, the following compound ET-D1 (lithium quinolate (LiQ)) or ET-D2. [ka]
[0157] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.
[0158] The electron injection layer may have i) a single layer structure consisting of a single layer made of a single material, ii) a single layer structure consisting of single layers made of multiple different materials, or iii) a multilayer structure having multiple layers made of multiple different materials.
[0159] The electron injection layer may comprise an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0160] The alkali metal is selected from Li, Na, K, Rb and Cs.
[0161] According to one embodiment, the alkali metal is Li, Na or Cs. According to another embodiment, the alkali metal is Li or Cs, but is not limited thereto.
[0162] The alkaline earth metals are selected from Mg, Ca, Sr, and Ba.
[0163] The rare earth metal is selected from Sc, Y, Ce, Tb, Yb and Gd.
[0164] The alkali metal compounds, alkaline earth metal compounds and rare earth metal compounds are selected from oxides and halides (eg, fluorides, chlorides, bromides, iodides, etc.) of alkali metals, alkaline earth metals and rare earth metals.
[0165] Alkali metal compounds include Li 2 O, Cs 2 OK 2 The alkali metal compound is selected from alkali metal oxides such as LiF, LiO, and alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI. According to one embodiment, the alkali metal compound is LiF, Li 2 The inorganic oxide is selected from, but not limited to, O, NaF, LiI, NaI, CsI, and KI.
[0166] Alkaline earth metal compounds are BaO, SrO, CaO, Ba x Sr 1-x O(0 <x<1)、Ba x Ca 1-xIt is selected from alkaline earth metal compounds such as O(0 < x < 1). According to one embodiment, the alkaline earth metal compound is selected from, but not limited to, BaO, SrO, and CaO.
[0167] The rare earth metal compound is YbF 3 , ScF 3 , ScO 3 , Y 2 O 3 , Ce 2 O 3 , GdF 3 and TbF 3 selected from. According to one embodiment, the rare earth metal compound is YbF 3 , ScF 3 , TbF 3 , YbI 3 , ScI 3 , TbI 3 selected from, but not limited to, these.
[0168] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex contain the ions of the aforementioned alkali metal, alkaline earth metal, and rare earth metal, and the ligands coordinated to the metal ions of the alkali metal complex, alkaline earth metal complex, and rare earth metal complex are, independently of each other, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, pipyridine, phenanthroline, and cyclopentadiene, but are not limited to these.
[0169] The electron injection layer may be composed of the above-mentioned alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof, or may further contain an organic substance. When the electron injection layer further contains an organic substance, the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof is uniformly or non-uniformly dispersed in a matrix composed of an organic substance.
[0170] The thickness of the electron injection layer is from about 0.1 nm to about 10 nm, or from about 0.3 nm to about 9 nm. When the thickness of the electron injection layer satisfies the above-mentioned range, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.
[0171] [Second electrode 190] The second electrode 190 is disposed on the organic layer 150. The second electrode 190 also functions as a cathode, which is an electron injection electrode. In this case, the material for the second electrode 190 may be a metal, an alloy, an electrically conductive compound, or a combination thereof, each of which has a low work function.
[0172] The second electrode 190 may include at least one selected from, but is not limited to, lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, and IZO. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0173] The second electrode 190 can have a single-layer structure having a single layer, or a multi-layer structure having multiple layers.
[0174] [Explanation regarding Figures 2 to 4] The organic light-emitting device 20 of FIG. 2 has a structure in which a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190 are stacked in order, the organic light-emitting device 30 of FIG. 3 has a structure in which a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 are stacked in order, and the organic light-emitting device 40 of FIG. 4 has a structure in which a first capping layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 are stacked in order.
[0175] 2 to 4, the description of the first electrode 110, the organic layer 150, and the second electrode 190 may be referred to the description of FIG.
[0176] Light generated in the light-emitting layer in the organic layer 150 of the organic light-emitting element 20, 40 is extracted to the outside through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer 210, and light generated in the light-emitting layer in the organic layer 150 of the organic light-emitting element 30, 40 is extracted to the outside through the second electrode 190, which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer 220.
[0177] The first capping layer 210 and the second capping layer 220 may play a role in improving external light emission efficiency according to the principle of constructive interference.
[0178] The first capping layer 210 and the second capping layer 220 may be, independently of each other, an organic capping layer made of an organic material, an inorganic capping layer made of an inorganic material, or a composite capping layer containing an organic material and an inorganic material.
[0179] At least one of the first capping layer 210 and the second capping layer 220 may independently include at least one material selected from a carbocyclic compound, a heterocyclic compound, an amine-based compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, and an alkaline earth metal complex. A substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I may be introduced into the carbocyclic compound, the heterocyclic compound, and the amine-based compound.
[0180] According to an embodiment, at least one of the first capping layer 210 and the second capping layer 220 may independently include an amine-based compound. According to another embodiment, at least one of the first capping layer 210 and the second capping layer 220 may independently include a fused ring compound represented by Chemical Formula 1.
[0181] According to another embodiment, at least one of the first capping layer 210 and the second capping layer 220 may independently include a compound represented by Formula 201 or a compound represented by Formula 202.
[0182] According to yet another embodiment, at least one of the first capping layer 210 and the second capping layer 220 may comprise, independently of each other, a compound selected from compounds HT28 to HT33, and compounds CP1 to CP5 below, but is not limited thereto. [ka]
[0183] The organic light-emitting device has been described above with reference to FIGS. 1 to 4, but is not limited thereto.
[0184] Each layer included in the hole transport region, the light emitting layer, and the electron transport region is formed in a predetermined region using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, ink jet printing, laser printing, and laser induced-thermal imaging (LITI).
[0185] When each layer included in the hole transport region, the light emitting layer, and each layer included in the electron transport region are formed by vacuum deposition, the deposition conditions are, for example, a deposition temperature of about 100° C. to about 500° C., a deposition temperature of about 10 -8 Torr or higher: approx. 10 -3 The pressure is selected within the range of less than torr and the deposition rate of about 0.01 nm / sec to about 10 nm / sec, taking into consideration the material contained in the layer to be formed and the structure of the layer to be formed.
[0186] When each layer included in the hole transport region, the light-emitting layer, and each layer included in the electron transport region are formed by a spin coating method, the coating conditions are selected in consideration of the materials included in the layers to be formed and the structure of the layers to be formed, for example, within a substrate rotation speed of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature range of about 80°C to 200°C.
[0187] [General definition of substituents] In this specification, C 1 -C 60 The alkyl group means a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, a hexyl group, and the like. 1 -C 60 The alkylene group is C 1 -C 60 It means a divalent group having the same structure as an alkyl group.
[0188] In this specification, C 2 -C 60 The alkenyl group is C 2 -C 60 It means a hydrocarbon group containing one or more carbon-carbon double bonds in the middle or at the end of the alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, and a butenyl group. 2 -C 60 The alkenylene group is C 2 -C 60 It means a divalent group having the same structure as an alkenyl group.
[0189] In this specification, C 2 -C 60 The alkynyl group is C 2 -C 60 It means a hydrocarbon group containing one or more carbon-carbon triple bonds in the middle or at the end of the alkyl group, and specific examples thereof include an ethynyl group, a propynyl group, and the like. 2 -C 60 The alkynylene group is C 2 -C 60 It means a divalent group having the same structure as an alkynyl group.
[0190] In this specification, C 1 -C 60 The alkoxy group is -OA. 101 (Here, A 101 is C 1 -C 60 Specific examples of the aryl group include methoxy, ethoxy, and isopropyloxy groups.
[0191] In this specification, C 3 -C 10 The cycloalkyl group means a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and the like. 3 -C 10 The cycloalkylene group is C 3 -C10 It means a divalent group having the same structure as a cycloalkyl group.
[0192] In this specification, C 1 -C 10 The heterocycloalkyl group means a monovalent monocyclic group having 1 to 10 carbon atoms and containing at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, and specific examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and the like. 1 -C 10 The heterocycloalkylene group is 1 -C 10 It means a divalent group having the same structure as a heterocycloalkyl group.
[0193] In this specification, C 3 -C 10 The cycloalkenyl group means a monovalent monocyclic group having 3 to 10 carbon atoms, which has at least one carbon-carbon double bond in the ring but does not have aromaticity. Specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. 3 -C 10 The cycloalkenylene group is C 3 -C 10 It means a divalent group having the same structure as a cycloalkenyl group.
[0194] In this specification, C 1 -C 10 A heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms and containing at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, and having at least one carbon-carbon or carbon-heteroatom double bond in the ring. 1 -C 10Specific examples of the heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. 1 -C 10 The heterocycloalkenylene group is C 1 -C 10 It means a divalent group having the same structure as a heterocycloalkenyl group.
[0195] In this specification, C 6 -C 60 An aryl group means a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms, C 6 -C 60 An arylene group means a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Specific examples of the aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. 6 -C 60 Aryl groups and C 6 -C 60 When an arylene group contains two or more rings, the two or more rings may be fused together.
[0196] In this specification, C 1 -C 60 Heteroaryl group means a monovalent group having a heterocyclic aromatic system containing at least one heteroatom selected from N, O, Si, P and S as a ring atom and having 1 to 60 carbon atoms, C 1 -C 60 The heteroarylene group means a divalent group having a heterocyclic aromatic system containing at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom and having 1 to 60 carbon atoms. 1 -C 60 Specific examples of the heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. 1 -C 60 Heteroaryl groups and C 1-C 60 When a heteroarylene group contains two or more rings, the two or more rings may be fused together.
[0197] In this specification, C 6 -C 60 The aryloxy group is -OA. 102 (Here, A 102 is C 6 -C 60 aryl group), C 6 -C 60 The arylthio group is -SA 103 (Here, A 103 is C 6 -C 60 aryl group).
[0198] In this specification, a monovalent non-aromatic condensed polycyclic group refers to a monovalent group (e.g., having 8 to 60 carbon atoms) in which two or more rings are condensed with each other, the ring atoms are only carbon, and the entire molecule has non-aromaticity. Specific examples of monovalent non-aromatic condensed polycyclic groups include a fluorenyl group. In this specification, a divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as a monovalent non-aromatic condensed polycyclic group.
[0199] In the present specification, the term "non-aromatic condensed heteropolycyclic group" refers to a monovalent group (e.g., having 1 to 60 carbon atoms) in which two or more rings are condensed with each other and which contains at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom other than carbon, and the entire molecule has non-aromaticity. Specific examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. In the present specification, the term "divalent non-aromatic condensed heteropolycyclic group" refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
[0200] In this specification, C 5 -C60 A carbocyclic group refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms and containing only carbon as ring-forming atoms. 5 -C 60 A carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. 5 -C 60 A carbocyclic group can be a ring, such as benzene, a monovalent group, such as a phenyl group, or a divalent group, such as a phenylene group. 5 -C 60 Depending on the number of substituents connected to the carbocyclic group, the C5-C60 carbocyclic group can be a trivalent group or a tetravalent group, and various other variations are possible.
[0201] In the present specification, a C1-C60 heterocyclic group refers to a C 5 -C 60 It means a group having the same structure as a carbocyclic group, but containing at least one heteroatom selected from N, O, Si, P, and S in addition to carbon (which may have 1 to 60 carbon atoms) as ring-forming atoms.
[0202] As used herein, substituted C 5 -C 60 Carbocyclic groups, substituted C 1 -C 60 Heterocyclic groups, substituted C 3 -C 10 Cycloalkylene groups, substituted C 1 -C 10 Heterocycloalkylene groups, substituted C 3 -C 10 Cycloalkenylene groups, substituted C 1 -C 10 Heterocycloalkenylene groups, substituted C 6 -C 60 Arylene Groups, Substituted C 1 -C 60 Heteroarylene groups, substituted divalent nonaromatic condensed polycyclic groups, substituted divalent nonaromatic condensed heteropolycyclic groups, substituted C 1 -C 60 Alkyl groups, substituted C 2 -C 60 Alkenyl groups, substituted C2 -C 60 Alkynyl groups, substituted C 1 -C 60 Alkoxy groups, substituted C 3 -C 10 Cycloalkyl groups, substituted C 1 -C 10 Heterocycloalkyl groups, substituted C 3 -C 10 Cycloalkenyl groups, substituted C 1 -C 10 Heterocycloalkenyl Groups, Substituted C 6 -C 60 Aryl groups, substituted C 6 -C 60 Aryloxy groups, substituted C 6 -C 60 Arylthio groups, substituted C 1 -C 60 At least one of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituent of the substituted monovalent non-aromatic fused polycyclic heterocyclic group is Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C60 alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups and C1-C60 alkoxy groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) substituted with at least one selected from 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups and C 1 -C 60 Alkoxy groups; C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 ) substituted with at least one selected from 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups; and -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ); Q 11 From Q 13 , Q 21 From Q 23 , and Q 31 From Q 33 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 It is selected from a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.
[0203] As used herein, "Ph" means a phenyl group, "Me" means a methyl group, "Et" means an ethyl group, "ter-Bu" or "But" means a tert-butyl group, and "OMe" means a methoxy group.
[0204] In the present specification, the term "biphenyl group" means a "phenyl group substituted with a phenyl group." A "biphenyl group" is a group in which the substituent is "C6 -C 60 It belongs to the "substituted phenyl group" which is an "aryl group."
[0205] In the present specification, the term "terphenyl group" means a "phenyl group substituted with a biphenyl group." A "terphenyl group" is a group in which the substituent is "C 6 -C 60 Aryl-substituted C 6 -C 60 It belongs to the "substituted phenyl group" which is an "aryl group."
[0206] In this specification, unless otherwise defined, "* and *" refers to the bond sites between adjacent atoms in the chemical formula.
[0207] The compound and the organic light-emitting device according to the embodiment of the present invention will be described in more detail below with reference to synthesis examples and examples. In the synthesis examples below, in the expression "B was used instead of A," the molar equivalents of A and B are the same. EXAMPLES
[0208] Synthesis Example 1: Synthesis of Compound 1363 [ka]
[0209] Compound 1(10)-A (1.52 g, 5.00 mmol), amine compound N-10 (3.37 g, 10.5 mmol), Pd 2 (dba) 3 (69.6 mg, 0.076 mmol), PtBu 3(30.8 mg, 0.152 mmol) and NaOtBu (1.92 g, 20.0 mmol) were dissolved in 100 mL of toluene and stirred at 120° C. for 8 hours. The reaction mixture was cooled to room temperature, and then salt water and water were added, and the organic layer was extracted three times with diethyl ether. The separated organic layer was dried over magnesium sulfate, and the residue obtained by distilling off the solvent was purified by silica gel column chromatography to obtain 2.39 g (yield 81%) of compound 1363. The purified compound was analyzed by LC-MS (liquid chromatography-mass spectrometry) and 1 This was confirmed using 1 H NMR. C 45 H 35 N:M+1 589.28 1 H NMR (500 MHz, CDCl 3 )δ=7.96(2H,d),7.76-7.74(6H,m),7.60-7.37(20H,m),7.27(1H,d),1.58(6H,s)
[0210] Synthesis Example 2: Synthesis of Compound 1404 [ka]
[0211] The same method as in Synthesis Example 1 was used, except that compound 1(10)-B was used instead of compound 1(10)-A, to obtain 2.60 g of compound 1404 (yield 88%). The purified compound was analyzed by LC-MS and 1 This was confirmed using 1 H NMR. C 45 H 35 N:M+1 589.28 1 H NMR (500 MHz, CDCl 3 )δ=7.96(2H,d),7.76-7.75(6H,m),7.60-7.26(21H,m),1.69(6H,s)
[0212] Synthesis Example 3: Synthesis of Compound 2284 [ka]
[0213] Compound 1(13)-A, boronic acid of amine compound N-29, Pd(PPh 3 ) 4 and K 2 CO 3 was added to a mixture of tetrahydrofuran and water, and stirred at 100°C for 4 hours. The reaction mixture was cooled to room temperature, washed with brine, and extracted with diethyl ether three times. The organic layer was dried over magnesium sulfate, and the solvent was distilled off to obtain a residue, which was purified by silica gel column chromatography to obtain 2.84g (yield 78%) of compound 2284. The purified compound was analyzed by LC-MS and 1 Confirmed using H NMR C 51 H 39 FN 2 Si:M+1 726.29 1 H NMR (500 MHz, CDCl 3 )δ=8.19(1H,d),8.04-7.87(8H,m),7.37-7.34(4H,m),7.20-7.13(5H,m),2.32(3H,s),0.66(6H,s)
[0214] Synthesis Example 4: Synthesis of Compound 2766 [ka]
[0215] The same method as in Synthesis Example 1 was used, except that compound 1(13)-B was used instead of compound 1(10)-A, and amine compound N-19 was used instead of amine compound N-10, to obtain 2.90 g of compound 2766 (78% yield). The purified compound was analyzed by LC-MS and 1 This was confirmed using 1 H NMR. C 54 H 37 NOSi:M+1 743.26, 1 H NMR (500 MHz, CDCl 3)δ=8.10(1H,d),7.98-7.96(3H,m),7.60-7.31(30H,m),7.14-7.08(2H,m),6.97(1H,d)
[0216] Synthesis Example 5: Synthesis of Compound 126 [ka]
[0217] The same method as in Synthesis Example 1 was used, except that compound 1(2)-A was used instead of compound 1(10)-A, and amine compound N-3 was used instead of amine compound N-10, to obtain 2.19 g of compound 126 (yield 82%). The compound thus obtained was analyzed by LC-MS and 1 This was confirmed using 1 H NMR. C 37 H 31 NOSi:M+1 533.22, 1 H NMR (500 MHz, CDCl 3 )δ=8.10-8.04(3H,m),7.96(2H,d),7.83(1H,s),7.69(1H,d),7.61(1H,t ),7.60(2H,t),7.52(1H,dt),7.36(2H,d),7.24-7.00(9H,m),0.88(9H,s)
[0218] Synthesis Example 6: Synthesis of Compound 3239 [ka]
[0219] The same method as in Synthesis Example 3 was used, except that 1(16)-A was used instead of compound 1(13)-A, and boronic acid N-3 was used instead of boronic acid N-29 of amine compound, to obtain 2.95 g of compound 3239 (70% yield). The compound thus obtained was analyzed by LC-MS and 1 Confirmed via 1 H NMR. C 63 H 47 BN 2 :M+1 842.38, 1 H NMR (500 MHz, CDCl 3 )δ=8.19(1H,d),8.13(1H,d),8.01-7.87(7H,m),7.77-7.75(3H,m),7.62-7. 37(22H,m),7.20(1H,t),6.97(2H,s),6.48(1H,d),2.33(6H,s),2.18(3H,s)
[0220] [Example 1] Substrate and anode: Corning 15 Ω / cm 2 The glass substrate on which the (1.20 nm) ITO was formed was cut to a size of 50 mm x 50 mm x 0.7 mm, ultrasonically cleaned using isopropyl alcohol and pure water for 5 minutes each, irradiated with ultraviolet light for 30 minutes, and further cleaned by exposing to ozone. After that, the glass substrate was placed in a vacuum deposition apparatus.
[0221] On this ITO anode, 2-TNATA was vacuum-deposited to form a hole injection layer having a thickness of 60 nm, and on the hole injection layer, Compound 126 was vacuum-deposited to form a hole transport layer having a thickness of 30 nm.
[0222] On the hole transport layer, 9,10-di-naphthalene-2-yl-anthracene (ADN) (host) and compound FD1 (dopant) were co-deposited in a volume ratio of 98:2 to form a 30 nm-thick light-emitting layer.
[0223] Alq3 was vacuum-deposited on the light-emitting layer to form a 30 nm-thick electron transport layer, and then LiF was vapor-deposited on the electron transport layer to form a 1 nm-thick electron injection layer. After that, Al was vacuum-deposited to form a 3.00 nm-thick second electrode (cathode), and an organic light-emitting element was produced. [ka]
[0224] [Examples 2 to 6 and Comparative Examples 1 to 3] Organic light emitting devices of Examples 2 to 6 and Comparative Examples 1 to 3 were fabricated using the same method as in Example 1, except that the hole transport layer materials were changed as shown in Table 2.
[0225] [Evaluation example 1] The driving voltage, current density, luminance, efficiency and half-life of the organic light emitting devices fabricated in Examples 1 to 6 and Comparative Examples 1 to 3 were measured using a Kethley SMU 236 and a luminance meter PR650, and the results are shown in Table 2. The half-life is the time it takes for the luminance to decrease to 50% of the initial luminance after the organic light emitting device is driven. [Table 2] [ka]
[0226] From Table 2, it was confirmed that the organic light-emitting elements of Examples 1 to 6 can be driven at a lower voltage and exhibit high efficiency, and therefore can emit light with a higher brightness at the same current density, compared to the organic light-emitting elements of Comparative Examples 1 to 3, and further have a longer life. [Industrial Applicability]
[0227] The fused ring compound and the organic light emitting device including the same according to the present invention can be effectively applied to, for example, technical fields related to light emission. [Explanation of symbols]
[0228] 10,20,30,40 Organic light-emitting devices 110 1st electrode 150 Organic layer 190 2nd electrode 210 First capping layer 220 Second Capping Layer
Claims
1. A fused ring compound represented by the following chemical formula 1: 【Chemistry 1】 In the above Chemical Formula 1, X 1 is O, S, Se, C(R 4 ) (R 5 ), Si(R 4 ) (R 5 ) and B(R 4 ) are selected from Ring A 1 and A 3 are each independently a benzene group or a naphthalene group; A 2 is a benzene group, L 1 is a 1,4-phenylene group, L 2 From L 9 are each independently a substituted or unsubstituted C 3 -C 10 Cycloalkylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene group, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene group, substituted or unsubstituted C 1 -C 60 is selected from a heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, and a substituted or unsubstituted divalent non-aromatic fused polycyclic heterocyclic group; a1 is 0 or 1, and when a1 is 0, (L 1 ) a1 represents a single bond; a2 to a9 are each independently selected from integers of 0 to 5; Ar 1 From Ar 6 are each independently a substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 1 -C 60 is selected from a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused polycyclic heterocyclic group; b1 to b6 are independently selected from integers from 1 to 5; R 1 From R 3 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 Alkyl group, substituted or unsubstituted C 2 -C 60 Alkenyl group, substituted or unsubstituted C 2 -C 60 Alkynyl group, substituted or unsubstituted C 1 -C 60 Alkoxy group, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy group, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 ) (Q 2 ) (Q 3 ), -N(Q 1 ) (Q 2 ), -B(Q 1 ) (Q 2 ), -C(=O)(Q 1 ), -S(=O) 2 (Q 1 ), and -P(=O)(Q 1 ) (Q 2 ) are selected from R 4 and R 5 are identical and are selected from a methyl group, a phenyl group, and a 2,4,6-trimethylphenyl group; c1 to c3 are 0, n1 is 1, n2 is 0, and n3 is 0; The substituted C 3 -C 10 Cycloalkylene groups, substituted C 1 -C 10 Heterocycloalkylene Groups, Substituted C 3 -C 10 Cycloalkenylene group, substituted C 1 -C 10 Heterocycloalkenylene Groups, Substituted C 6 -C 60 Arylene Groups, Substituted C 1 -C 60 Heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 Alkyl groups, substituted C 2 -C 60 Alkenyl Groups, Substituted C 2 -C 60 Alkynyl Group, Substituted C 1 -C 60 Alkoxy groups, substituted C 3 -C 10 Cycloalkyl groups, substituted C 1 -C 10 Heterocycloalkyl groups, substituted C 3 -C 10 Cycloalkenyl Groups, Substituted C 1 -C 10 Heterocycloalkenyl Groups, Substituted C 6 -C 60 Aryl groups, substituted C 6 -C 60 Aryloxy groups, substituted C 6 -C 60 Arylthio group, substituted C 1 -C 60 At least one of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituent of the substituted monovalent non-aromatic fused polycyclic heterocyclic group is Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group and C 1 -C 60 Alkoxy group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 3 -C 10 Cycloalkyl group, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 ) (Q 12 ) (Q 13 ), -N(Q 11 ) (Q 12 ), -B(Q 11 ) (Q 12 ), -C(=O)(Q 11 ), -S(=O) 2 (Q 11 ) and -P(=O)(Q 11 ) (Q 12 C substituted with at least one selected from 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group and C 1 -C 60 Alkoxy group; C 3 -C 10 Cycloalkyl group, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups, and terphenyl groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl group, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 ) (Q 22 ) (Q 23 ), -N(Q 21 ) (Q 22 ), -B(Q 21 ) (Q 22 ), -C(=O)(Q 21 ), -S(=O) 2 (Q 21 ) and -P(=O)(Q 21 ) (Q 22 C substituted with at least one selected from 3 -C 10 Cycloalkyl group, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and -Si(Q 31 ) (Q 32 ) (Q 33 ), -N(Q 31 ) (Q 32 ), -B(Q 31 ) (Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 ) (Q 32 ); Q 1 From Q 3 , Q 11 From Q 13 , Q 21 From Q 23 , and Q 31 From Q 33 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl group, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 C substituted with alkyl group 6 -C 60 Aryl group, C 6 -C 60 C substituted with an aryl group 6 -C 60 Aryl group, C 1 -C 60 Heteroaryl group, C 1 -C 60 C substituted with alkyl group 1 -C 60 Heteroaryl group, C 6 -C 60 C substituted with an aryl group 1 -C 60 It is selected from a heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic hetero-fused polycyclic group, a biphenyl group, and a terphenyl group.
2. In Formula 1, L 2 From L 9 are independent of each other, Phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-bifluorenylene group, spiro-benzofluorene-fluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, perylenylene group, pentaphenylene group, a pyrrolylene group, a thiophenylene group, a furanylene group, a silolylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an indolylene group, an isoindolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinol ... A xalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, a benzofuranylene group, a benzothiophenylene group, a benzosilolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiofurylene group, phenylene groups, dibenzosilolylene groups, carbazolylene groups, benzocarbazolylene groups, dibenzocarbazolylene groups, thiadiazolylene groups, imidazopyridinylene groups, imidazopyrimidinylene groups, oxazolopyridinylene groups, thiazolopyridinylene groups, benzonaphthyridinylene groups, azafluorenylene groups, azaspiro-bifluorenylene groups, azacarbazolylene groups, azadibenzofuranylene groups, azadibenzothiophenylene groups, and azadibenzosilolylene groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, C 3 -C 10 Cycloalkyl group, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups, terphenyl groups and -Si(Q 31 ) (Q 32 ) (Q 33 a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a spiro-benzofluorene-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, or a chrysenylene group, each of which is substituted with at least one selected from the group consisting of group, a perylenylene group, a pentaphenylene group, a pyrrolylene group, a thiophenylene group, a furanylene group, a silolylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an indolylene group, an isoindolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthylene group, Lysinylene group, quinoxalinylene group, quinazolinylene group, cinnolinylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzimidazolylene group, benzofuranylene group, benzothiophenylene group, benzosilolylene group, isobenzothiazolylene group, benzoxazolylene group, isobenzoxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzo a thiophenylene group, a dibenzosilolylene group, a carbazolylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a thiadiazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, an oxazolopyridinylene group, a thiazolopyridinylene group, a benzonaphthyridinylene group, an azafluorenylene group, an azaspiro-bifluorenylene group, an azacarbazolylene group, an azadibenzofuranylene group, an azadibenzothiophenylene group, and an azadibenzosilolylene group; Q 31 From Q 33 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10 Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, pyridinyl groups, pyrimidinyl groups, pyrazinyl groups, quinolinyl groups, isoquinolinyl groups, quinoxalinyl groups, and quinazolinyl groups; and C 1 -C 10 Alkyl group, C 1 -C 10 2. The fused ring compound according to claim 1, wherein the substituted ring is selected from the group consisting of a phenyl group substituted with at least one selected from an alkoxy group and a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, and a quinazolinyl group.
3. In Formula 1, L 2 From L 9 are each independently selected from the group represented by one of the following chemical formulas 3-1 to 3-102: 【Chemistry 2】 【Chemistry 3】 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 In the above chemical formulas 3-1 to 3-102, Y 1 is O, S, C (Z 3 ) (Z 4 ), N(Z 5 ) or Si(Z 6 ) (Z 7 ) and Z 1 From Z 7 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, Triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, isoindolyl group group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, adiazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilolyl group, -Si(Q 31 ) (Q 32 ) (Q 33 ), -N(Q 31 ) (Q 32 ), -B(Q 31 ) (Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 ) (Q 32 ) are selected from Q 31 From Q 33 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10 Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, pyridinyl groups, pyrimidinyl groups, pyrazinyl groups, quinolinyl groups, isoquinolinyl groups, quinoxalinyl groups, and quinazolinyl groups; and C 1 -C 10 Alkyl group, C 1 -C 10 a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, and a quinazolinyl group, each of which is substituted with at least one selected from an alkoxy group and a phenyl group; d2 is selected from integers from 0 to 2; d3 is selected from integers from 0 to 3; d4 is selected from integers from 0 to 4; d5 is selected from the integers 0 to 5; d6 is selected from integers from 0 to 6; d8 is selected from integers from 0 to 8; * and *' are bonding sites with adjacent atoms.
4. In Formula 1, L 2 From L 9 are each independently selected from the groups represented by the following chemical formulas 4-1 to 4-57: 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 In the above formulas 4-1 to 4-57, Ph is a phenyl group, and * and *' are bonding sites with adjacent atoms.
5. The fused ring compound according to claim 1 , wherein a2 to a9 in the formula 1 are each independently 0 or 1.
6. In Formula 1, Ar 1 From Ar 6 are independent of each other, A phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a spiro-benzofluorene-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, Perylenyl group, pentaphenyl group, pyrrolyl group, thiophenyl group, furanyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, isoindolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothio phenyl, dibenzosilolyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, oxazolopyridinyl, thiazolopyridinyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, and azadibenzosilolyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, C 3 -C 10 Cycloalkyl group, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group, terphenyl group, -Si(Q 31 ) (Q 32 ) (Q 33 ), -N(Q 31 ) (Q 32 ), -B(Q 31 ) (Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 ) (Q 32 ) substituted with at least one selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a spiro-benzofluorene-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, and a triphenylenyl group; group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, pyrrolyl group, thiophenyl group, furanyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, isoindolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzo azathiophenyl group, dibenzosilolyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, oxazolopyridinyl group, thiazolopyridinyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group and azadibenzosilolyl group; Q 1 From Q 3 , and Q 31 From Q 33 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10 Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, pyridinyl groups, pyrimidinyl groups, pyrazinyl groups, quinolinyl groups, isoquinolinyl groups, quinoxalinyl groups, and quinazolinyl groups; and C 1 -C 10 Alkyl group, C 1 -C 10 The fused ring compound according to claim 1, which is selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group and a quinazolinyl group, each of which is substituted with at least one selected from an alkoxy group and a phenyl group.
7. In Formula 1, Ar 1 From Ar 6 are each independently selected from the groups represented by the following chemical formulas 5-1 to 5-50 and 6-1 to 6-124: 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemical 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 In the formulae 5-1 to 5-50 and 6-1 to 6-124, Y 31 and Y 32 are each independently O, S, C (Z 33 ) (Z 34 ), N(Z 35 ) or Si(Z 36 ) (Z 37 ) and Y 41 is N or C(Z 41 ) and Y 42 is N or C(Z 42 ) and Y 43 is N or C(Z 43 ) and Y 44 is N or C(Z 44 ) and Y 51 is N or C(Z 51 ) and Y 52 is N or C(Z 52 ) and Y 53 is N or C(Z 53 ) and Y 54 is N or C(Z 54 In the formulae 6-118 to 6-121, Y 41 From Y 43 , and Y 51 From Y 54 At least one is N, and in Formula 6-122, Y 41 From Y 44 , and Y 51 From Y 54 At least one of them is N, Z 31 From Z 38 , Z 41 From Z 44 , and Z 51 From Z 54 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, or -CF 3 , hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, Triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, isoindolyl group , indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, azolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzosilolyl group, and -Si(Q 31 ) (Q 32 ) (Q 33 ) are selected from Q 1 From Q 3 , and Q 31 From Q 33 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10 Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, pyridinyl groups, pyrimidinyl groups, pyrazinyl groups, quinolinyl groups, isoquinolinyl groups, quinoxalinyl groups, and quinazolinyl groups; and C 1 -C 10 Alkyl group, C 1 -C 10 a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, and a quinazolinyl group, each of which is substituted with at least one selected from an alkoxy group and a phenyl group; e2 is selected from integers from 0 to 2; e3 is selected from integers from 0 to 3; e4 is selected from integers from 0 to 4; e5 is selected from integers from 0 to 5; e6 is selected from integers from 0 to 6; e7 is selected from integers from 0 to 7; e9 is selected from integers from 0 to 9; * indicates a bonding site with an adjacent atom.
8. In Formula 1, Ar 1 From Ar 6 are each independently selected from the groups represented by the following chemical formulas 9-1 to 9-116 and 10-1 to 10-121: 【Chemical Formula 29】 【Chemistry 30】 【Chemistry 31】 【Chemistry 32】 【Chemical 33】 【Chemical 34】 【Chemistry 35】 【Chemical Formula 36】 【Chemical 37】 【Chemical Formula 38】 【Chemical Formula 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 In the above formulae 9-1 to 9-116 and 10-1 to 10-121, Ph is a phenyl group, and * is a bonding site with an adjacent atom.
9. In Formula 1, Ar 1 From Ar 6 are each independently selected from the groups represented by the formulas 9-1 to 9-116 and 10-1 to 10-3.
10. In Formula 1, R 1 From R 5 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, mesityl group, naphthyl group and -Si(Q 1 ) (Q 2 ) (Q 3 ) are selected from Q 1 From Q 3 are, independently of each other, C 1 -C 20 Alkyl group, C 1 -C 20 2. The fused ring compound of claim 1, wherein the aryl group is selected from an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
11. The fused ring compound according to claim 1 , represented by the following chemical formula 1A: 【Chemistry 49】
12. The fused ring compound according to claim 1, which is represented by one of the following chemical formulas 1-1 to 1-2. 【Chemistry 50】
13. A first electrode; a second electrode facing the first electrode; an organic layer interposed between the first electrode and the second electrode and including a light-emitting layer; The organic layer comprises the fused ring compound according to claim 1 .
14. the first electrode is an anode; the second electrode is a cathode; the organic layer includes a hole transport region interposed between the first electrode and the light emitting layer, and an electron transport region interposed between the light emitting layer and the second electrode; The hole transport region includes at least one of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, and an electron blocking layer, The organic light emitting device of claim 13 , wherein the electron transport region comprises at least one of a hole blocking layer, a buffer layer, an electron transport layer, and an electron injection layer.
15. The organic light-emitting device of claim 14 , wherein at least one of the hole transport region and the light-emitting layer includes the fused ring compound.
16. The organic light-emitting device according to claim 14 , wherein the hole transport region comprises a hole transport layer, and the hole transport layer comprises the fused ring compound.
17. The organic light-emitting device of claim 16 , wherein the hole transport region comprises a hole injection layer, and the hole injection layer comprises the fused ring compound.
Citation Information
Patent Citations
Light-emitting material for organic electroluminescent device, organic electroluminescent device using same, and material for organic electroluminescent device
KR1020150021861A
Electroluminescent device with anthracene derivatives hole transport layer
US20020028346A1
Substituted oxepines
WO2015082046A2