Condensed cyclic compound, composition including the same and organic light-emitting device including the same

Abstract

A condensed ring compound, a composition containing the same, and an organic light-emitting device containing the same are disclosed.

Description

Technology Field

[0001] The present invention relates to a condensed ring compound, a material for an organic light-emitting device comprising the same, and an organic light-emitting device comprising the same. Background Technology

[0002] Organic light-emitting devices are self-emissive devices that possess the advantages of a wide viewing angle and excellent contrast, as well as fast response time, superior characteristics in brightness, driving voltage, and response speed, and the ability to be multicolored.

[0003] According to one example, an organic light-emitting device may include an anode, a cathode, and an organic layer interposed between the anode and the cathode, which includes a light-emitting layer. A hole transport region may be provided between the anode and the light-emitting layer, and an electron transport region may be provided between the light-emitting layer and the cathode. Holes injected from the anode move to the light-emitting layer via the hole transport region, and electrons injected from the cathode move to the light-emitting layer via the electron transport region. Carriers such as holes and electrons recombine in the light-emitting layer region to generate excitons. Light is generated as these excitons change from an excited state to a ground state. The problem to be solved

[0004] The present invention provides a condensed ring compound, a composition containing the same, and an organic light-emitting device employing the same.

[0005] In the manufacture of organic light-emitting diodes, it is common practice to deposit organic films constituting the organic light-emitting diodes using dry deposition methods such as deposition. However, deposition using dry deposition methods such as deposition has the problem of requiring time and cost. Therefore, instead of using such dry deposition methods, wet deposition methods such as solution coating (hereinafter referred to as coating methods) are being considered to reduce time and cost.

[0006] However, when the wet deposition method is applied to existing compounds, there is a problem that the solution has a short pot life due to the low solubility of the compounds. In addition, aggregation of organic molecules in the light-emitting layer is likely to occur after deposition. Therefore, organic light-emitting devices formed by the coating method cannot obtain sufficient current efficiency and light-emitting lifetime.

[0007] Organic light-emitting devices using these compounds have problems with low efficiency and short lifespan.

[0008] Therefore, the present invention aims to provide a compound that has high solubility, a long pot life of the solution, and can achieve high efficiency and long lifespan of an organic light-emitting diode.

[0009] Specifically, an organic light-emitting device containing the above-mentioned condensed ring compound can provide high luminous efficiency and a long lifespan. In addition, the above-mentioned condensed ring compound has a low glass transition temperature and thus possesses high solubility; consequently, the pot life of a solution containing the compound is extended, making it suitable for use in solution coating methods. means of solving the problem

[0010] According to one aspect, a condensed ring compound represented by the following chemical formula 1 is disclosed:

[0011] <Chemical Formula 1>

[0012]

[0013] <Chemical Formula 2>

[0014]

[0015] Among the above chemical formulas 1 and 2,

[0016] L1 to L2 and L 11 C5-C pairs independently of each other, single-bonded, substituted, or unsubstituted 60 Carbocyclic groups, or substituted or unsubstituted C1-C 60 Selected from heterocyclic groups, and

[0017] a1 to a2 and a11 are independently selected from integers 1 to 5, and

[0018] Ar1 and Ar 11 C5-C5s are independently substituted or unsubstituted. 60 It is a cabocyclic group, and

[0019] R1 to R6 are independently a group represented by Chemical Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, or a substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C7-C 60 Alkyl aryl groups, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 Heteroaryl group, substituted or unsubstituted C2-C 60 Alkyl heteroaryl group, substituted or unsubstituted C1-C 60 Heteroaryloxy groups, substituted or unsubstituted C1-C 60 Selected from a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -Si(Q1)(Q2)(Q3) and -N(Q1)(Q2), and

[0020] b3, b5, and b6 are independently selected from integers 0 to 4, and

[0021] b2 is selected from integers from 0 to 3, and

[0022] Any two adjacent groups among R1, R2, b3, b4, b5, and b6 are optionally combined to form a substituted or unsubstituted C5-C 30 Carbocyclic groups or substituted or unsubstituted C1-C 30 It can form heterocyclic groups,

[0023] n1 is selected from integers 1 to 5, and

[0024] However, if a1 and a2 are 1, L1 and L2 are single bonds, and n1 is 1, Ar1 is not a fluorene group, and

[0025] The above-mentioned substituted C5-C 60 Carbocyclic group, substituted C1-C 60 Heterocyclic group, substituted C1-C 30 Heterocyclic group, substituted C1-C 60 Alkyl groups, substituted C2-C 60 alkenyl group, substituted C2-C 60 alkynyl group, substituted C1-C 60 Alkoxy group, substituted C3-C 10 Cycloalkyl group, substituted C1-C 10 Heterocycloalkyl group, substituted C3-C 10 Cycloalkenyl group, substituted C1-C 10 Heterocycloalkenyl group, substituted C6-C 60 Aryl group, substituted C7-C 60 alkylaryl group, substituted C6-C 60 aryloxy group, substituted C6-C 60 Arylthio group, substituted C1-C 60 Heteroaryl group, substituted C2-C 60 Alkyl heteroaryl group, substituted C1-C 60 Heteroaryloxy group, substituted C1-C 60At least one of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituent of the substituted monovalent non-aromatic heterocondensed polycyclic group is,

[0026] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, -NCS, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group and C1-C 60 Alkoxygenation;

[0027] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, -NCS, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ) and -C(=O)(Q 11 C1-C substituted with at least one selected from ) 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group and C1-C 60 Alkoxygenation;

[0028] C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, and C1-C 10 Heterocycloalkenyl group;

[0029] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ) and -C(=O)(Q 21 C3-C substituted with at least one selected from ) 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, and C1-C 10 Heterocycloalkenyl group; and

[0030] -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ) and -C(=O)(Q 31 );

[0031] Selected from among,

[0032] The above Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 They are independently hydrogen, deuterium, C1-C 20 Alkyl group, C1-C 20Selected from alkoxy groups, phenyl groups and biphenyl groups, and

[0033] * is a bonding site with a neighboring atom.

[0034] According to another aspect, a composition is provided comprising one or more condensed ring compounds represented by the above chemical formula 1.

[0035] According to another aspect, an organic light-emitting device is provided comprising: a first electrode; a second electrode; and an organic layer interposed between the first electrode and the second electrode and including a light-emitting layer, and comprising one or more condensed ring compounds represented by the chemical formula 1. Effects of the invention

[0036] The above condensed ring compound has a low glass transition temperature and high solubility, and accordingly, the pot life of a solution containing the compound is extended, making it suitable for use in solution coating methods.

[0037] In addition, an organic light-emitting device containing the above-mentioned condensed ring compound can provide high luminous efficiency and a long lifespan. Brief explanation of the drawing

[0038] FIG. 1 is a diagram illustrating an exemplary energy level relationship between a condensed ring compound represented by Formula 1 and a first compound comprising a carbazole group in a composition according to one embodiment. FIG. 2 is a diagram illustrating an exemplary energy level relationship between a condensed ring compound represented by Formula 1 and a second compound containing an azine group in a composition according to one embodiment. FIG. 3 is a diagram illustrating exemplary energy level relationships between a condensed ring compound represented by Formula 1, a second compound containing an azine group, and a phosphorescent platinum group metal complex in a composition according to one embodiment. FIG. 4 is a diagram illustrating exemplary energy level relationships between a condensed ring compound represented by Formula 1, a first compound containing a carbazole group, a second compound containing an azine group, and a phosphorescent platinum group metal complex in a composition according to one embodiment. FIG. 5 is a cross-sectional view schematically showing an organic light-emitting device according to one embodiment. Specific details for implementing the invention

[0039] Unless otherwise defined in this specification, operations and measurements of physical properties, etc. are carried out under conditions of room temperature (20 to 25°C) / relative humidity 40 to 50% RH. Additionally, in this specification, "compound for organic light-emitting devices" may be referred to as "compound," "material for organic light-emitting devices" may be referred to as "material," and "composition for organic light-emitting devices" may simply be referred to as "composition."

[0040] Condensed ring compounds

[0041] A condensed ring compound represented by the following chemical formula 1 according to one embodiment of the present invention is described:

[0042] <Chemical Formula 1>

[0043]

[0044] <Chemical Formula 2>

[0045]

[0046] Among the above chemical formulas 1 and 2, L1 to L2 and L 11 C5-C pairs independently of each other, single-bonded, substituted, or unsubstituted 60 Carbocyclic groups, or substituted or unsubstituted C1-C 60 It is selected from heterocyclic groups.

[0047] For example, the above L1 to L2 and L 11are independently of each other, single bond, benzene group, pentylene group, indene group, naphthalene group, anthracene group, azulene group, heptylene group, acenaphthalene group, phenalene group, fluorene group, spiro-bifluorene group, benzoflurene group, dibenzoflurene group, phenanthrene group, biphenyl group, terphenyl group, triphenylene group, fluoranthene group, pyrene group, chrysene group, fisene group, perylene group, pentapene group, pentacene group, tetraphenyl group, hexaphenyl group, hexacene group, rubicene group, trinaphthalene group, heptaphenyl group, pyrantrene group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazolin group, naphthiridine group, acridine Group, Phenazine Group, Benzoquinoline Group, Benzoisoquinoline Group, Phenanthridine Group, Phenanthroline Group, Benzoquinone Group, Coumarin Group, Anthraquinone Group, Fluorenone Group, Furan Group, Tiene Group, Silol Group, Benzofuran Group, Benzotiene Group, Benzocilol Group, Dibenzofuran Group, Dibenzothiophene Group, Dibenzocilol Group, Pyrrole Group, Indole Group, Isoindole Group, Carbazole Group, Benzocarbazole Group, Dibenzocarbazole Group, Imidazole Group, Benzimidazole Group, Pyrazol Group, Triazole Group, Tetrazole Group, Indazole Group, Oxazole Group, Isoxazole Group, Benzooxazole Group, Benzisoxazole Group, Thiazole Group, Isothiazole Group, Benzothiazole Group, Benzisothiazole Group, Imidazopyridine Group, Imidazopyrimidine group, imidazophenanthridine group, benzimidazofenanthridine group, azadibenzofuran group, azacarbazole group, azadibenzodiene group, diazadibenzofuran group, diazcarbazole group, diazadibenzodiene group, xantone group and thioxantone group; and

[0048] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, C1-C 30Alkyl group, C1-C 30Alkoxy group, phenyl group, penthalenyl group, indenyl group, naphthyl group, anthracenyl group, azulenyl group, hepthalenyl group, acenaphthyl group, phenalenyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, biphenyl group, terphenyl group, triphenylenyl group, fluoranthenyl group, pyrenyl group, chrysenyl group, fisenyl group, perylenyl group, pentaphenyl group, pentacenyl group, tetraphenyl group, hexaphenyl group, hexacenyl group, rubisenyl group, trinaphthyl group, heptaphenyl group, pyrantrenyl group, pyridinyl group, pyrazinyl group, pyridazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, Quinoxalinyl group, quinazolinyl group, naphthiridinyl group, acrridinyl group, phenazinyl group, benzoquinolinyl group, benzisoquinolinyl group, phenanthridinyl group, phenanthrolinyl group, benzoquinoneyl group, coumarinyl group, anthraquinoneyl group, fluorenoneyl group, furanyl group, thienyl group, silolyl group, benzofuranyl group, benzothienyl group, benzocilolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzocilolyl group, pyrroleyl group, indoleyl group, isoindoleyl group, carbazoleyl group, benzocarbazoleyl group, dibenzocarbazoleyl group, imidazoleyl group, benzimidazoleyl group, pyrazolyl group, triazoleyl group, tetrazoleyl group, indazoleyl group, oxazolyl group, Isoxazole yl group, benzoxazole yl group, benzisoxazole yl group, thiazole yl group, isothiaazole yl group, benzothiaazole yl group, benzisothiazole yl group, imidazopyridinyl group, imidazopyrimidinyl group, imidazophenantridinyl group, benzimidazopenantridinyl group, azadibenzofuranyl group, azacarbazole yl group, azadibenzothienyl group, diazadibenzofuranyl group, diazcarbazole yl group, diazadibenzothienyl group, xantone yl group and thioxantone yl group substituted with at least one selected from benzene group, pentylene group, indene group, naphthalene group, anthracene group, azulene group, heptylene group, acenaphthalene group, phenalene group, fluorene group, spiro-bifluorene group, benzofuren group, Dibenzofluorene group, phenanthrene group, biphenyl group, terphenyl group, triphenylene group, fluoranthene group, pyrene group, chrysene group, fisene group, perylene group, pentafene group,Pentacene group, tetraphenyl group, hexaphenyl group, hexacene group, rubicene group, trinaphthalene group, heptaphenyl group, pyranthrene group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazolin group, naphthiridine group, acridine group, phenazine group, benzoquinoline group, benzisoquinoline group, phenanthridine group, phenanthroline group, benzoquinone group, coumarin group, anthraquinone group, fluorenone group, furan group, thiene group, silol group, benzofuran group, benzodiene group, benzocilol group, dibenzofuran group, dibenzothiophene group, dibenzocilol group, pyrrole group, indole group, isoindole group, carbazole group, It may be selected from the benzocarbazole group, dibenzocarbazole group, imidazole group, benzimidazole group, pyrazol group, triazole group, tetrazole group, indazole group, oxazole group, isoxazole group, benzoxazole group, benzisoxazole group, thiazole group, isothiaazole group, benzothiaazole group, benzisothiazole group, imidazopyridine group, imidazopyrimidine group, imidazophenantridine group, benzimidazopenantridine group, azadibenzofuran group, azacarbazole group, azadibenzodiene group, diazadibenzofuran group, diazcarbazole group, diazadibenzodiene group, xantone group, and thioxantone group.

[0049] For example, the above L1 to L2 and L 11 are independently of each other, a single bond, a benzene group, a biphenyl group, a terphenyl group, and a tetraphenyl group; and

[0050] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, C1-C 30 Alkyl group, C1-C 30It may be selected from a benzene group, a biphenyl group, a terphenyl group, and a tetraphenyl group, which are substituted with at least one selected from an alkoxy group, a phenyl group, a biphenyl group, and a terphenyl group.

[0051] For example, the above L1 to L2 and L 11 The groups may be independently a single bond and a group represented by the following chemical formulas 3-1 to 3-7:

[0052]

[0053] Among the above chemical formulas 3-1 to 3-7,

[0054] Z 31 To Z 33 They are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, C1-C 20 Alkyl group, C1-C 20 Alkoxy group, phenyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, and -Si(Q 31 )(Q 32 )(Q 33 Selected from ),

[0055] d4 is an integer from 0 to 4, and

[0056] Q 31 to Q 33 They are independently hydrogen, deuterium, C1-C 20 Alkyl group, C1-C 20 Selected from alkoxy groups, phenyl groups and biphenyl groups, and

[0058] ** and *' are bonding sites with neighboring atoms.

[0059] Among the above chemical formulas 1 and 2, a1 to a2 and a11 are independently selected from integers 1 to 5. a1 is the number of groups represented by L1, and when a1 is 2 or more, the a1 L1s may be identical or different from each other; a2 is the number of groups represented by L2, and when a2 is 2 or more, the a2 L2s may be identical or different from each other; and a11 is L 11 It is the number of groups represented by , and when a11 is 2 or more, a11 L 11 They may be the same or different from each other.

[0060] For example, the above a1 to a2 and a11 may be selected independently from integers 1 to 2, but are not limited thereto.

[0061] Among the above chemical formulas 1 and 2, Ar1 and Ar 11 C5-C5s are independently substituted or unsubstituted. 60 It is a carbocyclic group, provided that Ar1 is not a triphenylene group or a fluorene group connected at position 9.

[0062] For example, the above Ar1 and Ar 11 ...independently, phenyl group, penthalenyl group, indenyl group, naphthyl group, anthracenyl group, azulenyl group, hepthalenyl group, acenaphthyl group, phenalenyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, dibenzoflurenyl group, phenanthrenyl group, biphenyl group, terphenyl group, fluoranthenyl group, pyrenyl group, chrysenyl group, fisenyl group, perylenyl group, pentaphenyl group, pentacenyl group, tetraphenyl group, hexaphenyl group, hexacenyl group, rubisenyl group, trinaphthyl group, heptaphenyl group, and pyrantrenyl group; and

[0063] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, C1-C 30 Alkyl group, C1-C 30Substituted with at least one selected from alkoxy group, phenyl group, penthalenyl group, indenyl group, naphthyl group, anthracenyl group, azulenyl group, hepthalenyl group, acenaphthyl group, phenalenyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, dibenzoflurenyl group, phenanthrenyl group, biphenyl group, terphenyl group, fluoranthenyl group, pyrenyl group, chrysenyl group, fisenyl group, perylenyl group, pentaphenyl group, pentacenyl group, tetraphenyl group, hexaphenyl group, hexacenyl group, rubisenyl group, trinaphthyl group, heptaphenyl group, and pyrantrenyl group, phenyl group, penthalenyl group, indenyl group, naphthyl group, anthracenyl group, azulenyl group, hepthalenyl group, acenaphthyl group, It may be selected from phenalenyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, dibenzoflurenyl group, phenanthrenyl group, biphenyl group, terphenyl group, fluoranthenyl group, pyrenyl group, chrysenyl group, fisenyl group, perylenyl group, pentaphenyl group, pentacenyl group, tetraphenyl group, hexaphenyl group, hexacenyl group, rubisenyl group, trinaphthyl group, heptaphenyl group, and pyrantrenyl group.

[0064] For example, the above Ar1 and Ar 11 are independently of each other, phenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, biphenyl group, terphenyl group, and tetraphenyl group; and

[0065] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, C1-C 30 Alkyl group, C1-C 30 A phenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, biphenyl group, terphenyl group, and tetraphenyl group substituted with at least one selected from alkoxy group, phenyl group, biphenyl group, and terphenyl group; may be selected from these.

[0066] For example, the above Ar1 and Ar 11 The groups may be independently represented by the following chemical formulas 4-1 to 4-9:

[0067]

[0068] Among the above chemical formulas 4-1 to 4-9,

[0069] Y 41 is C(Z 45 )(Z 46 ) and,

[0070] Z 41 To Z 46 They are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, C1-C 20 Alkyl group, C1-C 20 Alkoxy group, phenyl group, and -Si(Q 31 )(Q 32 )(Q 33 Selected from ),

[0071] e3 is an integer from 0 to 3, and

[0072] e4 is an integer from 0 to 4, and

[0073] e5 is an integer from 0 to 5, and

[0074] e7 is an integer from 0 to 7, and

[0075] Q 31 to Q 33 They are independently hydrogen, deuterium, C1-C 20 Alkyl group, C1-C 20 Selected from alkoxy groups, phenyl groups and biphenyl groups, and

[0076] * is a bonding site with a neighboring atom.

[0077] For example, the above The moiety represented by may be a group represented by the following chemical formulas 5-1 to 5-22, but is not limited thereto:

[0078]

[0079]

[0080]

[0081]

[0082] Among the above chemical formulas 5-1 to 5-22,

[0083] Y 51 is C(Z 58 )(Z 59 ) and,

[0084] Z 51 To Z 59 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, C1-C 20 Alkyl group, C1-C 20 Alkoxy group, phenyl group, and -Si(Q 31 )(Q 32 )(Q 33 Selected from ),

[0085] f3 is an integer from 0 to 3, and

[0086] f4 is an integer from 0 to 4, and

[0087] f5 is an integer from 0 to 5, and

[0088] f7 is an integer from 0 to 7, and

[0089] Q 31 to Q 33 They are independently hydrogen, deuterium, C1-C 20 Alkyl group, C1-C 20 Selected from alkoxy groups, phenyl groups and biphenyl groups, and

[0090] * is a bonding site with a neighboring atom.

[0091] In the above chemical formulas 1 and 2, R1 to R6 are independently of each other a group represented by chemical formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, or a substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C7-C 60 Alkyl aryl groups, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 Heteroaryl group, substituted or unsubstituted C2-C 60 Alkyl heteroaryl group, substituted or unsubstituted C1-C 60 Heteroaryloxy groups, substituted or unsubstituted C1-C 60 Selected from a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -Si(Q1)(Q2)(Q3) and -N(Q1)(Q2), and

[0092] b3, b5, and b6 are independently selected from integers 0 to 4, and

[0094] *b2 is selected from integers 0 to 3, and

[0095] Any two adjacent groups among R1, R2, b3, b4, b5, and b6 are optionally combined to form a substituted or unsubstituted C5-C 30 Carbocyclic groups or substituted or unsubstituted C1-C 30 It can form heterocyclic groups.

[0096] For example, the above R1 to R6 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 Alkyl group, C2-C 20 alkenyl group, C2-C 20 alkynyl group, C1-C 20Alkoxy groups, phenyl groups, and naphthyl groups; and C1-C groups substituted with one or more selected from deuterium, -F, -Cl, -Br, -I, cyano groups, phenyl groups, biphenyl groups, and terphenyl groups. 20 Alkyl group, C2-C 20 alkenyl group, C2-C 20 alkynyl group, C1-C 20 It can be selected from alkoxy groups, phenyl groups, and naphthyl groups.

[0097] For example, the above R1 to R2 are independently hydrogen, C1-C 20 Alkyl groups, phenyl groups, and naphthyl groups; and C1-C groups substituted with one or more selected from deuterium, -F, -Cl, -Br, -I, cyano groups, phenyl groups, biphenyl groups, and terphenyl groups. 20 It can be selected from alkyl groups, phenyl groups, and naphthyl groups.

[0098] For example, the above R3 to R6 are independently hydrogen, C1-C 20 It may be an alkyl group or a phenyl group.

[0099] For example, any two adjacent groups among R1, R2, b3, b4, b5, and b6 are optionally combined to form C5-C 30 Carbocyclic group or C1-C 30 When forming a heterocyclic group, the above C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic groups do not contain substituents other than hydrogen.

[0100] Among the above chemical formulas 1 and 2, n1 is an integer from 1 to 5.

[0101] For example, the above n1 can be 1 or 2.

[0102] According to one embodiment, the group represented by Chemical Formula 1 can be represented by the following Chemical Formula 1A:

[0103] <Chemical Formula 1A>

[0104]

[0105] Among the above chemical formula 1A,

[0106] The descriptions of L1 to L2, a1 to a2, Ar1, R1 to R6, b3 to b6 and n1 refer to those defined above.

[0107] According to another embodiment, the condensed ring compound represented by Formula 1 may be a group represented by any one of the following Formulas 1-1 to 1-8:

[0108] <Chemical Formula 1-1>

[0109]

[0110] <Chemical Formula 1-2>

[0111]

[0112] <Chemical Formula 1-3>

[0113]

[0114] <Chemical Formula 1-4>

[0115]

[0116] <Chemical Formula 1-5>

[0117]

[0118] <Chemical Formula 1-6>

[0119]

[0120] <Chemical Formula 1-7>

[0121]

[0122] <Chemical Formula 1-8>

[0123]

[0124] Among the above chemical formulas 1-1 to 1-8,

[0125] The descriptions of L1 to L2, a1 to a2, Ar1, R3 to R6, b3 to b6 and n1 refer to those defined above, and

[0126] Z1 and Z2 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, C1-C 20 Alkyl group, C1-C 20 Alkoxy group, phenyl group, and -Si(Q 31 )(Q 32 )(Q 33 Selected from ),

[0127] c4 is an integer from 0 to 4, and

[0128] c7 is an integer from 0 to 7, and

[0129] c8 is an integer from 0 to 8, and

[0130] Q 31 to Q 33 They are independently hydrogen, deuterium, C1-C 20 Alkyl group, C1-C 20 It is selected from alkoxy groups, phenyl groups and biphenyl groups.

[0131] For example, the condensed ring compound represented by the above chemical formula 1 may not include an ortho-phenyl group, but is not limited thereto.

[0132] For example, the condensed ring compound represented by the above chemical formula 1 may contain six or fewer m-phenyl moiety groups.

[0133] For example, the condensed ring compound represented by the above chemical formula 1 may not contain heteroatoms, but is not limited thereto.

[0134] For example, the condensed ring compound represented by the above chemical formula 1 may have an asymmetric structure with different left and right sides centered on the fluorene group, but is not limited thereto.

[0135] For example, the glass transition temperature (T) of a condensed ring compound represented by the above chemical formula 1 g ) may be 140℃ or lower. For example, T of the above condensed ring compound gIt is not specifically limited, but may be 130°C or lower, 60°C or higher, or 100°C or higher.

[0136] In another embodiment, the condensed ring compound represented by Formula 1 may be selected from the following compounds 1 to 60, but is not limited thereto:

[0137]

[0138]

[0139]

[0140] .

[0141] For example, the above condensed ring compound may be selected from the above compounds 43 or 44, but is not limited thereto.

[0142] The condensed ring compound represented by Chemical Formula 1 above comprises a carbazole group or an indolocarbazole group having a substituent at the 2nd position and a p-terphenyl group. The p-terphenyl group has substituents at both ends, and at least one substituent is present at the meta position of the p-terphenyl group. Additionally, the substituent included in the p-terphenyl group has at least one m-phenyl group.

[0143] These configurations increase the number of possible conformations (conformation patterns), making it difficult for molecules to aggregate. Consequently, the glass transition temperature is lowered, and crystallization becomes less likely. As a result, it possesses high solubility, making it difficult to precipitate from solution and extending the pot life of the solution.

[0144] Furthermore, due to the relatively low glass transition temperature during the drying process for solvent removal, compound molecules within the film containing the compound undergo thermal motion relatively easily. Consequently, voids through which volatile impurity molecules pass are prone to form, facilitating the diffusion and removal of these molecules. As a result, the luminous efficiency and lifetime of the organic light-emitting diode are improved.

[0145] The above condensed ring compound has a good balance between HOMO / LUMO levels and electron and hole carrier mobilities. As a result, the charge recombination portion and exciton generation portion within the layer containing the above condensed ring compound are dispersed, and the load is also dispersed, so the lifespan of the organic light-emitting device is improved.

[0146] Additionally, optionally, the condensed ring compound includes a phenyl group or a naphthyl group as Ar1, thereby having a low glass transition temperature (T g Since it has high triplet excitation energy, it can improve luminous efficiency and luminous lifetime, and can promote the removal of volatile impurities in the drying process.

[0147] The above T g For example, it can be 50°C to 120°C, for example, 60°C to 110°C, or for example, 60°C to 100°C.

[0148] The above triplet excitation energy can be, for example, 2.4 eV or higher, for example, 2.5 eV or higher, for example, 2.6 eV or higher.

[0149] In addition, in the above condensed ring compound, if a1 and a2 are 1, L1 and L2 are single bonds, and n1 is 1, Ar1 is not a fluorene group. Through this, even though the number of possible conformations is relatively small, the interaction between condensed rings with large π-planes is reduced, making it difficult for molecules to aggregate, extending the pot life of the solution, or lowering the glass transition temperature, thereby promoting the removal of volatile impurities during the drying process and improving the luminescence lifetime.

[0150] In addition, the above-mentioned condensed ring compound does not include a fluorene group connected to the 9th position. Here, the 9th position refers to the part indicated by the dotted line among the following fluorene groups.

[0151]

[0152] Since the fluorene group connected to the 9th position does not have a π-coupling effect, it does not form an electronic conduction level of LUMO or close to LUMO, and there is only a possibility that the glass transition temperature will increase. In other words, if a fluorene group connected to the 9th position is included, there is a problem that it is difficult to remove volatile impurities and the luminescence lifetime is shortened.

[0153] The above condensed ring compound contains two or more meta-phenyl moiety groups. As a result, the number of conformations the molecule can have increases, and aggregation due to intermolecular interactions can be further reduced.

[0154] For example, the condensed ring compound represented by the above chemical formula 1 may contain six or fewer m-phenyl moiety groups. Accordingly, the glass transition temperature can be prevented from being lowered more than necessary.

[0155] The condensed ring compound represented by Chemical Formula 1 above optionally does not contain heteroatoms. If the condensed ring compound contains heteroatoms, at least one energy level among HOMO and LUMO changes, and the injection or transport of charges (holes or electrons) tends to become stronger, causing localized loading to concentrate at the interface between the emissive layer and the adjacent layer, which may shorten the luminescence lifetime.

[0156] The condensed ring compound represented by the above chemical formula 1 optionally does not contain an o-terphenyl group. This allows for an improved luminescence lifetime.

[0157] The condensed ring compound represented by the above chemical formula 1 may be included in an organic layer disposed between a pair of electrodes of an organic light-emitting device. For example, the condensed ring compound represented by the above chemical formula 1 may be included in a light-emitting layer and may be suitable as a host.

[0158] The condensed ring compound represented by Chemical Formula 1 above can provide high luminous efficiency and luminous lifetime of an organic light-emitting device. This is thought to be because, as previously mentioned, the condensed ring compound represented by Chemical Formula 1 has a good balance between a low glass transition temperature, LUMO levels, and electron and hole carrier mobilities.

[0159] In addition, the condensed ring compound represented by Chemical Formula 1 is difficult to precipitate from solution and has a long pot life of the solution. Therefore, the condensed ring compound can provide high luminous efficiency and luminous lifetime of an organic light-emitting device even when using a wet film deposition method.

[0160] The condensed ring compound represented by Chemical Formula 1 above can be synthesized using known organic synthesis methods. For example, the condensed ring compound represented by Chemical Formula 1 above can be synthesized by the Suzuki-Miyaura coupling reaction, etc. A person skilled in the art can easily understand the specific synthesis method of the condensed ring compound represented by Chemical Formula 1 by referring to the examples described below.

[0161] composition

[0162] Hereinafter, a composition according to one embodiment of the present invention will be described in detail.

[0163] The above composition may include one or more of the aforementioned condensed ring compounds.

[0164] The above condensed ring compound may be included in an organic layer disposed between a pair of electrodes of an organic light-emitting device. For example, the condensed ring compound represented by Chemical Formula 1 may be included in the light-emitting layer and may be suitable as a host.

[0165] The above condensed ring compound can provide high luminous efficiency and luminous lifetime of an organic light-emitting device. This is thought to be because, as mentioned above, the condensed ring compound represented by Chemical Formula 1 has a good balance between a low glass transition temperature, LUMO levels, and electron and hole carrier mobilities.

[0166] In addition, the above condensed ring compound is difficult to precipitate from a solution and has a long pot life of the solution. Therefore, the above condensed ring compound can provide high luminous efficiency and luminous lifetime of an organic light-emitting device even when using a wet film deposition method.

[0167] For example, the above composition may further include a first compound comprising a carbazole-based moiety.

[0168] For example, the above composition may further include a second compound comprising an azine-based moiety.

[0169] For example, the above composition may further include a light-emitting material.

[0170] For example, the above composition may further include one or more of a first compound comprising a carbazole-based moiety, a second compound comprising an azine-based moiety, and a luminescent material.

[0171] For example, the content of the condensed ring compound in the above composition may be 5 to 95 weight% based on the total weight of the above composition, for example, 10 to 90 weight%, or for example, 20 to 80 weight%.

[0172] Within the above range, the solubility of the condensed ring compound is further improved, and precipitation in the solution is less likely to occur, thereby extending the pot life of the solution. In addition, the luminous efficiency and luminous lifetime of the organic light-emitting device are improved.

[0173] Below, the above-mentioned luminescent material and the first to second compounds are described in detail.

[0174] The first compound described above includes a carbazole moiety as previously mentioned. That is, the composition according to one embodiment of the present invention contains a carbazole moiety to further enhance the effect of inhibiting molecular aggregation and can also improve the balance of electron and hole carrier mobilities. Consequently, the solubility of the composition is further improved, and precipitation in the solution becomes less likely to occur, thereby extending the pot life of the solution. Furthermore, the luminous efficiency and luminous lifetime of the organic light-emitting diode are further improved.

[0175] For example, the above composition may further include one or more selected from a first compound represented by the following chemical formula 9 and a second compound represented by the following chemical formula 10:

[0176] <Chemical Formula 9>

[0177]

[0178] <Chemical Formula 10>

[0179]

[0180] Among the above chemical formulas 9 and 10,

[0181] X 51 is N or C(R 51 ) and; X 52 is N or C(R 52 ) and; X 53 is N or C(R 53 ) and; X 54 is N or C(R 54 ) and; X 55 is N or C(R 55 ) and; X 56 is N or C(R 56 ) and; X 57 is N or C(R 57 ) and; X 58 is N or C(R 58 ) and;

[0182] X 61 is N or C(R 61 ) and; X 62 is N or C(R 62 ) and; X 63 is N or C(R 63 ) and; X 64 is N or C(R 64 ) and; X 65 is N or C(R 65 ) and; X 66 is N or C(R 66 ) but, X 61 To X 66 At least one of them is N and;

[0183] R 51 to R 58 and R 61 to R 66 They are independently hydrogen, deuterium, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C1-C 60 Selected from a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group;

[0184] R 59 is substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C1-C 60 Selected from a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group;

[0185] R 61 to R 66 At least one of the C6-C6 is substituted or unsubstituted 60 Aryl groups, substituted or unsubstituted C1-C 60 It is selected from a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group.

[0186] For example, among the above chemical formulas 9 and 10, R 51 to R 58 and R 61 to R 66 Two adjacent units may optionally combine to form a ring, but are not limited to this.

[0187] The first compound represented by the above chemical formula 9 can be represented, for example, by the following chemical formula 9-1:

[0188] <Chemical Formula 9-1>

[0189]

[0190] In the above chemical formula 9-1,

[0191] A 71 The ring is a substituted or unsubstituted C6-C 60 Carbocyclic groups or substituted or unsubstituted C1-C 60 It is a heterocyclic group, and

[0192] R 71 to R 74 are independently hydrogen, deuterium, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C1-C 60Selected from a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group;

[0193] b71 and b72 are independently selected from integers 0 to 4.

[0194] The first compound represented by the above chemical formula 9 can be represented, for example, by the following chemical formula 9-2:

[0195] <Chemical Formula 9-2>

[0196]

[0197] Of the above chemical formula 9-2,

[0198] L 81 C6-C with single bonds, substituted, or unsubstituted bonds 60 Aryl groups, substituted or unsubstituted C1-C 60 Selected from a heteroaryl group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group;

[0199] a81 is an integer selected from 1 to 5, and

[0200] R 81 to R 86 They are independently hydrogen, deuterium, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C1-C 60 Selected from a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group;

[0201] b81 and b83 are independently selected from integers 0 to 4, and

[0202] b82 and b84 are independently selected from integers 0 to 4.

[0203] For example, the first compound may be selected from compounds represented by the following chemical formulas H1-1 to H1-13, H2-1 to H2-34, and H3-1 to H3-3:

[0204]

[0205]

[0206]

[0207]

[0208]

[0209] .

[0210] The first compound comprising a carbazole-based moiety other than the compound represented by Chemical Formula 9 above is not limited to the specific example compounds above. For example, the present invention may be applied by referring to known carbazole derivatives described in paragraphs

[0095] to

[0104] of U.S. Patent Publication No. US2016 / 009388, Japanese Patent Publication No. 2014-509067, etc. Furthermore, carbazole derivatives described in these reference documents may be used as a basis for amendments to the present specification.

[0211] For example, the second compound may be selected from compounds represented by the following chemical formulas Az1 to Az38:

[0212]

[0213]

[0214]

[0215] The first compound has the shallowest HOMO (Highest Occupied Molecular Orbital) level among the compounds included in the composition, excluding the luminescent material (dopant). Therefore, the first compound has high hole injection and / or hole transport properties.

[0216] Accordingly, by adjusting the proportion of the first compound within the composition, the hole injection and / or hole transport properties of the composition can be controlled. This allows for easy control of the amount of holes in the light-emitting layer of an organic light-emitting device employing the composition and the hole density profile along the thickness direction of the light-emitting layer.

[0217] If the above composition further comprises the first compound, the HOMO level (HOMO0) of the condensed ring compound represented by Chemical Formula 1 and the HOMO level (HOMO) of the first compound Cz The difference (ΔHOMO) (hole trap depth) can be calculated from the following mathematical formula (1). Here, HOMO0 and HOMO Cz All are negative.

[0218] [Mathematical Formula 1]

[0219] ΔHOMO= HOMO Cz -HOMO0

[0220] ΔHOMO is, for example, 0.05 eV to 1.0 eV, for example, 0.10 eV to 0.8 eV, and for example, 0.15 eV to 0.7 eV.

[0221] FIG. 1 is a diagram illustrating an exemplary energy level relationship between a condensed ring compound represented by Formula 1 and a first compound comprising a carbazole group in a composition according to one embodiment. Referring to FIG. 1, HOMO0 and HOMO Cz A desirable relationship can be determined. If within the above range, the luminous efficiency and luminous lifetime of the organic light-emitting device are further improved.

[0222] The second compound has the deepest LUMO (Lowest Unoccupied Molecular Orbita) level among the compounds included in the composition. Therefore, the second compound has high electron injection and / or electron transport properties.

[0223] Accordingly, by adjusting the proportion of the second compound within the composition, the electron injection and / or electron transport properties of the composition can be controlled. This allows for easy control of the amount of electrons within the light-emitting layer of an organic light-emitting device employing the composition and the electron density profile along the thickness direction of the light-emitting layer.

[0224] If the above composition further comprises the second compound, the LUMO level (LUMO0) of the condensed ring compound represented by Chemical Formula 1 and the LUMO level (LUMO) of the second compound Azine The difference (ΔLUMO) (electron trap depth) can be calculated from the following Equation 2. Here, LUMO0 and LUMO azine All are negative.

[0225] [Mathematical Formula 2]

[0226] ΔLUMO = LUMO0 - LUMO azine

[0227] ΔLUMO is, for example, 0.05 eV to 1.0 eV, for example, 0.05 eV to 0.5 eV, and for example, 0.05 eV to 0.3 eV.

[0228] FIG. 2 is a diagram illustrating an exemplary energy level relationship between a condensed ring compound represented by Formula 1 and a second compound containing an azine group in a composition according to one embodiment. Referring to FIG. 2, LUMO0 and LUMO azine A desirable relationship can be determined. If within the above range, the luminous efficiency and luminous lifetime of the organic light-emitting device are further improved.

[0229] When the above composition comprises the above condensed ring compound and the above first compound, the composition may have excellent hole injection and / or hole transport properties, and the composition may be used in the hole injection layer, hole transport layer and / or light-emitting layer of an organic light-emitting device.

[0230] When the above composition includes the condensed ring compound and the second compound, the composition may have excellent electron injection and / or electron transport properties, and the composition may be used in the electron injection layer, electron transport layer and / or light-emitting layer of an organic light-emitting device.

[0231] When the above composition comprises the condensed ring compound, the first compound, and the second compound, the composition may have excellent hole injection, hole transport, electron injection, and / or electron transport properties, and the composition may be used in the hole injection layer, hole transport layer, light-emitting layer, electron transport layer, and / or electron injection layer of an organic light-emitting device.

[0232] In one embodiment, the composition may include the first compound and the second compound, but is not limited thereto. When the composition includes both the first compound and the second compound, the control of holes and the control of electrons can be performed independently. Therefore, there may be high convenience in the process of optimizing the performance of an organic light-emitting device employing such a composition.

[0233] Among the above compositions, the condensed ring compound represented by Chemical Formula 1 may be a wide band gap host. Through this, the luminous efficiency and luminous lifetime of the organic light-emitting device can be further improved.

[0234] The above composition may further include a light-emitting material.

[0235] The above-mentioned luminescent material is not particularly limited as long as it has a luminescent function, but may be a fluorescent dopant, a phosphorescent dopant, a quantum dot, etc.

[0236] The above fluorescent dopant is a compound capable of emitting light from a singlet exciton, and may be, for example, perlene and its derivatives, rubrene and its derivatives, coumarin and its derivatives, 4-dicyanomethylene-2-(p-dimethylaminostyryl)-6-methyl-4H-pyran (DCM) and its derivatives, but is not limited thereto.

[0237] The above phosphorescent dopant is a compound capable of emitting light from triplet excitons and may be an organometallic compound. For example, the above phosphorescent dopant is an iridium complex such as bis[2-(4,6-difluorophenyl)pyridinate] picolinate iridium(III): FIrpic, bis(1-phenylisoquinoline)(acetylacetonate) iridium(III): Ir(piq)2(acac)), tris(2-phenylpyridine) iridium(III): Ir(ppy)3, and tris(2-(3-p-xylyl)phenyl)pyridine iridium(III)) (dopant), osmium It may be a complex, platinum complex, etc., but is not limited thereto.

[0238] For example, the phosphorescent dopant may be a phosphorescent platinum group metal complex. The platinum group metals collectively refer to ruthenium (Ru), rhodium (Rh), palladium (Pd), osmium (Os), iridium (Ir), and platinum (Pt). Among these, a phosphorescent iridium (Ir) complex and a platinum (Pt) complex may be more preferred.

[0239] For example, the phosphorescent dopant may have one or more ligands selected from the group consisting of the following chemical formulas L1 to L17.

[0240]

[0241]

[0242] Among the above chemical formulas L1 to L17,

[0243] X 11 To X 23 Each is independently C(R 21 ) or N and,

[0244] X 31 is B(R 22 ), N(R 22 ), P(R 22 ), O, S, Se, C=O, S=O, SO2, C(R 22 )(R 23 ), Si(R 22 )(R 23 ) and Ge(R 22 )(R 23 Selected from ),

[0245] R 21 to R 23 are independently hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C1-C 60 Heteroalkyl groups, substituted or unsubstituted C7-C 60 Arylalkyl groups, substituted or unsubstituted C1-C 60 Alkoxy groups, substituted or unsubstituted C6-C 60 Aryloxy group, amino group, silyl group, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C3-C 60 Cycloalkenyl group, substituted or unsubstituted C2-C 60 Heteroalkenyl group, substituted or unsubstituted C2-C 60alkynyl group, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C1-C 60 Selected from the group consisting of heteroaryl groups, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, nitrite groups, isonitrile groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphine groups, and combinations thereof;

[0246] R 21 to R 23 Any two adjacent groups can condense or combine to form a ring.

[0247] For example, the phosphorescent dopant may be selected from the compounds indicated by D1 to D143 below.

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256] .

[0257] The above phosphorescent dopant is not limited to the specific example compounds above, and may be incorporated into the present invention by referring to known phosphorescent platinum group metal complexes described, for example, in paragraphs

[0105] to

[0113] of U.S. Patent Publication No. 2016 / 0093808 and Japanese Patent Publication No. 2014-509067. In addition, phosphorescent platinum group metal complexes described in these reference documents may be used as a basis for amendments to the present specification.

[0258] The above quantum dots may be nanoparticles composed of a group II-VI semiconductor, a group III-V semiconductor, or a group IV-IV semiconductor. For example, the quantum dots include CdO, CdS, CdSe, CdTe, ZnO, ZnS, ZnSe, ZnTe, HgS, HgSe, HgTe, MgSe, MgS CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, GaN, GaP, GaAs, AlN, AlP, AlAs, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InPAs, InPSb, GaAlNP, SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, etc. may be used, but are not limited thereto. In addition, the diameter of the quantum dot is not particularly limited, but may be, for example, 1 nm to 20 nm. The quantum dot may have a single-core structure or a core-shell structure.

[0259] The content of the luminescent material in the above composition may be 0.5 to 50 parts by weight per 100 parts by weight of the condensed ring compound represented by Formula 1 that functions as a host material, for example, 1 to 30 parts by weight or less, and 2 to 25 parts by weight.

[0260] In addition, the content of the luminescent material of the above composition may be 0.5 to 50 parts by weight with respect to 100 parts by weight of the total weight of the condensed ring compound represented by Formula 1 functioning as a host material and the first compound and second compound described below, for example, 1 to 30 parts by weight or less, and 2 to 25 parts by weight.

[0261] Within the above range, the solubility of the composition is further improved, and precipitation in the solution is less likely to occur, thereby extending the pot life of the solution. In addition, the luminous efficiency and luminous lifetime of the organic light-emitting diode are improved.

[0262] For example, the above composition may include the condensed ring compound, the first compound, the second compound, and a luminescent material (phosphorescent dopant).

[0263] FIG. 3 is a diagram illustrating an exemplary energy level relationship between a condensed ring compound represented by Formula 1, a second compound containing an azine group, and a phosphorescent platinum group metal complex in a composition according to one embodiment, and FIG. 4 is a diagram illustrating an exemplary energy level relationship between a condensed ring compound represented by Formula 1, a first compound containing a carbazole group, a second compound containing an azine group, and a phosphorescent platinum group metal complex in a composition according to one embodiment.

[0264] As shown in FIG. 3, the LUMO(LUMO0) of the condensed ring compound represented by Chemical Formula 1 is generally the LUMO(LUMO0) of the second compound. azine It is shallower than ). In addition, the HOMO(HOMO0) of the condensed ring compound represented by the above chemical formula 1 is generally the HOMO(HOMO0) of the first compound. Cz It is deeper than ). Also, the hole mobility of the condensed ring compound represented by the above chemical formula 1 is generally lower than the hole mobility of the first compound.

[0265] Referring to Fig. 4, LUMO0 is generally LUMOazine It is shallower. Also, HOMO0 is generally HOMO Cz It is deeper. Also, the hole mobility of the condensed ring compound represented by the above chemical formula 1 is generally lower than the hole mobility of the above first compound.

[0266] Accordingly, it is presumed that when a composition comprising a condensed ring compound represented by the above chemical formula 1, a hole-transporting host material such as the first compound, an electron-transporting host material such as the second compound, and the above phosphorescent platinum group metal complex is included in a light-emitting layer, the following mechanism is exhibited.

[0267] First, in the organic layer composed of the above composition, the electrons are at the deepest LUMO azine It is trapped once. However, the trapped electron is detrapped by LUMO0 and resumes movement. Therefore, in the organic layer, the electron is LUMO azine It moves by the repetition of trap-detrap between LUMO0 and , and electron mobility decreases. This is the same as in the case of Fig. 3.

[0268] In addition, holes are HOMOs of phosphorescent metal complexes (HOMO MC It is trapped in ). And the trapped hole is HOMO Cz It is detrapped and resumes movement. In addition, a condensed ring compound represented by Chemical Formula 1 is present in the organic layer in a proportion greater than a certain amount.

[0269] The above composition may further include a solvent.

[0270] For example, the solvent may have a boiling point of 100°C or higher and 350°C or lower at 101.3 kPa (1 atm). For example, the boiling point of the solvent may be 150°C or higher and 320°C or lower, and for example, 180°C or higher and 300°C or lower.

[0271] The content of the solvent in the composition is not particularly limited. For example, the concentration of the condensed ring compound in the composition may be 0.05 wt% or more and 10 wt% or less, and for example, 0.1 wt% or more and 6 wt% or less. If the concentration of the condensed ring compound is within the above range, it is desirable in terms of solubility and makes it difficult for precipitation to occur in the solution, which is desirable in terms of improving the pot life of the solution.

[0272] For example, the concentration of the condensed ring compound and other compounds (e.g., the first compound, the second compound, the phosphorescent metal complex, etc.) in the composition may be 0.05 wt% or more and 10 wt% or less, and for example, 0.1 wt% or more and 6 wt% or less. Being within the above range is desirable in terms of solubility and makes it difficult for precipitation to occur in the solution, which is desirable in terms of improving the pot life of the solution.

[0273] The above solvent is not particularly limited, provided that it dissolves the condensed ring compound represented by Chemical Formula 1 and / or the first compound represented by Chemical Formula 9. For example, the solvent is octane, nonane, decane, undecane, dodecane, toluene, xylene, benzonitrile, 3-methylbenzonitrile, dimethylacetamide, N-methylpyrrolidone, N,N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphate triamide, phenylcyclohexane, tetrahydronaphthalene, ethylbenzene, n-propylbenzene, iso-propylbenzene, diethylbenzene, mesitylene, propylbenzene, n-butylbenzene, sec-butylbenzene, 1-phenylpentane, 2-phenylpentane, 3-phenylpentane, phenylcyclopentane, 2-ethylbiphenyl, 3-ethylbiphenyl, cyclohexylbenzene, dimethoxybenzene, 1,4-dioxane, 1,2-diethoxyethane, diethyleneglycol dimethylether, diethyleneglycol diethylether, ethoxybenzene, 3-methylanisole, m-dimethoxybenzene, 2-hexanone, 3-hexanone, cyclohexanone,2-heptanone, 3-heptanone, 4-heptanone, cycloheptanone, butyl acetate, butylpropionate, heptylbutyrate, propylene carbonate, anisole, ethoxytoluene, phenoxytoluene, isopropylbiphenyl, dimethylanisole, phenyl acetate, phenyl propionic acid, methyl benzoate, ethyl benzoate, 1-propylbenzoate, 1-butyl It may be benzoate (1-butylbenzoate), etc., but is not limited thereto.

[0274] Accordingly, the above composition can be used as a material for light-emitting devices (e.g., organic light-emitting devices, quantum dot light-emitting devices, etc.). Specifically, the above composition can be used in the light-emitting layer, charge injection layer, and / or charge transport layer of a light-emitting device. More specifically, the above composition can be used in the light-emitting layer of a light-emitting device. In particular, the above composition can be used when manufacturing a light-emitting device by a solution coating method, in which case the current efficiency and light-emitting lifetime of the light-emitting device can be maintained or improved.

[0275] Organic light-emitting diode

[0276] Hereinafter, an organic light-emitting device according to an embodiment of the present invention will be described in detail with reference to FIG. 5. FIG. 5 is a diagram showing a schematic cross-section of an organic light-emitting device according to an embodiment of the present invention.

[0277] An organic light-emitting element (100) according to one embodiment of the present invention comprises a substrate (110), a first electrode (120) disposed on the substrate (110), a hole injection layer (130) disposed on the first electrode (120), a hole transport layer (140) disposed on the hole injection layer (130), a light-emitting layer (150) disposed on the hole transport layer (140), an electron transport layer (160) disposed on the light-emitting layer (150), an electron injection layer (170) disposed on the electron transport layer (160), and a second electrode (180) disposed on the electron injection layer (170).

[0278] The condensed ring compound represented by Chemical Formula 1 above may be included in any one of the organic layers (e.g., hole injection layer (130), hole transport layer (140), light-emitting layer (150), electron transport layer (160), electron injection layer (170)) interposed between the first electrode (120) and the second electrode (180). Specifically, the condensed ring compound represented by Chemical Formula 1 above may be included in the light-emitting layer (150) as a host. Alternatively, the condensed ring compound represented by Chemical Formula 1 above may be included in an organic layer other than the light-emitting layer (150). For example, the condensed ring compound represented by Chemical Formula 1 above may be included in the hole injection layer (130) and / or the hole transport layer (140) as a charge transport material.

[0279] In this specification, "organic layer" is a term referring to a single and / or multiple layers interposed between a first electrode and a second electrode of an organic light-emitting device. The "organic layer" may include not only organic compounds but also organometallic compounds including metals.

[0280] In the present specification, the phrase “(the organic layer) comprises one or more organometallic compounds” may be interpreted as “(the organic layer) may comprise one condensed ring compound belonging to the category of Formula 1 or two or more different condensed ring compounds belonging to the category of Formula 1.”

[0281] For example, the organic layer may include only compound 1 as the condensed 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 include compound 1 and compound 2 as the condensed ring compound. In this case, compound 1 and compound 2 may be present in the same layer (for example, both compound 1 and compound 2 may be present in the light-emitting layer).

[0282] The substrate (110) may be a substrate used in general organic light-emitting devices. For example, the substrate (110) may be a glass substrate, silicon substrate, transparent plastic substrate, etc., which have excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance, but is not limited thereto.

[0283] A first electrode (120) is formed on a substrate (110). Specifically, the first electrode (120) is an anode and can be formed from a material with a high work function among metals, alloys, or conductive compounds to facilitate hole injection. The first electrode (120) may be a reflective electrode, a semi-transparent electrode, or a transparent electrode. The first electrode (120) may have a single layer or a multilayer structure including two or more layers. For example, the first electrode (120) may be a transparent electrode formed from materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO), which have excellent transparency and conductivity. The first electrode (120) may be formed as a reflective electrode by laminating magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. onto the transparent electrode. Alternatively, the first electrode (120) may have a three-layer structure of ITO / Ag / ITO, but is not limited thereto.

[0284] A hole transport region can be formed on the first electrode (120).

[0285] The above hole transport region may include at least one of a hole injection layer (130), a hole transport layer (140), an electron blocking layer (not shown), and a buffer layer (not shown).

[0286] The hole transport region may include only the hole injection layer (130) or only the hole transport layer (140). Alternatively, the hole transport region may have a structure of a hole injection layer / hole transport layer or a hole injection layer / hole transport layer / electron blocking layer stacked sequentially from the first electrode (120).

[0287] The hole injection layer (130) is, for example, poly(ether ketone)-containing triphenylamine (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl) borate (PPBI), N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), copper phthalocyanine, 4,4',4"-tris(3-methylphenylphenylamino) Triphenylamine (4,4',4"-tris(3-methylphenylphenylamino) triphenylamine: m-MTDATA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine: NPB), 4,4',4"-tris(diphenylamino) triphenylamine (4,4',4"-tris(diphenylamino) triphenylamine: TDATA), 4,4',4"-tris(N,N-2-naphthylphenylamino) triphenylamine (4,4',4"-tris(N,N-2-naphthylphenylamino) triphenylamine (2-TNATA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate): PEDOT / PSSIt may include at least one of polyaniline / 10-camphorsulfonic acid (PANI / CSA) and polyaniline / poly(4-styrenesulfonate) (PANI / PSS).

[0288] The hole injection layer (130) can be formed with a thickness of about 10 nm to about 1000 nm, more specifically about 10 nm to about 100 nm.

[0289] The hole transport layer (140) is, for example, a carbazole derivative such as 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), N-phenylcarbazole and polyvinylcarbazole, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA). It may include at least one of N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB) and poly(9,9-dioctyl-fluorene-co-N-(4-butylphenyl)-diphenylamine (TFB).

[0290] The hole transport layer (140) can be formed with a thickness of about 10 nm to about 1000 nm, more specifically about 10 nm to about 150 nm.

[0291] In addition to the material described above, the hole transport region may further include a charge-generating material to enhance conductivity. The charge-generating material may be uniformly or non-uniformly dispersed within the hole transport region.

[0292] The charge-generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of the p-dopant include quinone derivatives such as tetracyanoquinone dimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethane (F4-TCNQ); metal oxides such as tungsten oxide and molybdenum oxide; and cyano group-containing compounds such as the following compounds HT-D1, HT-D2, but are not limited thereto.

[0293]

[0294]

[0295] Meanwhile, if the hole transport region described above includes a buffer layer, the electron blocking layer material of the buffer layer may be selected from materials that can be used in the hole transport region described above and host materials described below, but is not limited thereto.

[0296] In addition, if the hole transport region includes an electron blocking layer, the electron blocking layer material may be selected from materials that can be used in the hole transport region as described above and host materials described below, but is not limited thereto. For example, if the hole transport region includes an electron blocking layer, mCP may be used as the electron blocking layer material.

[0297] A light-emitting layer (150) is formed on the hole transport region. The light-emitting layer (150) is a layer that emits light through fluorescence, phosphorescence, etc. The light-emitting layer (150) may include a host and / or a dopant, and the host may include a condensed ring compound represented by Chemical Formula 1. In addition, the host and dopant used in the light-emitting layer (150) may be known materials.

[0298] For example, the host is tris(8-quinolinato)aluminium (Alq3), 4,4'-bis(carbazol-9-yl)biphenyl (CBP), poly(n-vinylcarbazole): PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), and 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene: TPBi) 3-tert-butyl-9,10-di(naphth-2-yl)anthracene (3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), distyrylarylene (DSA), 4,4'-bis(9-carbazole)-2,2'-dimethyl-biphenyl (4,4'-bis(9-carbazole)-2,2'-dimethyl-bipheny (dmCBP), etc. may be included, but are not limited thereto.

[0299] Alternatively, the host may further include one or more of the aforementioned first and second compounds, but is not limited thereto.

[0300] For example, the above dopants are perlene and its derivatives, rubrene and its derivatives, coumarin and its derivatives, 4-dicyanomethylene-2-(p-dimethylaminostyryl)-6-methyl-4H-pyran (DCM) and its derivatives, bis[2-(4,6-difluorophenyl)pyridinate] picolinate iridium(III): FIrpic, bis(1-phenylisoquinoline)(acetylacetonate) iridium(III): Ir(piq)2(acac)), It may include, but is not limited to, iridium complexes such as tris(2-phenylpyridine) iridium(III): Ir(ppy)3, tris(2-(3-p-xylyl)phenyl)pyridine iridium(III) (dopant), osmium complexes, platinum complexes, etc.

[0301] When the above-mentioned light-emitting layer includes a host and a dopant, the content of the dopant can typically be 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.

[0302] The light-emitting layer (150) can be formed with a thickness of about 10 nm to about 60 nm.

[0303] When the above organic light-emitting device is a full-color organic light-emitting device, the light-emitting layer may be patterned into a red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer. Alternatively, various variations are possible, such as the light-emitting layer having a stacked structure of a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer to emit white light.

[0304] An electron transport region can be formed on the light-emitting layer (150).

[0305] The electron transport region may include at least one of a hole blocking layer (not shown), an electron transport layer (160), and an electron injection layer (170).

[0306] For example, the electron transport region may have a structure of a hole blocking layer / electron transport layer / electron injection layer or an electron transport layer / electron injection layer, but is not limited thereto. The electron transport layer may have a single layer or a multilayer structure including two or more different materials.

[0307] For example, the organic light-emitting device (100) may include a hole blocking layer between the electron transport layer (160) and the light-emitting layer (150) to prevent excitons or holes from diffusing into the electron transport layer (160). The hole blocking layer may include, for example, at least one of an oxadiazole derivative, a triazole derivative, BCP, Bphen, Balq, and the following HB1, but is not limited thereto.

[0308]

[0309]

[0310] The thickness of the hole blocking layer may be about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer satisfies the range described above, excellent hole blocking characteristics can be obtained without a substantial increase in driving voltage.

[0311] The electron transport layer (160) comprises: tris(8-quinolinato) aluminum (Alq3), Balq; a compound containing a pyridine ring such as 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene; and a compound containing a triazine ring such as 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine. Compounds containing an imidazole ring such as 2-(4-(N-phenylbenzimidazolyl-1-yl-phenyl)-9,10-dinaphthylanthracene); compounds containing a triazole ring such as TAZ and NTAZ; 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), and may include BCP, Bphen, etc.

[0312]

[0313] Alternatively, the electron transport layer (160) may include commercially available products such as KLET-01, KLET-02, KLET-03, KLET-10, KLET-M1 (the above, available from Chemipro Kasei).

[0314] The electron transport layer (160) may further include a metal-containing material in addition to the material described above.

[0316] The metal-containing material may include a Li complex. The Li complex may include, for example, the following compounds ET-D1 (lithium quinolate, LiQ) or ET-D2.

[0317]

[0318] The electron transport layer (160) can be formed with a thickness of, for example, about 15 nm to about 50 nm.

[0319] An electron injection layer (170) is formed on the electron transport layer (160).

[0320] The electron injection layer (170) may include, for example, lithium compounds such as (8-hydroxyquinolinato)lithium (Liq) and lithium fluoride (LiF), sodium chloride (NaCl), cesium fluoride (CsF), lithium oxide (Li2O), or barium oxide (BaO).

[0321] The electron injection layer (170) can be formed with a thickness of about 0.3 nm to about 9 nm.

[0322] A second electrode (180) is formed on the electron injection layer (170). Specifically, the second electrode (180) is a negative electrode and can be formed from a material with a small work function among metals, alloys, electrically conductive compounds, and combinations thereof. For example, the second electrode (180) can be formed as a reflective electrode using a metal such as lithium (Li), magnesium (Mg), aluminum (Al), calcium (Ca), or an alloy such as aluminum-lithium (Al-Li), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag). Alternatively, the second electrode (180) can be formed as a transparent electrode using a transparent conductive film such as a thin film of the metal or alloy with a thickness of 20 nm or less, indium tin oxide (In2O3-SnO2), and indium zinc oxide (In2O3-ZnO).

[0323] In addition, the stacked structure of the organic light-emitting element (100) according to one embodiment of the present invention is not limited to the examples described above. The organic light-emitting element (100) according to one embodiment of the present invention may be formed with other known stacked structures. For example, the organic light-emitting element (100) may omit one or more layers among the hole injection layer (130), hole transport layer (140), electron transport layer (160), and electron injection layer (170), and may additionally include other layers. In addition, each layer of the organic light-emitting element (100) may be formed as a single layer or as multiple layers.

[0324] The method of manufacturing each layer of the organic light-emitting element (100) according to one embodiment of the present invention is not particularly limited and can be manufactured by various methods such as, for example, vacuum deposition, solution coating, LB method, etc.

[0325] The above solution application method may include spin coating, casting, micro gravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing, flexographic printing, offset printing, inkjet printing, etc.

[0326] The solvents used in the solution application method are toluene, xylene, diethyl ether, chloroform, ethyl acetate, dichloromethane, tetrahydrofuran, acetone, acetonitrile, N,N-dimethylformamide, dimethyl sulfoxide, anisole, hexamethylphosphate triamide, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene, dioxane, cyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, methyl ethyl ketone, cyclohexanone, butyl acetate, ethyl cellosolve acetate, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, and diethoxy It may include methane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, methanol, ethanol, propanol, isopropanol, cyclohexanol, N-methyl-2-pyrrolidone, etc., but is not limited to those that can dissolve the material used to form each layer.

[0327] The concentration of the composition used in the solution coating method may be, specifically, 0.1 weight % or more to 10 weight % or less, more specifically 0.5 weight % or more to 5 weight % or less, taking into consideration coating properties, but is not limited thereto.

[0328] The above vacuum deposition method varies depending on the compound used, the structure of the target layer, and thermal properties, but for example, a deposition temperature of about 100 to about 500°C and a vacuum degree of about 10 -8 to about 10 -3 torr, deposition rate can be selected in the range of about 0.01 to about 100 Å / sec.

[0329] In one embodiment, the first electrode (120) may be an anode and the second electrode (180) may be a cathode.

[0330] For example, the first electrode (120) is an anode and the second electrode (180) is a cathode, and the organic layer includes a light-emitting layer (150) interposed between the first electrode (120) and the second electrode (180), and the organic layer further includes a hole transport region interposed between the first electrode (120) and the light-emitting layer (150) and an electron transport region interposed between the light-emitting layer (150) and the second electrode (180), the hole transport region includes at least one selected from a hole injection layer (130), a hole transport layer (140), a buffer layer, and an electron blocking layer, and the electron transport region may include at least one selected from a hole blocking layer, an electron transport layer (160), and an electron injection layer (170).

[0331] In another embodiment, the first electrode (120) may be a cathode and the second electrode (180) may be an anode.

[0332] The above organic light-emitting element has been described with reference to FIG. 5, but is not limited thereto.

[0333] [Explanation of Substituents]

[0334] In this specification, "X and Y are each independently" means that X and Y may be the same or different from each other.

[0335] In this specification, "substituted" is R 11 This means that the hydrogen atoms of the substituents can be further replaced by other substituents.

[0336] C1-C in this specification 24An alkyl group refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 24 carbon atoms, and specific examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a tert-pentyl group, a neopentyl group, a 1,2-dimethylpropyl group, an n-hexyl group, an isohexyl group, a 1,3-dimethylbutyl group, a 1-isopropylpropyl group, a 1,2-dimethylbutyl group, an n-heptyl group, a 1,4-dimethylpentyl group, a 3-ethylpentyl group, a 2-methyl-1-isopropylpropyl group, a 1-ethyl-3-methylbutyl group, an n-octyl group, a 2-ethylhexyl group, and a 3-methyl-1-isopropylbutyl group. Includes 2-methyl-1-isopropyl group, 1-tert-butyl-2-methylpropyl group, n-nonyl group, 3,5,5-trimethyldecyl group, n-decyl group, isodecyl group, n-undecyl group, 1-methyldecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-eicosyl group, n-heneicosyl group, n-docosyl group, n-tricosyl group, n-tetracosyl group, etc.

[0337] C1-C in this specification 24 The alkylene group is the C1-C 24 It refers to a divalent group having the same structure as an alkyl group.

[0338] C1-C in this specification 24 The alkoxy group is -OA 101 (Here, A 101 The above C1-C 24It refers to a monovalent group having the chemical formula of an alkyl group, and specific examples thereof include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, an n-pentoxy group, an isopentoxy group, a tert-pentoxy group, a neopentoxy group, an n-hexyloxy group, an isohexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group, a dodecyloxy group, a tridecyloxy group, a tetradecyloxy group, a pentadecyloxy group, a hexadecyloxy group, a heptadecyloxy group, an octadecyloxy group, a 2-ethylhexyloxy group, a 3-ethylpentyloxy group, etc.

[0339] C1-C in this specification 24 The alkyl thio group is -SA 102 (Here, A 102 The above C1-C 24 It refers to a monovalent group having the chemical formula of an alkyl group.

[0340] C3-C in this specification 30 A cycloalkyl group refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 30 carbon atoms that participates in ring formation, and specific examples thereof include cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, etc. In this specification, C3-C 30 The cycloalkylene group is the C3-C 30 It refers to a divalent group having the same structure as a cycloalkyl group.

[0341] C6-C in this specification 30 An aryl group refers to a monovalent group having a carbocyclic aromatic system with 6 to 30 carbon atoms that participates in ring formation (i.e., when substituted by a substituent, the atom included in the substituent is not included in the number of ring-forming carbon atoms), C6-C 30 An arylene group refers to a divalent group having a carbocyclic aromatic system with 6 to 30 carbon atoms. The above C6-C 30Specific examples of aryl groups include phenyl groups, naphthyl groups, anthracenyl groups, phenanthrenyl groups, pyrenyl groups, chrysenyl groups, etc. The above C6-C 30 Aryl group and C6-C 30 If the arylene group contains two or more rings, the two or more rings can be condensed together.

[0342] C6-C in this specification 30 The aryloxy group is -OA 103 (Here, A 103 The above C6-C 30 It refers to an aryl group. Specific examples thereof include a 1-naphthyloxy group, a 2-naphthyloxy group, a 2-azulenyloxy group, etc.

[0343] C6-C in this specification 30 Ariltiogi is -SA 104 (Here, A 104 is the above C6-C 30 It refers to Arilgiim).

[0344] C1-C in this specification 30 A heteroaryl group refers to a monovalent group comprising at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, and having a heterocyclic aromatic system having 1 to 30 carbon atoms participating in ring formation, and C1-C 30 A heteroarylene group refers to a divalent group comprising at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, and having a heterocyclic aromatic system having 1 to 30 carbon atoms participating in ring formation. The C1-C 30 Specific examples of heteroaryl groups include pyridinyl groups, pyrimidinyl groups, pyrazinyl groups, pyridazinyl groups, triazinyl groups, quinolinyl groups, isoquinolinyl groups, etc. The above C5-C 30 Heteroaryl group and C5-C 30 When a heteroarylene group contains two or more rings, the two or more rings can be condensed together.

[0345] C6-C in this specification 30 The heteroaryloxy group is -OA 105 (Here, A 105 The above C6-C 30 It refers to a heteroaryl group. Specific examples thereof include 2-furanyloxy group, 2-thienyloxy group, 2-indoleyloxy group, 3-indoleyloxy group, 2-benzofuryloxy group, 2-benzothienyloxy group, etc.

[0346] C6-C in this specification 30 Heteroaryltio groups -SA 106 (Here, A 106 is the above C6-C 30 It refers to a heteroaryl group.

[0347] C7-C in this specification 30 An arylalkyl group is a monovalent group in which an aryl group is substituted for an alkyl group, wherein the sum of the carbon atoms of the constituting alkyl and aryl groups is 7 to 30. The above C7-C 30 Specific examples of arylalkyl groups include benzyl groups, phenylethyl groups, phenylpropyl groups, naphthylmethyl groups, etc.

[0348] C6-C in this specification 30 The arylalkyloxy group is -OA 105 (Here, A 105 The above C7-C 30 It refers to an arylalkyl group.

[0349] C6-C in this specification 30 The arylalkylthio group is -SA 106 (Here, A 106 The above C7-C 30 It refers to an arylalkyl group.

[0350] C8-C in this specification 30 An aryl alkenyl group is a monovalent group in which an aryl group is substituted for an alkenyl group, and the sum of the carbon atoms of the alkenyl and aryl groups constituting it is 8 to 30.

[0352] C8-C in this specification 30An aryl-alkynyl group is an alkynyl group substituted with an aryl group, and refers to a monovalent group in which the sum of the carbon atoms of the constituting alkynyl group and aryl group is 8 to 30.

[0353] 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 together, and the entire molecule contains only carbon as a ring-forming atom and has non-aromaticity. Specific examples of the monovalent non-aromatic condensed polycyclic group include fluorenyl groups, etc. In this specification, a divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

[0354] In this specification, a monovalent 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 together, and the ring-forming atom includes a heteroatom selected from N, O, P, Si, and S in addition to carbon, and the entire molecule has non-aromaticity. The monovalent non-aromatic heterocondensed heteropolycyclic group includes a carbazole group, etc. In this specification, a divalent non-aromatic heterocondensed heteropolycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic heterocondensed heteropolycyclic group.

[0355] C5-C in this specification 30 A carbocyclic group refers to a saturated or unsaturated cyclic group having only 5 to 30 carbons as ring-forming atoms. The above C5-C 30 The carbocyclic group may be a monocyclic group or a polycyclic group, and depending on the chemical formula structure, it may be a monovalent, divalent, trivalent, tetravalent, pentavalent, or hexavalent group.

[0356] C1-C in this specification 30 A heterocyclic group refers to a saturated or unsaturated cyclic group having at least one heteroatom selected from N, O, P, Si, and S in addition to 1 to 30 carbons as ring-forming atoms. The above C1-C 30 A heterocyclic group may be a monocyclic group or a polycyclic group, and depending on the chemical formula structure, it may be a monovalent, divalent, trivalent, tetravalent, pentavalent, or hexavalent group.

[0357] The substituted C5-C in this specification 30 Carbocyclic group, substituted C1-C 30 Heterocyclic group, substituted C1-C 60 Alkyl groups, substituted C2-C 60 alkenyl group, substituted C2-C 60 alkynyl group, substituted C1-C 60 Alkoxy group, substituted C3-C 10 Cycloalkyl group, substituted C1-C 10 Heterocycloalkyl group, substituted C3-C 10 Cycloalkenyl group, substituted C1-C 10 Heterocycloalkenyl group, substituted C6-C 60 Aryl group, substituted C6-C 60 aryloxy group, substituted C6-C 60 Arylthio group, substituted C1-C 60 At least one of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituent of the substituted monovalent non-aromatic heterocondensed polycyclic group is,

[0358] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group and C1-C60 Alkoxygenation;

[0359] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q 11 )(Q 12 ), -Si(Q 13 )(Q 14 )(Q 15 ), -B(Q 16 )(Q 17 ) and -P(=O)(Q 18 )(Q 19 C1-C substituted with at least one of ) 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group and C1-C 60 Alkoxygenation;

[0360] C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic heterocondensed polycyclic group;

[0361] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q 21 )(Q 22 ), -Si(Q 23 )(Q 24 )(Q 25 ), -B(Q 26 )(Q 27 ) and -P(=O)(Q 28 )(Q 29 C3-C substituted with at least one of ) 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic heterocondensed polycyclic group; and

[0362] -N(Q 31 )(Q 32 ), -Si(Q 33 )(Q34 )(Q 35 ), -B(Q 36 )(Q 37 ) and -P(=O)(Q 38 )(Q 39 );

[0363] Selected from among,

[0364] The above Q1 to Q9, Q 11 to Q 19 , Q 21 to Q 29 and Q 31 to Q 39 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C1-C 60 Alkyl groups and C6-C 60 C6-C substituted with at least one aryl group 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 It is selected from a heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocondensed polycyclic group.

[0365] [etc]

[0366] In this specification, "A to B" means a range from A to B including A and B.

[0367] Although an embodiment of the present invention has been described above with reference to the attached drawings, the present invention is not limited to such embodiment. It is evident to those skilled in the art that various modifications or variations can be made within the scope of the technical concept described in the claims. Such various modifications and variations are also understood to fall within the technical scope of the present invention.

[0368] Hereinafter, with reference to examples and comparative examples, a condensed ring compound represented by Chemical Formula 1 and an organic light-emitting device containing the same will be described in detail. The examples described below are presented merely as examples, and the condensed ring compound and organic light-emitting device according to one embodiment of the present invention are not limited by the examples described below.

[0369] In the following synthesis examples, the amount of 'B' and the amount of 'A' used in the expression "'B' was used instead of 'A'" are the same based on molar equivalents.

[0370] Also, "%" is based on weight unless otherwise noted.

[0371] Examples

[0372] Synthesis Example 1: Synthesis of Compound 43

[0373]

[0374] Under a nitrogen atmosphere, 2-bromo-9,9-diphenyl-9H-fluorene (30 mmol, 11.92 g), 2-([1,1':3',1'' terphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (31.5 mmol, 11.22 g), toluene (120 ml), and EtOH (30 ml) were added to a 3-neck flask and dissolved by stirring.

[0375] Next, K2CO32M aq. (1.5 eq. 22.5 ml) was added, followed by the addition of palladium acetate (3 mol%, 0.9 mmol, 202 mg) and o-tolylphosphine (4.5 mol%, 1.35 mmol, 411 mg), and the mixture was stirred at 80°C for 8 hours.

[0376] It was cooled to room temperature, diluted with toluene (200 ml), filtered using Celite (registered trademark), and washed three times with pure water. It was dried with anhydrous magnesium sulfate and concentrated by filtering through a silica gel pad.

[0377] This was recrystallized twice in toluene:hexane (5 ml: 15 ml / 1 g) to obtain a white solid. The yield of compound 43 was 16.2 g, and the yield was 99%.

[0378] Synthesis Example 2: Synthesis of Compound 44

[0379] Synthesis of intermediate 44a

[0380]

[0381] Under a nitrogen atmosphere, 3-bromoiodobenzene (330 mmol, 93.36 g), 3-phenylboronic acid (1.0 eq. 300 mmol, 59.41 g), toluene (1500 ml), and EtOH (150 ml) were added to a 3-neck flask and dissolved by stirring.

[0382] Next, K2CO32M aq. (1.5 eq. 225 ml) was added, followed by the addition of Pd(PPh3)4 (3 mol%, 9 mmol, 10.40 g) and stirring at 70°C for 12 hours.

[0383] It was cooled to room temperature, filtered using Celite (registered trademark), and washed twice with pure water. It was dried with anhydrous magnesium sulfate and concentrated by filtering through a silica gel pad.

[0384] This was recrystallized twice in toluene:hexane (3 ml: 12 ml / 1 g) and vacuum dried (50°C, 12 hours) to obtain a white solid product. The yield of intermediate 44a was 58.4 g, and the yield was 63%.

[0385] Synthesis of intermediate 44b

[0386]

[0387] Under a nitrogen atmosphere, intermediate 44a (100 mmol, 30.92 g), 3-chlorophenylboronic acid (1.1 eq. 110 mmol, 17.20 g), toluene (200 ml) and EtOH (50 ml) were added to a 3-neck flask and dissolved by stirring.

[0388] Next, K2CO32M aq. (1.5 eq. 75 ml) was added, followed by the addition of Pd(PPh3)4 (3 mol%, 3 mmol, 3.47 g) and stirring at 70°C for 12 hours.

[0389] It was cooled to room temperature, diluted in 500 ml of toluene, filtered using Celite (registered trademark), and washed twice with pure water. It was dried with anhydrous magnesium sulfate and concentrated by filtering through a silica gel pad.

[0390] This was recrystallized once in toluene:hexane (3 ml: 12 ml / 1 g) and vacuum dried (50°C, 12 hours) to obtain a white solid product. The yield of intermediate 44b was 18.75 g, and the yield was 55%.

[0391] Synthesis of intermediate 44c

[0392]

[0393] Under a nitrogen atmosphere, intermediate 44b (55 mmol, 18.6 g), pinacollatodiborone (1.1 eq. 60.5 mmol, 15.36 g), potassium acetate (2 eq. 110 mmol, 10.8 g) and 1,4-dioxane (220 ml) were added to a 3-neck flask and dissolved by stirring.

[0394] Next, palladium acetate (2 mol%, 1.1 mmol, 247 mg) and X-Phos (4 mol%, 2.2 mmol, 1.05 g) were added and stirred at 100°C for 12 hours.

[0395] It was cooled to room temperature, diluted in 300 ml of toluene, filtered using Celite, and washed three times with pure water. It was dried with anhydrous magnesium sulfate and concentrated by filtering through a silica gel pad.

[0396] This was recrystallized twice in hexane (10 ml / 1 g) and vacuum dried (50°C, 12 hours) to obtain a white solid product. The yield of intermediate 44c was 19.34 g, and the yield was 81%.

[0397] Synthesis of Compound 44

[0398]

[0399] Compound 44 was synthesized in the same way as compound 43, except that intermediate 44c was used instead of 2-([1,1':3',1'' terphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

[0400] Compounds 43 and 44 obtained above, and Comparative Example compounds C1 and C2 below were each prepared as sample solids.

[0401] <Comparative Example Compound C1>

[0402]

[0403] <Comparative Example Compound C2>

[0404]

[0405] <Solubility Evaluation>

[0406] 50 mg of the solid sample was placed in a colorless sample bottle, 500 mg of methyl benzoate was added as a solvent, and ultrasonic irradiation was performed at room temperature for 20 minutes to visually check for the presence of any remaining solid sample. If any solid sample remained, solvent was added little by little, and ultrasonic irradiation was repeated to completely dissolve it. The solubility was then calculated based on the amount of solvent at the time of dissolution. The results are shown in Table 1 below.

[0407] <Evaluation of Solution Pot Life>

[0408] 50 mg of the sample solid was placed in a colorless sample bottle, 1.0 g of methyl benzoate was added as a solvent, and the solution was heated to 150°C to completely dissolve the sample solid, thereby preparing a 5 wt% solution. Subsequently, the solution was cooled to room temperature and observation began; the time (h) until precipitated solids, such as crystals, were visually confirmed was determined as the pot life. In other words, the longer the pot life, the more difficult crystallization becomes. The measurement results are shown in Table 1 below. Additionally, "*1" indicates that measurement was not possible because the comparative example compound did not dissolve.

[0409] compound Solubility of methyl benzoate at room temperature (wg%) Pot life of 5 wt% methyl benzoate solution Compound 43 >10 >300 Compound 44 >10 >300 Comparative Example Compound C1 0.1 *1 Comparative Example Compound C2 0.3 0.1 Comparative Example Compound C3 >10 >300 Comparative Example Compound C4 >10 >300 Comparative Example Compound C5 1 0.1

[0410] From Table 1 above, it can be confirmed that compounds 43 and 44 according to one embodiment of the present invention have superior solubility and pot life compared to the comparative example compounds.

[0411] <c3>

[0412]

[0413] <c4>

[0414]

[0415] <c5>

[0416]

[0417] <HOMO 및 LUMO 값의 측정>

[0418] Compounds 1 and 2 obtained above, and Comparative Example compounds C-1 and Cz3 below were each prepared as sample solids. Then, HOMO and LUMO values ​​were measured according to the following steps.

[0419] 1. Preparation of measurement samples

[0420] (1) A sample solution was prepared such that the sample solid was 4% by weight based on the weight of the solvent, methyl benzoate.

[0421] (2) The sample solution prepared in (1) above was applied to each of the ITO substrate and the quartz substrate by spin coating under conditions where the dry film thickness was 50 nm to form a coating film. The obtained coating film was 10 -1 After heating at 120℃ for 1 hour under a vacuum of Pa or less, 10 -1 A thin film layer (thin film sample) was formed by cooling to room temperature under a vacuum of Pa or less.

[0422] 2. Measurement of HOMO Values

[0423] The HOMO value was measured using an atmospheric photoelectron spectrometer AC-3 (manufactured by Riken Keiki Co., Ltd.) on a thin film sample on the ITO substrate prepared in 1. (2) above.

[0424] 3. Measurement of LUMO Values

[0425] Using a thin film sample on the quartz substrate prepared in 1. (2) above, the energy gap value (E at the absorption end of the ultraviolet-visible absorption spectrum) at the absorption end of the ultraviolet-visible absorption spectrum was obtained using a spectrophotometer U-3900 (manufactured by Hitachi High-Tech Kagaku). g ) was measured, and the LUMO value was calculated by the following formula (3).

[0426] [Mathematical Formula 3]

[0427] LUMO = HOMO + E g

[0428] The results of the calculation are shown in Table 2 below.

[0429] Glass transition temperature (T g Measurement of )

[0430] Compounds 43 and 44 and comparative example compounds C1 to C2 were each prepared as sample solids. In addition, Az1, an azine ring derivative used in the manufacture of the organic light-emitting diode described later, TEG, a phosphorescent platinum group metal complex, and comparative example compounds Cz1 to Cz3 were each prepared as sample solids.

[0431] Next, the scanning measurement process was repeated three times using a differential scanning calorimeter DSC6220 (manufactured by Seiko Corporation) with approximately 5 mg of the solid sample. Here, the measurement conditions were set as a heating rate of 10°C / min in the range of -50°C to 300°C and a cooling rate of -50°C / min in the range of 300°C to -50°C. From the scanning calorimetry curves from the second and subsequent measurements, the glass transition temperature (T g ) was measured. The measurement results are shown in Table 2 below.

[0432] compound HOMO(eV) LUMO(eV) T g (℃) Compound 43 -6.2 -2.7 92 Compound 44 -6.2 -2.8 109 Az1 -5.9 -3.0 125 TEG -5.4 -2.9 - (No measurement) Comparative example compound Cz1 -5.6 -2.3 115 Comparative example compound Cz2 -5.8 -2.6 108 Comparative example compound Cz3 -6.0 -3.0 95 Comparative Example Compound C1 -6.1 -2.8 126 Comparative Example Compound C2 -6.1 -2.8 120 Comparative Example Compound C3 -6.3 -2.8 108 Comparative Example Compound C4 -6.2 -2.6 147 Comparative Example Compound C5 -6.3 -2.7 121

[0433] Fabrication of Organic Light Emitting Diodes

[0434] Example 1

[0435] First, a glass substrate was prepared with a stripe-shaped 150 nm ITO (indium tin oxide) (anode) deposited as the first electrode (anode). PEDOT / PSS (poly(3,4-ethylene dioxythiophene) / poly(4-styrenesulfonate) (manufactured by Sigma-Aldrich) was applied onto the glass substrate by spin coating to a dry film thickness of 30 nm to form a hole injection layer.

[0436] Next, on the hole injection layer, anisole as a solvent and 3 parts by weight of a hole transport polymer (HTP1) having a repeating structure represented by the following chemical formula (weight average molecular weight M) per 100 parts by weight based on the weight of the solvent w = 400,000, PDI (M w / M n A hole transport layer coating solution was prepared comprising )= 2.7) and 0.6 parts by weight of the low molecular weight compound AD1 per 100 parts by weight of the above solvent. Subsequently, the obtained hole transport layer coating solution was applied by a spin coat method to form a coating film with a dry film thickness of 125 nm. The obtained coating film was 10 -1 After heating at 230℃ for 1 hour under a vacuum of Pa or less, 10 -1 Cooled to room temperature under a vacuum of Pa or less, and a hole transport layer was formed.

[0437]

[0438] Next, an ink for a light-emitting layer, which is a liquid composition (a methyl benzoate solution containing the compound 43 obtained above and the following compound Az1 as a host material and the following compound TEG (D1, tris(2-(3-p-xylyl)phenyl)pyridine iridium) as a dopant material) was applied by spin coating to a dry film thickness of 50 nm on the hole transport layer to form a light-emitting layer on the hole transport layer.

[0439] The ink for the light-emitting layer above was prepared such that, with respect to 100 parts by weight of methyl benzoate, which is the solvent, the solid content consists of 2.64 parts by weight of compound 43, 1.32 parts by weight of Az1, and 0.4 parts by weight of TEG.

[0440]

[0441] Next, (8-quinolinorato)lithium (Liq) and KLET-03 (product of Chemipro Kasei) were co-deposited on the above-mentioned light-emitting layer in a vacuum deposition apparatus at a weight ratio of 2:8 to form an electron transport layer with a thickness of 30 nm.

[0442] In addition, lithium fluoride (LiF) was deposited on the electron transport layer using a vacuum deposition device to form an electron injection layer with a thickness of 1 nm.

[0443] In addition, aluminum (Al) was deposited on the electron injection layer using a vacuum deposition device to form a second electrode (cathode) with a thickness of 100 nm.

[0444] After that, a sealed organic light-emitting diode was fabricated using a glass sealed tube containing a desiccant and a UV-curing resin in a nitrogen atmosphere glove box with a moisture concentration of 1 ppm or less and an oxygen concentration of 1 ppm or less.

[0445] Example 2

[0446] An organic light-emitting diode was fabricated in the same manner as in Example 1, except that compound 44 was used instead of compound 43 as the host material.

[0447] Example 3

[0448] An organic light-emitting device was fabricated in the same manner as in Example 1, except that the ink composition for the light-emitting layer was changed as follows.

[0449] The composition of the ink for the light-emitting layer was prepared such that, with respect to 100 parts by weight of methyl benzoate, which is the solvent, the solid content consists of 1.33 parts by weight of compound 43, 1.33 parts by weight of compound Cz1, 1.33 parts by weight of compound Az1, and 0.4 parts by weight of compound TEG.

[0450]

[0451] Example 4

[0452] An organic light-emitting diode was fabricated in the same manner as in Example 3, except that compound 44 was used instead of compound 43 as the host material.

[0453] Comparative Examples 1 to 3

[0454] An organic light-emitting device was fabricated in the same manner as in Example 1, except that the ink composition for the light-emitting layer was changed to the composition disclosed in Table 3 below.

[0455] Evaluation of Organic Light Emitting Diodes

[0456] Driving voltage, current efficiency, and luminous lifespan (durability) were evaluated according to the following method.

[0457] Using a DC constant voltage power supply (KEYENCE source meter), the applied voltage to the organic light-emitting diode was continuously varied from 0V to 20V, and current was passed through the organic light-emitting diode to cause it to emit light, and the brightness at this time was measured using a brightness measuring device (Topcom SR-3).

[0458] Here, the current value per unit area (current density) is calculated for the area of ​​the organic light-emitting diode, and the luminance (cd / m²) is calculated. 2 ) is the current density (A / m² 2 The current efficiency (cd / A) was calculated by dividing by ). In addition, current efficiency represents the efficiency of converting current into luminous energy (conversion efficiency), and a higher current efficiency indicates higher performance of the organic light-emitting diode.

[0459] In addition, the luminous life (durability) is at an initial brightness of 6,000 cd / m² 2 The time until the luminous brightness, which decreases with the passage of continuous operation time at the current value, reaches 80% of the initial brightness was measured as "LT80(h)".

[0460] The results of these evaluations are shown in Table 3 below. In addition, in Table 3 below, the current efficiency is expressed as a relative value when the current efficiency of the organic light-emitting device of Comparative Example 1 is set to 100. Also, the luminescence lifetime (durability) is expressed as a relative value when the device lifetime (LT80(h)) of the organic light-emitting device of Comparative Example 1 is set to 100.

[0461] composition of the light-emitting layer Driving voltage (V) @ 1,000 (cd / m 2 ) Current efficiency (relative value) @ 1,000 (cd / m²) 2 ) Luminous lifespan (relative value) @ 6,000 (cd / m²) 2 ) Example 1 Compound 43:Az1:TEG(66:33:10) 6.1 138 325 Example 2 Compound 44:Az1:TEG(66:33:10) 6.0 140 360 Example 3 Compound 43:Cz1:Az1:TEG(33:33:33:10) 5.2 116 240 Example 4 Compound 44:Cz1:Az1:TEG(33:33:33:10) 5.0 122 260 Comparative Example 1 Cz1:Az1:TEG(66:33:10) 5.5 100 100 Comparative Example 2 Cz2:Az1:TEG(66:33:10) 7.5 98 45 Comparative Example 3 Cz3:Az1:TEG(66:33:10) 6.2 111 170 Comparative Example 4 C1:Az1:TEG(66:33:10) Device fabrication is impossible because coating film formation is impossible. Comparative Example 5 C2:Az1:TEG(66:33:10) Device fabrication is impossible because coating and film deposition are impossible. Comparative Example 6 C3:Az1:TEG(66:33:10) 6.7 73 40 Comparative Example 7 C4:Az1:TEG(66:33:10) 5.9 90 120 Comparative Example 8 C5:Az1:TEG(66:33:10) Device fabrication is impossible because coating and film deposition are impossible.

[0462]

[0463] From the results of Table 3, it can be seen that Examples 1 and 2, which used a condensed ring compound represented by Formula 1 as a host along with the azine ring derivative Az1, have superior luminescence efficiency and luminescence lifetime compared to Comparative Examples 1 to 3, which used a carbazole derivative, a hole-transporting host material commonly used in the past.

[0464] In addition, for C1, C2, and C5, which had poor pot life, it was difficult to fabricate light-emitting devices by solution process (Comparative Examples 4, 5, and 8).

[0465] In addition, including an ortho-phenyl group In the case of Comparative Example 6, in which C3 was applied as a host, and Comparative Example 7, in which C4 including a fluorene group connected to position 9 was applied as a host, it was possible to fabricate a light-emitting device, but the current efficiency and light-emitting lifetime characteristics were significantly worse than those of the example.

[0466] In addition, by including a compound represented by Chemical Formula 1 and a compound containing a carbazole moiety together (Examples 3 and 4), not only was the luminous efficiency excellent, but the driving voltage was significantly reduced and it was found to be superior in power consumption.

[0467] Although the present invention has been described above with reference to synthesis examples and embodiments, the present invention is not limited to specific embodiments and various modifications are possible within the scope of the invention as described in the claims. Explanation of the symbols

[0468] 100: Organic light-emitting diode 110: Substrate 120: First electrode 130: Hole injection layer 140: Precision transport layer 150: Emissive layer 160: Electron transport layer 170: Electron injection layer 180: Second electrode < / c4> < / c3>

Claims

Claim 1 Condensed ring compounds represented by the following chemical formula 1: <Chemical Formula 1> <Chemical Formula 2> Among the above chemical formulas 1 and 2, L1 and L 11 C5-Cs independently of each other, single-bonded, or substituted or unsubstituted 60 Selected from a carbocyclic group, L2 is a benzene group, a1 and a11 are independently selected from integers 1 to 5, a2 is 0 or 1, and Ar 11 C5-C with substituted or unsubstituted 60 It is a carbocyclic group, Ar1 is a benzene group, and R3 to R6 are independently groups represented by Chemical Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C7-C 60 Alkyl aryl groups, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 Heteroaryl group, substituted or unsubstituted C2-C 60 Alkyl heteroaryl group, substituted or unsubstituted C1-C 60 Heteroaryloxy groups, substituted or unsubstituted C1-C 60 Selected from heteroarylthio groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic groups, -Si(Q1)(Q2)(Q3) and -N(Q1)(Q2), R1 and R2 are independently phenyl groups, R3 is not a group represented by Formula 2, b3 to b6 are independently 0, n1 is 1, and the substituted C5-C 60 Carbocyclic group, substituted C1-C 60 Heterocyclic group, substituted C1-C 30 Heterocyclic group, substituted C1-C 60 Alkyl groups, substituted C2-C 60 alkenyl group, substituted C2-C 60 alkynyl group, substituted C1-C 60 Alkoxy group, substituted C3-C 10 Cycloalkyl group, substituted C1-C 10 Heterocycloalkyl group, substituted C3-C 10 Cycloalkenyl group, substituted C1-C 10 Heterocycloalkenyl group, substituted C6-C 60 Aryl group, substituted C7-C 60 alkylaryl group, substituted C6-C 60 aryloxy group, substituted C6-C 60 Arylthio group, substituted C1-C 60 Heteroaryl group, substituted C2-C 60 Alkyl heteroaryl group, substituted C1-C 60 Heteroaryloxy group, substituted C1-C 60 A heteroarylthio group, a substituted monovalent non-aromatic condensed polycyclic group, and at least one of the substituents of the substituted monovalent non-aromatic heterocondensed polycyclic group is deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, -NCS, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphate group or a salt thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group and C1-C 60 Alkoxy group; deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, -NCS, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ) and -C(=O)(Q 11 C1-C substituted with at least one selected from ) 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group and C1-C 60 Alkoxy group; C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, and C1-C 10 Heterocycloalkenyl group; deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ) and -C(=O)(Q 21 C3-C substituted with at least one selected from ) 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, and C1-C 10 Heterocycloalkenyl group; and -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ) and -C(=O)(Q 31 Selected from ); and the above Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 They are independently hydrogen, deuterium, C1-C 20 Alkyl group, C1-C 20 Selected from alkoxy groups, phenyl groups and biphenyl groups, and is a bonding site with an adjacent atom. Claim 2 In paragraph 1, the above L1 and L 11 are independently of each other, single bonds, benzene group, pentylene group, indene group, naphthalene group, anthracene group, azulene group, heptylene group, acenaphthalene group, phenalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthrene group, biphenyl group, terphenyl group, triphenylene group, fluoranthene group, pyrene group, chrysene group, fisene group, perylene group, pentapene group, pentacene group, tetraphenyl group, hexaphenyl group, hexacene group, rubicene group, trinaphthalene group, heptaphenyl group, and pyranthrene group; and deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, C1-C 30 Alkyl group, C1-C 30 Benzene group, pentalene group, indene group, naphthalene group, anthracene group, azulene group, heptalene group, acenaphthyl group, phenalenyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, dibenzoflurenyl group, phenanthrenyl group, biphenyl group, terphenyl group, triphenylenyl group, fluoranthenyl group, pyrenyl group, chrysenyl group, fisenyl group, perylenyl group, pentaphenyl group, pentacenyl group, tetraphenyl group, hexaphenyl group, hexacenyl group, rubisenyl group, trinaphthyl group, heptaphenyl group, and pyrantrenyl group substituted with at least one selected from alkoxy group, phenyl group, penthalenyl group, indene group, naphthalene group, anthracene group, azulene group, heptalene group, acenaphthalene group, substituted with at least one selected from alkoxy group, phenyl group, penthalenyl group, indene group, naphthalene group, anthracene group, azulene group, heptalene group, acenaphthalene group, Condensed ring compounds selected from phenalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthrene group, biphenyl group, terphenyl group, triphenylene group, fluoranthene group, pyrene group, chrysene group, fisene group, perylene group, pentapene group, pentacene group, tetraphenyl group, hexaphenyl group, hexacene group, rubicene group, trinaphthalene group, heptaphenyl group, and pyranthrene group. Claim 3 In paragraph 1, the above L1 and L 11 are independently of each other, single bonds, benzene groups, biphenyl groups, terphenyl groups, and tetraphenyl groups; and deuterium, -F, -Cl, -Br, -I, hydroxyl groups, cyano groups, nitro groups, amino groups, amidino groups, hydrazine groups, hydrazone groups, C1-C 30 Alkyl group, C1-C 30 A condensed ring compound selected from a benzene group, a biphenyl group, a terphenyl group, and a tetraphenyl group, substituted with at least one selected from an alkoxy group, a phenyl group, a biphenyl group, and a terphenyl group. Claim 4 In paragraph 1, the above L1 and L 11 Condensed ring compounds, independently having a single bond and one of the groups represented by the following chemical formulas 3-1 to 3-7: Among the above chemical formulas 3-1 to 3-7, Z 31 To Z 33 They are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, C1-C 20 Alkyl group, C1-C 20 Alkoxy group, phenyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, and -Si(Q 31 )(Q 32 )(Q 33 Selected from ), d4 is an integer from 0 to 4, and Q 31 to Q 33 They are independently hydrogen, deuterium, C1-C 20 Alkyl group, C1-C 20 Selected from alkoxy groups, phenyl groups and biphenyl groups, and * and *' are bonding sites with neighboring atoms. Claim 5 In paragraph 1, the above Ar 11 ... is phenyl group, penthalenyl group, indenyl group, naphthyl group, anthracenyl group, azulenyl group, hepthalenyl group, acenaphthyl group, phenalenyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, dibenzoflurenyl group, phenanthrenyl group, biphenyl group, terphenyl group, fluoranthenyl group, pyrenyl group, chrysenyl group, fisenyl group, perylenyl group, pentaphenyl group, pentacenyl group, tetraphenyl group, hexaphenyl group, hexacenyl group, rubisenyl group, trinaphthyl group, heptaphenyl group, and pyrantrenyl group; and deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, C1-C 30 Alkyl group, C1-C 30 Substituted with at least one selected from alkoxy group, phenyl group, penthalenyl group, indenyl group, naphthyl group, anthracenyl group, azulenyl group, hepthalenyl group, acenaphthyl group, phenalenyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, dibenzoflurenyl group, phenanthrenyl group, biphenyl group, terphenyl group, fluoranthenyl group, pyrenyl group, chrysenyl group, fisenyl group, perylenyl group, pentaphenyl group, pentacenyl group, tetraphenyl group, hexaphenyl group, hexacenyl group, rubisenyl group, trinaphthyl group, heptaphenyl group, and pyrantrenyl group, phenyl group, penthalenyl group, indenyl group, naphthyl group, anthracenyl group, azulenyl group, hepthalenyl group, acenaphthyl group, A condensed ring compound selected from phenalenyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, dibenzoflurenyl group, phenanthrenyl group, biphenyl group, terphenyl group, fluoranthenyl group, pyrenyl group, chrysenyl group, fisenyl group, perylenyl group, pentaphenyl group, pentacenyl group, tetraphenyl group, hexaphenyl group, hexacenyl group, rubisenyl group, trinaphthyl group, heptaphenyl group, and pyrantrenyl group. Claim 6 In paragraph 1, the above Ar 11 phenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, biphenyl group, terphenyl group, and tetraphenyl group; and deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, C1-C 30 Alkyl group, C1-C 30 A condensed ring compound selected from a phenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, biphenyl group, terphenyl group, and tetraphenyl group, substituted with at least one selected from alkoxy group, phenyl group, biphenyl group, and terphenyl group. Claim 7 In paragraph 1, the above Ar 11 Condensed ring compounds that are groups represented by the following chemical formulas 4-1 to 4-9: Among the above chemical formulas 4-1 to 4-9, Y 41 is C(Z 45 )(Z 46 ) and,Z 41 To Z 46 They are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, C1-C 20 Alkyl group, C1-C 20 Alkoxy group, phenyl group, and -Si(Q 31 )(Q 32 )(Q 33 Selected from ), e3 is an integer from 0 to 3, e4 is an integer from 0 to 4, e5 is an integer from 0 to 5, e7 is an integer from 0 to 7, and Q 31 to Q 33 They are independently hydrogen, deuterium, C1-C 20 Alkyl group, C1-C 20 Selected from alkoxy groups, phenyl groups and biphenyl groups, and is a bonding site with an adjacent atom. Claim 8 In claim 1, the above R3 to R6 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 Alkyl group, C2-C 20 alkenyl group, C2-C 20 alkynyl group, C1-C 20 Alkoxy groups, phenyl groups, and naphthyl groups; and C1-C groups substituted with one or more selected from deuterium, -F, -Cl, -Br, -I, cyano groups, phenyl groups, biphenyl groups, and terphenyl groups. 20 Alkyl group, C2-C 20 alkenyl group, C2-C 20 alkynyl group, C1-C 20 A condensed ring compound selected from alkoxy groups, phenyl groups, and naphthyl groups. Claim 9 In claim 1, a condensed ring compound that is a group represented by the following chemical formula 1A: <Chemical Formula 1A> The description of L1 to L2, a1 to a2, Ar1, R1 to R4 and R6, b3 to b4 and b6, and n1 in the above chemical formula 1A refers to the definition in claim 1. Claim 10 A condensed ring compound according to claim 1 that does not contain an ortho-phenylene group. Claim 11 A composition comprising one or more condensed ring compounds represented by Chemical Formula 1 of any one of claims 1 to 10. Claim 12 A composition according to claim 11, further comprising a first compound comprising one or more of a carbazole-based moiety or an m-phenyl moiety. Claim 13 A composition according to claim 11, further comprising a second compound comprising an azine-based moiety. Claim 14 A composition comprising a luminescent material, further comprising, in Clause 11. Claim 15 A composition comprising a solvent in addition to the solvent in Clause 11. Claim 16 An organic light-emitting device comprising: a first electrode; a second 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 condensed ring compounds represented by the chemical formula 1 of any one of claims 1 to 10. Claim 17 In claim 16, the organic light-emitting device further comprises a light-emitting material in the organic layer, wherein the light-emitting material emits light from a triplet exciton.

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