Organometallic compound, organic light-emitting device containing the same, and diagnostic composition containing the same

Abstract

To provide a novel organometallic compound, an organic light-emitting device employing the same, and a diagnostic composition employing the same.SOLUTION: The invention provides an organometallic compound represented, e.g., by formula 1 or formula 49.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to an organometallic compound, an organic light-emitting device containing the same, and a diagnostic composition containing the same, and more particularly, to an organometallic compound having a narrow half-value width and a short decay time, an organic light-emitting device containing the same, and a diagnostic composition containing the same.

Background Art

[0002] An organic light-emitting device is a self-luminous device, and has excellent characteristics such as a viewing angle, a response time, luminance, a driving voltage, and a response speed, and can be multi-colored. According to one example, an organic light-emitting device includes an anode, a cathode, and an organic layer including a light-emitting layer interposed between the anode and the cathode.

[0003] A hole transport region is provided between the anode and the light-emitting layer, and an electron transport region is 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. The holes and electrons recombine in the light-emitting layer region to generate excitons. Light is generated while the excitons change from the excited state to the ground state. In addition, luminescent compounds, for example, phosphorescent compounds, can also be used for monitoring, sensing, detecting, etc. of various biological substances such as various cells and proteins.

[0004] In the case of organometallic compounds used in organic light-emitting devices, the development of compounds that always improve characteristics such as the viewing angle, response time, luminance, driving voltage, and response speed has been an issue.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

SUMMARY OF THE INVENTION

PROBLEMS TO BE SOLVED BY THE INVENTION

[0006] The present invention has been made in view of the problems in the above-mentioned conventional organometallic compounds, and an object of the present invention is to provide a novel organometallic compound, an organic light-emitting device employing the same, and a diagnostic composition employing the same.

MEANS FOR SOLVING THE PROBLEMS

[0007] The organometallic compound according to the present invention made to achieve the above object is characterized by being represented by Chemical Formula 1 shown below.

CHEM.

[0008] The organic light-emitting device according to the present invention made to achieve the above object has 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 the organic layer contains one or more of the organometallic compounds of the present invention.

[0009] The diagnostic composition according to the present invention made to achieve the above object is characterized by containing one or more of the organometallic compounds of the present invention represented by Chemical Formula 1.

Advantages of the Invention

[0010] According to the organometallic compound, the organic light-emitting device containing the same, and the diagnostic composition containing the same according to the present invention, since it has a narrow half-value width and a short decay time, the quantum efficiency is improved. Therefore, the organic light-emitting device employing the same has an improved external quantum efficiency of light emission and a lower driving voltage. In addition, since the organometallic compound has excellent phosphorescent emission characteristics, a diagnostic composition having high diagnostic efficiency can be provided by using the same.

Brief Description of the Drawings

[0011]

Figure 1

Modes for Carrying Out the Invention

[0012] Next, specific examples of embodiments for implementing the organometallic compound according to the present invention, the organic light-emitting device including the same, and the diagnostic composition including the same will be described with reference to the drawings.

[0013] The organometallic compound of the present invention is represented by Chemical Formula 1 shown below.

Chemical Formula

[0014] In Chemical Formula 1, A1 to A3 are each independently selected from a C5-C 30 carbocyclic group and a C1-C 30 heterocyclic group. According to one embodiment, the aforementioned A1 to A3 are, independently of each other, selected from a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, an indazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a benzotriazole group, a diazaindene group, a triazaindene group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline.

[0015] For example, the aforementioned ring A1 and ring A3 are, independently of each other, selected from a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, and a dibenzosilole group. In Chemical Formula 1, A4 is a 5-membered heterocyclic group. According to one embodiment, A4 is selected from a cyclopentadienyl group, a furan group, a thiophene group, a pyrrole group, a silole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, and a triazasilole group. According to one embodiment, A4 is selected from a pyrrole group, a pyrazole group, an imidazole group, a triazole group, and a tetrazole group.

[0016] In Chemical Formula 1, A5 is (i) a C7-C polycyclic carbocyclic group containing a 6-membered carbocyclic group, and 30 a carbocyclic group, and (ii) a C1-C polycyclic heterocyclic group containing a 6-membered carbocyclic group or a 6-membered heterocyclic group 30 selected from the heterocyclic groups. According to one embodiment, the 6-membered carbocyclic group is also a cyclohexane group or a benzene group. For example, the 6-membered carbocyclic group is also a benzene group. According to one embodiment, the 6-membered heterocyclic group is selected from a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a triazine group. For example, the 6-membered heterocyclic group is also a pyridine group.

[0017] According to one embodiment, A5 is also a group represented by any one of Chemical Formulas A5-1 to A5-6 shown below.

Chemical Formula

[0018] In Chemical Formulas A5-1 to A5-6, Y 51is selected from *-O-*, *-S-*, *-N(R5)-*, *-C(R5)(R6)-*, *-Si(R5)(R6)-*, *-B(R5)-*, *-P(R5)-*, and *-P(=O)(R5)-*, For the descriptions of R5 and R6, refer to the descriptions of R1 and R2 respectively, X 42 and X 43 For the descriptions, refer to what is described in this specification, X 51 ~X 56 are, independently of each other, C or N.

[0019] X 51 is C(R 51 ) or N, and X 52 is C(R 52 ) or N, and X 53 is C(R 53 ) or N, and X 54 is C(R 54 ) or N, and X 55 is C(R 55 ) or N, and X 56 is C(R 56 ) or N, R 51 ~R 56 For the descriptions, independently of each other, refer to the description of R 50 . According to one embodiment, X 51 ~X 56 are each also C. According to one embodiment, at least one of X 51 ~X 56 is also N. According to one embodiment, any one of X 51 ~X 56 is also N.

[0020] In Chemical Formula 1, X 10 , X 20 , X 30 and X 40 ~X 44 are, independently of each other, C or N. According to one embodiment, X 10 is N, and X 20 , X 30 and X 40 are each also C. According to one embodiment, in A4, X 40 is C, and X 41 and X 44 are each also N. According to one embodiment, in A4, X 42 and X 43 are each also C. According to one embodiment, the binding of the aforementioned M1 and X 10 , the binding of the aforementioned M1 and X 20 , the binding of the aforementioned M1 and X 30 , and the binding of the aforementioned M1 and X 40 are each, independently of one another, also a coordination bond or a covalent bond.

[0021] In Chemical Formula 1, for the binding of the aforementioned M1 and X 10 , the binding of the aforementioned M1 and X 20 , the binding of the aforementioned M1 and X 30 , and the binding of the aforementioned M1 and X 40 , two of them are covalent bonds, and the remaining two are also coordination bonds. Thereby, the organometallic compound represented by Chemical Formula 1 is electrically neutral. According to one embodiment, the binding of M1 and X 10 is a coordination bond, the binding of M1 and X 20 is a covalent bond, the binding of M1 and X 30 is a covalent bond, and the binding of M1 and X 40 is also a coordination bond.

[0022] In Chemical Formula 1, T1 to T3 are, independently of one another, a single bond, *-N[(L1) a1 -(R1) b1It is selected from among - *’-*, -B(R1)-*’-*, -P(R1)-*’-*, -C(R1)(R2)-*’-*, -Si(R1)(R2)-*’-*, -Ge(R1)(R2)-*’-*, -S-*’-*, -Se-*’-*, -O-*’-*, -C(=O)-*’-*, -S(=O)-*’-*, -S(=O)2-*’-*, -C(R1)=*’-*, *=C(R1)-*’-*, -C(R1)=C(R2)-*’-*, -C(=S)-*’-*, and -C≡C-*’-*. For the descriptions of the aforementioned R1 and R2, refer to the following. According to one embodiment, the aforementioned T1 to T3 are, independently of each other, -N[(L1) a1 -(R1) b1 -*’-*, -C(R1)(R2)-*’-*, -Si(R1)(R2)-*’-*, -O-*’-*, and -S-*’-*, and are also selected from among them. For example, T1 is -N[(L1) a1 -(R1) b1 -*’-*, -O-*’-*, and -S-*’-*, and is also selected from among them.

[0023] In Chemical Formula 1, n1 to n3 are, independently of each other, integers selected from among 1 to 3. According to one embodiment, n1 to n3 are, independently of each other, also 1 or 2. According to one embodiment, n1 to n3 are each also 1.

[0024] In Chemical Formula 1, L1 is a single bond, a substituted or unsubstituted C5-C 30 carbocyclic group, and a substituted or unsubstituted C1-C 30 heterocyclic group, and is selected from among them. According to one embodiment, L1 is a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, and a pentacenylene group, and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid 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, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C1-C 60 Selected from at least one of a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, and substituted phenylene group, pentalenylene group, indenylene group, naphthylene group, azulylene group, heptalenylene group, acenaphthylene group, fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylenylene group, and pentacenylene group.

[0025] a1 is selected from 1 to 3, and when a1 is 2 or more, two or more L1s may be the same or different from each other. For example, a1 is also 1 or 2.

[0026] In Chemical Formula 1, R1, R2, R 10 , R 20 , R 30 , R 40 , and R 50are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic hetero-condensed polycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7), and -P(=O)(Q8)(Q9).

[0027] The aforementioned R1 and R2 are optionally bonded to each other via a single bond, a double bond or a first linking group, and at least one R 10a substituted or unsubstituted C5-C 30 carbocyclic group, or at least one R 10a substituted or unsubstituted C1-C 30 heterocyclic group (for example, a fluorene group, a xanthene group, an acridine group, etc. substituted or unsubstituted with at least one R 10a ) can be formed. R 10a For the description of, refer to the description of R1 in this specification.

[0028] The first linking group is selected from among *-N(R3)-*’, *-B(R3)-*’, *-P(R3)-*’, *-C(R3)(R4)-*’, *-Si(R3)(R4)-*’, *-Ge(R3)(R4)-*’, *-S-*’, *-Se-*’, *-O-*’, *-C(=O)-*’, *-S(=O)-*’, *-S(=O)2-*’, *-C(R3)=*’, *=C(R3)-*’, *-C(R3)=C(R4)-*’, *-C(=S)-*’, and *-C≡C-*’. For the descriptions of R3 and R4 mentioned above, refer to the descriptions of R1 in this specification respectively. * and *’ are bonding sites with adjacent atoms respectively.

[0029] b1 is selected from 1 to 5. When b1 is 2 or more, two or more R1s may be the same as or different from each other. For example, b1 may also be 1, 2, or 3. b10, b20, b30, and b50 are integers independently selected from 1 to 10 respectively, b40 is an integer independently selected from 1 to 3 respectively, When b10 is 2 or more, two or more Rs 10 may be the same as or different from each other. When b20 is 2 or more, two or more Rs 20 may be the same as or different from each other. When b30 is 2 or more, two or more Rs 30 may be the same as or different from each other. When b40 is 2 or more, two or more Rs 40 may be the same as or different from each other. When b50 is 2 or more, two or more Rs 50 may be the same as or different from each other.

[0030] According to one embodiment, the aforementioned R1, R2, R 10 , R 20 , R 30 , R 40 and R 50 are independently of each other Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SF5, C1-C 20 alkyl group, and C1-C 20 alkoxy group, 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 its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 10 alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, pyridinyl group, and at least one of pyrimidinyl group-substituted, C1-C 20 alkyl group and C1-C 20 alkoxy group, Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, and imidazopyrimidinyl group, 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 its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl group, C1-C 20An alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, wherein at least one selected from the group consisting of these substituents is substituted on a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,A triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, and selected from -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7), and -P(=O)(Q8)(Q9), Q1 to Q9 are each independently -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, and -CD2CDH2, 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 sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, and deuterium, C1-C 10 also selected from 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 sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, which are substituted with at least one selected from a deuterium, a C1-C

[0031] For example, the aforementioned R1 and R2 are each independently a C1-C 30 alkyl group, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 10 alkyl group, a C1-C 10A C1-C alkyl group substituted with at least one of an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group, and 30 a C1-C alkyl group, and a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, and deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 10 alkyl group, a C1-C 10A phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, and imidazopyrimidinyl group, which is also selected from among those substituted with at least one of an alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, pyridinyl group, and pyrimidinyl group.

[0032] According to another embodiment, the aforementioned R1, R2, R 10 , R 20 , R 30 , R 40 and R 50are, independently of each other, hydrogen, deuterium, -F, cyano group, nitro group, -SF5, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec-decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, carbazolyl group, dibenzofuranyl group, and dibenzothiophenyl group, deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano group, nitro group, C1-C 10 alkyl group, C1-C 10A 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 sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, substituted with at least one selected from the group consisting of -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7), and -P(=O)(Q8)(Q9), selected from the group consisting of Q1 to Q9 are each independently -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, and -CD2CDH2 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 sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, and Deuterium, C1-C 10 Selected from at least one of deuterium, C1-C alkyl groups, and phenyl groups, and also selected from n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, and naphthyl groups which are substituted thereby.

[0033] For example, the aforementioned R1, R2, R 10 , R 20 , R 30 , R 40 and R 50 are each independently selected from hydrogen, deuterium, -F, cyano group, nitro group, -SF5, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, groups represented by Chemical Formulas 9-1 to 9-19 shown below, and groups represented by Chemical Formulas 10-1 to 10-194 shown below.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chem.

[0034] Chemical formulas 9-1 to 9-19 and chemical formulas 10-1 to 10-194, where * is a bonding site with an adjacent atom, Ph is a phenyl group, and TMS is a trimethylsilyl group. According to one embodiment, at least one of R 10 is also selected from among chemical formulas 9-1 to 9-19. According to one embodiment, at least one of R 40 is also selected from among chemical formulas 9-1 to 9-19 and chemical formulas 10-1 to 10-194.

[0035] According to one embodiment, in the aforementioned R1, R2, R 10 , R 20 , R 30 , R 40 , and R 50 , at least one is a C1-C 30 alkyl group, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 10 alkyl group, a C1-C 10 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group, and is a C1-C 30 alkyl group substituted with at least one of them, Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, and imidazopyrimidinyl group, and 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 its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 alkyl group, C1-C 20An alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group, wherein the cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group is substituted with at least one selected from the group consisting ofIt is also selected from among a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group.

[0036] In Chemical Formula 1, b1, b10, b20, b30, and b40 each represent the number of R1, R 10 , R 20 , R 30 , R 40 , and R 50 , respectively. b1 is an integer selected from 1 to 5, b10 and b40 are each independently an integer selected from 1 to 4, and b20 and b30 are each independently an integer selected from 1 to 3. When b1 is 2 or more, two or more R1s may be the same as or different from each other. When b10 is 2 or more, two or more R 10 s may be the same as or different from each other. When b20 is 2 or more, two or more R 20 s may be the same as or different from each other. When b30 is 2 or more, two or more R 30 s may be the same as or different from each other. When b40 is 2 or more, two or more R 40 s may be the same as or different from each other.

[0037] According to one embodiment, in R1, R2, R 10 , R 20 , R 30 , R 40 , and R 50 , two or more adjacent ones may selectively bond to each other to form a substituted or unsubstituted C5-C 30 carbocyclic group or a substituted or unsubstituted C1-C 30 heterocyclic group. For example, in Chemical Formula 1, when b10 is 2 or more, two or more R 10 s selectively bond to each other, and at least one R 10aIt is possible to form a substituted or unsubstituted cyclopentane group, cyclopentadiene group, furan group, thiophene group, pyrrole group, silole group, adamantane group, norbornane group, norbornene group, cyclohexane group, cyclohexene group, benzene group, naphthalene group, indene group, indole group, benzofuran group, benzothiophene group, benzosilole group, fluorene group, carbazole group, dibenzofuran group, dibenzothiophene group, or dibenzosilole group.

[0038] In other embodiments, in Chemical Formula 1, when b20 is 2 or more, two or more Rs 20 are selectively bonded to each other, and at least one R 10a It is possible to form a substituted or unsubstituted cyclopentane group, cyclopentadiene group, furan group, thiophene group, pyrrole group, silole group, adamantane group, norbornane group, norbornene group, cyclohexane group, cyclohexene group, benzene group, naphthalene group, indene group, indole group, benzofuran group, benzothiophene group, benzosilole group, fluorene group, carbazole group, dibenzofuran group, dibenzothiophene group, or dibenzosilole group.

[0039] In other embodiments, in Chemical Formula 1, when b30 is 2 or more, two or more Rs 30 are selectively bonded to each other, and at least one R 10a It is possible to form a substituted or unsubstituted cyclopentane group, cyclopentadiene group, furan group, thiophene group, pyrrole group, silole group, adamantane group, norbornane group, norbornene group, cyclohexane group, cyclohexene group, benzene group, naphthalene group, indene group, indole group, benzofuran group, benzothiophene group, benzosilole group, fluorene group, carbazole group, dibenzofuran group, dibenzothiophene group, or dibenzosilole group.

[0040] In other embodiments, in Chemical Formula 1, when b40 is 2 or more, two or more Rs 40 are selectively bonded to each other, and at least one R 10aIt is possible to form a cyclo pentane group, a cyclo pentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an indene group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, or a dibenzosilole group, which may be substituted or unsubstituted.

[0041] In other embodiments, in Chemical Formula 1, when b50 is 2 or more, two or more Rs 50 are selectively bonded to each other, and at least one R 10a forms a cyclo pentane group, a cyclo pentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an indene group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, or a dibenzosilole group, which may be substituted or unsubstituted.

[0042] In other embodiments, in Chemical Formula 1, R1 and R2 are selectively bonded to each other, and at least one R10aで forms a cyclo pentane group, a cyclo pentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an indene group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, or a dibenzosilole group, which may be substituted or unsubstituted.

[0043] In other embodiments, in Chemical Formula 1, any one of R1 and R2, and R 10 , R 20 , R 30 , R 40 , and R 50In this case, any one of them is selectively combined with each other, and at least one R 10a A cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an indene group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, or a dibenzosilole group which may be substituted or unsubstituted by 10a can be formed.

[0044] According to one embodiment, the organometallic compound represented by Chemical Formula 1 is also represented by any one selected from Chemical Formulas 11-1 to 11-6 shown below.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0045] In the described Chemical Formulas 11-1 to 11-6, M1, A1 to A3, X 10 、X 20 、X 30 、X 42 、X 43 、T1 to T3, R 10 、R 20 、R 30 、R 40 、R 50 For the explanations of b10, b20, and b30, refer to what is described in this specification, Y51 is selected from among *-O-*, *-S-*, *-N(R5)-*, *-C(R5)(R6)-*, *-Si(R5)(R6)-*, *-B(R5)-*, *-P(R5)-*, and *-P(=O)(R5)-*; For the descriptions of R5 and R6, refer to the descriptions of R1 and R2 respectively. X 51 is C(R 51 ) or N, and X 52 is C(R 52 ) or N, and X 53 is C(R 53 ) or N, and X 54 is C(R 54 ) or N, and X 55 is C(R 55 ) or N, and X 56 is C(R 56 ) or N; R 51 ~R 56 For the descriptions of them, independently of each other, refer to the description of R 50 .

[0046] According to one embodiment, the organometallic compound represented by Chemical Formula 1 is also represented by any one selected from Chemical Formulas 12-1 to 12-6 shown below.

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

[0047] In Chemical Formulas 12-1 to 12-6, M1, X 10 , X 20 , X 30 , X 42 , X 43 , R 40 and the description of T2 refer to what is described in this specification. Y 51 is selected from among *-O-*’, *-S-*’, *-N(R5)-*’, *-C(R5)(R6)-*’, *-Si(R5)(R6)-*’, *-B(R5)-*’, *-P(R5)-*, and *-P(=O)(R5)-*’. The description of R5 and R6 respectively refers to the description of R1 and R2. X 11 is C(R 11 ) or N, X 12 is C(R 12 ) or N, X 13 is C(R 13 ) or N, X 14 is C(R 14 ) or N, X 21 is C(R 21 ) or N, X 22 is C(R 22 ) or N, X 23 is C(R 23 ) or N, X 24 is C(R 24 ) or N, X 25 is C(R 25 ) or N, X 26 is C(R 26 ) or N, X 31 is C(R 31 ) or N, X 32 is C(R 32 ) or N, X 33 is C(R 33 ) or N, X 51 is C(R 51 ) or N, X 52 is C(R 52 ) or N, X 53is C(R 53 ) or N, X 54 is C(R 54 ) or N, X 55 is C(R 55 ) or N, X 56 is C(R 56 ) or N, R 11 ~R 14 For the descriptions of R 10 ~R R 21 ~R 26 are independent of each other and refer to the description of R 20 , R 31 ~R 33 For the descriptions of R 30 ~R R 51 ~R 56 are independent of each other and refer to the description of R 50 .

[0048] According to still other embodiments, the organometallic compound is also one of Compounds 1 to 72 shown below, but is not limited thereto. [Chemical Formula] [Chemical Formula] [Chemical Formula] [Chemical Formula] [Chemical Formula] [Chemical Formula]

[0049] The organometallic compound represented by Chemical Formula 1 satisfies the structure of Chemical Formula 1 mentioned above. Due to the structure in which A5, which is a group of two or more rings that necessarily includes a six-membered ring, is condensed to A4, which is a five-membered heterocyclic group, it is suitable for deep blue emission. An electronic device that employs the organometallic compound represented by Chemical Formula 1, for example, an organic light-emitting device, has excellent luminous efficiency, color coordinates, and the effect of lowering the driving voltage.

[0050] For example, the energy levels of HOMO (highest occupied molecular orbital), LUMO (lowest unoccupied molecular orbital), singlet (S1), and triplet (T1) related to Compounds 1 to 12 and 49, and Compounds A and B were evaluated using the DFT (density functional theory) method (B3LYP, 6-31G(d,p)) of the Gaussian program to optimize the structure at the level. The results are as shown in Table 1 below.

Table 1

[0051] From Table 1, it can be confirmed that the organometallic compound represented by Chemical Formula 1 has a high T1 energy level and suitable electrical properties for use as a light-emitting layer material in an electronic device, for example, an organic light-emitting device.

[0052] The synthesis method of the organometallic compound represented by Chemical Formula 1 can be recognized by those skilled in the art with reference to the synthesis examples described later. Therefore, the organometallic compound represented by Chemical Formula 1 is suitable for use as an organic layer of an organic light-emitting device, for example, a light-emitting layer material. From another aspect, it provides an organic light-emitting device including 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 the organic layer contains at least one or more of the organometallic compounds represented by Chemical Formula 1. The organic light-emitting device can have a low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, low roll-off ratio, and excellent color purity by including an organic layer containing the organometallic compound represented by Chemical Formula 1 as described above.

[0053] For example, in an organic light-emitting device, the first electrode is an anode, the second electrode is a cathode, the organic layer further includes a hole transport region interposed between the first electrode and the light-emitting layer, and an electron transport region interposed between the light-emitting layer and the second electrode. The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof. The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0054] In another embodiment, the organometallic compound represented by Chemical Formula 1 is also included in the light-emitting layer. The organometallic compound included in the light-emitting layer serves as an emitter. For example, the light-emitting layer containing the organometallic compound represented by Chemical Formula 1 emits phosphorescence generated while triplet excitons of the organometallic compound transition to the ground state. According to one embodiment, the light-emitting layer containing the organometallic compound represented by Chemical Formula 1 may further include a host. The host is selected from any host, and for a detailed description of the host, refer to what is described in this specification. The content of the host in the light-emitting layer is more than the content of the organometallic compound represented by Chemical Formula 1.

[0055] According to another embodiment, the light-emitting layer includes a host and a dopant. The host is selected from any host, and the dopant may include the organometallic compound represented by Chemical Formula 1. The light-emitting layer emits phosphorescence generated while triplet excitons of the organometallic compound serving as a dopant transition to the ground state. According to one embodiment, the light-emitting layer can emit blue light with a maximum emission wavelength of 430 nm to 480 nm.

[0056] In this specification, “(the organic layer) contains one or more organometallic compounds” is also interpreted as “(the organic layer) may contain one kind of organometallic compound belonging to the category of Chemical Formula 1, or two or more different kinds of organometallic compounds belonging to the category of Chemical Formula 1”. For example, the organic layer may contain only Compound 1 as the organometallic compound. At this time, Compound 1 is present in the light-emitting layer of the organic light-emitting device. Alternatively, the organic layer may contain Compound 1 and Compound 2 as the organometallic compounds. At this time, Compound 1 and Compound 2 are present in the same layer (for example, both Compound 1 and Compound 2 are present in the light-emitting layer). In this specification, “organic layer” is a term indicating a single and / or multiple layers interposed between the first electrode and the second electrode in an organic light-emitting device. The “organic layer” may include not only organic compounds but also organometallic complexes containing metals.

[0057] FIG. 1 is a cross-sectional view showing a schematic configuration of an organic light-emitting device according to an embodiment of the present invention. Hereinafter, with reference to FIG. 1, the structure and manufacturing method of an organic light-emitting device according to an embodiment of the present invention will be described as follows. The organic light-emitting device 10 has a structure in which a first electrode 11, an organic layer 15, and a second electrode 19 are sequentially stacked.

[0058] A substrate may be additionally disposed below the first electrode 11 or above the second electrode 19. As the substrate, a substrate generally used for organic light-emitting devices can be used, but a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness can be used.

[0059] The first electrode 11 is formed, for example, by providing a first electrode material on top of a substrate using a vapor deposition method or a sputtering method or the like. The first electrode 11 is also an anode. The first electrode material is selected from among materials having a high work function so that hole injection is easy. The first electrode 11 is also a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. As the first electrode material, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or the like can be used. Or, metals such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) can be used. The first electrode 11 can have a single-layer structure or a multilayer structure including two or more layers. For example, the first electrode 11 can have a three-layer structure of ITO / Ag / ITO, but is not limited thereto.

[0060] An organic layer 15 is disposed on top of the first electrode 11. The organic layer 15 may include a hole transport region, a light-emitting layer, and an electron transport region. The hole transport region is disposed between the first electrode 11 and the light-emitting layer. The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof. The hole transport region may include only a hole injection layer or only a hole transport layer. Or, the hole transport region can have a structure of a hole injection layer / hole transport layer or a hole injection layer / hole transport layer / electron blocking layer sequentially stacked from the first electrode 11.

[0061] When the hole transport region includes a hole injection layer, the hole injection layer can be formed on top of the first electrode 11 using various methods such as vacuum evaporation, spin coating, casting, and the LB (Langmuir-Blodgett) method. When forming the hole injection layer by vacuum evaporation, the evaporation conditions vary depending on the compound used as the hole injection layer material, the structure and thermal properties of the intended hole injection layer, etc. For example, the evaporation temperature is about 100 to about 500 °C, the degree of vacuum is about 10 -8 ~ about 10-3 torr, and the evaporation rate is selected from the range of about 0.01 to about 100 Å / sec, but is not limited thereto.

[0062] When forming the hole injection layer by spin coating, the coating conditions vary depending on the compound used as the hole injection layer material, the structure and thermal properties of the intended hole injection layer. The coating speed is about 2,000 rpm to about 5,000 rpm, and the heat treatment temperature for solvent removal after coating is selected from the range of about 80 °C to 200 °C, but is not limited thereto. The formation conditions of the hole transport layer and the electron blocking layer refer to the hole injection layer formation conditions.

[0063] The hole transport region may include, for example, at least one of m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4’,4”-tris(carbazol-9-yl)-triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), the compound represented by Chemical Formula 201 shown below, and the compound represented by Chemical Formula 202 shown below. TIFF0007713771000036.tif55143TIFF0007713771000037.tif98147 [Chemical formula] [Chemical formula]

[0064] In Chemical formula 201, Ar 101 and Ar 102 are, independently of one another, a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, and a pentacenylene group, and deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 60 alkyl group, a C2-C 60 alkenyl group, a C2-C 60 alkynyl group, a C1-C 60 alkoxy group, a C3-C 10 cycloalkyl group, a C3-C 10 cycloalkenyl group, a C1-C 10 heterocycloalkyl group, a C1-C 10 heterocycloalkenyl group, a C6-C 60 aryl group, a C6-C 60 aryloxy group, a C6-C 60 arylthio group, a C1-C 60Selected from among a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, and a pentacenylene group, which is substituted with at least one of a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group.

[0065] In Chemical Formula 201, xa and xb are each independently an integer of 0 to 5, or may also be 0, 1, or 2. For example, xa is 1 and xb is 0, but is not limited thereto.

[0066] In Chemical Formulas 201 and 202, the aforementioned R 101 ~R 108 、R 111 ~R 119 、and R 121 ~R 124 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 10 alkyl group (e.g., a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, etc.), and a C1-C 10 alkoxy group (e.g., a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, etc.), a C1-C alkyl group and a C1-C alkoxy group, which are substituted with one or more of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof, 10 and a C1-C 10 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 10 alkyl group, and C1-C 10 phenyl group, naphthyl group, anthracenyl group, fluorenyl group, and pyrenyl group, which are each substituted with one or more of the above, but are not limited thereto.

[0067] In Chemical Formula 201, R 109 is phenyl group, naphthyl group, anthracenyl group and pyridinyl group, and deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 alkyl group, C1-C 20 alkoxy group, phenyl group, naphthyl group, anthracenyl group, and pyridinyl group, which are each substituted with one or more of the above, and are selected from phenyl group, naphthyl group, anthracenyl group, and pyridinyl group.

[0068] According to one embodiment, the compound represented by Chemical Formula 201 is also represented by Chemical Formula 201A shown below, but is not limited thereto.

Chemical Formula

[0069] For example, the compound represented by Chemical Formula 201 and the compound represented by Chemical Formula 202 may include, but are not limited to, the following compounds HT1 to HT20.

Chemical Formula

Chem.

Chem.

Chem.

[0070] The thickness of the hole transport region is from about 100 Å to about 10,000 Å, for example, it may also be from about 100 Å to about 1,000 Å. If the hole transport region includes at least one of the hole injection layer and the hole transport layer, the thickness of the hole injection layer is from about 100 Å to about 10,000 Å, for example, from about 100 Å to about 1,000 Å, and the thickness of the hole transport layer is from about 50 Å to about 2,000 Å, for example, from about 100 Å to about 1,500 Å. When the thicknesses of the aforementioned hole transport region, hole injection layer, and hole transport layer satisfy the above ranges, satisfactory hole transport characteristics can be obtained without a substantial increase in the driving voltage. In addition to the substances as described above, the hole transport region may further contain a charge generating substance for improving conductivity.

[0071] The charge generating substance is uniformly or non-uniformly dispersed in the hole transport region. The charge generating substance is, for example, also a p-dopant. The p-dopant is one of, but not limited to, quinone derivatives, metal oxides, and cyano group-containing compounds. For example, non-limiting examples of the p-dopant include quinone derivatives such as tetracyanoquinonedimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), metal oxides such as tungsten oxide and molybdenum oxide, and cyano group-containing compounds such as the compound HT-D1 shown below, but are not limited thereto.

Chem.

[0072] The positive hole transport region may further include a buffer layer. The buffer layer compensates for the optical resonance distance based on the wavelength of the light emitted from the light emitting layer and plays a role in increasing the efficiency. A light emitting layer can be formed above the positive hole transport region by a method such as a vacuum evaporation method, a spin coating method, a casting method, or an LB method. When forming the light emitting layer by the vacuum evaporation method and the spin coating method, the evaporation conditions and coating conditions vary depending on the compound used, but generally, they are selected from within substantially the same condition range as the formation of the positive hole injection layer.

[0073] On the other hand, when the positive hole transport region includes an electron blocking layer, the electron blocking layer material is selected from among the substances used for the positive hole transport region as described above and the host substances described later, but is not limited thereto. For example, when the positive hole transport region includes an electron blocking layer, mCP described later can be used as the electron blocking layer material. The light emitting layer includes a host and a dopant, and the dopant includes an organometallic compound represented by Chemical Formula 1. The host may include at least one of TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, mCP, Compound H50, and Compound H51 shown below. TIFF0007713771000046.tif84142TIFF0007713771000047.tif26146

[0074] Alternatively, the host may further include a compound represented by Chemical Formula 301 shown below.

Chemical formula

[0075] In Chemical Formula 301, Ar 111 and Ar 112 are each independently A phenylene group, a naphthylene group, a phenanthrenylene group, and a pyrenylene group, and also selected from among phenylene groups, naphthylene groups, phenanthrenylene groups, and pyrenylene groups substituted with one or more of a phenyl group, a naphthyl group, and an anthracenyl group. In Chemical Formula 301, Ar 113 ~Ar 116 are, independently of one another, a C1-C 10 alkyl group, a phenyl group, a naphthyl group, a phenanthrenyl group, and a pyrenyl group, and also selected from among phenyl groups, naphthyl groups, phenanthrenyl groups, and pyrenyl groups substituted with one or more of a phenyl group, a naphthyl group, and an anthracenyl group.

[0076] In Chemical Formula 301, g, h, i, and j are, independently of one another, integers from 0 to 4, for example, 0, 1, or 2. In Chemical Formula 301, Ar 113 ~Ar 116 are, independently of one another, a C1-C alkyl group substituted with one or more of a phenyl group, a naphthyl group, and an anthracenyl group, 10 a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, and a fluorenyl group, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 60 alkyl group, a C2-C 60 alkenyl group, a C2-C 60 alkynyl group, a C1-C 60 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, and a fluorenyl group substituted with one or more of a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, and a fluorenyl group, and It is selected from among, but not limited to, 29128 of TIFF0007713771000049.tif.

[0077] Alternatively, the host may contain a compound represented by Chemical Formula 302 shown below. [Chemical Formula]

[0078] In Chemical Formula 302, Ar 122 ~Ar 125 For the detailed description regarding 113 Ar of Chemical Formula 301, refer to the description of In Chemical Formula 302, Ar 126 and Ar 127 are each independently also a C1-C 10 alkyl group (for example, a methyl group, an ethyl group, or a propyl group). In Chemical Formula 302, k and l are each independently also an integer from 0 to 4. For example, k and l are also 0, 1, or 2. When the organic light-emitting element is a full-color organic light-emitting element, the light-emitting layer is patterned into a red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer. Alternatively, various modifications are possible, such that the light-emitting layer has a structure in which a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer are stacked, so that white light can be emitted.

[0079] When the light-emitting layer contains a host and a dopant, the content of the dopant is generally selected from 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. The thickness of the light-emitting layer is about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the light-emitting layer satisfies the range as described above, excellent light-emitting characteristics can be exhibited without a substantial increase in the driving voltage.

[0080] Next, an electron transport region is disposed on top of the light-emitting layer. The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. For example, the electron transport region can have a structure of hole blocking layer / electron transport layer / electron injection layer or electron transport layer / electron injection layer, but is not limited thereto. The electron transport layer can have a single-layer structure or a multi-layer structure containing two or more different substances. Refer to the formation conditions of the hole injection layer for the formation conditions of the hole blocking layer, electron transport layer, and electron injection layer in the electron transport region.

[0081] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP, Bphen, and BAlq shown below, but is not limited thereto.

Chemical formula

[0082] The thickness of the hole blocking layer is about 20 Å to about 1,000 Å, for example, also about 30 Å to about 300 Å. When the thickness of the hole blocking layer satisfies the above range, excellent hole blocking characteristics can be obtained without a substantial increase in driving voltage. The electron transport layer may further include at least one of the aforementioned BCP, Bphen, and Alq3, BAlq, TAZ, and NTAZ shown below. TIFF0007713771000052.tif77137

[0083] Alternatively, the electron transport layer may include at least one of the compounds ET1 to ET25 shown below, but is not limited thereto.

Chemical formula

Chemical formula

Chemical formula

[0084] The thickness of the electron transport layer is from about 100 Å to about 1,000 Å, for example, from about 150 Å to about 500 Å. When the thickness of the electron transport layer satisfies the range as described above, satisfactory electron transport characteristics can be obtained without a substantial increase in the driving voltage.

[0085] In addition to the substances as described above, the electron transport layer may further contain a metal-containing substance. The metal-containing substance may contain a Li complex. The Li complex may contain, for example, the compound ET-D1 (lithium quinolate (LiQ)) or ET-D2 shown below. [Chemical formula]

[0086] Further, the electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 19. The electron injection layer may contain at least one selected from LiF, NaCl, CsF, Li2O, and BaO. The thickness of the electron injection layer is from about 1 Å to about 100 Å, for example, from about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the range as described above, satisfactory electron injection characteristics can be obtained without a substantial increase in the driving voltage.

[0087] The second electrode 19 is provided on top of the organic layer 15. The second electrode 19 is a cathode. As the material for the second electrode 19, a metal, an alloy, an electrically conductive compound, and combinations thereof having a relatively low work function can be used. As specific examples, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. can be used as the material for forming the second electrode 19. Alternatively, in order to obtain a front light-emitting element, various modifications are possible, such as forming a transmissive second electrode 19 by using ITO or IZO. As described above, the organic light-emitting element has been described with reference to FIG. 1, but the present invention is not limited thereto.

[0088] According to still another aspect, a diagnostic composition containing one or more organic metal compounds represented by Chemical Formula 1 can be provided. Since the organic metal compound represented by Chemical Formula 1 can provide high luminous efficiency, the diagnostic composition containing the organic metal compound can have high diagnostic efficiency. The diagnostic composition can be variously applied to various diagnostic kits, diagnostic reagents, biosensors, biomarkers, etc.

[0089] In the present specification, C1-C 60 The alkyl group means a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms. Specific examples include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, a hexyl group, etc. In the present specification, C1-C 60 The alkylene group means a divalent group having the same structure as the C1-C 60 alkyl group. In the present specification, C1-C 60 The alkoxy group means a monovalent group having the chemical formula -OA 101 (where A 101 is the C1-C 60 alkyl group), and specific examples thereof include a methoxy group, an ethoxy group, an isopropyloxy group, etc.

[0090] In the present specification, C2-C 60Alkenyl groups are C2-C 60 It has a structure containing one or more carbon-carbon double bonds in the middle or at the end of the alkyl group, and specific examples thereof include ethenyl, propenyl, and butenyl groups. As used herein, C2-C 60 The alkenylene group is C2-C 60 It means a divalent group having the same structure as an alkenyl group. As used herein, C2-C 60 Alkynyl groups are C2-C 60 It has a structure containing one or more carbon-carbon triple bonds in the middle or at the end of the alkyl group, and specific examples thereof include an ethynyl group and a propynyl group. As used herein, C2-C 60 The alkynylene group is C2-C 60 It means a divalent group having the same structure as an alkynyl group.

[0091] As used herein, C3-C 10 Cycloalkyl groups are C3-C 10 It means a monovalent saturated hydrocarbon monocyclic group, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. As used herein, C3-C 10 The cycloalkylene group is C3-C 10 It means a divalent group having the same structure as a cycloalkyl group. As used herein, C1-C 10 Heterocycloalkyl groups are C1-C10 alkyl groups containing at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom. 10 It means a monovalent monocyclic group, specific examples of which include a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and the like. As used herein, C1-C 10 The heterocycloalkylene group is C1-C 10 It means a divalent group having the same structure as a heterocycloalkyl group.

[0092] As used herein, C3-C 10The cycloalkenyl group is a monovalent monocyclic group having at least one carbon-carbon double bond in the ring, but having no aromaticity, and specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. 10 In this specification, the cycloalkenyl group is a monovalent monocyclic group having at least one carbon-carbon double bond in the ring, but having no aromaticity, and specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. In this specification, C3-C 10 The cycloalkenylene group means a divalent group having the same structure as the cycloalkenyl group. 10 In this specification, the cycloalkenylene group means a divalent group having the same structure as the cycloalkenyl group. In this specification, C1-C 10 The heterocycloalkenyl group is a monovalent monocyclic group containing at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom and having at least one double bond in the ring. 10 In this specification, the heterocycloalkenyl group is a monovalent monocyclic group containing at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom and having at least one double bond in the ring. C1-C 10 Specific examples of the heterocycloalkenyl group include a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like. In this specification, C1-C 10 The heterocycloalkenylene group means a divalent group having the same structure as the heterocycloalkenyl group. 10 In this specification, the heterocycloalkenylene group means a divalent group having the same structure as the heterocycloalkenyl group.

[0093] In this specification, C6-C 60 The aryl group means a monovalent group having a carbocyclic aromatic system, C6-C 60 In this specification, the aryl group means a monovalent group having a carbocyclic aromatic system, C6-C 60 The arylene group means a divalent group having a carbocyclic aromatic system. 60 In this specification, the arylene group means a divalent group having a carbocyclic aromatic system. C6-C 60 Specific examples of the aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a chrysenyl group, and the like. C6-C 60 When the aryl group and the C6-C60 arylene group contain two or more rings, the two or more rings may be fused to each other. C7-C 60 The alkylaryl group means an aryl group substituted with at least one C1-C 60 alkyl group. 60 In this specification, the alkylaryl group means an aryl group substituted with at least one C1-C alkyl group.

[0094] In this specification, C1-C 60 The heteroaryl group contains at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and is a monovalent group having a C1-C 60 cyclic aromatic system, and C1-C 60 The heteroarylene group contains at least one heteroatom selected from N, O, P, and S as a ring-forming atom, and is a divalent group having a C1-C 60 carbocyclic aromatic system. C1-C 60 Specific examples of the heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and the like. C1-C 60 When the heteroaryl group and the C1-C 60 heteroarylene group contain two or more rings, the two or more rings may be fused to each other. C2-C 60 The alkylheteroaryl group means a C1-C 60 heteroaryl group substituted with at least one C1-C 60 alkyl group.

[0095] In this specification, C6-C 60 The aryloxy group is -OA 102 (where A 102 is a C6-C 60 aryl group), and C6-C 60 The arylthio group is -SA 103 (where A 103 is a C6-C 60 aryl group). In this specification, the monovalent non-aromatic condensed polycyclic group means a monovalent group in which two or more rings are condensed to each other, containing only carbon as a ring-forming atom, and the whole molecule has non-aromaticity (for example, having 8 to 60 carbon atoms). Specific examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group and the like. As used herein, the divalent non-aromatic condensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

[0096] As used herein, the monovalent non-aromatic hetero-condensed polycyclic group means a monovalent group in which two or more rings are condensed with each other, and which contains, in addition to carbon as a ring-forming atom, a hetero atom selected from among N, O, P, Si, and S, and the whole molecule has non-aromaticity (for example, having 1 to 60 carbon atoms). The monovalent non-aromatic hetero-condensed polycyclic group includes a carbazolyl group and the like. As used herein, the divalent non-aromatic hetero-condensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic hetero-condensed polycyclic group.

[0097] As used herein, C5-C 30 The carbocyclic group represents a saturated or unsaturated cyclic group having only 5 to 30 carbons as ring-forming atoms. C5-C 30 The carbocyclic group is also a monocyclic group or a polycyclic group. As used herein, C1-C 30 The heterocyclic group represents a saturated or unsaturated cyclic group having at least one hetero atom selected from among N, O, P, Si, and S in addition to 1 to 30 carbons as ring-forming atoms. C1-C 30 The heterocyclic group is also a monocyclic group or a polycyclic group.

[0098] The above-mentioned substituted C5-C 30 carbocyclic group, substituted C1-C 30 heterocyclic group, substituted C1-C 60 alkyl group, 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 10Heterocycloalkenyl 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 At least one of the substituents of alkylheteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic hetero-condensed polycyclic group is Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, and C1-C 60 Alkoxy group, Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid 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, C7-C 60 Alkylaryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, C2-C 60 Alkylheteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic hetero-condensed polycyclic group, -N(Q 11 )(Q 12 ), -Si(Q 13 )(Q 14 )(Q15 ), -B(Q 16 )(Q 17 ), and -P(=O)(Q 18 )(Q 19 ), and at least one selected from the group consisting of a C1-C 60 alkyl group, a C2-C 60 alkenyl group, a C2-C 60 alkynyl group, and a C1-C 60 alkoxy group, a C3-C 10 cycloalkyl group, a C1-C 10 heterocycloalkyl group, a C3-C 10 cycloalkenyl group, a C1-C 10 heterocycloalkenyl group, a C6-C 60 aryl group, a C7-C 60 alkylaryl group, a C6-C 60 aryloxy group, a C6-C 60 arylthio group, a C1-C 60 heteroaryl group, a C2-C 60 alkylheteroaryl group, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic hetero-fused polycyclic group, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C1-C 60 alkyl group, a C2-C 60 alkenyl group, a C2-C 60 alkynyl group, a C1-C 60 alkoxy group, a C3-C 10 cycloalkyl group, a C1-C 10 heterocycloalkyl group, a C3-C 10 cycloalkenyl group, a C1-C 10 heterocycloalkenyl group, a C6-C 60 aryl group, a C7-C 60 alkylaryl group, a C6-C 60 aryloxy group, a C6-C 60 arylthio group, a C1-C 60 heteroaryl group, a C2-C60 An alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic hetero-condensed 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 ), substituted with at least one selected from the group consisting of 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, C7-C 60 alkylaryl group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C1-C 60 heteroaryl group, C2-C 60 alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group, and -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、and -P(=O)(Q 38 )(Q 39 ), selected from the group consisting of the aforementioned Q1 to Q9, Q 11 ~Q 19 、Q 21 ~Q 29 、and Q 31 ~Q 39 are, independently of one another, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, C1-C 60 alkyl group, deuterium·C1-C 60 alkyl group·C6-C60 A C1-C substituted with at least one of the aryl groups 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, deuterium·C1-C 60 alkyl group·C6-C 60 A C6-C substituted with at least one of the aryl groups 60 aryl group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C1-C 60 heteroaryl group, C2-C 60 An alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group are also selected from among them.

[0099] Hereinafter, synthesis examples and examples will be given, and the compounds and organic light-emitting elements according to one embodiment of the present invention will be described more specifically. However, the present invention is not limited to the following synthesis examples and examples. In the following synthesis examples, in the expression "using 'B' instead of 'A'", the usage amount of "B" and the usage amount of "A" are the same on a molar basis.

[0100] <<Example>> <Synthesis Example 1: Synthesis of Compound 1> (1) Synthesis of Intermediate (A) TIFF0007713771000058.tif751281-(3-Bromophenyl)-1H-benzo[2,3]benzofuro[4,5-d]imidazole (5.0 g, 13.76 mmol), 9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazol-2-ol (4.35 g, 13.76 mmol), copper(I) iodide (0.52 g, 2.75 mmol), picolinic acid (0.68 g, 5.5 mmol) and tripotassium phosphate (8.76 g, 41.28 mmol) were mixed with 90 mL of dimethyl sulfoxide (DMSO) and then stirred at 120 °C for 18 h. After completion of the reaction, the mixture was cooled to room temperature, and the organic layer extracted using saturated ammonium chloride (saturated NH4Cl) and ethyl acetate (EA) was dried over anhydrous magnesium sulfate (anhydrous MgSO4), filtered, and then concentrated under reduced pressure. Silica gel column chromatography was performed on the resulting product to obtain intermediate (A) (4.04 g, 8.26 mmol, yield = 60%). LC-Mass (calculated value: 598.24 g / mol, measured value: M +1 = 599 g / mol)

[0101] (2) Synthesis of intermediate (B) TIFF0007713771000059.tif41129 Intermediate (A) (4.04 g, 8.26 mmol) and methyl iodide (3.52 g, 24.78 mmol) were mixed with 40 mL of toluene and then stirred at 60 °C for 12 h. After completion of the reaction, the mixture was cooled to room temperature, and silica gel column chromatography was performed on the resulting product obtained by concentration under reduced pressure to obtain intermediate (B) (4.89 g, 6.61 mmol, yield = 80%).

[0102] (3) Synthesis of compound 1 Intermediate (B) (4.89 g, 6.61 mmol), Pt(COD)Cl2 (2.72 g, 7.27 mmol), and sodium acetate (1.63 g, 19.83 mmol) were mixed with 220 mL of tetrahydrofuran (THF), and then stirred at 120 °C for 48 hours. After completion of the reaction, the mixture was cooled to room temperature, and the organic layer extracted using saturated ammonium chloride (saturated NH4Cl) and dichloromethane (DCM) was dried over anhydrous magnesium sulfate (anhydrous MgSO4), filtered, and then concentrated under reduced pressure. Silica gel column chromatography was performed on the resulting product to obtain Compound 1 (1.87 g, 2.31 mmol, yield = 35%). LC-Mass (calculated value: 805.20 g / mol, measured value: M +1 = 806 g / mol)

[0103] <Synthesis Example 2: Synthesis of Compound 49> (1) Synthesis of Intermediate (C) 3-(3-Bromophenyl)-3H-benzo[2,3]benzofuro[6,7-d]imidazole (5.0 g, 13.76 mmol), 9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazol-2-ol (4.35 g, 13.76 mmol), copper(I) iodide (0.52 g, 2.75 mmol), picolinic acid (0.68 g, 5.5 mmol), and tripotassium phosphate (8.76 g, 41.28 mmol) were mixed with 90 mL of DMSO, and then stirred at 120 °C for 18 hours. After completion of the reaction, the mixture was cooled to room temperature, and the organic layer extracted using saturated ammonium chloride (saturated NH4Cl) and ethyl acetate (EA) was dried over anhydrous magnesium sulfate (anhydrous MgSO4), filtered, and then concentrated under reduced pressure. Silica gel column chromatography was performed on the resulting product to obtain Intermediate (C) (4.38 g, 8.94 mmol, yield = 65%). LC-Mass(Calculated value: 598.24 g / mol, Measured value: M +1 = 599 g / mol)

[0104] (2) Synthesis of Intermediate (D) TIFF0007713771000062.tif42128 Intermediate (C) (4.38 g, 8.94 mmol) and methyl iodide (3.81 g, 26.82 mmol) were mixed with 40 mL of toluene and then stirred at 60 °C for 12 hours. After completion of the reaction, the mixture was cooled to room temperature and then concentrated under reduced pressure. Silica gel column chromatography was performed on the resulting product to obtain Intermediate (D) (5.36 g, 7.24 mmol, Yield = 81%).

[0105] (3) Synthesis of Compound 49 TIFF0007713771000063.tif43132 Intermediate (D) (5.36 g, 7.24 mmol), Pt(COD)Cl2 (2.98 g, 7.96 mmol) and sodium acetate (1.76 g, 21.72 mmol) were mixed with 230 mL of THF and then stirred at 120 °C for 48 hours. After completion of the reaction, the mixture was cooled to room temperature, and the organic layer extracted using saturated ammonium chloride (saturated NH4Cl) and dichloromethane (DCM) was dried over anhydrous magnesium sulfate (anhydrous MgSO4), filtered, and then concentrated under reduced pressure. Silica gel column chromatography was performed on the resulting product to obtain Compound 49 (2.04 g, 2.53 mmol, Yield = 35%). LC-Mass(Calculated value: 805.20 g / mol, Measured value: M +1 = 806 g / mol)

[0106] <<Evaluation Example 1: Evaluation of Maximum Emission Wavelength, Chromaticity Coordinates and Full Width at Half Maximum (FWHM)>> Compound 1 was diluted to a concentration of 10 mM in toluene, and then using an ISC PC1 spectrofluorometer equipped with a xenon lamp, the PL (photoluminecscence) spectrum was measured at room temperature, from which the maximum emission wavelength, color coordinates, and full width at half maximum of Compound 1 were evaluated. This was repeated for Compound 49 and Compound A, and the results are shown in Table 2.

[0107] <<Evaluation Example 2: Decay Time Measurement>> On a quartz substrate, Compound 1 was vacuum co-evaporated with the host used in the examples at a weight ratio of 2 wt% under a vacuum of 10-7 torr to produce a film with a thickness of 40 nm. For each film, using a FluoTime 300, a TRPL measurement instrument from PicoQuant, and a PLS340, a pumping source from PicoQuant (excitation wavelength = 340 nm, spectral width = 20 nm), after evaluating the PL spectrum at room temperature, the main peak wavelength of the spectrum was determined, and by the photon pulse (pulse width = 500 ps) applied by the PLS340 to each film, the number of photons emitted at the wavelength of the main peak from each film was repeatedly measured over time based on TCSPC (time-correlated single photon counting) to obtain a TRPL curve for which fitting was sufficiently possible. One or more exponential decay functions were fitted to the results obtained therefrom, and for each film, each T decay (Ex), that is, the decay time was determined, and the results are described in Table 2 respectively.

[0108] The function used for fitting is as shown in Equation 1 below, and the average value of T obtained from each exponential decay function used for fitting was taken as T decay of decay (Ex). At this time, between the measurement time for obtaining the TRPL curve and the same measurement time, the same measurement was repeated one more time in the dark state (a state where the pumping signal incident on a predetermined film was blocked) to obtain a baseline or background signal curve, which was used as the baseline for fitting. This was repeated for Compound 49 and Compound A, and the results are shown in Table 2.

Number

[0109] <<Evaluation Example 3: Evaluation of Luminescence Quantum Efficiency (PLQY)>> After mixing a CH2Cl2 solution of PMMA, 5 wt% of CBP, and Compound 1, the resulting product was coated on a quartz substrate using a spin coater, heat-treated in an oven at 80 °C, and then cooled to room temperature to produce a film. The luminescence quantum yields in the film were evaluated for Compound 1 using a Hamamatsu Photonics absolute PL quantum yield measurement system equipped with a xenon light source, a monochromator, a photonic multichannel analyzer, and an integrating sphere, and adopting PLQY measurement software (Hamamatsu Photonics Co., Ltd., Shizuoka). This was repeated for Compound 49 and Compound A, and the results are shown in Table 2.

[0110]

Table 2

[0111] <Example 1> The ITO glass substrate was cut into a size of 50 mm × 50 mm × 0.5 mm, ultrasonically cleaned in acetone, isopropyl alcohol, and pure water for 15 minutes each, and then UV ozone cleaned for 30 minutes. Next, m-MTDATA was deposited on the ITO electrode (anode) on the glass substrate at a deposition rate of 1 Å / sec to form a 600 Å thick hole injection layer. On the hole injection layer, α-NPD was deposited at a deposition rate of 1 Å / sec to form a 250 Å thick hole transport layer. On the hole transport layer, Compound 1 (dopant) and CBP (host) were co-deposited at deposition rates of 0.1 Å / sec and 1 Å / sec, respectively, to form a 400 Å thick light-emitting layer.

[0112] On the light-emitting layer, BAlq was deposited at a deposition rate of 1 Å / sec to form a 50 Å thick hole blocking layer. On the hole blocking layer, Alq3 was deposited to form a 300 Å thick electron transport layer. Then, LiF was deposited on the upper part of the electron transport layer to form a 10 Å thick electron injection layer. After that, Al was vacuum deposited on the electron injection layer to form a 1,200 Å thick second electrode (cathode), thereby fabricating an organic light-emitting device having the structure of ITO / m-MTDATA(600 Å) / α-NPD(250 Å) / CBP + Compound 1(10%)(400 Å) / BAlq(50 Å) / Alq3(300 Å) / LiF(10 Å) / Al(1,200 Å). TIFF0007713771000067.tif97162

[0113] <Example 2, and Comparative Examples 1 and 2> An organic light-emitting device was fabricated using the same method as in Example 1, except that the compounds described in Table 3 were used as dopants instead of Compound 1 when forming the light-emitting layer.

[0114] <<Evaluation Example 4: Characteristics Evaluation of Organic Light-Emitting Devices>> For each of the organic light-emitting devices fabricated in Examples 1 and 2 and Comparative Examples 1 and 2, the EL spectrum, driving voltage, and external quantum emission efficiency were evaluated. The specific evaluation methods are as follows, and the results are as shown in Table 3 below. The driving voltages and external quantum efficiencies in Table 3 are shown as relative values (%) compared to the driving voltage and external quantum efficiency of the organic light-emitting device of Comparative Example D.

[0115] (1) Measurement of the change in current density due to voltage change For the fabricated organic light-emitting device, while increasing the voltage from 0 V to 10 V, a current / voltage meter (Keithley 2400) was used to measure the current value flowing through the unit device, and the measured current value was divided by the area to obtain the result. (2) Measurement of the change in luminance due to voltage change For the fabricated organic light-emitting device, while increasing the voltage from 0 V to 10 V, a luminance meter (Minolta Cs-1000A) was used to measure the luminance at that time to obtain the result. (3) EL spectrum measurement For the fabricated organic light-emitting device, a luminance meter (Minolta Cs-1000A) was used, and after measuring the EL spectrum when the luminance was 500 cd / m 2 the maximum emission wavelength was evaluated. (4) External quantum efficiency measurement It was evaluated using a current / voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A).

[0116]

Table 3

[0117] Furthermore, the present invention is not limited to the above-described embodiments (examples). Various modifications can be made without departing from the technical scope of the present invention.

Explanation of Reference Numerals

[0118] 10 Organic light-emitting element 11 First electrode 15 Organic layer 19 Second electrode

Claims

1. An organometallic compound, characterized in that it is represented by any one selected from the following chemical formulas 12-1 to 12-6. 【Chemical Formula 12-1】 【Chemical Formula 12-2】 [[Chemical 12-3]] 【Chemical Formula 12-4】 【Chemical Formula 12-5】 【Chemical Formula 12-6】 In the chemical formulas 12-1 to 12-6, M １ is platinum (Pt), X10, X ２０ and X30 are, independently of each other, C or N, T2 is selected from a single bond and *-O-*', R40 is selected from hydrogen, deuterium, a substituted or unsubstituted C １ -C ４ alkyl group and an unsubstituted C ６ aryl group, Y51 is selected from *-O-*', *-S-*' and *-N(R ５ )-*', R ５ is an unsubstituted C １ alkyl group, and X １１ is C(R １１ ), X １２ is C(R １２ ), X １３ is C(R １３ ), X １４ is C(R １４ ), and X ２１ is C(R ２１ ), and X ２２ is C(R ２２ ), and X ２３ is C(R ２３ ), and X ２４ is C(R ２４ ), and X ２５ is C(R ２５ ), and X ２６ is C(R ２６ ), and X ３１ is C(R ３１ ), and X ３２ is C(R ３２ ), and X ３３ is C(R ３３ ), and X ５１ is C(R ５１ ), X ５２ is C(R ５２ ), X ５３ is C(R ５３ ), X ５４ is C(R ５４ ), X ５５ is C(R ５５ ), X ５６ is C(R ５６ ) or N, R11 to R14, R21 to R26, R31 to R33 and R ５１ to R ５６ are the same as R40, The replaced C ５ -C ３０ A carbocyclic group, a replaced C １ -C ３０ At least one of the substituents of the heterocyclic group is deuterium and a C １ -C ４ selected from among alkyl groups, where * and *' are bonding sites with adjacent atoms, respectively.

2. The organometallic compound according to Claim 1, characterized in that it is selected from the following Compounds 1 to 72. 【Chemical comp1-12】 【Chemical formula 13-24】 【Chemical formula 25-36】 【Chemical formula 37-48】 【Chemical formula 49-60】 [Chemical Formula 61-72]

3. 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 contains one or more of the organometallic compounds according to Claim 1 or 2, characterized in that it is an organic light-emitting device.

4. The first electrode is an anode, the second electrode is a cathode, the organic layer further includes a hole transport region interposed between the first electrode and the light-emitting layer and an electron transport region interposed between the light-emitting layer and the second electrode, the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, the organic light-emitting device according to Claim 3, characterized in that the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

5. The organic light-emitting device according to Claim 3, characterized in that the organometallic compound is contained in the light-emitting layer.

6. The light-emitting layer further includes a host, the organic light-emitting device according to Claim 5, characterized in that the content of the host is larger than the content of the organometallic compound.

7. The organic light-emitting device according to Claim 5, characterized in that the light-emitting layer emits blue light with a maximum emission wavelength of 430 nm to 480 nm.

8. A diagnostic composition characterized by containing one or more of the organometallic compounds according to Claim 1 or 2.

Images