KR-102962656-B1 - Organometallic compound, organic light emitting device including the same and a composition for diagnosing including the same

Abstract

An organometallic compound, an organic light-emitting device including the organometallic compound, and a diagnostic composition including the organometallic compound are disclosed.

Inventors

• 박범우
• 김상동
• 김소연
• 아라타니 스케카즈
• 이정인
• 황규영
• 곽윤현
• 권오현

Assignees

• 삼성전자주식회사

Dates

Publication Date

20260507

Application Date

20240429

Claims (15)

1. Organometallic compound represented by the following chemical formula 1: <Chemical Formula 1> In the above chemical formula 1, M is palladium (Pd), platinum (Pt), or gold (Au), and In the above Chemical Formula 1, the bond between A1 and M and the bond between A4 and M are covalent bonds, and the bond between A2 and M and the bond between A3 and M are coordinate bonds, and A1 in the above chemical formula 1 is represented by the following chemical formula A1-2(1) or A1-2(56), and Among the above chemical formulas A1-2(1) and A1-2(56), a15 is selected from integers 0 to 5, and a17 is selected from integers 0 to 7, and * is the binding site with M in Chemical Formula 1, and *' is the binding site with T1 in Chemical Formula 1, and A2 in the above chemical formula 1 is represented by the following chemical formula A2-2 (9), and Among the above chemical formula A2-2(9), X 2 is N, X 21 is N(R 21 ), and a23 is selected from integers 0 to 3, and * is the binding site with M in Chemical Formula 1, *' is the binding site with T1 in Chemical Formula 1, and *" is the binding site with T2 in Chemical Formula 1, and A3 in the above chemical formula 1 is represented by the following chemical formula A3-1 (1) or A3-2 (25), and Among the above chemical formulas A3-1(1) and A3-2(25), X 3 is N, and a35 is selected from integers 0 to 5, and a33 are independently selected from integers 0 to 3, and * is the binding site with M in Chemical Formula 1, and *" is the binding site with T2 in Chemical Formula 1, and *' is the binding site with T3 in Chemical Formula 1, and In the above chemical formula 1, A4 is a first atom bonded to M or a non-cyclic moiety containing a first atom bonded to M, and The first atom is B, P, Si, O, or S, and In the above chemical formula 1, T1 and T2 are each single bonds, and In the above chemical formula 1, T3 is selected from a single bond, *-C(=O)-*' and *-C(=S)-*', and * and *' are each bonding sites with neighboring atoms, and In the above formulas A1-2(1), A1-2(56), A2-2(9), A3-1(1) and A3-2(25), R1 to R3 and R21 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5 , hydroxyl group, cyano group, nitro group, substituted or unsubstituted C1 - C60 alkyl group, substituted or unsubstituted C2 - C60 alkenyl group, substituted or unsubstituted C2 - C60 alkynyl group, substituted or unsubstituted C1 - C60 alkoxy group, substituted or unsubstituted C3 - C10 cycloalkyl group, substituted or unsubstituted C1 - C10 heterocycloalkyl group, substituted or unsubstituted C3 - C10 cycloalkenyl group, substituted or unsubstituted C1 - C10 Selected from heterocycloalkenyl groups, substituted or unsubstituted C6 - C60 aryl groups, substituted or unsubstituted C1 - C60 heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic groups, -N( Q1 )( Q2 ), -Si( Q3 )( Q4 )( Q5 ), -B( Q6 )( Q7 ), and -P(=O)( Q8 )( Q9 ), and In the above chemical formula 1, A1 and A4 are not connected to each other, and The substituents of the above-mentioned substituted C1 - C60 alkyl group, substituted C2 - C60 alkenyl group, substituted C2 - C60 alkynyl group, substituted C1 - C60 alkoxy group, substituted C3 - C10 cycloalkyl group, substituted C1 - C10 heterocycloalkyl group, substituted C3 - C10 cycloalkenyl group, substituted C1 - C10 heterocycloalkenyl group, substituted C6 - C60 aryl group, substituted C1 - C60 heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic heterocondensed polycyclic group are: Deuterium, -F, -Cl, -Br, -I, -CD3 , -CD2H , -CDH2, -CF3 , -CF2H , -CFH2 , hydroxyl group , cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1 - C60 alkyl group, C2 - C60 alkenyl group, C2 - C60 alkynyl group and C1 - C60 alkoxy group; Deuterium, -F, -Cl, -Br, -I, -CD3 , -CD2H , -CDH2, -CF3 , -CF2H , -CFH2 , hydroxyl group , cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C3 - C10 cycloalkyl group, C1 - C10 heterocycloalkyl group, C3 - C10 cycloalkenyl group, C1 - C10 heterocycloalkenyl group, C6 - C60 aryl group, C6 - C60 aryloxy group, C6 - C60 arylthio group, C1 - C60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent A C1-C60 alkyl group, C2-C60 alkenyl group, C2-C60 alkynyl group and C1- C60 alkoxy group substituted with at least one selected from a non- aromatic heterocondensed polycyclic group, -N( Q11 )( Q12 ), -Si ( Q13 )( Q14 )( Q15 ), -B ( Q16 )( Q17 ), and -P ( = O)( Q18 ) ( Q19 ); C3 - C10 cycloalkyl group, C1 - C10 heterocycloalkyl group, C3 - C10 cycloalkenyl group, C1 - C10 heterocycloalkenyl group, C6 - C60 aryl group, C6 - C60 aryloxy group, C6 - C60 arylthio group, C1 - C60 heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic heterocondensed polycyclic group; Deuterium, -F, -Cl, -Br, -I, -CD3 , -CD2H , -CDH2, -CF3 , -CF2H , -CFH2 , hydroxyl group , cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1 - C60 alkyl group, C2 - C60 alkenyl group, C2 - C60 alkynyl group, C1 - C60 alkoxy group, C3 - C10 cycloalkyl group, C1 - C10 heterocycloalkyl group, C3 - C10 cycloalkenyl group, C1 - C10 heterocycloalkenyl group, C6 - C60 aryl group, C6 - C60 aryloxy group, C6 - C60 aryltio group, C1 - C60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, substituted with at least one selected from -N( Q21 )( Q22 ), -Si( Q23 )( Q24 )( Q25 ), -B( Q26 )( Q27 ), and -P(=O)( Q28 )( Q29 ), C3 - C10 cycloalkyl group, C1 - C10 heterocycloalkyl group, C3 - C10 cycloalkenyl group, C1 - C10 heterocycloalkenyl group, C6 - C60 aryl group, C6 - C60 aryloxy group, C6 - C60 Arylthio group, C1 – C60 heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic heterocondensed 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 among, The above Q1 to Q9 , Q11 to Q19 , Q21 to Q29 , and Q31 to Q39 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1 - C60 alkyl group, deuterium, C1 - C60 alkyl group substituted with at least one of C6 - C60 aryl group and C6 - C60 alkenyl group, C2 - C60 alkynyl group, C2 - C60 alkoxy group, C3 - C10 cycloalkyl group, C1 - C10 heterocycloalkyl group, C It is selected from among a 3 - C10 cycloalkenyl group, a C1 - C10 heterocycloalkenyl group, a C6 - C60 aryl group, a deuterium, a C6 - C60 alkyl group and a C6 - C60 aryl group substituted with at least one of a C6 - C60 aryl group, a C6 - C60 aryloxy group, a C6 - C60 arylthio group, a C1 - C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocondensed polycyclic group.
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4. In paragraph 1, The above R 1 to R 3 and R 21 are independently of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, -SF5, C1 - C20 alkyl group and C1 - C20 alkoxy group; Deuterium , -F, -Cl, -Br, -I, -CD3 , -CD2H , -CDH2, -CF3 , -CF2H , -CFH2 , hydroxyl group, cyano group, nitro group, C1 - C10 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 pyrimidinyl group substituted with at least one, C1 - C20 alkyl group and C1 - C20 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, pyrroleyl group, thiophenyl group, furanyl group, imidazoleyl group, pyrazolyl group, thiazoleyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indoleyl group, indazoleyl group, furinyl group, Quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazoleyl group, phenanthrolinyl group, benzimidazoleyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazoleyl group, benzoxazoleyl group, isobenzoxazoleyl group, triazoleyl group, tetrazoleyl group, oxadiazoleyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazoleyl group, dibenzocarbazoleyl group, imidazopyridinyl group and imidazopyrimidinyl group; Deuterium , -F, -Cl, -Br, -I, -CD3 , -CD2H , -CDH2, -CF3 , -CF2H , -CFH2 , hydroxyl group, cyano group, nitro group, C1 - C20 alkyl group, C1 - C20 alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cycloheptenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrroleyl group, thiophenyl group, furanyl group, Imidazole single group, pyrazol single group, thiazole single group, isothiazol single group, oxazol single group, isoxazol single group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindole single group, indole single group, indazole single group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazole single group, phenanthrolinyl group, benzimidazole single group, benzofuranyl group, benzothiophenyl group, isobenzothiazol single group, benzoxazol single group, isobenzoxazol single group, triazole single group, tetrazol single group, oxadiazole single group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilol single 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, pyrroleyl group, thiophenyl group, furanyl group, imidazoleyl group, pyrazolyl group, thiazoleyl group, isothiazolyl group, substituted with at least one selected from benzocarbazoleyl group, dibenzocarbazoleyl group, imidazopyridinyl group, imidazopyridinyl group and -Si(Q 33 )(Q 34 )(Q 35 ), Oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indoleyl group, indazoleyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazoleyl group, phenanthrolinyl group, benzimidazoleyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazoleyl group, benzoxazoleyl group, isobenzoxazoleyl group, triazoleyl group, tetrazolyl group, oxadiazoleyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazoleyl group, dibenzocarbazoleyl group, imidazopyridinyl group and imidazopyrimidinyl group; and -N(Q 1 )(Q 2 ), -Si(Q 3 )(Q 4 )(Q 5 ), -B(Q 6 )(Q 7 ) and -P(=O)(Q 8 )(Q 9 ); Selected from among, Q 1 to Q 9 and Q 33 to Q 35 independently of each other, -CH 3 , -CD 3 , -CD 2 H, -CDH 2 , -CH 2 CH 3 , -CH 2 CD 3 , -CH 2 CD 2 H, -CH 2 CDH 2 , -CHDCH 3 , -CHDCD 2 H, -CHDCDH 2 , -CHDCD 3 , -CD 2 CD 3 , -CD 2 CD 2 H and -CD 2 CDH 2 ; 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, phenyl group and naphthyl group; and 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, phenyl group, and naphthyl group substituted with at least one selected from deuterium, C1-C10 alkyl groups and phenyl groups; Organometallic compounds selected from among.
5. In paragraph 1, The above R1 to R3 and R21 are independently selected from hydrogen, deuterium, -F, cyano group, nitro group, -SF5 , -CH3 , -CD3, -CD2H , -CDH2 , -CF3 , -CF2H , -CFH2 , the group represented by the following chemical formulas 9-1 to 9-19 , the group represented by the following chemical formulas 10-1 to 10-156, -N( Q1 )( Q2 ), -Si( Q3 )( Q4 )( Q5 ), -B( Q6 )( Q7 ), and -P(=O)( Q8 )( Q9 ), organometallic compounds: In the above chemical formulas 9-1 to 9-19 and 10-1 to 10-156, Ph is a phenyl group, TMS is a trimethylsilyl group, and * is a bonding site with an adjacent atom.
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8. In paragraph 1, i) A 4 is *-O-*' or *-S-*', and T 3 is *-C(=O)-*'or; ii) A 4 is represented by one of the following chemical formulas 4(1) to 4(5), and T 3 is a single bond, or iii) Organometallic compounds in which A 4 is *-O-*' or *-S-*' and T 3 is a single bond: Among the above chemical formulas A4(1) to A4(5), The descriptions for R 41 and R 42 are each identical to the description for R 1 in Paragraph 1, and * is the binding site with M in Chemical Formula 1, and *' is the binding site with T3 in Chemical Formula 1.
9. In paragraph 1, An organometallic compound represented by A 3 as one of the following chemical formulas CY3-1 to CY3-10: Among the above chemical formulas CY3-1 to CY3-10, X 3 is N, and The description of R3 is the same as that stated in Paragraph 1, and The descriptions for R 3a to R 3c are each identical to the description for R 3 in Paragraph 1, and Among the above chemical formulas CY3-1 to CY3-10, * is a binding site with M in chemical formula 1, *" is a binding site with T2 in chemical formula 1, and *' is a binding site with T3 in chemical formula 1.
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11. In paragraph 1, i) If A 4 is *-O-*' or *-S-*' and T 3 is *-C(=O)-*', or ii) The above A4 is represented by one of the following chemical formulas A4(1) to A4(3) and A4(5), and the above T3 is a single bond, or, iii) An organometallic compound in which the above A 4 is *-O-*' or *-S-*' and the above T 3 is a single bond: Among the above chemical formulas A4(1) to A4(3) and A4(5), The descriptions for R 41 and R 42 are each identical to the description for R 1 in Paragraph 1, and * is the binding site with M in Chemical Formula 1, and *' is the binding site with T3 in Chemical Formula 1.
12. First electrode; Second electrode; and An organic layer including a light-emitting layer interposed between the first electrode and the second electrode; Includes, The organic light-emitting device, wherein the organic layer comprises one or more organometallic compounds of any one of claims 1, 4, 5, 8, 9 and 11.
13. In Paragraph 12, The first electrode above is an anode, and The above second electrode is a cathode, and The above 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 above includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and The above electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof, in an organic light-emitting device.
14. In Paragraph 12, An organic light-emitting device in which the above organometallic compound is included in the above light-emitting layer.
15. In Paragraph 14, An organic light-emitting device in which the light-emitting layer further comprises a host, and, based on weight, the content of the host is greater than the content of the organometallic compound.

Description

Organometallic compound, organic light emitting device including the same, and a composition for diagnosing including the same Organometallic compounds, organic light-emitting diodes containing the same, and diagnostic compositions containing the same are presented. Organic light-emitting devices are self-luminous devices that have excellent viewing angle, response time, brightness, driving voltage, and response speed, and can be multicolored. According to one example, an organic light-emitting device may include an anode, a cathode, and an organic layer interposed between the anode and the cathode, which includes a light-emitting layer. A hole transport region may be provided between the anode and the light-emitting layer, and an electron transport region may be provided between the light-emitting layer and the cathode. Holes injected from the anode move to the light-emitting layer via the hole transport region, and electrons injected from the cathode move to the light-emitting layer via the electron transport region. The holes and electrons recombine in the light-emitting layer region to generate excitons. Light is generated as these excitons change from an excited state to a ground state. Meanwhile, luminescent compounds, such as phosphorescent compounds, can also be used for monitoring, sensing, and detecting biological substances such as various cells and proteins. FIG. 1 is a cross-sectional view schematically showing an organic light-emitting device according to one embodiment. The above organometallic compound is represented by the following chemical formula 1: <Chemical Formula 1> In the above chemical formula 1, M may be beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au). According to one embodiment, the above M may be Pd or Pt, but is not limited thereto. Among the bonds between A1 and M, between A2 and M, between A3 and M, and between A4 and M in the above Chemical Formula 1, two bonds are covalent bonds, and the remaining two bonds may be coordinate bonds. Thus, the organometallic compound represented by the above Chemical Formula 1 may be electrically neutral. According to one embodiment, the bond between A1 and M and the bond between A4 and M are covalent bonds, and the bond between A2 and M and the bond between A3 and M may be coordinate bonds. In the above Chemical Formula 1, A1 is a ring CY1 represented by one of the following Chemical Formulas A1-1 and A1-2; in the following Chemical Formulas A1-1 and A1-2, * is a binding site with M in Chemical Formula 1, and *' is a binding site with T1 in Chemical Formula 1; in the above Chemical Formula 1, A2 is a ring CY2 represented by one of the following Chemical Formulas A2-1 to A2-3; in the following Chemical Formulas A2-1 to A2-3, * is a binding site with M in Chemical Formula 1, *' is a binding site with T1 in Chemical Formula 1, and *" is a binding site with T2 in Chemical Formula 1; in the above Chemical Formula 1, A3 is a ring CY3 represented by one of the following Chemical Formulas A3-1 to A3-3; in the following Chemical Formulas A3-1 to A3-3, * is a binding site with M in Chemical Formula 1, *" is a binding site with T2 in Chemical Formula 1, and *' is a binding site with T3 in Chemical Formula 1. It is a site, and A4 in the above chemical formula 1 may be a first atom bonded to M or a non-cyclic moiety including a first atom bonded to M: The first atom mentioned above may be, for example, B, P, Si, O, or S, but is not limited thereto. According to one embodiment, the first atom may be O, but is not limited thereto. Among the above chemical formulas A1-1, A1-2, A2-1 to A2-3 and A3-1 to A3-3, X 1 to X 3 and Y 1 to Y 6 may be C or N independently of each other. For example, among the above chemical formulas A1-1, A1-2, A2-1 to A2-3 and A3-1 to A3-3, X1 to X3 may be N, but are not limited thereto. Among the above chemical formulas A1-1, A1-2, A2-1 to A2-3 and A3-1 to A3-3, ring CY 1 to ring CY 3 can be independently selected from C 5 -C 30 carbocyclic groups and C 1 -C 30 heterocyclic groups. For example, the above rings CY 1 to CY 3 are independently a benzene group, a naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, chrysene group, cyclopentadiene group, 1,2,3,4-tetrahydronaphthalene group, furan group, thiophene group, silol group, indene group, fluorene group, indole group, carbazole group, benzofuran group, dibenzofuran group, benzothiophen group, dibenzothiophen group, benzocilol group, dibenzocilol group, azafluorene group, azacarbazole group, azadibenzofuran group, azadibenzothiophen group, azadibenzocilol group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline It may be selected from the group, isoquinoline group, quinoxaline