Organometallic compound, and organic light emitting device and diagnostic composition including the same
阅读说明：本技术 有机金属化合物、以及包括其的有机发光器件和诊断组合物 (Organometallic compound, and organic light emitting device and diagnostic composition including the same ) 是由 李锦喜 郭允铉 荒谷介和 李智娟 曹裕利 崔钟元 崔华逸 黄圭荣 于 2020-04-08 设计创作，主要内容包括：公开有机金属化合物、以及包括其的有机发光器件和诊断组合物。所述有机金属化合物由式1表示,其中,在式1中,M、L<Sub>1</Sub>、L<Sub>2</Sub>、n1、和n2各自与在本文中描述的相同。式1M(L<Sub>1</Sub>)<Sub>n1</Sub>(L<Sub>2</Sub>)<Sub>n2</Sub>。(Disclosed are organometallic compounds, and organic light emitting devices and diagnostic compositions including the same. The organometallic compound is represented by formula 1, wherein, in formula 1, M, L 1 、L 2 N1, and n2 are each the same as described herein. Formula 1M (L) 1 ) n1 (L 2 ) n2 。)
1. An organometallic compound represented by formula 1:
formula 1
M(L1)n1(L2)n2，
Wherein, in the formula 1,
m is a transition metal, and M is a transition metal,
L1is a ligand represented by the formula 2,
n1 is 1,2, or 3, wherein, when n1 is 2 or greater, two or more L s1Are the same as or different from each other,
L2is a monodentate ligand, a bidentate ligand, a tridentate ligand, or a tetradentate ligand,
n2 is 0, 1,2,3, or 4, wherein, when n2 is 2 or greater, two or more L s2Are the same as or different from each other, and
L1and L2Different from each other:
formula 2
Wherein, in the formula 2,
X1is C, N, Si or is P, and is,
X21is C or N, and is a compound of,
ring CY1And ring CY21Each independently is C5-C30Carbocyclic group or C2-C30A heterocyclic group,
X2and X3Each independently O, S, Se, or C (R)2) Wherein X is2Or X3Is O, S or Se, or a salt thereof,
X4is N or C (R)4)，
X5Is N or C (R)5)，
R1、R2、R4、R5And R21Each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5Hydroxyl group, cyano group, nitro group, amino 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, substituted or unsubstituted C1-C60Alkyl, substituted or unsubstituted C2-C60Alkenyl, substituted or unsubstituted C2-C60Alkynyl, substituted or unsubstituted C1-C60Alkoxy, substituted or unsubstituted C3-C10Cycloalkyl, substituted or unsubstituted C2-C10Heterocycloalkyl, substituted or unsubstituted C3-C10Cycloalkenyl, substituted or unsubstituted C2-C10Heterocycloalkenyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Aryloxy, substituted or unsubstituted C6-C60Arylthio, substituted or unsubstituted C1-C60Heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N (Q)1)(Q2)、-Si(Q3)(Q4)(Q5)、-B(Q6)(Q7)、-P(＝O)(Q8)(Q9) or-P (Q)8)(Q9)，
a1 and a21 are each independently integers from 0 to 20,
ring CY1And R2Are not linked to each other, and R1And R2Are not connected with each other and are not connected with each other,
L11is unsubstituted or substituted by at least one R10aSubstituted C5-C30Carbocyclic group, unsubstituted or substituted by at least one R10aSubstituted C2-C30A heterocyclic group,
b11 is an integer of 0-10, wherein, when b11 is 0, is composed of: - (L)11)b11The group represented by is a single bond, and when b11 is 2 or more, two or more of L11Are the same as or different from each other,
a plurality of adjacent R21Are optionally linked to form an unsubstituted or substituted by at least one R10aSubstituted C5-C30Carbocyclic group, unsubstituted or substituted by at least one R10aSubstituted C2-C30A heterocyclic group,
R10aand with respect to R21The same as that defined above is true for the same,
each of which represents a binding site to M in formula 1,
substituted C5-C30Carbocyclic group, substituted C2-C30Heterocyclic radical, substituted C1-C60Alkyl, substituted C2-C60Alkenyl, substituted C2-C60Alkynyl, substituted C1-C60Alkoxy, substituted C3-C10Cycloalkyl, substituted C2-C10Heterocycloalkyl, substituted C3-C10Cycloalkenyl, substituted C2-C10Heterocycloalkenyl, substituted C6-C60Aryl, substituted C6-C60Aryloxy, substituted C6-C60Arylthio, substituted C1-C60Heteroaromatic compoundsThe substituents for the radicals, substituted monovalent non-aromatic fused polycyclic groups, and substituted monovalent non-aromatic fused heteropolycyclic groups are:
deuterium, -F, -Cl, -Br, -I, -CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2Hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, or C1-C60An alkoxy group;
c each substituted as follows1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, or C1-C60Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2Hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C3-C10Cycloalkyl radical, C2-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl radical, C2-C10Heterocycloalkenyl, C6-C60Aryl radical, C6-C60Aryloxy radical, C6-C60Arylthio group, C1-C60Heteroaryl, monovalent non-aromatic fused polycyclic radical, monovalent non-aromatic fused heteropolycyclic radical, -N (Q)11)(Q12)、-Si(Q13)(Q14)(Q15)、-B(Q16)(Q17)、-P(＝O)(Q18)(Q19) Or any combination thereof;
C3-C10cycloalkyl radical, C2-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl radical, C2-C10Heterocycloalkenyl, C6-C60Aryl radical, C6-C60Aryloxy radical, C6-C60Arylthio group, C1-C60Heteroaryl, monovalent non-aromatic fused polycyclic group,Or a monovalent non-aromatic fused heteropolycyclic group;
c each substituted as follows3-C10Cycloalkyl radical, C2-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl radical, C2-C10Heterocycloalkenyl, C6-C60Aryl radical, C6-C60Aryloxy radical, C6-C60Arylthio group, C1-C60A heteroaryl, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2Hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, C1-C60Alkoxy radical, C3-C10Cycloalkyl radical, C2-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl radical, C2-C10Heterocycloalkenyl, C6-C60Aryl radical, C6-C60Aryloxy radical, C6-C60Arylthio group, C1-C60Heteroaryl, monovalent non-aromatic fused polycyclic radical, monovalent non-aromatic fused heteropolycyclic radical, -N (Q)21)(Q22)、-Si(Q23)(Q24)(Q25)、-B(Q26)(Q27)、-P(＝O)(Q28)(Q29) Or any combination thereof;
-N(Q31)(Q32)、-Si(Q33)(Q34)(Q35)、-B(Q36)(Q37) or-P (═ O) (Q)38)(Q39) (ii) a Or
Any combination thereof, and
Q1-Q9、Q11-Q19、Q21-Q29and Q31-Q39Each independently of the others, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazino,hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, C1-C60Alkoxy radical, C3-C10Cycloalkyl radical, C2-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl radical, C2-C10Heterocycloalkenyl radical, C6-C60Aryl radical, quilt C1-C60Alkyl radical, C6-C60Aryl, or any combination thereof substituted C6-C60Aryl radical, C6-C60Aryloxy radical, C6-C60Arylthio group, C1-C60A heteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group.
2. The organometallic compound according to claim 1, wherein
M is Ir or Os, and the sum of n1 and n2 is 3 or 4; or
M is Pt, and the sum of n1 and n2 is 2.
3. The organometallic compound according to claim 1, wherein,
ring CY1And ring CY21Each independently being a cyclopentene group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo [9,10 ] group]Phenanthrene group, pyrene group,A group, a cyclopentadiene group, a1, 2,3, 4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzothiole group, a benzogermanocyclopentadiene group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermanocyclopentadiene group, a dibenzothiophene groupSelenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5, 5-dioxide group, azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, azabenzothiapyrrole group, azabenzogermane heterocyclopentadiene group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azabenzoborole group, azabenzophosphole group, azafluorene group, azabenzothiapyrrole group, azabenzogermane heterocyclopentadiene group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azabenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5, 5-dioxide group, azadibenzothiophene group, azabenzothiophene group, azadibenzothiophene 5-oxide, An aza-9H-fluoren-9-one group, an aza-dibenzothiophene 5, 5-dioxide 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 thiophene,Azole group, iso
4. The organometallic compound according to claim 1, wherein
R1、R2、R4、R5、R21And R10aEach independently is:
hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, -SF5、C1-C20Alkyl, or C1-C20An alkoxy group;
c each substituted as follows1-C20Alkyl or C1-C20Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2Hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C10Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1]Pentyl, bicyclo [2.1.1]Hexyl, bicyclo [2.2.1]Heptyl, bicyclo [2.2.2]Octyl, phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof;
cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, bicyclo [1.1.1 ] respectively unsubstituted or substituted as follows]Pentyl, bicyclo [2.1.1]Hexyl, bicyclo [2.2.1]Heptyl, bicyclo [2.2.2]Octyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthracyl, benzo [9,10 ]]Phenanthryl, pyrenyl,A group selected from the group consisting of a pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl,
-N(Q1)(Q2)、-Si(Q3)(Q4)(Q5)、-B(Q6)(Q7)、-P(＝O)(Q8)(Q9) or-P (Q)8)(Q9) And are and
Q1-Q9and Q33-Q35Each independently is:
-CH3、-CD3、-CD2H、-CDH2、-CH2CH3、-CH2CD3、-CH2CD2H、-CH2CDH2、-CHDCH3、-CHDCD2H、-CHDCDH2、-CHDCD3、-CD2CD3、-CD2CD2H. or-CD2CDH2(ii) a Or
N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each unsubstituted or substituted as follows: deuterium, C1-C10Alkyl, phenyl, or any combination thereof.
5. The organometallic compound according to claim 1, wherein
In formula 2 is represented by
in formula 2, R1And R2Each independently is:
hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, or-SF5(ii) a Or
Each unsubstituted or substituted as follows1-C60Alkyl radical, C1-C60Alkoxy radical, C3-C10Cycloalkyl radical, C2-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl group, or C2-C10Heterocycloalkenyl: deuterium, -F, -Cl, -Br, -I, -CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2Cyano, C1-C20Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof, and
a1 is an integer from 0 to 10.
6. The organometallic compound according to claim 1, wherein
In formula 2 is represented byThe radicals represented are each unsubstituted or substituted by the number a 1R1Substituted phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthracyl, benzo [9,10 ] s]Phenanthryl, pyrenyl,
in formula 2, R1And R2Each independently is:
hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, or-SF5(ii) a Or
Methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, tert-decyl, C, each unsubstituted or substituted as follows1-C10Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, or cycloheptenyl: deuterium, -F, -Cl, -Br, -I, -CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2Cyano, C1-C20Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof, and
a1 is an integer from 0 to 5.
7. The organometallic compound according to claim 1, wherein
ByThe group represented is a group represented by one of formulae 10-13(1) to 10-13(18) and 10-13:
wherein, in the formulae 10-13(1) to 10-13(18) and 10-13, R1a-R1eIndependently of one another with respect to R in claim 11Is as defined wherein R is1a-R1eEach is not hydrogen and denotes a binding site to an adjacent atom.
8. The organometallic compound according to claim 1, wherein
In formula 2 is represented by
wherein, in the formulae CY21-1 to CY21-25,
X21and R21Each independently as described in claim 1,
X22is C (R)22)(R23)、N(R22) O, S, or Si (R)22)(R23)，
R22-R29Independently of one another with respect to R in claim 121The same as that defined above is true for the same,
a26 is an integer of 0 to 6,
a24 is an integer of 0 to 4,
a23 is an integer of 0 to 3,
a22 is an integer of 0 to 2,
"represents a binding site to a carbon atom of an adjacent 6-membered ring in formula 2, and
represents a binding site to M in formula 1.
9. The organometallic compound according to claim 8, wherein
In formula 2 is represented by
wherein, in the formulae CY21(1) to CY21(56),
X21and R21Each independently as described in claim 1,
R21a-R21dindependently of one another with respect to R in claim 121Is as defined wherein R is21And R21a-R21dEach of which is not a hydrogen atom,
"represents a binding site to a carbon atom of an adjacent 6-membered ring in formula 2, and
represents a binding site to M in formula 1.
10. The organometallic compound according to claim 1, wherein
L1Is a ligand represented by formula 2A or 2B:
formula 2A
Formula 2B
Wherein, in the formulae 2A and 2B, X1、X21Ring CY1Ring CY21、X4、X5、R1、R2、R21、a1、a21、L11B11, b and c' are each independently the same as described in claim 1, wherein X is2And X3Each independently O, S, or Se.
11. The organometallic compound according to claim 1, wherein,
in formula 1, L2Is a bidentate ligand attached to M in formula 1 via O, S, N, C, P, Si, or As.
12. The organometallic compound according to claim 1, wherein,
in formula 1, L2Is a bidentate ligand represented by formula 3:
formula 3
Wherein, in the formula 3,
X31and X32Each is O;
X31is O and X32Is N; or
X31Is N and X32The content of the carbon dioxide is C,
each of x and x' represents a binding site to M in formula 1.
13. The organometallic compound according to claim 1, wherein,
in formula 1, L2Are groups represented by formulas 3A-3F:
wherein, in the formulae 3A to 3F,
Y13is O, N, N (Z)1)、P(Z1)(Z2) Or As (Z)1)(Z2)，
Y14Is O, N, N (Z)3)、P(Z3)(Z4) Or As (Z)3)(Z4)，
T11Is a single bond, a double bond, — C (Z)11)(Z12)-*'、*-C(Z11)＝C(Z12)-*'、*＝C(Z11)-*'、*-C(Z11)＝*'、*＝C(Z11)-C(Z12)＝C(Z13)-*'、*-C(Z11)＝C(Z12)-C(Z13)＝*'、*-N(Z11) -, or unsubstituted or substituted by at least one Z11Substituted C5-C30A carbocyclic group which is a radical of a carbocyclic ring,
a11 is an integer of 1-10,
Y11and Y12Each independently being C or N,
T21is a single bond, a double bond, O, S, C (Z)11)(Z12)、Si(Z11)(Z12) Or N (Z)11)，
Ring CY11And ring CY12Each independently is C5-C30Carbocyclic group or C2-C30A heterocyclic group,
A1is a P or an As, and is,
Z1-Z4and Z11-Z13Independently of one another with respect to R in claim 121The same as that defined above is true for the same,
d1 and d2 are each independently an integer from 0 to 10, and
each of x and x' represents a binding site to M in formula 1.
14. The organometallic compound according to claim 1, wherein,
in formula 1, L2Is a group represented by one of formulae 3-1(1) to 3-1(66) and 3-1(301) to 3-1 (309):
wherein, in the formulae 3-1(1) to 3-1(66) and 3-1(301) to 3-1(309),
X41is O, S, N (Z)21)、C(Z21)(Z22) Or Si (Z)21)(Z22)，
Z1-Z4、Z1a、Z1b、Z1c、Z1d、Z2a、Z2b、Z2c、Z2d、Z11-Z14、Z21And Z22Independently of one another with respect to R in claim 121The same as that defined above is true for the same,
d14 is an integer from 0 to 4,
d26 is an integer from 0 to 6, and
each of x and x' represents a binding site to M in formula 1.
15. The organometallic compound according to claim 1, wherein
The organometallic compound is one of compounds 1 to 469:
16. an organic light emitting device comprising:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode and including an emission layer,
wherein the organic layer comprises at least one organometallic compound according to any of claims 1-15.
17. An organic light emissive device according to claim 16, wherein
The first electrode is an anode and the second electrode is a cathode,
the second electrode is a cathode and is a cathode,
the organic layer further includes a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,
the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and
the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
18. An organic light emissive device according to claim 16, wherein
The emission layer includes the organometallic compound.
19. An organic light emissive device according to claim 18, wherein
The emission layer further includes a host, and an amount of the host is greater than an amount of the organometallic compound.
20. A diagnostic composition comprising at least one organometallic compound according to any of claims 1-15.
Technical Field
One or more embodiments relate to an organometallic compound, an organic light emitting device including the organometallic compound, and a diagnostic composition including the organometallic compound.
Background
The organic light emitting device is a self-emission device that has excellent characteristics in view angle, response time, luminance, driving voltage, and response speed and produces a full color image.
In an example, an organic light emitting device includes an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes an emissive layer. The hole transport region may be between the anode and the emissive layer, and the electron transport region may be between the emissive layer and the cathode. Holes supplied from the anode may move toward the emission layer through the hole transport region, and electrons supplied from the cathode may move toward the emission layer through the electron transport region. The holes and electrons recombine in the emission layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light.
Luminescent compounds can be used to monitor, sense, or detect a variety of biological materials, including cells and proteins. Examples of the light-emitting compound are phosphorescent light-emitting compounds.
Disclosure of Invention
Aspects of the present disclosure provide novel organometallic compounds, organic light emitting devices including the novel organometallic compounds, and diagnostic compositions including the novel organometallic compounds.
Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the embodiments provided.
One aspect of the present disclosure provides an organometallic compound represented by the following formula 1:
formula 1
M(L1)n1(L2)n2。
In the formula 1, the first and second groups,
m may be a transition metal, and M may be a transition metal,
L1may be a ligand represented by formula 2,
n1 can be 1,2, or 3, wherein, when n1 is 2 or greater, two or more L s1May be the same as or different from each other,
L2can be monodentate, bidentate, tridentate, or tetradentate,
n2 can be 0, 1,2,3, or 4, wherein, when n2 is 2 or greater, two or more L s2May be the same as or different from each other, and
L1and L2Can be different from each other:
formula 2
In the formula 2, the first and second groups,
X1may be C, N, Si, or P,
X21can be C or N, and can be C or N,
ring CY1And ring CY21May each independently be C5-C30Carbocyclic group or C2-C30A heterocyclic group,
X2and X3Each independently may be O, S, Se, or C (R)2) Wherein X is2Or X3May be O, S, or Se,
X4can be N or C (R)4)，
X5Can be N or C (R)5)，
R1、R2、R4、R5And R21Can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5Hydroxyl group, cyano group, nitro group, amino 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, substituted or unsubstituted C1-C60Alkyl, substituted or unsubstituted C2-C60Alkenyl, substituted or unsubstituted C2-C60Alkynyl, substituted or unsubstituted C1-C60Alkoxy, substituted or unsubstituted C3-C10Cycloalkyl, substituted or unsubstituted C2-C10Heterocycloalkyl, substituted or unsubstituted C3-C10Cycloalkenyl, substituted or unsubstituted C2-C10Heterocycloalkenyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Aryloxy, substituted or unsubstituted C6-C60Arylthio, substituted or unsubstituted C1-C60Heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N (Q)1)(Q2)、-Si(Q3)(Q4)(Q5)、-B(Q6)(Q7)、-P(＝O)(Q8)(Q9) or-P (Q)8)(Q9)，
a1 and a21 can each independently be an integer from 0 to 20,
ring CY1And R2May not be connected to each other, and R1And R2May not be connected to each other and may,
L11may be unsubstituted or substituted by at least one R10aSubstituted C5-C30Carbocyclic group, unsubstituted or substituted by at least one R10aSubstituted C2-C30A heterocyclic group,
b11 can be an integer of 0-10, wherein, when b11 is 0, is composed of — (L)11)b11The group represented by may be a single bond, and when b11 is 2 or more, two or more L11May be the same as or different from each other,
a plurality of adjacent R21Optionally linked to form an unsubstituted or substituted by at least one R10aSubstituted C5-C30Carbocyclic group, unsubstituted or substituted by at least one R10aSubstituted C2-C30A heterocyclic group.
R10aCan be related to R21The same as that defined above is true for the same,
each of which represents a binding site to M in formula 1,
substituted C5-C30Carbocyclic group, substituted C2-C30Heterocyclic radical, substituted C1-C60Alkyl, substituted C2-C60Alkenyl, substituted C2-C60Alkynyl, substituted C1-C60Alkoxy, substituted C3-C10Cycloalkyl, substituted C2-C10Heterocycloalkyl, substituted C3-C10Cycloalkenyl, substituted C2-C10Heterocycloalkenyl, substituted C6-C60Aryl, substituted C6-C60Aryloxy, substituted C6-C60Arylthio, substituted C1-C60The substituent(s) of the heteroaryl, substituted monovalent non-aromatic fused polycyclic group, and substituted monovalent non-aromatic fused heteropolycyclic group can be:
deuterium, -F, -Cl, -Br, -I, -CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2Hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, or C1-C60An alkoxy group;
c each substituted as follows1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, or C1-C60Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2Hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C3-C10Cycloalkyl radical, C2-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl radical, C2-C10Heterocycloalkenyl, C6-C60Aryl radical, C6-C60Aryloxy radical, C6-C60Arylthio group, C1-C60Heteroaryl, monovalent non-aromatic fused polycyclic radical, monovalent non-aromatic fused heteropolycyclic radical, -N (Q)11)(Q12)、-Si(Q13)(Q14)(Q15)、-B(Q16)(Q17)、-P(＝O)(Q18)(Q19) Or any combination thereof;
C3-C10cycloalkyl radical, C2-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl radical, C2-C10Heterocycloalkenyl, C6-C60Aryl radical, C6-C60Aryloxy radical, C6-C60Arylthio group, C1-C60A heteroaryl, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group;
c each substituted as follows3-C10Cycloalkyl radical, C2-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl radical, C2-C10Heterocycloalkenyl, C6-C60Aryl radical, C6-C60Aryloxy radical, C6-C60Arylthio group, C1-C60A heteroaryl, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2Hydroxy, cyano, nitro, amino, amidino, hydrazineA radical, a hydrazone group, a carboxylic acid group or salt thereof, a sulfonic acid group or salt thereof, a phosphoric acid group or salt thereof, C1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, C1-C60Alkoxy radical, C3-C10Cycloalkyl radical, C2-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl radical, C2-C10Heterocycloalkenyl, C6-C60Aryl radical, C6-C60Aryloxy radical, C6-C60Arylthio group, C1-C60Heteroaryl, monovalent non-aromatic fused polycyclic radical, monovalent non-aromatic fused heteropolycyclic radical, -N (Q)21)(Q22)、-Si(Q23)(Q24)(Q25)、-B(Q26)(Q27)、-P(＝O)(Q28)(Q29) Or any combination thereof;
-N(Q31)(Q32)、-Si(Q33)(Q34)(Q35)、-B(Q36)(Q37) or-P (═ O) (Q)38)(Q39) (ii) a Or
Any combination thereof, and
Q1-Q9、Q11-Q19、Q21-Q29and Q31-Q39May each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, C1-C60Alkoxy radical, C3-C10Cycloalkyl radical, C2-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl radical, C2-C10Heterocycloalkenyl radical, C6-C60Aryl radical, quilt C1-C60Alkyl radical, C6-C60Aryl, or any combination thereof substituted C6-C60Aryl radical, C6-C60Aryloxy radical, C6-C60Arylthio group, C1-C60A heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or any combination thereof.
Another aspect of the present disclosure provides an organic light emitting device including: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer may include at least one of the organometallic compounds.
The organometallic compound may be included in the emission layer of the organic layer and may act as a dopant.
Another aspect of the present disclosure provides a diagnostic composition comprising at least one organometallic compound represented by formula 1.
Drawings
These and/or other aspects will become apparent and more readily appreciated from the following description of embodiments, taken in conjunction with fig. 1, which is a schematic cross-sectional view of an organic light emitting device according to embodiments.
Detailed Description
Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to the like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as limited to the descriptions set forth herein. Accordingly, the embodiments are described below merely by referring to the drawings to illustrate aspects of the present description. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items. Expressions such as "at least one of" when preceding or following a list of elements modify the entire list of elements and do not modify individual elements of the list.
It will be understood that when an element is referred to as being "on" another element, it can be directly on the other element or intervening elements may be present. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements present.
It will be understood that, although the terms "first," "second," "third," etc. may be used herein to describe various elements, components, regions, layers and/or sections, these elements, components, regions, layers and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or section from another element, component, region, layer or section. Thus, a first element, component, region, layer or section discussed below could be termed a second element, component, region, layer or section without departing from the teachings herein.
The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, including "at least one", unless the content clearly indicates otherwise. "at least one" is not to be construed as limiting "one" or "an". "or" means "and/or". As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items. It will be further understood that the terms "comprises" and/or "comprising," when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.
Further, relative terms, such as "lower" or "bottom" and "upper" or "top," may be used herein to describe one element's relationship to another element as illustrated in the figures. It will be understood that relative terms are intended to encompass different orientations of the device in addition to the orientation depicted in the figures. For example, if the device in one of the figures is turned over, elements described as being on the "lower" side of other elements would then be oriented on the "upper" side of the other elements. Thus, the exemplary term "lower" can encompass both an orientation of "lower" and "upper," depending on the particular orientation of the figure. Similarly, if the device in one of the figures is turned over, elements described as "below" or "beneath" other elements would then be oriented "above" the other elements. Thus, the exemplary terms "below … …" or "below … …" can encompass both an orientation above … … and below … ….
As used herein, "about" or "approximately" includes the stated value and is meant to be within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art in view of the measurement in question and the error associated with measurement of the particular quantity (i.e., limitations of the measurement system). For example, "about" may mean a deviation from the stated value within one or more standard deviation ranges, or within ± 10%, or 5%.
Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of this disclosure and the relevant art and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.
Exemplary embodiments are described herein with reference to cross-sectional views that are schematic illustrations of idealized embodiments. As such, deviations from the shapes of the figures as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, the embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, regions illustrated or described as flat may typically have rough and/or non-linear features. Further, the sharp corners illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.
One aspect of the present disclosure provides an organometallic compound represented by the following formula 1:
formula 1
M(L1)n1(L2)n2。
M in formula 1 may be a transition metal.
For example, M may be a first row transition metal, a second row transition metal, or a third row transition metal of the periodic table of elements.
In one embodiment, M may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).
In one embodiment, M may be Ir, Pt, Os, or Rh, although embodiments of the disclosure are not limited thereto.
L in formula 11May be a ligand represented by formula 2, and n1 in formula 1 represents L in formula 11And can be 1,2, or 3. When n1 is 2 or more, two or more L1May be the same or different from each other:
formula 2
Formula 2 may be the same as described below.
For example, n1 may be 1 or 2.
L in formula 12May be a monodentate ligand, a bidentate ligand, a tridentate ligand, or a tetradentate ligand, and n2 in formula 1 represents L2And can be 0, 1,2,3, or 4. When n2 is 2 or more, two or more L2May be the same as or different from each other. L is2May be the same as described below.
For example, n2 in formula 1 can be 1 or 2.
In formula 1, L1And L2May be different from each other.
In one embodiment, M may be Ir or Os, and the sum of n1 and n2 may be 3 or 4; alternatively, M may be Pt and the sum of n1 and n2 may be 2.
In formula 2, X1Can be C, N, Si, or P, and X21And may be C or N.
For example, in formula 2, X21May be C.
In formula 2, ring CY1And ring CY21May each independently be C5-C30Carbocyclic group or C2-C30A heterocyclic group.
For example, ring CY1And ring CY21May each independently be i) a first ring, ii) a second ring, iii) a fused ring in which at least two first rings are fused to each other, iv) a fused ring in which at least two second rings are fused to each other, or v) a fused ring in which at least one first ring and at least one second ring are fused to each other.
The first ring can be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzothiophene group, a thiophene group,Azole group, isoAn azole group,
The second ring may be an adamantyl group, a norbornyl group, a norbornene group, a cyclohexane group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
In one embodiment, ring CY1And ring CY21Can each independently be a cyclopentene group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo [9,10 ] group]Phenanthrene group, pyrene group,
In one or more embodiments, ring CY1May be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, an adamantane group, a norborane group, a norbornene group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a phenyl group, a naphthalene group, a fluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a benzo [9,10 ] group]Phenanthrene group, pyrene group,
In formula 2, X2And X3Each independently may be O, S, Se, or C (R)2) Wherein X is2Or X3May be O, S, or Se.
For example, in formula 2, i) X2Can be O, S, or Se, and X3Can be C (R)2) (ii) a Or ii) X2Can be C (R)2) And X3May be O, S, or Se.
In formula 2, X4Can be N or C (R)4) And X5Can be N or C (R)5)。
For example, X4Can be C (R)4) And X5Can be C (R)5)。
In formula 2, R1、R2、R4、R5And R21Can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5Hydroxyl group, cyano group, nitro group, amino 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, substituted or unsubstituted C1-C60Alkyl, substituted or unsubstituted C2-C60Alkenyl, substituted or unsubstituted C2-C60Alkynyl, substituted or unsubstituted C1-C60Alkoxy, substituted or unsubstituted C3-C10Cycloalkyl, substituted or unsubstituted C2-C10Heterocycloalkyl, substituted or unsubstituted C3-C10Cycloalkenyl, substituted or unsubstituted C2-C10Heterocycloalkenyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Aryloxy, substituted or unsubstituted C6-C60Arylthio, substituted or unsubstituted C1-C60Heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N (Q)1)(Q2)、-Si(Q3)(Q4)(Q5)、-B(Q6)(Q7)、-P(＝O)(Q8)(Q9) or-P (Q)8)(Q9) Wherein Q is1-Q9Each as described above.
For example, R1、R2、R4、R5、R21And R10aMay each independently be:
hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, -SF5、C1-C20Alkyl, or C1-C20An alkoxy group;
c each substituted as follows1-C20Alkyl or C1-C20Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2Hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C10Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1]Pentyl, bicyclo [2.1.1]Hexyl, bicyclo [2.2.1]Heptyl, bicyclo [2.2.2]Octyl, phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, or combinations thereofAny combination;
cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, bicyclo [1.1.1 ] respectively unsubstituted or substituted as follows]Pentyl, bicyclo [2.1.1]Hexyl, bicyclo [2.2.1]Heptyl, bicyclo [2.2.2]Octyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthracyl, benzo [9,10 ]]Phenanthryl, pyrenyl,
-N(Q1)(Q2)、-Si(Q3)(Q4)(Q5)、-B(Q6)(Q7)、-P(＝O)(Q8)(Q9) or-P (Q)8)(Q9) And are and
Q1-Q9and Q33-Q35May each independently be:
-CH3、-CD3、-CD2H、-CDH2、-CH2CH3、-CH2CD3、-CH2CD2H、-CH2CDH2、-CHDCH3、-CHDCD2H、-CHDCDH2、-CHDCD3、-CD2CD3、-CD2CD2H. or-CD2CDH2(ii) a Or
N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each unsubstituted or substituted as follows: deuterium, C1-C10An alkyl group, a phenyl group, or any combination thereof, although embodiments of the present disclosure are not limited thereto.
In formula 2, a1 and a21 each independently represent R1Number of (2) and R21And each can independently be an integer from 0-20 (e.g., an integer from 0-10 or an integer from 0-5). When a1 is 2 or greater, two or more R1May be the same as or different from each other, and when a21 is 2 or more, two or more R21May be the same as or different from each other.
In formula 2, ring CY1And R2Are not linked to each other, and R1And R2Are not connected to each other.
In one embodiment, the group of formula 2
In formula 2, R1And R2May each independently be:
hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, or-SF5(ii) a Or
Each unsubstituted or substituted as follows1-C60Alkyl radical, C1-C60Alkoxy radical, C3-C10Cycloalkyl radical, C2-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl group, or C2-C10Heterocycloalkenyl: deuterium, -F, -Cl, -Br, -I, -CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2Cyano, C1-C20Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof, and
a1 can be an integer from 0-10.
a1、R1、C1-C60Alkyl radical, C1-C60Alkoxy radical, C3-C10Cycloalkyl radical, C2-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl radical, C2-C10Heterocycloalkenyl, C6-C30Aryl radical, C2-C30The detailed descriptions of the heteroaryl group, the monovalent non-aromatic fused polycyclic group, and the monovalent non-aromatic fused heteropolycyclic group are the same as those described above.
In one or more embodiments, the compound of formula 2The radicals indicated may be each unsubstituted or substituted by the number a1 of R1Substituted phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthracyl, benzo [9,10 ] s]Phenanthryl, pyrenyl,A base,Pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl,Azolyl radical, isoOxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzofuranyl, benzothienyl
In formula 2, R1And R2May each independently be:
hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, or-SF5(ii) a Or
Methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl (n-nonyl), isononyl (isononyl), sec-nonyl (sec-nonyl), tert-nonyl (tert-nonyl), n-decyl, isodecyl, sec-decyl, tert-decyl, C1-C10Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantineAlkyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl or cycloheptenyl: deuterium, -F, -Cl, -Br, -I, -CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2Cyano, C1-C20Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof, and
a1 may be an integer from 0 to 5, but embodiments of the present disclosure are not limited thereto.
In one or more embodiments, the compound of formula 2
in the formulae 10-13(1) to 10-13(18) and 10-13, R1a-R1eEach independently of the other with respect to R1Is as defined wherein R is1a-R1eEach is not hydrogen and denotes a binding site to an adjacent atom (e.g. a carbon atom).
For example, in formula 2
in formulae 9-1 to 9-19 and 10-1 to 10-240, a represents a binding site to an adjacent atom, Ph represents a phenyl group, and TMS represents a trimethylsilyl group.
In formula 2, L11May be unsubstituted or substituted by at least one R10aSubstituted C5-C30Carbocyclic group, unsubstituted or substituted by at least one R10aSubstituted C2-C30Heterocyclic group, wherein R10aAs described above.
For example, L11May each be unsubstituted or substituted by at least one R10aSubstituted phenyl groups, naphthyl groups, anthracenyl groups, phenanthrenyl groups, benzo [9,10 ]]Phenanthrene group, pyrene group,
In formula 2, b11 represents L11And may be an integer of 0 to 10, wherein, when b11 is 0, is represented by — (L)11)b11The group represented by may be a single bond, and when b11 is 2 or more, two or more L11May be the same as or different from each other. For example, b11 may be 0, 1,2, or 3, although embodiments of the present disclosure are not limited thereto.
In formula 2, a plurality of adjacent R21Optionally linked to form an unsubstituted or substituted by at least one R10aSubstituted C5-C30Carbocyclic group, unsubstituted or substituted by at least one R10aSubstituted C2-C30Heterocyclic groups (e.g. each unsubstituted or substituted with at least one R)10aA substituted phenyl group, a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, or a benzothiole group, wherein R is10aAnd with respect to R21The same as defined). C5-C30Carbocyclic group and C2-C30The detailed description of heterocyclic groups is the same as described above.
In formula 2, each of x and x' represents a binding site to M in formula 1.
In one embodiment, the group of formula 2
in the formulae CY21-1 to CY21-25,
X21and R21Each independently may be the same as described herein,
X22can be C (R)22)(R23)、N(R22) O, S, or Si (R)22)(R23)，
R22-R29May each independently relate to R21The same as that defined above is true for the same,
a26 can be an integer from 0-6,
a24 can be an integer from 0-4,
a23 can be an integer from 0-3,
a22 can be an integer from 0-2,
"represents a binding site to a carbon atom of an adjacent 6-membered ring in formula 2, and
represents a binding site to M in formula 1.
In one embodiment, the group of formula 2
in the formulae CY21(1) to CY21(56),
X21and R21Each independently may be the same as described herein,
R21a-R21dmay each independently relate to R21Are as defined, and R21And R21a-R21dEach of which is not a hydrogen atom,
"represents a binding site to a carbon atom of an adjacent 6-membered ring in formula 2, and
represents a binding site to M in formula 1.
In an implementation methodWherein, in formula 2The group represented may be a group represented by formula CY21(1), CY21(3), or CY21(10) or a group represented by one of formulae CY21-20 to CY21-25, but the embodiments of the present disclosure are not limited thereto. For example, in formula CY21(10), R21aAnd R21bMay be the same as or different from each other. In one embodiment, in formula CY21(10), R21aAnd R21bCan be different from each other, and R21aThe number of carbon atoms included may be greater than R21bThe number of carbon atoms included.
In one embodiment, in formula 1, L1May be a ligand represented by formula 2A or 2B, but the embodiments of the present disclosure are not limited thereto:
formula 2A
Formula 2B
In formulae 2A and 2B, X1、X21Ring CY1Ring CY21、X4、X5、R1、R2、R21、a1、a21、L11B11, b and c' may each independently be the same as described herein, wherein X is2And X3Each independently may be O, S, or Se.
In formula 1, L2May be a bidentate ligand attached to M of formula 1 via O, S, N, C, P, Si, or As.
In one embodiment, in formula 1, L2May be a bidentate ligand represented by formula 3:
formula 3
In the formula 3, the first and second groups,
X31and X32May each independently be O, S, N, C, P, Si or As,
each of x and x' represents a binding site to M in formula 1.
For example, in formula 3, i) X31And X32May each be O; ii) X31Can be O, and X32Can be N, or iii) X31Can be N, and X32May be C, but embodiments of the present disclosure are not limited thereto.
In one or more embodiments, in formula 1, L2May be a monodentate ligand, e.g. I-、Br-、Cl-Sulfide (sulfide), nitrate, azide (azide), hydroxide, cyanate, isocyanate, thiocyanate, water, acetonitrile, pyridine, ammonia, carbon monoxide, P (Ph)3、P(Ph)2CH3、PPh(CH3)2Or P (CH)3)3However, the embodiments of the present disclosure are not limited thereto.
In one or more embodiments, in formula 1, L2May be a bidentate ligand, for example, oxalate, acetylacetonate, picolinic acid, 1, 2-bis (diphenylphosphino) ethane, 1-bis (diphenylphosphino) methane, glycinate, or ethylenediamine, but the embodiments of the present disclosure are not limited thereto.
In one or more embodiments, in formula 1, L2May be a group represented by one of formulas 3A-3F:
in the formulae 3A-3F,
Y13can be O, N, N (Z)1)、P(Z1)(Z2) Or As (Z)1)(Z2)，
Y14Can be O, N, N (Z)3)、P(Z3)(Z4) Or As (Z)3)(Z4)，
T11Can be single bond, double bond, or-C (Z)11)(Z12)-*'、*-C(Z11)＝C(Z12)-*'、*＝C(Z11)-*'、*-C(Z11)＝*'、*＝C(Z11)-C(Z12)＝C(Z13)-*'、*-C(Z11)＝C(Z12)-C(Z13)＝*'、*-N(Z11) -, or unsubstituted or substituted by at least one Z11Substituted C5-C30A carbocyclic group which is a radical of a carbocyclic ring,
a11 can be an integer from 1-10,
Y11and Y12May each independently be C or N,
T21can be single bond, double bond, O, S, C (Z)11)(Z12)、Si(Z11)(Z12) Or N (Z)11)，
Ring CY11And ring CY12May each independently be C5-C30Carbocyclic group or C2-C30A heterocyclic group,
A1can be a P or an As,
Z1-Z4and Z11-Z13May each independently relate to R21The same as that defined above is true for the same,
d1 and d2 may each independently be an integer from 0 to 10, and
each of x and x' represents a binding site to M in formula 1.
In formulas 3A-3F, C5-C30Carbocyclic group and said C2-C30The heterocyclic groups may each independently be substituted with respect to ring CY21The same is defined.
For example, in formula 3D
In formulas 3C and 3DThe moiety represented may be a group represented by one of formulae CY12-1 to CY 12-34:
in the formulae CY11-1 to CY11-34 and CY12-1 to CY12-34,
X31can be O, S, N (Z)11)、C(Z11)(Z12) Or Si (Z)11)(Z12)，
X41Can be O, S, N (Z)21)、C(Z21)(Z22) Or Si (Z)21)(Z22)，
Y11、Y12、Z1And Z2Each independently may be the same as described herein,
Z11-Z18and Z21-Z28May each independently relate to R21The same as that defined above is true for the same,
d12 and d22 can each independently be an integer from 0 to 2,
d13 and d23 can each independently be an integer from 0 to 3,
d14 and d24 can each independently be an integer from 0 to 4,
d15 and d25 can each independently be an integer from 0 to 5,
d16 and d26 may each independently be an integer from 0 to 6, and
in formulae CY11-1 to CY11-34 and CY12-1 to CY12-34, each of a and a' represents a binding site to M in formula 1, and"represents a group adjacent to an atom in formula 3C or T in formula 3D21The binding site of (3).
In one embodiment, in formula 1, L2May be a group represented by one of formulas 3-1(1) to 3-1(66) and 3-1(301) to 3-1(309), but embodiments of the present disclosure are not limited thereto:
in formulas 3-1(1) to 3-1(66) and 3-1(301) to 3-1(309),
X41can be O, S, N (Z)21)、C(Z21)(Z22) Or Si (Z)21)(Z22)，
Z1-Z4、Z1a、Z1b、Z1c、Z1d、Z2a、Z2b、Z2c、Z2d、Z11-Z14、Z21And Z22May each independently relate to R21The same as that defined above is true for the same,
d14 can be an integer from 0-4,
d26 can be an integer from 0 to 6, and
each of x and x' represents a binding site to M in formula 1.
For example, Z in the formula 3-1(301)11And Z13Each may independently be methyl.
In one embodiment, Z in formula 3-1(301)11、Z13Or combinations thereof can each independently be substituted or unsubstituted C2-C30Alkyl or substituted or unsubstituted C3-C10Cycloalkyl groups, but embodiments of the present disclosure are not limited thereto.
In one embodiment, the organometallic compound represented by formula 1 may emit red or green light.
As used herein, the terms "azaindole group, azabenzoboracene group, azabenzophosphole group, azaindene group, azabenzothiazole group, azabenzogermanocyclopentadiene group, azabenzobenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azabenzoboracene group, azabenzophosphole group, azadibenzophosphole group, azafluorene group, azabenzothiazole group, azabenzogermanocyclopentadiene group, azabenzodibenzothiophene group, azabenzoselenophene group, azabenzofuran group, azabenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, and azabenzothiophene 5, 5-dioxide group" each refer to a compound having a structure similar to "indole group," indole group ", and" indole group, A benzoborole group, a benzophosphole group, an indene group, a benzothiole group, a benzogermanocyclopentadiene group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermanocyclopentadiene group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, and a dibenzothiophene 5, 5-dioxide group "wherein at least one carbon atom constituting the cyclic group is replaced by N.
In one or more embodiments, the organometallic compound represented by formula 1 may be one of compounds 1 to 469, but embodiments of the present disclosure are not limited thereto:
l of an organometallic compound represented by the formula 11May be a ligand represented by formula 2A, and represents L1The number n1 of (a) may be 1,2, or 3. That is, the organometallic compound includes a ligand represented by formula 2 as a ligand attached to the metal M.
X in formula 22And X3Each independently may be O, S, Se, or C (R)2) Wherein X is2Or X3May be O, S, or Se. That is, in formula 2, the 5-membered ring (see formula 2') does not include ═ N ″ (' and ″ ' each represent a binding site to an adjacent atom) as a ring-forming atom, and includes O, S, or Se. In addition, in formula 2, the 5-membered ring and the 6-membered ring are fused to each other while sharing carbon 1 and carbon 2 (see formula 2'). Thus, the organometallic compound represented by formula 1 can be preventedDecrease of intermolecular binding force of (3). Accordingly, a decrease in the lifetime of an electronic device, such as an organic light emitting device, including the organometallic compound represented by formula 1 can be prevented.
2 'of'
The ligand represented by formula 2 includes "Ring CY1". Accordingly, transition dipole moment is increased in the orientation axis direction of formula 1, and the orientation (alignment) of the organometallic compound represented by formula 1 can be improved, thereby improving the light emitting efficiency of an electronic device, such as an organic light emitting device, including the organometallic compound represented by formula 1.
Meanwhile, in formula 2, ring CY1And R2Are not linked to each other, and R1And R2Are not connected to each other. Accordingly, the transition dipole moment of formula 1 can be prevented from deviating to a direction different from the alignment axis direction of formula 1, thereby improving the light emitting efficiency of an electronic device, such as an organic light emitting device, including the organometallic compound represented by formula 1.
The Highest Occupied Molecular Orbital (HOMO) level, Lowest Unoccupied Molecular Orbital (LUMO) level, and triplet state (T) of some of the organometallic compounds represented by formula 1 were evaluated by Density Functional Theory (DFT) accompanied by gaussian program of molecular structure optimization based on B3LYP1) Energy levels, and the results are shown in table 1.
TABLE 1
Referring to table 1, it was confirmed that the organometallic compound represented by formula 1 has such electrical characteristics as being suitable for use as a dopant in electronic devices such as organic light emitting devices.
The method for synthesizing the organometallic compound represented by formula 1 can be understood by those of ordinary skill in the art by referring to the synthetic examples provided below.
Accordingly, the organometallic compound represented by formula 1 may be suitably used in an organic layer of an organic light emitting device, for example, as a dopant in an emission layer of the organic layer. Another aspect of the present disclosure provides an organic light emitting device including: a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes at least one organometallic compound represented by formula 1.
The organic light emitting device may have a low driving voltage, a high external quantum light emitting efficiency, a low roll-off ratio, and a long lifetime due to the inclusion of the organic layer including the organometallic compound represented by formula 1.
The organometallic compound represented by formula 1 may be used between the pair of electrodes of the organic light emitting device. For example, the organometallic compound represented by formula 1 may be included in the emission layer. In this regard, the organometallic compound may serve as a dopant, and the emission layer may further include a host (i.e., the amount of the organometallic compound represented by formula 1 is less than the amount of the host). The emitting layer may emit green or red light, for example.
As used herein, the expression "(organic layer) including at least one organometallic compound" may include a case where "(organic layer) includes the same organometallic compound represented by formula 1" and a case where "(organic layer) includes two or more different organometallic compounds represented by formula 1".
For example, the organic layer may include only compound 1 as the organometallic compound. In this regard, compound 1 may be present only in the emission layer of the organic light emitting device. In one or more embodiments, the organic layer can include compound 1 and compound 2 as the organometallic compound. In this regard, compound 1 and compound 2 can be present in the same layer (e.g., both compound 1 and compound 2 can be present in the emissive layer).
The first electrode may be an anode as a hole injection electrode, and the second electrode may be a cathode as an electron injection electrode; or the first electrode may be a cathode as an electron injecting electrode, and the second electrode may be an anode as a hole injecting electrode.
For example, in the organic light emitting device, the first electrode is an anode, and the second electrode is a cathode, and the organic layer further includes a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, and the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
The term "organic layer" as used herein refers to a single layer and/or a plurality of layers disposed between a first electrode and a second electrode of an organic light emitting device. The "organic layer" may include an organometallic complex containing a metal in addition to an organic compound.
Fig. 1 is a schematic view of an organic
A substrate may additionally be provided below the
The
The
The
The
The hole transport region may be disposed between the
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 a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, which are sequentially stacked in the stated order from the
When the hole transport region includes a Hole Injection Layer (HIL), the hole injection layer may be formed on the
When the hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on the material used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100 ℃ to about 500 ℃, about 10 ℃-8Torr to about 10-3Vacuum pressure of torr, and
When the hole injection layer is formed using spin coating, coating conditions may vary depending on the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, the coating speed may be about 2,000rpm to about 5,000rpm, and the temperature at which the heat treatment for removing the solvent after coating is performed may be about 80 ℃ to about 200 ℃. However, the coating conditions are not limited thereto.
The conditions for forming the hole transport layer and the electron blocking layer can be understood by referring to the conditions for forming the hole injection layer.
The hole transport region may include, for example, m-MTDATA, TDATA, 2-TNATA, NPB, β -NPB, TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4',4 ″ -tris (N-carbazolyl) triphenylamine (TCTA), polyaniline/dodecylbenzene sulfonic acid (PANI/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-sulfostyrene) (PEDOT/PSS), polyaniline/camphorsulfonic acid (PANI/CSA), polyaniline/poly (4-sulfostyrene) (PANI/PSS), a compound represented by the following formula 201, a compound represented by the following formula 202, or any combination thereof:
formula 201
Formula 202
In formula 201, Ar101And Ar102May each independently be each unsubstituted or substituted asSubstituted phenylene, pentalene, indenylene, naphthyleneMesityl, heptenylene, acenaphthylene, fluorenylene, phenalenylene, phenanthrylene, anthrylene, fluoranthrylene, benzo [9,10 ] ene]Phenanthrylene, pyrenyleneRadical, naphthacene radical, phenylene
In formula 201, xa and xb may each independently be an integer of 0 to 5, or may be 0, 1, or 2. For example, xa may be 1 and xb may be 0, although embodiments of the disclosure are not so limited.
In formulae 201 and 202, R101-R108、R111-R119And R121-R124May each independently be:
hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C10Alkyl (e.g. methyl)Alkyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), or C1-C10Alkoxy (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.);
c each substituted as follows1-C10Alkyl or C1-C10Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, or any combination thereof; or
Phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl, each unsubstituted or substituted as follows: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C10Alkyl radical, C1-C10An alkoxy group, or any combination thereof,
embodiments of the present disclosure are not limited thereto.
In formula 201, R109Phenyl, naphthyl, anthracenyl, or pyridinyl, each of which may be unsubstituted or substituted as follows: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C20Alkyl radical, C1-C20Alkoxy, phenyl, naphthyl, anthracenyl, pyridinyl, or any combination thereof.
In one embodiment, the compound represented by formula 201 may be represented by the following formula 201A, but embodiments of the present disclosure are not limited thereto:
formula 201A
R in formula 201A101、R111、R112And R109The detailed description is the same as described above.
For example, the compound represented by formula 201 and the compound represented by formula 202 may each include compounds HT1 through HT20, but are not limited thereto:
the hole transport region can have a thickness of about
In addition to these materials, the hole transport region may further include a charge generation material for improving conductive properties. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region.
The charge generating material may be, for example, a p-dopant. The p-dopant may be a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof, but embodiments of the present disclosure are not limited thereto. Non-limiting examples of the p-dopant are quinone derivatives such as Tetracyanoquinodimethane (TCNQ) or 2,3,5, 6-tetrafluoro-tetracyano-1, 4-benzoquinodimethane (F4-TCNQ); metal oxides such as tungsten oxide or molybdenum oxide; and cyano-containing compounds such as the following compound HT-D1, but not limited thereto:
the hole transport region may include a buffer layer.
Also, the buffer layer may compensate an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of the formed organic light emitting device may be improved.
Meanwhile, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be the above-described material for the hole transport region, a material for a host, which will be described later, or any combination thereof. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be mCP, which will be described later.
The emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, deposition or coating conditions may be similar to those applied when forming the hole injection layer, although the deposition or coating conditions may vary according to the compound used to form the emission layer.
The emission layer may include a host and a dopant, and the dopant may include an organometallic compound represented by formula 1.
The host may comprise TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, mCP, compounds H50 to H52, or any combination thereof:
when the organic light emitting device is a full color organic light emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer. In one embodiment, the emission layer may emit white light due to a stacked structure including a red emission layer, a green emission layer, and/or a blue emission layer.
When the emission layer includes a host and a dopant, the amount of the dopant may be in the range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but the embodiment of the present disclosure is not limited thereto.
The thickness of the emissive layer may be about-about
An electron transport region may be disposed on the emission 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 may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure, but the structure of the electron transport region is not limited thereto. The electron transport layer may have a multilayer structure or a single layer structure including two or more different materials.
The conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer constituting the electron transport region can be understood by referring to the conditions for forming the hole injection layer.
When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, BCP, Bphen, BAlq, or any combination thereof, but embodiments of the present disclosure are not limited thereto:
the hole blocking layer may have a thickness of about
The electron transport layer may comprise BCP, Bphen, Alq3BAlq, TAZ, NTAZ, or any combination thereof:
in one or more embodiments, the electron transport layer may include one of ET1 through ET25, although embodiments of the present disclosure are not limited thereto:
the electron transport layer can have a thickness of about
Also, the electron transport layer may further include a material including a metal in addition to the above-described materials.
The metal-containing material may include a Li complex. The Li complex may include, for example, the compound ET-D1(LiQ), ET-D2, or any combination thereof:
the electron transport region may include an electron injection layer that facilitates the flow of electrons from the
The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, or any combination thereof.
The electron injection layer may have a thickness of about
The
In the foregoing, the organic light emitting device according to the embodiment has been described with respect to fig. 1.
Another aspect of the present disclosure provides a diagnostic composition comprising at least one organometallic compound represented by formula 1.
The organometallic compound represented by formula 1 provides high luminous efficiency. Therefore, a diagnostic composition including the organometallic compound can have high diagnostic efficiency.
The diagnostic compositions are useful in a variety of applications including diagnostic kits, diagnostic reagents, biosensors, and biomarkers.
The term "C" as used herein1-C60The alkyl group "means a straight-chain or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof include methyl, ethyl, n-propyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, and hexyl groups. The term "C" as used herein1-C60Alkylene "means having a bond with C1-C60Alkyl groups are divalent radicals of the same structure.
The term "C" as used herein1-C60Alkoxy "refers to a group consisting of-OA101(wherein A is101Is C1-C60Alkyl), and examples thereof include methoxy, ethoxy, and isopropoxy.
The term "C" as used herein2-C60Alkenyl "is indicated at C2-C60A hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminal of the alkyl group, and examples thereof include a vinyl group, a propenyl group, and a butenyl group. The term "C" as used herein2-C60Alkenylene "means having a group with C2-C60Divalent radicals of the same structure as the alkenyl radicals.
The term "C" as used herein2-C60Alkynyl "means at C2-C60A hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminal of the alkyl group, and examples thereof include an ethynyl group, and a propynyl group. The term "C" as used herein2-C60Alkynylene "means having a bond with C2-C60Bivalent radicals of the same structure as alkynyl radicalsA group.
The term "C" as used herein3-C10Cycloalkyl "refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. The term "C" as used herein3-C10Cycloalkylene "means having an alkyl radical with C3-C10A divalent group of the same structure as the cycloalkyl group.
The term "C" as used herein2-C10Heterocycloalkyl "refers to a monovalent saturated monocyclic group having N, O, P, Si, Se, S, or a combination thereof and 1 to 10 carbon atoms as ring-forming atoms, and non-limiting examples thereof include tetrahydrofuranyl and tetrahydrothienyl. The term "C" as used herein2-C10Heterocycloalkylene "means having a carbon atom with2-C10Heterocycloalkyl groups are divalent radicals of the same structure.
The term "C" as used herein3-C10Cycloalkenyl "refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and no aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. The term "C" as used herein3-C10Cycloalkenyl "means having an alkyl group with C3-C10And (c) divalent groups having the same structure as the cycloalkenyl groups.
The term "C" as used herein2-C10Heterocycloalkenyl "refers to a monovalent monocyclic group having N, O, P, Si, Se, S, or a combination thereof and 2 to 10 carbon atoms as ring-forming atoms in the ring, as well as a double bond. Said C is2-C10Examples of heterocycloalkenyl are 2, 3-dihydrofuranyl and 2, 3-dihydrothienyl. The term "C" as used herein2-C10Heterocycloalkenylene "means having a carbon atom with C2-C10Divalent radicals of the same structure as the heterocycloalkenyl radical.
The term "C" as used herein6-C60Aryl "refers to a carbocyclic aromatic system having 6 to 60 carbon atomsA monovalent group, and the term "C" as used herein6-C60Arylene "refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Said C is6-C60Non-limiting examples of aryl groups include phenyl, naphthyl, anthracyl, phenanthryl, pyrenyl, and
The term "C" as used herein1-C60Heteroaryl "refers to a monovalent group having a heterocyclic aromatic system with N, O, P, Si, Se, S, or combinations thereof, and 1-60 carbon atoms as ring-forming atoms. The term "C" as used herein1-C60Heteroarylene "refers to a divalent group having a heterocyclic aromatic system with N, O, P, Si, Se, S, or any combination thereof as ring-forming atoms. C1-C60Non-limiting examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C is present1-C60Heteroaryl and C1-C60When the heteroarylenes each include two or more rings, the rings may be fused to each other.
The term "C" as used herein6-C60Aryloxy group "represents-OA102(wherein A is102Is C6-C60Aryl), and "C" as used herein6-C60Arylthio "denotes-SA103(wherein A is103Is C6-C60Aryl).
The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group (e.g., having 8 to 60 carbon atoms) as follows: it has two or more rings fused to each other, has only carbon atoms as ring-forming atoms, and has no aromaticity in terms of its entire molecular structure. Examples of the monovalent non-aromatic fused polycyclic group include fluorenyl groups. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group.
The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (e.g., having 2 to 60 carbon atoms) as follows: which has two or more rings fused to each other, has N, O, P, Si, Se, S, or any combination thereof as a ring-forming atom in addition to carbon atoms, and has no aromaticity in terms of its entire molecular structure. Non-limiting examples of the monovalent non-aromatic fused heteropolycyclic group include carbazolyl groups. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic group.
The term "C" as used herein5-C30The carbocyclic group "means a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring-constituting atoms. Said C is5-C30The carbocyclic group may be a monocyclic group or a polycyclic group.
The term "C" as used herein2-C30The heterocyclic group "means a saturated or unsaturated cyclic group having N, O, Si, P, Se, S, or any combination thereof and 2 to 30 carbon atoms as ring-constituting atoms. Said C is2-C3The heterocyclic group may be a monocyclic group or a polycyclic group.
Substituted C5-C30Carbocyclic group, substituted C2-C30Heterocyclic radical, substituted C1-C60Alkyl, substituted C2-C60Alkenyl, substituted C2-C60Alkynyl, substituted C1-C60Alkoxy, substituted C3-C10Cycloalkyl, substituted C2-C10Heterocycloalkyl, substituted C3-C10Cycloalkenyl, substituted C2-C10Heterocycloalkenyl, substituted C6-C60Aryl, substituted C6-C60Aryloxy, substituted C6-C60Arylthio, substituted C1-C60The substituent(s) of the heteroaryl, substituted monovalent non-aromatic fused polycyclic group, and substituted monovalent non-aromatic fused heteropolycyclic group can be:
deuterium, -F, -Cl, -Br, -I, -CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2Hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, or C1-C60An alkoxy group;
c each substituted as follows1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, or C1-C60Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2Hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C3-C10Cycloalkyl radical, C2-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl radical, C2-C10Heterocycloalkenyl, C6-C60Aryl radical, C6-C60Aryloxy radical, C6-C60Arylthio group, C1-C60Heteroaryl, monovalent non-aromatic fused polycyclic radical, monovalent non-aromatic fused heteropolycyclic radical, -N (Q)11)(Q12)、-Si(Q13)(Q14)(Q15)、-B(Q16)(Q17)、-P(＝O)(Q18)(Q19) Or any combination thereof;
C3-C10cycloalkyl radical, C2-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl radical, C2-C10Heterocycloalkenyl, C6-C60Aryl radical, C6-C60Aryloxy radical, C6-C60Arylthio group, C1-C60Heteroaryl radicalA monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group;
c each substituted as follows3-C10Cycloalkyl radical, C2-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl radical, C2-C10Heterocycloalkenyl, C6-C60Aryl radical, C6-C60Aryloxy radical, C6-C60Arylthio group, C1-C60A heteroaryl, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2Hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, C1-C60Alkoxy radical, C3-C10Cycloalkyl radical, C2-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl radical, C2-C10Heterocycloalkenyl, C6-C60Aryl radical, C6-C60Aryloxy radical, C6-C60Arylthio group, C1-C60Heteroaryl, monovalent non-aromatic fused polycyclic radical, monovalent non-aromatic fused heteropolycyclic radical, -N (Q)21)(Q22)、-Si(Q23)(Q24)(Q25)、-B(Q26)(Q27)、-P(＝O)(Q28)(Q29) Or any combination thereof;
-N(Q31)(Q32)、-Si(Q33)(Q34)(Q35)、-B(Q36)(Q37) or-P (═ O) (Q)38)(Q39) (ii) a Or
Any combination thereof.
In this specification, Q1-Q9、Q11-Q19、Q21-Q29And Q31-Q39May each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, C1-C60Alkoxy radical, C3-C10Cycloalkyl radical, C2-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl radical, C2-C10Heterocycloalkenyl radical, C6-C60Aryl radical, quilt C1-C60Alkyl radical, C6-C60Aryl, or any combination thereof substituted C6-C60Aryl radical, C6-C60Aryloxy radical, C6-C60Arylthio group, C1-C60A heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or any combination thereof.
Hereinafter, the compound and the organic light emitting device according to the embodiment are described in detail with reference to synthesis examples and examples. However, the organic light emitting device is not limited thereto. The expression "use of B instead of a" used in describing the synthesis examples means that the amount of B used is the same as the amount of a used in terms of molar equivalents.
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