Organometallic compound, organic light-emitting device including the same, and apparatus including the organic light-emitting device

文档序号:1595143 发布日期:2020-01-07 浏览:20次 中文

阅读说明:本技术 有机金属化合物、包括其的有机发光装置和包括该有机发光装置的设备 (Organometallic compound, organic light-emitting device including the same, and apparatus including the organic light-emitting device ) 是由 金明淑 芮志明 俞炳旭 尹智焕 黄载薰 金宣材 郑在皓 于 2019-06-20 设计创作,主要内容包括:一种有机金属化合物由式1表示。一种有机发光装置包括:第一电极;面向第一电极的第二电极;以及在第一电极和第二电极之间的有机层,有机层包括发光层和至少一种由式1表示的有机金属化合物。一种设备包括上述有机发光装置。(An organometallic compound is represented by formula 1. An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including a light emitting layer and at least one organometallic compound represented by formula 1. An apparatus includes the above organic light emitting device.)

1. An organometallic compound represented by formula 1:

formula 1

Figure FDA0002101261290000011

Wherein, in the formula 1,

m is a transition metal, and M is a transition metal,

ring A1To ring A4Each independently is C5-C60Carbocyclic radical or C1-C60A heterocyclic group,

R1to R4And R11To R14Each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazine, hydrazone, and 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 C1-C10Heterocycloalkyl, substituted or unsubstituted C3-C10Cycloalkenyl, substituted or unsubstituted C1-C10Heterocycloalkenyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C1-C60A heteroaryl group,Substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -O (Q)1)、-S(Q1)、-Si(Q1)(Q2)(Q3)、-N(Q1)(Q2)、-B(Q1)(Q2)、-P(Q1)(Q2)、-C(=O)(Q1)、-S(=O)2(Q1) and-P (═ O) (Q)1)(Q2),

a1 to a4 are each independently an integer of 0 to 10,

a)R11to R14Not simultaneously being hydrogen, b) R11To R14Not simultaneously being phenyl, c) R11To R14Not simultaneously mesityl, and d) R11To R14Is not methyl at the same time,

is selected from R11To R14Are not connected to each other and are not,

said substituted C1-C60Alkyl, said substituted C2-C60Alkenyl, said substituted C2-C60Alkynyl, said substituted C1-C60Alkoxy, said substituted C3-C10Cycloalkyl, said substituted C1-C10Heterocycloalkyl, said substituted C3-C10Cycloalkenyl radical, said substituted C1-C10Heterocycloalkenyl, said substituted C6-C60Aryl, said substituted C1-C60At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteromulticyclic group is selected from the group consisting of:

deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazine, hydrazone, C1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl and C1-C60An alkoxy group;

c each substituted by at least one member selected from the group consisting of1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl and C1-C60Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazine, hydrazone, C3-C10Cycloalkyl radical, C1-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl radical, C1-C10Heterocycloalkenyl, C6-C60Aryl radical, C1-C60Heteroaryl, monovalent non-aromatic fused polycyclic radical, monovalent non-aromatic fused heteropolycyclic radical, -O (Q)11)、-S(Q11)、-Si(Q11)(Q12)(Q13)、-N(Q11)(Q12)、-B(Q11)(Q12)、-P(Q11)(Q12)、-C(=O)(Q11)、-S(=O)2(Q11) and-P (═ O) (Q)11)(Q12);

C3-C10Cycloalkyl radical, C1-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl radical, C1-C10Heterocycloalkenyl, C6-C60Aryl radical, C1-C60A heteroaryl group, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group;

c each substituted by at least one member selected from the group consisting of3-C10Cycloalkyl radical, C1-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl radical, C1-C10Heterocycloalkenyl, C6-C60Aryl radical, C1-C60Heteroaryl, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteromulticyclic group: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazine, hydrazone, C1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, C1-C60Alkoxy radical, C3-C10Cycloalkyl radical, C1-C10Heterocycloalkyl radical, C3-C10Cycloalkenyl radical, C1-C10Heterocycloalkenyl, C6-C60Aryl radical, C1-C60Heteroaryl, monovalent non-aromatic fused polycyclic radicalFused heteropolycyclic radical, -O (Q)21)、-S(Q21)、-Si(Q21)(Q22)(Q23)、-N(Q21)(Q22)、-B(Q21)(Q22)、-P(Q21)(Q22)、-C(=O)(Q21)、-S(=O)2(Q21) and-P (═ O) (Q)21)(Q22) (ii) a And

-O(Q31)、-S(Q31)、-Si(Q31)(Q32)(Q33)、-N(Q31)(Q32)、-B(Q31)(Q32)、-P(Q31)(Q32)、-C(=O)(Q31)、-S(=O)2(Q31) and-P (═ O) (Q)31)(Q32) And is and

Q1to Q3、Q11To Q13、Q21To Q23And Q31To Q33Each independently selected from hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; c1-C60An alkyl group; c2-C60An alkenyl group; c2-C60An alkynyl group; c1-C60An alkoxy group; c3-C10A cycloalkyl group; c1-C10A heterocycloalkyl group; c3-C10A cycloalkenyl group; c1-C10A heterocycloalkenyl group; c6-C60An aryl group; c1-C60A heteroaryl group; a monovalent non-aromatic fused polycyclic group; a monovalent non-aromatic fused heteropolycyclic group; a biphenyl group; a terphenyl group; c substituted by at least one selected from the group consisting of1-C60Alkyl groups: deuterium, -F, cyano, C1-C60Alkyl, phenyl and biphenyl; and C substituted by at least one selected from the group consisting of6-C60Aryl: deuterium, -F, cyano, C1-C10Alkyl, phenyl and biphenyl.

2. The organometallic compound of claim 1 wherein M is platinum, palladium or gold.

3. RightsThe organometallic compound according to claim 1, wherein the ring A is1To ring A4Each independently is phenyl, naphthyl, anthracenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl, chrysenyl, cyclopentadienyl, 1,2,3, 4-tetrahydronaphthyl, thienyl, furyl, pyrrolyl, indolyl, indenyl, benzothiollyl, benzothienyl, benzofuryl, carbazolyl, fluorenyl, dibenzothiapyrrolyl, dibenzothienyl, dibenzofuryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalyl, quinazolinyl, phenanthrolinyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzooxadiazolyl, benzothiadiazolyl, 5,6,7, 8-tetrahydroisoquinolinyl or 5,6,7, 8-tetrahydroquinolyl.

4. The organometallic compound of claim 1 wherein ring a1To ring A4Each independently selected from the group represented by formula 2-1 to formula 2-13:

Figure FDA0002101261290000031

wherein, in formulae 2-1 to 2-13, each of X and X' represents a position of a carbon atom common to the adjacent 5-membered rings, wherein ring A1To ring A4Each of which is fused to the 5-membered ring, respectively.

5. The organometallic compound of claim 1 wherein:

R1to R4And R11To R14Each independently selected from:

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine and hydrazone groups;

each C unsubstituted or substituted by at least one member selected from the group consisting of1-C10Alkyl radical, C2-C10Alkenyl radical, C2-C10Alkynyl and C1-C10Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2Hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, tetrahydro-2H-pyranyl, morpholinyl, phenyl, (C) cyano, nitro, amidino, hydrazino, hydrazone, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornanyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, tetrahydro-2H-pyranyl, and morpholinyl1-C10Alkyl) phenyl, di (C)1-C10Alkyl) phenyl, biphenyl, di (phenyl) phenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, -O (Q)31)、-S(Q31)、-Si(Q31)(Q32)(Q33)、-N(Q31)(Q32)、-B(Q31)(Q32)、-P(Q31)(Q32)、-C(=O)(Q31)、-S(=O)2(Q31) and-P (═ O) (Q)31)(Q32);

Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, tetrahydro-2H-pyranyl, morpholinyl, dioxanyl, phenyl, (C) each unsubstituted or substituted with at least one selected from1-C10Alkyl) phenyl, di (C)1-C10Alkyl) phenyl, biphenyl, di (phenyl) phenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthenyl, benzophenanthryl, pyrenyl, chrysyl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, 2.3-dihydro-1H-indenyl, 1,2,3, 4-tetrahydronaphthyl, 2, 3-dihydrobenzodioxanyl and benzodioxanyl: deuterium, -F, -Cl, -Br, -I, -CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2Hydroxy, cyano, nitro, amidino, hydrazine, hydrazone, C1-C10Alkyl radical, C2-C10Alkenyl radical, C2-C10Alkynyl, C1-C10Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornanyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, tetrahydro-2H-pyranyl, morpholinyl, dioxanyl, phenyl, (C)1-C10Alkyl) phenyl, di (C)1-C10Alkyl) phenyl, biphenyl, di (phenyl) phenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthenyl, benzophenanthryl, pyrenyl, chrysyl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyridyl, imidazopyrimidinyl, 2, 3-dihydro-1H-indenyl, 1,2,3, 4-tetrahydronaphthyl, 2, 3-dihydrobenzodioxanyl and benzodioxanyl, -O (Q)31)、-S(Q31)、-Si(Q31)(Q32)(Q33)、-N(Q31)(Q32)、-B(Q31)(Q32)、-P(Q31)(Q32)、-C(=O)(Q31)、-S(=O)2(Q31) and-P (═ O) (Q)31)(Q32) (ii) a And

-O(Q1)、-S(Q1)、-Si(Q1)(Q2)(Q3)、-N(Q1)(Q2)、-B(Q1)(Q2)、-P(Q1)(Q2)、-C(=O)(Q1)、-S(=O)2(Q1) and-P (═ O) (Q)1)(Q2) And is and

Q1to Q3And Q31To Q33Each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2Hydroxy, cyano, nitro, amidino, hydrazine, hydrazone, C1-C10Alkyl radical, C2-C10Alkenyl radical, C2-C10Alkynyl, C1-C10Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornanyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, tetrahydro-2H-pyranyl, morpholinyl, dioxanyl, phenyl, (C)1-C10Alkyl) phenyl, di (C)1-C10Alkyl) phenyl, biphenyl, di (phenyl) phenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthenyl, benzophenanthryl, pyrenyl, chrysyl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyridyl, imidazopyrimidinyl, 2, 3-dihydro-1H-indenyl, 1,2,3, 4-tetrahydronaphthyl, 2, 3-dihydrobenzodioxanyl and benzodioxanyl.

6. The organometallic compound of claim 1 wherein:

R1to R4Each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I and-CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2、C1-C10Alkyl radical, C2-C10Alkenyl radical, C2-C10Alkynyl, C1-C10Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, phenyl, (C)1-C10Alkyl) phenyl, di (C)1-C10Alkyl) phenyl, biphenyl, di (phenyl) phenyl, terphenyl, -O (Q)1) and-S (Q)1) And is and

Q1is selected from C1-C10Alkyl radical, C2-C10Alkenyl radical, C2-C10Alkynyl, C1-C10Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, phenyl, (C)1-C10Alkyl) phenyl, di (C)1-C10Alkyl) phenyl, biphenyl, di (phenyl) phenyl, and terphenyl.

7. The organometallic compound of claim 1 wherein:

is selected from R11To R14At least one of each is independently selected from C2-C10Alkyl radical, C2-C10Alkenyl radical, C2-C10Alkynyl, C1-C10Alkoxy groups, each of which is unsubstituted or substituted by at least one selected from: deuterium, -F, -Cl, -Br, -I, -CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2Hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, tetrahydro-2H-pyranyl, morpholinyl, phenyl, (C) cyano, nitro, amidino, hydrazino, hydrazone, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornanyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, tetrahydro-2H-pyranyl, and morpholinyl1-C10Alkyl) phenyl, di (C)1-C10Alkyl) phenyl, biphenyl, di (phenyl) phenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, -O (Q)31)、-S(Q31)、-Si(Q31)(Q32)(Q33)、-N(Q31)(Q32)、-B(Q31)(Q32)、-P(Q31)(Q32)、-C(=O)(Q31)、-S(=O)2(Q31) and-P (═ O) (Q)31)(Q32)。

8. The organometallic compound of claim 1 wherein:

is selected from R11To R14Is not any of hydrogen, phenyl, mesityl, and methyl.

9. The organometallic compound of claim 1 wherein:

is selected from R11To R14Is each independently-O (Q)1)、-S(Q1)、-Si(Q1)(Q2)(Q3)、-N(Q1)(Q2)、-B(Q1)(Q2)、-P(Q1)(Q2)、-C(=O)(Q1)、-S(=O)2(Q1)、-P(=O)(Q1)(Q2) Or a group represented by formula a 5:

formula A5

Figure FDA0002101261290000061

Q1To Q3Are each independently the same as defined in claim 1, and

a in the formula A55Is substituted or unsubstituted C1-C10Heterocycloalkyl, substituted or unsubstituted C1-C10Heterocycloalkenyl, substituted or unsubstituted C1-C60Heteroaryl or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

10. The organometallic compound of claim 1 wherein:

a)R11and R12Different from each other, R13And R14Different from each other, R11And R13Are identical to each other, and R12And R14Are identical to each other;

b)R11and R13Different from each other, R12And R14Different from each other, R11And R14Are identical to each other, and R12And R13Are identical to each other;

c)R11and R12Are different from each other, and R11、R13And R14Are identical to each other; or

d)R11To R14All different from each other.

11. The organometallic compound of claim 1 wherein the organometallic compound is selected from compounds 1 to 180:

Figure FDA0002101261290000071

Figure FDA0002101261290000081

Figure FDA0002101261290000091

Figure FDA0002101261290000121

wherein, in the compounds 1 to 180, TMS represents a trimethylsilyl group, and Ph represents a phenyl group.

12. The organometallic compound of claim 1, wherein the organometallic compound emits near infrared phosphorescence having a maximum emission wavelength in a range of 720nm to 2500 nm.

13. An organic light emitting device comprising:

a first electrode;

a second electrode facing the first electrode; and

an organic layer between the first electrode and the second electrode,

wherein the organic layer comprises a light-emitting layer and the organic layer comprises at least one organometallic compound according to any of claims 1-12.

14. The organic light emitting device of claim 13, wherein:

the first electrode is an anode and the second electrode is a cathode,

the second electrode is a cathode, and

the organic layer further includes a hole transport region between the first electrode and the light emitting layer and an electron transport region between the light emitting layer and the second electrode,

the hole transport region comprises a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron blocking layer or any combination thereof, and

the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

15. The organic light-emitting device of claim 13, wherein the light-emitting layer comprises the organometallic compound.

16. The organic light-emitting device of claim 15, wherein the light-emitting layer emits near-infrared phosphorescence having a maximum emission wavelength in a range of 720nm to 2500 nm.

17. The organic light emitting device of claim 14, wherein:

at least one selected from the group consisting of the hole transporting region and the light-emitting layer includes an arylamine group-containing compound, an acridine ring-containing compound and a carbazole ring-containing compound, or

At least one selected from the light-emitting layer and the electron-transporting region includes a silicon-containing compound, a phosphine oxide group-containing compound, a sulfur oxide group-containing compound, a triazine ring-containing compound, a pyrimidine ring-containing compound, a pyridine ring-containing compound, a dibenzofuran ring-containing compound, and a dibenzothiophene ring-containing compound.

18. An apparatus comprising the organic light-emitting device of any one of claims 13-17.

19. The apparatus of claim 18, wherein the apparatus is an electronic device.

20. The apparatus of claim 18, wherein:

the device further comprises a thin film transistor,

the thin film transistor includes a source electrode and a drain electrode, and

the first electrode of the organic light emitting device is electrically coupled with one of the source electrode and the drain electrode of the thin film transistor.

Technical Field

One or more embodiments of the present disclosure relate to an organometallic compound, an organic light-emitting device including the organometallic compound, and an apparatus including the organic light-emitting device.

Background

Organic light emitting devices are self-light emitting devices that produce full color images and also have wide viewing angles, high contrast, short response times, and excellent luminance, driving voltage, and response speed characteristics, compared to other devices in the art.

One example of such an organic light emitting device may include a first electrode disposed on a substrate, and a hole transport region, a light emitting layer, an electron transport region, and a second electrode sequentially disposed on the first electrode. The holes provided from the first electrode may move toward the light emitting layer through the hole transport region, and the electrons provided from the second electrode may move toward the light emitting layer through the electron transport region. Carriers (such as holes and electrons) recombine in the light emitting layer to generate excitons. These excitons transition (e.g., transition or relax) from an excited state to a ground state, thereby generating light.

Disclosure of Invention

One or more embodiments of the present disclosure provide a novel organometallic compound, an organic light-emitting device including the organometallic compound, and an apparatus including the organic light-emitting device.

Drawings

These and/or other aspects of the embodiments will become apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with the accompanying drawings, of which fig. 1 is a schematic view of an organic light-emitting device according to one embodiment.

Additional aspects of the embodiments 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.

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