CN117105988A - Organometallic compound, light-emitting device, electronic device, and electronic apparatus - Google Patents

Organometallic compound, light-emitting device, electronic device, and electronic apparatus Download PDF

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CN117105988A
CN117105988A CN202310573782.7A CN202310573782A CN117105988A CN 117105988 A CN117105988 A CN 117105988A CN 202310573782 A CN202310573782 A CN 202310573782A CN 117105988 A CN117105988 A CN 117105988A
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柳东善
姜东郁
金景宪
金劭姟
金智慧
金会林
朴赛荣
沈龙燮
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Samsung Display Co Ltd
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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Abstract

Provided are an organometallic compound represented by formula 1, and a light-emitting device comprising the organometallic compound represented by formula 1An electronic device including the light emitting device, and an electronic apparatus including the light emitting device. The organometallic compound represented by formula 1 is as described in the specification: 1M (L) 1 ) n1 (L 2 ) n2 。

Description

Organometallic compound, light-emitting device, electronic device, and electronic apparatus
Cross Reference to Related Applications
The present application claims priority and rights of korean patent application No. 10-2022-0063101 filed on 5 months 23 of 2022 and korean patent application No. 10-2022-0141760 filed on 28 of 10 months 2022, each of which is incorporated herein by reference in its entirety.
Technical Field
One or more embodiments of the present disclosure relate to an organometallic compound, a light emitting device including the organometallic compound, an electronic apparatus including the light emitting device, and an electronic device including the light emitting device.
Background
Among light emitting devices, a self-emission device (e.g., an organic light emitting device, etc.) has characteristics of a wide viewing angle, excellent contrast, fast response time, and excellent in brightness, driving voltage, and response speed.
In the light emitting device, a first electrode is on a substrate, and a hole transporting region, an emission layer, an electron transporting region, and a second electrode are sequentially on the first electrode. Holes provided by the first electrode may move toward the emission layer through the hole transport region, and electrons provided by the second electrode may move toward the emission layer through the electron transport region. Carriers such as holes and electrons may recombine in such emissive layers to generate excitons. These excitons transition from an excited state to a ground state to generate light.
Disclosure of Invention
One or more embodiments of the present disclosure include an organometallic compound, a light emitting device having high color purity and forward light emitting efficiency and including the organometallic compound, an electronic apparatus including the light emitting device, and an electronic device including the light emitting device.
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 presented embodiments of the disclosure.
According to one or more embodiments, the organometallic compound is represented by formula 1.
1 (1)
M(L 1 ) n1 (L 2 ) n2
2, 2
2A
M in formula 1 may be a transition metal,
in formula 1, L 1 May be a ligand represented by formula 2, and n1 may be 1, 2 or 3, wherein when n1 is 2 or greater than 2, two or more L 1 May be the same as or different from each other,
in formula 1, L 2 May be an organic ligand, and n2 may be 0, 1 or 2, wherein when n2 is 2, two L' s 2 May be the same as or different from each other,
in formula 1, n1 plus n2 may be equal to 2 or 3,
in the case of the formulas 2 and 2A,
Y 1 it may be that it is N,
Y 2 it may be either C or N,
ring CY 11 May be a nitrogen-containing ring containing at least one N element as a ring-forming atom,
ring CY 12 Cycle CY 21 And a ring CY 22 Can each independently be C 5 -C 30 Carbocyclic group or C 1 -C 30 A heterocyclic group which is a heterocyclic group,
Y 11 to Y 13 And Y 21 To Y 23 May each independently be C or N,
Y 1 and Y 11 、Y 1 And Y 12 、Y 12 And Y 13 、Y 2 And Y 21 、Y 2 And Y 22 And Y 22 And Y 23 May each independently be linked together via a single bond or a double bond,
Y a and Y b Can be each Y in formula 2 23 Or Y 22 Is used for the binding site of (a),
Z 21 can be N (R) 21a )、O、S、Se、C(R 21a )(R 21b ) Or Si (R) 21a )(R 21b )，
R 11 、R 12 、R 21 、R 22 、R 21a And R is 21b Can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl radicals, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkenyl radicals, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkynyl radicals, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkoxy radicals, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkylthio radicals, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclic groups, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclic groups, unsubstitutedOr by at least one R 10a Substituted C 6 -C 60 Aryloxy radicals, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Arylthio group, -C (Q) 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 ) or-P (=O) (Q 1 )(Q 2 )，
d11, d12, d21 and d22 may each independently be an integer of 0 to 20,
R 11 、R 12 、R 21 、R 22 、R 21a and R is 21b Two or more of the groups of (a) may optionally be bonded together to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 60 Carbocyclic groups being either unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 A heterocyclic group which is a heterocyclic group,
* And may each represent a binding site to M in formula 1,
R 10a may be
Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group or a nitro group,
each unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocycle group, C 1 -C 60 Heterocyclic groups, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio groups, C 7 -C 60 Arylalkyl radicals, C 2 -C 60 Heteroarylalkyl group, -Si (Q) 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(＝O)(Q 11 )、-S(＝O) 2 (Q 11 )、-P(＝O)(Q 11 )(Q 12 ) Or any combination thereof 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups or C 1 -C 60 An alkoxy group, a hydroxyl group,
each unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl radicals, C 1 -C 60 Alkoxy groups, C 3 -C 60 Carbocycle group, C 1 -C 60 Heterocyclic groups, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio groups, C 7 -C 60 Arylalkyl radicals, C 2 -C 60 Heteroarylalkyl group, -Si (Q) 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(＝O)(Q 21 )、-S(＝O) 2 (Q 21 )、-P(＝O)(Q 21 )(Q 22 ) Or any combination thereof 3 -C 60 Carbocycle group, C 1 -C 60 Heterocyclic groups, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio groups, C 7 -C 60 Arylalkyl radicals or C 2 -C 60 Heteroarylalkyl group, or
-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 ) or-P (=O) (Q 31 )(Q 32 ) A kind of electronic device
Q 1 To Q 3 、Q 11 To Q 13 、Q 21 To Q 23 Q and 31 to Q 33 May each independently be hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; or each unsubstituted or deuterium, -F, cyano, C 1 -C 60 Alkyl group, C 1 -C 60 C substituted with an alkoxy group, a phenyl group, a biphenyl group, or any combination thereof 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groupGroup C 1 -C 60 Alkoxy groups, C 3 -C 60 Carbocycle group, C 1 -C 60 Heterocyclic groups, C 7 -C 60 Arylalkyl radicals or C 2 -C 60 A heteroarylalkyl group.
According to one or more embodiments, a light emitting device includes a first electrode, a second electrode facing the first electrode, an intermediate layer between the first electrode and the second electrode and including an emission layer, and at least one organometallic compound as described above.
According to one or more embodiments, an electronic device comprises the light emitting arrangement.
According to one or more embodiments, an electronic device comprises the light emitting device.
Drawings
The above and other aspects and features of certain embodiments of the present disclosure will become more apparent from the following description taken in conjunction with the accompanying drawings in which:
fig. 1 is a schematic cross-sectional view of a structure of a light emitting device according to an embodiment;
FIG. 2 is a schematic cross-sectional view of a structure of an electronic device according to an embodiment;
FIG. 3 is a schematic cross-sectional view of the structure of an electronic device according to another embodiment;
fig. 4 is a schematic perspective view of an electronic device including a light emitting device according to an embodiment;
fig. 5 is a schematic perspective view of the outside of a vehicle as an electronic device including a light emitting device according to an embodiment; and
fig. 6A-6C are schematic diagrams of an interior of a vehicle according to various embodiments.
Detailed Description
Reference will now be made in greater detail to embodiments of the present disclosure, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may take various forms and should not be construed as limited to the descriptions set forth herein. Accordingly, only the embodiments are described below by referring to the drawings to explain aspects of the presently described embodiments. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items. Throughout the disclosure, the expression "at least one of a, b and c" means a only, b only, c only, both a and b, both a and c, both b and c, all a, b and c, or variants thereof.
The organometallic compound is represented by formula 1:
1 (1)
M(L 1 ) n1 (L 2 ) n2
2, 2
2A
Wherein M in formula 1 may be a transition metal.
In embodiments, M may be iridium (Ir), osmium (Os), cobalt (Co), platinum (Pt), palladium (Pd), copper (Cu), gold (Au), palladium (Pd), silver (Ag), rhodium (Rh), or ruthenium (Ru).
For example, M may be iridium (Ir), osmium (Os), cobalt (Co), platinum (Pt), palladium (Pd), copper (Cu), or gold (Au).
In formula 1, L 1 May be a ligand represented by formula 2, and n1 may be 1, 2 or 3, wherein when n1 is 2 or greater than 2, two or more L 1 May be the same or different from each other.
In formula 1, L 2 May be an organic ligand, and n2 may be 0, 1 or 2, wherein when n2 is 2, two L' s 2 May be the same or different from each other.
In formula 1, n1 plus n2 may be equal to 2 or 3.
For example, n1 may be 2 and n2 may be 1.
In an embodiment, the organometallic compound represented by formula 1 may be a heteroleptic compound.
In embodiments, L 1 And L 2 May be different ligands, and n2 may be 1 or an integer greater than 1.
In embodiments, M may be iridium or osmium in formula 1 and n1 plus n2 may be equal to 3, or M may be platinum in formula 1 and n1 plus n2 may be equal to 2.
In the case of the formulas 2 and 2A,
Y 1 may be N.
Y 2 May be C or N.
Ring CY 11 May be a nitrogen-containing ring containing at least one N element as a ring-forming atom.
In embodiments, the ring CY 11 May be a pyrrole group, imidazole group, benzimidazole group, indole group, isoindole group, indazole group, purine group, quinoline group, isoquinoline group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group or triazine group.
Ring CY 12 Cycle CY 21 And a ring CY 22 Can each independently be C 5 -C 30 Carbocyclic group or C 1 -C 30 A heterocyclic group.
In embodiments, the ring CY 12 Cycle CY 21 And a ring CY 22 Can be each independently a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a benzophenanthrene group, a pyrene group,A group, a cyclopentadienyl group, a 1,2,3, 4-tetrahydronaphthyl group, a thienyl group, a furanyl group, an indolyl group, a benzoborolan group, a benzophospholan group, an indenyl group, a benzosilol group, a benzogermanium heterocyclopentadienyl group, a benzothiophene group, a benzoselenophene group, a benzofuranyl group, a carboline group, a benzofuranyl group, a benzoborolan group, a benzophospholan group, a benzofuranyl group, a benzoselenophene group, a benzofuranyl group, a benzoborol group, a benzofuranyl group, a benzoAzole groups, dibenzoborolan groups, fluorene groups, dibenzosilole groups, dibenzogermanium heterocyclopentadene groups, dibenzothiophene groups, dibenzoselenophene groups, dibenzofuran groups, dibenzothiophene 5-oxide groups, 9H-fluorene-9-one groups, dibenzothiophene 5, 5-dioxide groups, azaindole groups, azabenzoborolan groups, azabenzophosphole groups, azaindene groups, azabenzosilole groups, azabenzogermanium heterocyclopenadiene groups, azabenzothiophene groups, azabenzoselenophene groups, azabenzofuran groups, azacarbazole groups, azadibenzoborole groups, azadibenzophosphole groups, azafluorene groups, azabenzophosphole groups, azathiophene groups, azabenzopentalene groups, azathiophene groups, and their use in the preparation of a composition Azadibenzosilole groups, azadibenzogermyl heterocyclopentadiene groups, azadibenzothiophene groups, azadibenzoselenophene groups, azadibenzofuran groups, azadibenzothiophene 5-oxide groups, aza-9H-fluorene-9-one groups, azadibenzothiophene 5, 5-dioxide groups, pyridine groups, pyrimidine groups, pyrazine groups, pyridazine groups, triazine groups, quinoline groups, isoquinoline groups, quinoxaline groups, quinazoline groups, phenanthroline groups, pyrrole groups, pyrazole groups, imidazole groups, triazole groups, oxazole groups, isoxazole groups, thiazole groups, isothiazole groups, oxadiazole groups, thiadiazole groups, benzopyrazole groups, benzimidazole groups, benzotriazole groups, benzothiazole groups, benzoxadiazole groups, benzoxazole groups, a benzothiadiazole group, a 5,6,7, 8-tetrahydroisoquinoline group, or a 5,6,7, 8-tetrahydroquinoline group.
Y 11 To Y 13 And Y 21 To Y 23 May each independently be C or N.
Y 1 And Y 11 、Y 1 And Y 12 、Y 12 And Y 13 、Y 2 And Y 21 、Y 2 And Y 22 And Y 22 And Y 23 May each be independently linked together via a single bond or a double bond (e.g., an aromatic double bond or a conjugated double bond).
In the case of the formula (2A),Y a and Y b Can be each Y in formula 2 23 Or Y 22 Is a binding site for a polypeptide.
For example, (i) Y a Can be Y 23 And Y is b Can be Y 22 Or (ii) Y b Can be Y 23 And Y is a Can be Y 22 Is a binding site for a polypeptide.
In formula 2A, Z 21 Can be N (R) 21a )、O、S、Se、C(R 21a )(R 21b ) Or Si (R) 21a )(R 21b )。
In formula 2 and formula 2A, R 11 、R 12 、R 21 、R 22 、R 21a And R is 21b Can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl radicals, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkenyl radicals, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkynyl radicals, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkoxy radicals, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkylthio radicals, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclic groups, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclic groups, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Aryloxy radicals, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Arylthio group, -C (Q) 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 ) or-P (=O) (Q 1 )(Q 2 )。
In embodiments, R 11 、R 12 、R 21 、R 22 、R 21a And R is 21b Each may independently be: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C 1 -C 20 Alkyl groups or C 1 -C 20 An alkoxy group;
each of which is deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl group, cyano group, nitro group, C 1 -C 10 An alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof 1 -C 20 Alkyl groups or C 1 -C 20 An alkoxy group;
each unsubstituted or deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl group, cyano group, nitro group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, adamantyl groups, norbornyl groups, norbornenyl groups, cyclopentenyl groups, cyclohexenyl groups, cycloheptenyl groups, phenyl groups, biphenyl groups, C 1 -C 10 An alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, an anthracyl group, a fluoranthenyl group, a benzophenanthryl group, a pyrenyl group,A alkenyl group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl groupPyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothienyl group, benzothiazolyl group, benzoxazolyl group, benzisoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothienyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, -O (Q) 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 )、-P(＝O)(Q 31 )(Q 32 ) Or any combination thereof, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C 1 -C 10 Alkylphenyl groups, naphthyl groups, fluorenyl groups, phenanthryl groups, anthracyl groups, fluoranthenyl groups, benzophenanthryl groups, pyrenyl groups,>a group selected from the group consisting of a alkenyl group, a alkynyl group, a thienyl group, a furyl group imidazolyl groups, pyrazolyl groups, thiazolyl groups, isothiazolyl groups oxazolyl groups, isoxazolyl groups, pyridinyl groups, pyrazinyl groups, pyrimidinyl groups, pyridazinyl groups isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzamidyl group, and cinnolinyl groupAn oxazolyl group, benzofuranyl group, benzothienyl group, benzisothiazolyl group, benzoxazolyl group, benzisoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothienyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azafluorenyl group, or azadibenzosilol group; or alternatively
-C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 ) or-P (=O) (Q 1 )(Q 2 ) A kind of electronic device
Q 1 To Q 3 And Q 31 To Q 33 Each may independently be:
-CH 3 、-CD 3 、-CD 2 H、-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H、-CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H、-CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 h or-CD 2 CDH 2 The method comprises the steps of carrying out a first treatment on the surface of the Or alternatively
Each unsubstituted or substituted by deuterium, C 1 -C 10 An alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof.
In embodiments, R 11 、R 12 、R 21 、R 22 、R 21a And R is 21b Each may independently be:
hydrogen, deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Cyano group, nitro group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups or C 1 -C 60 An alkoxy group; or alternatively
A group represented by one of the formulas 9-1 to 9-61 or a group represented by one of the formulas 10-1 to 10-246; or alternatively
-C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 ) or-P (=O) (Q 1 )(Q 2 )：
Wherein, in formulas 9-1 to 9-61 and formulas 10-1 to 10-246, represents a binding site to an adjacent atom, ph is a phenyl group, and TMS is a trimethylsilyl group.
In formula 2 and formula 2A, d11, d12, d21, and d22 may each independently be an integer of 0 to 20.
In formula 2 and formula 2A, d11, d12, d21 and d22 respectively represent R 11 、R 12 、R 21 And R is 22 And may each independently be an integer of 0 to 20. When d11 is 2 or greater than 2, two or more R 11 May be the same or different from each other, when d12 is 2 or greater than 2, two or more R 12 May be the same or different from each other, when d21 is 2 or greater than 2, two or more R 21 May be the same or different from each other, and when d22 is 2 or greater than 2, two or more R 22 May be the same or different from each other.
R 11 、R 12 、R 21 、R 22 、R 21a And R is 21b Two or more of the groups of (a) may optionally be bonded together to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 60 Carbocyclic groups being either unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 A heterocyclic group.
In formula 2 and formula 2A, i) d 11R 11 Two or more of which may optionally be bonded together to form an unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic groups being either unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclic group, ii) d 12R 12 Two or more of which may optionally be bonded together to form an unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic groups being either unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclic group, iii) d 21R 21 Two or more of which may optionally be bonded together to form an unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic groups being either unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclic group iv) d 22R 22 Two or more of which may optionally be bonded together to form an unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic groups being either unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclic groups, and v) R 21a And R is 21b May optionally be bonded together to form a group which is unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic groups being either unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group.
In embodiments, d 11R 11 D 12R 12 D 21R 21 D 22R 22 、R 21a And R is 21b May not be hydrogen.
The sum of formula 2 may be a binding site to M in formula 1.
"R" as used in the present specification 10a "may be:
deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group or a nitro group;
each unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocycle group, C 1 -C 60 Heterocyclic groups, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio groups, C 7 -C 60 Arylalkyl radicals, C 2 -C 60 Heteroarylalkyl group, -Si (Q) 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(＝O)(Q 11 )、-S(＝O) 2 (Q 11 )、-P(＝O)(Q 11 )(Q 12 ) Or any combination thereof 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups or C 1 -C 60 An alkoxy group;
each unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl radicals, C 1 -C 60 Alkoxy groups, C 3 -C 60 Carbocycle group, C 1 -C 60 Heterocyclic groups, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio groups, C 7 -C 60 Arylalkyl radicals, C 2 -C 60 Heteroarylalkyl group, -Si (Q) 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(＝O)(Q 21 )、-S(＝O) 2 (Q 21 )、-P(＝O)(Q 21 )(Q 22 ) Or any combination thereof 3 -C 60 Carbocycle group, C 1 -C 60 Heterocyclic groups, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio groups, C 7 -C 60 Arylalkyl radicals or C 2 -C 60 A heteroarylalkyl group; or alternatively
-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 ) or-P (=O) (Q 31 )(Q 32 ) A kind of electronic device
Q 1 To Q 3 、Q 11 To Q 13 、Q 21 To Q 23 Q and 31 to Q 33 Each may independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; or each unsubstituted or deuterium, -F, cyanoGroup C 1 -C 60 Alkyl group, C 1 -C 60 C substituted with an alkoxy group, a phenyl group, a biphenyl group, or any combination thereof 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl radicals, C 1 -C 60 Alkoxy groups, C 3 -C 60 Carbocycle group, C 1 -C 60 Heterocyclic groups, C 7 -C 60 Arylalkyl radicals or C 2 -C 60 A heteroarylalkyl group.
In embodiments, the group represented by formula 2 may be a group represented by formula 2-1 or formula 2-2:
wherein, in the formula 2-1 and the formula 2-2,
Y 1 、Y 2 、CY 11 、CY 12 、CY 21 、CY 22 、Y 11 to Y 13 、Y 21 To Y 23 、Z 21 、R 11 、R 12 、R 21 、R 22 D11, d12, d21, d22, # and # are each the same as described with respect to formulas 2 and 2A.
In embodiments, the group represented by formula 2 may be a group represented by formula 2-11 or formula 2-12:
wherein, in the formulas 2 to 11 and 2 to 12,
X 13 may be C (R) 13 ) Or N, and X 14 May be C (R) 14 ) Or N, or a combination of two,
X 23 may be C (R) 23 ) Or N, and X 24 May be C (R) 24 ) Or N, or a combination of two,
R 13 and R is 14 Can be respectively associated with R 11 The same is described with respect to the case,
R 23 and R is 24 Can be respectively associated with R 21 The same as described, and
Y 1 、Y 2 、CY 12 、CY 22 、Y 12 、Y 13 、Z 21 、R 12 、R 22 d12, d22, and' may each be the same as described with respect to formulas 2 and 2A.
In an embodiment, the compound of formula 2The group represented may be a group represented by one of formulas 3-1 to 3-8:
wherein, in the formulas 3-1 to 3-8,
X 23 may be C (R) 23 ) Or N, X 24 May be C (R) 24 ) Or N, X 25 May be C (R) 25 ) Or N, X 26 May be C (R) 26 ) Or N, X 27 May be C (R) 27 ) Or N, X 28 May be C (R) 28 ) Or N, X 29 May be C (R) 29 ) Or N, or a combination of two,
R 23 to R 29 Can be respectively associated with R 21 The same is described with respect to the case,
Y 2 and Z 21 Can be the same as that described with respect to formula 2 and formula 2A, respectively, and
* 'and' may each represent a binding site to an adjacent atom.
In embodiments, in formulas 3-1 through 3-8, X 23 To X 29 May not be N; or at least one of them may be N.
In an embodiment, the compound of formula 2The group represented by formula 4-1 to formula 4-13 may beA group represented by:
wherein, in the formulas 4-1 to 4-13,
X 13 may be C (R) 13 ) Or N, X 14 May be C (R) 14 ) Or N, X 15 May be C (R) 15 ) Or N, X 16 May be C (R) 16 ) Or N, X 17 May be C (R) 17 ) Or N, X 18 May be C (R) 18 ) Or N, X 19 May be C (R) 19 ) Or N, and X 20 May be C (R) 20 ) Or N, or a combination of two,
Z 19 can be N (R) 19a )、O、S、Se、C(R 19a )(R 19b ) Or Si (R) 19a )(R 19b )，
R 13 To R 20 、R 17a To R 20a And R is 17b To R 20b Can be respectively associated with R 11 The same is described with respect to the case,
Y 1 may be the same as described with respect to formula 2, and
* And "may each represent a binding site to an adjacent atom.
In an embodiment, the compound of formula 2The group represented may be a group represented by one of the formulas 4-1-1 to 4-1-19:
wherein, in the formulas 4-1-1 to 4-1-19,
R 13 to R 18 Can be respectively associated with R 11 The same is described with respect to the case,
Y 1 may be the same as described with respect to formula 2, and
* And "may each represent a binding site to an adjacent atom.
In an embodiment, in formula 1, L 2 Can be represented by one of the formulas 5-1 to 5-6:
wherein, in the formulas 5-1 to 5-6,
Y 51 may be O, N, N (E 51a )、P(E 51a )(E 51b ) Or As (E) 51a )(E 52a )，
Y 52 May be O, N, N (E 52a )、P(E 52a )(E 52b ) Or As (E) 52a )(E 52b )，
T 51 Can be a single bond, a double bond, -C (R 51 )(R 52 )-*'、*-C(R 51 )＝C(R 52 )-*'、*＝C(R 51 )-*'、*-C(R 51 )＝*'、*＝C(R 51 )-C(R 52 )＝C(R 53 )-*'、*-C(R 51 )＝C(R 52 )-C(R 53 ) = or-N (R 51 )-*'，
Y 53 To Y 56 May each independently be C or N,
Y 57 may be C, N (E 57a ) Or P (E) 57a )，
Y 58 Can be N (E 58a )(R 58b )、P(E 58a )(E 58b )(E 58c ) Or As (E) 58a )(E 58b )(E 58c )，Y 59 Can be N (E 59a )(E 59b )、P(E 59a )(E 59b )(E 59c ) Or As (E) 59a )(E 59b )(E 59c )，
Ring A 51 And ring A 52 Can each independently be C 4 -C 60 Carbocycle group or C 1 -C 60 A heterocyclic group which is a heterocyclic group,
E 51 、E 52 、E 51a 、E 51b 、E 52a 、E 52b 、E 57a 、E 58a 、E 58b 、E 58c 、E 59a 、E 59b 、E 59c and R is 51 To R 53 Can be respectively associated with R 11 The same is described with respect to the case,
c51 and c52 may be integers from 0 to 10, and
* And may each represent a binding site to an adjacent atom.
In an embodiment, the organometallic compound represented by formula 1 may be represented by formula 1-1 or formula 1-2:
1-1
1-2
Wherein, in the formulas 1-1 and 1-2,
X 13 may be C (R) 13 ) Or N, X 14 May be C (R) 14 ) Or N, X 15 May be C (R) 15 ) Or N, X 16 May be C (R) 16 ) Or N, X 17 May be C (R) 17 ) Or N, X 18 May be C (R) 18 ) Or N, or a combination of two,
X 23 may be C (R) 23 ) Or N, X 24 May be C (R) 24 ) Or N, or a combination of two,
R 13 to R 18 Can be respectively associated with R 11 The same is described with respect to the case,
R 23 and R is 24 Can be respectively associated with R 21 The same is described with respect to the case,
Y 51 May be O, N, N (E 51a )、P(E 51a )(E 51b ) Or As (E) 51a )(E 52a )，
Y 52 May be O, N, N (E 52a )、P(E 52a )(E 52b ) Or As (E) 52a )(E 52b )，
E 51a 、E 51b 、E 52a 、E 52b And R is 51 To R 53 Can be respectively associated with R 11 The same as described, and
M、n1、Y 1 、Y 2 、CY 22 、Z 21 、R 22 and d22 may each be the same as described with respect to formulas 2 and 2A.
In an embodiment, the organometallic compound represented by formula 1 may emit red light.
In an embodiment, the organometallic compound represented by formula 1 may emit light having a maximum emission wavelength of about 610nm to about 640 nm.
For example, the organometallic compound represented by formula 1 can emit light having a maximum emission wavelength of about 610nm to about 640nm, about 610nm to about 630nm, or about 610nm to about 628 nm.
In an embodiment, the organometallic compound represented by formula 1 may emit light having a full width at half maximum (FWHM) of about 34nm or more and about 58nm or less.
For example, the organometallic compound represented by formula 1 can emit light having a FWHM of about 34nm to about 58nm, about 34nm to about 55nm, about 34nm to about 50nm, about 34nm to about 46nm, or about 40nm to about 46 nm.
In an embodiment, the organometallic compound represented by formula 1 may emit light having a CIE (x) value of about 0.65 or more than 0.65. For example, the organometallic compound represented by formula 1 may emit light having a CIE (x) value of about 0.65 or greater than 0.65, about 0.66 or greater than 0.66 or about 0.67 or greater than 0.67.
In an embodiment, the organometallic compound represented by formula 1 may be, but is not limited to, one of compound 1 to compound 10:
the organometallic compound represented by formula 1 may have i) a group represented by formula 2 and CY represented by formula 2 via N 11 M linked, and ii) a ligand comprising a set or specific orientation (hereinafter, referred to as "orientation A"), wherein CY in formula 2 11 And CY 12 By Y 12 And Y 13 Is connected, and Y in formula 2 22 And Y 23 Respectively with Y in formula 2A a Or Y b And (5) connection.
Since the organometallic compound has a bond to CY via N 11 And thus the electrical stability of the compound can be increased, and the light emitting device including the organometallic compound can emit light having a maximum emission wavelength of about 610nm to about 640 nm.
Further, since the organometallic compound includes the orientation a, the light emitting device including the organometallic compound can emit light having a maximum emission wavelength of about 610nm to about 640nm, and can have a narrow FWHM and excellent light emitting efficiency due to a rigid structure.
The method of synthesizing the organometallic compound represented by formula 1 can be readily understood by one of ordinary skill in the art by referring to the synthesis examples and/or examples described herein.
At least one organometallic compound represented by formula 1 may be used in a light emitting device (e.g., an organic light emitting device). Accordingly, there is provided a light emitting device comprising: a first electrode; a second electrode facing the first electrode; an intermediate layer between the first electrode and the second electrode and comprising an emissive layer; and an organometallic compound represented by formula 1 as described in the present specification.
In the context of an embodiment of the present invention,
the first electrode of the light emitting device may be an anode,
the second electrode of the light emitting device may be a cathode,
the intermediate layer may comprise an organometallic compound,
the intermediate layer may further include a hole transport region between the first electrode and the emissive layer and an electron transport region between the emissive layer and the second electrode,
the hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof, and
the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
In an embodiment, the organometallic compound may be included between a pair of electrodes of the light emitting device. Accordingly, the organometallic compound may be contained in an intermediate layer of the light emitting device, for example, in an emission layer of the intermediate layer.
In an embodiment, the emission layer may further include a host, and the amount of the organometallic compound may be about 0.01 to about 49.99 parts by weight based on 100 parts by weight of the emission layer.
In an embodiment, the emission layer of the light emitting device may include a dopant and a host, and the dopant may include an organometallic compound. For example, an organometallic compound may be used as the dopant. For example, the emission layer may emit green light.
In an embodiment, the emission layer may emit red light.
In an embodiment, the emissive layer may emit light having a maximum emission wavelength of about 610nm to about 640 nm.
For example, the emissive layer may emit light having a maximum emission wavelength of about 610nm to about 640nm, about 610nm to about 630nm, or about 610nm to about 628 nm.
In an embodiment, the emissive layer may emit light having a FWHM of about 34nm or more and about 58nm or less.
For example, the emissive layer may emit light having a FWHM of about 34nm to about 58nm, about 34nm to about 55nm, about 34nm to about 50nm, about 34nm to about 46nm, or about 40nm to about 46 nm.
In embodiments, the emissive layer may emit light having a CIE (x) value of about 0.65 or greater than 0.65. For example, the emissive layer may emit light having a CIE (x) value of about 0.65 or greater than 0.65, about 0.66 or greater than 0.66 or about 0.67 or greater than 0.67.
The expression "(intermediate layer) comprising an organometallic compound" as used herein may mean that (intermediate layer) may comprise one type of organometallic compound represented by formula 1 or two or more different kinds of organometallic compounds each represented by formula 1.
In an embodiment, the intermediate layer may contain only compound 1 as the organometallic compound. In this regard, the compound 1 may be present in an emission layer of a light emitting device. In embodiments, the intermediate layer may include compound 1 and compound 2 as organometallic compounds. In this regard, compound 1 and compound 2 may be present in the same layer (e.g., compound 1 and compound 2 may all be present in the emissive layer), or may be present in different layers (e.g., compound 1 may be present in the emissive layer, and compound 2 may be present in the electron transport region).
The term "intermediate layer" as used herein refers to a single layer and/or multiple layers between a first electrode and a second electrode of a light emitting device.
According to one or more embodiments, there is provided an electronic device comprising a light emitting arrangement as described above. The electronic device may further include a thin film transistor. For example, the electronic device may further include a thin film transistor including a source electrode and a drain electrode, wherein the first electrode of the light emitting device may be electrically coupled to the source electrode or the drain electrode. In embodiments, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. Additional details of the electronic device are the same as described in this specification.
According to one or more embodiments, there is provided an electronic device comprising a light emitting device as described above.
For example, the electronic device may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor light and/or signal light, a heads-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a retractable display, a laser printer, a telephone, a cellular telephone, a tablet personal computer, a tablet telephone, a Personal Digital Assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality display or an augmented reality display, a vehicle, a video wall with multiple displays stitched together, a theatre screen or stadium screen, a phototherapy device, and/or a sign.
Description of FIG. 1
Fig. 1 is a schematic cross-sectional view of a light emitting device 10 according to an embodiment. The light emitting device 10 includes a first electrode 110, an intermediate layer 130, and a second electrode 150.
Hereinafter, a structure of the light emitting device 10 and a method of manufacturing the light emitting device 10 according to the embodiment will be described with respect to fig. 1.
First electrode 110
In fig. 1, the substrate may additionally be below the first electrode 110 and/or above the second electrode 150. In an embodiment, as the substrate, a glass substrate and/or a plastic substrate may be used. In embodiments, the substrate may be a flexible substrate, and may include a plastic having excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.
The first electrode 110 may be formed by, for example, depositing and/or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, a material used to form the first electrode 110 may be a high work function material that facilitates hole injection.
The first electrode 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO) 2 ) Zinc oxide (ZnO) or any combination thereof. In an embodiment, when the first electrode 110 is a transflective electrode or a reflective electrode, a material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg)In), magnesium-silver (Mg-Ag), or any combination thereof.
The first electrode 110 may have a single layer structure composed of a single layer or a multi-layer structure including a plurality of layers. In an embodiment, the first electrode 110 may have a three-layer structure of ITO/Ag/ITO.
Intermediate layer 130
The intermediate layer 130 is over the first electrode 110. The intermediate layer 130 includes an emission layer.
The intermediate layer 130 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 150.
The intermediate layer 130 may further include a metal-containing compound (e.g., an organometallic compound), an inorganic material (e.g., quantum dots), etc., in addition to various suitable organic materials.
In an embodiment, the intermediate layer 130 may include: i) Two or more emission units stacked in sequence between the first electrode 110 and the second electrode 150, and ii) a charge generation layer between the two emission units. When the intermediate layer 130 includes the emission unit and the charge generation layer as described above, the light emitting device 10 may be a tandem light emitting device.
Hole transport region in intermediate layer 130
The hole transport region may have: i) A single layer structure composed of a single layer composed of a single material; ii) a single layer structure consisting of a single layer consisting of a plurality of different materials; or iii) a multilayer structure comprising a plurality of layers comprising different materials.
The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof.
In an embodiment, the hole transport region may have a multi-layer structure including a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, the layers of each structure being stacked in order from the first electrode 110.
The hole transport region may comprise a compound represented by formula 201, a compound represented by formula 202, or any combination thereof:
201, a method for manufacturing a semiconductor device
202, respectively
Wherein, in the formulas 201 and 202,
L 201 to L 204 Can each independently be unsubstituted or substituted with at least one R 10a Substituted divalent C 3 -C 60 Carbocyclic groups being either unsubstituted or substituted by at least one R 10a Substituted divalent C 1 -C 60 A heterocyclic group which is a heterocyclic group,
L 205 can be-O ', -S', -N (Q 201 ) Unsubstituted or substituted by at least one R 10a Substituted C 1 -C 20 Alkylene groups, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 20 An alkenylene group, unsubstituted or substituted by at least one R 10a Substituted divalent C 3 -C 60 Carbocyclic groups, either unsubstituted or substituted by at least one R 10a Substituted divalent C 1 -C 60 Heterocyclic groups x and x' may each represent a binding site to an adjacent atom,
xa1 to xa4 may each independently be an integer of 0 to 5,
xa5 may be an integer from 1 to 10,
R 201 to R 204 And Q 201 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic groups being either unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group which is a heterocyclic group,
R 201 and R is 202 Can optionally be via a single bond, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 5 Alkylene groups being either unsubstituted or substituted by at least one R 10a Substituted C 2 -C 5 The alkenylene groups are linked to each other to form an unsubstituted or substituted with at least one R 10a Substituted C 8 -C 60 Polycyclic groups (e.g., carbazole groups) (see, e.g., compound HT 16),
R 203 and R is 204 Can optionally be via a single bond, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 5 Alkylene groups being either unsubstituted or substituted by at least one R 10a Substituted C 2 -C 5 The alkenylene groups being linked together to form an unsubstituted or substituted with at least one R 10a Substituted C 8 -C 60 A polycyclic group, and
na1 may be an integer from 1 to 4. R is R 10a May be the same as defined herein.
For example, formulas 201 and 202 may each contain at least one of the groups represented by formulas CY201 to CY 217:
wherein, in the formulas CY201 to CY217, R 10b And R is 10c Can be respectively associated with R 10a The same is described for ring CY 201 To ring CY 204 Can each independently be C 3 -C 20 Carbocyclic group or C 1 -C 20 A heterocyclic group, and at least one hydrogen in formulas CY201 to CY217 may be represented by R as described above 10a And (3) substitution. R is R 10a May be the same as defined herein.
In embodiments, a cyclic CY in formulas CY201 through CY217 201 To ring CY 204 May each independently be a phenyl group, a naphthalene group, a phenanthrene group, or an anthracene group.
In embodiments, formulas 201 and 202 may each comprise at least one of the groups represented by formulas CY201 through CY 203.
In embodiments, formula 201 may comprise at least one of the groups represented by formulas CY201 to CY203 and at least one of the groups represented by formulas CY204 to CY 217.
In embodiments, xa1 in formula 201 may be 1, r 201 May be a group represented by one of the formulas CY201 to CY203, xa2 may be 0, and R 202 May be a group represented by one of the formulas CY204 to CY 207.
In embodiments, each of formulas 201 and 202 may not include the group represented by formulas CY201 to CY 203.
In embodiments, each of formulas 201 and 202 may not include the group represented by formulas CY201 to CY203, and may include at least one of the groups represented by formulas CY204 to CY 217.
In embodiments, each of formulas 201 and 202 may not include the group represented by formulas CY201 to CY 217.
For example, the hole transport region may comprise one of the compounds HT1 through HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β -NPB, TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4' -tris (N-carbazolyl) triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (PANI/CSA), polyaniline/poly (4-styrenesulfonate) (PANI/PSS), or any combination thereof:
the thickness of the hole transport region may be aboutTo about->For example, about->To aboutWhen the hole transport region comprises a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be about +. >To about->For example about->To about->And the thickness of the hole transport layer may be about +.>To about->For example about->To about->When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, suitable or satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage.
The emission auxiliary layer may increase light emission efficiency by compensating an optical resonance distance according to a wavelength of light emitted by the emission layer, and the electron blocking layer may block or reduce leakage of electrons from the emission layer to the hole transport region. The material that may be contained in the hole transport region may be contained in the emission assistance layer and the electron blocking layer.
P-dopant
In addition to these materials, the hole transport region may further include a charge generating material for improving conductive properties (e.g., conductive properties). The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer composed of the charge generating material).
The charge generating material may be, for example, a p-dopant.
In embodiments, the Lowest Unoccupied Molecular Orbital (LUMO) level of the p-dopant may be about-3.5 eV or less than-3.5 eV.
In embodiments, the p-dopant may include quinone derivatives, cyano group-containing compounds, compounds comprising element EL1 and element EL2, or any combination thereof.
Examples of the quinone derivative may include TCNQ, F4-TCNQ, and the like.
Examples of the cyano group-containing compound may include HAT-CN, a compound represented by formula 221, and the like.
221 of a pair of rollers
In the process of 221,
R 221 to R 223 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic groups being either unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclic group, R 10a May be the same as defined herein, and
R 221 to R 223 May each be independently of the other, each of which is: a cyano group; -F; -Cl; -Br; -I; c substituted with cyano groups, -F, -Cl, -Br, -I or any combination thereof 1 -C 20 An alkyl group; or any combination thereof 3 -C 60 Carbocyclic group or C 1 -C 60 A heterocyclic group.
In the compound containing the element EL1 and the element EL2, the element EL1 may be a metal, a metalloid, or a combination thereof, and the element EL2 may be a nonmetal, a metalloid, or a combination thereof.
Examples of metals may include: alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.; post-transition metals (e.g., zinc (Zn), indium (In), tin (Sn), etc.); and lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.).
Examples of metalloids may include silicon (Si), antimony (Sb), and tellurium (Te).
Examples of nonmetallic materials may include oxygen (O) and halogen (e.g., F, cl, br, I, etc.).
In embodiments, examples of compounds comprising elements EL1 and EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, and/or metal iodides), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, and/or metalloid iodides), metal tellurides, or any combination thereof.
Examples of the metal oxide may include tungsten oxide (e.g., WO, W 2 O 3 、WO 2 、WO 3 、W 2 O 5 Etc.), vanadium oxides (e.g., VO, V 2 O 3 、VO 2 、V 2 O 5 Etc.), molybdenum oxides (e.g., moO, mo 2 O 3 、MoO 2 、MoO 3 、Mo 2 O 5 Etc.) and rhenium oxide (e.g., reO 3 Etc.).
Examples of the metal halide may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and lanthanide metal halides.
Examples of the alkali metal halide may include LiF, naF, KF, rbF, csF, liCl, naCl, KCl, rbCl, csCl, liBr, naBr, KBr, rbBr, csBr, liI, naI, KI, rbI and CsI.
Examples of alkaline earth metal halides may include BeF 2 、MgF 2 、CaF 2 、SrF 2 、BaF 2 、BeCl 2 、MgCl 2 、CaCl 2 、SrCl 2 、BaCl 2 、BeBr 2 、MgBr 2 、CaBr 2 、SrBr 2 、BaBr 2 、BeI 2 、MgI 2 、CaI 2 、SrI 2 And BaI 2 。
Examples of transition metal halides may include titanium halides (e.g., tiF 4 、TiCl 4 、TiBr 4 、TiI 4 Etc.), zirconium halides (e.g., zrF 4 、ZrCl 4 、ZrBr 4 、ZrI 4 Etc.), hafnium halides (e.g., hfF 4 、HfCl 4 、HfBr 4 、HfI 4 Etc.), vanadium halides (e.g., VF 3 、VCl 3 、VBr 3 、VI 3 Etc.), niobium halides (e.g., nbF 3 、NbCl 3 、NbBr 3 、NbI 3 Etc.), tantalum halides (e.g., taF 3 、TaCl 3 、TaBr 3 、TaI 3 Etc.), chromium halides (e.g., crF 3 、CrCl 3 、CrBr 3 、CrI 3 Etc.), molybdenum halides (e.g., moF 3 、MoCl 3 、MoBr 3 、MoI 3 Etc.), tungsten halides (e.g., WF 3 、WCl 3 、WBr 3 、WI 3 Etc.), manganese halides (e.g., mnF 2 、MnCl 2 、MnBr 2 、MnI 2 Etc.), technetium halides (e.g., tcF 2 、TcCl 2 、TcBr 2 、TcI 2 Etc.), rhenium halides (e.g., ref 2 、ReCl 2 、ReBr 2 、ReI 2 Etc.), iron halides (e.g., feF 2 、FeCl 2 、FeBr 2 、FeI 2 Etc.), ruthenium halides (e.g., ruF 2 、RuCl 2 、RuBr 2 、RuI 2 Etc.), osmium halides (e.g., osF 2 、OsCl 2 、OsBr 2 、OsI 2 Etc.), cobalt halides (e.g., coF 2 、CoCl 2 、CoBr 2 、CoI 2 Etc.), rhodium halides (e.g., rhF 2 、RhCl 2 、RhBr 2 、RhI 2 Etc.), iridium halides (e.g., irF 2 、IrCl 2 、IrBr 2 、IrI 2 Etc.), nickel halides (e.g., niF 2 、NiCl 2 、NiBr 2 、NiI 2 Etc.), palladium halides (e.g., pdF 2 、PdCl 2 、PdBr 2 、PdI 2 Etc.), platinum halides (e.g., ptF 2 、PtCl 2 、PtBr 2 、PtI 2 Etc.), copper halides (e.g., cuF, cuCl, cuBr, cuI, etc.), silver halides (e.g., agF, agCl, agBr, agI, etc.), and gold halides (e.g., auF, auCl, auBr, auI, etc.).
Solid post-transition metal halidesExamples may include zinc halides (e.g., znF 2 、ZnCl 2 、ZnBr 2 、ZnI 2 Etc.), indium halides (e.g., inI 3 Etc.) and tin halides (e.g., snI 2 Etc.).
Examples of lanthanide metal halides may include YbF, ybF 2 、YbF 3 、SmF 3 、YbCl、YbCl 2 、YbCl 3 、SmCl 3 、YbBr、YbBr 2 、YbBr 3 、SmBr 3 、YbI、YbI 2 、YbI 3 And SmI 3 。
Examples of metalloid halides may include antimony halides (e.g., sbCl 5 Etc.).
Examples of the metal telluride may include alkali metal telluride (e.g., li 2 Te、Na 2 Te、K 2 Te、Rb 2 Te、Cs 2 Te, etc.), alkaline earth metal telluride (e.g., beTe, mgTe, caTe, srTe, baTe, etc.), transition metal telluride (e.g., tiTe 2 、ZrTe 2 、HfTe 2 、V 2 Te 3 、Nb 2 Te 3 、Ta 2 Te 3 、Cr 2 Te 3 、Mo 2 Te 3 、W 2 Te 3 、MnTe、TcTe、ReTe、FeTe、RuTe、OsTe、CoTe、RhTe、IrTe、NiTe、PdTe、PtTe、Cu 2 Te、CuTe、Ag 2 Te、AgTe、Au 2 Te, etc.), late transition metal telluride (e.g., znTe, etc.), and lanthanide metal telluride (e.g., laTe, ceTe, prTe, ndTe, pmTe, euTe, gdTe, tbTe, dyTe, hoTe, erTe, tmTe, ybTe, luTe, etc.).
Emissive layer in intermediate layer 130
When the light emitting device 10 is a full color light emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer according to the sub-pixels. In embodiments, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer, and a blue emission layer, wherein the two or more layers may be in contact with each other (e.g., in physical contact) or may be spaced apart from each other. In embodiments, the emissive layer may comprise two or more of a red light emitting material, a green light emitting material, and a blue light emitting material, wherein the two or more materials may be mixed with each other in a single layer to emit white light.
The emissive layer may include a host and a dopant. The dopant may include phosphorescent dopants, fluorescent dopants, or any combination thereof.
The amount of dopant in the emissive layer may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
In embodiments, the emissive layer may comprise quantum dots.
In embodiments, the emissive layer may comprise a delayed fluorescent material. The delayed fluorescent material may be used as a host or as a dopant in the emissive layer.
The thickness of the emissive layer may be aboutTo about->Or, for example, about-> To aboutWhen the thickness of the emission layer is within the foregoing range, excellent light emission characteristics can be obtained without a significant increase in driving voltage.
Main body
The host may include a compound represented by formula 301:
301
[Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21
Wherein, in the formula 301,
Ar 301 may be unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclic groups being either unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclic groups, L 301 May be unsubstituted or substituted by at least one R 10a Substituted divalent C 3 -C 60 Carbocyclic groups being either unsubstituted or substituted by at least one R 10a Substituted divalent C 1 -C 60 A heterocyclic group which is a heterocyclic group,
xb11 may be 1, 2 or 3,
xb1 may be an integer from 0 to 5,
R 301 can be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl radicals, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkenyl radicals, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkynyl radicals, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkoxy radicals, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclic groups, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si (Q) 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(＝O)(Q 301 )、-S(＝O) 2 (Q 301 ) or-P (=O) (Q 301 )(Q 302 )，
xb21 may be an integer from 1 to 5, R 10a May be the same as defined herein, and
Q 301 to Q 303 Can be respectively related to Q 1 The description is the same.
For example, when xb11 in formula 301 is 2 or greater than 2, two or more Ar' s 301 May be connected together via a single bond.
In embodiments, the host may include a compound represented by formula 301-1, a compound represented by formula 301-2, or any combination thereof:
301-1
301-2
Wherein, in the formulas 301-1 and 301-2,
ring A 301 To ring A 304 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic groups being either unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclic group, R 10a May be the same as defined herein,
X 301 can be O, S, N [ (L) 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) Or Si (R) 304 )(R 305 )，
xb22 and xb23 may each independently be 0, 1 or 2,
L 301 Xb1 and R 301 May each be the same as described in the present specification,
L 302 to L 304 Can be each independently related to L 301 The same is described with respect to the case,
xb2 to xb4 may each independently be the same as described for xb1, and
R 302 to R 305 R is as follows 311 To R 314 Can be respectively associated with R 301 The description is the same.
In embodiments, the host may include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. For example, the host may include Be complex (e.g., compound H55), mg complex, zn complex, or any combination thereof.
In embodiments, the host may include one of compound H1 to compound H124, 9, 10-bis (2-naphthyl) Anthracene (ADN), 2-methyl-9, 10-bis (naphthalen-2-yl) anthracene (MADN), 9, 10-bis (2-naphthyl) -2-tert-butyl-anthracene (TBADN), 4 '-bis (N-carbazolyl) -1,1' -biphenyl (CBP), 1, 3-bis (9-carbazolyl) benzene (mCP), 1,3, 5-tris (carbazol-9-yl) benzene (TCP), or any combination thereof:
phosphorescent dopants
The phosphorescent dopant may include at least one transition metal as a central metal.
Phosphorescent dopants may include monodentate ligands, bidentate ligands, tridentate ligands, tetradentate ligands, pentadentate ligands, hexadentate ligands, or any combination thereof.
Phosphorescent dopants may be electrically neutral.
For example, the phosphorescent dopant may include an organometallic compound represented by formula 401:
401
M(L 401 ) xc1 (L 402 ) xc2
402 of the following kind
Wherein, in the formulas 401 and 402,
m may be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),
L 401 may be a ligand represented by formula 402, and xc1 may be 1, 2, or 3, wherein when xc1 is 2 or greater than 2, two or more L 401 May be the same as or different from each other,
L 402 may be an organic ligand, and xc2 may be 0, 1, 2, 3 or 4, wherein when xc2 is 2 or greater than 2, two or more L' s 402 May be the same as or different from each other,
X 401 and X 402 May each independently be nitrogen or carbon,
ring A 401 And ring A 402 Can each independently be C 3 -C 60 Carbocycle group or C 1 -C 60 A heterocyclic group which is a heterocyclic group,
T 401 can be a single bond, —o ', -S', -C (=o) -, -N (Q) 411 )-*'、*-C(Q 411 )(Q 412 )-*'、*-C(Q 411 )＝C(Q 412 )-*'、*-C(Q 411 ) Either = 'or = C =, and =' may each represent a binding site with an adjacent atom,
X 403 and X 404 May each independently be a chemical bond (e.g., a covalent bond or a coordinate bond, which may also be referred to as a coordinate covalent bond or a coordinate bond), O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) Or Si (Q) 413 )(Q 414 )，
Q 411 To Q 414 Can be respectively associated withAt Q 1 The same is described with respect to the case,
R 401 And R is 402 Can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 20 Alkyl radicals, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 20 Alkoxy radicals, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclic groups, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si (Q) 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(＝O)(Q 401 )、-S(＝O) 2 (Q 401 ) or-P (=O) (Q 401 )(Q 402 )，
Q 401 To Q 403 Can be respectively related to Q 1 The descriptions are the same, R 10a May be the same as defined herein,
xc11 and xc12 may each independently be an integer of 0 to 10, and
the sum of formulas 402 may each represent a binding site to M in formula 401.
For example, in formula 402, i) X 401 May be nitrogen, and X 402 May be carbon, or ii) X 401 And X 402 May be nitrogen.
In embodiments, when xc1 in formula 401 is 2 or greater than 2, two or more L 401 Two rings A in (a) 401 Optionally via T as a linking group 402 Are connected to each other, and two or more than two L 401 Two rings A in (a) 402 Optionally via T as a linking group 403 Are linked to each other (see compound PD1 to compound PD4 and compound PD 7). T (T) 402 And T 403 Can be respectively related to T 401 The description is the same.
L in formula 401 402 May be an organic ligand. For example, L 402 May include halogen groups, diketone groups (e.g., acetylacetonate groups), carboxylic acid groups (e.g., picolinate groups), -C (=o), isonitrile groups, -CN, phosphorus-containing groups (e.g., phosphine groups or phosphite groups), or any combination thereof.
Phosphorescent dopants may include, for example, one of compounds PD1 through PD39, or any combination thereof:
fluorescent dopants
The fluorescent dopant may include an amine group-containing compound, a styrene group-containing compound, or any combination thereof.
For example, the fluorescent dopant may include a compound represented by formula 501:
501, a method of manufacturing a semiconductor device
Wherein, in the formula 501,
Ar 501 、R 501 and R is 502 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic groups being either unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclic groups, L 501 To L 503 Can each independently be unsubstituted or substituted with at least one R 10a Substituted divalent C 3 -C 60 Carbocyclic groups being either unsubstituted or substituted by at least one R 10a Substituted divalent C 1 -C 60 Heterocyclic group, R 10a May be the same as defined herein,
xd1 to xd3 can each independently be 0, 1, 2 or 3, and
xd4 may be 1, 2, 3, 4, 5 or 6.
For example, ar in formula 501 501 May be a condensed cyclic group in which three or more monocyclic groups are condensed together (e.g., an anthracene group,A group or a pyrene group).
In an embodiment, xd4 in formula 501 may be 2.
For example, the fluorescent dopant may include: compound FD1 to compound FD36; DPVBi; one of DPAVBi; or any combination thereof:
delayed fluorescent material
The emissive layer may comprise a delayed fluorescent material.
In the present specification, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
Depending on the type (or kind) of other materials contained in the emissive layer, the delayed fluorescent material contained in the emissive layer may act as a host or dopant.
In embodiments, the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material may be greater than or equal to about 0eV and less than or equal to about 0.5eV. When the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material satisfies the above-described range, up-conversion of the delayed fluorescent material from the triplet state to the singlet state may effectively occur, and thus the light emitting efficiency of the light emitting device 10 may be improved.
For example, the delayed fluorescent material may include i) a fluorescent material containing at least one electron donor (e.g., pi-electron rich C 3 -C 60 Cyclic groups, e.g. carbazole groups), and at least one electron acceptor (e.g. sulfoxide groups, cyano groups or pi-electron deficient nitrogen-containing C 1 -C 60 Cyclic groups), and ii) C comprising a group in which two or more cyclic groups are fused together while sharing boron (B) 8 -C 60 Materials with polycyclic groups.
Examples of the delayed fluorescent material may include at least one of the following compounds DF1 to DF 9:
quantum dot
The emissive layer may comprise quantum dots.
In the present specification, quantum dots may refer to crystals of a semiconductor compound, and may include any suitable material capable of emitting light of various suitable emission wavelengths according to the size of the crystals.
The diameter of the quantum dots may be, for example, from about 1nm to about 10nm.
The quantum dots may be synthesized by wet chemical processes, metal organic chemical vapor deposition processes, molecular beam epitaxy processes, and/or any suitable process similar thereto.
Wet chemical processes are methods that include mixing precursor materials with an organic solvent and then growing crystals of quantum dot particles. When the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal, so that the growth of the quantum dot particles can be controlled by a process which is lower in cost and easier than vapor deposition methods such as Metal Organic Chemical Vapor Deposition (MOCVD) or Molecular Beam Epitaxy (MBE),
The quantum dots may include: a group II-VI semiconductor compound; a group III-V semiconductor compound; a group III-VI semiconductor compound; a group I-III-VI semiconductor compound; group IV-VI semiconductor compounds; group IV elements or compounds; or any combination thereof.
Examples of the group II-VI semiconductor compound may include: binary compounds such as CdS, cdSe, cdTe, znS, znSe, znTe, znO, hgS, hgSe, hgTe, mgSe and/or MgS; ternary compounds such as CdSeS, cdSeTe, cdSTe, znSeS, znSeTe, znSTe, hgSeS, hgSeTe, hgSTe, cdZnS, cdZnSe, cdZnTe, cdHgS, cdHgSe, cdHgTe, hgZnS, hgZnSe, hgZnTe, mgZnSe and/or MgZnS; quaternary compounds, such as CdZnSeS, cdZnSeTe, cdZnSTe, cdHgSeS, cdHgSeTe, cdHgSTe, hgZnSeS, hgZnSeTe and/or HgZnSTe; or any combination thereof.
Examples of the group III-V semiconductor compound may include: binary compounds such as GaN, gaP, gaAs, gaSb, alN, alP, alAs, alSb, inN, inP, inAs and/or InSb; ternary compounds, such as GaNP, gaNAs, gaNSb, gaPAs, gaPSb, alNP, alNAs, alNSb, alPAs, alPSb, inGaP, inNP, inAlP, inNAs, inNSb, inPAs and/or InPSb; quaternary compounds, such as GaAlNP, gaAlNAs, gaAlNSb, gaAlPAs, gaAlPSb, gaInNP, gaInNAs, gaInNSb, gaInPAs, gaInPSb, inAlNP, inAlNAs, inAlNSb, inAlPAs and/or InAlPSb; or any combination thereof. In embodiments, the group III-V semiconductor compound may further comprise a group II element. Examples of the group III-V semiconductor compound further containing a group II element may include InZnP, inGaZnP, inAlZnP and the like.
Examples of the group III-VI semiconductor compound may include: binary compounds, e.g. GaS, gaSe, ga 2 Se 3 、GaTe、InS、InSe、In 2 S 3 、In 2 Se 3 And/or inet; ternary compounds, e.g. InGaS 3 And/or InGaSe 3 The method comprises the steps of carrying out a first treatment on the surface of the Or any combination thereof.
Examples of the group I-III-VI semiconductor compound may include: ternary compounds, e.g. AgInS, agInS 2 、CuInS、CuInS 2 、CuGaO 2 、AgGaO 2 And/or AgAlO 2 The method comprises the steps of carrying out a first treatment on the surface of the Or alternativelyAny combination thereof.
Examples of the IV-VI semiconductor compound may include: binary compounds such as SnS, snSe, snTe, pbS, pbSe, pbTe and the like; ternary compounds, such as SnSeS, snSeTe, snSTe, pbSeS, pbSeTe, pbSTe, snPbS, snPbSe, snPbTe, etc.; quaternary compounds, such as SnPbSSe, snPbSeTe, snPbSTe, etc.; or any combination thereof.
The group IV element or compound may include: a single element, such as Si or Ge; binary compounds such as SiC and/or SiGe; or any combination thereof.
Each element contained in the multi-element compound (e.g., binary, ternary, and/or quaternary) may be present in particles having a uniform concentration or a non-uniform concentration.
In embodiments, the quantum dots may have a single structure or a core-shell double structure. In the case where the quantum dots have a single structure, the concentration of each element contained in the respective quantum dots may be uniform (e.g., substantially uniform). In embodiments, the material contained in the core and the material contained in the shell may be different from each other.
The shell of the quantum dot may act as a protective layer that prevents or reduces chemical denaturation of the core to maintain semiconductor properties and/or a charge layer that imparts electrophoretic properties to the quantum dot. The shell may be a single layer or multiple layers. The element present in the interface between the core and the shell of the quantum dot may have a concentration gradient that decreases in a direction toward the center of the quantum dot.
Examples of shells forming the quantum dots may include oxides of metals, metalloids, or non-metals, semiconductor compounds, and any combination thereof. Examples of metal, metalloid or non-metal oxides may include: binary compounds, e.g. SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3 、Mn 3 O 4 、CuO、FeO、Fe 2 O 3 、Fe 3 O 4 、CoO、Co 3 O 4 And/or NiO; ternary compounds, e.g. MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 And/or CoMn 2 O 4 The method comprises the steps of carrying out a first treatment on the surface of the Or any combination thereof. Examples of semiconductor compounds may include group II-VI semiconductor compounds, group III-V semiconductor compounds, group III-VI semiconductor compounds, group I-III-VI semiconductor compounds, group IV-VI semiconductor compounds, or any combination thereof, as described herein. Further, the semiconductor compound may include CdS, cdSe, cdTe, znS, znSe, znTe, znSeS, znTeS, gaAs, gaP, gaSb, hgS, hgSe, hgTe, inAs, inP, inGaP, inSb, alAs, alP, alSb or any combination thereof.
The FWHM of the emission wavelength spectrum of the quantum dot may be about 45nm or less than 45nm, for example about 40nm or less than 40nm, or, for example, about 30nm or less than 30nm, and within these ranges, color purity and/or color reproducibility may be increased. Furthermore, since light emitted by the quantum dots is emitted in all (e.g., substantially all) directions, a wide viewing angle can be improved.
Further, the quantum dots may be spherical nanoparticles, pyramidal nanoparticles, multi-arm nanoparticles, cubic nanoparticles, nanotubes, nanowires, nanofibers, and/or nanoplates.
Since the band gap can be adjusted by controlling the size of the quantum dot, light having various suitable wavelength bands can be obtained from the quantum dot emission layer. Thus, by using quantum dots of different sizes, a light emitting device that emits light of various suitable wavelengths can be realized. In embodiments, the size of the quantum dots may be selected to emit red, green, and/or blue light. Further, the size of the quantum dots may be configured to emit white light by combining light of various suitable colors.
Electron transport regions in intermediate layer 130
The electron transport region may have: i) A single layer structure composed of a single layer composed of a single material, ii) a single layer composed of a plurality of different materials, or iii) a multi-layer structure including a plurality of layers including different materials.
The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
For example, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, the constituent layers of each of which are stacked in order from the emission layer.
The electron transport region (e.g., buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may comprise a nitrogen-containing C containing at least one pi-deficient electron 1 -C 60 Metal-free compounds of cyclic groups.
In an embodiment, the electron transport region may comprise a compound represented by formula 601:
601 and method for manufacturing the same
[Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 。
Wherein, in the formula 601,
Ar 601 may be unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclic groups being either unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclic groups, L 601 May be unsubstituted or substituted by at least one R 10a Substituted divalent C 3 -C 60 Carbocyclic groups being either unsubstituted or substituted by at least one R 10a Substituted divalent C 1 -C 60 A heterocyclic group which is a heterocyclic group,
xe11 may be 1, 2 or 3,
xe1 may be 0, 1, 2, 3, 4 or 5,
R 601 may be unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclic groups, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si (Q) 601 )(Q 602 )(Q 603 )、-C(＝O)(Q 601 )、-S(＝O) 2 (Q 601 ) or-P (=O) (Q 601 )(Q 602 )，Q 601 To Q 603 Can be each independently related to Q 1 The same is described with respect to the case,
xe21 may be 1, 2, 3, 4 or 5, and
at least one of the following conditions may be satisfied: ar (Ar) 601 May be unsubstituted or substituted by at least one R 10a Substituted pi electron deficient nitrogen containing C 1 -C 60 A cyclic group; r is R 601 May be unsubstituted or substituted by at least one R 10a Substituted pi electron deficient nitrogen containing C 1 -C 60 A cyclic group; l and 601 may be unsubstituted or substituted by at least one R 10a Substituted divalent pi electron deficient nitrogen containing C 1 -C 60 A cyclic group. R is R 10a May be the same as defined herein.
In embodiments, when xe11 in formula 601 is 2 or greater than 2, two or more Ar 601 Can be connected to each other via a single bond.
In an embodiment, ar in formula 601 601 May be a substituted or unsubstituted anthracene group.
In an embodiment, the electron transport region may comprise a compound represented by formula 601-1:
601-1
Wherein, in the formula 601-1,
X 614 can be N or C (R 614 )，X 615 Can be N or C (R 615 )，X 616 Can be N or C (R 616 ) And X is 614 To X 616 At least one of which may be N,
L 611 to L 613 Can be each independently related to L 601 The same is described with respect to the case,
xe611 to xe613 may each be independently the same as described with respect to xe1,
R 611 to R 613 Can be each independently and relative to R 601 The same is described with respect to the case,and
R 614 to R 616 Can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy radicals, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclic groups being either unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group.
In embodiments, xe1 and xe611 through xe613 in formulas 601 and 601-1 may each independently be 0, 1, or 2.
The electron transport region may comprise compounds ET1 to ET45, 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 4, 7-diphenyl-1, 10-phenanthroline (Bphen), alq 3 One of, BAlq, TAZ, NTAZ, or any combination thereof:
the thickness of the electron transport region may be aboutTo about->For example about->To about->When the electron transport region comprises a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be about >To about->For example about->To about->And the thickness of the electron transport layer may be about +.>To about->For example about->To aboutWhen the thicknesses of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region are within these ranges, suitable or satisfactory electron transport characteristics can be obtained without a significant increase in driving voltage.
In addition to the materials described above, the electron transport region (e.g., the electron transport layer in the electron transport region) may further comprise a metal-containing material.
The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ion of the alkali metal complex may Be Li ion, na ion, K ion, rb ion or Cs ion, and the metal ion of the alkaline earth metal complex may Be ion, mg ion, ca ion, sr ion or Ba ion. The ligand that coordinates to the metal ion of the alkali metal complex or alkaline earth metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
In embodiments, the metal-containing material may include a Li complex. The Li complex may include, for example, the compound ET-D1 (Liq) or the compound ET-D2:
the electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 150. The electron injection layer may be in direct contact (e.g., physical contact) with the second electrode 150.
The electron injection layer may have: i) A single layer structure composed of a single layer composed of a single material, ii) a single layer composed of a plurality of different materials, or iii) a multi-layer structure including a plurality of layers including different materials.
The electron injection layer may comprise an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
The alkali metal may include Li, na, K, rb, cs or any combination thereof. The alkaline earth metal may include Mg, ca, sr, ba or any combination thereof. The rare earth metal may include Sc, Y, ce, tb, yb, gd or any combination thereof.
The alkali metal-containing compound, alkaline earth metal-containing compound, and rare earth metal-containing compound may include alkali metal, alkaline earth metal, and rare earth metal oxides, halides (e.g., fluorides, chlorides, bromides, and/or iodides), and/or tellurides, or any combination thereof.
The alkali metal-containing compound may include an alkali metal oxide (e.g., li 2 O、Cs 2 O and/or K 2 O), alkali metal halides (e.g., liF, naF, csF, KF, liI, naI, csI and/or KI), or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal oxide, e.g. BaO, srO, caO, ba x Sr 1-x O (x is 0<x<Real number of condition 1), ba x Ca 1-x O (x is 0<x<A real number of the condition of 1), and the like. The rare earth metal-containing compound may include YbF 3 、ScF 3 、Sc 2 O 3 、Y 2 O 3 、Ce 2 O 3 、GdF 3 、TbF 3 、YbI 3 、ScI 3 、TbI 3 Or any combination thereof. In embodiments, the rare earth metal-containing compound may include a lanthanide metal telluride. Examples of lanthanide metal telluride may include LaTe, ceTe, prTe, ndTe, pmTe, smTe, euTe, gdTe, tbTe, dyTe, hoTe, erTe, tmTe, ybTe, luTe, la 2 Te 3 、Ce 2 Te 3 、Pr 2 Te 3 、Nd 2 Te 3 、Pm 2 Te 3 、Sm 2 Te 3 、Eu 2 Te 3 、Gd 2 Te 3 、Tb 2 Te 3 、Dy 2 Te 3 、Ho 2 Te 3 、Er 2 Te 3 、Tm 2 Te 3 、Yb 2 Te 3 And Lu 2 Te 3 。
The alkali metal complex, alkaline earth metal complex, and rare earth metal complex may comprise i) one of the ions of the alkali metal, alkaline earth metal, and rare earth metal, and ii) a ligand bonded to the metal ion, such as hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
The electron injection layer may comprise (e.g., consist of) the following: the alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkaline earth metal-containing compound, rare earth metal-containing compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof as described above. In an embodiment, the electron injection layer may further include an organic material (e.g., a compound represented by formula 601).
In embodiments, the electron injection layer may include (e.g., consist of) the following: i) An alkali metal-containing compound (e.g., an alkali metal halide), ii) a) an alkali metal-containing compound (e.g., an alkali metal halide); and b) an alkali metal, alkaline earth metal, rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI: yb co-deposited layer, a RbI: yb co-deposited layer, a LiF: yb co-deposited layer, or the like.
When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in the matrix including the organic material.
The thickness of the electron injection layer may be aboutTo about->And e.g. about->To about->When the thickness of the electron injection layer is within the above-described range, suitable or satisfactory electron injection characteristics can be obtained without a significant increase in the driving voltage.
Second electrode 150
The second electrode 150 may be on the intermediate layer 130 having such a structure. The second electrode 150 may be a cathode as an electron injection electrode, and a metal, an alloy, a conductive compound, or any combination thereof each having a low work function may be used as a material for the second electrode 150.
In an embodiment, the second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a transflective electrode, or a reflective electrode.
The second electrode 150 may have a single-layer structure or a multi-layer structure including two or more layers.
Cover layer
The first cover layer may be external to the first electrode 110 and/or the second cover layer may be external to the second electrode 150. In more detail, the light emitting device 10 may have a structure in which the first cover layer, the first electrode 110, the intermediate layer 130, and the second electrode 150 are sequentially stacked in this prescribed order, a structure in which the first electrode 110, the intermediate layer 130, the second electrode 150, and the second cover layer are sequentially stacked in this prescribed order, or a structure in which the first cover layer, the first electrode 110, the intermediate layer 130, the second electrode 150, and the second cover layer are sequentially stacked in this prescribed order.
The light generated in the emission layer of the intermediate layer 130 of the light emitting device 10 may be extracted toward the outside through the first electrode 110 (which is a semi-reflective electrode or a transmissive electrode) and the first cover layer, or the light generated in the emission layer of the intermediate layer 130 of the light emitting device 10 may be extracted toward the outside through the second electrode 150 (which is a semi-reflective electrode or a transmissive electrode) and the second cover layer.
The first cover layer and the second cover layer may increase external light emitting efficiency according to principles of constructive interference. Accordingly, the light emitting efficiency of the light emitting device 10 is increased, so that the light emitting efficiency of the light emitting device 10 can be improved.
Each of the first and second cover layers may comprise a material having a refractive index (at a wavelength of 589 nm) of 1.6 or greater than 1.6.
The first cover layer and the second cover layer may each be independently an organic cover layer including an organic material, an inorganic cover layer including an inorganic material, or an organic-inorganic composite cover layer including an organic material and an inorganic material.
At least one of the first cover layer and the second cover layer may each independently comprise a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, heterocyclic compound, and amine group-containing compound may be optionally substituted with substituents containing O, N, S, se, si, F, cl, br, I or any combination thereof. In embodiments, at least one of the first cover layer and the second cover layer may each independently comprise an amine group-containing compound.
In an embodiment, at least one of the first cover layer and the second cover layer may each independently comprise a compound represented by formula 201, a compound represented by formula 202, or any combination thereof.
In embodiments, at least one of the first cover layer and the second cover layer may each independently comprise one of the compounds HT28 to HT33, one of the compounds CP1 to CP6, compound CP01, β -NPB, or a mixture thereof.
Film and method for producing the same
The organometallic compound represented by formula 1 may be contained in various suitable films. Thus, according to one or more embodiments, a film comprising the organometallic compound represented by formula 1 may be provided. The film may be, for example, an optical member (e.g., a light control mechanism) (e.g., a color filter, a color conversion member, a cover layer, a light extraction efficiency enhancement layer, a selective light absorption layer, a polarizing layer, and/or a layer containing sub-dots), a light blocking member (e.g., a light reflecting layer and/or a light absorption layer), a protective layer (e.g., an insulating layer and/or a dielectric layer).
Electronic equipment
The light emitting device may be included in a variety of suitable electronic devices. In an embodiment, the electronic device including the light emitting device may be a light emitting device, an authentication device, or the like.
In addition to the light emitting apparatus, the electronic device (e.g., light emitting device) may further include: i) A color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and/or the color conversion layer may be in at least one traveling direction of light emitted from the light emitting device. In an embodiment, the light emitted from the light emitting device may be blue light and/or white light. The light emitting device may be the same as described above. In embodiments, the color conversion layer may comprise quantum dots. The quantum dots may be, for example, quantum dots as described herein.
The electronic device may include a first substrate. The first substrate may include a plurality of sub-pixel regions, the color filter may include a plurality of color filter regions respectively corresponding to the sub-pixel regions, and the color conversion layer may include a plurality of color conversion regions respectively corresponding to the sub-pixel regions.
The pixel defining layer may be located between the sub-pixel regions to define each of the sub-pixel regions.
The color filter may further include a plurality of color filter regions and a light shielding pattern between the color filter regions, and the color conversion layer may include a plurality of color conversion regions and a light shielding pattern between the color conversion regions.
The color filter region (or the color conversion region) may include a first region that emits first color light, a second region that emits second color light, and/or a third region that emits third color light, and the first color light, the second color light, and/or the third color light may have maximum emission wavelengths different from each other. In an embodiment, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In an embodiment, the color filter region (or color conversion region) may comprise quantum dots. In more detail, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may include no quantum dots. The quantum dots may be the same as described in this specification. The first region, the second region, and/or the third region may each further comprise a diffuser (e.g., a light diffuser).
In an embodiment, the light emitting device may emit first light, the first region may absorb the first light to emit first color light, the second region may absorb the first light to emit second first color light, and the third region may absorb the first light to emit third first color light. In this regard, the first, second, and third first color lights may each have a different maximum emission wavelength. In more detail, the first light may be blue light, the first color light may be red light, the second first color light may be green light, and the third first color light may be blue light.
The electronic device may further include a Thin Film Transistor (TFT) in addition to the light emitting device as described above. The TFT may include a source electrode, a drain electrode, and an active layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of a first electrode and a second electrode of the light emitting device.
The TFT may further include a gate electrode, a gate insulating film, and the like.
The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, or the like.
The electronic apparatus may further include a sealing part for sealing the light emitting device. The sealing part may be located between the color filter and/or the color conversion layer and the light emitting device. The seal allows light from the light emitting device to be extracted to the outside while preventing or reducing, in parallel (e.g., simultaneously), ambient air and/or moisture from penetrating into the light emitting device. The sealing part may be a sealing substrate including a transparent glass substrate and/or a plastic substrate. The sealing portion may be a thin film encapsulation layer including at least one of an organic layer and/or an inorganic layer. When the seal is a thin film encapsulation layer, the electronic device may be flexible.
Depending on the intended use of the electronic device, various suitable functional layers may be additionally located on the sealing part in addition to the color filters and/or the color conversion layer. The functional layer may include a touch screen layer, a polarizing layer, and the like. The touch screen layer may be a pressure sensitive touch screen layer, a capacitive touch screen layer, and/or an infrared touch screen layer.
The authentication apparatus may further include a biometric information collector in addition to the light emitting device. The verification device may be a biometric verification device that verifies an individual, for example, by using biometric information (e.g., a fingertip, a pupil, etc.) of a living being.
The electronic device may be applied to various suitable displays, light sources, lighting, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic journals, electronic dictionaries, electronic game machines, medical instruments (e.g., electronic thermometers, blood pressure meters, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasonic diagnostic devices, and/or endoscope displays), fish probes, various suitable measuring instruments, meters (e.g., meters for vehicles, aircraft, and/or watercraft), projectors, and the like.
Description of fig. 2 and 3
Fig. 2 is a cross-sectional view of a light emitting device according to an embodiment.
The light emitting apparatus of fig. 2 includes a substrate 100, a Thin Film Transistor (TFT), a light emitting device, and a package part 300 sealing the light emitting device.
The substrate 100 may be a flexible substrate, a glass substrate, and/or a metal substrate. The buffer layer 210 may be formed on the substrate 100. The buffer layer 210 may prevent or reduce penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.
The TFT may be on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
The active layer 220 may include an inorganic semiconductor (e.g., silicon or polysilicon), an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be on the active layer 220, and the gate electrode 240 may be on the gate insulating film 230.
An interlayer insulating film 250 may be on the gate electrode 240. An interlayer insulating film 250 may be placed between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260, and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.
The source electrode 260 and the drain electrode 270 may be on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source and drain regions of the active layer 220, and the source and drain electrodes 260 and 270 may contact the exposed portions of the source and drain regions of the active layer 220.
The TFT is electrically connected to the light emitting device to drive the light emitting device, and may be covered by the passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. A light emitting device is provided on the passivation layer 280. The light emitting device may include a first electrode 110, an intermediate layer 130, and a second electrode 150.
The first electrode 110 may be on the passivation layer 280. The passivation layer 280 may not entirely cover the drain electrode 270 and may expose a portion of the drain electrode 270, and the first electrode 110 may be connected to the exposed portion of the drain electrode 270.
A pixel defining layer 290 containing an insulating material (e.g., an electrically insulating material) may be on the first electrode 110. The pixel defining layer 290 exposes a region of the first electrode 110, and the intermediate layer 130 may be in the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide and/or a polyacrylic acid organic film. In some embodiments, at least some of the layers of the intermediate layer 130 may extend beyond the upper portion of the pixel defining layer 290 in the form of a common layer.
The second electrode 150 may be on the intermediate layer 130, and the capping layer 170 may be additionally on the second electrode 150. The cover layer 170 may cover the second electrode 150.
The encapsulation 300 may be on the cover layer 170. The encapsulation 300 may be on the light emitting device to protect the light emitting device from moisture and/or oxygen. The encapsulation part 300 may include: an inorganic film, said inorganic film coatingSilicon-containing nitride (SiN) x ) Silicon oxide (SiO) x ) Indium tin oxide, indium zinc oxide, or any combination thereof; an organic film comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic-based resins (e.g., polymethyl methacrylate, polyacrylic acid, etc.), epoxy-based resins (e.g., aliphatic Glycidyl Ethers (AGEs), etc.), or any combination thereof; or a combination of inorganic and organic films.
Fig. 3 is a cross-sectional view of a light emitting device according to an embodiment.
The light emitting device of fig. 3 is the same as that of fig. 2, but the light shielding pattern 500 and the functional region 400 are additionally on the encapsulation 300. The functional area 400 may be i) a color filter area, ii) a color conversion area, or iii) a combination of a color filter area and a color conversion area. In an embodiment, the light emitting device included in the light emitting apparatus of fig. 3 may be a tandem light emitting device.
Description of FIG. 4
Fig. 4 is a schematic perspective view of an electronic device 1 including a light emitting device according to an embodiment. The electronic apparatus 1 may be a device displaying a moving image or a still image, and may be a portable electronic apparatus such as a mobile phone, a smart phone, a tablet Personal Computer (PC), a mobile communication terminal, an electronic diary, an electronic book, a Portable Multimedia Player (PMP), a navigation system, or an Ultra Mobile PC (UMPC), and various suitable products such as a television, a laptop, a monitor, a signboard, an internet of things (IOT) apparatus; or a component thereof. Furthermore, the electronic device 1 may be a wearable device, such as a smart watch, a watch phone, a glasses type display or a Head Mounted Display (HMD), or a component thereof. However, the present disclosure is not limited thereto. In an embodiment, the electronic device 1 may be an instrument panel of a vehicle, a Central Information Display (CID) on a central panel or instrument panel of a vehicle, an indoor mirror display replacing a side view mirror of a vehicle, an entertainment device of a rear seat of a vehicle or a display on a back surface of a front seat of a vehicle, a head-up display (HUD) mounted in front of a vehicle or projected on a front window glass, or a computer generated holographic augmented reality head-up display (CGH AR HUD). For ease of explanation, fig. 4 shows a case in which the electronic apparatus 1 is a smart phone.
The electronic apparatus 1 may include a display area DA and a non-display area NDA outside the display area DA. The electronic apparatus 1 may realize an image by an array of a plurality of pixels two-dimensionally arranged in the display area DA.
The non-display area NDA may be an area where no image is displayed, and may completely surround the display area DA. A driver for supplying an electric signal or power to the display area DA or the like in the electronic apparatus 1 may be in the non-display area NDA. A pad, which is a region to which an electronic device or a printed circuit board may be electrically connected, may be in the non-display region NDA.
The electronic device 1 may have different lengths in the x-axis direction and the y-axis direction. For example, as shown in fig. 4, the length in the x-axis direction may be smaller than the length in the y-axis direction. As another example, the length in the x-axis direction and the length in the y-axis direction may be the same as each other. As another example, the length in the x-axis direction may be greater than the length in the y-axis direction.
Description of FIGS. 5 and 6A-6C
Fig. 5 is a schematic view of the outside of a vehicle 1000 as an electronic device including a light emitting device according to an embodiment. Fig. 6A-6C are schematic diagrams of an interior of a vehicle 1000 according to various embodiments.
Referring to fig. 5, 6A, 6B, and 6C, a vehicle 1000 may refer to various suitable devices that move an object to be transported, such as a person, an object, and/or an animal, from a departure point to a destination. Vehicle 1000 may include a vehicle traveling on a road and/or track, a boat moving on the sea and/or river, and an aircraft flying in the air (e.g., using the action of air).
The vehicle 1000 may travel on a roadway and/or track. The vehicle 1000 may move in a set or predetermined direction based on rotation of at least one wheel. For example, the vehicle 1000 may include a three or four wheeled vehicle, a construction vehicle, a two wheeled vehicle, a prime mover device, a bicycle, and a train traveling on a track.
The vehicle 1000 may include a main body having an interior trim and an exterior trim, and a chassis in which mechanical equipment for driving is mounted as other components than the main body. The exterior trim of the main body may include pillars disposed at boundaries between the front panel, hood, top panel, rear panel, trunk, and door. The chassis of the vehicle 1000 may include power generation devices, power transmission devices, driving devices, steering devices, braking devices, suspension devices, transmission devices, fueling devices, and front wheels, rear wheels, left wheels, and right wheels.
The vehicle 1000 may include side window glass 1100, front window glass 1200, side mirror 1300, cluster 1400, center panel 1500, front passenger seat dashboard 1600, and display device 2.
Side window pane 1100 and front window pane 1200 may be separated by a pillar between side window pane 1100 and front window pane 1200.
Side window glass 1100 may be mounted on a side of vehicle 1000. In an embodiment, side window glass 1100 may be mounted on a door of vehicle 1000. The side window glass 1100 may include a plurality of side window glasses 1100 that may face each other. In embodiments, side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In an embodiment, the first side glazing 1110 may be adjacent to the cluster member 1400. The second side glass 1120 may be adjacent to the front passenger seat dashboard 1600.
In embodiments, side panes 1100 may be spaced apart from one another in the x-direction or in the-x direction. For example, the first side window pane 1110 and the second side window pane 1120 may be spaced apart from each other in the x-direction or in the-x-direction. In other words, the virtual straight line L connecting the side panes 1100 to each other may extend in the x-direction or in the-x-direction. For example, a virtual straight line L connecting the first side window glass 1110 to the second side window glass 1120 may extend in the x-direction or in the-x-direction.
The front glass 1200 may be mounted in front of the vehicle 1000. Front pane 1200 may be between side panes 1100 that face each other.
The side view mirror 1300 may provide a rear view of the vehicle 1000. The side view mirror 1300 may be mounted on an external decoration of the main body. In an embodiment, the side-view mirror 1300 may include a plurality of side-view mirrors 1300. One of the plurality of side view mirrors 1300 may be external to the first side window pane 1110. Another of the plurality of side view mirrors 1300 may be external to the second side window pane 1120.
The cluster 1400 may be in front of the steering wheel. Cluster member 1400 may include a tachometer, speedometer, coolant thermometer, fuel gauge, turn signal indicator light, high beam indicator light, warning light, seat belt warning light, odometer, automatic transmission selector lever indicator light, door opening warning light, engine oil warning light, and/or low fuel warning light.
The center panel 1500 may include a control panel on which buttons for adjusting audio devices, air conditioning devices, and/or seat heaters are arranged. The center panel 1500 may be on one side of the cluster 1400.
The front passenger seat dashboard 1600 may be spaced apart from the cluster 1400 with the center panel 1500 therebetween. In an embodiment, the cluster 1400 may correspond to a driver seat and the front passenger seat dashboard 1600 may correspond to a front passenger seat. In an embodiment, the cluster 1400 may be adjacent to a first side window glass 1110 and the front passenger seat dashboard 1600 may be adjacent to a second side window glass 1120.
In an embodiment, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be inside the vehicle 1000. In an embodiment, the display device 2 may be between side panes 1100 facing each other. The display device 2 may be on at least one of the cluster 1400, the center panel 1500, and the front passenger seat dashboard 1600.
The display device 2 may include an organic light emitting display, an inorganic electro-luminescence (EL) light emitting display (inorganic light emitting display), and a quantum dot display. Hereinafter, an organic light emitting display including the light emitting device according to the embodiment is described as an example of the display apparatus 2 according to the embodiment, but in the embodiment of the present disclosure, various suitable types (or kinds) of display apparatuses as described above may be used.
Referring to fig. 6A, the display device 2 may be on a center panel 1500. In an embodiment, the display device 2 may display navigation information. In an embodiment, the display device 2 may display information about audio, video and/or vehicle settings.
Referring to fig. 6B, the display device 2 may be on a cluster 1400. In this case, the cluster 1400 may display driving information or the like through the display device 2. In other words, cluster 1400 may be implemented digitally. The digital cluster 1400 may display the vehicle information and the driving information as images. For example, tachometer pins, gauges, and/or various suitable warning light icons may be displayed by digital signals.
Referring to fig. 6C, the display device 2 may be on the front passenger seat dashboard 1600. The display device 2 may be embedded in the front passenger seat dashboard 1600 or may be on the front passenger seat dashboard 1600. In an embodiment, the display device 2 on the front passenger seat dashboard 1600 may display images related to information displayed on the cluster 1400 and/or information displayed on the center panel 1500. In an embodiment, the display device 2 on the front passenger seat dashboard 1600 may display different information than the information displayed on the cluster 1400 and/or the information displayed on the center panel 1500.
Method of manufacture
The layers included in the hole transport region, the emission layer, and the layers included in the electron transport region may be formed in the specific region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser induced thermal imaging.
When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, a deposition temperature of about 100 ℃ to about 500 ℃, about 10 ℃, depending on the material to be contained in the layer to be formed and the structure of the layer to be formed, may be used -8 To about 10 -3 Vacuum level of the tray and the likePer second to about->Deposition was performed at a deposition rate of/sec.
Definition of terms
The term "C" as used herein 3 -C 60 A carbocyclic group "refers to a cyclic group consisting of only carbon as the ring forming atom and having from three to sixty carbon atoms (e.g., from 3 to 30, from 3 to 20, from 3 to 15, or from 3 to 10 carbon atoms), and the term" C "as used herein 1 -C 60 A heterocyclic group "means a cyclic group having one to sixty carbon atoms (e.g., 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms) and further having a heteroatom other than carbon as a ring-forming atom. C (C) 3 -C 60 Carbocycle group and C 1 -C 60 The heterocyclic groups may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed with each other. In embodiments, C 1 -C 60 The heterocyclic group has 3 to 61 ring atoms (e.g., 3 to 30, 3 to 20, 3 to 15, or 3 to 10 ring atoms).
The term "cyclic group" as used herein may include C 3 -C 60 Carbocycle group and C 1 -C 60 A heterocyclic group.
The term "pi-electron rich C" as used herein 3 -C 60 A cyclic group "refers to a cyclic group having three to sixty carbon atoms (e.g., 3 to 30, 3 to 20, 3 to 15, or 3 to 10 carbon atoms) and does not contain-n=' as a ring-forming moiety, and as used herein the term" pi electron deficient nitrogen-containing C 1 -C 60 A cyclic group "refers to a heterocyclic group having one to sixty carbon atoms (e.g., 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms) and containing = -N =' as a ring forming moietyA bolus.
In the context of an embodiment of the present invention,
C 3 -C 60 the carbocyclic group may be i) a group T1, or ii) a condensed cyclic group in which two or more groups T1 are condensed with each other (e.g., a cyclopentadienyl group, an adamantyl group, a norbornane group, a phenyl group, a pentylene group, a naphthalene group, a azulene group, an indacene group, an acenaphthylene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a benzophenanthrene group, a pyrene group, a pentylene group, a naphthalene group, a azulene group, an indacene group, a acenaphthylene group, a phenalene group, a phenanthrene group, a benzophenanthrene group, a pyrene group, a triphenylene group, a,A group, a perylene group, a pentacene group, a heptylene group, a tetracene group, a picene group, a hexa-phenyl group, a pentacene group, a yu red province group, a coronene group, an egg-phenyl group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, an indeno phenanthrene group, or an indeno anthracene group),
C 1 -C 60 the heterocyclic group may be i) a group T2, ii) a condensed cyclic group in which two or more groups T2 are condensed with each other, or iii) a condensed cyclic group in which at least one group T2 and at least one group T1 are condensed with each other (for example, pyrrole groups, thiophene groups, furan groups, indole groups, benzindole groups, naphtalindole groups, isoindole groups, benzisoindole groups, naphtalindole groups, benzosilole groups, benzothiophene groups, benzofurans groups, carbazole groups, dibenzosilole groups, dibenzothiophene groups, dibenzofuran groups, indenocarbazole groups, indolocarbazole groups, benzocarbazole groups, benzothiocarbazole groups, benzoindolocarbazole groups, benzocarbazole groups, benzonaphtalenofuran groups, benzonaphtalenothiofuran groups, benzonaphtalene silole groups, benzodibenzofuran groups, benzodibenzothiophene groups, benzothiophene groups, pyrazole groups, imidazole groups, triazole groups, oxazole groups, isoxazole groups, oxadiazole groups, thiazole groups, isothiazole groups, dithiazole groups, benzopyrazole groups, and benzoxazole groups A group, a benzimidazole group, a benzoxazole group, a benzisoxazole group, a benzothiazole group, a benzisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzothiophene group, an azadibenzofuran group, and the like,
pi electron rich C 3 -C 60 The cyclic group may be i) a group T1, ii) a condensed cyclic group in which two or more groups T1 are condensed with each other, iii) a group T3, iv) a condensed cyclic group in which two or more groups T3 are condensed with each other, or v) a condensed cyclic group in which at least one group T3 and at least one group T1 are condensed with each other (e.g., C 3 -C 60 Carbocycle groups, 1H-pyrrole groups, silole groups, borole-dienyl groups, 2H-pyrrole groups, 3H-pyrrole groups, thiophene groups, furan groups, indole groups, benzoindole groups, naphtalindole groups, isoindole groups, benzisoindole groups, naphtalisoindole groups, benzothiophene groups, benzofuran groups, carbazole groups, dibenzosilole groups, dibenzothiophene groups, dibenzofuran groups, indenocarbazole groups, indolocarbazole groups, benzocarbazole groups, benzothiophene carbazole groups, benzobenzoxazole groups, benzoindole carbazole groups, benzocarbazole groups, benzonaphtalene furan groups, benzonaphtalene thiophene groups, benzonaphtalothiophene groups, benzonaphtalozole groups, benzodibenzo-dibenzofuran groups, benzodibenzothiophene groups, benzobenzothiophene groups, and the like), and the like
Pi electron deficient nitrogen containing C 1 -C 60 The cyclic groups may be i) groups T4, ii) two of themOr more than two fused cyclic groups in which the groups T4 are fused to each other, iii) fused cyclic groups in which at least one group T4 and at least one group T1 are fused to each other, iv) fused cyclic groups in which at least one group T4 and at least one group T3 are fused to each other, or v) fused cyclic groups in which at least one group T4, at least one group T1 and at least one group T3 are fused to each other (for example, pyrazole groups, imidazole groups, triazole groups, oxazole groups, isoxazole groups, oxadiazole groups, thiazole groups, isothiazole groups, thiadiazole groups, benzopyrazole groups, benzimidazole groups, benzoxazole groups, benzisoxazole groups, benzothiazole groups, benzisothiazole groups, pyridine groups, pyrimidine groups, pyrazine groups, pyridazine groups, triazine groups, quinoline groups, isoquinoline groups, benzoquinoline groups, benzisoquinoline groups, quinoxaline groups, benzoquinoxaline groups, quinazoline groups, benzoquinazoline groups, phenanthroline groups, cinnoline groups, phthalazine groups, naphthyridine groups, imidazopyridine groups, imidazopyrimidine groups, imidazotriazine groups, imidazopyrazine groups, imidazopyridazine groups, azafluorene groups, azadibenzothiophene groups, etc.,
Wherein the group T1 may be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadienyl group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or bicyclo [2.2.1] heptane) group, a norbornene group, a bicyclo [1.1.1] pentane group, a bicyclo [2.1.1] hexane group, a bicyclo [2.2.2] octane group or a phenyl group,
the group T2 may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, a boronpentadienyl group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaboronpentadiene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidinyl group, an imidazolidine group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a tetrahydropyrimidine group, or a dihydropyridazine group,
The group T3 may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group or a borole group, and
the group T4 may be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group or a tetrazine group.
The terms "cyclic group", "C", as used herein 3 -C 60 Carbocycle group "," C 1 -C 60 Heterocyclic group "," pi-electron rich C 3 -C 60 The cyclic group "or" pi electron deficient nitrogen-containing C 1 -C 60 A cyclic group "refers to a group, monovalent group, or multivalent group (e.g., divalent group, trivalent group, tetravalent group, etc.), fused to any suitable cyclic group, depending on the structure of the formula associated with the use of the term. In embodiments, the "phenyl group" may be a benzo group, a phenyl group, a phenylene group, etc., which may be readily understood by one of ordinary skill in the art according to structures of the formula including "phenyl group".
In some embodiments, monovalent C 3 -C 60 Carbocyclic group and monovalent C 1 -C 60 Examples of heterocyclic groups may include C 3 -C 10 Cycloalkyl radicals, C 1 -C 10 A heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl radical, C 6 -C 60 Aryl group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups and monovalent non-aromatic fused heteropolycyclic groups, and divalent C 3 -C 60 Carbocycle group and divalent C 1 -C 60 Examples of heterocyclic groups may include C 3 -C 10 Cycloalkylene group, C 1 -C 10 A heterocycloalkylene group, C 3 -C 10 Cycloalkenyl radical, C 1 -C 10 Heterocyclylene radicals, C 6 -C 60 Arylene group, C 1 -C 60 Heteroarylene groups, divalent non-aromatic fused polycyclic groups, and divalent non-aromatic fused heteropolycyclic groups.
The term "C" as used herein 1 -C 60 Alkyl group "means a straight or branched aliphatic monovalent group having one to sixty carbon atoms (e.g., 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms), and examples thereof include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, a n-heptyl group, an isoheptyl group, a Zhong Geng group, a tert-heptyl group, a n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, a n-nonyl group, an isononyl group, a Zhong Ren group, a tert-nonyl group, a n-decyl group, an isodecyl group, a Zhong Guiji group, and a tert-decyl group. The term "C" as used herein 1 -C 60 An alkylene group "means having a group corresponding to C 1 -C 60 Divalent groups of substantially identical structure for the alkyl groups.
The term "C" as used herein 2 -C 60 Alkenyl group "means at C 2 -C 60 A monovalent hydrocarbon group having at least one carbon-carbon double bond at the main chain (e.g., in the middle) or at the terminal (e.g., at the end) of an alkyl group, and examples thereof include vinyl groups, acryl groups, and butenyl groups. The term "C" as used herein 2 -C 60 Alkenylene group "means having a meaning with C 2 -C 60 Divalent groups of substantially identical structure to the alkenyl groups.
The term "C" as used herein 2 -C 60 Alkynyl group "means at C 2 -C 60 A monovalent hydrocarbon group having at least one carbon-carbon triple bond at the main chain (e.g., in the middle) or at the terminal (e.g., at the end) of the alkyl group, and examples thereof include an ethynyl group and a propynyl group. The term "C" as used herein 2 -C 60 Alkynyl group "means having a meaning with C 2 -C 60 Divalent groups of substantially identical structure to the alkynyl groups.
The term "C" as used herein 1 -C 60 Alkoxy group "means a group consisting of-OA 101 (wherein A 101 Is C 1 -C 60 Alkyl group), and examples thereof include methoxy group, ethoxy group, and isopropoxy group.
The term "C" as used herein 3 -C 10 Cycloalkyl group "means a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group (or bicyclo [2.2.1]Heptyl group), bicyclo [1.1.1]Pentyl group, bicyclo [2.1.1]Hexyl radical and bicyclo [2.2.2]Octyl groups. The term "C" as used herein 3 -C 10 The term "cycloalkylene group" means having a group attached to C 3 -C 10 Cycloalkyl groups are essentially identical in structure.
The term "C" as used herein 1 -C 10 The heterocycloalkyl group "means a monovalent cyclic group further containing at least one heteroatom other than carbon atom as a ring-forming atom and having 1 to 10 carbon atoms, and examples thereof include a 1,2,3, 4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothienyl group. The term "C" as used herein 1 -C 10 Heterocyclylene group "means havingWith C and 1 -C 10 divalent groups of substantially identical structure for the heterocycloalkyl group.
The term C as used herein 3 -C 10 Cycloalkenyl group refers to a monovalent cyclic group having three to ten carbon atoms and at least one carbon-carbon double bond in its ring and no aromaticity (e.g., not aromatic), and examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term "C" as used herein 3 -C 10 The cycloalkenylene group "means having a ring structure with C 3 -C 10 Bivalent groups of substantially identical structure to cycloalkenyl groups.
The term "C" as used herein 1 -C 10 A heterocycloalkenyl group "refers to a monovalent cyclic group having, as ring-forming atoms, at least one heteroatom other than carbon atoms, 1 to 10 carbon atoms, and at least one double bond in its cyclic structure. C (C) 1 -C 10 Examples of heterocycloalkenyl groups include 4, 5-dihydro-1, 2,3, 4-oxazolyl groups, 2, 3-dihydrofuranyl groups, and 2, 3-dihydrothienyl groups. The term "C" as used herein 1 -C 10 Heterocyclylene group "means having a group corresponding to C 1 -C 10 Divalent radicals of substantially identical structure to the cycloalkenyl radicals.
The term "C" as used herein 6 -C 60 Aryl group "refers to a monovalent group having a carbocyclic aromatic system of six to sixty carbon atoms (e.g., 6 to 30, 6 to 20, 6 to 15, or 6 to 10 carbon atoms), and the term" C "as used herein 6 -C 60 Arylene group "refers to a divalent group having a carbocyclic aromatic system of six to sixty carbon atoms (e.g., 6 to 30, 6 to 20, 6 to 15, or 6 to 10 carbon atoms). C (C) 6 -C 60 Examples of aryl groups include phenyl groups, pentylene groups, naphthyl groups, azulenyl groups, indacenyl groups, acenaphthenyl groups, phenalkenyl groups, phenanthryl groups, anthryl groups, fluoranthenyl groups, benzophenanthryl groups, pyrenyl groups, A phenyl group, a perylene group, a pentacenyl group, a heptenyl group, a tetracenyl group, a picenyl group, a hexaphenyl group, a pentacenyl group, a yuzuo group, a coroneyl group, and an egg phenyl group. When C 6 -C 60 Aryl group and C 6 -C 60 When the arylene groups each comprise two or more rings, the rings may be fused to each other.
The term "C" as used herein 1 -C 60 Heteroaryl group "refers to a monovalent group having a heterocyclic aromatic system containing at least one heteroatom other than carbon atoms and 1 to 60 carbon atoms (e.g., 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms) as ring-forming atoms. The term "C" as used herein 1 -C 60 Heteroaryl ene group "refers to a divalent group having a heterocyclic aromatic system containing at least one heteroatom other than carbon atoms and 1 to 60 carbon atoms (e.g., 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms) as ring-forming atoms. C (C) 1 -C 60 Examples of heteroaryl groups include pyridinyl groups, pyrimidinyl groups, pyrazinyl groups, pyridazinyl groups, triazinyl groups, quinolinyl groups, benzoquinolinyl groups, isoquinolinyl groups, benzoisoquinolinyl groups, quinoxalinyl groups, benzoquinoxalinyl groups, quinazolinyl groups, benzoquinazolinyl groups, cinnolinyl groups, phenanthrolinyl groups, phthalazinyl groups, and naphthyridinyl groups. When C 1 -C 60 Heteroaryl groups and C 1 -C 60 When the heteroarylene groups each contain two or more rings, the rings may be fused to each other.
The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group having two or more rings fused to each other, having only carbon atoms (e.g., having 8 to 60 carbon atoms, e.g., 8 to 30, 8 to 20, 8 to 15, or 8 to 10 carbon atoms) as ring-forming atoms, and having no aromaticity in its molecular structure when considered as a whole (e.g., not aromatic when considered as a whole). Examples of monovalent non-aromatic fused polycyclic groups include indenyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, indenofenyl groups, and indenoanthrenyl groups. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having substantially the same structure as a monovalent non-aromatic fused polycyclic group.
The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group having two or more rings fused to each other, at least one heteroatom other than carbon atoms (e.g., having 1 to 60 carbon atoms, e.g., 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms) as a ring-forming atom, and having no aromaticity in its molecular structure when considered as a whole (e.g., not aromatic when considered as a whole). Examples of monovalent non-aromatic fused heteropolycyclic groups include pyrrolyl groups, thienyl groups, furanyl groups, indolyl groups, benzindolyl groups, naphthyridinyl groups, isoindolyl groups, benzisoindolyl groups, naphthyridinyl groups, benzothienyl groups, benzofuranyl groups, carbazolyl groups, dibenzosilol groups, dibenzothienyl groups, dibenzofuranyl groups, azacarbazolyl groups, azafluorenyl groups, azadibenzosilol groups, azadibenzothienyl groups, azadibenzofuranyl groups, pyrazolyl groups, imidazolyl groups, triazolyl groups, tetrazolyl groups, oxazolyl groups, isoxazolyl groups, thiazolyl groups, isothiazolyl groups, oxadiazolyl groups, and combinations thereof thiadiazolyl group, benzopyrazolyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, benzoxadiazolyl group, benzothiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, imidazotriazinyl group, imidazopyrazinyl group, imidazopyridazinyl group, indenocarbazolyl group, indolocarbazolyl group, benzofuranocarbazolyl group, benzothiocarbazolyl group, benzoindolocarbazolyl group, benzocarbazolyl group, benzonaphtofuranyl group, benzonaphtaphthenyl group, benzonaphtaphthoyl group, benzodibenzofuranyl group, benzodibenzothiophenyl group, and benzothiaphthoyl group. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having substantially the same structure as a monovalent non-aromatic fused heteropolycyclic group.
The term "C" as used herein 6 -C 60 Aryloxy group "means-OA 102 (wherein A 102 Is C 6 -C 60 Aryl group), and the term "C" as used herein 6 -C 60 Arylthio group "means-SA 103 (wherein A 103 Is C 6 -C 60 Aryl groups).
The term "C" as used herein 7 -C 60 Arylalkyl group "means-A 104 A 105 (wherein A 104 May be C 1 -C 54 An alkylene group, and A 105 May be C 6 -C 59 Aryl group), and the term "C" as used herein 2 -C 60 Heteroarylalkyl group "means-A 106 A 107 (wherein A 106 May be C 1 -C 59 An alkylene group, and A 107 May be C 1 -C 59 Heteroaryl groups).
The term "R" as used herein 10a "means:
deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group or a nitro group;
each unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocycle group, C 1 -C 60 Heterocyclic groups, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio groups, C 7 -C 60 Arylalkyl radicals, C 2 -C 60 Heteroarylalkyl group, -Si (Q) 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(＝O)(Q 11 )、-S(＝O) 2 (Q 11 )、-P(＝O)(Q 11 )(Q 12 ) Or any combination thereof 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups or C 1 -C 60 An alkoxy group;
each unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl radicals, C 1 -C 60 Alkoxy groups, C 3 -C 60 Carbocycle group, C 1 -C 60 Heterocyclic groups, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio groups, C 7 -C 60 Arylalkyl radicals, C 2 -C 60 Heteroarylalkyl group, -Si (Q) 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(＝O)(Q 21 )、-S(＝O) 2 (Q 21 )、-P(＝O)(Q 21 )(Q 22 ) Or any combination thereof 3 -C 60 Carbocycle group, C 1 -C 60 Heterocyclic groups, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio groups, C 7 -C 60 Arylalkyl radicals or C 2 -C 60 A heteroarylalkyl group; or alternatively
-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 ) or-P (=O) (Q 31 )(Q 32 )。
Q 1 To Q 3 、Q 11 To Q 13 、Q 21 To Q 23 Q and 31 to Q 33 Each may independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group;a cyano group; a nitro group; or each unsubstituted or deuterium, -F, cyano, C 1 -C 60 Alkyl group, C 1 -C 60 C substituted with an alkoxy group, a phenyl group, a biphenyl group, or any combination thereof 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl radicals, C 1 -C 60 Alkoxy groups, C 3 -C 60 Carbocycle group, C 1 -C 60 Heterocyclic groups, C 7 -C 60 Arylalkyl radicals or C 2 -C 60 A heteroarylalkyl group.
The term "heteroatom" as used herein refers to any atom other than a carbon atom, and the number of heteroatoms may be 1 to 10, for example, 1, 2, 3, 4, or 5. Examples of heteroatoms include O, S, N, P, si, B, ge, se or any combination thereof.
The term "third row transition metal" as used herein includes hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and the like.
The term "Ph" as used herein refers to a phenyl group, the term "Me" as used herein refers to a methyl group, the term "Et" as used herein refers to an ethyl group, the term "tert-Bu" or "Bu" as used herein t "refers to a tertiary butyl group, and the term" OMe "as used herein refers to an oxy group.
The term "biphenyl group" as used herein refers to a phenyl group substituted with a phenyl group. In other words, a "biphenyl group" is a group having C 6 -C 60 Substituted phenyl groups with aryl groups as substituents.
The term "terphenyl group" as used herein refers to a phenyl group substituted with a biphenyl group. In other words, a "terphenyl group" is a group having a substituent C 6 -C 60 Aryl group substituted C 6 -C 60 Substituted phenyl groups with aryl groups as substituents.
The x-axis, y-axis, and z-axis as used herein are not limited to three axes on a rectangular coordinate system, and may be interpreted in a broader sense including these three axes. For example, the x-axis, y-axis, and z-axis may be orthogonal to each other, but may refer to different directions that are not orthogonal to each other.
As used herein, unless otherwise defined, each refers to a binding site to an adjacent atom in the corresponding formula or moiety.
Hereinafter, the compound according to the embodiment and the light emitting device according to the embodiment will be described in more detail with reference to the following synthesis examples and examples. The expression "using B instead of a" used to describe the synthesis examples means using equimolar equivalents of B instead of a.
Examples
Synthesis example 1: synthesis of Compound 1
Synthesis of intermediate 1-1
Pd (PPh) 3 ) 4 (693 mg,0.60 mmol), 4-Acetylphenylboronic acid (2.95 g,18 mmol) and Na 2 CO 3 A saturated aqueous solution (36 ml) was added to a stirred solution of 1-bromo-4-methylnaphthalen-2-amine (2.83 g,12 mmol) in DMAc (72 ml), and the resulting mixture was refluxed overnight. Next, the reaction mixture was cooled to room temperature and distributed between EtOAc and brine. The organic layer was collected with Na 2 SO 4 Drying, filtration and concentration in vacuo to give a residue, which was then purified by flash column chromatography to give intermediate 1-1 (2.51 g, 76%).
Synthesis of intermediate 1-2
Intermediate 1-1 (2.2 g,8.0 mmol) and 1, 2-diphenyldiselenide (2.5 g,8.0 mmol) were placed in a flask and a nitrogen atmosphere was introduced. MeCN (40 ml) was added thereto via syringe, and then L-ascorbic acid (704 mg,4.0 mmol) dissolved in DMSO (4 ml) was added thereto. The resulting mixture was stirred for 1 minute, and then t-BuONO (t-butyl nitrite) (1.2 g,12 mmol) was added thereto. After stirring at 20 ℃ for 6 hours, the solvent was removed at low pressure, and the residue was purified by column chromatography to obtain intermediate 1-2 (2.36 g, 71%).
Synthesis of intermediates 1-3
Pd (OAc) was taken up under nitrogen 2 (167 mg,1.35 mmol), intermediate 1-2 (2.08 g,5.0 mmol), 2, 6-dimethylbenzoic acid (321 mg,2.25 mmol) and toluene (17 ml) were placed in a vial. The vials were then sealed and heated at 130 ℃ for 18 hours. The resulting mixture was cooled to room temperature and filtered through silica gel while eluting with EtOAc. The eluent was evaporated and the residue was purified by flash column chromatography (hexane) to obtain intermediate 1-3 (1.53 g, 91%).
Synthesis of intermediates 1-4
Saturated NaOH ethanol (C) 2 H 5 OH) solution was added to a mixture of 3-aminopyridine formaldehyde (562 mg,4.6 mmol) and intermediates 1-3 (1.53 g,4.6 mmol) in absolute ethanol, and the mixture was refluxed overnight. After cooling the mixture, the precipitate was collected by filtration and taken from CH 2 Cl 2 Recrystallization from the solution afforded intermediate 1-4 (1.26 g, 65%).
Synthesis of Compound 1
In a 50ml round bottom flask, intermediate 1-4 (3.0 mmol) was dissolved in 2-ethoxyethanol (12 ml). IrCl is added to 3 ·3H 2 O (1.35 mmol) and water (4 ml) were added to the flask. The resulting mixture was stirred under nitrogen at 120 ℃ for 24 hours and cooled to room temperature. The precipitate formed in the mixture was collected, washed with methanol and hexane, and dried in vacuo to obtain Ir (III) chloro-bridged dimer. Ir (III) chlorine bridged dimer, acetylacetone (2.03 mmol) and Na 2 O 3 (4.06 mmol) and 2-ethoxyethanol (13.5 ml) were mixed together and the resulting mixture was heated at 100℃for 6 hours. After cooling to room temperature, the precipitated solid was collected by filtration and washed with ethanol and hexane. The residue was dissolved in dichloromethane and the solid was filtered. The solution was concentrated in vacuo, and the residue was purified on a silica gel column and recrystallized to obtain compound 1 (18%).
Synthesis example 2: synthesis of Compound 3
Synthesis of intermediate 3-1
Pd (PPh) 3 ) 4 (693 mg,0.60 mmol), 4-Acetylphenylboronic acid (2.95 g,18 mmol) and Na 2 CO 3 A saturated aqueous solution (36 ml) was added to a stirred solution of 1-bromonaphthalen-2-ol (2.68 g,12 mmol) in DMAc (72 ml), and the resulting mixture was refluxed overnight. Next, the reaction mixture was cooled to room temperature and partitioned between EtOAc and brine. The organic layer was collected with Na 2 SO 4 Drying, filtration and concentration in vacuo to obtain a residue, which was then purified by column chromatography to obtain intermediate 3-1 (2.75 g, 83%).
Synthesis of intermediate 3-2
Intermediate 3-1 (2.75 g,10.0 mmol), pd (OAc) 2 (0.12 g,0.5 mmol), IPr (1, 3-bis (2, 6-diisopropylphenyl) imidazol-2-ylidene) (0.39 g,1.0 mmol), 4, 5-diazafluoren-9-one (0.19 g,1.0 mmol), sodium 2,4, 6-trimethylbenzoate (0.93 g,5.0 mmol), K 2 CO 3 (2.75 g,20.0 mmol), MS 3A (10 g) and mesitylene (50 ml) were added to the vial in the stated order. The resulting mixture was stirred at room temperature for 1 minute, and then stirred at a temperature of 120 ℃ for 24 hours. The mixture was filtered, washed with 250ml of EtOAc and concentrated in vacuo to give a residue, which was then purified by flash column chromatography to give intermediate 3-2 (1.95 g, 71%).
Synthesis of intermediate 3-3
Saturated NaOH ethanol (C) 2 H 5 OH) solution was added to a mixture of 2-amino-5- (tert-butyl) nicotinoyl fluoride (1.39 g,7.1 mmol) and intermediate 3-2 (1.95 g,7.1 mmol) in absolute ethanol, and the mixture was refluxed overnight. After cooling the mixture, the precipitate was collected by filtration and taken from CH 2 Cl 2 Recrystallization from the solution afforded intermediate 3-3 (2.03 g, 68%).
Synthesis of Compound 3
Intermediate 3-3 (2.03 g,4.8 mmol) was dissolved in 2-ethoxyethanol (19 ml) in a 50ml round bottom flask. IrCl is added to 3 ·3H 2 O (2.15 mmol) and water (6.4 ml) were added to the flask. The resulting mixture was stirred under nitrogen at 120 ℃ for 24 hours and cooled to room temperature. The precipitate formed in the mixture was collected, washed with methanol and hexane, and dried in vacuo to obtain Ir (III) chloro-bridged dimer. Ir (III) chlorine bridged dimer, acetylacetone (3.2 mmol) and Na 2 O 3 (6.5 mmol) and 2-ethoxyethanol (21.6 ml) were mixed together and the resulting mixture was heated at 100℃for 6 hours. After cooling to room temperature, byThe precipitated solid was collected by filtration and washed with ethanol and hexane. The residue was dissolved in dichloromethane and the solid was filtered. The solution was concentrated in vacuo, and the residue was purified on a silica gel column and recrystallized to obtain compound 3 (16%).
Synthesis example 3: synthesis of Compound 4
Synthesis of intermediate 4-1
Pd (PPh) 3 ) 4 (693 mg,0.60 mmol), 4-Acetylphenylboronic acid (2.95 g,18 mmol) and Na 2 CO 3 A saturated aqueous solution (36 ml) was added to a stirred solution of (2-bromophenyl) phenyl sulfide (3.18 g,12 mmol) in DMAc (72 ml), and the resulting mixture was refluxed overnight. Next, the reaction mixture was cooled to room temperature and partitioned between EtOAc and brine. The organic layer was collected with Na 2 SO 4 Drying, filtration and concentration in vacuo to obtain a residue, which was then purified by column chromatography to obtain intermediate 4-1 (2.97 g, 81%) as a white solid.
Synthesis of intermediate 4-2
Pd (OAc) was taken up under nitrogen 2 (300 mg,1.35 mmol), intermediate 4-1 (2.73 g,9.0 mmol), 2, 6-dimethylbenzoic acid (600 mg,4.2 mmol) and toluene (30 ml) were placed in a vial. The vessel was then sealed and heated at 130 ℃ for 18 hours. The resulting mixture was cooled to room temperature and filtered through silica gel while eluting with EtOAc. The eluent was evaporated and the residue was purified by flash column chromatography (hexane) to give intermediate 4-2 (2.01 g, 98%) as a white solid.
Synthesis of intermediate 4-3
Saturated NaOH ethanol (C) 2 H 5 OH) solution was added to a mixture of 3-aminopyridine formaldehyde (953 mg,7.8 mmol) and intermediate 4-2 (1.77 g,7.8 mmol) in anhydrous ethanol, and the mixture was refluxed overnight. After cooling the mixture, the precipitate was collected by filtration and taken from CH 2 Cl 2 The solution was recrystallized to obtain intermediate 4-3 (1.66 g, 68%).
Synthesis of Compound 4
Intermediate 4-3 (4.46 mmol) was dissolved in 2-ethoxyethanol (18 ml) in a 50ml round bottom flask. IrCl is added to 3 ·3H 2 O (2.01 mmol) and water (6 ml) were added to the flask. The resulting mixture was stirred under nitrogen at 120 ℃ for 24 hours and cooled to room temperature. The precipitate formed in the mixture was collected, washed with methanol and hexane, and dried in vacuo to obtain Ir (III) chloro-bridged dimer. Ir (III) chlorine bridged dimer, acetylacetone (3.02 mmol) and Na 2 O 3 (6.03 mmol) and 2-ethoxyethanol (20 ml) were mixed together and the resulting mixture was heated at 100℃for 6 hours. After cooling to room temperature, the precipitated solid was collected by filtration and washed with ethanol and hexane. The residue was dissolved in dichloromethane and the solid was filtered. The solution was concentrated in vacuo, and the residue was purified on a silica gel column and recrystallized to obtain compound 4 (14%).
Compounds 1 to 10 were synthesized in substantially the same manner as in Synthesis examples 1 to 3, except that the substituents of the starting materials and intermediate compounds were appropriately changed. Compounds 1 to 10 1 H NMRMS/FAB is shown in Table 1. By referring to the synthetic route and the starting materials described above, one skilled in the art can easily recognize synthetic methods for other compounds than those shown in table 1.
TABLE 1
Example 1
As an anode, 15 Ω/cm from Corning Inc (Corning Inc.) was used 2 The ITO glass substrate was cut into dimensions of 50mm×50mm×0.7mm, each was sonicated for 5 minutes using isopropyl alcohol and pure water, and then cleaned by ultraviolet irradiation and exposure to ozone for 30 minutes. Then, the obtained glass substrate was loaded onto a vacuum deposition apparatus.
Vacuum deposition of HT3 on anode to form a cathode havingAnd vacuum depositing HT40 on the hole injection layer to form a layer having +.>A hole transport layer of a thickness of (a).
Co-depositing (at a weight ratio of 45:45:10) H125 and H126 as hosts and compound 1 as a dopant on the hole transport layer to form a thin film havingIs a layer of a thickness of the emissive layer.
Vacuum deposition of ET37 on an emissive layer to form a light emitting device havingIs provided. Next, ET46 and Liq are co-deposited on the buffer layer in a weight ratio of 5:5 to form a film having +.>Is deposited on the electron transport layer in vacuum to form an electron transport layer having a thickness of +.>Is deposited on the cathode electrode to form a cathode electrode having a thickness of +.>To complete the manufacture of the light emitting device. />
Examples 2 to 10 and comparative examples 1 to 9
An organic light-emitting device was manufactured in substantially the same manner as in example 1, but in forming an emission layer, the compound shown in table 2 was used as a dopant instead of the compound 1.
Evaluation example 1
The emission spectrum of each light emitting device manufactured in examples 1 to 10 and comparative examples 1 to 9 was measured using a quanta-QY absolute PL quantum yield spectrometer (equipped with a xenon light source, a monochromator, a photon multichannel analyzer, and an integrating sphere) of the bingo company (Hamamatsu inc.) and using PLQY measurement software (bingo photonics limited (Hamamatsu Photonics, ltd.), jingsu county, japan), and the maximum emission wavelength (λ) max ) And FWHM is measured and displayed Shown in table 2.
TABLE 2
As can be seen from table 2, the maximum emission wavelengths of the light emitting devices of comparative examples 1 and 6 to 9 were not in the range of 610nm to 640nm, and the light emitting devices of comparative examples 1, 2, 4 and 5 had significantly higher FWHM than those of examples 1 to 10.
Evaluation example 2
Evaluation of light-emitting devices manufactured in examples 1 to 10 and comparative examples 1 to 5 at 400cd/m using a luminance meter (Minolta) Cs-1000A 2 Color purity (CIEx and CIEy coordinates) and forward (0 °) luminous efficiency under the conditions, and the results are shown in table 3. The forward luminous efficiency is expressed as a relative value to comparative example 1.
TABLE 3 Table 3
As can be seen from table 3, the light emitting devices of examples 1 to 10 have higher light emitting efficiency than the light emitting devices of comparative examples 1 to 5.
The organometallic compound can be used to manufacture a light-emitting device having high color purity and high forward luminous efficiency, and the light-emitting device can be used to manufacture high-quality electronic equipment.
It should be understood that the embodiments described herein should be considered in descriptive sense only and not for purposes of limitation. The description of features or aspects within each embodiment should generally be considered to be applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims and their equivalents.

Claims (20)

1. A light emitting device comprising:
a first electrode;
a second electrode facing the first electrode;
an intermediate layer between the first electrode and the second electrode and comprising an emissive layer; and
an organometallic compound represented by formula 1:
1 (1)
M(L 1 ) n1 (L 2 ) n2
2, 2
2A
Wherein M in formula 1 is a transition metal,
in formula 1, L 1 Is a ligand represented by formula 2, and n1 is 1, 2 or 3, wherein when n1 is 2 or greater than 2, two or more L 1 The same as or different from each other,
in formula 1, L 2 Is an organic ligand, and n2 is 0, 1 or 2, wherein when n2 is 2, two L' s 2 The same as or different from each other,
in formula 1, n1 plus n2 is equal to 2 or 3,
in the case of the formulas 2 and 2A,
Y 1 is N, the number of which is N,
Y 2 is C or N, and is not limited to the above,
ring CY 11 Is a nitrogen-containing ring containing at least one N element as a ring-forming atom,
ring CY 12 Cycle CY 21 And a ring CY 22 Each independently is C 5 -C 30 Carbocyclic group or C 1 -C 30 A heterocyclic group which is a heterocyclic group,
Y 11 to Y 13 And Y 21 To Y 23 Each of which is independently C or N,
Y 1 and Y 11 、Y 1 And Y 12 、Y 12 And Y 13 、Y 2 And Y 21 、Y 2 And Y 22 And Y 22 And Y 23 Each independently linked together via a single bond or a double bond,
Y a and Y b Each is the same as Y in formula 2 23 Or Y 22 Is used for the binding site of (a),
Z 21 is N (R) 21a )、O、S、Se、C(R 21a )(R 21b ) Or Si (R) 21a )(R 21b )，
R 11 、R 12 、R 21 、R 22 、R 21a And R is 21b Each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl radicals, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkenyl radicals, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkynyl radicals, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkoxy radicals, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkylthio radicals, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclic groups, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclic groups, unsubstituted orIs at least one R 10a Substituted C 6 -C 60 Aryloxy radicals, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Arylthio group, -C (Q) 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 ) or-P (=O) (Q 1 )(Q 2 )，
d11, d12, d21 and d22 are each independently integers from 0 to 20,
R 11 、R 12 、R 21 、R 22 、R 21a and R is 21b Optionally two or more groups of (a) are bonded together to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 60 Carbocyclic groups being either unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 A heterocyclic group which is a heterocyclic group,
* And each represents a binding site to M in formula 1,
R 10a the method comprises the following steps:
deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group or a nitro group;
each unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocycle group, C 1 -C 60 Heterocyclic groups, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio groups, C 7 -C 60 Arylalkyl radicals, C 2 -C 60 Heteroarylalkyl group, -Si (Q) 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(＝O)(Q 11 )、-S(＝O) 2 (Q 11 )、-P(＝O)(Q 11 )(Q 12 ) Or any combination thereof 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups or C 1 -C 60 An alkoxy group;
each unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl radicals, C 1 -C 60 Alkoxy groups, C 3 -C 60 Carbocycle group, C 1 -C 60 Heterocyclic groups, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio groups, C 7 -C 60 Arylalkyl radicals, C 2 -C 60 Heteroarylalkyl group, -Si (Q) 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(＝O)(Q 21 )、-S(＝O) 2 (Q 21 )、-P(＝O)(Q 21 )(Q 22 ) Or any combination thereof 3 -C 60 Carbocycle group, C 1 -C 60 Heterocyclic groups, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio groups, C 7 -C 60 Arylalkyl radicals or C 2 -C 60 A heteroarylalkyl group; or alternatively
-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 ) or-P (=O) (Q 31 )(Q 32 ) A kind of electronic device
Q 1 To Q 3 、Q 11 To Q 13 、Q 21 To Q 23 Q and 31 to Q 33 Each independently is: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; or each unsubstituted or deuterium, -F, cyano, C 1 -C 60 Alkyl group, C 1 -C 60 C substituted with an alkoxy group, a phenyl group, a biphenyl group, or any combination thereof 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl radicals, C 1 -C 60 Alkoxy groupsGroup C 3 -C 60 Carbocycle group, C 1 -C 60 Heterocyclic groups, C 7 -C 60 Arylalkyl radicals or C 2 -C 60 A heteroarylalkyl group.
2. The light emitting device of claim 1, wherein the first electrode is an anode,
the second electrode is a cathode electrode and,
the intermediate layer contains the organometallic compound represented by formula 1,
the intermediate layer further includes a hole transport region between the first electrode and the emissive layer and an electron transport region between the emissive layer and the second electrode,
the hole transport region comprises a hole injection layer, a hole transport layer, an emission auxiliary 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.
3. The light-emitting device according to claim 1, wherein the emission layer contains the organometallic compound represented by formula 1.
4. The light-emitting device of claim 3, wherein the emission layer emits light having a maximum emission wavelength of 610nm to 640 nm.
5. The light emitting device of claim 3, wherein the emissive layer emits light having a CIE (x) value of 0.65 or greater than 0.65.
6. An electronic device comprising the light-emitting device according to claim 1.
7. The electronic device of claim 6, further comprising a thin film transistor,
wherein the thin film transistor includes a source electrode and a drain electrode, and
the first electrode of the light emitting device is electrically connected to at least one of the source electrode and the drain electrode of the thin film transistor.
8. The electronic device of claim 6, further comprising a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.
9. The electronic device of claim 6, further comprising:
a thin film transistor; and
a color filter, a color conversion layer, a touch screen layer, a polarizing layer or any combination thereof,
wherein the thin film transistor includes a source electrode and a drain electrode, and
the first electrode of the light emitting device is electrically connected to the source electrode or the drain electrode.
10. An electronic device comprising the light emitting device of claim 1, wherein the electronic device is a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor light and/or signal light, a heads-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a retractable display, a laser printer, a telephone, a cellular telephone, a tablet personal computer, a tablet telephone, a personal digital assistant, a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a micro display, a three-dimensional display, a virtual or augmented reality display, a vehicle, a video wall where multiple displays are stitched together, a theatre screen or stadium screen, a phototherapy device or a sign.
11. An organometallic compound represented by formula 1:
1 (1)
M(L 1 ) n1 (L 2 ) n2
2, 2
2A
Wherein M in formula 1 is a transition metal,
in formula 1, L 1 Is a ligand represented by formula 2, and n1 is 1, 2 or 3, wherein when n1 is 2 or greater than 2, two or more L 1 The same as or different from each other,
in formula 1, L 2 Is an organic ligand, and n2 is 0, 1 or 2, wherein when n2 is 2, two L' s 2 The same as or different from each other,
in formula 1, n1 plus n2 is equal to 2 or 3,
in the case of the formulas 2 and 2A,
Y 1 is N, the number of which is N,
Y 2 is C or N, and is not limited to the above,
ring CY 11 Is a nitrogen-containing ring containing at least one N element as a ring-forming atom,
ring CY 12 Cycle CY 21 And a ring CY 22 Each independently is C 5 -C 30 Carbocyclic group or C 1 -C 30 A heterocyclic group which is a heterocyclic group,
Y 11 to Y 13 And Y 21 To Y 23 Each of which is independently C or N,
Y 1 and Y 11 、Y 1 And Y 12 、Y 12 And Y 13 、Y 2 And Y 21 、Y 2 And Y 22 And Y 22 And Y 23 Each independently linked together via a single bond or a double bond,
Y a and Y b Each is the same as Y in formula 2 23 Or Y 22 Is used for the binding site of (a),
Z 21 is N (R) 21a )、O、S、Se、C(R 21a )(R 21b ) Or Si (R) 21a )(R 21b )，
R 11 、R 12 、R 21 、R 22 、R 21a And R is 21b Each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl radicals, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkenyl radicals, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkynyl radicals, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkoxy radicals, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkylthio radicals, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclic groups, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclic groups, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Aryloxy radicals, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Arylthio group, -C (Q) 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 ) or-P (=O) (Q 1 )(Q 2 )，
d11, d12, d21 and d22 are each independently integers from 0 to 20,
R 11 、R 12 、R 21 、R 22 、R 21a and R is 21b Optionally two or more groups of (a) are bonded together to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 60 Carbocyclic groups being either unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 A heterocyclic group which is a heterocyclic group,
* And each represents a binding site to M in formula 1,
R 10a the method comprises the following steps:
deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group or a nitro group;
each unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocycle group, C 1 -C 60 Heterocyclic groups, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio groups, C 7 -C 60 Arylalkyl radicals, C 2 -C 60 Heteroarylalkyl group, -Si (Q) 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(＝O)(Q 11 )、-S(＝O) 2 (Q 11 )、-P(＝O)(Q 11 )(Q 12 ) Or any combination thereof 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups or C 1 -C 60 An alkoxy group;
each unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl radicals, C 1 -C 60 Alkoxy groups, C 3 -C 60 Carbocycle group, C 1 -C 60 Heterocyclic groups, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio groups, C 7 -C 60 Arylalkyl radicals, C 2 -C 60 Heteroarylalkyl group, -Si (Q) 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(＝O)(Q 21 )、-S(＝O) 2 (Q 21 )、-P(＝O)(Q 21 )(Q 22 ) Or any combination thereof 3 -C 60 Carbocycle group, C 1 -C 60 Heterocyclic groups, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio groups, C 7 -C 60 Arylalkyl radicals or C 2 -C 60 A heteroarylalkyl group; or alternatively
-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 ) or-P (=O) (Q 31 )(Q 32 ) A kind of electronic device
Q 1 To Q 3 、Q 11 To Q 13 、Q 21 To Q 23 Q and 31 to Q 33 Each independently is: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; or each unsubstituted or deuterium, -F, cyano, C 1 -C 60 Alkyl group, C 1 -C 60 C substituted with an alkoxy group, a phenyl group, a biphenyl group, or any combination thereof 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl radicals, C 1 -C 60 Alkoxy groups, C 3 -C 60 Carbocycle group, C 1 -C 60 Heterocyclic groups, C 7 -C 60 Arylalkyl radicals or C 2 -C 60 A heteroarylalkyl group.
12. The organometallic compound according to claim 11, wherein in formula 1, M is iridium or osmium, and n1 plus n2 is equal to 3, or
In formula 1, M is platinum, and n1 plus n2 equals 2.
13. The organometallic compound according to claim 11, wherein the cyclic CY 11 Is a pyrrole group, imidazole group, benzimidazole group, indole group, isoindole group, indazole group, purine group, quinoline group, isoquinoline group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group or triazine group.
14. The organometallic compound according to claim 11, wherein the group represented by formula 2 is a group represented by formulae 2 to 11 or formulae 2 to 12:
wherein, in the formulas 2 to 11 and 2 to 12,
X 13 is C (R) 13 ) Or N, X 14 Is C (R) 14 ) Or N, X 23 Is C (R) 23 ) Or N, X 24 Is C (R) 24 ) Or N, or a combination of two,
R 13 and R is 14 Each and in claim 11 with respect to R 11 The same is described with respect to the case,
R 23 and R is 24 Each and in claim 11 with respect to R 21 The same as described, and
Y 1 、Y 2 、CY 12 、CY 22 、Y 12 、Y 13 、Z 21 、R 12 、R 22 d12, d22, and are each the same as described in claim 11.
15. The organometallic compound according to claim 11, wherein the metal represented by formula 2The group represented is a group represented by one of the formulas 3-1 to 3-8:
wherein, in the formulas 3-1 to 3-8,
X 23 is C (R) 23 ) Or N, X 24 Is C (R) 24 ) Or N, X 25 Is C (R) 25 ) Or N, X 26 Is C (R) 26 ) Or N, X 27 Is C (R) 27 ) Or N, X 28 Is C (R) 28 ) Or N, X 29 Is C (R) 29 ) Or N, or a combination of two,
R 23 to R 29 Each and in claim 11 with respect to R 21 The same is described with respect to the case,
Y 2 and Z 21 Are each the same as described in claim 11, and
* 'and' each denote a binding site to an adjacent atom.
16. The organometallic compound according to claim 11, wherein the metal represented by formula 2The group represented is a group represented by one of the formulas 4-1 to 4-13:
wherein, in the formulas 4-1 to 4-13,
X 13 is C (R) 13 ) Or N, X 14 Is C (R) 14 ) Or N, X 15 Is C (R) 15 ) Or N, X 16 Is C (R) 16 ) Or N, X 17 Is C (R) 17 ) Or N, X 18 Is C (R) 18 ) Or N, X 19 Is C (R) 19 ) Or N, and X 20 Is C (R) 20 ) Or N, or a combination of two,
Z 19 is N (R) 19a )、O、S、Se、C(R 19a )(R 19b ) Or Si (R) 19a )(R 19b )，
R 13 To R 20 、R 17a To R 20a And R is 17b To R 20b Each and in claim 11 with respect to R 11 The same is described with respect to the case,
Y 1 as described in claim 11, and
* And "each represents a binding site to an adjacent atom.
17. The organometallic compound according to claim 11, wherein L 1 And L 2 Is a different ligand, and n2 is 1 or an integer greater than 1.
18. The organometallic compound according to claim 11, wherein L 2 Represented by one of formulas 5-1 to 5-6:
wherein, in the formulas 5-1 to 5-6,
Y 51 is O, N, N (E) 51a )、P(E 51a )(E 51b ) Or As (E) 51a )(E 52a )，
Y 52 Is O, N, N (E) 52a )、P(E 52a )(E 52b ) Or As (E) 52a )(E 52b )，
T 51 Is a single bond, a double bond, -C (R) 51 )(R 52 )-*'、*-C(R 51 )＝C(R 52 )-*'、*＝C(R 51 )-*'、*-C(R 51 )＝*'、*＝C(R 51 )-C(R 52 )＝C(R 53 )-*'、*-C(R 51 )＝C(R 52 )-C(R 53 ) = or-N (R 51 )-*'，
Y 53 To Y 56 Each of which is independently C or N,
Y 57 is C, N (E) 57a ) Or P (E) 57a )，
Y 58 Is N (E) 58a )(R 58b )、P(E 58a )(E 58b )(E 58c ) Or As (E) 58a )(E 58b )(E 58c )，
Y 59 Is N (E) 59a )(E 59b )、P(E 59a )(E 59b )(E 59c ) Or As (E) 59a )(E 59b )(E 59c )，
Ring A 51 And ring A 52 Each independently is C 4 -C 60 Carbocycle group or C 1 -C 60 A heterocyclic group which is a heterocyclic group,
E 51 、E 52 、E 51a 、E 51b 、E 52a 、E 52b 、E 57a 、E 58a 、E 58b 、E 58c 、E 59a 、E 59b 、E 59c and R is 51 To R 53 Each and in claim 11 with respect to R 11 The same is described with respect to the case,
c51 and c52 are each independently an integer of 0 to 10, and
* And each represents a binding site to M in formula 1.
19. The organometallic compound according to claim 11, wherein d 11R 11 D 12R 12 D 21R 21 D 22R 22 、R 21a And R is 21b Is not hydrogen.
20. The organometallic compound of claim 11, wherein the organometallic compound is one of compound 1 to compound 10:
CN202310573782.7A 2022-05-23 2023-05-22 Organometallic compound, light-emitting device, electronic device, and electronic apparatus Pending CN117105988A (en)

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KR10-2022-0141760 2022-10-28
KR1020220141760A KR20230163914A (en) 2022-05-23 2022-10-28 Organometallic compound, light emitting device including the organometallic compound, and electronic apparatus and electronic device including the light emitting device

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