阅读说明：本技术 有机化合物及包含其的有机电致发光元件 (Organic compound and organic electroluminescent element comprising same ) 是由 金弘锡 金荣培 于 2018-05-02 设计创作，主要内容包括：本发明涉及新型化合物及包含其的有机电致发光元件,通过将本发明的化合物用于有机电致发光元件的有机物层、优选为发光层,从而能够提高有机电致发光元件的发光效率、驱动电压、寿命等。(The present invention relates to a novel compound and an organic electroluminescent device comprising the same, wherein the compound of the present invention is used in an organic layer, preferably a light-emitting layer, of the organic electroluminescent device, thereby improving the luminous efficiency, driving voltage, lifetime, and the like of the organic electroluminescent device.)

1. A compound represented by the following chemical formula 1:

[ chemical formula 1]

In the chemical formula 1, the metal oxide is represented by,

X₁selected from the group consisting of S, O, N (R)₁) And C (R)₂)(R₃) A group of (a);

X₂and X₃Each independently is N or C (Ar)₁) And at least one is C (Ar)₁)；

Ring a is represented by any one of the following chemical formulae 2 to 4;

[ chemical formula 2]

[ chemical formula 3]

[ chemical formula 4]

In the chemical formulae 1 to 4,

the dotted line means that a condensed moiety is formed;

m is an integer of 0 to 4;

n is an integer of 0 to 6;

R₁to R₄Each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₁～C₄₀Alkoxy group of (C)₆～C₆₀Aryloxy group of (A), C₃～C₄₀Alkylsilyl group of (C)₆～C₆₀Arylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀Arylamine groups of (a);

the R is₁To R₄Each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C, alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylboryl, arylboryl, arylphosphino, mono-or diarylphosphinoyl, and arylsilyl₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₆～C₆₀Aryloxy group of (A), C₁～C₄₀Alkoxy group of (C)₆～C₆₀Arylamino group of (C)₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₁～C₄₀Alkylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of、C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀One or more substituents of the group consisting of arylsilyl groups of (a), when substituted with a plurality of substituents, are the same as or different from each other;

Ar₁is a substituent represented by the following chemical formula 5 when said Ar₁When plural, they are the same as or different from each other;

[ chemical formula 5]

In the chemical formula 5, the first and second organic solvents,

by "means the moiety that forms the bond;

L₁and L₂Each independently selected from the group consisting of direct bond, C₆～C₁₈And a heteroarylene group having a nuclear number of 5 to 18;

Ar₂selected from hydrogen, deuterium, halogen, cyano, nitro, C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₁～C₄₀Alkoxy group of (C)₆～C₆₀Aryloxy group of (A), C₃～C₄₀Alkylsilyl group of (C)₆～C₆₀Arylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀Arylamine groups of (a);

said L₁And L₂And said Ar and arylene and heteroarylene of₂Alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamine, aryl, heteroaryl,the alkylsilyl, the alkylboron group, the arylboron group, the arylphosphine group, the mono-or diarylphosphino group and the arylsilyl group are independently selected from deuterium, halogen, cyano, nitro and C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₆～C₆₀Aryloxy group of (A), C₁～C₄₀Alkoxy group of (C)₆～C₆₀Arylamino group of (C)₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₁～C₄₀Alkylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀When a plurality of substituents are substituted, they may be the same as or different from each other.

2. The compound according to claim 1, which is represented by any one of the following chemical formulae 6 to 14:

[ chemical formula 6]

[ chemical formula 7]

[ chemical formula 8]

[ chemical formula 9]

[ chemical formula 10]

[ chemical formula 11]

[ chemical formula 12]

[ chemical formula 13]

[ chemical formula 14]

In the chemical formulae 6 to 14,

ring A, Ar₁And R₁To R₃Each as defined in claim 1.

3. A compound according to claim 1, said R₁To R₄Each independently selected from C₁～C₄₀Alkyl of (C)₆～C₆₀Aryl and heteroaryl having a nuclear number of 5 to 60,

the R is₁To R₄Each independently of the others, is selected from the group consisting of C₁～C₄₀Alkyl of (C)₆～C₆₀When substituted with a plurality of substituents selected from the group consisting of aryl and heteroaryl having 5 to 60 atomic nucleiWhen the substituents are present, they may be the same as or different from each other.

4. The compound of claim 1, said L₁And L₂Each independently is a direct bond, or a linking group represented by any one of the following formulas A-1 to A-7:

in the chemical formulae A-1 to A-7,

by "means the moiety that forms the bond;

Z₁to Z₈Each independently is N or C (R)₅)；

In the formula A-1, Z as a linking group forming a bond₁To Z₆Any two of (A) and (B) are C (R)₅) At this time, the R₅Is absent;

in the formula A-4, Z as a linking group forms a bond₁To Z₄Any one of and Z₅To Z₈Any one of them is C (R)₅) At this time, the R₅Is absent;

in the formula A-5, Z as a linking group forming a bond₁To Z₄Any two of (A) and (B) are C (R)₅) At this time, the R₅Is absent;

X₄and X₅Each independently is O, S, N (R)₆) Or C (R)₇)(R₈)；

X₆Is N or C (R)₉)；

R₅To R₉Each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₁～C₄₀Alkoxy of (2)Base, C₆～C₆₀Aryloxy group of (A), C₃～C₄₀Alkylsilyl group of (C)₆～C₆₀Arylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀Or an arylamine group of (A) or (B) is bonded to an adjacent group to form a condensed ring when R is₅To R₈When each is plural, they are the same as or different from each other;

the R is₅To R₉Each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C, alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylboryl, arylboryl, arylphosphino, mono-or diarylphosphinoyl, and arylsilyl₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₆～C₆₀Aryloxy group of (A), C₁～C₄₀Alkoxy group of (C)₆～C₆₀Arylamino group of (C)₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₁～C₄₀Alkylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀When a plurality of substituents are substituted, they may be the same as or different from each other.

5. The compound of claim 1, said L₁And L₂Each independently is a direct bond, or represented by any one of the following chemical formulas B-1 to B-12Linking group:

in the chemical formulae B-1 to B-12,

by "means the moiety that forms the bond;

R₆to R₉Each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₁～C₄₀Alkoxy group of (C)₆～C₆₀Aryloxy group of (A), C₃～C₄₀Alkylsilyl group of (C)₆～C₆₀Arylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀Arylamine groups of (a);

the R is₆To R₉Each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C, alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylboryl, arylboryl, arylphosphino, mono-or diarylphosphinoyl, and arylsilyl₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₆～C₆₀Aryloxy group of (A), C₁～C₄₀Alkoxy group of (C)₆～C₆₀Arylamino group of (C)₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₁～C₄₀Alkyl silyl ofBase, C₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀When a plurality of substituents are substituted, they may be the same as or different from each other.

6. The compound of claim 1, said Ar₂Is C₆～C₆₀An aryl group, a heteroaryl group having 5 to 60 atomic nuclei, or an arylamine group of (A),

ar is₂Each aryl, heteroaryl, arylamine group of (A) is independently selected from C₁～C₄₀Alkyl of (C)₆～C₆₀Arylamino group of (C)₆～C₆₀And one or more substituents selected from the group consisting of aryl and heteroaryl having a nuclear number of 5 to 60, which may be the same or different from each other when substituted with a plurality of substituents.

7. The compound of claim 1, said Ar₂Is a substituent represented by the following chemical formula 15:

[ chemical formula 15]

In the chemical formula 15, the compound represented by the formula,

by "means the moiety that forms the bond;

Y₁to Y₅Each independently is N or C (R)₁₀)；

R₁₀Selected from hydrogen, deuterium, halogen, cyano, nitro, C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₆～C₆₀Aryl of (2)Heteroaryl having a nuclear number of 5 to 60, C₁～C₄₀Alkoxy group of (C)₆～C₆₀Aryloxy group of (A), C₃～C₄₀Alkylsilyl group of (C)₆～C₆₀Arylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀When said R is an arylamine group₁₀When plural, they are the same as or different from each other;

the R is₁₀Each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C, alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylboryl, arylboryl, arylphosphino, mono-or diarylphosphinoyl, and arylsilyl₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₆～C₆₀Aryloxy group of (A), C₁～C₄₀Alkoxy group of (C)₆～C₆₀Arylamino group of (C)₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₁～C₄₀Alkylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀When a plurality of substituents are substituted, they may be the same as or different from each other.

8. The compound according to claim 7, wherein the substituent represented by chemical formula 15 is a substituent represented by chemical formula 16 below:

[ chemical formula 16]

In the chemical formula 16, the first and second groups,

by "means the moiety that forms the bond;

R₁₁and R₁₂Each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₁～C₄₀Alkoxy group of (C)₆～C₆₀Aryloxy group of (A), C₃～C₄₀Alkylsilyl group of (C)₆～C₆₀Arylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀Or an arylamine group of (b), or a condensed ring formed by bonding to an adjacent group;

the R is₁₁And R₁₂Each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C, alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylboryl, arylboryl, arylphosphino, mono-or diarylphosphinoyl, and arylsilyl₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₆～C₆₀Aryloxy group of (A), C₁～C₄₀Alkoxy group of (C)₆～C₆₀Arylamino group of (C)₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₁～C₄₀Alkylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀One or more substituents of the group consisting of arylsilyl groups of (a), when substituted with a plurality of substituents, are the same as or different from each other;

Y₁、Y₃and Y₅Each as defined in claim 7.

9. The compound according to claim 7, wherein the substituent represented by chemical formula 15 is a substituent represented by any one of the following chemical formulae C-1 to C-5:

in the chemical formulas C-1 to C-5,

by "is meant the portion that forms the bond,

R₁₁and R₁₂Each independently hydrogen, deuterium, halogen, cyano, nitro, C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₁～C₄₀Alkoxy group of (C)₆～C₆₀Aryloxy group of (A), C₃～C₄₀Alkylsilyl group of (C)₆～C₆₀Arylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀Or an arylamine group of (b), or a condensed ring formed by bonding to an adjacent group;

the R is₁₁And R₁₂Each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C, alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylboryl, arylboryl, arylphosphino, mono-or diarylphosphinoyl, and arylsilyl₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₆～C₆₀Aryloxy group of (A), C₁～C₄₀Alkoxy group of (C)₆～C₆₀Arylamino group of (C)₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₁～C₄₀Alkylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀When a plurality of substituents are substituted, they may be the same as or different from each other.

10. The compound of claim 9, said R₁₁And R₁₂Each independently selected from C₁～C₄₀Alkyl of (C)₆～C₆₀Aryl and heteroaryl having a nuclear number of 5 to 60,

the R is₁₁And R₁₂Each independently of the others, is selected from the group consisting of C₁～C₄₀Alkyl of (C)₆～C₆₀And one or more substituents selected from the group consisting of aryl groups having 5 to 60 atomic cores and heteroaryl groups having 5 to 60 atomic cores, which are the same or different from each other when substituted with a plurality of substituents.

11. The compound of claim 1, said Ar₂Is a substituent represented by the following chemical formula 17:

[ chemical formula 17]

In the chemical formula 17, the compound represented by the formula,

by "means the moiety that forms the bond;

R₁₃and R₁₄Each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₁～C₄₀Alkoxy group of (C)₆～C₆₀Aryloxy group of (A), C₃～C₄₀Alkylsilyl group of (C)₆～C₆₀Arylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀Or an arylamine group of (b), or a condensed ring formed by bonding to an adjacent group;

the R is₁₃And R₁₄Each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C, alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylboryl, arylboryl, arylphosphino, mono-or diarylphosphinoyl, and arylsilyl₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₆～C₆₀Aryloxy group of (A), C₁～C₄₀Alkoxy group of (C)₆～C₆₀Arylamino group of (C)₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₁～C₄₀Alkylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀When a plurality of substituents are substituted, they may be the same as or different from each other.

12. A compound according to claim 11, said R₁₃And R₁₄Each independently selected from C₁～C₄₀Alkyl of (C)₆～C₆₀Aryl and heteroaryl having a nuclear number of 5 to 60,

the R is₁₃And R₁₄Each independently of the others, is selected from the group consisting of C₁～C₄₀Alkyl of (C)₆～C₆₀And one or more substituents selected from the group consisting of aryl groups having 5 to 60 atomic cores and heteroaryl groups having 5 to 60 atomic cores, which are the same or different from each other when substituted with a plurality of substituents.

13. The compound of claim 1, wherein the compound is selected from the group consisting of:

14. an organic electroluminescent element comprising (i) an anode, (ii) a cathode, and (iii) one or more organic layers interposed between the anode and the cathode,

at least one of the organic layers includes the compound of formula 1 according to claim 1.

15. The organic electroluminescent element according to claim 14, wherein the organic layer comprises one or more layers selected from the group consisting of a hole injection layer, a hole transport auxiliary layer, an electron transport auxiliary layer, and a light-emitting layer.

Technical Field

The present invention relates to a novel organic compound which can be used as a material for an organic electroluminescent element, and an organic electroluminescent element containing the same.

Background

Since the beginning of the observation of Bernanose's organic thin film luminescence in the 50 th century, research into an organic Electroluminescent (EL) device developed by blue electroluminescence using anthracene single crystal in 1965 was carried out, and an organic electroluminescent device having a laminated structure of two functional layers, i.e., a hole layer and a light-emitting layer, was proposed in 1987 by Tang (Tang). Then, in order to manufacture an organic electroluminescent device having high efficiency and long life, a mode of introducing characteristic organic layers into the device has been developed, and a dedicated material for the introduction has been developed.

With respect to the organic electroluminescent element, if a voltage is applied between two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons (exiton) are formed, and when the excitons transition to a ground state, light is emitted. In this case, the substance used for the organic layer may be classified into a light-emitting substance, a hole-injecting substance, a hole-transporting substance, an electron-injecting substance, and the like according to its function.

The light emitting materials may be classified into blue, green, and red light emitting materials according to light emitting colors, and yellow and orange light emitting materials for representing more natural colors. In addition, as a light-emitting substance, a host/dopant system can be used for the purpose of an increase in color purity and an increase in light-emitting efficiency by energy transfer.

The dopant substance can be classified into a fluorescent dopant using an organic substance and a phosphorescent dopant using a metal complex containing heavy atoms (heavyatoms) such as Ir and Pt. In this case, since the development of phosphorescent materials can theoretically improve the light emission efficiency by 4 times as high as that of fluorescence, not only phosphorescent dopants but also phosphorescent host materials have been studied in large quantities.

As hole injection layer, hole transport layer, hole blocking layer, and electron transport layer materials, NPB, BCP, and Alq have been used so far₃Anthracene derivatives are widely known as materials for light-emitting layers. In particular, Firpic and Ir (ppy) which are advantageous in improving efficiency among the materials of the light emitting layer₃、(acac)Ir(btp)₂And the like, metal complex compounds containing Ir have been used as phosphorescent dopant materials for blue (blue), green (green), and red (red), and 4,4-dicarbazolybiphenyl (CBP) has been used as phosphorescent host materials.

However, conventional organic layer materials are superior in light-emitting characteristics, but have a low glass transition temperature and very poor thermal stability, and thus cannot achieve a satisfactory level in terms of the lifetime of an organic electroluminescent device. Therefore, development of an organic layer material having excellent properties is required.

Disclosure of Invention

Technical subject

The purpose of the present invention is to provide a novel organic compound which can be applied to an organic electroluminescent element and is excellent in hole and electron injection, transport ability, light-emitting ability, and the like.

Another object of the present invention is to provide an organic electroluminescent element which comprises the novel organic compound and exhibits a low driving voltage and high luminous efficiency and an improved lifetime.

Means for solving the problem

In order to achieve the above objects, the present invention provides a compound represented by the following chemical formula 1:

[ chemical formula 1]

In the chemical formula 1 described above,

X₁selected from the group consisting of S, O, N (R)₁) And C (R)₂)(R₃) A group of (a);

X₂and X₃Each independently is N or C (Ar)₁) And at least one is C (Ar)₁)；

Ring a is represented by any one of the following chemical formulae 2 to 4;

[ chemical formula 2]

[ chemical formula 3]

[ chemical formula 4]

In the above-mentioned chemical formulas 1 to 4,

the dotted line means that a condensed moiety is formed;

m is an integer of 0 to 4;

n is an integer of 0 to 6;

R₁to R₄Each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₁～C₄₀Alkoxy group of (C)₆～C₆₀Aryloxy group of (A), C₃～C₄₀Alkylsilyl group of (C)₆～C₆₀Arylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl (phosphinoyl), and C₆～C₆₀Arylamine groups of (a);

r is as defined above₁To R₄Each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C, alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylboryl, arylboryl, arylphosphino, mono-or diarylphosphinoyl, and arylsilyl₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₆～C₆₀Aryloxy group of (A), C₁～C₄₀Alkoxy group of (C)₆～C₆₀Arylamino group of (C)₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₁～C₄₀Alkylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀One or more substituents of the group consisting of arylsilyl groups of (a), when substituted with a plurality of substituents, are the same as or different from each other;

Ar₁is a substituent represented by the following chemical formula 5 when Ar is mentioned above₁When plural, they are the same as or different from each other;

[ chemical formula 5]

In the chemical formula 5 described above,

by "means the moiety that forms the bond;

L₁and L₂Are independently selected fromFree direct binding, C₆～C₁₈And a heteroarylene group having a nuclear number of 5 to 18;

Ar₂selected from hydrogen, deuterium, halogen, cyano, nitro, C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₁～C₄₀Alkoxy group of (C)₆～C₆₀Aryloxy group of (A), C₃～C₄₀Alkylsilyl group of (C)₆～C₆₀Arylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀Arylamine groups of (a);

l above₁And L₂Arylene and heteroarylene groups of (A) and Ar as described above₂Each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C, alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylboryl, arylboryl, arylphosphino, mono-or diarylphosphinoyl, and arylsilyl₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₆～C₆₀Aryloxy group of (A), C₁～C₄₀Alkoxy group of (C)₆～C₆₀Arylamino group of (C)₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₁～C₄₀Alkylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀When a plurality of substituents are substituted, they may be the same as or different from each other.

The present invention provides an organic electroluminescent element comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises the compound of formula 1.

The "alkyl group" in the present invention is a substituent having a valence of 1 derived from a straight-chain or side-chain saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, and hexyl.

The "alkenyl group" in the present invention is a substituent having a valence of 1 derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having 1 or more carbon-carbon double bonds, and examples thereof include a vinyl group (vinyl), an allyl group (allyl), an isopropenyl group (isopropenyl), a 2-butenyl group (2-butenyl), and the like, but are not limited thereto.

The "alkynyl group (alkynyl)" in the present invention is a substituent having a valence of 1 derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having 1 or more carbon-carbon triple bonds, and examples thereof include, but are not limited to, an ethynyl group (ethyl) and a 2-propynyl group (2-propyl).

The "aryl group" in the present invention means a 1-valent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms and having a single ring or a combination of 2 or more rings. Further, the compound may include a substituent having a valence of 1 in which 2 or more rings are condensed with each other, only carbon (for example, the number of carbon atoms may be 8 to 60) is contained as a ring-forming atom, and the whole molecule has a non-aromatic property (non-aromatic property). Examples of such aryl groups include, but are not limited to, phenyl, naphthyl, phenanthryl, anthracyl, fluorenyl, and the like.

The "heteroaryl" in the present invention means a substituent having a valence of 1 derived from a mono-or poly-heterocyclic aromatic hydrocarbon having an atomic number of 5 to 60. At this time, in the ringOne or more carbons of (a), preferably 1 to 3 carbons, are substituted with a heteroatom selected from N, O, P, S and Se. Further, the term "non-aromatic" is to be interpreted to include a group having a valence of 1 in which 2 or more rings are simply attached to each other (pendant) or condensed, a hetero atom selected from N, O, P, S and Se is contained as a ring-forming atom in addition to carbon, and the whole molecule has a non-aromatic property (non-aromatic property). Examples of such heteroaryl groups include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl; phen

Polycyclic rings such as thienyl (phenoxathienyl), indolizinyl (indolizinyl), indolyl (indoliyl), purinyl (purinyl), quinolyl (quinolyl), benzothiazolyl (benzothiazolyl), carbazolyl (carbazolyl), and the like; 2-furyl, N-imidazolyl, 2-isofuryl

Oxazolyl, 2-pyridyl, 2-pyrimidyl and the like, but are not limited thereto.

The "aryloxy group" in the present invention means a substituent having a valence of 1 represented by RO-, and the above R is an aryl group having 5 to 60 carbon atoms. Examples of such aryloxy groups include, but are not limited to, phenoxy, naphthoxy, and diphenoxy.

The "alkoxy group" in the present invention means a substituent having a valence of 1 represented by R 'O-, wherein R' is an alkyl group having 1 to 40 carbon atoms, and is interpreted to include a linear (linear), branched, or cyclic (cyclic) structure. Examples of such alkoxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, tert-butoxy, n-butoxy, and pentyloxy.

The "arylamine group" in the present invention means an amine group substituted with an aryl group having 6 to 60 carbon atoms.

The "cycloalkyl group" in the present invention means a 1-valent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl (norbonyl), adamantyl (adamantine), and the like.

The term "heterocycloalkyl" in the present invention means a 1-valent substituent derived from a non-aromatic hydrocarbon having 3 to 40 atomic nuclei, wherein one or more carbons, preferably 1 to 3 carbons, in the ring are substituted with a heteroatom such as N, O, S or Se. Examples of such heterocycloalkyl groups include, but are not limited to, morpholinyl and piperazinyl.

The "alkylsilyl group" in the present invention means a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, and the "arylsilyl group" means a silyl group substituted with an aryl group having 5 to 60 carbon atoms.

In the present invention, "condensed ring" means a form of condensed aliphatic ring, condensed aromatic ring, condensed aliphatic heterocyclic ring, condensed aromatic heterocyclic ring, or a combination thereof.

Effects of the invention

The compound of the present invention is excellent in thermal stability, carrier transport ability, light-emitting ability, and the like, and therefore can be effectively used as an organic layer material for an organic electroluminescent element.

In addition, an organic electroluminescent element in which the compound of the present invention is contained in an organic layer can be greatly improved in light-emitting performance, driving voltage, life, efficiency, and the like, and thus can be effectively applied to a full-color display panel and the like.

Drawings

Fig. 1 shows a cross-sectional view of an organic electroluminescent element according to an embodiment of the present invention.

Fig. 2 shows a cross-sectional view of an organic electroluminescent element according to an embodiment of the present invention.

Detailed Description

The present invention will be described in detail below.

1. Novel organic compounds

The novel compound of the present invention may be represented by the following chemical formula 1:

[ chemical formula 1]

In the chemical formula 1 described above,

X₁selected from the group consisting of S, O, N (R)₁) And C (R)₂)(R₃) A group of (a);

X₂and X₃Each independently is N or C (Ar)₁) And at least one is C (Ar)₁)；

Ring a is represented by any one of the following chemical formulae 2 to 4;

[ chemical formula 2]

[ chemical formula 3]

[ chemical formula 4]

In the above-mentioned chemical formulas 1 to 4,

the dotted line means that a condensed moiety is formed;

m is an integer of 0 to 4;

n is an integer of 0 to 6;

R₁to R₄Each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₁～C₄₀Alkoxy group of (C)₆～C₆₀Aryloxy group of (A), C₃～C₄₀Alkylsilyl group of (C)₆～C₆₀Arylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀An arylboron group of,C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀Arylamine groups of (a);

r is as defined above₁To R₄Each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C, alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylboryl, arylboryl, arylphosphino, mono-or diarylphosphinoyl, and arylsilyl₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₆～C₆₀Aryloxy group of (A), C₁～C₄₀Alkoxy group of (C)₆～C₆₀Arylamino group of (C)₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₁～C₄₀Alkylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀One or more substituents of the group consisting of arylsilyl groups of (a), when substituted with a plurality of substituents, are the same as or different from each other;

Ar₁is a substituent represented by the following chemical formula 5 when Ar is mentioned above₁When plural, they are the same as or different from each other;

[ chemical formula 5]

In the chemical formula 5 described above,

by "means the moiety that forms the bond;

L₁and L₂Each independently selected from the group consisting of direct bond, C₆～C₁₈And a heteroarylene group having a nuclear number of 5 to 18;

Ar₂selected from hydrogen, deuterium, halogen, cyano, nitro, C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₁～C₄₀Alkoxy group of (C)₆～C₆₀Aryloxy group of (A), C₃～C₄₀Alkylsilyl group of (C)₆～C₆₀Arylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀Arylamine groups of (a);

l above₁And L₂Arylene and heteroarylene groups of (A) and Ar as described above₂Each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C, alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylboryl, arylboryl, arylphosphino, mono-or diarylphosphinoyl, and arylsilyl₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₆～C₆₀Aryloxy group of (A), C₁～C₄₀Alkoxy group of (C)₆～C₆₀Arylamino group of (C)₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₁～C₄₀Alkylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀When a plurality of substituents are substituted, they may be the same as or different from each other.

More specifically, the compound represented by chemical formula 1 of the present invention is a compound in which EWG is bonded to a 5-membered aromatic ring or a 5-membered aromatic heterocyclic ring such as indole, indazole, indene, benzofuran, benzothiophene, triazole, or the like, and in this case, it has an energy level similar to that of carbazole, and therefore, can be adjusted to be higher than that of dopant and can be used as a host substance. In particular, benzofuran and benzothiophene have abundant electrons, and when used as an electron transport layer material for an organic electroluminescent device, they have high mobility, and thus an increase in light emission efficiency and a reduction in driving voltage can be expected. In addition, since the molecular weight of the 5-membered aromatic ring or the 5-membered aromatic heterocyclic ring of the present invention is smaller than that of a conventional compound, it is possible to perform vapor deposition at a relatively lower vapor deposition temperature than other materials at the time of vapor deposition, and therefore, the process is excellent and thermal stability can be improved.

Thus, the compound represented by chemical formula 1 of the present invention can be used as an organic material of an organic electroluminescent device, preferably a light-emitting material (green phosphorescent host material), an electron transporting layer/injection layer material, a light-emitting auxiliary layer material, an electron transporting auxiliary layer material, more preferably a light-emitting layer material, an electron transporting layer material, or an electron transporting auxiliary layer material. In addition, the organic electroluminescent element including the compound of chemical formula 1 can greatly improve performance and life characteristics, and the performance of a full-color organic light-emitting panel to which such an organic electroluminescent element is applied can be maximized.

According to a preferred embodiment of the present invention, the above compound may be represented by any one of the following chemical formulas 6 to 14:

[ chemical formula 6]

[ chemical formula 7]

[ chemical formula 8]

[ chemical formula 9]

[ chemical formula 10]

[ chemical formula 11]

[ chemical formula 12]

[ chemical formula 13]

[ chemical formula 14]

In the above-mentioned chemical formulas 6 to 14,

ring A, Ar₁And R₁To R₃Each is as defined in chemical formula 1.

According to a preferred embodiment of the present invention, among the compounds, the compound represented by any one of the above chemical formulas 6 to 8 is preferable, and can be represented by the above chemical formula 6 or 7 is more preferable, and can be represented by the above chemical formula 8 or 10 is further preferable, from the viewpoint of ensuring a low driving voltage and high luminous efficiency.

According to a preferred embodiment of the present invention, R is₁To R₄Each independently selected from C₁～C₄₀Alkyl of (C)₆～C₆₀Aryl and heteroaryl having a nuclear number of 5 to 60,

r is as defined above₁To R₄Each independently of the others, is selected from the group consisting of C₁～C₄₀Alkyl of (C)₆～C₆₀And one or more substituents selected from the group consisting of aryl and heteroaryl having a nuclear number of 5 to 60, wherein when a plurality of substituents are substituted, they may be the same or different from each other.

According to a preferred embodiment of the present invention, R is₁To R₄Each independently selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, fluorenyl, spirofluorenyl, and dibenzo

A group consisting of an English base and a compound of,

r is as defined above₁To R₄Methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, fluorenyl, spirofluorenyl and dibenzobisthienyl ofEach of the English radicals is independently selected from C₁～C₄₀Alkyl of (C)₆～C₆₀Arylamino group of (C)₆～C₆₀And one or more substituents selected from the group consisting of aryl and heteroaryl having a nuclear number of 5 to 60, which may be the same or different from each other when substituted with a plurality of substituents.

According to a preferred embodiment of the inventionMode for carrying out the invention, the above-mentioned L₁And L₂Each independently is preferably a direct bond, or a linking group represented by any one of the following formulae a-1 to a-7, but is not limited thereto:

in the above chemical formulae A-1 to A-7,

by "means the moiety that forms the bond;

Z₁to Z₈Each independently is N or C (R)₅)；

In the above formula A-1, Z as a linking group forming a bond₁To Z₆Any two of (A) and (B) are C (R)₅) At this time, R is as defined above₅Is absent;

in the above chemical formula A-4, Z as a linking group forming a bond₁To Z₄Any one of and Z₅To Z₈Any one of them is C (R)₅) At this time, R is as defined above₅Is absent;

in the above chemical formula A-5, Z as a linking group forming a bond₁To Z₄Any two of (A) and (B) are C (R)₅) At this time, R is as defined above₅Is absent;

X₄and X₅Each independently is O, S, N (R)₆) Or C (R)₇)(R₈)；

X₆Is N or C (R)₉)；

R₅To R₉Each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₁～C₄₀Alkoxy group of (C)₆～C₆₀Aryloxy group of (A), C₃～C₄₀Alkylsilyl group of (C)₆～C₆₀Arylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀Or an arylamine group of (A) or an arylamine group of (B) is bonded to an adjacent group to form a condensed ring, when R is as defined above₅To R₈When each is plural, they are the same as or different from each other;

r is as defined above₅To R₉Each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C, alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylboryl, arylboryl, arylphosphino, mono-or diarylphosphinoyl, and arylsilyl₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₆～C₆₀Aryloxy group of (A), C₁～C₄₀Alkoxy group of (C)₆～C₆₀Arylamino group of (C)₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₁～C₄₀Alkylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀When a plurality of substituents are substituted, they may be the same as or different from each other.

According to a preferred embodiment of the present invention, L is₁And L₂Each independently is preferably a direct bond, or a linking group represented by any one of the following formulas B-1 to B-12, but is not limited thereto:

in the above chemical formulae B-1 to B-12,

by "means the moiety that forms the bond;

R₆to R₉Each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₁～C₄₀Alkoxy group of (C)₆～C₆₀Aryloxy group of (A), C₃～C₄₀Alkylsilyl group of (C)₆～C₆₀Arylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀Arylamine groups of (a);

r is as defined above₆To R₉Each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C, alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylboryl, arylboryl, arylphosphino, mono-or diarylphosphinoyl, and arylsilyl₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₆～C₆₀Aryloxy group of (A), C₁～C₄₀Alkoxy group of (C)₆～C₆₀Arylamino group of (C)₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₁～C₄₀Alkylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀An aryl phosphine group,C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀When a plurality of substituents are substituted, they may be the same as or different from each other.

According to a preferred embodiment of the present invention, in the above chemical formulas B-1 to B-12, R is₆To R₉Each independently selected from hydrogen, C₁～C₄₀Alkyl of (C)₆～C₆₀Aryl and heteroaryl with a nuclear number of 5 to 60;

r is as defined above₆To R₉Each independently of the others, is selected from the group consisting of C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₆～C₆₀And one or more substituents selected from the group consisting of aryl groups having 5 to 60 atomic cores and heteroaryl groups having 5 to 60 atomic cores, which are the same or different from each other when substituted with a plurality of substituents.

According to a preferred embodiment of the present invention, L is₁And L₂Each independently may be a direct bond, or a linking group selected from the group consisting of the above formulae B-1 to B-3 and B-7 to B-12.

According to a preferred embodiment of the present invention, Ar is₂Is C₆～C₆₀Aryl or heteroaryl, arylamine with 5 to 60 atomic cores,

ar above₂Each aryl, heteroaryl, arylamine group of (A) is independently selected from C₁～C₄₀Alkyl of (C)₆～C₆₀Arylamino group of (C)₆～C₆₀And one or more substituents selected from the group consisting of aryl and heteroaryl having a nuclear number of 5 to 60, which may be the same or different from each other when substituted with a plurality of substituents.

According to a preferred embodiment of the present invention, Ar is₂May be a substituent represented by the following chemical formula 15:

[ chemical formula 15]

In the chemical formula 15 described above, the,

by "means the moiety that forms the bond;

Y₁to Y₅Each independently is N or C (R)₁₀)；

R₁₀Selected from hydrogen, deuterium, halogen, cyano, nitro, C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₁～C₄₀Alkoxy group of (C)₆～C₆₀Aryloxy group of (A), C₃～C₄₀Alkylsilyl group of (C)₆～C₆₀Arylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀When R is the above-mentioned₁₀When plural, they are the same as or different from each other;

r is as defined above₁₀Each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C, alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylboryl, arylboryl, arylphosphino, mono-or diarylphosphinoyl, and arylsilyl₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₆～C₆₀Aryloxy group of (A), C₁～C₄₀Alkoxy group of (C)₆～C₆₀Arylamino group of (C)₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₁～C₄₀Alkylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀When a plurality of substituents are substituted, they may be the same as or different from each other.

According to a preferred embodiment of the present invention, the substituent represented by chemical formula 15 may be a substituent represented by chemical formula 16 below:

[ chemical formula 16]

In the chemical formula 16 as described above,

by "means the moiety that forms the bond;

R₁₁and R₁₂Each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₁～C₄₀Alkoxy group of (C)₆～C₆₀Aryloxy group of (A), C₃～C₄₀Alkylsilyl group of (C)₆～C₆₀Arylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀Or an arylamine group of (b), or a condensed ring formed by bonding to an adjacent group;

r is as defined above₁₁And R₁₂Alkyl, alkenyl, alkynyl,Aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamine, alkylsilyl, alkylboronyl, arylboronyl, arylphosphino, mono-or diarylphosphinoyl, and arylsilyl groups are each independently selected from deuterium, halogen, cyano, nitro, C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₆～C₆₀Aryloxy group of (A), C₁～C₄₀Alkoxy group of (C)₆～C₆₀Arylamino group of (C)₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₁～C₄₀Alkylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀One or more substituents of the group consisting of arylsilyl groups of (a), when substituted with a plurality of substituents, are the same as or different from each other;

Y₁、Y₃and Y₅Each is as defined in chemical formula 15 above.

According to a preferred embodiment of the present invention, the substituent represented by the above chemical formula 15 may be a substituent represented by any one of the following chemical formulae C-1 to C-5:

in the above chemical formulas C-1 to C-5,

by "is meant the portion that forms the bond,

R₁₁and R₁₂Each independently hydrogen, deuterium, halogen, cyano, nitro, C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₃～C₄₀Cycloalkyl radicals ofHeterocycloalkyl having 3 to 40 nucleonic nuclei, C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₁～C₄₀Alkoxy group of (C)₆～C₆₀Aryloxy group of (A), C₃～C₄₀Alkylsilyl group of (C)₆～C₆₀Arylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀Or an arylamine group of (b), or a condensed ring formed by bonding to an adjacent group;

r is as defined above₁₁And R₁₂Each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C, alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylboryl, arylboryl, arylphosphino, mono-or diarylphosphinoyl, and arylsilyl₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₆～C₆₀Aryloxy group of (A), C₁～C₄₀Alkoxy group of (C)₆～C₆₀Arylamino group of (C)₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₁～C₄₀Alkylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀When a plurality of substituents are substituted, they may be the same as or different from each other.

According to a preferred embodiment of the present invention, R is₁₁And R₁₂Each independently selected from C₁～C₄₀Alkyl group of (A) or (B),C₆～C₆₀Aryl and heteroaryl having a nuclear number of 5 to 60,

r is as defined above₁₁And R₁₂Each independently of the others, is selected from the group consisting of C₁～C₄₀Alkyl of (C)₆～C₆₀And one or more substituents selected from the group consisting of aryl groups having 5 to 60 atomic cores and heteroaryl groups having 5 to 60 atomic cores, which are the same or different from each other when substituted with a plurality of substituents.

According to a preferred embodiment of the present invention, R is₁₁And R₁₂Each independently selected from the group consisting of phenyl, biphenyl, pyridyl, pyrimidinyl, dibenzofuranyl, carbazolyl, fluorenyl, and dibenzothienyl,

r is as defined above₁₁And R₁₂Each of the phenyl, biphenyl, pyridyl, pyrimidyl, dibenzofuranyl, carbazolyl, fluorenyl, and dibenzothienyl groups of (A) is independently selected from C₁～C₄₀Alkyl of (C)₆～C₆₀And one or more substituents selected from the group consisting of aryl groups having 5 to 60 atomic cores and heteroaryl groups having 5 to 60 atomic cores, which are the same or different from each other when substituted with a plurality of substituents.

According to a preferred embodiment of the present invention, R is₁₁And R₁₂Each independently selected from the group consisting of phenyl, biphenyl, pyridyl, pyrimidinyl, dibenzofuranyl, carbazolyl, fluorenyl, and dibenzothienyl,

r is as defined above₁₁And R₁₂The phenyl group, biphenyl group, pyridyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group and dibenzothiophenyl group of (a) are each independently substituted or unsubstituted with one or more substituents selected from the group consisting of methyl group, ethyl group, propyl group, butyl group, phenyl group, biphenyl group, pyridyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group and dibenzothiophenyl group, and when a plurality of substituents are substituted, they are the same as or different from each other.

According to a preferred embodiment of the present invention, Ar is₂May be a substitution represented by the following chemical formula 17Base:

[ chemical formula 17]

In the chemical formula 17 as described above,

by "means the moiety that forms the bond;

R₁₃and R₁₄Each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₃～C₄₀Cycloalkyl of (a), heterocycloalkyl having a nuclear number of 3 to 40, C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₁～C₄₀Alkoxy group of (C)₆～C₆₀Aryloxy group of (A), C₃～C₄₀Alkylsilyl group of (C)₆～C₆₀Arylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀Or an arylamine group of (b), or a condensed ring formed by bonding to an adjacent group;

r is as defined above₁₃And R₁₄Each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C, alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylboryl, arylboryl, arylphosphino, mono-or diarylphosphinoyl, and arylsilyl₁～C₄₀Alkyl of (C)₂～C₄₀Alkenyl of, C₂～C₄₀Alkynyl of (A), C₆～C₆₀Aryl of (2), heteroaryl of atomic number 5 to 60, C₆～C₆₀Aryloxy group of (A), C₁～C₄₀Alkoxy group of (C)₆～C₆₀Arylamino group of (C)₃～C₄₀Cycloalkyl radicals ofHeterocycloalkyl having 3 to 40 nucleonic nuclei, C₁～C₄₀Alkylsilyl group of (C)₁～C₄₀Alkyl boron group of (2), C₆～C₆₀Aryl boron group of (1), C₆～C₆₀Aryl phosphine group of (A), C₆～C₆₀Mono-or diarylphosphinoyl groups of (A), and (C)₆～C₆₀When a plurality of substituents are substituted, they may be the same as or different from each other.

According to a preferred embodiment of the present invention, R is₁₃And R₁₄Each independently selected from C₁～C₄₀Alkyl of (C)₆～C₆₀Aryl and heteroaryl having a nuclear number of 5 to 60,

r is as defined above₁₃And R₁₄Each independently of the others, is selected from the group consisting of C₁～C₄₀Alkyl of (C)₆～C₆₀And one or more substituents selected from the group consisting of aryl groups having 5 to 60 atomic cores and heteroaryl groups having 5 to 60 atomic cores, which are the same or different from each other when substituted with a plurality of substituents.

According to a preferred embodiment of the present invention, R is₁₃And R₁₄Each independently selected from the group consisting of phenyl, biphenyl, pyridyl, pyrimidinyl, dibenzofuranyl, carbazolyl, fluorenyl, and dibenzothienyl,

r is as defined above₁₃And R₁₄Each of the phenyl, biphenyl, pyridyl, pyrimidyl, dibenzofuranyl, carbazolyl, fluorenyl, and dibenzothienyl groups of (A) is independently selected from C₁～C₄₀Alkyl of (C)₆～C₆₀And one or more substituents selected from the group consisting of aryl groups having 5 to 60 atomic cores and heteroaryl groups having 5 to 60 atomic cores, which are the same or different from each other when substituted with a plurality of substituents.

According to a preferred embodiment of the present invention, R is₁₃And R₁₄Each independently selected from the group consisting of phenyl, biphenyl, pyridyl, pyrimidinyl, dibenzofuranyl, carbazolyl, oxazolyl, and mixtures thereof,A fluorenyl group and a dibenzothienyl group,

r is as defined above₁₃And R₁₄The phenyl group, biphenyl group, pyridyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group and dibenzothiophenyl group of (a) are each independently substituted or unsubstituted with one or more substituents selected from the group consisting of methyl group, ethyl group, propyl group, butyl group, phenyl group, biphenyl group, pyridyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group and dibenzothiophenyl group, and when a plurality of substituents are substituted, they are the same as or different from each other.

The compound represented by chemical formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:

the compound of chemical formula 1 of the present invention can be synthesized according to a general synthesis method (see chem. Rev.,60:313 (1960); J.chem. SOC.4482 (1955); chem. Rev.95:2457(1995) and the like). The detailed synthetic procedures for the compounds of the present invention will be specifically described in the synthetic examples described later.

1. Organic electroluminescent element

In another aspect, the present invention relates to an organic electroluminescent element (organic EL element) comprising the compound represented by chemical formula 1 of the present invention described above.

Specifically, the present invention is an organic electroluminescent element including an anode (anode), a cathode (cathode), and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers includes the compound represented by chemical formula 1. In this case, the above-mentioned compounds may be used singly or in combination of two or more.

The one or more organic layers may be one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emission auxiliary layer, a lifetime improvement layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of the organic layers may include the compound represented by chemical formula 1.

The structure of the organic electroluminescent element of the present invention is not particularly limited, and for example, referring to fig. 1, the organic electroluminescent element includes an anode 10 and a cathode 20 facing each other, and an organic layer 30 located between the anode 10 and the cathode 20. Here, the organic layer 30 may include a hole transport layer 31, an emission layer 32, and an electron transport layer 34. Further, a hole transport assisting layer 33 may be included between the hole transport layer 31 and the light emitting layer 32, and an electron transport assisting layer 35 may be included between the electron transport layer 34 and the light emitting layer 32.

As another example of the present invention, referring to fig. 2, the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, and an electron injection layer 36 between the electron transport layer 34 and the cathode 20.

In the present invention, the hole injection layer 37 laminated between the hole transport layer 31 and the anode 10 is a layer which not only improves the interfacial properties between the ITO used as the anode and the organic material used as the hole transport layer 31, but also exerts a function of smoothing the surface of the ITO by coating the upper portion of the ITO having an uneven surface, and any of the hole injection layers generally used in the art may be used without any particular limitation, and for example, an amine compound may be used, but the present invention is not limited thereto.

The electron injection layer 36 is a layer laminated on the electron transport layer to facilitate electron injection from the cathode and to finally exhibit a function of improving power efficiency, and any electron injection layer commonly used in the art may be used without any particular limitation, and for example, LiF, Liq, NaCl, CsF, Li, or the like may be used₂O, BaO, etc.

In the present invention, although not shown, a light-emitting auxiliary layer may be further included between the hole transport auxiliary layer 33 and the light-emitting layer 32. The above-described light emission auxiliary layer may function to transport holes to the light emitting layer 32, and may function to adjust the thickness of the organic layer 30. The light-emission auxiliary layer may contain a hole-transporting substance, and may be made of the same substance as the hole-transporting layer 31.

In the present invention, although not shown, a lifetime improvement layer may be further included between the electron transport assisting layer 35 and the light-emitting layer 32. The holes that have moved to the light-emitting layer 32 beyond the ionization potential level in the organic light-emitting element are blocked by the high-energy barrier of the lifetime improving layer and cannot be diffused or moved to the electron transport layer, and as a result, the holes are confined in the light-emitting layer. Such a function of confining holes to the light-emitting layer inhibits diffusion of holes to the electron transport layer where electrons are moved by reduction, and suppresses a lifetime reduction phenomenon by an irreversible decomposition reaction due to oxidation, thereby contributing to improvement of the lifetime of the organic light-emitting element.

In the present invention, since the compound represented by chemical formula 1 is a compound in which EWG is bonded to a 5-membered aromatic ring or a 5-membered aromatic heterocycle such as indole, indazole, indene, benzofuran, benzothiophene, triazole, or the like, the compound has an energy level similar to that of carbazole, and thus can be adjusted to be higher than that of dopant and used as a host substance. In particular, benzofuran and benzothiophene have abundant electrons, and when used as an electron transport layer material for an organic electroluminescent device, they have high mobility, and thus an increase in light emission efficiency and a reduction in driving voltage can be expected. Further, since the molecular weight of the above-mentioned 5-membered aromatic ring or 5-membered aromatic heterocyclic ring of the present invention is smaller than that of a conventional compound, it is possible to perform vapor deposition at a relatively lower vapor deposition temperature than other materials at the time of vapor deposition, and therefore, the process is excellent and thermal stability can be improved.

Accordingly, the compound represented by chemical formula 1 of the present invention can be used as a material for any one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, which are organic layers of an organic electroluminescent device, preferably as a material for any one of the light emitting layer, the electron transport layer, and an electron transport auxiliary layer additionally stacked on the electron transport layer, and more preferably as a material for the electron transport layer or the electron transport auxiliary layer.

When the compound of the present invention is used as a material for a light-emitting layer, the compound represented by the above chemical formula 1 can be used as a phosphorescent host, a fluorescent host or a dopant material of the light-emitting layer, and preferably can be used as a phosphorescent host (blue, green and/or red phosphorescent host material).

In the present invention, the organic electroluminescent element may be formed by stacking an anode, one or more organic layers, and a cathode in this order, and may further include an insulating layer and an adhesive layer at an interface between the electrode and the organic layer.

The organic electroluminescent element of the present invention may be manufactured by forming other organic layers and electrodes using materials and methods known in the art, in addition to having at least one of the organic layers (e.g., electron transport assisting layer) comprising the compound represented by chemical formula 1.

The organic layer may be formed by a vacuum evaporation method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, blade coating, ink jet printing, and thermal transfer method.

The substrate usable in the present invention is not particularly limited, and a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, a sheet, or the like can be used.

Further, as the anode material, for example, a material made of a conductor having a high work function to facilitate hole injection, and metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO-Al or SnO₂A combination of a metal such as Sb and an oxide; polythiophenes, poly (3-methylthiophenes), poly [3,4- (ethylene-1, 2-dioxy) thiophenes]Conductive polymers such as (PEDT), polypyrrole, and polyaniline; and carbon black, but is not limited thereto.

The cathode material may be made of a conductor having a low work function to facilitate electron injection, and may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or an alloy thereof; and LiF/Al or LiO₂And a multilayer structure material such as Al, but not limited thereto.

Hereinafter, the present invention will be described in detail by way of examples. However, the following examples are merely illustrative of the present invention and the present invention is not limited to the following examples.

[ preparation example 1]Synthesis of A1

Under a stream of nitrogen, 8.5g (24.4mmol) of 3- (3-bromophenyl) -1-phenyl-1H-indazole, 7.4g (29.2mmol) of 4,4,4',4',5,5,5',5' -octamethyl-2, 2' -bis (1,3, 2-dioxaborane), 0.6g (0.7mmol) of Pd (dppf) Cl₂7.2g (73.1mmol) of KOAc, and 1, 4-bisThe mixture was stirred at 130 ℃ for 6 hours with an alkane (200 ml).

After the reaction, the extract was extracted with ethyl acetate and then MgSO₄Mixing waterThe fractions were removed and purified by column chromatography to give the objective compound A1(6.8g, 17.1mmol, yield 70%).

GC-Mass (theoretical value: 396.3g/mol, measured value: 396g/mol)

1H-NMR：δ1.25(s,12H),7.45～7.55(m,8H),7.62(s,1H),7.84～92(m,4H)

[ preparation example 2]Synthesis of A2

Under a stream of nitrogen, 8.5g (24.4mmol) of 3- (3-bromophenyl) -1- (pyridin-4-yl) -1H-indazole, 7.4g (29.2mol) of 4,4,4',4',5,5,5',5' -octamethyl-2, 2' -bis (1,3, 2-dioxaborane), 0.6g (0.7mmol) of Pd (dppf) Cl₂7.2g (73.1mmol) of KOAc, and 1, 4-bis

The mixture was stirred at 130 ℃ for 6 hours with an alkane (200 ml).

After the reaction, the extract was extracted with ethyl acetate and then MgSO₄The water was removed, and the mixture was purified by column chromatography to give target compound A3(7.3g, 18.3mmol, yield 75%).

GC-Mass (theoretical value: 397.3g/mol, measured value: 397g/mol)

1H-NMR：δ1.25(s,12H),7.45～7.55(m,5H),7.62(s,1H),7.84～92(m,4H),8.11～12(d,2H)

[ preparation example 3]Synthesis of A3

Under a stream of nitrogen, 10.4g (24.4mmol) of 3- (3-bromophenyl) -1, 5-diphenyl-1H-indazole, 7.4g (29.2mol) of 4,4,4',4',5,5,5',5' -octamethyl-2, 2' -bis (1,3, 2-dioxaborane), 0.6g (0.7mmol) of Pd (dppf) Cl₂7.2g (73.1mmol) of KOAc, and 1, 4-bisAlkyl (200ml) was mixed at 13Stirred at 0 ℃ for 6 hours.

After the reaction, the extract was extracted with ethyl acetate and then MgSO₄The water was removed, and the mixture was purified by column chromatography to give target compound A3(8.6g, 18.3mmol, yield 75%).

GC-Mass (theoretical: 472.4g/mol, measured: 472g/mol)

1H-NMR：δ1.25(s,12H),7.44～7.59(m,14H),7.62(s,1H),8.23～25(d,2H)

[ preparation example 4]Synthesis of A4

Under a stream of nitrogen, 9.7g (24.4mmol) of 1- (3-bromophenyl) -3-phenyl-3H-benzo [ e ]]Indazole, 7.4g (29.2mol) of 4,4,4',4',5,5,5',5' -octamethyl-2, 2' -bis (1,3, 2-dioxaborane), 0.6g (0.7mmol) of Pd (dppf) Cl₂7.2g (73.1mmol) of KOAc, and 1, 4-bisThe mixture was stirred at 130 ℃ for 6 hours with an alkane (200 ml).

After the reaction, the extract was extracted with ethyl acetate and then MgSO₄Water was removed, and the mixture was purified by column chromatography to give the objective compound A4(7.6g, 17.1mmol, yield 70%).

GC-Mass (theoretical: 446.4g/mol, measured: 446g/mol)

1H-NMR：δ1.25(s,12H),7.45～7.55(m,10H),7.62(s,1H),7.81～99(m,4H)

[ preparation example 5]Synthesis of A5

Under a stream of nitrogen, 9.8g (24.4mmol) of 1- (3-bromophenyl) -3- (pyridin-4-yl) -3H-benzo [ e ]]Indazole, 7.4g (29.2mol) of 4,4,4',4',5,5,5',5' -octamethyl-2, 2' -bis (1,3, 2-dioxaborane), 0.6g (0.7mmol) of Pd (dppf) Cl₂7.2g (73.1mmol) of KOAc, and 1, 4-bis

The mixture was stirred at 130 ℃ for 6 hours with an alkane (200 ml).

After the reaction, the extract was extracted with ethyl acetate and then MgSO₄Water was removed, and the mixture was purified by column chromatography to give the objective compound A5(7.6g, 17.1mmol, yield 70%).

GC-Mass (theoretical value: 447.4g/mol, measured value: 447g/mol)

1H-NMR：δ1.25(s,12H),7.45～7.55(m,9H),7.62(s,1H),7.81～99(m,2H),8.21～23(d,2H)

[ preparation example 6]Synthesis of A6

Under a stream of nitrogen, 9.7g (24.4mmol) of 3- (3-bromophenyl) -1-phenyl-1H-benzo [ f)]Indazole, 7.4g (29.2mol) of 4,4,4',4',5,5,5',5' -octamethyl-2, 2' -bis (1,3, 2-dioxaborane), 0.6g (0.7mmol) of Pd (dppf) Cl₂7.2g (73.1mmol) of KOAc, and 1, 4-bis

The mixture was stirred at 130 ℃ for 6 hours with an alkane (200 ml).

After the reaction, the extract was extracted with ethyl acetate and then MgSO₄Water was removed, and the mixture was purified by column chromatography to give the objective compound A6(7.6g, 17.1mmol, yield 70%).

GC-Mass (theoretical: 446.4g/mol, measured: 446g/mol)

1H-NMR：δ1.25(s,12H),7.45～7.55(m,10H),7.58(s,1H),7.61(s,1H),7.78(s,1H),7.81～86(m,2H)

[ preparation example 7]Synthesis of A7

Under a stream of nitrogen, 9.7g (24.4mmol) of 3- (3-bromophenyl) -1-phenyl-1H-benzo [ g ]]Indazole, 7.4g (29.2mol) of 4,44',4',5,5,5',5' -octamethyl-2, 2' -bis (1,3, 2-dioxaborane), 0.6g (0.7mmol) of Pd (dppf) Cl₂7.2g (73.1mmol) of KOAc, and 1, 4-bisThe mixture was stirred at 130 ℃ for 6 hours with an alkane (200 ml).

After the reaction, the extract was extracted with ethyl acetate and then MgSO₄Water was removed, and the mixture was purified by column chromatography to give the objective compound A7(7.6g, 17.1mmol, yield 70%).

GC-Mass (theoretical value: 446.36g/mol, measured value: 446g/mol)

1H-NMR：δ1.25(s,12H),7.45～7.54(m,10H),7.62(s,1H),7.81～88(m,4H)

[ preparation example 8]Synthesis of A8

Under a stream of nitrogen, 8.5g (24.4mmol) of 3- (3-bromophenyl) -1-phenyl-1H-indole, 7.4g (29.2mol) of 4,4,4',4',5,5,5',5' -octamethyl-2, 2' -bis (1,3, 2-dioxaborane), 0.6g (0.7mmol) of Pd (dppf) Cl₂7.2g (73.1mmol) of KOAc, and 1, 4-bis

The mixture was stirred at 130 ℃ for 6 hours with an alkane (200 ml).

After the reaction, the extract was extracted with ethyl acetate and then MgSO₄Water was removed, and the mixture was purified by column chromatography to give the objective compound A8(6.7g, 17.1mmol, yield 70%).

GC-Mass (theoretical value: 395.3g/mol, measured value: 395g/mol)

1H-NMR：δ1.25(s,12H),7.43～7.55(m,9H),7.62(s,1H),7.84～92(m,4H)

[ preparation example 9]Synthesis of A9

Under a stream of nitrogen, 8.5g (24.4mmol) of 3- (3-bromophenyl) -1- (pyridin-4-yl) -1H-indole, 7.4g (29.2mol) of 4,4,4',4',5,5,5',5' -octamethyl-2, 2' -bis (1,3, 2-dioxaborane), 0.6g (0.7mmol) of Pd (dppf) Cl₂7.2g (73.1mmol) of KOAc, and 1, 4-bis

The mixture was stirred at 130 ℃ for 6 hours with an alkane (200 ml).

After the reaction, the extract was extracted with ethyl acetate and then MgSO₄Water was removed, and the mixture was purified by column chromatography to give the objective compound A8(6.8g, 17.1mmol, yield 70%).

GC-Mass (theoretical value: 396.3g/mol, measured value: 396g/mol)

1H-NMR：δ1.25(s,12H),7.41～7.55(m,6H),7.62(s,1H),7.84～92(m,4H),8.11～12(d,2H)

[ preparation example 10]Synthesis of A10

Under a stream of nitrogen, 10.3g (24.4mmol) of 3- (3-bromophenyl) -1, 5-diphenyl-1H-indole, 7.4g (29.2mol) of 4,4,4',4',5,5,5',5' -octamethyl-2, 2' -bis (1,3, 2-dioxaborane), 0.6g (0.7mmol) of Pd (dppf) Cl₂7.2g (73.1mmol) of KOAc, and 1, 4-bis

The mixture was stirred at 130 ℃ for 6 hours with an alkane (200 ml).

After the reaction, the extract was extracted with ethyl acetate and then MgSO₄The water was removed, and the mixture was purified by column chromatography to give target compound A10(8.6g, 18.3mmol, yield 75%).

GC-Mass (theoretical value: 471.4g/mol, measured value: 471g/mol)

1H-NMR：δ1.25(s,12H),7.41～7.60(m,15H),7.63(s,1H),8.23～25(d,2H)

[ preparation example 11]Synthesis of A11

Under a stream of nitrogen, 9.7g (24.4mmol) of 1- (3-bromophenyl) -3-phenyl-3H-benzo [ e ]]Indole, 7.4g (29.2mol) 4,4,4',4',5,5,5',5' -octamethyl-2, 2' -bis (1,3, 2-dioxaborane), 0.6g (0.7mmol) Pd (dppf) Cl₂7.2g (73.1mmol) of KOAc, and 1, 4-bis

The mixture was stirred at 130 ℃ for 6 hours with an alkane (200 ml).

After the reaction, the extract was extracted with ethyl acetate and then MgSO₄Water was removed, and the mixture was purified by column chromatography to give the objective compound A11(7.6g, 17.1mmol, yield 70%).

GC-Mass (theoretical: 445.4g/mol, measured: 445g/mol)

1H-NMR：δ1.25(s,12H),7.41～7.55(m,11H),7.62(s,1H),7.81～99(m,4H)

[ preparation example 12]Synthesis of A12

Under a stream of nitrogen, 9.7g (24.4mmol) of 1- (3-bromophenyl) -3- (pyridin-4-yl) -3H-benzo [ e ]]Indazole, 7.4g (29.2mol) of 4,4,4',4',5,5,5',5' -octamethyl-2, 2' -bis (1,3, 2-dioxaborane), 0.6g (0.7mmol) of Pd (dppf) Cl₂7.2g (73.1mmol) of KOAc, and 1, 4-bis

The mixture was stirred at 130 ℃ for 6 hours with an alkane (200 ml).

After the reaction, the extract was extracted with ethyl acetate and then MgSO₄Water was removed, and the mixture was purified by column chromatography to give the objective compound A12(7.6g, 17.1mmol, yield 70%).

GC-Mass (theoretical: 446.4g/mol, measured: 446g/mol)

1H-NMR：δ1.25(s,12H),7.42～7.55(m,10H),7.62(s,1H),7.81～99(m,2H),8.21～23(d,2H)

[ preparation example 13]Synthesis of A13

Under a stream of nitrogen, 9.7g (24.4mmol) of 3- (3-bromophenyl) -1-phenyl-1H-benzo [ f)]Indole, 7.4g (29.2mol) 4,4,4',4',5,5,5',5' -octamethyl-2, 2' -bis (1,3, 2-dioxaborane), 0.6g (0.7mmol) Pd (dppf) Cl₂7.2g (73.1mmol) of KOAc, and 1, 4-bis

The mixture was stirred at 130 ℃ for 6 hours with an alkane (200 ml).

After the reaction, the extract was extracted with ethyl acetate and then MgSO₄Water was removed, and the mixture was purified by column chromatography to give the objective compound A13(7.6g, 17.1mmol, yield 70%).

GC-Mass (theoretical: 445.4g/mol, measured: 445g/mol)

1H-NMR：δ1.25(s,12H),7.42～7.55(m,11H),7.58(s,1H),7.61(s,1H),7.78(s,1H),7.81～85(m,2H)

[ preparation example 14]Synthesis of A14

Under a stream of nitrogen, 9.7g (24.4mmol) of 3- (3-bromophenyl) -1-phenyl-1H-benzo [ g ]]Indazole, 7.4g (29.2mol) of 4,4,4',4',5,5,5',5' -octamethyl-2, 2' -bis (1,3, 2-dioxaborane), 0.6g (0.7mmol) of Pd (dppf) Cl₂7.2g (73.1mmol) of KOAc, and 1, 4-bis

The mixture was stirred at 130 ℃ for 6 hours with an alkane (200 ml).

After the reaction, the extract was extracted with ethyl acetate and then MgSO₄Water was removed, and the mixture was purified by column chromatography to give the objective compound A14(7.6g, 17.1mmol, yield 70%).

GC-Mass (theoretical value: 445.37g/mol, measured value: 445g/mol)

1H-NMR:δ1.25(s,12H),7.42～7.54(m,11H),7.62(s,1H),7.82～89(m,4H)

[ preparation example 15]Synthesis of A15

Under a stream of nitrogen, 6.7g (24.4mmol) of 2- (3-bromophenyl) benzofuran, 7.4g (29.2mol) of 4,4,4',4',5,5,5',5' -octamethyl-2, 2' -bis (1,3, 2-dioxaborane), 0.6g (0.7mmol) of Pd (dppf) Cl₂7.2g (73.1mmol) of KOAc, and 1, 4-bis

The mixture was stirred at 130 ℃ for 6 hours with an alkane (200 ml).

After the reaction, the extract was extracted with ethyl acetate and then MgSO₄Water was removed, and the mixture was purified by column chromatography to give the objective compound A15(5.5g, 17.1mmol, yield 70%).

GC-Mass (theoretical value: 320.2g/mol, measured value: 320g/mol)

1H-NMR:δ1.25(s,12H),7.11(s,1H),7.58(s,1H),7.67～7.89(m,7H)

[ preparation example 16]Synthesis of A16

Under a stream of nitrogen, 7.3g (24.4mmol) of 2- (3-bromophenyl) -1, 1-dimethyl-1H-indene, 7.4g (29.2mol) of 4,4,4',4',5,5,5',5' -octamethyl-2, 2' -bis (1,3, 2-dioxaborane), 0.6g (0.7mmol) of Pd (dppf) Cl₂7.2g (73.1mmol) of KOAc, and 1, 4-bisThe mixture was stirred at 130 ℃ for 6 hours with an alkane (200 ml).

After the reaction, the extract was extracted with ethyl acetate and then MgSO₄Removing water, passing through columnPurification by chromatography gave the desired compound A16(5.9g, 17.1mmol, yield 70%).

GC-Mass (theoretical value: 346.28g/mol, measured value: 346g/mol)

1H-NMR:δ1.25(s,12H),1.69(s,6H),7.01(s,1H),7.45(s,1H),7.57～7.77(m,7H)

[ preparation example 17]Synthesis of A17

Under a nitrogen gas flow, 2- (3-bromophenyl) benzo [ b ]]Thiophene 7.0g (24.4mmol), 4,4,4',4',5,5,5',5' -octamethyl-2, 2' -bis (1,3, 2-dioxaborane) 7.4g (29.2mol), Pd (dppf) Cl₂0.6g (0.7mmol), KOAc 7.2g (73.1mmol), and 1, 4-bis

The mixture was stirred at 130 ℃ for 6 hours with an alkane (200 ml).

After the reaction, the extract was extracted with ethyl acetate and then MgSO₄Water was removed, and the mixture was purified by column chromatography to give the objective compound A17(6.1g, 18.3mmol, yield 75%).

GC-Mass (theoretical value: 336.26g/mol, measured value: 336g/mol)

1H-NMR:δ1.25(s,12H),7.51(s,1H),7.59(s,1H),7.72～7.92(m,7H)

Synthesis example 1]Synthesis of R1

Under a stream of nitrogen, 6.8g (17.1mmol) of A1, 8.7g (18.8mmol) of 2- (3' -bromobiphenyl-3-yl) -4, 6-diphenyl-1, 3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.1g (51.2mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄The water is removed. Removing the solvent from the organic layer, and passing through column colorThe resulting mixture was purified to obtain the objective compound R1(8.4g, 12.8mmol, yield 75%).

GC-Mass (theoretical value: 653.8g/mol, measured value: 653g/mol)

Synthesis example 2]Synthesis of R8

Under a stream of nitrogen, 6.8g (17.1mmol) of A1, 9.2g (18.8mmol) of 2-bromo-4, 6-bis (dibenzo [ b, d ]) were added]Furan-4-yl) -1,3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.1g (51.2mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄The water is removed. The solvent in the organic layer was removed, and the residue was purified by column chromatography to give the desired compound R8(9.0g, 13.1mmol, yield 77%).

GC-Mass (theoretical value: 681.8g/mol, measured value: 682g/mol)

[ Synthesis example 3]Synthesis of R21

Under a stream of nitrogen, 6.8g (17.1mmol) of A2, 8.7g (18.8mmol) of 2- (3' -bromobiphenyl-3-yl) -4, 6-diphenyl-1, 3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.1g (51.2mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄The water is removed. The solvent in the organic layer was removed, and the residue was purified by column chromatography to give the desired compound R21(7.8g, 11.9mmol, yield 70%).

GC-Mass (theoretical value: 654.8g/mol, measured value: 655g/mol)

[ Synthesis example 4]Synthesis of R41

Under a stream of nitrogen, 8.6g (18.3mmol) of A3, 9.3g (20.1mmol) of 2- (3' -bromobiphenyl-3-yl) -4, 6-diphenyl-1, 3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.1g (73.1mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄The water is removed. The solvent in the organic layer was removed, and the residue was purified by column chromatography to give the desired compound R41(10.0g, 13.7mmol, yield 75%).

GC-Mass (theoretical value: 729.9g/mol, measured value: 730g/mol)

Synthesis example 5]Synthesis of R61

Under a stream of nitrogen, 7.6g (17.1mmol) of A4, 8.7g (18.8mmol) of 2- (3' -bromobiphenyl-3-yl) -4, 6-diphenyl-1, 3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.1g (51.2mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄The water is removed. The solvent in the organic layer was removed, and the residue was purified by column chromatography to give the desired compound R61(9.0g, 12.8mmol, yield 75%).

GC-Mass (theoretical value: 703.9g/mol, measured value: 703g/mol)

[ Synthesis example 6]Synthesis of R68

Under a stream of nitrogen, 7.6g (17.1mmol) of A4, 9.2g (18.8mmol) of 2-bromo-4, 6-bis (dibenzo [ b, d ]) were added]Furan-4-yl) -1,3, 5-triazine, 1.0g (5 mol%) ofPd(PPh₃)₄And 7.1g (51.2mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄The water is removed. The solvent in the organic layer was removed, and the residue was purified by column chromatography to give the desired compound R68(9.4g, 12.8mmol, yield 75%).

GC-Mass (theoretical value: 731.8g/mol, measured value: 731g/mol)

[ Synthesis example 7]Synthesis of R81

Under a stream of nitrogen, 7.6g (17.1mmol) of A5, 8.7g (18.8mmol) of 2- (3' -bromobiphenyl-3-yl) -4, 6-diphenyl-1, 3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.1g (51.2mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄The water is removed. The solvent in the organic layer was removed, and the residue was purified by column chromatography to give the desired compound R81(8.9g, 12.6mmol, yield 74%).

GC-Mass (theoretical value: 703.9g/mol, measured value: 704g/mol)

Synthesis example 8]Synthesis of R101

Under a stream of nitrogen, 7.6g (17.1mmol) of A6, 8.7g (18.8mmol) of 2- (3' -bromobiphenyl-3-yl) -4, 6-diphenyl-1, 3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.1g (51.2mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄The water is removed. An organic layer is formedAfter removal of the solvent (b), the residue was purified by column chromatography to give the desired compound R101(9.0g, 12.8mmol, yield 75%).

GC-Mass (theoretical value: 703.9g/mol, measured value: 703g/mol)

[ Synthesis example 9]Synthesis of R121

Under a stream of nitrogen, 7.6g (17.1mmol) of A7, 8.7g (18.8mmol) of 2- (3' -bromobiphenyl-3-yl) -4, 6-diphenyl-1, 3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.1g (51.2mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄The water is removed. The solvent in the organic layer was removed, and the residue was purified by column chromatography to give the desired compound R121(8.9g, 12.0mmol, yield 74%).

GC-Mass (theoretical value: 703.9g/mol, measured value: 703g/mol)

[ Synthesis example 10]Synthesis of R141

Under a stream of nitrogen, 6.7g (17.1mmol) of A8, 8.7g (18.8mmol) of 2- (3' -bromobiphenyl-3-yl) -4, 6-diphenyl-1, 3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.1g (51.2mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄And (4) removing water. The solvent in the organic layer was removed, and the residue was purified by column chromatography to give the desired compound R141(8.3g, 12.8mmol, yield 75%).

GC-Mass (theoretical value: 652.8g/mol, measured value: 653g/mol)

Synthesis example 11]Synthesis of R148

Under a stream of nitrogen, 6.7g (17.1mmol) of A8, 9.2g (18.8mmol) of 2-bromo-4, 6-bis (dibenzo [ b, d ]) were added]Furan-4-yl) -1,3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.1g (51.2mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄The water is removed. The solvent in the organic layer was removed, and the residue was purified by column chromatography to give the desired compound R148(8.7g, 12.8mmol, yield 75%).

GC-Mass (theoretical value: 680.8g/mol, measured value: 681g/mol)

Synthesis example 12]Synthesis of R161

Under a stream of nitrogen, 6.8g (17.1mmol) of A9, 8.7g (18.8mmol) of 2- (3' -bromobiphenyl-3-yl) -4, 6-diphenyl-1, 3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.1g (51.2mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄The water is removed. The solvent in the organic layer was removed, and the residue was purified by column chromatography to give the desired compound R161(7.9g, 11.1mmol, yield 71%).

GC-Mass (theoretical value: 653.8g/mol, measured value: 654g/mol)

[ Synthesis example 13]Synthesis of R181

Under a stream of nitrogen, 8.6g (18.3mmol) of A10, 9.3g (20.1mmol) of 2- (3' -bromobiphenyl-3-yl group were added) 4, 6-Diphenyl-1, 3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.1g (73.1mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄The water is removed. The solvent in the organic layer was removed, and the residue was purified by column chromatography to give the desired compound R181(10.0g, 13.7mmol, yield 75%).

GC-Mass (theoretical value: 729.9g/mol, measured value: 730g/mol)

Synthesis example 14]Synthesis of R201

Under a stream of nitrogen, 7.6g (17.1mmol) of A11, 8.7g (18.8mmol) of 2- (3' -bromobiphenyl-3-yl) -4, 6-diphenyl-1, 3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.1g (51.2mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄The water is removed. The solvent in the organic layer was removed, and the residue was purified by column chromatography to give the desired compound R201(9.0g, 12.8mmol, yield 75%).

GC-Mass (theoretical value: 703.9g/mol, measured value: 703g/mol)

[ Synthesis example 15]Synthesis of R208

Under a stream of nitrogen, 7.6g (17.1mmol) of A11, 9.2g (18.8mmol) of 2-bromo-4, 6-bis (dibenzo [ b, d ]) were added]Furan-4-yl) -1,3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.1g (51.2mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After the reaction is finished, the organic phase is separated by dichloromethaneSeparating the layers with MgSO₄The water is removed. The solvent in the organic layer was removed, and the residue was purified by column chromatography to give the desired compound R208(9.4g, 12.8mmol, yield 75%).

GC-Mass (theoretical value: 731.8g/mol, measured value: 731g/mol)

Synthesis example 16]Synthesis of R221

Under a stream of nitrogen, 7.6g (17.1mmol) of A12, 8.7g (18.8mmol) of 2- (3' -bromobiphenyl-3-yl) -4, 6-diphenyl-1, 3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.1g (51.2mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄The water is removed. The solvent in the organic layer was removed, and the residue was purified by column chromatography to give the objective compound R221(8.9g, 12.6mmol, yield 74%).

GC-Mass (theoretical value: 703.9g/mol, measured value: 704g/mol)

[ Synthesis example 17]Synthesis of R241

Under a stream of nitrogen, 7.6g (17.1mmol) of A13, 8.7g (18.8mmol) of 2- (3' -bromobiphenyl-3-yl) -4, 6-diphenyl-1, 3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.1g (51.2mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄The water is removed. The solvent in the organic layer was removed, and the residue was purified by column chromatography to give the desired compound R241(9.0g, 12.8mmol, yield 75%).

GC-Mass (theoretical value: 702.9g/mol, measured value: 703g/mol)

[ Synthesis example 18]Synthesis of R261

Under a stream of nitrogen, 7.6g (17.1mmol) of A14, 8.7g (18.8mmol) of 2- (3' -bromobiphenyl-3-yl) -4, 6-diphenyl-1, 3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.1g (51.2mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄The water is removed. The solvent in the organic layer was removed, and the residue was purified by column chromatography to give the desired compound R261(8.9g, 12.0mmol, yield 74%).

GC-Mass (theoretical value: 702.9g/mol, measured value: 703g/mol)

[ Synthesis example 19]Synthesis of R281

Under a stream of nitrogen, 5.5g (17.1mmol) of A15, 8.7g (18.8mmol) of 2- (3' -bromobiphenyl-3-yl) -4, 6-diphenyl-1, 3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.1g (51.2mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄The water is removed. The solvent in the organic layer was removed, and the residue was purified by column chromatography to give the desired compound R281(9.9g, 12.8mmol, yield 75%).

GC-Mass (theoretical value: 577.7g/mol, measured value: 578g/mol)

[ Synthesis example 20]Synthesis of R285

Under a stream of nitrogen, adding5.5g (17.1mmol) of A15, 9.2g (18.8mmol) of 2-bromo-4, 6-bis (dibenzo [ b, d ]]Furan-4-yl) -1,3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.1g (51.2mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄The water is removed. The solvent in the organic layer was removed, and the residue was purified by column chromatography to give the target compound R285(8.0g, 13.1mmol, yield 77%).

GC-Mass (theoretical value: 605.7g/mol, measured value: 606g/mol)

Synthesis example 21]Synthesis of R286

Under a stream of nitrogen, 5.9g (17.1mmol) of A16, 8.7g (18.8mmol) of 2- (3' -bromobiphenyl-3-yl) -4, 6-diphenyl-1, 3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.1g (51.2mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄The water is removed. The solvent in the organic layer was removed, and the residue was purified by column chromatography to give the objective compound R286(7.2g, 11.9mmol, yield 70%).

GC-Mass (theoretical: 603.8g/mol, measured: 604g/mol)

[ Synthesis example 22]Synthesis of R291

Under a stream of nitrogen, 6.1g (18.3mmol) of A17, 9.3g (20.1mmol) of 2- (3' -bromobiphenyl-3-yl) -4, 6-diphenyl-1, 3, 5-triazine, 1.0g (5 mol%) of Pd (PPh)₃)₄And 7.6g (73.1mmol) of potassium carbonate and 80ml/40ml/40ml of toluene/H₂O/ethanol, stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated with dichloromethane and MgSO₄The water is removed. The solvent in the organic layer was removed, and the residue was purified by column chromatography to give the desired compound R291(9.2g, 13.7mmol, yield 75%).

GC-Mass (theoretical value: 669.9g/mol, measured value: 670g/mol)

[ examples 1 to 6]Fabrication of green organic electroluminescent device

The compound synthesized in synthesis example was purified by sublimation with high purity by a generally known method, and then a green organic electroluminescent element was produced by the following procedure.

First, will be provided with

A glass substrate coated with ITO (indium tin oxide) in a thin film thickness was ultrasonically washed with distilled water. After the completion of the distilled water washing, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to an ultraviolet OZONE (UV OZONE) washer (Power sonic 405, HWASHIN TECH), cleaned with UV for 5 minutes, and then transferred to a vacuum evaporator.

On the ITO transparent electrode thus prepared, m-MTDATA (60nm)/TCTA (80nm)/R1, R8, R141, R148, R201, and R208 + 10% Ir (ppy) were stacked in this order₃(300nm)/BCP(10nm)/Alq₃(30nm)/LiF (1nm)/Al (200nm), an organic electroluminescent element was produced.

m-MTDATA、TCTA、Ir(ppy)₃The structures of CBP and BCP are as follows.

Comparative example 1]Fabrication of green organic electroluminescent device

A green organic electroluminescent element was produced in the same manner as in example 1, except that CBP was used as the light-emitting host material instead of the compound R141 when the light-emitting layer was formed.

[ evaluation example 1]

For each of the green organic electroluminescent elements produced in examples 1 to 6 and comparative example 2, the current density (10) mA/cm was measured²The driving voltage, current efficiency and light emission peak at the time are shown in table 1 below.

[ Table 1]

Sample (I)	Main body	Drive voltage (V)	EL peak (nm)	Current efficiency (cd/A)
					Example 1	R1	5.2	515	12.5
Example 2	R8	4.3	515	11.4
					Example 3	R141	5.1	515	12.3
Example 4	R148	4.2	515	11.1
					Example 5	R201	5.4	515	12.2
Example 6	R208	4.4	515	10.8
					Comparative example 1	CBP	7.1	516	7.2

As shown in table 1, it is understood that when the compounds of the present invention (R1, R8, R141, R148, R201, and R208) are used as the light-emitting layer of a green organic EL element (examples 1 to 6), the green organic EL element exhibits more excellent performance in terms of efficiency and driving voltage than the conventional green organic EL element using CBP (comparative example 1).

[ examples 7 to 28]Fabrication of blue organic electroluminescent device

The compound synthesized in synthesis example was purified by sublimation with high purity by a generally known method, and then a blue organic electroluminescent element was produced by the following procedure.

First, will be provided with

A glass substrate coated with ITO (indium tin oxide) in a thin film thickness was ultrasonically washed with distilled water. After the completion of the distilled water washing, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to an ultraviolet OZONE (UV OZONE) washer (Powersonic 405, HWASHIN TECH), cleaned with UV for 5 minutes, and then transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as described above, DS-205 ((Takara electronics 80nm)/NPB (15nm)/ADN + 5% DS-405 ((Takara electronics, 30nm)/R1, R8, R21, R41, R61, R68, R81, R101, R121, R141, R148, R161, R181, R201, R208, R221, R241, R261, R281, R285, R286, R291(5nm)/Alq3(25nm)/LiF (1nm)/Al (200nm) were sequentially stacked to produce an organic electroluminescent element.

Comparative example 2]Fabrication of blue organic electroluminescent device

As the electron transport assisting layer material, Alq as an electron transport layer material was deposited at 30nm without using R1₃A blue organic electroluminescent device was fabricated in the same manner as in example 6, except that the thickness was not 25 nm.

NPB, AND AND Alq used in examples 6 to 28 AND comparative example 2 described above₃The structure of (1) is as follows.

Comparative example 3]Fabrication of blue organic electroluminescent device

A blue organic electroluminescent element was produced in the same manner as in example 6, except that a1 having the following structural formula was used instead of R1 as the electron transport assisting layer material.

[ evaluation example 2]

For examples 7 to 28 and comparative example 2Organic electroluminescent elements manufactured in each of the items 3 to 3, and the current density was measured at 10mA/cm²The results of the driving voltage, emission wavelength, and current efficiency are shown in table 2 below.

[ Table 2]

Sample (I)	Electron transport auxiliary layer	Drive voltage (V)	Luminous peak (nm)	Current efficiency (cd/A)
					Example 7	R1	4.4	458	8.3
Example 8	R8	3.9	458	7.5
					Example 9	R21	4.4	458	8.0
Example 10	R41	4.4	458	8.2
					Example 11	R61	4.4	458	8.1
Example 12	R68	4.4	458	8.2
					Example 13	R81	4.4	458	8.3
Example 14	R101	4.4	458	8.0
					Example 15	R121	4.4	458	8.2
Example 16	R141	4.3	458	7.8
					Example 17	R148	3.5	458	7.1
Example 18	R161	4.4	458	7.3
					Example 19	R181	4.5	458	7.4
Example 20	R201	4.1	458	7.5
					Example 21	R208	3.9	458	7.0
Example 22	R221	4.2	458	7.5
					Example 23	R241	4.1	458	7.6
Example 24	R261	4.5	458	7.3
					Example 25	R281	3.8	458	6.9
Example 26	R285	3.4	458	6.8
					Example 27	R286	4.7	458	7.2
Example 28	R291	3.8	458	6.9
					Comparative example 2	Alq3	4.8	458	6.2
Comparative example 3	A1	4.7	457	6.5

As shown in table 2 above, it is understood that the blue organic electroluminescent elements (examples 6 to 28) using the compounds of the present invention for the electron transport assisting layer exhibit superior performance in terms of current efficiency, light emission peak and driving voltage, as compared to the blue organic electroluminescent elements (comparative examples 2 and 3) without the electron transport assisting layer.

Examples 29 to 32]Fabrication of blue organic electroluminescent device

The compound synthesized in synthesis example was purified by sublimation with high purity by a generally known method, and then a green organic electroluminescent element was produced by the following procedure.

First, will be provided with

A glass substrate coated with ITO (indium tin oxide) in a thin film thickness was ultrasonically washed with distilled water. After the completion of the distilled water washing, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to an ultraviolet OZONE (UV OZONE) washer (Powersonic 405, HWASHIN TECH), cleaned with UV for 5 minutes, and then transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as described above, compounds (30nm)/LiF (1nm)/Al (200nm) of DS-205 ((Takara Shuzo, Ltd.)/80 nm)/NPB (15nm)/ADN + 5% DS-405 ((Takara Shuzo, Ltd.)/30 nm)/R1, R8, R21 and R41 were sequentially stacked to prepare an organic electroluminescent element.

Comparative example 4]Fabrication of blue organic electroluminescent device

As the electron transporting layer material, Alq was used₃A blue organic electroluminescent device was fabricated in the same manner as in example 29, except that R1 was replaced.

Comparative example 5]Fabrication of blue organic electroluminescent device

A blue organic electroluminescent element was produced in the same manner as in example 29, except that R1 was not used as the electron transporting layer material.

[ evaluation example 3]

For the blue organic electroluminescent elements produced in examples 29 to 32 and comparative examples 2 and 3, respectively, the current density was measured at 10mA/cm²The results of the driving voltage, the current efficiency, and the emission wavelength are shown in table 3 below.

[ Table 3]

Sample (I)	Electron transport layer	Drive voltage (V)	Luminous peak (nm)	Current efficiency (cd/A)
					Example 29	R1	4.5	455	8.7
Example 30	R8	3.9	455	7.8
					Example 31	R21	4.4	455	8.4
Example 32	R41	4.2	455	9.3
					Comparative example 4	Alq3	4.7	458	5.5
Comparative example 5	-	4.8	460	6.2

As shown in Table 3, it is understood that blue organic electroluminescent elements using the compounds of the present invention for the electron transport layer (examples 29 to 32) and conventional organic electroluminescent elements using Alq₃Blue organic electroluminescent element for electron transport layer (comparative example 4) and blue organic electroluminescent element without electron transport layerThe electroluminescent element (comparative example 5) showed excellent performance in terms of driving voltage, emission peak and current efficiency, compared with those of the above-mentioned comparative example.

Description of the symbols

10: anode 20: cathode electrode

30: organic layer 31: hole transport layer

32: light-emitting layer 33: hole transport auxiliary layer

34: electron transport layer 35: electron transport auxiliary layer

36: electron injection layer 37: hole injection layer